Sissy Humiliation

Fucking With Heads

2011-06-22T11:18:00.004-04:00

In my post below "Have you ever worn women's silky underwear?" Chrisissy replied that maybe telling them might be more fun than just ending the relationship. Well, Chrisissy, you're right, and I have ended a couple relationships that way.

In fact, I went through a phase with a number of women where I would drop the hints, and when the reactions were largely unfavorable, I'd just bail via wearing something obviously feminine. In most cases, these women didn't know other people in my sphere. One of my favorite "drops" would be about tights. I'd be talking about working out and wearing my tights. It's almost funny how the reactions of about three different women were almost identical. They'd simply reply, "Tights?" In every case, they said it in two syllables, "tie-eets" with a rising inflection.

"Sure. I wear them sometimes when I'm on my elliptical machine." Their reactions would be guarded. I'd act like it was normal. After all, lots of guys wear tights for working out.

One girl was inquisitive and pressed, "What kind of tights?" I acted dumb. "I dunno. Danskin, I think."

"You mean footed tights?"

"Well, I guess. Aren't they all footed?"

"Ummm... oooo-kaaaay." I was starting to open the door that she would eventually close quietly yet firmly. I didn't care at that point.

Sometimes I'd get a little frisky knowing the end was near. I showed up to meet a date at a restaurant wearing Chic jeans and a plain woman's blouse. At a distance, it looked quite normal, but it didn't take her too long to notice the nature of my outfit. She never returned my calls again.

Another girl surely spotted the waistband of my pantyhose before never speaking to me again.

A girl named Lois was cautiously OK with my tights. I stopped by one day after a trip to Target where I had bought a leotard. A thong leotard no less. I told her I had bought this top but thought I might have to take it back. I showed her the top part of it without letting her see the cut of the bottom. "That's a ladies top..." she reported. "Well, it's a fairly plain design. Let me try it on."

In the bathroom, I said, "Oh goodness!" acting surprised.

"What is it?" she inquired.

"Do you know what a thong is?" I said, embarrassed.

"Yes..." in a two-syllable tone.

"I don't believe this..." opening the door to reveal my black tights and thong leotard. "I guess this will have to go back."

Poor Lois was half laughing but alarmed that I'd buy let alone wear such a garment.

Oddly enough, that afternoon Lois gave me two pairs of her panties before sending me out. She never returned my calls again. I can still hear her reaction to my leotard and tights.

Elbows On The Table

2011-06-09T15:33:00.007-04:00

Put your elbows on the table, Sissy. That's it. Just relax, now. I'll be very gentle. Let's just unzip you back here... Now, honey, just relax. It's only going to hurt for a short while. I'm going to use lots of lube on my strapon... and then I'm going to pene... trate... you... gently. Don't fight it. It will only hurt more. It's almost all the way in now. Don't cry...

"Have you ever worn women's silky underwear?"

2010-10-18T11:13:00.009-04:00

"I want to ask you: have you ever worn women's silky underwear?"

Silence.

"What?" I responded, curiously. This phone conversation had just taken a very rapid turn.

She repeated slowly with more insistence, "Have you ever worn women's silky underwear?"

Cindy was the original Miss Priss. Well educated, prim, proper, and fussy. We'd been dating for about six months, and I don't know what really attracted me to her.

As with many women I dated, I dropped hints here and there... like how I "had to" wear pantyhose under my pants to do some work outdoors on a particularly cold and windy day. Or how I dressed up as a girl for Halloween. If it got the right giggly response, I would tell them how my girlfriend at the time had dared me wear EVERYTHING including bra, panties, pantyhose, girdle, heels, etc. Well, OK, that's not entirely true because Terri, the girl I was living with, knew full well of my crossdressing, and she just helped me dress up one Halloween. She provided some of the outer wear, and I already had more lingerie than she did.

Most women would find it amusing and think of me as a more evolved man because "now you know what we have to go through," and I would engage them in an extended conversation about wearing such underthings and navigating in high heels and a girdle (I wouldn't mention that I particularly like girdles because they hold a butt plug firmly in place). Maybe I'd throw in a little tidbit about how I wore a silky nightgown to bed that night after the party. (OK, I wore a nightie to bed every night with Terri.) That might get a real rise because I would be hitting the edge of concern. One girlfriend giggled and said, "I'm beginning to wonder about you!" and then I'd back down and say, well, it was an interesting experiment.

Cindy wasn't amused by this, although she wasn't immediately repulsed. And while I didn't go so far as revealing the "nightie" night, I continued to bring up the subject gingerly until it must have reached critical mass for her. Perhaps she had a consultation with a female friend or her mother, expressing concern over these things that I mentioned. "Just ask him outright! Ask him if he ever wore women's silky underwear. After all, that's what 'those men' like to do!"

I was a bit bemused by the nature of her question. I toyed with retorting, "You're worried about 'silky underwear?' Women's cotton panty briefs don't count? What about pantyhose? I wear them almost daily. I have some bras that aren't silky per se. Are dresses, blouses and skirts OK?"

But I could tell that Miss Priss was launching an investigation here. She had to get to the bottom of this crossdressing issue, and she was intent on how I answered. I figured I'd stall for time and fall back on known issues.

"I told you I dressed up for Halloween..." I don't think I had told her about the extent of my underpinnings, but now I was essentially admitting to the dread "women's silky underwear."

"Yes you told me about that..." Her tone said she was demanding more. "What other times?"

"And I wore them the night before..."

"You did?" She was beginning to become alarmed.

"Yes, of course, we had to see if everything fit, so I had to try on all the underwear, too." Again another admission with "all the underwear." Let her imagine what that meant. As in, full blown lingerie. As in "WOMEN'S SILKY UNDERWEAR!!" She didn't quiz me about the details. I wished she had. I would have given her details about the lace underwire bra and the satin panties with the lace at the leg openings.

She remained on task, "Okay, other than that?"

"Well, I told you about wearing pantyhose. I guess you could say they were silky."

She quickly returned, "Other than those times, have you worn women's silky underwear?"

Time to bail. She isn't going to ever accept it in any way, shape or form.

"No." I lied.

"Why this concern about silky underwear?" I asked.

She explained, "Well there are men who do that."

Yes, I know. I remember my girlfriend in high school explaining that fact of life to me. She gave me one of her slips to help me with a made up hazing thing where I supposedly had to dress as a girl and wear girls underwear.

I never brought up the topic with Cindy again, and I knew we were done. I wasn't going to get a sympathetic giggle out of her. She wasn't going to accept me in panties.

Ever.

The Jackoff Show

2010-09-22T15:57:00.004-04:00

Before much of what I've written about previously happened, I came out to two girls named Jill and Tracey. We were just friends and would pal around together, often going out to dance. Jill was a lesbian, not necessarily butch but she never really wore feminine clothes. Jill had the hots for Tracey. Tracey was very feminine, girly, and mostly straight although later she "dated" other girls. I came out to Jill first. By coming out, I'm referring to my crossdressing. I guess because she's gay I figured she would understand, and she did. We often went out for drinks, and we would notice the same women together. Over time, there were other aspects of my sissyness that I would reveal to her.

While we had become close friends, Tracey had no interest in me romantically. She was younger than me, and she had boys that she would date. We often talked, and she confided in me about them. I guess it was a form of cuckolding to hear about her dates. I tried to encourage her to give me all the details about what she did with her boyfriend. I secretly wanted her to tell me how he fucked her real good so I could know that I couldn't provide her with the satisfaction her boyfriends gave her.

Somewhere along the line, I told Tracey about my crossdressing, too. Jill was a bit of a gossip, and I figured she had told Tracey anyway. She was fine with it, and we'd often talk about clothes and things, just like two girlfriends. The three of us would often hang out at my place before or after dancing, and I'd often relax into something more comfortable. They both thought it was cute that I'd be wearing girls jeans. They knew I wore feminine underwear most all the time, and they'd see my pantyhose on my ankles or they'd see my bra through my shirt. It was fun to hang out with the girls. Sometimes they'd gently tease me about what I was wearing.

Jill was a bit of an instigator in trying to get things naughty and sexy. My theory is that Jill thought that if everybody got turned on, maybe she could get into Tracey's pants. I also found Tracey attractive, so it was a weird triangle.

Once, Tracey ordered a nightgown as a gift from one of my many lingerie catalogs. When it arrived at my place, Jill teased and suggested that maybe I should model it for them. Tracey agreed, and I went into my bedroom, put the nightie on over my pantyhose, walked shyly out into the living room and did a couple twirls for them. I was going to take it off right away, and they both encouraged me to leave it on for awhile. This was very arousing, wearing a silky full length nightgown and pantyhose in front of both of them. After some time, I was standing in kitchen talking to Tracey when Jill came up behind me and pulled up the nightie above my waist. Tracey stood there grinning while looking at my very hard dick encased in control top pantyhose. After about 20 seconds (seemed like an eternity), I acted embarrassed and pulled the nightie back down.

Over time, little teasing events like this eventually led up to one night in particular when Jill and Tracey asked me to put on a little lingerie show for them. "We want to see more of your collection," they said enthusiastically. It was almost as if they had schemed this. Since they had seen me in a nightie before, I put on one of my own and modeled it for them in the living room. “That’s OK, but let’s see something sexier!” My next trip out of the bedroom was more revealing. I have tons of stuff, so it could have been a very long night. Each time, they encouraged me to wear more and more revealing things for them. I thought I had reached their limit by wearing sheer panties, but they were trying to goad me into the full monty. So I finally came out wearing a bra, garters and stockings and my only pair of crotchless panties.

“That’s much better!,” they gleamed. I was actually embarrassed now, and I felt objectified as a woman would be exposed in front of group of men. They had me walk around for them, and whenever I tried to cover my dick, they told me to take my hand away. I was sticking straight out, and after a short while, I started to lose my hardon. “Don’t let it go soft!” Both of them were enjoying looking at my hard dick. I stroked it to get it hard again. “Yeah! We want a REAL show now!” I couldn’t believe this. I was standing in front of these two women wearing sissy clothes and rubbing myself.

One thing I learned rather quickly is that it is very difficult to maintain an erection in front of an audience. They were clearly enjoying the show, and they made it clear they wanted to see me masturbate in front of them. I felt embarrassed stroking fast as I normally would, and yet it felt so sexy to stand in front of them stroking while they grinned and watched.

I knelt on a stuffed chair and tried to concentrate on the feeling. Eventually, they turned their attention to a music video on the TV and gave me a bit of a break from the performance anxiety I was obviously exhibiting. I was relieved for the break but felt puny because I couldn't entertain them enough to keep their attention from the TV. I felt like the little boy wanking in the corner while the adult girls watched TV, ignoring me.

After what seemed like a very long time with them looking away, I finally got up to the edge, and started making noise like I was going to cum. They returned their attention to me. I’ll never forget the amused look on Tracey’s face as she turned her attention back to me smiling and watched as if I was an entertainer.

I started to get nasty. “I’m gonna fuckin’ cum!” Tracey grinned and coyly replied, “Yeah, fuckin’ cum.” I moaned and started to scream as I shot my wad. I felt as though I needed to show the goods, so I came proudly into my hand while they watched the puddle build. Both of them laughed as I shuddered and gave out that last sigh. They finally gave me a round of applause, and I must have turned bright red. The inevitable post-orgasm shame of wearing the clothes came over me, and I was in a hurry to run back to the bedroom and get more decent.

When I came back, they both told me it was great fun for them. I was still a bit embarrassed. Tracey asked, “You really like to masturbate wearing women’s underwear, don’t you?” I admitted I did. “You obviously enjoy it!” The rest of the night was light. They assured me they enjoyed the show and didn’t make me feel like a complete pervert.

Believe it or not, dear sissies, this really did happen. What may be even harder to believe is that there is a Part Two to this story. Sorry this has taken so long to write, but now that I’ve set the stage, hopefully I can write the second half a little quicker.

Do You Cum Like a Girl?

2010-09-01T13:35:00.004-04:00

Whenever I play with my little clit, I moan and whimper like a girl. One time on a phone sex call, and the domme said, "You cum like a girl!" Then she proceeded to mock me in an obviously faked orgasm in the same tone. "Oh my! Oh my! Oh my!!!" It only served to make me even harder and jack off even faster, whimpering all the more and cumming like a girl while she laughed at me calling me a loser.

So, do you cum like a sissy girl?

Putting On A Show

2010-02-18T09:56:00.003-05:00

I once dated a nurse named Toni. As I think back on it, I’ve dated a lot of nurses, and I’ve found them to be pretty open minded and some downright kinky. I’ve written about Carla who was a nurse. After our first overnight encounter, she gave me a pair of her panties to wear home, and thus begun a long, kinky relationship.Here are the posts from that relationship:

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carla.html

http://sissyhumiliation.blogspot.com/2008/02/carlas-first-lesson.html

http://sissyhumiliation.blogspot.com/2008/02/house-dressing.html

http://sissyhumiliation.blogspot.com/2008/05/carla-takes-me.html

Toni was a real go-getter. After our first date, Toni was stripping of her and my clothes and fucking on the couch in the basement .

I revealed to Toni pretty quickly that I was a crossdresser, and on the second visit to her condo, she gave me a tour of her underwear drawer. She showed me all the matching panties and bras that she had explaining that she always wore matching things under her clothes. Picking out a pretty pair of silky panties, she handed them to me and said I could borrow them. She thought it was sweet that I would be wearing her panties. I was already wearing a pair of my own, and she knew it.

The next day, we were talking on the phone, and I told her I was hard as a rock wearing her pretty panties. Toni was amused by all this. The real fun came when I returned the panties to her several days later. I had laundered them, and put them on the kitchen counter. She asked me how I liked wearing them, and I told her I enjoyed the silky feeling of her panties against my cock. “Show me,” she said. “Rub yourself with them.”

I unzipped my pants and wrapped her silky panties around my cock. I started to stroke myself with them, much to her delight. I was getting visibly turned on as I continued to stroke myself. “Cum in them! I know you’ve been wanting to!” I quickened my stroking as she watched with an amused look on her face and her hands on her hips. She said, “I’ve never had a boyfriend jack off with my panties.” Well of course she hadn’t. She’d never dated a sissy before.

I felt a bit objectified standing before her in the kitchen masturbating as she watched with a sly grin and her hands on her hips. Just as I was getting close to cumming, she cheerfully said, "Squirt, squirt, squirt!" That did it. I let myself go and came loudly while Toni stood there watching.

“Did that feel good, honey?” she purred. I nodded. “Let me see…” She wanted me to open the panties and show her my load. “Ooooh… good boy…” The tone of her voice made me feel small, like a little boy. Good little sissy made a puddle.

But this hadn’t been the first time I had put on a masturbation show. I’ll tell you about a show I put on for a small group of women.

'Tis the season...

2009-12-14T10:49:00.003-05:00

What kind of a sissy would wear this in public? With a butt-plug?!

Those aren't bike shorts!

2009-11-20T10:23:00.005-05:00

JamieLin has been sharing his escapades being outside running in his girl clothes. He's such a naughty boy. It's so exhilarating to be out in a public or semi-public situation wearing feminine things.

My version of the sissy workout wear scene is to wear this Rago pantygirdle as bike shorts. I've worn it with a tunic style top (somewhat feminine) along with ankle socks and sneakers. The first time I wore it outside, I felt naked and vulnerable. I thought to myself, "I don't believe this! I'm walking around outside in a girdle!"

But it's amazing how much this little getup can look so normal, especially at a distance. I've worn it in stores, walking down a street and through a mall. I even walked through a hotel lobby. Nobody even made a second look.

Of course, if I want to be exposed for what I am--a sissy--then I can let the tunic top ride up and expose the tummy panel on the front. That's gotten some reactions that made my face red hot.

Sometimes I like to really push the edge of the envelope. Lace anklets offers no escape or cover-up.

Halloween Shopping

2009-10-30T13:49:00.003-04:00

In a couple earlier posts, I told you about my friend Anna who witnessed my humiliation with an escort and had cucked me with her boyfriend. Anna had introduced me to a friend of hers named Renee who was also an escort and familiar with the humiliation of sissies. In a couple earlier dates, she had paraded me around a shopping mall having me try on bras at Frederick's and trying on high heels at a couple different shoe stores.

This particular night took the cake and was one of the most embarrassing things I've done. It was a couple nights before Halloween. First I called a store (I think it was called Fashion Cents) and asked if I could try on girls clothes because my girlfriend was making me dress up. The clerk I talked to was very enthusiastic about it and told me to come in and they would be happy to help.

I was wearing back-zip jeans and platform sneakers and a slightly feminine top. When we walked into the store, I stood there sheepishly while Renee went straight to the counter and told the girls who we were. THREE of the clerks walked out with Renee, and they were smiling and giggling. Renee told them I needed a short dress, something kinda slutty. One of the girls noticed my jeans and pointed out the back zipper to the other clerks. They thought it was funny and sweet at the same time that I would wear what my "girlfriend" told me to wear.

Renee had with her a bag of underwear and shoes that I had prepared. After she selected a couple dresses, skirts and blouses, one of the clerks pointed us to the fitting rooms. Before we went in, Renee stood there and started pulling out the various items for all to see and handing them to me. "Here's your bra. Here's your pantyhose. Here's your little lacy panties. Here's your high heels," etc. in a voice loud enough to be heard by the others. Standing about ten feet behind her is one of the clerks taking it all in and smiling ear to ear. My face was red hot.

We went into the fitting room and Renee had me put on all my underwear while she laughed and called me a sissy, again loud enough that I'm sure the other girls in the store could hear. She would laugh and say things like, "Oh my GOD! Looks like you ENJOY wearing panties!" I could hear them giggling outside.

Renee had me step outside of the fitting room so they could see me in this micro-mini stretch dress. They loved how my shaved legs looked in my pantyhose and high heels. She had me put on a short denim skirt with a very sheer blouse and then she paraded me around the store looking for other things. I was so embarrassed trying to cover up my front so my lace bra didn't look so obvious. By this time there were other young women in the store and they were staring, grinning and giggling. I was totally humiliated and totally turned on.

Back in the dressing room, Renee thought up something that would make the whole scene even more embarrassing. She took one of the dresses to the counter and asked them to the remove the tags because she was going to have me pay for it and wear it out of the store. She said she was taking me over to her girlfriend's house so she could see her sissy boyfriend.

She came back and handed me the dress. She gave me my wallet, bundled up all my own clothes, and walked out. I tried to protest, but she just said in a loud voice, "Pay for your dress, and let's go!" Then she walked out of the store, leaving me wearing the clothes I would have to pay for and wear out of the store.

I waited in the fitting room for a minute or so looking at myself in the mirror. Here was this sissy wearing girl clothes, nylons and heels. No wig. No makeup. Just a pathetic sissy. I sheepishly walked out of the fitting with all the clerks and some of the customers grinning. My hands were shaking as I handed the clerk at the counter my money. She was saying that she wanted to dress up her boyfriend like this sometime. A very attractive woman customer at the counter gave me a very condescending smile and said, "It sucks to be you, doesn't it?!" I just said, yes, and she laughed.

As I walked to the door, I was saying, "I can't go out like this!" About that time, two teenage girls walked in. Both stopped in their tracks, looked at me, and laughed. One of the clerks was at the door, and asked me why my girlfriend was making me do this. I sheepishly said, "She caught me trying on her panties a couple times." The clerk gave me a mock scornful look and said, "Well, then, you deserved this, didn't you? Shame on you!"

As I hit the door, one of the clerks called out, "Come again!" She didn't know how close she was to the truth.

The store was in a strip mall. I made a bee line for my car, where Renee was waiting laughing her ass off. I heard some laughing and an "OH my God!" behind me as I tried to run in my high heels. By the time we got in the car, I was on fire with embarrassment. She drove and kept telling me what a sissy I was and how all the cute young clerks and women in the store knew what a sissy boy I was. I pulled down my pantyhose and panties and started wanking while she said, "That's right, stroke your little clitty for me, sissy fag! Moan and cum like a girl for me. Let me hear your cum like a girl. Cum in your hand so I can watch you lick up your little messy for me!" I whimpered and cried and dribbled into the palm of my hand. Renee quickly commanded me to lick up every last drop while she called me a loser. I was drained and totally humiliated.

But it wasn't over. When we got back to my room, she put on my strapon and made me suck on it while she stood in front of a mirror. She told me to look at myself in the mirror so I could see the sissy cocksucker. Then she gave me a very sound spanking until I cried. Finally, I was made to "walk the wall." She had me position myself on the bed with my ass against the headboard and my feet on the wall. I had to raise my hips up over my face so I could cum in my mouth. She again had me suck her cock and wank while she derided me. I dribbled a load into my mouth and on my face.

I still get off re-living that night.

Sissy Captcha

2009-10-02T09:39:00.002-04:00

Every time you post on these blogs, you have to go through the "eye test," or CAPTCHA to qualify yourself as a human and not a spambot.

This morning, I was checking the comments of my last post, and there was a most appropriate CAPTCHA image for this blog:

Well, of course!

Aren't these cute?

2009-08-31T10:50:00.007-04:00

"Slip them on for me, won't you?

"Yes, they look just darling on you.

"Now I want you to kneel on the edge of the bed while I lube up my black strapon.

Put your elbows on the bed, dear. I'll be very gentle with you..."

Here, put these on!

2009-06-02T17:00:00.004-04:00

Here, put these on for us. Aren't they pretty?

Yes, they're totally sheer so we can see your little thing through it, and we can watch it get hard. Look! It's getting hard right now as you pull them up your legs.

All the girls are giggling now. We can see your shame.

Oh! It's getting harder now that you can feel the stiff, sheer material. It's poking straight out and making a little tent, isn't it?

It's so funny! Your little thing is sticking out! OMG! We're all laughing.

Awwwww, don't cry.

Fetish Focal Points

2009-03-25T10:42:00.010-04:00

There are some things that just slay me.

A beautiful woman wearing silky pants probably over pantyhose. While most normal guys are looking at her face and her tits and trying to start a conversation with her so they can screw her, I'm trying to get behind her just to see that zipper and the darts. I want to wear her pants.

Hey, can I wear your clothes while you fuck that guy?

I can get off just looking at that zipper on a woman's pants.

I have several pair of women's pants that zip in the back or the side. There's just no mistaking the look, and when women see them on me, they know immediately. "That guy's wearing women's pants!" Then the giggling starts, and I'm exposed. Why would he be wearing pants like that? Does he know he's wearing women's pants?

Innocent girls modeling foundation garments. Takes me back to the Sears and Penny's catalogs. This was the mysterious world of women's underwear that was so magical. To see a real girl in just her underwear was nigh to impossible. A good girl wouldn't let herself be seen this way.

People will sometimes have dreams where they are naked in public. Walking nude in front of other people. The dream symbolism is that they are exposed, their inner selves are completely shown for all to see. Quite often, the other people in the dream don't notice or don't care. In the dream, their own discomfort is the real issue.

I once had a dream where I was in women's underwear in public. Wearing a bra, pantyhose, and girdle. I felt so exposed and vulnerable, like this girl would be if she was suddenly seen by strangers. I was walking down the hallways at work passing people who didn't know me and some people. This was my nakedness. For me, being in women's underwear is more naked than naked.

The gussett. You can't get past it. You're not enough of a man to get past it.

I was the little creep in school, looking up girls' skirts.

Go ahead and look, loser. That's right, get a good look. You'll never get it. Look all you want, and wank your wee-wee for me. Jack off while the other girls in the office and I laugh at you.

You need to be penetrated!

2009-02-03T20:24:00.004-05:00

Before I return to the Nashville stories, I just wanted to share a memory from my early days when I was visiting local massage parlors on a regular basis. There was one girl I visited regularly who knew how to treat a sissy.

I remember one time when I was waiting for her to come in the room. I was standing there in my bra, pantyhose and heels when she came into the room in her usual cheerful mood. She was wearing a silky dress over pantyhose, bra and heels. I started to feel her up through the dress and said excitedly, "You don't have any panties on under your pantyhose." She immediately rubbed my dick and said, "You don't either!"

I told her how much I liked her silky dress. "You like my dress, Mikel?" She quickly started removing it. "Since you're so damned interested in my dress, let's put it on you! Yeah! You wanna wear it, don't you? You want to wear my dress!" She laughed as she was putting it on me and buttoning the buttons. "Yeah, just look at you now. You have your little bra and pantyhose and pumps on, and now you get to wear my dress! Just like a real girl!" I was elated. She was just excellent.

She really turned me on to being poked in the bottom. It was common at this place to get a hand job, and one of the first times I was with her, she had me all lubed up and was masturbating me when she deftly slid her finger right up my hole. "OH MY!" I squealed. She would laugh at my reactions. She made me feel so cute and girly. "OH MY!!" she mimicked me back.

One time, she made me get up on all fours on the massage table. She finger-fucked me with one hand while she was milking me with the other. I was squirming and wiggling as I moved around like a prom date losing it for the first time.

"You need to be penetrated!" she said firmly in my ear. She was absolutely right. She knew sissies and their need to be penetrated. To be taken. To experience the fullness of what it feels like to be fucked like a girl. Yes! I need to be penetrated! Fuck my little pussy bottom! Penetrate me!!

I was in a frenzy. I came so hard. I exploded while she laughed and encouraged me to let it all out for her. After I spurted the last, she plunged me one more time. It was as if to drive home a point.

She would have such a delighted look on her face as I felt so vulnerable at being finger fucked.

I need to be penetrated!

Nashville Part III

2009-01-27T09:11:00.003-05:00

Again, sorry for the delay in trying to get posts written. I wanted to pick up on my Nashville stories. To review, I had been completely humiliated by a professional domme from an escort service in front of my new friend Anna. This had been Anna's first exposure to humiliating men, but she really enjoyed it. The next night at a group dinner, she openly told everyone about my scene of dressing up, being spanked, licking up cum, etc. Read the posts below for more details.

I had been doing some humiliating sissy shopping the next day and was just coming back to my hotel when a car pulls up and parks next to me. Out come Anna and a man. I started to get panicky. It turns out he was her boyfriend, and she brought him along to have some fun. I had this sinking feeling because I was afraid that she had brought him over to have me suck his cock. Besides, I've never really gotten into these scenes with other guys, and I was already embarrassed that she had told me about what I like to do. Dan shook my hand and was pretty normal.

We went into my room, and after a short while, Anna told me they wanted to see me put on my sissy things. I sheepishly got out my bag and started selecting some things to wear. Anna and her friend sat on the other king-size bed and watched as I started to strip and put on my underthings. Anna told me that Dan had a particularly interesting talent: he could cum repeatedly. I was a bit curious about it, and she started playing with him and sucking his cock in front of me. His cock was about average size.

After getting him all worked up, she had him stroke himself to orgasm. After cumming, he kept stroking, and about a minute or so later, he came again! Again he kept stroking, and he came a third time and a fourth. I was utterly amazed any man could do this. By this time, I had my girlie things on, and Anna told me to get out my toys and start playing. It was difficult to act out my sissy side in front of Dan, but I was starting to get prissy as I slid in the butt plug. Anna laughed and said, "See, he's a sissy pantyboy! He likes that plug in his cunt." Then she told me to start sucking my 10" dildo. Anna told Dan, "He cums on it and eats it!" Embarrassed, I closed my eyes and started sucking it while she laughed. Dan didn't make too many comments, but I truly felt degraded and like I was on display.

Anna had stripped and got on all fours on the bed across from me. In no time, Dan was in her from behind and was fucking her. I was a bit stunned, and I asked "Oh my... is he fucking you?" Anna smiled big and said, "He sure is! It feels so good to get fucked by a real man!" She closed her eyes and moaned while I, the sissy cuckold, knelt on my bed straddling a pillow with a plug in my pussy bottom. I rode it up and down while I sucked on my pretend cock. All the while Anna and Dan were fucking each other silly.

I eventually started to cum. I whimpered like a sissy and dribbled on the dildo. It's difficult for me to stay in the moment and actually eat the cum unless I'm being dominated. I was overwrought with the shame of being in front of them, and I just laid over on the bed. When she realized I wasn't planning to lick up my mess, Anna snapped, "You lick that dildo clean! Lick it up! Now!" I sighed and slowly put the dick in my mouth. The humiliation was very deep. Here there was a couple watching as I sucked my cum off a dildo.

Anna cooed in her southern voice, "Does that taste good, Honey?" I quietly nodded. She laughed and said to Dan, "See, he's a sissy wannabe cocksucker." By this time, I was terrified she was going to have me do something really disgusting like lick Dan's cum out of her pussy or suck his cock clean. It was enough cuckolding to have them fuck in front of me knowing that I wasn't going to participate.

Thankfully our encounter didn't last too much longer. I cleaned up and put regular clothes back on and they headed out. Anna would return later. Dan was married, and they had been having this ongoing affair for some time. I was their entertainment for the evening, and I certainly felt like an object.

What a pathetic sissy. Watching a couple fuck while they watched me fuck my pussy bottom and my mouth with sex toys. I could imagine their drive back together: him asking her, "Where did you meet this queer?"

There's more to come on the Nashville story. Stay tuned!

Don We Now Our Sissy Apparel

2009-01-08T09:54:00.006-05:00

I'm always jealous of what girls get to wear. This time of year, now that it's cold, I see a lot of cute girls wearing Ugg style boots with skinny jeans or leggings. I have a pair of boots like this, but I'm trying to find the perfect pair of boots. They have to have that little line of fur at the top and look girly, like in the second picture below.

I see cute women wearing them, and it's like not wearing any pants or a skirt. How naughty! You wouldn't go out like that otherwise, but somehow, just because the material is just a little thicker than tights, they can wear them without anything. Of course, many women are a bit more conservative, and they wear a longer top or coat.

Of course, I have lots of leggings and have had many escapades wearing them and getting giggled at in public. It makes me feel so sissy and vulnerable wearing thin leggings under a short tunic top or a coat in cold weather. Since adding the boots, it gets even more giggles and looks than when I was wearing more gender-neutral shoes.

These boots with the laces and fur at the top are so prissy with leggings.

Another twist on leggings is wearing black Danskin tights. Normally, they would be too sheer, but I will wear control top pantyhose under them. The effect is perfect. At a distance, they look like leggings (which is sissy in itself), but up close, you can see the image of the control top panty portion through the tights. If my top is short enough (I've even done this in the summer), you can see I'm wearing pantyhose.

One more than one occasion, this look has drawn the classic "oh... my.... god..." reaction from cute hot girls. The snickers start up, and then my face starts burning. Once, I heard a girl from a distance: "What a fuckin' GIRL!" followed by uproarious laughter from her friends.

I'm so jealous of her. She gets to walk around in just a shirt with no pants or skirt.

I would love for a group of three hot women out shopping together to catch me in my sissy leggings. Such hot babes would think the sissy boi was so pathetic.

The one on the right just slays me. She would look great wearing a strap-on dildo.

What a cutie. I wish she'd invite me over and put this outfit on me. Then she could have me suck her boyfriend's cock while she laughs.

Nashville Part II

2008-11-15T08:46:00.002-05:00

This visit to Nashville was just before Halloween. I planned to get as much out of it as I could by doing some sissy shopping in a town where I wasn't likely to be recognized. I went to some dancewear shops to look for some thong leotards and tights. I visited a couple stores and tried on and bought some sexy items.

Anna was going to have some more fun with me. The next night, she invited me along to dinner at a pub where members of this online swing group were going to meet. I wore regular clothes and was a little self-conscious because I was introduced as "Pantyboy," my online handle with this group. Some of them might have remembered my bio that stated that I liked to wear sissy girl things and French Maid uniforms and be humiliated with a strapon, but nobody really said anything about it.

At one point, Anna got everyone's attention and announced that everyone was invited to my hotel room to watch me put on girlie clothes, get spanked while wearing a butt-plug and have to eat my cum. She basically described the whole scene from the evening before in front of everyone at the table. I was red faced and humiliated, especially with men hearing the sordid details. Nobody took her up on the offer, and I felt a little like a little freak.

There was one particularly hot woman there with her husband. They were swingers. She was dressed in an sexy tight dress with black pantyhose and no panties that I could tell. I had been eying her. She did say, "Sorry we have other plans. It might be fun. Maybe I'd have you suck off Jim (her husband). Anna chimed in with, "Oh, he'd love that!" Nothing came of the evening other than I had been humiliated in front of group of about 25 men and women.

The next day I did some more sissy shopping. A lot of times, I'll call ahead and ask if it's OK for me to try on feminine clothing. I also use the call to set up a sense of embarrassment ahead of time. I told the clerk on the phone at this one store that my girlfriend was making me dress up as a girl for Halloween. I could tell she thought that was amusing. She said I was welcome to come in and try on dresses. I arrived carrying a bag with bra, pantyhose, a girdle brief, and high heels. I told the girl I was supposed to make sure it all fit right. She and the other clerk thought it was really funny that I was going to wear everything. I told her that my girlfiend had made me try on the bra and panties at Frederick's. They were laughing at the stories I told her.

They helped me pick out a couple dresses and put me in a room in a closed-off section of the fitting area, so I had the whole side to myself. After I put on all my underthings, I tried on the first dress. They were asking me through the door how things were going, and after I had it on, they told me to come out and show them. "You look great!" she said with a big smile, and she called the other clerk over to see me. I was acting very embarrassed having to wear a bra, girdle, hose and heels. I was walking awkwardly in my heels. I got a lot of giggles as I tried to adjust this very short, tight dress so that the panty line of my pantyhose didn't show.

After trying on two other dresses, with their help I decided on a grey and red houndstooth dress that was obscenely short. Both of them were having fun with me by then, and one said, "You'll have to be careful not to let boys see your panties." They both laughed. I made a comment that my girlfriend had me wearing panties a number of times. The other said, "Better be careful you don't get used to it. This could become a regular habit!" Inquisitively I asked, "You mean if I wear panties too often?" She replied, "Yep, you could start liking it." I said, "Well, I have to say they do feel very nice." They giggled as they rang me up. I thanked them as I left, and they were laughing and saying, "Have fun!"

Nashville

2008-08-07T11:07:00.000-04:00

Get ready, bitch

I had met a lady online named Anna. She was a little older than me and lived in a Nashville, which is about five hours from where I live. She was part of a group that did a little swinging, and while she had encountered other sissies online, she'd never really met any in person, and she was a little intrigued by it. We talked on the phone a couple times, and I told her some of the things I did. She thought it was pretty funny and she wanted to meet me so I made plans to visit.

Once I checked into a hotel and got acquainted with Anna for awhile, I checked into local adult entertainment in the phone book. I've utilized the services of escort girls to come to my room and engage in some sissy humiliation sessions with me before, and we thought it might be fun if I had one come over to do a session with Anna present to just watch. I called one of the services and told them I was a crossdresser looking for some light domination. A woman named Kathy called me back and I told her I had a female friend who just wanted to watch while she dominated me. We agreed on a price, and she headed over.

I showed Anna some of my sissy outfits and modeled some of them while she giggled at me and called me a "sissy cunt" in her sweet southern voice. I was dressed in my bra, pantyhose and high heels when Kathy knocked on the door. I covered myself and let her in. Kathy was very pretty and very nice and professional. We worked out some financial issues, I explained exactly what it was I wanted, and she called in to the service to check in.

Kathy was wearing a skirt with pantyhose and no panties as I requested. I was behind her peeking up her skirt, and Anna was sitting in the corner, giggling, calling me a naughty boy. About that time, Kathy hung up the phone and turned around, catching me. "What the hell are you doing? Get up! What are you doing in these clothes?" I was still smiling, looking over at Anna and her giggling."

She got serious

Kathy grabbed my face and pointed it at hers. She was quite serious. "I asked you, what - are - you - doing - in - these - clothes?" Her voice was stern but she didn't yell.

I was like a little boy caught being naughty. "I... just... wanted... to see what... they felt like?"

Now she lowered her voice in a more intense kind of quiet, almost a whisper. "Oh you did? You wanted to feel what it was like to be a girl? Is that it? You want to be a girl?"

"No, I just wanted to feel the clothes..." I tried to explain.

She quickly grabbed me hard by the wrist. "I'll give you something to feel, little girl. C'mere"

She marched me over to the bed, sat down, quickly yanked my pantyhose down, and pulled me over her lap. Then she started smacking my bottom... HARD!

Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack!

"Owwww!" I tried to put my hand over my bottom.

She quietly and sternly commanded, "Put your hand down."

She started it up again. Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! Smack! She would alternate from cheek to cheek.

"Please!" I whined, "I promise to be good!" I again tried to cover my bottom."

"I said put your hand down. Now!"

Again and again we went through this. Anna later told me she couldn't believe how red my bottom had become. I'd never been spanked this hard.

Change of clothes

"Now get up!" she said quickly, "Get those clothes off! Now!" Again, she never yelled, but it was clear she was in charge. I took off my heels, pantyhose, and bra. I was rubbing my bottom with both hands. She again grabbed me by the wrist and marched me across the room.

"You wanna be a fuckin' girl? Let's make you into a fuckin' girl and you can really see what it feels like."

I protested that I had learned my lesson and I didn't want to do it. Kathy told me to shut up while she put a black padded bra and thong panty on me. Next came a black, boned waist cincher with garter. Then she had me sit on the edge of the bed while she put black stockings on my legs. The whole time she was telling me what a hot girl I'd make and how I evidently like wearing girls clothes or I wouldn't have such a hardon. I tried to deny it, whimpering like a pussy boy.

Finally she put my 5" stiletto patent leather pumps on me and had me stand. I stood and covered my bra with crossed arms like a woman would if she had been suddenly discovered undressed. This infuriated Kathy, "Put your hands down! You wanna be a girl. Let's see you be a fuckin' girl. Walk around for us, bitch. " I minced and teetered around the room.

Kathy looked over at Anna. "What do you think? Do you think he likes being a girl?"

Anna came back with a wicked smile, "He's a sissy cunt!"

"He IS a sissy cunt!" Kathy answered. "Now I'm going to spank you again."

"Nooooo!" I whined.

Round two

Again, Kathy grabbed me by the wrist like a child and pulled me across the room, sat down and put me back across her lap. I was already smarting from the first assault on my red ass, and I didn't think I could tolerate much more. Before she even started, I was trying to cover my bottom. She repeatedly ordered me to put my hands down as she started over and over. It only made it worse. Kathy spanked and spanked harder than the first time. It hurt like hell.

I looked over helplessly at Anna, "Please help me. Make her stop!"

Anna, snapped back, "Shut up, you fuckin' bitch!"

And now, your mouth

Kathy grabbed my 10" dildo with balls and held it in front of me. "Now you can see what's it like to suck cock."

"No! I won't!" I pouted.

Kathy answered, "You want me to spank you again?"

I looked over at Anna and reluctantly put my hand on the dick and started licking it. Anna just started laughing, "I don't believe this! You are a fuckin' sissy cocksucker!"

Kathy pushed my head on the dildo and had me bobbing up and down on it as she degraded me. She had me lick the balls and lick up and down the shaft. I was stroking myself as I did. "You really like that, dontcha bitch?" I just quietly sucked the big cock while Anna laughed.

And now, your sissy ass

With that, Kathy took the butt plug laying on the bed and started squirting it with KY jelly and told me to turn over on the bed.

"Oh, please don't do this. I'm really sorry. Please! I won't do it anymore!" I pleaded with her.

Anna jumped in, "He wishes he was a real woman so he could take a real dick inside him."

"I do not!" I answered back like a baby brother. Kathy again told me calmly to turn over as she held the greased up plug in her hand. I begged her not to fuck my pussy.

I continued to beg Kathy as she turned me over. I was now facing Anna who had a menacing smile on her face, and I was now being overcome with humiliation. Anna was going to get to see the look on my face as I was going to get ass fucked. As Kathy slathered the plug up and down my crack with cold KY, I got a disgusted look on my face. Anna laughed and asked in her cute southern voice, "Are ya gettin' your pussy buttered up, hun'? I just let out a disgusted moan.

With that Kathy just jabbed the plug up my ass. She was not at all gentle, and it HURT like hell! I protested, and she told me to be quiet while she jabbed me again. I tried to reposition, and Anna asked me if I was getting my cherry popped. Finally Kathy got it in me and started stroking it in me quickly. She got me up on all fours so I could continue wanking with the dildo in my mouth. Anna just laughed, "I do NOT believe this!"

They were talking to each other and calling me a sissy cunt. I wimpered like one while Anna just laughed. She'd never seen such a display and was truly enjoying the show. By this time, Kathy had called Anna over and was standing next to us. At one point, she was given the dildo to push in and out of my mouth. I think she rather enjoyed the control of fucking a man in the mouth with a big cock and humiliating him in this way.

A little cuckold, just for good measure

At one point, I was wanking and looking at Kathy's pussy through her pantyhose, a view I particularly love. She stared at me back and said, "Look at it!" Then she pulled her pantyhose down. "Go ahead! Look at it! Wank your little dick and look at it! You will NEVER fuck it because I don't fuck sissy boys."

Anna chimed in and said, "He wouldn't be able to do much with what he's got anyway!"

Kathy contined her comments to me, "Yeah, but get a good look at it and wank your little dick, sissy cunt! Sissy cunt! Sissy cunt!"

By now they both kept calling me "sissy cunt" over and over again in unison. It was very belittling and humiliating.

It wasn't too long before I had gotten so worked up that I was about to lose it. "I need to cum," I whined. Kathy sassed back, "Awww, she needs to cum." She took the dildo and held it in front of me. "You know what you have to do then, don't you? You have to cum on this big cock and then you have to lick it clean for us."

"NO!" I whined back like a sissy.

"Then you don't cum. It's as simple as that. You want to cum, you have to cum on the dildo and lick it clean for us, you understand? Are you going to lick it up for us or not? It's your choice. You can cum or not cum, but that's the only way you're going to cum. Don't stop stroking it, sissy cunt! Girls have to eat cum, and you want to be a girl, so you have to eat cum!

Anna was laughing and coaxing me, "Come on, sissy cunt. Shoot your little dick and lick it up."

Kathy was holding the dildo out in front of me. The butt plug was burning in my sore pussy bottom. I couldn't hold it out any longer. I screamed out like a little bitch as I bounced up and down on the butt plug.

Anna reacted, "Oh my god, will you listen to this? He even cums like a girl."

I came and screamed and came and whimpered and came some more. I shot all my sissy cum all over the big hard rubber dick being held out in front of me.

"Did you get it all out, sissy cunt?" Kathy asked.

"Yes," I whined.

She quickly put the dick in my mouth. "Clean it up! Now!"

Anna was laughing again, "Look at this! What a fuckin' cum eating bitch!"

You missed some

I dutifully licked it all up and sucked the dildo clean. I wanted to be a good girl for them and show them I could do it. I slurped the length of it and sucked it completely. By the time I had finished licking it clean that aversion to eating cum started to sink in combined with the shame and humiliation. I looked at Anna who pointed to a big glob of cum on the sheets and said, "You missed some." I let out a moan of disgust. She laughed hysterically as I starting licking it up off the sheets.

Kathy said to me in a motherly tone, "Mama's proud of you 'cause you ate all the cum. You did a good job like good girl." Then her tone of voice changed back into more of a warning, "But every time you put those clothes on, you're gonna get fucked in the ass, and you're gonna have to eat the cum again. You understand, Sissy?"

I nodded in total shame.

Kathy was getting dressed and told me what fun the session was. Anna said she'd never seen anything like this, but she'd learned a few things.

So had I.

Thanks for Enduring the Last Post

2008-07-19T10:59:00.002-04:00

For those of you who read it, thanks for enduring the last post. It was very long. I had no idea how long it really was until I posted it, and I couldn't figure out how to break it into parts.

I promise to keep my next couple posts to be much shorter.

Coming soon...

My Trip To Florida Part II

2008-07-03T11:29:00.003-04:00

I had a couple days before I was to visit the club and see Kelly. They were many mini-humiliation events I may come back to later. But this is about the club experience. I apologize for the length of this writing, but this was pretty intense.

When I finally got back to Ft. Lauderdale, it was a little late in the evening. I had mapped the address to the club. I didn't want to get there too early. I was also a bit shy about showing up in my sissy attire a club like this, even though I figured it would be friendly to someone like me. I started to get ready for the night. I put on a padded bra and black shiny tights. Over it, I wore the thong leotard I bought at the dancewear store where I met Kelly a few days earlier. It was burgundy, with a cowl neck and long sleeves. My come-fuck-me pumps with a 5" heel made me look like a complete sissy slut.

I put on a bit of make-up and lipstick. But that was it. No wig. I don't want to pass as a girl. Just the sissy slut boi that I am. Not knowing what I would be able to do at the club, I packed a little bag with my favorite 10" dildo with a suction base, a butt-plug and lube.

It was getting pretty late when I finally got to heading for the club, and I reasoned that a place like this would only be getting started fairly late anyway. I put a jogging outfit on over the outfit and more comfortable shoes so I could leave the hotel without making a scene. Once in the car, I took off the jogging suit and put on the heels and drove in slut mode to the club.

It was located on the edge of a industrial park complex in a somewhat scary area, so I was cautious. When I arrived, the parking lot didn't seem to have many cars parked there. I double-checked the address. There was a small sign at the door so I knew I was at the right place. Nervously checking around, I got out of my car, locked it and headed for the door. It's always makes me feel so sexy and vulnerable when I'm outside wearing an outfit like this.

There was a buzzer at the front door, and my heart was racing as I rang it. I figured I could always jump out of my heels and run in my stockinged feet if I had to. There at the door was a heavy-set woman, obviously a dominatrix, wearing a black leather bustier and a black skirt. She was smiling and happy to see me.

"Hello, come in!" She was looking me up and down as I stood timidly in front of her.

"I'm Mikel. I met Kelly at the dance store the other day?"

"Oh yes! She told me about you! I'm Mistress Jackie. Nice to see you, Mikel. There's no cover charge for boys in drag. Kelly said you'd be in your leotard and tights. Very nice. Very cute."

I was mincing around in front of her feeling very self-conscious as she was clearly checking out my ass. I felt like a girl being ogled. I held my little bag in front of my tight crotch.

"And what have you here?"

"Well," I explained, "I've never been to a club like this, only to a private Domme, and I brought some things with me."

"And what kinds of things have you done with your Domme?" she asked.

She was being very nice as we chatted, and we were alone in the foyer of what looked like a former office. I moved closer to make a confession, "Well, I've been made to suck on her big strapon... and she'll fuck my mouth with it... and she puts a butt-plug in my pussy-bottom... and she gives me some very sound spankings--of course the butt plug always helps make the spankings so much more effective... and then she makes me wank my... little... wee-wee... and has me squirt it on the dildo?... and then I have to lick it clean like it's a real man's cock. It's so humiliating and disgusting, but she says it's good practice."

As I explained the details of my humiliating scene to Mistress, I became more and more sissified, and she could tell by my mannerisms. She nodded and affirmed her understanding of each of the details of it. Then she explained that because this is a public club they could not do anything anal and they could not have any masturbation on the premises. She said I could get a spanking and get my mouth fucked and get the humiliation. "If you're good, I may give you permission to go home and cum onto your dildo and lick it clean, OK?"

"Yes, Ma'am," I answered timidly.

About this time, Kelly came into the room as bubbly as ever. "Hello!

"Kelly, you remember Mikel?"

"Yes! Hello Mikel!" She gave me a light hug. "I was afraid you weren't going to make it. I'm so glad you came! Come on, I'll show you around the club."

Kelly chatted with me a little and took me through the door into what was a mostly empty club. There was another Domme talking to a man. There were a number of other people just talking to each other, but nothing was really going on. I felt a bit self-conscious because I was the only sissy. There were no guys in drag. But nobody really paid attention. Kelly explained that not all that much happens on Friday nights and they were going to close pretty soon. I was glad I got there when I did.

The room had mirrors all along one wall. There was a small stage where scenes were acted out. Toward the back, it got much darker. There was an area that had a cage with bars and rings in the wall. At the very back of the room was a caged contraption almost like a coffin where a man was totally confined. Kelly explained that he's into complete restriction, and that he'd been there all night and would remain there. The other domme went back to check on him.

I chatted with Kelly about what she did there. I wondered if she got into any of the scenes. She just seemed so sweet as to be out of place here. This was just a part time job for her. She just acted as a hostess. She helped with drinks and cleaning up and entertained a little. She was just so innocent.

When we got back to the foyer, Kelly said she'd leave me with Mistress Jackie and to let her know if I needed anything to drink or anything. Mistress explained the tribute system for the club, and we worked that out.

Mistress Kelly pointed to my little bag. "You have your butt plug with you?"

"Yes ma'am" I answered.

"Come over here..." She took me to a little corner. "Put it in, right here, where only I can see... Do that right now..."

I took the plug out of the bag and lubed it up with KY. It was very awkward because I had to pull down my tights enough to slide the thong strap of my leotard aside and then insert the plug. I squatted down and plugged myself in a dark corner while she hovered over me with her hands on her hips smirking at me. I got even more sissified and pathetic, whimpering and saying "Oh my... oh my... oh!" as I pulled up the tights and repositioned the thong strap over the butt plug. I gasped as I stood up. Mistress just laughed as I wiggled and minced on my heels.

She told me to go back into the club and have a seat. I went back to the outer area. The other domme who never introduced herself stopped me on the way and said, "What's your scene?"

I didn't quite understand at first because she said it in a very businesslike manner. I figured she was going to set something up for Mistress Jackie. "Uh... dildo cocksucking, spanking, and sissy humiliation," I replied.

She pointed to a bench. "Sit over there."

I sat quietly holding my little bag and my plug now starting to cause my pussy-bottom to throb. I didn't know if I should get out my dildo. I didn't want to be sucking a strange dildo anyway. Then she walked by several times as if looking for something. I said, "If you're looking for a dildo, I have one..." She got close to my face and said, "If I need your help, bitch, I'll ask for it. Now sit there and shut up."

My eyes dropped to the floor and I sat there like a chastised little girl for what seemed like an eternity. Then suddenly, I heard the heavy steps of high heels on the floor. I looked up and saw Mistress Jackie marching her way toward me wearing a strapon dildo with a giant black rubber cock. "Shit!" I said aloud before she got there.

I sat up prim and proper, stealing scared glances at the giant black cock hanging in front of me. I crossed my arms in front my bosom and nervously tried to shield my eyes from the obscene phallus.

"Have you been a bad girl?" She asked quietly.

I nodded in quick, small, frightened nods, looking down.

"What have you done? she quickly demanded.

I wasn't prepared for a confession. I was going to make up some naughty fantasy of sucking off the boys in the neighborhood when I caught sight of beautiful, innocent Kelly talking to some of the others in the club. My mind went back to when I first met her in the dance shop and I was in the fitting room trying on girlie thong leotards and prissing in front of the mirror and listening to her talk to the shop clerk.

"Well? What have you done? Mistress demanded in a more stern voice.

"Well..." I started out slowly, "the other day when I met Kelly? When she came in the dance shop, I was trying on leotards and prissing in the fitting room... and she was talking to the clerk... and I was listening to her sweet, bubbly voice... and I was playing with myself..."

Mistress' eyes widened, "Oh... you... DID... did you?!" She pointed to the floor in front of me and commanded in a quiet, determined voice, "Kneel." I wasted no time. I had the feeling it would have been better if I had just made up a fantasy confession and left it at that.

"You have fucked up, missy!" She held out a condom in a package. "Do you know what this is?" I nodded. "Do you know what this is for?" I nodded. "Open your mouth." I obeyed. She held the package in front of me. "Hold it in your teeth." I did.

Mistress walked off and returned with a wooden chair and sat down. "Put the condom on my cock."

I was getting so prissy by this time and acting so revulsed by the size of the black rubber cock between her legs. I was saying things under my breath like, "It's so huge and black and disgusting."

"Suck it." She pointed at it and ordered calmly.

"Um... but it's so big and black," I protested helplessly.

She grabbed the back of my head by my hair, twisted it, and pushed my face to it. "I said suck it."

I put my hand around the huge phallus and started to lick the head shyly at first. Then within only a short moment, I was bobbing up and down on it.

"That's what I thought. You are a cocksucking slut. You sissies are all alike. Look at you. You love sucking cock." She let me suck and slurp and moan shamelessly on this giant black prick for another minute or so.

"Get up, slut!"

With a sweep, Mistress Jackie grabbed my wrist and had my over her lap before I knew what had happened. I was amazed, even frightened by her strength. When she started spanking me, she almost knocked the wind out of me. Despite the fact that I was being spanked through my dancing tights, it hurt like holy hell!

I was whimpering helplessly like a child. "Ow! Ow! Owww! You're hurting me!" I pouted.

"Oh, shut up! I haven't even begun to hurt you, little missy!"

The Other Mistress must have been within distance. Mistress Jackie stopped the spanking just for a moment to talk to her, "Will you get that handled dildo and bring it here, please? Thank you." She immediately returned to my behind, which was already smarting. Mistress repeatedly told me to stop my whining as she smacked my bottom. By this time, I knew I was going get a lot more than I had bargained for.

Mistress Jackie pushed me to the floor and I started rubbing my bottom. She stood and again directed me to suck her cock. I could hear Kelly chatting and laughing with some people off in the distance.

"Kelly, will you come here for a moment please?" I had the feeling this was not going to go well. Meanwhile, Mistress started fucking my mouth very hard. She was trying to jam this huge, black rubber cock down my throat. It was hurting the roof of my mouth, and it was gagging me. I was trying to push back against her hips, but she was much stronger than me.

I had tears running down my face from gagging. Apparently Kelly had been standing there for some time. Mistress said to her, "Mikel has something to tell you." But she kept fucking my face and said to me, "Don't you?" I nodded. She crammed the dildo hard to the back of my throat. "Don't you?!" I gagged and coughed.

I was still on my knees. Mistress had me turn around. There was sweet little Kelly. Behind her was the Other Mistress with a curious look on her face. "Tell her!" Mistress ordered.

I had tears running from my eyes from the choking. "I uh... the other day... uh... when you came in the store..." Kelly was listening like there was nothing wrong. I continued, "I was in the fitting room... um... and you were out in the store... and I was playing with myself..." Kelly looked confused and looked at Mistress. She filled in the blanks, "He was listening to you talk, prissing in front of the mirror in his little sissy outfits, wanking his little wee-wee, getting off on your voice." Kelly just made a troubled smile. The other Domme glared.

Mistress said, "We're going to need to teach him a lesson for taking advantage of my girls." The other Domme stepped in with a large 12" dildo on a handle, waved a condom in front of me, gave it to me, and said, "You know what to do with this, dontcha bitch? And hurry it up."

While I was unwrapping the condom and putting it on the cock, Mistress Jackie told her, "I want that dick in his mouth while I spank him. He's a whiner, and I don't want to hear it. Then she said to Kelly, "You really don't have to worry about him wanting to fuck you, Kelly. He doesn't have much of a dick to begin with. A little pussy-boy like this, all he'd really want to do is put on your clothes. That's all sissies ever want to do is put on your clothes.

The Other Mistress had put the handled dildo in my mouth, and she added with laugh, "And maybe suck your boyfriend's cock. He obviously likes that."

Kelly chuckled, "Yes, I can see that." This normally bubbly girl was now quite serious and quiet. I felt like I was being chastised by the mother of the family for some great infraction against her daughter.

"Oh, and tell Kelly what you have back here." She was referring to my butt-plug. I closed my eyes and sighed. I mumbled, "I have a butt-plug in my pussy-bottom."

Kelly dropped her head lower to try to hear the sissy kneeling in front of her, "In your... what did you call it?"

"My pussy-bottom..."

"His pussy-bottom," the other domme repeated in a mocking tone and big smile.

Kelly politely covered her mouth as if to either mask her horror or stifle a laugh. She just looked down. I was feeling so small. Here I was totally exposed in front of this very cute young girl as the complete sissy as I am. She knows that I had been playing with myself in the fitting room while listening to her. She's watching me suck on a dildo, and now she knows that I have a plug in my ass. What a fucking loser, she's thinking.

Mistress had me kneel on the chair. Kelly gave me a concerned look and asked me, "So you hide in women's fitting rooms and masturbate?

I started to explain so she didn't think I was a total perv. "I was trying on some leotards in the fitting room, and you came in, and..." The other domme crammed the dildo back in my mouth and mocked my tone of voice, "I was trying on women's clothes and wanking off when you walked in... suck it bitch!"

I was really getting scared how this was going. Mistress Jackie told the other domme, "Keep that in his mouth. He's a whiner, and I don't want to hear it." She started up with the spanking again, and it was every bit as bad as the first. Every time I whimpered, the other domme jammed the dildo harder into my mouth. She would slide it in and out and say, "You want to wear Kelly's clothes and suck her boyfriend's cock don't you, sissy? Don't you?" I would nod, and the spanking would come harder. Mistress would stop and press on my butt-plug causing me to moan out loud, causing the other domme to jam the dildo tighter into my mouth, causing me to gag.

Thankfully, this spanking didn't last too long, but it was utterly humiliating. I was about to start crying. Kelly just stood there, pretty much without emotion.

"Back on your knees." I quickly complied. "You will apologize to Kelly now."

I muttered a soft, "I'm sorry," with a very scorned look on my face.

Mistress got right in my face and over-enunciated, "I'm sorry, Miss Kelly... say it!"

"I'm sorry, Missy Kelly," I repeated humbly.

She continued in a loud voice, "For wanking my little wee-wee in the fitting room while listening to your voice..." she started this litany and I repeated each line.

"I'm just a little sissy faggot wanker..." (I was hearing some laughing in the distance.) I repeated.

"My dick is too small to ever fuck you..." I repeated.

"All I could ever hope to do is put on your clothes and suck off your boyfriend..." I repeated.

"I hope you'll forgive me. I'm so sorry." I repeated and looked at the floor.

Kelly just kinda did a half chuckle/half roll of the eyes and said OK and then turned to Mistress to ask her some question about something she wanted done prior to closing. It was totally business, and I was clearly inconsequential.

The other Domme had already walked off. Kelly walked off to take care of her work. I slumped on the floor on my knees feeling completely belittled. Mistress Jackie snapped her fingers three times. I looked up to see her pointing to the end of her massive black rubber dick. "Right here," she said calmly.

I moaned and mumbled an, "Oh no, please Mistress."

"Oh, you're not done sucking yet, honey," she insisted.

I sighed and took it in my hand and stroked it. The condom was smeared with my lipstick. She pushed my head onto it. I began sucking it with all I had and started moaning. I started to become possessed as Mistress talked to me about how I sucked cock.

"You really do like that, don't you? You wish it was real, don't you? You really do wish you could suck Kelly's boyfriend's dick. Don't you? You wish this was a real cock so I could cum down your throat, don't you?" I nodded an affirmative each time. I kept right on sucking and breathing harder and harder like a wanton cocksucking bitch.

"You wish I could turn you over right here and now and yank down your pretty tights and fuck you right up the ass, don't you? Don't you? Don't you?! Say it!"

"Yes, Mistress! Fuck my ass!" I said.

"Tell me what you want, bitch, I can't hear you!"

"I want you to fuck my pussy-asshole. PLEASE fuck my ass, Mistress! Fuck me the bitch I am!" I yelled.

She fucked my mouth hard and called me a disgusting, cocksucking slut.

Then, she sat down and pulled me up on her lap. This was the grand finale spanking. It was like the end of a fireworks display, and I thought she would never stop. She berated me in the most viscous tone of voice with a non-stop list of humiliating names. Somewhere along the line, between the pain of the spanking and the verbal assault, I started to melt and break down.

"Yeah, let me hear you cry," she said with some degree of pleasure as she continued the spanking. She knew she'd get me to this point. "That's right. Let me hear you cry, little girl."

That was all it took, and I started sobbing. "Yeah. Cry like a little girl!" I collapsed, draped on her lap.

With that, Mistress Jackie just stood up, and I rolled off her lap and fell to the hard floor with a thud. The fall stunned me and then the tears started again. I could hear her walking off in that same march that she came in with some 30 minutes earlier. She had totally broken me, humiliated me, and left me crying on the floor. This session didn't come with a "happy ending" like I had always had with private domme sessions. She had totally head-fucked me and left me in a heap.

I looked around and realized that I was laying there alone. After some time, I managed to get up to sit in the chair. I was shell shocked. I just sat there in my self-pity. A little while later, Kelly came by in her cheerful self as if nothing was wrong. She put a hand on my shoulder and asked me if I wanted something to drink. The gesture caused my face to pout and start up the tears again. I am such a pathetic sissy crybaby. I so wanted her to hold me and hug me. She gave me a bottle of water and told me to just take my time and relax.

The other domme walked by wearing surgical gloves carrying the strapon Mistress had been wearing. This was surreal. It was as if I had gone in for some medical procedure. The surgeon had left the operating room. The assistant was now taking out the primary instrument that had been used in the procedure, and here was a nurse helping me in recovery. I was still feeling the effects of all the emotional and physical pain I had endured.

A few minutes later, my mind started to clear, and I got back up on my feet and made my way to the foyer. Of course, I was still teetering in my heels and the butt plug was reminding me of the glow on my bottom. When I reached the outer area, Mistress was out of character and back to her cheerful self when she first greeted me. "How are you doing?"

"Much better now, Mistress. Thank you." I was very contrite. We had a nice chat.

In a very meek voice, I asked, "Mistress, may I use the restroom to remove the plug from my pussy-bottom?"

In a parental tone of voice, Mistress answered kindly, "No you may not. The plug will have to stay in place until you get home. Okay?"

I "Yes, Mistress," I answered. "Mistress? When I get home, may I please have permission to masturbate my little wee-wee and lick my sissy cum off my dildo?"

Mistress smiled and said, "Yes, you may lick up your sissy cum, but you must not miss any of it. Okay? You have to eat it all up."

I was relieved to hear this. "Oh, thank you Mistress."

I thought of one more thing. "Mistress? May I fantasize about sucking off Kelly's boyfriend while I'm doing this?"

Mistress Jackie raised an eyebrow. "Well, I think you should ask Miss Kelly that first. Kelly?"

Kelly was nearby and came over. Mistress told her I had something to ask her. I was feeling like a complete loser and this would completely confirm it. I almost couldn't get through what I was going to ask her.

I was had my head down in my hand was mumbling like a little girl, and Kelly had to come closer and look at my mouth to understand. "Uhm... Mistress has given me permission... when I get home? ...to masturbate my little wee-wee onto my dildo?... and lick it up?... and I asked her if while I was doing that... if I could fantasize about... uhm... oh god... I'm sorry... I'm embarrassed now... if I could fantasize about... sucking off your boyfriend."

Kelly immediately started to laugh and put her hand over her mouth to avoid being rude. "Are you gay, Mikel?

"No, I'm just a sissy. I fantasize about really beautiful women making me service their boyfriends or husbands," I explained. "I'm sorry if it bothers you."

Kelly answered, "No, I'm just trying to understand. That's fine. You have fun with your fantasy. My boyfriend's name is Paul. You have fun sucking his dick, OK? I'm so glad you made it out here, and I hope you'll come back to see us the next time you're in Florida!"

This time, Kelly held both of my hands, gave me a big smile, and bade me goodbye. No hug this time. Here was this little queer boy wearing a butt-plug, padded bra, thong leotard, tights, heels, and smeared makeup. He was about to go back to his motel room and suck on a big dildo while having a fantasy about blowing her boyfriend while she watches. Then he's going to wank onto the dildo and lick it clean pretending that he's swallowing her boyfriend's load. Okay, buh-bye!

Mistress was very gracious, gave me a hug, and told me I was a good little subbie. "I hope you'll come back next time you're in Florida, hun."

I told her I would. I minced to the door and peeked out. Mistress looked out with me and checked the parking lot. She said she'd watch while I walked to my car. As I often do, I felt so exposed in my little sissy getup with my butt-plug fucking my pussy bottom. I wanted to get back to my motel as soon as possible to play out my little fantasy of sucking off Kelly's boyfriend.

My Visit To Florida, Part I

2008-06-18T11:50:00.003-04:00

I love being out of town because I can go shopping, be a sissy slut in public, and be much more daring than I would normally be near home. Once, I had the occasion to travel to Ft. Lauderdale to attend a surprise birthday party of a friend. I was traveling alone, and of course, I brought lots of sissy clothes and toys.

As soon as I got out of the airport in my rental car, I changed into a pair of suntan pantyhose and some denim short-shorts that crawl way up my sissy bottom. I wore platform sneakers that were still kinda fashionable at the time, a light top with an unpadded underwire bra. There was no mistaking that I was NOT a girl but a sissy boy.

I had several days before the party and had planned to drive to another city to visit an old friend there. So, I could priss along the way. Occasionally, when the situation allowed for it, I would get out of the car so I could be seen and giggled or laughed at. At a shopping mall, I parked and got out of the car and walk toward the entrance as a group of hot girls were walking out. They immediately noticed me but were politely quiet as they passed. Then came the snickers followed by the hysteric laughter. I love that humiliation. I can play the sounds in my mind over and over.

At one point at a gas station, there were no less than six women looking at me simultaneously from different angles. Some were filling up their cars; some were going in or out of the convenience mart. I had added a pair of lace anklets to the outfit to make it even more demonstratively sissy. The reactions filled the air from “oh my god” to giggles to outright laughter coming from several directions. I paid no attention as I was only the mindless priss looking for something in the back seat. But my face was burning red the whole time.

Several times along the way, I got into my thong leotard and tights and looked for opportunities to parade my sissy self to those amused by a pathetic sissy.

While there, I stopped in a local dance shop and had a most interesting experience. It was mid-afternoon on a weekday, and I was the only customer in the store. Normally when I visit a place like this I would call first and ask about trying things on, but since I was out of town and feeling frisky, I decided to just go in. Oh, I was dressed in something a bit more conservative than described above. I was greeted by the clerk. I browsed for awhile, obviously looking at the female leotards, and she said I was welcome to try things on if I needed to.

I found some thong leotards in my size and headed for the fitting room. While in there, I heard the bell on the front door, and it was obvious that a young woman had come in. She was very outgoing and talkative; in fact, she was a regular Chatty Kathy. I was enjoying listening to her while being in my fitting room trying on leotards. I was prissing in front of the mirror and starting to play with myself while I listened to her cute, bubbly voice.

I finally came out and had a chance to check out the customer. She was in her mid-20s, very outgoing, and started to chat me up as I did a little more browsing. I conspicuously placed two leotards on the counter. As the clerk made her way over to help me, the cutie was now curious about what I was buying and asked who I was buying for. I held them up and told her they were a couple leotards for me. She asked if I was a dancer, and I simply replied, "Um, actually, I'm a sissy... and I like to wear girl things." She was interested and amused by this, and she started talking about where she worked which happened to be a BDSM club across town. I couldn't believe my good fortune at hearing this. The clerk was also intrigued, and I asked her what they did there.

She said they got into mild bondage and discipline scenes there. She wasn't a dominatrix but a hostess. She was obviously way too bubbly and nice to be a domme. She said she welcomed people and served drinks and entertained a little. It was a commercial place that did mild scenes and must have just skirted the law. She said that all men were admitted free if they came in drag. I asked her if I could just show up in my sissy attire, namely my leotard, tights and heels. She said certainly, that would be fine. I also asked if I could get a good, sound spanking there. I was starting to get pretty daring in my conversation with this girl, who later told me her name was Kelly.

Kelly told me they did spankings, but they couldn't do it on the bare bottom. The clerk said she thought this was interesting and didn't know this kind of place existed. I told Kelly that I'd had a few private domination sessions in the past and had been humiliated with strapon dildos. She said they couldn't do that. I told her that I'd only been made to suck them. Now I was showing off in front of the clerk, who was being polite but was amazed at the conversation.

I said to the clerk, I'm sorry if this is freaking you out or anything. She said no, it was very interesting; she'd just never really heard of that kind of stuff before. I explained that I had never been to a club of any kind before but had only been to private sessions with a Dominatrix involving crossdressing, spanking, and humiliation with a strap-on. I really wanted to tell them about how I would lick my cum off the dildo, but I figured I was pushing it.

Kelly gave me some details about the club. It was a place where people could come in and do their own scenes. There are a couple Mistresses available to get into scenes. There were limits on what can be done. She gave me the location said they were open on Friday and Saturday nights. I would have time Friday, so I told her I was looking forward to a visit and a good, hard spanking!

To be continued...

The end of a relationship

2008-06-09T16:23:00.006-04:00

Carla was a wonderful girl. She was a loving, giving person. Sexually, she was the most open-minded woman I've ever been with, but unfortunately she had baggage... Major baggage that I can't go into here, but let's just suffice it to say that it was bringing the relationship to a screeching halt. We really did love each other, but her low self-esteem (and I thought mine was bad!) was creating intolerable problems for us both.

In the bedroom, we likely would have progressed to her wearing a real strapon. I know she was up for that. And maybe we could have moved to her playing a little light domination. She was a little sensitive about being called a "whore" when passion was getting high and language was getting nasty, and believe me she could embarrass a sailor through gritted teeth as she ground and humped and fucked back. Calling her "my whore" was OK, but not otherwise. During one of our last escapades, I took a dildo and placed it between her legs and told her I wanted to be "her whore" and began to suck it. With a bit of a knowing smile, she put her hand on the back of my head and pushed me up and down on the cock for awhile. That particular scene didn't last long that night. I was hoping we could take it to having me lick cum off the dildo.

I'm pretty sure we could have gone there, but it ended soon afterwards.

Damn. All of the other components were in place. I was wearing lingerie in her presence full time. If I ever wore men's underwear, she would ask me if something was wrong. She had me eating cum. She was fucking my ass. Sucking cock should have been next. I was hoping I could have moved her along to dominating me with all the trimmings of humiliation.

That's really what I craved. I wanted so much to have her to stand over me in black stilettos wearing a 10" strapon, pointing to it, and telling me to suck it like the little sissy bitch that I am. I wanted her to make me wank off and make me lick my cum off her big cock while she called me a cum-eating cock sucking whore. I needed that so bad.

It just wasn't to be. We were on again, off again, off forever. Time to move on.

JamieLin, where are you??

2008-06-09T16:21:00.001-04:00

JamieLin, I sure wish you'd put your blog back up. I was inspired by your writing. I wish you'd come back.

Carla Takes Me

2008-05-19T10:23:00.004-04:00

This is the closest Carla came to dominating me. She knew I loved to be stimulated anally. Being a lover of anal sex herself, she knew well the delightful feeling of being penetrated “back there.” There were many times while blowing me when she would finger fuck me into a crazed orgasm. I often brought over a number of favorite toys for our weekends together which included a medium sized butt plug. She knew well the affect it had on me. By this time, I had not yet purchased a strapon, but I had talked about them, and I think Carla would have been open to using one on me. We broke up before we ever got to trying that.

However, one night Carla lubed up the butt plug and I smiled and rolled over to have her put it in my bottom. Usually, it was put in and stayed in while we played and fucked. But this night she gave me a lot more than I expected. I could sense Carla was positioning herself behind me, and I turned back to see her holding the plug against her pubis and getting ready to mount me! She had a wicked grin on her face. I let out a stunned, “oh my god!” as the cold KY slathered up and down my crack. Then gently, she pushed the plug in about halfway, pulled it out most of the way, and then buried it as she lay on top of me.

I whimpered a breathy “oh!” as I felt like an innocent girl being taken for the first time. Carla slowly pulled the plug back out and thrust it back in again. After about a half dozen strokes, I thought we might move on to some other mutually satisfying activities. With a smile, I started to turn around and roll over. Carla had a determined look on her face, and not so gently pushed my shoulder back around and pushed my face into the pillow. She pumped faster as I moaned out loud into the bedding.

She got my ass up higher so she could get a better stroke. She was very lean and strong. I was amazed by her persistence in doing this all while holding the base of the plug firmly against her pubes while she fucked me like a man would. Several times she grabbed me with both hand by the hips and just slammed against me, slapping her pelvis against the plug, driving against it every time. I was whimpering and nearly crying by this time, but she was relentless as if it was her cock, and I wasn’t going to deny her getting off.

Several times she would tease me with a reach-around, and stroked me with one hand as she butt fucked me with the other. There was some lingerie on the bed, and she took a pair of panties and stroked me with them. Knowing I was getting close to the edge, she pushed me back down with a half-slip and several pair of panties between my dick and the bed. She fucked me and giggled as I humped the lingerie. As I moved, I was also fucking myself against her.

Between the silky lingerie rubbing my cock and the mixture of pain and pleasure in my ass, I was in a frenzy. Carla whispered for me to let go. I felt like a virgin bride at the hands of her husband on her wedding night being urged to let go as he fucked her. I came like a bitch, I squealed, I screamed, I whimpered, and Carla kept right on fucking me. I thought she wasn’t going to stop, and I was about to beg her to because it was starting to hurt. Finally, she collapsed on top of me while I laid there with a plug in my pussy-bottom and a huge wet spot in the lingerie under me.

After some time, Carla started to kiss the back of my neck and tell me how good I was. I felt like I was just taken like a girl. After we rolled over, she put the covers over me, and she held me in her arms. I felt safe and protected.

House Dressing

2008-02-25T23:08:00.006-05:00

One evening on the way over to Carla’s apartment, I picked up a couple of salads from Wendy’s. There was a promising night ahead. When I got there, I was already turned on, and as she got our dinner out of the bags, Carla wanted a panty report. That is, she wanted to see what panties I had worn for her that night. I was only too happy to oblige, and quickly got my pants off so I could model my panties for her. Of course, she approved with a few gropes here and there, which only served to get me all the more turned on. She even got me out for a few strokes to tease me for what was ahead after dinner.

She had put the salads into some bowls of her own, and we were going to dine on her couch. Feeling frisky, I was stroking myself and jokingly asked if she would like the “house dressing.” She replied, “Well, of course!” and her wicked smile. I acted like I was going to jerk off into her salad, but of course I was only acting. She continued to hold out her bowl.

I started to sit down. “I’m waiting for the ‘house dressing,’” she said coyly.

“Are you serious?” I asked.

“Well, you offered the house dressing, and I accepted. Now, when do I get the house dressing, waiter?”

Shit, she was fucking serious! I stood back up while she held out her bowl. She had a grin with raised eyebrows. She started a little role-play like I was the waiter in a restaurant.

“You know, I’ve heard the ‘house’ is really good… very creamy and warm… just the way I like it. I hope you’ll give me a little extra on my salad.” She started to play with my balls. “Can I pump it for awhile?”

“Yes, of fuck!” My panties were down to my thighs as Carla pumped my cock with an innocent look on her face. She continued to make her little teasing double entendre remarks in a matter-of-fact tone of voice. I took over and started to jack it faster.

“Is that dressing ready for my salad yet? I’m getting hungry!” She acted like she was getting impatient.

I started to moan and scream. She held the bowl in place to be sure she caught it just right. As I started to shoot, she rotated the bowl to get coverage of the salad with the house dressing. I couldn’t believe I was cumming on her salad.

“That looks yummy!” she said with wide eyes as she licked her lips. Another spasm of cum shot out on top of the lettuce leaves. She continued to rotate the bowl to try to catch the jizz dressing on more of the lettuce. I moaned again as she giggled. Unbelievable!

I collapsed on the couch next to her as she laughed and thanked her waiter for delivering a nice amount of the ‘house.’ She promised a nice tip for me later. Next was a mind fuck the likes of which I’ve never experienced before or since.

Slowly, Carla took her fork and selected a few leaves of cum-soaked lettuce and ate it. I was stunned that she’d actually do it. I mean, first of all, it was now cold. And secondly, it wasn’t like it was on me or something. She was just eating salad with jizz on it.

“Mmmmm…. this is very good dressing,” she reported. She took another forkful as I watched in stunned amazement. Then, by about the fourth forkful, she carefully dipped leaves into the puddles of cum still in the bowl and then held it up to my mouth to feed me. Inside, I thought ‘I can’t possibly do this,’ but Carla had this way of just doing things with full expectation that I would participate, and I would. I ate the cold salad with the cold cum dressing. Truthfully, it wasn’t really as bad as I thought it would be since the lettuce was nice and fresh. The water content diluted the taste of the cum.

She then prepared another fork-full for herself and ate it. Again it was my turn, and I obliged as she fed me. We giggled like two girls wearing our panties eating on her couch. But this was just another lesson in sissy cum eating. Carla had no shame when it came to sex, and from that shamelessness, she was teaching me to enjoy eating cum the way she loved it.

There were many shared cum eating episodes to follow. Almost every blowjob was snowballed. She might give me a handjob in the car and then lick her fingers and offer some of it to me so I could help her lick her fingers clean. She liked me giving her a "facial" so that afterward I could lick it off her face and we could share it in our kisses. In the end, Carla taught me to be a cumslut.

Carla's First Lesson

2008-02-12T10:51:00.000-05:00

Wearing panties every time we were together was by now typical and soon progressed to my wearing pantyhose, which she just LOVED. I wondered just how far I could go with this. Could I get it to the point I was with Terri of years gone by? Could we play dress up together and wear bras and everything? Short answer: mostly yes, all in due time. More about that later.

As I mentioned in my previous post, Carla's lessons were in the form of learning acceptance. One of those lessons came in a most unexpected way. First a little background. This girl could suck cock 'til the cows came home. She was never slutty. She never acted slutty or talked dirty. It's hard to explain, but she was the only woman I've ever known who could look demure with a dick in her mouth. And, OMG, she could deep throat! I've never experienced that before or since. At first it was scary! I thought she was going to swallow my cock and consume it. She always swallowed my cum and was certain to get every last drop by stoking it in her mouth until my balls were drained and I went limp from the pain.

But this lesson is really about cum. Cum. Cum everything. Cum all over your face. Cum in your mouth. Cum down your throat. Hers... and mine. You see, while some guys are totally turned off by a woman kissing them after given them a blowjob, I've always thought it was particularly sexy to french kiss a woman after she had swallowed my load and I could taste the remnants of it. I wanted Carla to know how evolved I was by letting her know that I thought the taste of cum was sexy. I even licked it off her breast after cumming on her chest one time.

SNOWBALL

Once after giving me a particularly ball-draining blowjob one night, Carla gave me a VERY big surprise. She had sucked me completely dry to the point where I thought I might not ever cum again! I was lying there in an exhausted heap, and she returned quietly to my side and snuggled me for a moment while I caught my breath. Several minutes had passed before I started to show interest in her again and started kissing her. She slowly moved to gently kiss my lips, then moved above me. Eventually as her tongue met mine, an avalanche of warm cum began draining into my mouth as she continued a most passionate kiss. It was intoxicating. Her mouth was now sealed over mine to prevent any loss of the jizz as she stirred it in my mouth with her tongue.

There was no choice here: she was on top, and this load was mine to swallow. She had patiently saved it and brought it back to me as a gift. This kiss lasted for at least ten minutes while she silently demonstrated to me what an erotic woman does with a mouthful of her man's orgasm. It wasn't until all of it was extracted from her mouth and she was sure I had swallowed every last drop that she removed her mouth from mine and returned to my side without a word. I was speechless.

I had eaten my cum before, but this was the first time I had really experienced it, really savored it in my mouth. She had just shared with me a very intimate experience that is one normally only a woman could have. Carla gave me that experience--without any shame or guilt--as a gift.

Carla

2008-02-01T11:31:00.000-05:00

Carla was the all-time kinkiest woman I've ever dated. She seemed to have no shame at all. We became emotionally and sexually involved on our first date. I spent the night on Friday, and we fucked our way well into Saturday. After showering, I was going to run home, get some fresh clothes and return. I thought I'd test her a little by pointing out that I didn't have any clean underwear.

This is a little game I've played with girlfriends to see if they'd offer something of theirs. It had never worked in the past.

"Well, just don't wear

any," she said with a wicked smile.

"That always feels so yucky," I whined. I'd hoped she'd come up with a helpful suggestion. She did.

She smiled coyly. "Would you like to borrow some of mine?"

I blushed and stammered. I'm such a good actor. I let her talk me into it. As she pulled opened her panty drawer, I gasped at all the sexy and silky panties she had. "You have some naughty little things here..."

She pulled out one of the more daring pairs and held them up. I protested in feigned embarrassment that I couldn't wear something like that. But I had to be careful; I didn't want her to pull out some boring cotton ones.

"Well," I said with a smile, "since you're lending me your panties, I should let you choose the ones you'd like me to wear."

Carla was like a kid in a candy store considering so many different styles to find the right one that she was going to have my wear home. As she would hold up the smaller bikinis, I would remind her that I needed some room to accommodate my equipment.

After considering at least a dozen pairs and being taken on a very nice tour of her lingerie drawer, she finally displayed a pair of silky white bikini panties with a sheer lace front inset. She held them open near the floor so I could step into them, and my dick started throbbing. As she started to bring the panties up my legs, Carla took notice of my condition which was now right in her face. She smiled approvingly, and said, "Well, are we getting a little turned on here?"

She was teasing the shit of me and loving it. Once she had pulled the panties up to the top of my thighs, she acted as if she didn't know how she would get them over my dick sticking straight out. She looked quizzically at the situation and said in a dumb voice, "Hmmm.... well maybe they won't fit after all."

"You might have to make things fit!" I suggested.

"O-o-o-o-hhhhh," she said, and then giggled.

Then she softly handled my dick in such a way as to be stroking it as she made various attempts and re-attempts to put it in the panties. The moving and stroking caused me noticeable frustration which I voiced.

"Well I'm sorry," she said in a mock apologetic tone, "I'm just trying to get everything to fit right."

"You're only making matters worse!" I countered.

"Yes, I can see that," she gleamed.

After all this fussing, she finally had me turn around so she could admire the fit. She was enjoying the view. "I love it!"

I thought I was in heaven. Here was this incredibly sexy woman who had just put me in her panties, and she was enjoying this! Could I tell her that I have my own collection at home?

I drove home with a raging hardon wearing these lacy underthings, debating all the while if I should wear them on my return. I decided I should act "normal" and return wearing men's underwear and politely thank her for the loan but also let her know that I really did have fun wearing them.

On my return, she was actually disappointed that I wasn't wearing her panties. I told her I'd be glad to wear them again. Before the weekend was over, we did have another experimentation session with some other pairs of Carla's panties. I knew this was going to be a fun ride.

I brought up the subject of panties a couple times again when we talked on the phone. This was still almost too much for me to believe. She really liked seeing me in panties! It was the subject of some coy conversation, and I hinted at the idea of wearing something "for her" upon my return.

When I returned, I was in fact wearing a pair of my own lace trimmed panties. I was really nervous about it. This would be a revealing moment as she would know that I had my own. Then again, I figured if things went terribly wrong, I could also make a joke of it and tell her that I bought a single pair as a joke just to play with her head.

After I had been there for awhile, I told her I had a surprise for her and hinted where the surprise might be. Once she took the clue, she put her hand down my pants, she smiled and said, "Well, we know what they are, but we need to find out what color they are."

Before long, she was giving me more of her panties on permanent loan and buying me frilly, lacy, bikini panties with the expectation that I would wear them for her on dates and, more importantly, in bed. She knew how much they turned me on, and she reaped the benefits thereof.

Carla seemed to have no inhibitions whatsoever about most anything concerning sex. It was only my inhibitions and fears that kept me from fully revealing myself to her.

Now you're probably thinking this was too good to be true. It only lasted less than a year for reasons that I will soon reveal to you, but in that year, Carla taught me a lot about self-acceptance.

Leotards and Tights

2008-01-30T17:58:00.000-05:00

One of my favorite sissy outfits at home has always been leotards and tights. I would dress up in my favorite outfits consisting of shiny black tights, a bright colored thong leotard over a padded bra, and high heels. It was a very sissy-slut look!

I started a late night ritual of going out wearing my dancewear under regular shirt, pants and shoes. In the car, I'd take off my pants, unbutton my shirt and put on my slutty pumps. Then I'd have fun just driving around in my ultra-slut outfit. When I was sure I wasn't going to be noticed, I would take off my shirt and drive in just the leotard and tights with my ample, shapely breasts jutting out on either side of the seat belt. With my dick tucked tightly inside my tights and leotard, I would rub my crotch for hours as I drove around feeling like a naughty dancer girl. Sometimes I would have a butt plug inserted, making the ride all the more erotic.

My self-daring brought me to drive past night clubs where I knew really hot and often drunk girls would be coming or going. I would time things so that I would be out of my car, totally exposed in my sissiness in front of a group of hysterically laughing women. Feigning embarrassment as they saw me, I would try to cover my boobs, turn and walk the other way. This only served to entertain them all the more as they caught sight of my thong bottom in shiny black nylon. Embarrassed and humiliated, I would run off awkwardly, teetering in my 3" heels. One girl ran after me so she could pinch my nylon covered bottom. Another wanted to squeeze my padded boobs. It was a classic case of reverse sexual harrassment.

This little scenario was met with dozens of appreciative audiences of women of various ages. Sometimes these women would start up conversations with me. Frequently they would compliment me on my legs and ass, and sometimes they'd ask me why I was so attired. I would usually tell them that I lost a bet and my girlfriend was making me do it, or I would simply tell them the truth that I'm a sissy. On a few occasions, the girls would feel me up for laughs. The giggling and laughing was positively addictive.

One girl put her hands on her hips, and with a look of contempt asked, "Are you looking for a man to fuck you?" Some of the things are still burning in my ears.

My craving for this humiliation caused me to become more daring. Sometimes I'd go for the jazzercize look and instead of wearing the bra and heels, I'd just wear sneakers. I made an unlikely looking male candidate for an aerobics class. Only a sissy would wear a leotard and tights!

I had a lot of fun trying on leotards in dance shops, too. Most places were friendly to male clientele, and I was permitted to try on all varieties of feminine dancewear in the stores. Some of the clerks couldn't believe I really wanted to try on thong leotards.

Women's Jeans in Public

2008-01-25T07:48:00.000-05:00

I just had this thing for Chic jeans. They were the hot pair at the time, and I ALWAYS noticed whenever a woman wore them. The logo stiched in the back, the inverted curve in the pockets that came to a point. There was also this little reinforced stitch at the bottom of the fly that was unique to the brand. I could tell from any angle that a woman was wearing them. Terri wore them and looked hot in them, and I had always wanted a pair.

After we split up, I bought a pair and strutted around my apartment in them, checking out my ass in the mirror. I had a way of pulling up my pantyhose that gave me this sexy, feminine ass that looked really hot in Chic jeans. It was a long time before I finally worked up the nerve to wear them in public.

I was empowered one day when I saw this guy in a public building near where I worked. He was with his girlfriend, and he was wearing Chic jeans! I was stunned. I followed them for awhile. Did he know he was wearing girls' jeans? Was he wearing her jeans or were his own? I had to do this, too!

When I finally did, I wore them with a jacket or sweater over the logo. When I would let the logo show, I was making the message clear: "I'm wearing girls jeans!" I had a bit of control that way. Even though the pocket came to a point, from a distance, nothing really looked out of the ordinary. Then, if I wanted to dare expose the fact that I was wearing feminine jeans, I could let the jacket ride up and they could easily see that yellow stitched logo that sometimes literally had young women in stitches.

At first I wore them with my regular shoes because that's all I had other than high heels. I'd go to the mall and pick out a couple really hot girls, get myself in front of them, and let the jacket ride up. Sometimes there would be no reaction, but sometimes I could hear the giggling and the outright laughing when they would realize what I was wearing. The comments like, "Check this out," or "Oh my God! That guy's wearing Chic jeans!" would make it even more of a thrill.

Once, two girls followed me around a mall for about twenty mintues while they snickered and whispered to each other. My face was burning in humiliation.

I still have about five pair of Chic jeans. They're so comfortable. There was a point where I started wearing them pretty regularly.

But sometimes for the time spent, the reactions were just few and far between.

Now, if a guy is wearing back-zip jeans, there is absolutely no mistake.

I'd wear pants like these out in public and if a group of girls saw me, there was almost always a guaranteed reaction. Tight in the front with dicklet tucked away, no pockets, zipper in the back. They'd get hysterical!! (I didn't have a chain like in this picture)

Sometimes young girls in groups could be almost vicious dealing with a little sissy boy. Some of the remarks were priceless. "Look at this fag!" "He's got a girl's ass!" "Ohmigod, is that like an open invitation?!!"

Shopping excursions in my sissy jeans were were almost always humiliating.

Deeper Needs

2008-01-18T16:14:00.000-05:00

Terri was always understanding and supportive of my desires to wear lingerie. Every morning as we dressed for work, we’d put on our pantyhose together. We’d wear each other’s things. There was one shared panty drawer. She was fine with me wearing lingerie while we had sex. We engaged in many fantasies involving me putting on women’s underwear.

An example was her as the clerk in a lingerie store helping me try on bras and panties in the fitting room. At first, she's a bit put off by having a man trying on the delicates, but she's trying to be professional. The fit of the panties wasn’t quite right, and she dutifully fellated me to get my erection to go down. All in the interest of a proper fit, you understand.

Still my need for humiliation involved fantasies such as getting caught trying on panties and being punished for the act by being forced to put on a bra and pantyhose and heels; then being butt-plugged and made to suck a dildo while being verbally degraded. It’s that whole shame thing. Terri was a good actress, but she was never going to be a dominatrix, even a soft one.

At the same time, her needs weren’t being met by a sissy who was a lousy fuck. Most of us are, after all. Let’s face it: while real men are focusing on the feel of pussy and making a woman feel good, we’re busy fantasizing about bras and panties and hose (oh my!). We can’t get it up if we’re not fantasizing or engaging in sissy behavior. That’s the plight of sissies.

So over time, she started to look elsewhere for real sex, and as I look back, I can’t blame her. She would be out late with some lame excuse while I was home dressing up and jacking off.

We had discussed the possibility of a three-way, and she was open to the possibility. I had confessed to her that I wanted to suck cock, and that didn’t bother her. I hadn’t told her that I had done it once before we met. What a wonderful memory that was.

In a crazy moment five years earlier, I picked up two women in a bar. I knew one of them was a very passable transvestite. I was pretty drunk. I invited them to my apartment, and we started having some fun. The TV was just beautiful with long, slender, pantyhose covered legs.

I showed them that I was wearing pantyhose and a bra. The TV and I started feeling each other up. The woman sat on the bed while I knelt in front of the TV. I felt up her legs and pantyhose and started to rub her crotch.

The woman said, "I think he wants what you have up there." She pulled down her pantyhose and panties and revealed a beautiful 8" cock. Now this was a dick any woman would enjoy pleasuring. I was delighted to hold it and stroke it, and in short order, I put it in my mouth. It was wonderful feeling it slide in and out of my mouth while hearing his feminine voice moan. Before long, I was sucking cock like a whore, my head bobbing up and down while I kept a good grip on the shaft stroking it. I was making shameless slurping noises. What a sissy cocksucker!! He didn't cum, but I wanted him to. I felt wonderfully feminine and submissive doing this as the woman looked on. She didn't really humiliate me, but she was encouraging and saying things like, "That's right, suck that big cock!"

I never sucked another real one, but ever since then I've enjoyed the sensation of my lips wrapped around a dildo and my tongue licking its head especially at the command of a dominant woman. Of course, it's also a lot safer than the real thing. There's just something absolutely overpowering about a woman holding a huge dildo between her legs ordering me to suck her cock for her amusement.

I can understand how women can sometimes achieve orgasm from giving head. At times I’ve worked myself into such a frenzy that I’ve gotten lost into a pseudo-orgasm of my own. Eating cum is particularly emasculating. It’s something I often find difficult to do on my own unless a woman is ordering to do it. Girls laughing at me while I'm licking it up makes it especially humiliating and erotic.

Oh... I’ve digressed, haven’t I? Like I said, Terri never knew about my cocksucking experience, and we never had that three-way. I couldn’t handle the fact that she was sleeping with another guy.

Today, I have cuckold fantasies. I wonder now what it would have been like if I could have stayed on as her sissy maid. Maybe she could have talked her lover into letting me suck his cock while she looked on. Then they could have ordered me into the corner to sit quietly while he fucked her good, they way she really needed it. He could show me how it's done. Then while I’d sit there in jaw-dropped awe while she screamed in ecstasy, at least I’d have the pleasure of knowing that the dick that was giving her such a noisy orgasm, I got hard for her with my own sissy mouth.

So Terri and I split up. It was mostly amicable, although we argued over some clothes. “No, those were my panties!”

Only a sissy boy would argue over a pair of panties.

Halloween and Busted

2008-01-16T12:19:00.000-05:00

Terri and I were friends with Frank, the guy I worked with, and his wife Marti. I was always joking about crossdressing or wearing pantyhose or being gay, talking with a lisp trying to be funny, more as a macho cover-up for my real feelings. Marti always had a sly smile about that like she seemed to know the real truth about me.

One year for Halloween, Frank and Marti invited us over to their place to watch a movie. We agreed to wear costumes. Terri and I decided to go as each other. Actually, I convinced Terri that it would be a good idea. The night before, I put on my bra, pantyhose and a girdle, and she picked out a skirt and blouse that would work for me. We were pretty close in size as I’ve always been very small and could fit into most of her size 13 clothes.

Terri put on a pair of my pants and a shirt. That was the easy part.

I didn’t shave my legs then but instead wore dark hose, typical of what Terri would wear. My failing in being true to her form was the bra. While we wore approximately the same bra size, I wore a Bali full-figured model with three snaps, one that she wouldn’t likely wear. Terri had given me a gauzy peach colored blouse of hers, and the bra was slightly visible through the fabric. I rather liked that it was evident I was wearing “the whole bit.”

The hair was pretty easy. Both of us had about the same length, and all we had to do was arrange it a little differently. Of course, she had to do my make-up. I brought along some regular clothes so that I could feign discomfort and change into them while we watched the movie.

When we arrived at their place, there was the predictable reaction of laughter when they saw that we had dressed as each other. Frank came over to me and pretended to hit on me as Terri. Almost immediately Marti started in on me with that knowing look making comments about what I was wearing.

“Quite a thrill, isn’t it?” she asked me.

I tried to pretend to be awkward with how everything felt. I said something like pantyhose weren’t such a thrill after all the joking I had done about it, or something lame like that.

Then she said, “Are you wearing your girdle?” I will never forget the tone of voice. It was almost in mock excitement, like she knew I was using the opportunity as an excuse to put on all my girlie things and get away with it, only she knew perfectly well the real truth.

For a brief moment, I was speechless. How would she know that? Many women wore panty briefs over their pantyhose as did Terri and probably Marti, but why would she guess that I was wearing one, and why did she say “your girdle?” She fucking knew!

In fake naiveté, I stammered out that it was some kind of stretchy thing Terri gave me to hold up my pantyhose. Terri really wasn't helping much.

“Something from your collection?” Marti asked sweetly. Clearly she wasn’t buying it. She was reading my mail, and I was getting very nervous. My arms had been crossed in front of my stuffed bra, and I moved my hands in front of my flattened tummy.

Still sizing me up, Marti then checked out my bra through the gauzy blouse. “And what a pretty bra,” she cooed.

I should have just said, “Why thank you.” But I mumbled something about it being Terri’s.

Immediately Marti shook her head with a smug smile, “No it’s not.”

“Yes it is,” I insisted.

“No, it’s not,” she came back immediately; “She wouldn’t wear one like that. It’s too big.”

I tried to explain that it was one from when she was heavier. But Marti knew that even when Terri was heavier, she wouldn’t wear a three-snap bra like I was wearing. She had me, and she knew it.

Somehow we got off the subject, and we went on with the night. Later I told Terri I wanted to get my clothes out the car so I could change out of my costume. Terri said, “Oh just leave it on.” Marti jumped in with, “Yeah, you’re having so much fun! Or is your girdle too tight?”

I kept quiet about it the rest of the night. The ribbing died down for the most part, and we had fun the rest of the evening watching the movie. As we left for the night and said our goodbyes, I thought I could make a desperate attempt to save myself by saying that I couldn’t wait to go home and get all this stuff off (as if I didn’t like it).

Marti smiled and said in a sexy voice, “Yeah, you can go home and slip into something more comfortable.” She had that knowing look on her face again. I felt so busted again. Of course, I was going to go home and put on my nightie. I blushed.

Well, I had hoped this would all die down and go away. About a week later though, Marti came into our office. Frank and I worked together alone in the same room. Marti announced, “I’m conducting a survey on men’s sock lengths. She immediately went over to Frank, went down on one knee and examined how high his socks were. “Frank, you’re about a mid-calf.”

She immediately turned around to me and said, “Let me check yours now.” I was busted again!! Of course, I was wearing pantyhose as I did almost daily and as I often joked about. This was nothing but a deliberate attempt to expose me as the sissy that I am. She knew that if I was wearing pantyhose, I wouldn’t be able to participate in her little “survey.” I was totally fucked!

I just said, “I’m wearing mid-calf.” She pressed that she needed to check them herself. I acted shy and said something like, “I can’t allow a married woman to feel me up.” It was pretty lame. She knew it. I knew it. She knew I was wearing pantyhose. She had just confirmed that Halloween was not a one time thing but that I was indeed a sissy crossdresser and just needed the excuse to put on girlie clothes.

She just smiled that knowing smile.

I was totally humiliated.

Terri and The Lady at The Department Store

2008-01-10T10:45:00.000-05:00

I had a girlfriend named Terri who was surprisingly accepting of my crossdressing. The first night we got it on, I somehow worked up the nerve to tell her about it, and she let me wear her pantyhose the next day. We had a two year live-in relationship. While she accepted anything to do with my wearing lingerie, she didn't want me in drag which was fine by me.

Our little secret was to stay under my clothes or in the bedroom, and we had a lot of fun with it. I wore panties and pantyhose every day with her approval. I would wear bras around the house and in the bedroom. I would sleep in a silky nightie. We would share sexy lingerie. She would often borrow some of my things.

While I tried to lead her into it, Terri could never get into the humiliation component I craved. This was even before the cum eating and anal phases that I eventually evolved into, but I still had this part of me that needed exposure. Once at a party while drunk, I told a woman that I wear panties. When she went off to Terri for confirmation, she was quite nonchalant about it and explained that she washed my panties in the sink with hers.

Terri was willing to take me shopping for lingerie at Frederick’s on a few occasions. She knew that I loved embarrassment, but she didn’t want to be embarrassed herself, so she had limits.

Every once in awhile, she would surprise me. Once we were shopping at a department store and passing through the menswear section. There was a bin display of men's nylon bikini underwear. This style was very similar to a plain bikini panty. Now, this was somewhat advanced for the time as there wasn't much available for men other than the typical boring cotton briefs or boxers. We stopped and noted the style and make of the bikini. She teased me that I'd still rather wear ladies panties. "Of course," I replied with a sly smile.

About that time, another woman happened by and noticed the display with a raised eyebrow. She made a remark about the style and the fact that they were made of nylon, and I said that I thought nylon was much more comfortable than cotton. Then she said to me, "Really? But these aren't much different than women's, are they?" Terri replied, "No they're not, really, and they're much more expensive than women’s." The woman agreed. Terri went on, "That's why I just buy him ladies'…"

There was an uncomfortable pause as we both looked at her with shock.

"You buy him ladies panties?" she asked. I looked at the floor and said under my breath, "I can't believe you're telling her this."

Terri was completely matter-of-fact. "Sure, he likes the feel of nylon. And there are many more styles and colors to choose from. And he actually looks pretty cute in some of them." She giggled. I crossed my arms and scratched my forehead. With wide eyes of disbelief, the woman said, "Well I might get a pair of these for my husband to try, but I don't think I'd ever get him into panties. That’s for sure!"

That sent a wave of humiliation through me. Her man wouldn't wear panties. A real man wouldn't wear panties.

They were finishing the conversation, and my face was red hot by then. I said to Terri in an incredulous tone, "Oh great, just tell her I'm wearing women's underwear!"

She giggled, and said, "Well, you are! Maybe you’d like to tell her about your pantyhose!"

I sighed out loud in desperation. The woman laughed as I pushed Terri down the aisle. I was embarrassed, red faced, and totally turned on. I couldn't believe her guts to expose me to this perfect stranger and tell her that I wear panties. I was completely befuddled the rest of the afternoon.

Situations like this were rare, but I’ll remember the embarrassment forever.

Cum Eating and Facials

2008-01-09T09:47:00.000-05:00

“Do you eat your cum?” asked one of the massage parlor girls during a session. I was taken aback. I guess the thought of eating cum hadn’t entered my mind. And yet, it also seemed like it was something I should be doing. I was loving the feeling of being penetrated. That feeling, combined with the bra embracing me and the pantyhose on my legs and the tight girdle on my ass just made me feel so wickedly feminine. Licking cum was just the next logical step.

By this time, I was spending a lot of time and money on phone sex, and one particular phone dominatrix had me sucking a dildo regularly. I had purchased it some time ago, but felt a little self-conscious about what to do with it. In our fantasies, Mistress made me suck on her cock with abandon, and eventually I was cumming on the dildo so I could lick it clean while she called me all sorts of derogatory names. I certainly fit the title “cum eating bitch,” didn’t I?

One particular phone Dom took me yet another step by giving me a facial by “walking the wall.” Once she had me worked up, she had me put my ass against the headboard of the bed with my feet up. Then pushing my feet against the wall, I was instructed to move my hips up over my head so I could cum all over my face. I couldn’t believe I was doing this. As I was starting to cum, she barked, “Open your mouth! Catch some of it in your mouth!”

Not only did I get it in my mouth, but I got it all over my face. I felt so humiliated while she laughed at me. “How do you like THAT, bitch?” Then as she instructed, I used the dildo to smear the cum from my face into my mouth and suck the dildo clean as she continued to berate me. I pouted while she said, “That’s a good girl. Lick it clean for me!”

When that call was over, I felt so used and dirty and cheap.

When could I do this again?

The Next Step in Sissyhood

2008-01-07T10:28:00.000-05:00

I’ve always been jealous of the variety of clothing options that women have. If they want to wear pants, they have all kinds of options there from jeans to silky and flowing. If they want to wear a skirt or dress, they can wear their hemline from the floor to just below indecency. If they want their underwear to show, that’s their option. What fun! And what control they have over men by what they wear!

I never really got much into full drag. I’ve mostly been just into wearing underwear and some feminine clothing that might tip off a woman to what I really am.

My need to be exposed to women as a crossdresser led me to massage parlors. The girls in these places would give handjobs to their customers. After some shopping around, I found the right girls who got into playing with me and feeling me up in my bra and pantyhose before giving me the “happy ending.”

Eventually I found one who became a little dominant with me and started fingering my little hole. The first time, I felt like a girl who had been fingered for the first time. “Oh my,” I gasped. “Yeah, you like that, dontcha baby?” I felt like I was being taken advantage of, and yes I liked it! Oh my goodness, it was as if my virtue was being taken away from me. You’re probably thinking, “What a priss!” Exactly.

Up until that time, I hadn’t experienced anything anal. When I was young, I used to put on girl’s underwear with the kid across the street, and he wanted to stick small things in my butt. I wasn’t much into it. But this was different. Now here was whimpering like a girl while this woman was jacking me off with one hand and finger fucking me with the other and talking dirty to me. “You like getting your pussy fucked like that don’t you? Don’t you?!?! You love it!” That pushed me over the edge, and I was cumming all over myself.

As I pulled my panties back up that first time I felt so dirty and naughty and sexy. What a girl! It wasn’t a week before I was at the adult bookstore shopping for a butt plug and a vibrator with an anal attachment. I was going crazy to have my little bottom penetrated again, and I was back at that massage parlor looking for that girl to “do me” again just like she did before.

I had made another giant step toward being a major sissy

Showing Off My New Bra

2008-01-04T14:39:00.000-05:00

Up until this point, even wearing pantyhose under my male pants was a risky thrill. I had been progressing to wearing panties and girdles under my drab attire. Somehow I reasoned, the world would know that I was wearing feminine underwear, and I would be forever exposed.

More and more, though, I wanted to be exposed. I particularly wanted women to know that I was wearing things they wear. Having bought a heavy padded bra from Frederick's, I would sometimes venture out wearing it under a thin, stretchy pullover top. Of course, leaving my apartment, I would wear a jacket over it, and I would be terrified that anybody would be able to tell that I had boobs.

Once I was in the relative safety of my car, I would take off the jacket and drive around with my padded bra showing through under the thin, blue top. I would feel myself up as I drove for hours. Sometimes at a traffic light, I would keep my arms down in the hopes that the two hot women at the traffic light would see me and laugh at me. It started to become an obsession.

Eventually I ventured out of my car. One night, I went into a small, all-night grocery store wearing my jacket. I browsed around for awhile, and as luck would have it, two college age girls were shopping that night. I pulled my jacket back and walked past them. They instantly noticed. They were a bit shocked. I continued browsing, then I got panicked. They were at the checkout when blew by them. I could hear them laughing as I walked out the door.

My face felt so hot from the embarrassment. It was like a high. I felt a mixture of shame and exhiliaration. I swore I would never do it again, but I knew inside I would.

My First Real Shopping Trip

2008-01-04T11:51:00.000-05:00

The first time I actually bought and tried on lingerie was a defining moment for me. By this time in my life, I had bought lots of things of things in stores either pretending they were a gift or adding them to other things like at a discount store.

I had hovered around the local Frederick's of Hollywood store many times. Just looking inside was a thrill. I had even gone inside browsing, but I didn't buy anything. A couple times, I had called the store and just asked the girl if they would have a problem with a guy trying on things there. She told me, no, it would be OK. Finally, I had to do it.

I was wearing a pair of pantyhose under my pants with no socks, something that at the time was pretty daring for me. I walked in and asked about a particular garter-girdle I was interested in. Back then, they still carried some girdles in the store. I must have been shaking when she showed it to me. Then came the moment of truth. I hemmed and hawed about it. And I finally asked her if I could try it on.

"Certainly," she said. She walked back to one of the back fitting rooms. OMG!! I was actually being led to the ladies fitting room to try on lingerie!! She placed it folded on a stool and said if there was anything I needed to let her know. I walked in and closed the door. This is it, I thought! I'm in the inner sanctum! I removed shoes and pants and started to put on the girdle. What fun!

The other clerk walked by, and she must have seen my stocking-clad feet. I could hear her quietly tell the other clerk with a chuckle, "He's wearing pantyhose." There was a bit of humiliation in that I really liked. I was admiring myself in the mirror for awhile when my clerk asked through the door if everything was fitting OK. I replied that it was fine. I realized that I didn't want to overstay my welcome, so I took off the girdle and got dressed.

I felt like I was walking on air when I walked out of the fitting room carring the lingerie I had just tried on. There were no other customers in the store. The clerk asked if I wanted to take that, and I said yes. Then I asked her if she would have a fully padded bra in a 36C. She took me over to the plastic drawers and looked for a bra in my size.

She displayed the fancy brassiere to me. It was quite delightful. I had never seen one quite that nice before. I asked to try it on as well and I was off again to return to my fitting room. This time, I removed my shirt and put on my bra and admired it in the mirror. I'd never had such a fully padded bra before and it was just wonderful!

I was giddy when I came out. "I like it a lot!" The clerk rang up my purchases, and I left the store with my Frederick's bag. Now I was a bit concerned of being seen by someone I knew. But somehow, I wanted the world to know I had just tried on a bra and girdle in the store! What a thrilling experience this had been!!

Let's Get Humiliated!

2008-01-04T07:36:00.000-05:00

Judging from some of the other blogs out there, I know there are lots of other sissy bois who love to be humiliated either in private or in public. I love sharing experiences. Almost from the time I first started crossdressing, I had the insane urge to expose my sissiness to others, particularly to girls who would laugh and tease me. Some of my earliest sexual fantasies involve being humiliated by the cheerleading squad. When I was in high school, I used to sneak around after school hours while they were in practice and get into their lockers (in our school at the time, not everybody had locks on their lockers), and I would steal their clothes and underwear. Then I would go home and put on their clothes and masturbate. My fantasies involved them catching me and dressing me up in front of all of them and humiliating me, forcing me to masturbate while they giggled and sneered at me. Of course, I was very careful that nobody found out that I secretly wore panties, bras, pantyhose, girdles, slips, etc. I had started from a very young age and started my own collection when I was in high school.

Of course, my girlfriend at the time didn't know anything about it, although I did try to drop some hints. I was president of a club in school and made up some story that we had to go through some hazing initiation wherein I had to dress up as a girl. I was hoping she would think it was cute and would share some of her clothes with me, particularly her underwear. I played out the story for some time. While she was sympathetic, she thought the whole notion was a little silly. She did give me some advice about things to wear.

I had told her that part of the initiation was that I had to wear everything including panties, bra, pantyhose, even a slip or possibly a girdle (girls wore them back then). She finally did give me an old half slip of hers, and I was in heaven! I told her that I was going to have to go shopping for a bra and panties. She was understanding of my plight.

That night on the phone, we got to talking about my shopping trip. By this time, I think she was a bit curious about my enthusiasm over having these things. As if conducting an experiment, she told me to put on the bra and panties, and then she asked me how I felt. I told her that it felt a little weird. Then I told her I had to confess that the panties felt very nice. Of course, I had worn stuff like this many times in the past, but I was getting a real thrill talking to my girlfriend on the phone and wearing a pretty new bra and panty set!

She might have sensed a little excitement in my voice. She was quite serious and said, “You know, some men do this.”

“What do you mean?” I asked, knowing perfectly well what she was talking about.

“Well, there are men who put on women’s clothing for a thrill.”

“Well, I’m sure there are,” I said.

She probably went on to explain that these kind of people need psychological help or something. I wasn’t paying much attention because I was quietly playing with myself.

Well, I changed the topic and we talked for another twenty minutes or so. Then I finally told her I was going to take off the bra and panties. She was totally shocked. “You’ve been wearing them all this time?!”

“Well, yeah, I was under the covers, and I had them on. I had to get up to take them off…” I was acting innocent about the matter. She was really disturbed that I would have left them on for so long while we talked. That just didn’t seem right to her. The poor girl didn’t know what to think. Here she was talking to her boyfriend while he’s wearing a bra and panties. Oh my!

I continued to seek out her help with suggestions for pantyhose. She told me about her favorite pair of JC Penney Subtle Shaper Pantyhose. It was a cheap thrill to be talking to a girl about pantyhose. I asked if I could try on a pair of hers for size, but no luck. She said I could just use the sizing chart on the package. It was thrill enough to open the package and examine the pantyhose that my girlfriend put on every day and then put them on myself! I continued to wear that brand and style for years. They don't make them anymore.

I got through my pretend hazing incident. Of course, I never went out dressed as a girl. Back then, I was too scared to go out like that anyway. The point of the whole episode was to tell my sweet, innocent, virginal girlfriend that, yes, I put on girls underwear: a bra, panties, pantyhose just like hers, and HER slip!

That was about the extent of my self-exposure during my high-school years. I was always afraid of being exposed to my parents.

BUT, there is MUCH more to come!!