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Confessions

Dress Confessions

Read the best #dress confession stories


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 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'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  


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 girl and I have a fetish for dressing up like a little girl and being fucked by an older man. I've always looked younger than I actually am and I really love the cute Japanese style (like Hello kitty, Totoro, Pokemon etc). I'd love to dress in all pastel pink and put a pacifier in my mouth and be a helpless little girl being raped by an older man.

Me and my boyfriend use to roleplay this alot. I'm a little girl who is lost in the dark, creepy streets. Then a man (my boyfriend) approaches me to come to his home, where its warm and safe. So we lay in bed and my boyfriend grabs my arms, pulls my hair, spits on me, bites my neck and fucks my roughly while I try to fight back and run away.


#daddy   #rape   #bdsm   #roleplay   #dom   #dominant   #sub   #submissive  


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 confess that my fetish is dressing as a sissy, I have so many outfits, wigs, breast forms, etc. I love to fish and know many places where I can fish without too many people around, but am always cautious. I love fishing in only panties and bra, so as I can get my tan lines set. Last year caught a few nice fish and poised for selfies dressed and holding fish and even put them online in a few places.
One day as I was waiting for it to get light, staying at motel along the highway, where the speed limit is reduced to 35 mph, was dressed slutty and was un-tarping boat, many truckers drove by and this sissy was in plain view for them to see. It was very exciting. I also dressed wearing a long fishnet pink dress, pink bra and pink panties with wig on, filled the truck up full of gas and drove home and on the way, stopped for an espresso, another thrill.
This sissy has been online searching for new outfits for this years journey. So looking forward to playing dressup in cabin and being displayed outside for all the truckers and fishing, looking like a sissy. Deep down, have always wished I were a female


#sissy   #dressing   #confession  


I'm a 50 year old divorced crossdresser almost my whole life. I love being feminine and am rather pretty. I love being a black c*** slut and have been since I was a teenager. My wife divorced me when she caught me in bed with two black men while dressed in her wedding gown and having sex. It's Sunday afternoon and 11 black men had sex with me this weekend and I love it the sex, shame and humiliation makes me the slut I am.


#crossdresser   #slut   #faggot  


Several months ago I met this guy online. We are both males, both married and in our late 40's. He put feelers out there as a feminine guy, wanted someone to meet while crossdressed and he wanted to be sub to a dom man. I'd not had any strange pussy or ass in over 20 years but was interested. We talked exchanged pictures and he started showing me pictures of his fat wife with huge titties and ass. He would even write my name on her while she was nude and take pictures to send me. I had some old pics of my wife and showed them to him.
We met, and started a fem/masculine get together in which he would dress and I would fuck him and dom him. He wouldn't suck cock though. I finally made him do it and he got mad and I finally got him back to meeting me. He had been fucked by 4 guys before me, I'd parade him around and call him slut, cunt, and other names. I would even open the drapes in the hotel/motel rooms so that people would see this chubby older woman getting banged in her butt through the window. They didn't know I was fucking a guys ass. I always started the session by making him stand up and stick my finger up his butt and make him walk around the suite, opening drapes, windows anything I wanted. He got really sub and I even more dom and I would make him do things to his wife, and take pictures to send me. She dommed him in real life (not sex life) even making him wear cotton panties all the time usually in pink, pastels, and white. So he wouldn't mess them up she made him wear a panty liner or a full pad, just as she did everyday. Sometimes she would make him wear a bra as he had cubby manboobs. Even when they first started fucking she refused to let him stick his cock in her mouth, or in her ass. So I told him he should take his wife and force the bitch to take cum up her ass or mouth. His cock had gotten to where he could barely get it up (usually with injections) so I wrote a story about her being passed out and my fucking her.
He started experimenting with her drinking and slipping in a sleeping pill. She would pass out and he took pics of him dildoing her cunt and sticking his limp cock on her lips. At his suggestion I waited till I got word from him that she was passed out and went to his house. I played with her for a while, ate her pussy out, let him play with my nipples, then I laid on top of her and she automatically spread her legs. Instead of fucking her then I just put my cock into her sopping pussy and got it really wet, then laid him down in his girly clothes next to his wife and fucked him right next to her, in the bed the two of them shared.
After that I made him do some kinky shit, and got my cock hard again, then fucked his wife while he placed my cock at her entrance. I shot a load up her slit all the while sucking, mashing and bruising her tits. I kissed hickies on her neck, and stuck the business end of a wine bottle up her loose cunt after I was done. I made him make me dinner, while dressed in his nightie with stockings and heels. Then told him it was time her virgin asshole got fucked by a real man. We went up to the bedroom and rolled her fat ass over, I made him grease her up with some lube she had and I got on top of her while she was lying face down on the bed. I put my cock into her, and reminded him that this was the position in which I first fucked him. After having shot two loads already, it took me about 45 minutes to cum up her virgin ass. It was certainly tight, I think she was indeed a virgin, but after a 45 minute reaming with a pretty thick 7 inch cock, and her being passed out, it was gaping open bigger than a quarter.
He started to panic wondering how he was going to explain the cum in her cunt and ass. I didn't give a shit and instead jacked him off all over her face and tits. I then told him that her cunt was way too loose for her to only be fucked by his scrawny little cock. She was having an affair. I then told him the best way for him to not be accused of fucking her while she was asleep would be to suck all my cum from her cunt and her ass, and lick his off her face and tits. Then I left. I don't know what he did, but it worked out.
I fucked her about 12 times that way, and finally he told her that he liked being fucked and dressing up and she liked the idea of him being a "woman" too. So he had permission to get dressed and fucked in front of her. I went and fucked him several times, then going off with her to the store, or out to eat (using his credit card each time) then I'd go back and get off again. She made him start sucking my cock to orgasm many times, and eventually she let me fuck her in front of him. She took my cock up her cunt, her mouth, her ass, she even did ass2mouth in front of her husband. I even made him clean my shitty cock with his mouth after it was in his wifes ass.
It's a very rewarding relationship, but we still like to get her drunk and passed out so I can abuse her cunt and ass and bruise those big tits of hers. She just laughs about it now.


#mm   #mf   #mmf   #drunk   #sissy   #crossdress  


Too often I find myself creating slideshows of women and girls wearing short skirts/dresses and masturbate to them. In real life, I'm just so turned on by short skirts that I often can't help myself whenever I see one. On top of that, if I happen to witness or find an image of a female curtsying in a skirt/dress or a panty upskirt shot, I get even more horny. And the weirdest part is that, for some silly reason, I enjoy jerking off to these pictures most when I replace the female's heads with an elephant's head. As someone who believes in Jesus Christ, I am easily able to recognize this as a habitual sin that I need to break because it often damages the way I look at the opposite sex when I see them wearing such attire.


#fetish   #weirdness   #pictures   #masturbation   #girls   #skirt   #dress   #panties   #elephant   #habit   #sin  


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


#crossdressing   #sissy  


I am a boy, late teens. I am not too big, not a jock, and girls never notice me. I finally got a girlfriend who is great for me. She is a bit of a fatty, not too big but about 5ft. 8in and weighs about 185. She was quite experienced in sex already, in fact very very experienced but I don't mind. I get to have sex in all ways, places and do everything I wanted and even more. She has red hair, and is 3 years older than me. She is pretty kinky in sex and I do whatever she wants so I can keep having sex. I rather like some of the kinky stuff. She has made me be the submissive one in our relations, she is definitely dominant. She has even taken me to a public beach wearing a girls bikini bottom and a collar with a leash. When we were walking back to the parking lot she moved me behind some trees and bushes and we had great sex then left. She even did it with another girl and let me be in bed with them, then insisted I do it to the girl too. The other girl was really totally lesbian and didn't want a guy at all, but my girlfriend made her do it, and made me do it to her.
About 4 days ago, she took me over her lap while I was naked and started spanking me, she spanked with her hand and then a hair brush for about 20 minutes I was in a lot of pain, my butt was red as a Crayola crayon. She then rubbed some lotion on my butt to soothe it a bit, and started sticking her fingers in my hole. After three fingers were in, she started fucking me with her fingers, I objected and she pushed me down and told me if I ever want to feel her ass, mouth or pussy again I'll just lay there and take it. She fucked me with three fingers for about 10 minutes all the while talking nasty and calling me names, saying I was gay and liked getting it up the butt. Then she stuck in one of her vibrators, and turned it on. Then she called me all kinds of names because my cock got hard. She fucked me with that vibe for about 30 minutes, then let me up, made me clean up "my" vibe, and put it in a special drawer. About two hours later she let me fuck her and I again had to lay across her lap endure an endless spanking, and a 30 minute fuck with the vibe. She then stuck in a plug. I had to go home, and she told me to leave it in until I came back, to take it out only when I had to sit on the toilet. I did it and the next day didn't see her until about 5 or 6 o'clock, by then the vibe was quite loose in my backside. We sat on the couch and were kissing, I was playing with her very big titties and sucking her nipples. As I reached under her skirt I felt something strange. I pulled up her skirt and there was a cock in her pants, she also was wearing a pair of my underpants. She stood up, pulled off her dress and then the bra and had me pull down the male underpants. She had a strapon cock and was wearing it. "Start sucking bitch" she almost snarled, "or get a real spanking not just one of those love paddles I've been giving you".
I was on my knees and started sucking the very large artificial cock. She made me suck for a while, then we went to the bedroom and she had some stockings and lingerie for me to wear. I didn't want to, but she kept reminding me of how much I liked sticking my "little wussy cock" into her pussy, mouth and asshole. As I got on all fours on the bed after dressing for her, she pulled out my plug and stuck the very lubed, very large strapon up my shithole. She didn't give me anytime to get used to it, just started fucking me, very rough, very hard.
This has become our normal sex now, she fucked me dressed up like a girl, and I jack off while she does it. She even had that lesbian girl who she made me fuck, come to watch, and she was wearing her own cock and fucked me too. The lesbian also took me home to clean her house, all the while, even riding in the car I had on the lingerie and just a robe to cover but it didn't cover my stocking'd legs and high heels. While there she spanked me and tied up my cock and balls very painfully because she said I raped her. My girlfriend says next week we're going to the beach with me wearing both halves of the tiny girls bikini.


#bd   #nc   #crossdress   #strapon  


When I was around fifteen I found some letters my mother and stepfather had written to each other. He was in the services and away a lot. They'd had two kids after she'd divorced my father and it was obvious to me from a young age that she really liked sex. The first of these letters described an incident that took place on a major train station after she'd seen him off at the end of his leave. Being a friendly person she'd struck up a conversation with a man who was waiting for a train. She described in detail in the letter to my stepfather how they'd talked for about thirty minutes when the man started to slide his hand up her dress and moved it towards her pussy. She said that she was so excited that, 'I couldn't help myself and I opened her legs so that he could touch my cunt that was wet from the fucking we'd done before leaving home. I almost came as his fingers stroked my slit, but when I felt my pants get wet with my pussy juices, I stood up and walked away.' I found a letter in answer to her from my stepfather who was obviously open to her being touched by other men and said he'd love to watch her being touched like that. As I went through their letters, I found out that they'd fucked each other in a public garden just after my father and mother had separated. He described how he'd loved how hot she was when he'd slipped her panties down to her knees and slipped his fingers inside her. Needless to say I was masturbating like crazy reading this exchange of letters. In another letter he said how much he liked fucking her ass and from the tone of her letters it was clear that he had a large cock which she really loved to suck and have inside her. It would be fair to say that she loved sex and was open to many aspects of it. I heard them fucking once in the middle of the night and one thing was very clear, she loved his cock and he knew how to make her cum and cum again. Her public face was very prim and proper but after reading their letters I knew it was just a facade as she liked nothing more than having a man inside her and the more often that happened, the more she liked it and the more I read, the more I liked the hot woman that she truly was. I masturbated often over those letters and guess that she always knew I was reading them but privately she didn't really mind


#mother   #panties   #dress   #upskirt  


I admit that i enjoy wearing women's lingerie and clothing,call me what you want but until you have dressed up in sexy lingerie and clothing then don't judge people,i wear lingerie under my work clothing. Panties bras suspenders stockings and when I get home i get rid of the male clothing and slip into something lacey silky smooth and sexy


#panties   #bras   #crossdresser   #lingerie  


I am obsessed with female clothing. Yes, I am a closet cross dresser. My girlfriend knows nothing about my cross dressing. We had an argument so I left and went into the city which is fours away. Taking one of my slutty cross dressing outfits with me. I had a room and decided to finally go out in public like the sissy slut I have always wanted to be. I went to a bar and was hit on right away. I hooked up with the guy and ended up back at his place. When he took his close off he had the biggest cock I had ever seen. I felt a strong sensation to suck it. He walked over to me and stood with his big cock inches from my face. I picked the semi erect mammoth and with out hesitation started sucking on it as if my life depended upon it.

When he had me straddle his cock so he could take my virginity. He also stroked my little sissy cock at the same time as I humped his cock. When he climaxed so did I in the most mind shattering orgasm I ever have had. I spent the night with him and found it hard to leave the next day. I want to be with him more than my girlfriend so I broke up with her. Looking forward to visiting my new lover and his wonderful cock.


#sissy   #slut   #faggot  


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 stayed at a female friends place one night. The room she gave me was empty except for an air mattress and for some reason, a pair of her panties. She knows I wear panties and am submissive so I asked if she would like me to make a video of myself jerking off in her panties. She said yes, do it. Now she says I have to give her the video but when I do she is going to show it to everyone. She said to make copies too so she can actually give away copies of it to make it more public. I'm going to keep my promise but I'm nervous. She says she has another video of me that's going to be added to it as well. She showed me a short clip from a hidden camera she put in her bathroom. She also said I'll be making more videos, this time she wants everyone to see me in a bra and panties or wearing a skirt. We have a deal that I can't say no to anything like that.


#nude   #humiliation  


I confess that I'm kinda fashion freak. The first thing I notice about another person is their style, what they wear, how they dress. I literally hate people who set no great store by dressing good.


#style   #fashion   #mode   #dress   #wear   #hate  


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.


#sissy   #blouse   #panties   #crossdress   #masturbate  


I have been married a long time, and when my Wife goes out, I dress up in her lingerie and clothing and go out to local adult video shop to have sex with other men. Most of the time I just give blowjobs, however on a few occasions I let them have intercourse with me and not use a condom. I enjoy being seen after having been used that way, and have their cum running out of me into my Wife's panties.


#gay   #homosexual   #crossdress   #suck   #swallow   #fucked  



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