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Teen Cross dressers First Man.

Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about ... up in the air. He just looked and said "who first" and I actually wanted to feel a hard cock pumping my asshole ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 710  |  
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Teen Cross dressers First Man.

... female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about ... up in the air. He just looked and said "who first" and I actually wanted to feel a hard cock pumping my asshole ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2274  |  
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Cross Dressers First Time

... I had never had a sexual encounter with a man and saw myself as curious only.

It ... and enjoyed the films of some hot cross dressers I stroked myself through my panties but ... hardening. It wasn't huge but for the first hard cock I'd seen in real life it ... ... Continue»
Posted by webbyhose 1 year ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1797  |  
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3 Teen Cross Dressers Misadventure - Part 2

... a world of hurt.


What else could we do? I was the first. I took off my jacket and then practically before I even took ... thing we are fucked. Again the man handing the clothes told him to sit down and cross his legs. Finally it was ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 481  |  
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3 Teen Cross Dressers Misadventure - Part 3 Final

... got off of me and I had my first view of the room since Sean’s man switched with one of mine. Brett was ... a couple minutes he flipped me over and said, “bitches cum first.”


I was almost fully hard but the pain prevented it. Out ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 751  |  
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3 Teen Cross Dressers Misadventure - Part 1

... and on our 6th drink or so we headed out, first to grab some snacks at the gas station across the ... ... Continue»
Posted by ClaireCD 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 468  |  
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ANGELICA BEGINS - MY FIRST MAN (ENGLISH)

... inside you…). I’ll never forget what I felt, when my very first man cummed inside me…in that moment an idea crossed my ... ) with the smell of sperm, saliva, sweat of Fabio, my first man, the one who had the privilege to start fucking a handsome ... ... Continue»
Posted by AngelicaTrav 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 1670  |  
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My first man Fuck buddy.

... is dating a wonder woman. When her and I first meet she would suck my cock anytime I wanted ... I think I would be getting naked with another man none the less be wanting to have ... me back to hardness so I could try my first man pussy.But that will be another ... ... Continue»
Posted by mycocknurass 2 years ago  |  Categories: First Time, Gay Male  |  Views: 2952  |  
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A Cross-Dresser's tale

... was “becoming a man.”

It was about this time…timelines get fuzzy because of the booze…that I saw my first she-male ... -up my marriage.

I do believe that a lot of us cross-dressers/she-males/Trannys have the XXY syndrome, as I unprofessionally ... ... Continue»
Posted by prairieFreak13 1 year ago  |  Categories: Shemales  |  Views: 1089  |  
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Cross-dress dreams come true.

... alone. I wasn't feeling it. I'd lost my company-man enthusiasm.
On the first day, I sat at the back of the auditorium ... him about how often I jerked off looking at pictures of cross-dressers. The excitement of imagining my hand going up under a ... ... Continue»
Posted by dlcalguy 2 months ago  |  Categories: Anal, First Time, Gay Male  |  Views: 3479  |  
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Party Surprise - First sex as a Crossdresser.

... was at work. I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a cock in panties.

We ... you. But you have disappointed me. Letting a man cum in your ass on the first date, I’ll have to teach you some ... ... Continue»
Posted by SatincdAus 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 2869  |  
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The Cross Dresser and The Big Fat Fuck

... said she was a woman trapped in a man's body wear as I was just a ... "

(YES! YES! YES!)

For our first date Debbie gave me a tour of ... lesbian couples, straight couples even a few cross dressers here and there.

Debbie and I found a booth ... ... Continue»
Posted by loriannthetran 4 years ago  |  Categories: Fetish, Hardcore, Sex Humor  |  Views: 662  |  
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A Night with Mike (his first with a man)

... watching boy on boy sex and having his first ever blow job from a man, Mike and I needed a bit of a rest to ... It’s much more complex than you think.”

“So trannies and cross dressers are nothing new/”

“Nope, perfectly normal really. Speaking of which ... ... Continue»
Posted by daviea9 1 year ago  |  Categories: Gay Male, Masturbation, Voyeur  |  Views: 2383  |  
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First Time: Slick&tyg:Part 3.

... shop. It catered to big women and cross dressers I think because most of the clothes ... I wasn't ready for it to be my first time for sex. I had been feeling a ... wriggling into my pussy. Never had a man's mouth ever been there... I was struck with sensations ... ... Continue»
Posted by tygress77 3 years ago  |  Categories: BDSM, Fetish, First Time  |  Views: 1555  |  
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How I Became a Cross Dresser

... his cock started pulsing in my mouth, and I felt the first hot squirt of cum hit the back of my throat ... that there are a group of men out there who loved cross dressers, and I knew I was going to spend the rest of my ... ... Continue»
Posted by kbking70 2 years ago  |  Categories: Fetish, First Time, Gay Male  |  Views: 1145  |  
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The old man Part 1

... walked only to be meet by a crowd of cross dressers and gays wow was I happy, I ordered my ... heavy cum filled balls.
I started fucking his man cunt building up a rhythm I was loving ... time just me and the old man I wanted my old man's small cock fucking my ass ... ... Continue»
Posted by TheFirm 4 months ago  |  Categories: Anal, Group Sex, Mature  |  Views: 632

My First Time!

... I lived in at the time a lot of transvestites, transsexuals, cross dressers and their admirers would hang out on forth street ... bent over with my *** in the air anticipating my first *** *******. First Christine took some petroleum jelly from the jar on ... ... Continue»
Posted by cute_girls_with_dick 1 year ago  |  Categories: Anal, First Time, Hardcore  |  Views: 1624  |  
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A man anally molests a stranger on a crowded commu

... cross dressing, homosexual lifestyle," said Peter.

"My cross dressing homosexual lifestyle?" Not even an official couple yet, they were already having their first ... ... Continue»
Posted by fotisampini 10 months ago  |  Categories: Anal, First Time  |  Views: 3806  |  
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The First Step With Hope- part one

... about it being a tad sleazy; neon lights, with scantily clad cross-dressers in need of a shave hanging around the entrance etc.; ... I held out a hand instinctively and our fingers touched for the first time; there was a sharp jolt as static electricity stung ... ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 593  |  
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school teen gay crossdresser first time sex

... cross dresser's first gay experience
I was just a young boy then, senior in high school, horny as hell and dreaming of my first ... gay ass was being fucked for the first time by a wonderfully hard 7 inches of man meat. it was pain........it hurt.......I held ... ... Continue»
Posted by allisontranny 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5762  |  
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