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my first cross dressing play time

my first cross dressing play time

... sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and ... while he would reach down further and stroke my cock for a few seconds. then i ... not only that he deepthroated me the hole time i only lasted 3 minutes till i said ... ... Continue»
Posted by floyd1985 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Cross Dressing play turned horribly wrong - fantas

... at work and play by myself a little, iwas still horny and wasnt satisfied. I have tried a little bit of cross dressing before but I ... that I passed this first test. “Share that bitch around b*o, time for this little slut to taste my cock now boy” interuppted ... ... Continue»
Posted by clevelandzj 2 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
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Bi MMF, FemDom, Cross Dressing, Cuckold

... too good to be true, but there I was, fucking my friends cross dressing ass. If you saw him from behind, you would swear ... ! It was amazing when you came in my ass, thats the first time anybody has ever done that" he said. "She gives you ... ... Continue»
Posted by chrissylegs 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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my older cross dressing friend

... and licked his asshole to show my appreciation for his excellent work. My first blowjob, both ways. My first time licking his asshole. I wanted more. I didn ... ... Continue»
Posted by TenderLoins 2 years ago  |  Categories: First Time, Shemales  |  
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My first time

... is a lil story for everyone during one of my early cross dressing experiences. Both my parents worked during the day and I didn’t feel ... while watching myself in the mirror I started slowly at first enjoying every sensation i was feeling but then it gradually ... ... Continue»
Posted by kaos420 1 year ago  |  Categories: Fetish, First Time, Masturbation  |  
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Nancy Friday My Secret Garden Women’s Sexual

... my clitoris and experienced my
first orgasm. Since that time, my ... ; intercourse with my b*****rs; sex
play with my father, s****rs ... time to finish dressing, she
caught me in my dressing ... my first friend. I have
told Bill that if our paths should ever cross ... ... Continue»
Posted by DrunkenDiablo 2 years ago  |  Categories: Fetish  |  
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How I started Cross Dressing and other first times

... to cross-dressing happened when I was very young. In fact it may be my first memory altogether ... EBay now. It may have been the first time I did the wash or I may ... in panties
Started to experiment with ass play after a massage attendant slipped a finger ... ... Continue»
Posted by pantiesdave 1 month ago  |  Categories: Fetish, First Time, Taboo  |  
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Alice 1

... me to experience being fucked, although I was worried about my first time, I still wanted to give myself to her.
As I ... have never been with anyone but female before, you are my first cross-dressing girl’.
‘You, darling Chris, are only the second person ... ... Continue»
Posted by ratty9uk 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Cross Dressing, Pegging and the Promise of a Three

... her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of ... Mind you, keen as I was to play with Ann again I did also enjoy ... laughed “God no, that’s the first time anyone has fucked my arse”. “But have you ever ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, First Time, Mature  |  
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My First Translesbian Encounter

... my upperthighs and lower back. Then something fealt very odd to me at the time ... he wants to get more into cross dressing. Sounding kind of manic about ... , licking, feeling. I want rough play, I just want it to be ... first cross dresser I met. you were amazing
... Continue»
Posted by Tslizz 21 days ago  |  Categories: Anal, First Time, Shemales  |  
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Cross Dressing for Ann Again

... a bit.”

If you have read my earlier account of dressing up for Ann you will be able ... me. It was the first time she had actually touched me and my body reacted as if an ... up again” and she said “well don’t play with yourself between now and then and we ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, Mature, Taboo  |  
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Mom's still my first

... that I should, inserted a tampon, before dressing, packing all of the
magazines and dildos ... reached out and for the first time, my mother touched my
breast. She ran her ... I started masturbating. I started to play with my clit and
really get into the video ... ... Continue»
Posted by PornApocalypse 3 years ago  |  Categories: First Time, Lesbian Sex, Mature  |  
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Mom's still my first

... that I should, inserted a tampon, before dressing, packing all of the
magazines and dildos ... reached out and for the first time, my mother touched my
breast. She ran her ... I started masturbating. I started to play with my clit and
really get into the video ... ... Continue»
Posted by lasslorn30 2 years ago  |  Categories: First Time, Lesbian Sex, Taboo  |  
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Stepmom still my first

... that I should, inserted a tampon, before dressing, packing all of the
magazines and dildos ... reached out and for the first time, my mother touched my
breast. She ran her ... I started masturbating. I started to play with my clit and
really get into the video ... ... Continue»
Posted by Marcia2 2 years ago  |  Categories: First Time  |  
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MY FIRST GAY ENCOUNTER

... very lonely as this was a time before PC's or Laptops. The ... I had no idea at all about cross dressing or what it even really was. ... sucking your cocks lover can I play to?".

He was very cute ... into my mouth the first volley shot into the back of my throat ... ... Continue»
Posted by jazmine69 4 years ago  |  Categories: Anal, Gay Male, Taboo  |  
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My Cross-Dressing for a couple fantasy

... a bi-sexual couple. Several years ago i did try cross dressing just the one time for a dominant top guy but since then have never ... what was to come and soon i started feeling the first stirrings of my cock beginning to appear in anticipation of the impending ... ... Continue»
Posted by marcusp1979 4 years ago  |  Categories: Fetish, Gay Male, Mature  |  
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My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always ... on the TV.

I waste no time and get down on my knees in front of him. First I licked and sucked on his ... panties. One thing is for sure I will always be a cross-dressing cum slut. ... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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Cross Dressing to go to Girls' School

... had a great time with the girls I met there, all the way from my first day in “primary ... that didn’t have anything to do with cross dressing.

There was an all-girls school a ... all present. They didn’t know that I cross dressed as often as I could and so ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  
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My first gay experience with an old man (part 9)

... Harry barreled chest. I told him that I couldn't believe that my very first time was with someone like him and that we would be ... and dirty but I always liked it.
My body changed through the years so I stopped the cross-dressing. Vern had to move out-of ... ... Continue»
Posted by Davie40 1 year ago  |  Categories: Anal, First Time, Mature  |  
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My First time

... Cross-dress by borrowing my older s****rs undies and stockings again, my ... my femme side would never go away, I loved dressing ... is the story of my first sexual experience, with a ... WWWWWHAT" this was the first time, I had seen a ... I’ve wanted to play with a mans ... ... Continue»
Posted by TgirlViki 4 years ago  |  Categories: First Time, Gay Male, Mature  |  
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