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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 would like to find somebody to ... off, but not only that he deepthroated me the hole time i only lasted 3 minutes till i said i was going to cum but ... ... Continue»
Posted by floyd1985 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1407  |  
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Cross Dressing play turned horribly wrong - fantas

... 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 1 year ago  |  Categories: Anal, Gay Male, Interracial Sex  |  Views: 2749  |  
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my older cross dressing friend

... my knob I leaned my head back and licked his asshole to show my appreciation for his excellent work. My first blowjob, both ways. My first time ... ... Continue»
Posted by TenderLoins 1 year ago  |  Categories: First Time, Shemales  |  Views: 992  |  
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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 ... I started slowly at first enjoying every sensation i was feeling but then it gradually got to fully stoking with my cock out ... ... Continue»
Posted by kaos420 1 year ago  |  Categories: Fetish, First Time, Masturbation  |  Views: 874  |  
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Nancy Friday My Secret Garden Women’s Sexual

... my clitoris and experienced my
first orgasm. Since that time, my ... 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 1 year ago  |  Categories: Fetish  |  Views: 25760  |  
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Alice 1

... I was worried about my first time, I still wanted to give myself to her.
As I assumed the position on my hands and knees, ... have never been with anyone but female before, you are my first cross-dressing girl’.
‘You, darling Chris, are only the second ... ... Continue»
Posted by ratty9uk 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 3805  |  
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Cross Dressing, Pegging and the Promise of a Three

... my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing ... my head. She then ringed my mouth with lipstick, applied mascara to my eyes, and powdered my face.

It wasn’t the first time ... ... Continue»
Posted by daviea9 2 months ago  |  Categories: Fetish, First Time, Mature  |  Views: 627  |  
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Cross Dressing for Ann Again

... my first amazing session with Ann, the neighbour ... my earlier account of dressing up for Ann you will be able to imagine my ... deep, and placed it round my body. Every time her soft hands or arms ... again” and she said “well don’t play with yourself between now and ... ... Continue»
Posted by daviea9 11 months ago  |  Categories: Fetish, Mature, Taboo  |  Views: 2418  |  
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... my son for over 4 years alone during this time I had no time ... cross dressing ... my aching mouth was rewarded with him grunting and shooting his load into my mouth the first volley shot into the back of my ... ... Continue»
Posted by jazmine69 3 years ago  |  Categories: Anal, Gay Male, Taboo  |  Views: 4770  |  
  |  19

Mom's still my first

... my
clit and it sent a shiver down my spine to my toes.

I was thinking about mum taking my nipples in her mouth, when I had my first ... dressing ... ... Continue»
Posted by PornApocalypse 2 years ago  |  Categories: First Time, Lesbian Sex, Mature  |  Views: 8122  |  
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Mom's still my first

... my life. My first, and as yet only sexual partner has
been my ... inserted a tampon, before dressing ... to play with my ... my pussy. This time though, mom moved her fingers further
inside my panties as she slowly approached my pussy. Mom's fingers moved
through my ... ... Continue»
Posted by lasslorn30 1 year ago  |  Categories: First Time, Lesbian Sex, Taboo  |  Views: 18057  |  
  |  19

Stepmom still my first

... my
clit and it sent a shiver down my spine to my toes.

I was thinking about mum taking my nipples in her mouth, when I had my first ... dressing ... ... Continue»
Posted by Marcia2 1 year ago  |  Categories: First Time  |  Views: 3803  |  
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My First Night of Being a Sissy Cumdump

... in my alone time but never acted on my slutty urges from fear of being caught by my ... my place. I included a picture of my ass bent over ready to be fucked. It was only about 20 min later when I got my first ... is for sure I will always be a cross-dressing ... ... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3857  |  
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My Cross-Dressing for a couple fantasy

... of wanting to try cross dressing for a bi-sexual couple. Several years ago i did try cross dressing just the one time for a dominant top ... what was to come and soon i started feeling the first stirrings of my cock beginning to appear in anticipation of the ... ... Continue»
Posted by marcusp1979 3 years ago  |  Categories: Fetish, Gay Male, Mature  |  Views: 503  |  
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Cross Dressing to go to Girls' School

... -educational school and had a great time with the girls I met there, all the way from my first day in “primary one” to the ... or something. But that didn’t have anything to do with cross dressing.

There was an all-girls school a few miles from mine ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 2496  |  
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My first gay experience with an old man (part 9)

... his arm and rubbing my hand across as Harry barreled chest. I told him that I couldn't believe that my very first time was with ... 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  |  Views: 766  |  

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 ... story of my first sexual experience, with a man, ... WWWWWHAT" this was the first time, I had seen a ... I’ve wanted to play with a mans ... ... Continue»
Posted by TgirlViki 3 years ago  |  Categories: First Time, Gay Male, Mature  |  Views: 2589  |  
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My First Meeting - A work of fiction

... She knew this was my first ever meeting with another ... dressing, putting on my suspender belt and lace top stockings over my ... cross my legs, she had a look of joy on her face when she spotted my ... her cock in my mouth. This was the first time I had tasted cock ... ... Continue»
Posted by misssuzywhyte 1 year ago  |  Categories: First Time, Shemales  |  Views: 1611  |  
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My First Time with Brian.

... not share my stories?" Who knows? You might just get a kick out of them. ; ) x

Back when I was 17 I had been cross dressing ... to a cross dresser, he left a good first impression, so good in fact that we wound up dating.

I remember the first time we ... ... Continue»
Posted by NicoleB90 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 1381  |  
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My first time was with a other guy one day after s

... my teens the first time I had sex and it was with a boy that was two years older then me and I WAS NOT HIS first ... 27 I got married and never told my wife about being with guys and into Cross dressing but she knew that pantyhose was a big ... ... Continue»
Posted by Hoselover1 2 years ago  |  Categories: First Time  |  Views: 746  |  
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