Whatcha Gonna Do?

Decisions. 

Are you going to stand like a man and enjoy her service?

Or decide otherwise?

Be serviced... or give service.

For most men, the decision is easy. Belly up, close your eyes, and concentrate on her moist mouth. 

But you're finding your knees are beginning to buckle. 

Go ahead. Kneel. You know what you have to do...

Speaking of Squirting Dildos

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Role Switch With Squirting Strapon

I did a scene with an escort girl one time. She dressed up in my pants and shirt. Underneath she wore a strapon harness with an ejaculating dildo filled with milk. We played a scene where I was the hot secretary in the office. I was wearing a very short dress with black pantyhose, a pushup bra and very high heeled pumps. One thing led to another, and she was forcing herself on me. She kept feeling me up while I tried to fend off her advances. At one point I slapped her on the face for being so forward and rude. I was acting like a prissy stuck-up girl.

She blamed me for being a cock tease in my short skirt and sexy legs. Eventually she forced me to my knees and told me I was going to suck her cock. I told her I wasn't "that" kind of girl, but she told me she was "that" kind of guy. She put my hand on her crotch and made me feel her 8" cock. I kept trying to get away, but she forced me into the corner. She unzipped her pants and pulled out her cock. I kept trying to resist but she didn't give any choice, and like a frail little thing, I was afraid of being hurt so I did as I was told.

She pushed her cock against my lips. "Suck my cock, baby. Do it!" I shyly put it in my mouth, and she grabbed the back of my head and impatiently started fucking my mouth. I gagged and tried to get away, but I was helpless. I pulled it out long enough to demand she not cum in my mouth because I was a good girl. She said, "Don't worry, baby, just suck it." She shoved it back in my mouth.

I started stroking her big cock and sucked it like a scared little whore. She kept telling me what a good cocksucker I was. I kept stopping to tell her not to cum in my mouth. The whole time, of course, she had the sqeeze bulb for the squirting dildo in her hand. She sat on the bed as I knelt in front of her and serviced her big cock.

Several times I could taste the "precum" (milk) coming out the tip of her cock, and I told her again not to cum in my mouth. I was a good girl and didn't do that. She was a great actress and started thrusting her hips as her breath quickened. As she was about to "cum," she again grabbed the back of my head. I could feel the first spurt come out the head of her cock and hit the back of my throat, and I backed away in disgust. She held my head while she shot the rest of her load on my face. The bulb was pretty good sized, and she shot wave after wave of white cum on my face while I reacted in disgust.

I felt so used and dirty and cheap with all her jizz on my face. She told me my boyfriend should be proud of me for being such a good cocksucker.

For the finale, she had my jack off and cum all over the dildo. Then she had me get back on my knees and told me to clean her cock real good. I obediently licked up all her (my) jizz from the cock while she told me to swallow her cum.

After I finished cleaning all the cum of her cock, she put her hands on my face and sweetly said, "That's what you get for being a prick tease, bitch." She laughed at me and made me feel like a degraded girl. She put her cock back in her pants and left me on the floor like I was going to cry.

That was a really hot scene. I've played it over in my head many times.

Fucking With Heads

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

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?"

"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

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?

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

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...

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

Those aren't bike shorts!

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

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

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?

"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!

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

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!

This summary is not available. Please click here to view the post.

Nashville Part III

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

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

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!"