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Confessions

Crossdressing Confessions

Read the best #crossdressing confession stories


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'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?


#prostitution   #crossdressing   #bisexuality  


When I was teenager home by myself I used to put on my sisters dress and wear my mothers lipstick. Later on I worked at a library wearing panties and nail polish. Now my wife has stopped wearing bras so I want to wear them, but don’t want her to know but I’m not worried if my daughter sees me in a dress for some reason. She’s just bought some bras and I wish I could bought some too.


#crossdressing  


Started crossdressing when i was in high school. Wore outgrown pants that were so tight that you can clearly see the outline of my legs and butt. My classmate commented that i look nice in them so when i got home i looked at myself in the mirror. and there i saw what he meant, my lower part is shaped like a girl's. That's when wore girls short shorts under my regular shorts when i ride my bike. Once i got far from our house, i took off my regular shorts and pull up my girls short shorts to make them a lot shorter. Now i get cat calls from guys when i buy groceries in my cute shorts. I got to taste my first cock while wearing my sexy outfits.


#crossdressing  


Like Confession #1445, i, too, have a fetish for long, straight, hair. Our confessions aren't just similar-they are copies.
When I was a young teen, my older sister (8 yrs older) briefly moved back home. When no one was home, I used to crossdress in my Mom's clothes. With my sister home, I started sneaking into her room and started wearing her more modern, stylish clothes. Think late 1960's-mini-skirts, tube tops, hoop earrings, etc.. She was a brunette and had two hairpieces. One was a beautiful, full, chocolate brown, shoulder length, page-boy wig with full bangs. The other was a nice fall, about 18", curled upward ala MTM. During the summer, when school was out, I was allowed to be home alone, sorta like latch key. Sometimes I would take a day home alone and dress up in make up, padded bras, panties, nylons, get into my my sister's clothes and her wig and then masturbate. My favorite was to dress up with the full wig and then jack off with the fall. The feel of the hair on my dick was/is just indescribable both physically and sexually. Intoxicating. And so it is to this day. I.m in my early sixties and still have a long, straight hair fetish. By happy (or perhaps, unhappy) coincidence to my hair fetish, during my life I was married to a certain woman for 25 years. It was dysfunctional the whole time in one way or another and we ultimately had no intercourse during the last ten years until divorce. That was 8 years ago. BUT... in that last 10 year time period, my sexual needs were meet EXCLUSIVELY with hairjobs. Ok, maybe a blow job or two. Anything but intercourse. She was glad to be let off the hook and I was now able to tune into a fetish I'd only dreamed about and so the bargain was struck. It was a match made in heaven (sort of). and lasted for about 8 or 9 years. I could and did get them whenever I wanted. And Sunday mornings were set in stone. Otherwise, I could either jack myself off with my wife accommodating me in various positions to put her hair on me or she would jack me off with her hair while I kicked back. .I am single now and retired and have a few "girls" who service me regularly. I have a small walk-closet with some wig heads positioned. I like to get stoned (I live in a cannabis legal state) and do some dressing up and retire to my fun room. I put on my favorite wig for the day and then jack off with my next favorite hairpiece.


#fetish   #hairjob   #crossdressing   #masturbation   #crossdress  


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.


#blowjob   #crossdressing  


When I was younger (I won't say how old) I used to talk with older gay guys online. I eventually started taking pics and even taking requests for what they wanted to see. A few wanted to see me in panties so I would swipe from my sister's dresser and put them on. I guess they looked good because more and more guys wanted to see it. Eventually it led me to buying a wig and putting on my sisters clothes & makeup for them. It then went from pics to vids of me stripping and masturbating for them. Thinking back now about it turns me on so much. I often times wish I was a girl.


#crossdressing   #bicurious   #sissy  


Yesterday, I was shopping at JC Penny's and went into a fitting room to try on some jeans. Someone before me had left a bra hanging there.
I couldn't help myself and I put it on and wore it home. I'm a guy.


#crossdressing   #bra  


I am a secret crossdresser and when girlfriend is out I go to my garage and bring out my bag of lingerie.
I have a satin fetish and love the way it makes me feel. I get dressed up in black satin bra and thong, suspender belt, stockings and a black satin chemise. I then have webcam chats with men admitting I am gay and they tell me what a sissy I am.
Once I am finished I always feel a bit of shame and consider telling my girlfriend the truth but always end up putting the bag back and wait until the next time I am alone.


#crossdressing   #gay  


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.


#fetish   #panties   #crossdressing   #humiliation  


I have been a closet cross dresser since age 11. 30 yrs later I still love to dress up as a girl (preteen to late teen styles) As I have gotten older I have only grown to love dressing up more and more..staying fully dressed as a girl for a week which I find myself acting like a young girl. I am always buying hosiery dresses,skirts as my girl wardrobe has surpassed my male wardrobe by far.


#crossdressing   #transvestism  


Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.


#crossdressing   #panties  


I am a 25 year old male and I fantasize about being dressed up like a little girl. I would give anything for someone to feminize me.


#fetish   #crossdressing   #transgender  


I love to dress up like a woman and rub my self in my lingerie.


#crossdressing   #sissy  


Well a lot of my ‘sins’ began back when I was 14, I am 16 now. Then I would post a lot of pictures of me online on reddit claiming to be 18. I loved the attention from the guys and girls I got because I didn’t feel comfortable with myself and they actually liked me for me. They loved my body and made me confident in myself. I loved wearing girls clothing and began stealing cloths from my sister and aunt, trying on anything that I liked. I would show pictures of me masturbating, or ones of me twerking, trying new things, everything, I loved being a little slut like that. But eventually I calmed down on the whole posting thing as life took its toll on me and I couldn’t keep up with it. But that didn’t me from getting kinkier. I went deeper and deeper into the web, finding all the craziest of shit.

But one thing I did that I really loved was when my aunt and uncle were out of town, they had my house and dog sitting so I had free rain of their house. I went into their room and began looking around for toys, but wasn’t able to find anything. I did find some dirty underwear I played with and eventually came in. But also I went through their closet and tried on a bunch of her cloths as I loved them. At one point I was dressed in a pair of sexy thong panties, a lacy matching bra, silk teddy and silk robe. I’m not crazy chubby, but my chest area kind of looks like I have boobs even though I’m a boy so they fit her cloths perfectly. I took one of their dog collars and put it around my throat and painted my lips and put lipstick on. I jerked off everywhere and came in a bottle of her lotion. I then also used random things I found around the house as dildos as I’m pretty brave. But also, I wanted to try something out, so I took one of the male dogs to the bathroom and I began jerking him off. I then also began to suck him off, but when it tried to get him to fuck me he was too small and didn’t seem interested. That’s definitely a dream of mine, to be fucked by a big hung dog…

But that was my confession, hope I’m not too much of a weirdo for here…thanks for reading if you’ve gotten this far


#femboy   #confession   #young   #teen   #beast   #posting   #crossdressing   #incest   #sneaky  


I'm a straight guy but I have to confess that since I was 14 I took a interest in sexy lingerie and began secretly dressing in it. My wife thinks she got me into it 9yrs ago so I let her think that. So I have really been wearing women's clothing for nearly 20yrs..I feel comfatable and relax in female clothing.I wear lingerie every day under my work clothes. At home I get around wearing either a nice dress or a nice skirt and blouse


#crossdressing  


A while back, after a breakup, I had been using phone sex services regularly. I usually used Femdom providers.
One woman I called kept telling me I needed to get peach colored lipstick to give blowjobs. She figured had a slutty alter ego.
After using her regularly, I got a notification for registered mail waiting at the post office. I got the parcel and opened it up in the car. It was a pair of silky panties and a note from the provider. I called her later that day and she made me put on the panties and lipstick and promise I’d suck cock.
That started my secret fetish. I dress up in stockings, 4”heels, and lingerie and act as a cock hungry sissy slut.


#crossdressing   #sissy  


I like to crossdress very much and wish to have sex with males and have fun like a woman.


#crossdressing  


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.


#sex   #crossdressing   #blowjobs  


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.


#sissy   #crossdressing   #pantyboy  



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