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My Early Crossdressing

My Early Crossdressing

... of the road.

One day I was home alone, my parents were away for the week and my s****r ... smooth already so I faked tanned my body, added fake nails, painted them pink, did my makeup, put in my ... in the mirror as I strutted about the house with a glass of wine in. As it got later I decided to go for my... Continue»
Posted by VirginAsAGirl 3 years ago  |  Categories: Gay Male, Shemales  |  
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My Crossdressing Teen Neighbor

... an earlier relationship she had with a black dude.
The main object of my affection, though, is a non ... -passable FT crossdresser that lives there. She has long brown hair and has lovely brown eyes ... to talk to her when my jealous wife isn't around.
A couple of days ago I saw her walking to her car... Continue»
Posted by cumquarts 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Losing my crossdressing virginity

... This is the true story of my first time with a man while fully crossdressed.
I answered an ad ... in the local paper for a guy looking to meet a crossdresser and exchanged some text messages before ... went to the door and rang the bell.
The door was answered by a man in his early fifties of middle... Continue»
Posted by lucytv75 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Beginnings: My First time as a crossdresser (PT 1)

... as accurate as my memory can supply, as this happened Thirty years ago)
When I was 17 I was dating ... which was a bar near campus, favored by college students and locals alike. I reminded her that my fake ... ID had been confis**ted a couple weeks earlier.
“That’s okay. My roommate left her purse here... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My early birthday gift

... My early birthday present,
My life had been like a fairy tale of the adult sort lately anyone who ... recently happened I just want to make clear that my wife Lisa truly is all any man could or would ... we were in Florida she offered to help pick up another woman for a threesome, which blew my mind... Continue»
Posted by keithgreen 1 year ago  |  Categories: Taboo  |  
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my life. the early years

... My Life
Chapter one
The early years
I was born in the early sixties on a farm about two miles ... early because I was not feeling very well, I came into the kitchen and as usual had a drink and took my ... from anywhere, I never knew my mother because two days after giving birth to my younger b*****r... Continue»
Posted by ken256 4 years ago  |  Categories: First Time, Taboo, Hardcore  |  
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... sexualized person. I had a multitude of crushes in my early years, mostly older women ... As long as I can recall, even before my knowledge of sexuality even existed, I have been a deeply ... between my legs. When I discovered masturbation it suddenly opened a whole new world of imagination... Continue»
Posted by missyumyum14 1 year ago  |  Categories: Lesbian Sex  |  
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my early years

... it comes to sex after the first time.
my early years in sex go something like this: my first time ... .

that was my early sex life in a nutshell. i had many more encounters in my later teen years ... ok, so let me tell you about my penis.

bit of an attention grabber, eh? i thought that maybe i... Continue»
Posted by mj2397 3 years ago  |  Categories: First Time, Interracial Sex, Hardcore  |  
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caught my son crossdressing


I had come home early from work and found my son, Jamie, sitting at my vanity, putting on make ... -up. He was wearing one of my cocktail dresses -- and my stockings, my high heeled sandals ... and, it appeared, my lingerie. He hadn't heard me come in, so I just stood silently in the doorway watching... Continue»
Posted by momandboys 2 years ago  |  Categories: Shemales  |  
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Made My Friend A Crossdresser

... worked in same company and he was a friend of a friend. At that time I was crazy about my physique ... and was well built up and he got motivated and asked about my workout routine and slowly he started ... joining me in gym.

Few months later he moved to my apartment and we became good friends. We became... Continue»
Posted by ajbasu 2 months ago  |  Categories: Anal, First Time, Gay Male  |  
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crossdresser ashley[this my story]

... as a girl.over the years I've had a lot of fun crossdressing,and lots of hot sex.and judging from my ... hi my name is ashley,I'm 48,and have been crossdrssing since I was 14.its about the time I discover ... masturbation.when ever I would take a bath or a shower I would take out of the hamper my s****r... Continue»
Posted by blonde68 3 years ago  |  Categories: Shemales  |  
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My Date with a Crossdresser

... A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me ... been feeling sexy, because she asked if I would like to fuck her as she was. I like my dates ... and get dressed, and I would occasionally run my hand over her shoulder or leg, or rub one of her... Continue»
Posted by johnny_antares 1 year ago  |  Categories: Shemales  |  
  |  2

My first time with another crossdresser.

... masturbating. and in the last story was my first time being with a woman wile crossdressed. now ... this story is about my first time with another crossdresser at the age of 18.

it was a friday night ... fell in love with pantyhose. One night after my parents came back from a wedding, i was home... Continue»
Posted by sissypantyhoseboy90 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My first Crossdresser - Part One

... to crossdressers, one of my fantasies. I've never played it out." She was sipping her drink, and without ... video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's ... strutting toward a table.

Convincing she was not, a crossdresser without question. But pretty... Continue»
Posted by abend 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
  |  6

Early morning fuck with Sarah, oh my.

... early sucking led to me shooting my load into her mouth. As Sarah licked clean my cock, she leaned ... I was sl**ping, woken up with my cell going off. Not the alarm but a phone call. I thought it be my ... needed a lift, she was in the bad section of town without a ride. Got dressed and on my way I was. When I... Continue»
Posted by beast255 1 year ago  |  Categories: Masturbation, Taboo  |  

My wife and I, our early life....

... I have another story on here, but this starts much early. While not 'high school sweethearts' my ... people in love, bonding over our situation. Her parents, my parents thought we were both crazy ... married, my wife found out she was pregnant. We thought we had been careful, but my wife had missed... Continue»
Posted by phillybilly 3 years ago  |  Categories: Anal, First Time, Taboo  |  
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My first crossdressed cocksucking (true story)

... It happend few years ago. My ex gave me a "hall pass" to explore my sexuality although she didn't ... on the IRC. He liked crossdressers, boys on the way to become fem sluts. He was mature, around 50. And he ... will be passing my town and stopping by in the hotel. I was supposed to meet him on friday night at the hotel... Continue»
Posted by kamislut 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Made my hubby crossdress and get fucked by bbc!

... into. this time i finally got to see a live crossdresser fucked, my cuckold husband!

so we arranged to meet ... "here ya go my little slut, its your turn"

my husband has never crossdressed before, but he has been ... and to get fucked while its my turn to watch him!

ive always loved being a cuckold wife, meeting new... Continue»
Posted by discreet4rmlanc 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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My story (Part 1) "My Early Encounter"

... My Early Encounter: sherryladyboy

I was 8 years old when I discovered my deep interest in women ... . Their body shape, the breasts and feet caught most of my attention. I started trying put on my mom lingerie ... makeup.
Later I got introduced to pornography, that really caught my interest. I really envied... Continue»
Posted by sherryladyboy 2 months ago  |  Categories: Anal, BDSM, First Time  |  
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My early 1990s adult video supplier’s wife T

... in the early 1990s I moved to London and lived in bedsit near Stratford, East London. I did find ... the city a bit daunting at first but enjoyed going down to soho. I saw some ‘live’ shows and bought my ... could go through them and if any caught my eye I could watch a sample. After watching the first sample... Continue»
Posted by nigeltallguy 1 year ago  |  Categories: Masturbation, Mature  |  
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