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Read the best #dressing confession stories
I like to crossdress very much and wish to have sex with males and have fun like a woman.
Recently made an onlyfans so I can descretly post my crossdressing photos. I love wearing cute panties.
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'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 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.
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.
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
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 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.
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.
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 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.
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.
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.
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 25 year old male and I fantasize about being dressed up like a little girl. I would give anything for someone to feminize me.
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.
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.
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
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