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my first cross dressing play time

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 ... a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks... Continue»
Posted by floyd1985 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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How I started Cross Dressing and other first times

... want to write this to record how I think I got started cross-dressing. It is my intent to also ... !

The next memory is what I have always said was the true cause of my cross-dressing ... , but no cumming. In fact, I remember one time when we were “crossing steams” in the toilet my friend... Continue»
Posted by pantiesdave 9 months ago  |  Categories: Fetish, First Time, Taboo  |  
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Cross Dressing play turned horribly wrong - fantas

... dressing her in all different combinations of outfits each time I fucked her, my cock starts ... passed this first test. “Share that bitch around b*o, time for this little slut to taste my cock now ... still horny and wasnt satisfied. I have tried a little bit of cross dressing before but I was feeling... Continue»
Posted by clevelandzj 3 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
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my first time dressing

... for the first time with another mans cock.He directed it into my mouth and I remember starting ... would do chores for a neighborhood guy,he was much older than my own dad.Was probly after a month ... was comfortable with him and played along.It was normal at that age to play that way.Then all of a sudden he... Continue»
Posted by cdlover19 6 months ago  |  Categories: Fetish, First Time  |  
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My first time dressed as a girl part 2

... My First Time Dressed as a Girl, pt 2
(The events of this story are true and reflect what happened ... by Bobbi dressed like this. It’s kind of my first time.” I was a little nervous, given the way he eyed ... thirty years ago the first time I went all out and dressed as a female. The conversations in it may... Continue»
Posted by sbobbi66 2 years ago  |  Categories: Lesbian Sex, Sex Humor  |  
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My first time dressed as a girl (A True Story) The

... My first time dressed as a girl (This is a true story, the conversations in it are only as accurate ... teenage girl. Once I even dressed in her bra and panties while I sucked off my best friend and neighbor ... threatened to go out to the bar without me if I didn’t play along.
Soon Michelle had me dressed up... Continue»
Posted by sbobbi66 2 years ago  |  Categories: Lesbian Sex, Sex Humor  |  
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First time dressing

... % of Transvestites.
My fetish started when I was an adult in my 50s. I dressed for the first time when I met ... smile on his face. I responded, "Yes that was kind of hot. That was my first time to give a lap dancing ... was just a normal cross-dresser. Now the online article was about the psychology of cross-dressing... Continue»
Posted by cindyusa58 1 year ago  |  Categories: Anal, First Time  |  
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First time dressed as a woman

... dick. I've been dressing up on and off since I was a p*****n, starting with my mother's lingerie ... and dresses. I love makeup, but especially lipstick. I used to masturbate by stroking my cock ... on by CD's, TS's and TV's and frequenting the cross-dressing forums and chat rooms. I began building up... Continue»
Posted by kevinj631 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Cross Dressers First Time

... would be dressing more often and the other time I visited an e****t and wore panties and stockings ... .

What I kept quiet and has since I was young was that I cross dressed. I now had a locked closet full ... of ladies, clothes, lingerie, shoes and wigs and make up. I would indulge myself and dress as my... Continue»
Posted by webbyhose 2 years ago  |  Categories: Anal, First Time, Gay Male  |  
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my first time cross dresser

... girls cloths he love it too he told me he love young boys cross dressing so I got dressed up in my ... time taested my bum now I love tasteing my bum because of hin is start to uncuff me then he push me ... . As he was wanking his cock as I finger my virgin bum when he cumed I Was dyeing to lick it up so he... Continue»
Posted by welsh_sissy 2 years ago  |  Categories: Masturbation, Sex Humor, Taboo  |  
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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 ... fitting thigh length lycra stretch dress which clings tightly to my figure. Admiring myself ... at the prospect of what was to come and soon i started feeling the first stirrings of my cock beginning... Continue»
Posted by marcusp1979 4 years ago  |  Categories: Fetish, Gay Male, Mature  |  
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My First Time Dressed as a Girl (PT 2) (Aftermath)

... My First Time Dressed as a Girl,(PT 2) Aftermath
Hi Reposting an account of how I got started ... dressed like this. It’s kind of my first time.” I was a little nervous, given the way he eyed me like ... , a little shocked at the words coming out of my mouth. Last night was the first time I had ever dressed up... Continue»
Posted by sbobbi66 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  
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My Cross Dressing for a couple fantasy (part 2)

... my hemline and slowly his fingertips lifted the bottom of my dress until he could feel my stocking ... over my body, finally coming to rest on my "breast". All the time i was pressed against his chest i ... hands to the bottom of my dress, richard then proceeded to lift it off over my head and finally i... Continue»
Posted by marcusp1979 4 years ago  |  Categories: Fetish, Gay Male, Mature  |  
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Cross dressing with my sister

... , standing naked in front of pru for the first time, my cock rose to the occasion. Pru just stood and looked ... was dressed to kill. Pru took off her robe revealing for the first time to me a pair of lovely purt ... tits and a shaven pussy, she got herself dressed as my cock tried to f***e it's self out of my... Continue»
Posted by drew2000 2 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
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First time dressing up

... clothes, but the time after this was when i really discovered how fun it was to cross dress.

After ... the first time i crossdressed in my s****rs clothes, i just had to do it again. It was a week until ... in the mirror. When it started to get near the time my parents got home i went back to my s****rs... Continue»
Posted by Badassgirl123 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
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First time showing and playing in public

... relationship. John wrote about the first time him, his best friend / my ex-boyfriend and I all played ... to spread my legs. Each time he did this he would bump Russ’s arm to get him to look back. The first ... the whole time. John would reach over and touch or play with my clit or a few times would run the end... Continue»
Posted by plez2tease 6 months ago  |  Categories: First Time, Group Sex, Voyeur  |  
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My First Time Dressed as a Girl (PT 3) (Consequenc

... Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided ... licking it slowly at first teasing him before I engulfed the head between my pretty painted lips. I ... was surpassing my previous attempts. Of course during this time the busboys and water boys who had been... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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My first time dressing

... done that in front of another guy.But id never been dressed like this either and my cock stayed so ... was licking my ass inside and out.It didn't take long before I was cumming for the 2nd time at his house ... me stop sucking him,by this time he had both hands on my head and was making me choke on him.Wasn't... Continue»
Posted by cdlover19 6 months ago  |  Categories: Fetish, First Time  |  
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My first time being taken dressed as a woman

... never dressed up completely.

I spent at least twenty minutes checking myself out, at this stage my ... I'd get the opportunity to dress up again. I cleared away the sofa in my living room and set up ... , close ups, and also some harder pics with my favorite black 10" dildo up my butt. All this dressing... Continue»
Posted by jimbo70xyz 3 years ago  |  Categories: BDSM, First Time, Shemales  |  
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My first time

... was no longer on office duty, and so was dressed quite differently from the first time that I had met her. She ... , and she begged me to finger her pussy. I felt a wicked thrill, as for the first time in my life I lifted ... rose to cup both of my titties, and as her mouth descended upon them I discovered for the first time... Continue»
Posted by dian0223 5 years ago  |  Categories: First Time, Lesbian Sex  |  
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