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When I was a teenager way back in the early eighties, I was taunted by some of the other boys at school for being overweight. I was a little, but in my mind at the time I was convinced it was a lot. It got to me so much that a few days before the start of the new school year I went into town with some money I'd been saving and (I can still barely believe it even after all these years) I went into a department store, went into the lingerie department and, with a bright red face, bought myself a panty girdle. Even though I dreaded the thought of wearing it, I thought a girdle would reduce my belly, tighten up my backside and get the bullies off my back. As I was excused gym class on medical grounds, there would be no problem there. And surely I'd get used to it? The assistant was initially astonished and thought I was joking at first, but when she realised I was serious, I guess she figured my money was as good as anyone else's.
So, on that first day, I headed off to school as if everything was normal, went into some derelict buildings along the way, took off my trousers, quickly tugged on my long-leg Playtex "I Can't Believe It's A Girdle!", got dressed again, and headed off to school, wide-eyed and stiff legged. My "weight loss" since the start of the summer break was noticed, but I was still bullied. And now I had to get used to wearing a tight girdle every day to maintain the weight loss illusion - I could hardly get paunchy again overnight!
Have you ever had that terrified sinking feeling in the pit of your stomach when you realise you've really screwed up? That's how I felt when it dawned on me what I'd done and that there was no going back. The whole idea was dumb from the start, had failed totally in its objective, my initial overconfident attitude about getting used to it had died the moment I'd put it on and realised as it compressed my belly, backside and thighs exactly what it was I was going to have to get used to...and now I had no way out! I felt sick as I realised I was going to have to wear a girdle - a Playtex panty girdle! - every day from now on. For no good reason. And it was all my own damn fault.
By the end of that first day of being firmly held in, I could definitely believe it was a girdle! I'd fidget around in my seat trying to get comfortable - sit forward, sit back, legs apart, legs together - but I could get no relief. It was a girdle, and it did what a girdle was supposed to do. I'd catch myself gasping as I stood up or sat down, and walking up or down stairs was...an experience. By lunchtime I felt like I just wanted to scream, but I had a long afternoon in front of me before I could take it off.
After school, I hurried back to the derelict buildings (as quickly as I could manage!) to get out of my tight new panty girdle. I was almost crying with frustration as I fumbled frantically with my belt buckle in the rush to get my trousers off and get the bloody thing off me. The relief I felt as I peeled it off was incredible. But I just had to get used to it being part of my uniform from that day on. I'm not ashamed to say that, as I tugged it on the next morning, I was actually crying. I did eventually come to terms with the situation and get used to it, but it did take a very long time.
I guess that was about the only notable thing I achieved at school, though being the only boy to have his underwear made by Playtex is something I was quite happy to keep secret!
I had been out of town for a month and getting desperate. I was in New Orleans, and walked past a tiny little bar and decided to go have a beer. As I sipped my beer I noticed a small, rather shy looking girl at a table all alone next to the dance floor. I kept watching her, she had a yellow sun dress on, and small boobs which I like, and very nice, shapely legs which I LOVE. I didn't see her butt, though all in all, she was looking pretty good. I saw some guys come out of a door at the back of the place, then a couple of what could only be crossdressers. Oh well, New Orleans, and live and let live. Then I noticed a butch patron and the bartender were a guy in drag, and a super butch lesbian. I figured it was a safe bet that the object of my immediate lust was a CD. I bought her a drink, sent it over, and then asked if I could join her and she said yes. She was definitely a He. Not being gay, but very desperate to have someone to have sex with other than my hand or a paid masseuse, and her being actually very pretty with a very feminine petite body, I started talking. She didn't want to talk much as her voice gave her away, but she was still pretty femmie sounding. After several hours, and a burger each for us, I made her stand up and start slow dancing. She was shorter than me, about 5ft. 8in, with a very thin body. I put both arms around her waist and as we danced, I went towards the corner and with her back to the corner and no one seeing, I pulled up her dress in the back and stuck my hands in her panties. She protested, and I wouldn't stop. Finally she said "Back Room" , I didn't know what that meant, but she advanced to that door at the back showing everyone my hands were on her bare ass. It was a totally dark room. "We can do whatever we want here" he/she said. So I pulled up the dress and pulled off the panties and started groping her ass. Kissing and licking, and rubbing, she asked if I wanted to do it there. I said no, I wanted her in my hotel room. Instead she said to go to her apartment which was only a block away. So I put the panties in my pocket and saw her moving what must be her cock between her legs, and we walked out, paid the tab and left, with the patrons wishing us a very sexy and good night.
At her place in subdued light I could imagine myself with a girl not a guy. I like buttfucking girls, so this should be no different. I got the dress off, kept her bra on, and with no panties saw her little cock a little bigger than my thumb, that was all. . . and it was fully hard. I pushed her down on her knees and she began sucking my cock, I told her to suck my cum so I could last longer when I fucked her. She was excellent and I was cumming in about 10 minutes. She the laid me down, got some oil and gave me a great massage for about 20 minutes ending up with her using the oil and getting my cock hard again. I pushed her on her back and got between her legs and kissing her, stuck my cock in her cumhole. It was very loose with all that oil, and I'm sure because she'd been fucked by a LOT of cocks in her time. I fucked her for about 30 minutes very rough and hard it felt like I was fucking a pussy, not at all like the girls butts I'd fucked. I rammed my cock up into this little cum bucket and flooded her with my cum. Adding to my 8inches I'm guessing I shot hard enough that it went over a foot up her poop chute. Exhausted I rolled off her and lain next to her. She moved my hand to her little cock which we called a clit and asked me to suck her. I told her I didn't suck, actually had never done it with a guy. She gave me the oil and told me to use my hand and help her out, and in her most feminine manner said "A good lover makes sure the girl cums too!". So I did. I actually gave a cock a hand job. When she was shooting I had moved my face close to watch, I did lick just a couple of drops off my hand. With that done I stuck around and fucked her ass one more time this time her on her belly and I left.
We met a few times in the next couple of weeks, and she finally got me sucking her little thumb sized clit, till she'd cum in my mouth. I don't mind so much. Last night we went out as two guys, and I fucked her all night at her place, stayed over and woke up to a smooth, girl in lingerie for my morning fuck. Then she rolled me over on my belly and got on top of me.
It's amazing what being desperate can do for what I used to think was the straightest guy on the planet.
Back when i was 14 i would crossdress for older men through kik. I once found my teacher on there and i never told him anything but he was my biggest fan.
When I was about 13 I sneaked into my younger sister's room and looked through her wardrobe. I found this blouse that I didn't remember ever seeing her wear, it was a pink satin slip on with a round peter pan collar placket and short frilly sleeves. It was so ultra girly that she'd probably never be seen dead in it. I'm not sure why but I sort of dared myself to put it on even though it was far too small. I had to put my arms really close together inside it and put my hands into the arm holes. Gradually I pulled it down until finally I had it on. Then I did up the buttons one by one, right up to the top. I couldn't believe how sissy I looked in the mirror, or how hard my cock was getting. Looking through her drawer, I found a pair of short pink nylon pyjama panties with flowers on them. Trembling, I put them on over my hard cock. The feel of them hugging my ass was amazing. Finally I put a pink skirt on to complete the outfit. Seeing myself dressed as a little girl in the mirror was too much, I masturbated like crazy and came half way across the room.
I'm a 65 year old bisexual male who loves to cross-dress. I've been doing this now for seven years. Wearing women's clothing just feels so good to me. When I get up in the morning, I can't wait to get my entire body shaved completely smooth, put on makeup and do my nails. Next comes my thong, corset, push-up bra, hip and butt pads, garter belt and nylons. Since I've been taking phytoestrogen supplements the whole time, my boobs have grown to fit snugly into a 42C bra. My boobs are really nice. Guys go crazy for them. I began using breast forms to augment my appearance, but I don't need them anymore to get a nice effect. I really love my boobs and fondle them as often as possible. Next comes a silky slip to drape over my torso, followed by a sexy dress with its hemline falling just above my knees. The neckline of my dress must plunge low enough to expose my cleavage. My legs have received many compliments on their shape, so I always wear a fashionable pair of heels to bolster their appearance. Earrings, necklace, bracelet and a nice wig complete the look.
My wardrobe is extensive. I have dozens of dresses, skirts, blouses, shoes. outerwear and accessories. Wigs of all shades and lengths are available to me as well. No matter how much I have, I can't resist the urge to buy more. Its definitely an obsession. When I'm fully dressed and see myself in the mirror, I nearly come to climax. OMG, how I wish I could be a woman. I'm so jealous of those who are.
Being bisexual, I crave having sex other men. As a younger man, it was relatively easy to hook up for same sex experiences. However, as I aged, it became harder to arrange such trysts. Becoming a crossdresser definitely increased my chances for success. I discovered that many men love "chicks with dicks". It opened up a whole new world for me. As soon as I began appearing in drag, I became much more desirable. My date requests grew immensely. I could pick and choose which ones to accept.
One thing I've always fantasized about was being a prostitute. How lucky women are that they can do this. I could never understand why more ladies don't participate in that occupation. I fantasized about it so much, I decided to try my luck as a crossdressing escort. Websites for escort service advertising are all over the internet. I offered my services on as many of them as I could. I really didn't know if I'd get any responses. To my surprise, the replies were overwhelming.
It was so easy to find men who wanted to have sex with me. There were several women as well. I've lost count of how many men I've sold my body to, but it has to be at least several hundred. Age range also surprised me. The youngest man I did told me he was 18, and I'm not sure if he really was . He looked no more than 16 and didn't have a car. I asked to see his ID, but he declined to show me anything. I probably shouldn't have had sex with him, but the opportunity was too irresistible. The oldest guy was in his 70's and the rest were part of every age group in between.
So far, I've made tens of thousands of dollars over the years as a part-time prostitute. I know its not the right thing to do, but I just can't stop. I've tried to quit many times. I love the work so much the idea of quitting is to depressing. I can't keep doing this forever. What am I going to do?
I am a 24 year old male and I absolutely love to wear women's clothing, lingerie, panties,bras, skirts, etc. I love to wear Hello Kitty, Disney Princess and Victoria's Secret Pink panties. I am completely obsessed with wearing girl's clothing and have done it since I was 16. I love women's clothing and I wish I was born a girl. I am jealous of women for getting to wear those clothes all the time.
I'm a 25 year old male and I once paid a girl to dress me up in her panties, bra, miniskirt, high heels, and a blonde wig and then laugh at me and taunt me. It was so humiliating but soooo hot.
I want to dress up in pretty lingerie and go to a party with other guys wearing pretty lingerie. I'm straight but want to touch a hard, panty covered cock. I want to make him cum.
#panty #crossdress #sex #confession
I guess I asked for it sort of. She ordered me to make a video last night. I was told to set up my video camera in her room. Go in and strip right in front of the camera and start jerking off. Then pretend to steal the panties that she just took off. I had to put them on and jerk off. Just before I blew my load she came in a "caught" me. Now she's telling everyone she actually caught me in her room and is GIVING copies to our friends.
I am a thirty five year old man who by day seems like a pretty typical guy. But, I am closet gay and cross dresser. No one knows. I dress in panties, bras, stockings, high heels at home. When I dress, I become effeminate -- prancing, swishing, the whole bit like a silly little girl. I find it completely liberating and relaxing at the same time. Once a month, for fun but to keep anonymous, I get a hotel room and seek guys online. I dress up and host men -- it turns me on to host as many as I can in one night. Current record is 6. While there is no money exchange, I do feel like the scene is very much a prostitute (me, dressed like a dirty whore) and Johns. When I service them to completion (mainly blow jobs but I do enjoy penetration), they simply leave. I am usually on the floor in my panties/bra, covered in cum, but still horny for another man's penis.
I have a long straight hair fetish. Whenever I encounter a younger woman (the younger the better with long straight hair, I get aroused sexually. This usually ends in my going home and masturbating while thinking of the girl.
Over the years of having this fetish, I have attempted to satisfy it by buying several wigs of various styles. At first, I only played with them but this resulted in me trying them on and masturbating in front of a mirror. Eventually it led to cross dressing but only as a younger woman. I would purchase younger clothes and mimic the young girls I often saw in public places.
Now, I am taking this CD thing to the next level and going out to CD friendly public bars. I dress as a young woman in very conservative clothes and try to fit in. But in the end, it is all about the hair. Long straight hair falling around my face and down my back. Bangs are a plus with me and if I can style them with a deep sidepart, all the better. I cant get enough of this fetish and often wonder what will become of it. The only positive thing is that I am not hurting anyone and am keeping it totally to myself. My biggest worry is getting caught.
I'm a crossdresser, and have been for over 20 years. A few weeks ago, I met another crossdresser and we sucked each other off, the first time I ever sucked a dick. Since then, I've sucked two more, and I want more. I love it.
I started dating this really skinny girl in a city I was working in for 6 months. She was skinny, with short black hair, a nice looking face, somewhat of a tomboy I thought. She was living in the city full time as opposed to me. After about 4 dates she finally admitted she wanted to have sex but had no boobs whatsoever, and knew most guys were really into big boobs. She also said that since she was young, and even before she ever had sex, she'd had guys and girls tease her constantly. Some guys wouldn't even go ahead and have sex with her because she had a totally flat chest. She also said she was a little kinky about sex and liked normal things, but only if she could have it lead to some other stuff she really liked. I told her I was very amenable to trying new things and simply would say if I didn't like it. She then asked me about her lack of chest and I told her that I didn't think it would be a problem. She told me to stop where we were going, to order in some pizza and go back to my apartment.
She made me order, then had me strip, and went to the bathroom and came out totally naked. She did indeed look like a boy. Small frame, no hips, very little take-in at her waist, nice roundish little butt though, and this big patch of very thick hair on her pussy. I didn't say anything, just pulled her over to the bed and she asked me not to mess with her nipples as it made her feel bad. So I kissed her, and she reluctantly kissed me back, I reached to feel her pussy and found a 2" clit that looked just like a small uncut penis. As I rubbed her it grew to three inches. I'd never encountered that before and I loved it. I finger fucked her and she had me roll over on my belly and got on top of me and ground her clit into my ass crack. She started kissing me in earnest, as I craned my neck to her lips while she was lying on top of my backside pumping for all she was worth. She was bucking back and forth and I told her to stop a second and reached back, spread my legs and my buttcheeks and told her to put it in my butt. She used her pussy juice as lube and got her clit about 2 inches up my hole. She fucked me like crazy and even came twice. The doorbell rang and she jumps up I thought to go to the bathroom and hide, but instead she put on one of my tee shirts and a pair of my underwear, my tennis shoes and answered the door. She looked just like a guy.
She came back, got pulled off the underwear and said "I guess you should have a turn before we eat" and let me fuck her pussy in missionary position, again her kisses were very shallow. We ate with her wearing the tee and my underwear and me wearing nothing. When we went back to the bedroom she kept on the underwear and shirt, and had me kneel on the floor while she stood up with her clit in my mouth, sticking out of that super thick black pussy hair. She came again, and then she did the same to me. I loved it she sucked really good. Then she bent over with her arms on the bed, standing next to it, pulled down the boys underwear just below her ass and inserted my cock into her ass. She and I both loved it. It was my first time fucking an ass.
So after a few weeks she now dresses 90% of the time as a boy, and we spend equal amounts of time getting buttfucked. She likes to keep on boy clothes and be a "gay guy" and get buttfucked. Even when I fuck her pussy it's mostly from behind. She fucks my ass too.
I started dating a girl, and ended up in a gay relationship with her. . . him.
But I still like it. It's not normal that's for sure. I don't know what I'm going to do when I have to leave. I really like this situation
I'm a married man. Love my wife. Also have a guy who is bisexual just like me. He loves me and i love him too. We have crazy sex when ever we meet. He considers me top but I'm more of bottom slave. I like to be roughed up. He makes me feel good. Lovely person.
#gay #married #bottom #slave #crossdress
I am a married man in my 50s and have been crossdressing since my teens in secret. Last year my wife caught me and ended our sex, exiling me to the guest bedroom. Late at night now I surf porn and craigslist. I recently hooked up with another married guy in his 50s, dressed in a slip and bra and sucked his cock. It was my first time but OMG I loved it. When he held my head and shot his load on my mouth I got so excited I leaked a little cum. He just texted me to come by and wants me to wear his wife's clothes. I am so excited.
I'm a 31 year old married man with 2 kids. I crossdress, and meet men to give them blowjobs often. I also go to the adult bookstore for orgies and random gay sex.
I'm a 16 year old male (for real; I'm not trying to bait anyone, or anything). I've always looked somewhat feminine, taking a lot more after my mom than my dad. When I was younger, I was even occasionally mistaken for a girl. That said, I'm a junior at a fairly progressive high school, and in my Drama class before Winter Break, I played the role of Juliet in Shakespeare's Romeo and Juliet. My Drama teacher is sort of weird. He's also VERY particular about the craft, so I was fully costumed and wore makeup the day of. To top it all off: it was a kiss scene! Now for the confession: my partner, playing Romeo, wanted to do the "thumb trick", where I would end up kissing his thumbs instead of his lips. I said okay, but when the kiss happened at the climax of the scene...I moved his thumbs away! He was really embarrassed, and so was I, but in the moment I felt really compelled to do it. I tried to apologize afterwards, but he just dismissed it...I'm not sure what to do now...
#juliet #shakespeare #drama #highschool #romance #crossdressing #embarrassed #dress #makeup
I was an 18 year old, discrete crossdresser. I stole my aunts high heels and my cousins gymnastics leotard and gave head to another man. I felt sexy as fuck.
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