Leotards and Tights

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

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

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

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

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

“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

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