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Teen Cross dressers First Man.

Teen Cross dressers First Man.

... I started to do a little bit of discreet cross dressing in my house about a year ago and ... I wasn't sure what to think but the first thing that came to mind was to just ... the air. He just looked and said "who first" and I actually wanted to feel a hard cock ... ... Continue»
Posted by ClaireCD 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Teen Cross dressers First Man.

... I started to do a little bit of discreet cross dressing in my house about a year ago and ... I wasn't sure what to think but the first thing that came to mind was to just ... the air. He just looked and said "who first" and I actually wanted to feel a hard cock ... ... Continue»
Posted by ClaireCD 4 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Cross Dressers First Time

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

It was ... 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  |  
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3 Teen Cross Dressers Misadventure - Part 2

...


What else could we do? I was the first. I took off my jacket and then practically before ... favorite and apparently also Craigs. "I get first on the schoolgirl." he said. We were ... Again the man handing the clothes told him to sit down and cross his legs. ... ... Continue»
Posted by ClaireCD 4 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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3 Teen Cross Dressers Misadventure - Part 3 Final

... it inside me and gave small thrusts at first. I started getting hard and my cock ... me and I had my first view of the room since Sean’s man switched with one of mine ... he flipped me over and said, “bitches cum first.”


I was almost fully hard but the pain ... ... Continue»
Posted by ClaireCD 4 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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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 4 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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ANGELICA BEGINS - MY FIRST MAN (ENGLISH)

... understood very well that he was my first man and this was exciting him;then suddenly ... forget what I felt, when my very first man cummed inside me…in that moment an idea ... of sperm, saliva, sweat of Fabio, my first man, the one who had the privilege to start ... ... Continue»
Posted by AngelicaTrav 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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My first man Fuck buddy.

... dating a wonder woman. When her and I first meet she would suck my cock anytime I wanted. Well ... think I would be getting naked with another man none the less be wanting to have him ... to hardness so I could try my first man pussy.But that will be another story. ... Continue»
Posted by mycocknurass 3 years ago  |  Categories: First Time, Gay Male  |  
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A Cross-Dresser's tale

... for a couple of years after that first purge. Football, wrestling, girls, school ... se…I never did imagine havng sex AS a man with a man.
I still don’t.

But I also knew ... do believe that a lot of us cross-dressers/she-males/Trannys have the XXY syndrome, ... ... Continue»
Posted by prairieFreak13 2 years ago  |  Categories: Shemales  |  
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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 for ... him about how often I jerked off looking at pictures of cross-dressers. The excitement of imagining my hand going up under a skirt ... ... Continue»
Posted by dlcalguy 8 months ago  |  Categories: Anal, First Time, Gay Male  |  
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Party Surprise - First sex as a Crossdresser.

... . I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a ... and thought I was about to taste my first cum but he stopped and pulled his cock ... have disappointed me. Letting a man cum in your ass on the first date, I’ll have to ... ... Continue»
Posted by SatincdAus 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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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 ... ;

(YES! YES! YES!)

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

Debbie and I found a ... ... Continue»
Posted by loriannthetran 5 years ago  |  Categories: Fetish, Hardcore, Sex Humor  |  
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Crossdressers First Time

... had never had a sexual encounter with a man and saw myself as curious only.
It was ... 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 maninnylons 3 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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  |  
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My first Craigslist story...

... a little bi-curious, never minded watching a bit of man on man porn, she males and cross dressers that sort of stuff. When I was younger ... site. I began replying to ads, just testing the waters at first to see what kind of replies I got, mostly they were ... ... Continue»
Posted by cobainafar 6 months ago  |  Categories: First Time, Gay Male  |  
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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 ... his tongue wriggling into my pussy. Never had a man's mouth ever been there... I was struck with ... ... Continue»
Posted by tygress77 4 years ago  |  Categories: BDSM, Fetish, First Time  |  
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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  |  
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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 on ... 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 2 years ago  |  Categories: Anal, First Time, Hardcore  |  
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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 ... him up and got him into position his man cunt looked so sweet and open I could ... heavy cum filled balls.
I started fucking his man cunt building up a rhythm I was loving ... ... Continue»
Posted by TheFirm 10 months ago  |  Categories: Anal, Group Sex, Mature  |  
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A man anally molests a stranger on a crowded commu

... his eyes went to the most beautiful women first, typically a blonde with big tits and ... having anal sex for the first time. The first time she bumped him, she ... was a real woman instead of a cross dressing, transgendered man. Controlling the urge, in the way ... ... Continue»
Posted by fotisampini 1 year ago  |  Categories: Anal, First Time  |  
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