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Cross dressed slavery

Cross dressed slavery

... was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt ... uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would ... , coming out in a striped wool tube dress that started at the chin and descended all the way to her... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Cross dressing adventures

... on a little show. All kinds of poses, on all fours, legs crossed, things like that. When I put my ... believe what I found in the box: a complete woman’s outfit with black dress, patent leather heels ... not covered by the panties.
Now the dress, pulling it down over my head I put my arms through... Continue»
Posted by jordan_zander 2 years ago  |  Categories: Anal, Gay Male  |  
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Dogging - Cross Dressing and Porno

... on our way. On the way I explained that the pub was a cross dressing haven which peaked their interest ... cross dresser who knew the neighbour and gave him a big kiss before allowing him in and asking me ... for £10. In the bar 85% of the people were dressed. Some good some different but all enjoying the freedom... Continue»
Posted by daveaverage 5 months ago  |  Categories: Anal, Group Sex, Hardcore  |  
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Cross-dressing - the beginning

... of looking at lingerie, I eventually got into fashion pages. An array of dresses and skirts, blouses ... that I began to wonder what they would look like on me. With this realisation, the urge to dress-up ... , a 36B white bra, and from her wardrobe, her long red dress, all of which I placed carefully... Continue»
Posted by Derk67 5 years ago  |  Categories: First Time, Masturbation  |  
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f***ed to cross dress on Halloween

... Halloween is a great reason to show your submissive side and cross dress for your mistress. Other ... that I would be lenient this time and that I wouldn’t f***e him to cross dress on Halloween.

I ... Halloweens would never be the same after this.

Would you like to be f***ed to cross dress... Continue»
Posted by lokokolo 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Cross Dressing, Pegging and the Promise of a Three

... discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me ... bed, dressed in my mother’s lingerie, and having a good satisfying wank.

I was particularly keen ... face.

It wasn’t the first time I’d dressed up as a school-girl and neither was it the first time I’d... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, First Time, Mature  |  
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Cross-dress dreams come true.

... never told anyone.
I admitted that I'd had fantasies of being with a man dressed as a woman. Even ... to admit I was.
I told him about how often I jerked off looking at pictures of cross-dressers ... rubbing it through sexy underwear.
Sometimes I imagined a man in a dress bending over for me... me... Continue»
Posted by dlcalguy 1 year ago  |  Categories: Anal, First Time, Gay Male  |  
3503
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My Cross-Dressing for a couple fantasy

... cross dressing for a bi-sexual couple. Several years ago i did try cross dressing just the one time ... across a particular clip of a guy dressed in stockings and suspenders and padded bra, being made to suck ... myself looking at their photo and tried imagining how i could dress to pleasure them both, i could... Continue»
Posted by marcusp1979 4 years ago  |  Categories: Fetish, Gay Male, Mature  |  
540
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Cross Dressing to go to Girls' School

... . They didn’t know that I cross dressed as often as I could and so instead of being embarrassed I was actually ... after winning some athletics cup or something. But that didn’t have anything to do with cross ... dressing.

There was an all-girls school a few miles from mine and quite a few of us boys had... Continue»
Posted by daviea9 2 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
2574
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my first cross dressing play time

... i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress ... and would like to find somebody to dress up with and take turns being sluts to each other and then i posted ... but i finaly found somebody that like to dress up and he came over during the day and we started... Continue»
Posted by floyd1985 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Cross Dressing play turned horribly wrong - fantas

... still horny and wasnt satisfied. I have tried a little bit of cross dressing before but I was feeling ... dressing her in all different combinations of outfits each time I fucked her, my cock starts ... very horny and for some reason decided today was going to be the day I dressed myself like a real... Continue»
Posted by clevelandzj 3 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
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Bi MMF, FemDom, Cross Dressing, Cuckold

... my friends cross dressing ass. If you saw him from behind, you would swear I was fucking a sexy ... dress him up like my slut bitch since that's all he's good for" she said with delight. I assumed ... something sexual happens only when she dresses him up. I suspected strap on activity for some time now... Continue»
Posted by chrissylegs 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Cross dressing with my sister

... to get dressed up for the night. Pru said that she was going to wear knee high leather boots ... that will make me stand out".pru stood there in her robe and said " let's dress you as a girl, that'll make ... you stand out!
I jumped at the chance to get dressed as a woman,.
She looked into her draw... Continue»
Posted by drew2000 1 year ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
1178
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Cross Dressing for Ann Again

... shave too as I want to make you up a bit.”

If you have read my earlier account of dressing up for Ann ... moved to the dressing table and ordered me to sit on the stool where she proceeded to apply a light make... Continue»
Posted by daviea9 2 years ago  |  Categories: Fetish, Mature, Taboo  |  
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Confessions of a cross dressing slut

... as a cross dresser. My first kiss, first time my ass had been tongued, first time of sucking cock ... staring at each other. My heart was racing! Did he not know i was a cross dresser?? I'm not 100... Continue»
Posted by mileslong34 4 months ago  |  Categories: Gay Male, Shemales  |  
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cross dressed cocks

... line looking for someone to play with. he to liked to dress but like me was not at all passable ... then me and of average build . it was the bulge in his panties i was interested in. I was dressed ... me like a good whore i would walk him to the car dressed as i was. i was terrified yet it was a rush at the same time ... Continue»
Posted by amitokinki 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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How I started Cross Dressing and other first times

... I love to cross-dress! I love everything about it!
Like most of us cross dressers, I love ... want to write this to record how I think I got started cross-dressing. It is my intent to also ... thing I can remember with regards to cross-dressing happened when I was very young. In fact it may... Continue»
Posted by pantiesdave 6 months ago  |  Categories: Fetish, First Time, Taboo  |  
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caught cross dressed part 3

... eyes, all I could see were replays of myself, dressed like a whore, being strapped to a padded ... breasts. He finally stopped himself and went back to dressing me, finishing with the high heels ... dressed in my full outfit, from my glittery makeup and pigtails, to the white shirt straining... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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caught cross dressed part 2

... adhesive.

"She's ready now ladies. Shall we get her dressed again?" Alice prompted the others ... into my feminine attire. My gag wasn't removed, and once I was dressed, the collar was placed around my ... by little, moving the shaft in and out of me!

I felt the skirt of my mini-dress being pushed up, over... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Caught cross dressed part 1

... on the bed.

I sorted out what it was that I wanted to wear, and without pause, I began to dress. I ... -dress, which only came down about three inches below my panties... and that showed off the lacy tops ... any stubble that might grow during my 'dressed' phase. I lined my eyes with Kohl pencil, and used... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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