Monday, December 14, 2009

'Tis the season...

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

Friday, November 20, 2009

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.

Friday, October 30, 2009

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.

Friday, October 2, 2009

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!

Monday, August 31, 2009

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..."

Tuesday, June 2, 2009

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.

Wednesday, March 25, 2009

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.

Tuesday, February 3, 2009

You need to be penetrated!

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!

Tuesday, January 27, 2009

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!

Thursday, January 8, 2009

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.