No subscription or hidden extras
Read the best #dress confession stories
I was 15 when an older cousin told me we could go to this older mans house and he'd blow us and give us each $10. I refused several times, but once after 3 beers I was ready. I'd only masturbated before other than at age 8 through 10 played with my cousins pussy. I was very apprehensive going into this place and didn't want anyone to see me. We got there and this long haired guy of about 40 years or so gave us some beer, some pot, and my cousin dropped his pants and sat in a chair across the room from me and the man got on the floor between his legs and gave him a blowjob. After my cousin said that it was my first time, so the man told my cousin to leave and he'd get me home.
"You a virgin" he asked me and I told him the truth. "Stay here I have something special for you, will you wait for a few minutes?" I said yes, and I think he didn't believe me he said he just wanted a taste and made me take off my clothes and sit down and put my cock in his mouth. It felt great but he stopped. He took my clothes in his bedroom and told me to wait.
When he came out SHE was totally dressed sexy as hell. She had on make up, a sexy nightie, stockings and styled long natural hair. "I'm going to take all those nasty little virginities away today." he/she said in the most feminine voice you could imagine. She turned down the lights, drew the drapes, and took me naked to the bedroom.
While there she first blew me, then kept playing with me until I got hard again, and I was rubbing his/her ass, and found out that she had small little titties. They actually filled out her A cup bra. They were nice and natural, very soft, with puffy nipples. "Hormones" she said, "You like?" I told her yes and my cock was hard again as I was sucking on "her" titties. I was playing with her panties sticking my hand down them like there would be a pussy, and she had a tiny little cock which she made me call her clit. It was pulled between her legs and her perfectly trimmed pubic hair really made her look like she had a pussy. I was rock hard now and she pulled me on top of her while she was on her back and spread her legs. "Look at me baby" she said as her hand slipped my hard 8" cock into her soft, willing ass. "When we're like this it's my pussy, when I'm on my belly it's my ass" she explained. "You like my pussy baby?" I replied it was wonderful and she started rocking back and forth and I picked up on the movement. I was sucking her tits, squeezing them and when I was about to cum I couldn't help it I kissed him/her. Her tongue danced inside my mouth and I rammed it into her and shot a mega load of cum (at least 10 to 12 ropes) up into her manpussy. Kissing me in her afterglow like a woman would, I kept my cock inside until it grew soft and slipped out. With that I rolled over next to her. We kissed, I played with her clit and those really nice soft titties.
She pushed my had down to her clit and I didn't want to be a "faggot" and suck cock and told her so. But she told me that she'd done everything for me, and now it was her turn, and I needed to learn to let the girl cum too. I made her promise that she wouldn't tell my cousin that I'd done this, and she promised. I went down on her and started sucking her cock. She blasted a tiny load in my mouth and I swallowed it all.
After that we both relaxed in the living room a bit, with another beer for me and some pot for us both. It was really strong pot, and I was lying down on the couch with her kind of behind me and I felt her finger rubbing something wet on my butthole. She was lubing me up, stuck two fingers in and it actually didn't hurt too much. In my stoned state it was pretty good. I didn't say a word and she whispered that no one would ever know but I had to lose all my virginities and this was the last one. She fucked me with her tiny little clit (about the size of my middle finger) and came in my butt. I got up to go to the bathroom to get it out of me and when I came back she was lying on the bed on her hands and knees, with her panties down her leg with her ass up in the air asking me to fuck her in her ass. I did, I came, and she gave me my clothes along with $100. She said I could come back anytime, and I did. I must have gone to him/her at least 150 times in the next year or two. Maybe more. Some weekends I'd fuck her all day long. I actually let three (1 at a time) guys who were over to see her fuck me, and I sucked at least 10 cocks for her. She paid me each time, but I think she charged them, I was never sure and didn't care. I got to fuck all I wanted and she was a gorgeous woman when dressed and made up. It was 4 years before I managed to get a real woman to allow me to fuck her.
#crossdresser #mm #virgin #anal #oral
I've always had a panty fetish but last year I developed a new one. My sister was getting married and I found her wedding dress and lingerie at our parent's house. A month later I was at my sister's house babysitting and after the kids were put to bed I started searching and found her wedding dress hanging in the closet. I remembered it being so soft and decided.
I was so horny yesterday and hadn't had sex in a long time. I found a twink online, went by his apartment and was fully intending to fuck him with a rubber on, but instead ended up with my dick in his mouth, then bending him over and giving his asshole a creampie. As I pulled out, it was leaking out of him, I'm normally not a big cummer but this was probably the biggest load I've ever shot. I hurried up and wanted to leave, he talked me into staying for a bit, I got a beer and we talked while he had some straight porn on the TV in his bedroom. His ass was pointed up and his hole was gaping open with my cum leaking out. I fucked him again, he tried to jack off his little dick but I wouldn't let him. I kept pulling his hand away, rubbed his pubic bush, and his nipples like I would a girl if I was fucking her in the ass.
I hate the fact that I did it to another guy. He was dressed in stockings, garter, a camisole which was like a small bra up top, he had very long sexy hair too and was in full make up. But still I fucked a guy and let him suck my dick. I shouldn't have done it, but I needed to come so badly.
#mm #crossdress #homo
I am a long time crossdresser who now fantasizes about having sex with an older man. I would love to dress up in a slutty skirt and top along with a sexy bra, panties, stockings and high heels. I would be completely made up as a woman and try to be as sexy as I could. I would then like to meet an older married man in his sixties who would take me home to his place. Perhaps his wife was on a trip and he had the place to himself. We could have a drink and then and then engage in some long lasting foreplay so he would get really turned on. I would let him take me to bed and I would suck his cock for a little while until I got on my back and opened my legs to fuck. It would feel wonderful to feel his cock in me and have the weight of him on me. I would wrap my legs around him and wiggle my ass to the rythym of his cock going in and out. When he came it would be an explosion of hot cum in me and would feel so good. If his wife was going to be gone for a while I would try to stay there and fuck him as much as I could. It would be our little secret and his wife would never know about the hot fucking that took place in her bed.
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.
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
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 have cross dressed since the age of ten. I still do in privet, now days. I have always wished I had transitioned to female when I got out of high school or by the age of thirty. Then find a hansom Man with a large Cock to marry me for life. I would be his wife and service his every need. CK
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.
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 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
She loved to embarrass me and dominate me. On one particular night, I went to the bar with her and her gorgeous room mate. At the bar I was playing pool when she decided to distract me by grabbing my balls when I bent down. Suddenly I realized she was letting other girls do it too and I had no say in it. I was groped by every girl there nearly. When we got back to her place, her room mate went to bed but left her clothes in the bathroom. I had to wear them and risk being seen by her room mate. I managed to avoid being seen but had to pose for pictures dressed like that and completely nude, which she left where her room mate would find them and take them. What a night.
#crossdressing #femdom #embarrassed #cfnm #bra #flash #panties #public
I used to ride motorcycles alot and I always wore these tight black leather pants with boots. Usually I was out late nights barhopping. Some nights I scored pussy. Some nights I scored none. One night in particular I was out late. The time was about 4a.m. I had not gotten lucky that night. I noticed sitting at the bar was a thick redhead woman. The stool next to her was empty. I sat on that stool and continued my beer. Said hi to her and as natural began the small talk. We sat and talked a few minutes. Now I am a tall slender guy of pretty good looks. She was not bad looking at all.I guessed her to be mid to late 40s. I was late 20s. She had on a short black skirt with nice thick legs. Her makeup was impecable. She offered to buy me a beer and I accepted. As small talk continued I noticed her hand on my thigh. By this time my dick was aroused. Her hand rubbed towards the inside of my thigh and not too far from my bulge. She then proceeded to tell me she was a boy. Well now, what do ya do? Excellent tactic; look just like a woman, buy a guy a drink and then get his cock all worked up. She knew what she wanted. Now in this town it was not unusual for sissies and drag queens to frequent the bar scene. There were quite a few clubs that featured drag queen lip-syncing shows and contests. So I was not shocked. In fact I felt complimented. Well one thing led to another I wasnt getting any pussy that night but I was curious as hell. On my other side sitting was an aquaintence of mine. He leaned to me and asked what her story was. I told him she says she is a boy. He was like," Really? " Well she looks over at me and tells me is heading out. I told my buddy that I wanted to go see what this was all about.
So I left with her and followed her to where she lived. She shared a house with a few other people; one of whom I knew but he did not know I was there. W went up to her room. All feminine. Nothing boyish at all. Well I was nervous in a sense. My cock was raging hard. I had no idea what I was gonna do. She wasted no time removing her blouse and bra. She had really nice big tits. She laid on her bed leaning on her right elbow. I just paced. She told me in her raspy voice,"I wish I could get you out of those leather pants." I acted as if I did not really hear that. We exchanged more chit chat and she rubbed the bed next to her and said it again. Finally I had enough. I caved. I walked up to her bed.
"I know what you want" I said to her.
"Oh?" she says.
I proceed to unfasten my belt and unsnap my pants. I pull down on my zipper. She begins to start gazing at my crotch. Now I am no small boy. Not John Holmes but larger than average. I pushed my pants to my knees and my cock appeared.
"Ooooh! Nice." she says as I sit down next to her and lean back. My cock was stiff against my abdomen. She reached forward and wrapped her hand around it. She then began to lean her face forward as she slid the head in between her lips. She began the up and down movement that comes with a gurl sucking a big hard dick. All I know is this was THE BEST blow job I had ever received. She continuef about 10 minutes licking the head, kissing the head and running that tongue up and down the shaft while massaging my balls. I was amazed at how good she looked and how good it felt. I soon felt it coming. She sensed it as she raised up and let the cum shoot onto her face. Another shot went on my shirt. As it shoots out she again goes, "Oooooooh!" The deed was done. My first drag queen blow job. I saw her again a few weeks later. We barhopped together one night. She was my date. People in the bar scene knew I was not gay and if you were out with her you were considered lucky because you were getting sucked off. The night ended. It was morning. She drove me home. We sat in her car and talked. I couldnt stand it. I looked at her, "You wanna get me off?"
"Oh yes."
I raised my hips and lowered my pants. She sucked me to orgasm. It was exciting because of the daytime risk of being seen by neighbors. As she sucked she paused once and she looked at me and said, "You are rather large." Then continued. I soon felt it and this time she did not let it shoot out.................she swallowed.
Over the years we got together on a few occasions and it was always a great cock sucking.
Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.
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.
I have to say that I have been a long time cross dresser since age ten or so. My wife of ten years does not know. I also enjoy looking at sissies with erections. I become very aroused with both of these obsessions I have.
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.
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 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 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
Confessions by confessionstories.org
