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crossdress sex stories


Exploring Jay's Huge Cock

We entered my house through the garage and came into the kitchen. Jay looked over the place and was impressed by my house but maybe just a bit scared and mostly excited. "Would you like a drink Jay," I asked. "No Jack, just fine thanks. Hungry t ..continue reading

Jimmy the panty boy

"Timmy, dear" Cassandra said while reading morning paper at the breakfast table, "I have a convention in New Orleans and I'm leaving right after work for the airport, so I'll have the cabby swing by here and pick up my bags!!!" "I've laid out all the ..continue reading

Caucasian Bitchboy

Guapo Tony was really good looking, about 6 foot 2, lots of muscles and tattoos, shaved head – totally fine! I could tell when he saw me sitting there, a young Caucasian sissy with crossed legs and high heels, that he was not disappointed in what h ..continue reading

Becoming Michelle

I've always had a very high sex drive and various fantasies. My wife, Michelle, is pretty much the opposite. Sex is pretty standard and not very often and whilst this is fine for Michelle it does leave me wanting. I would never cheat so I often turn ..continue reading

Wife indulges her husband's cross-dressing fetish

When my wife Jane asked if I would be a volunteer worker at her company's western night, I said sure, why not? She told me she would fill me in on the details as the time drew nearer. A couple of weeks before the event, Jane started making a sa ..continue reading

Submission by The Crossdressers

Thanks to the internet, I've had access to more porn than one person could ever need in a lifetime. It's good and bad because after awhile you become desensitized. Seeing typical porn already became dull, and I'm only 23! I started searching for new ..continue reading

Paul the gay

In just about an hour he would be here I was so excited, finally I was gonna get this guy alone. Just me and him for a few hours alone without the worry of interruptions. I'm a very submissive white gay bottom, I'm 5'4' weight about 115 lbs. With a s ..continue reading

Crosdresser sucks cock

He never expected that I was sissy and never dreamed he would be one of my lovers This happened when I was beginning to dress up as Mel frequently. Saturdays were the best days for me, except that my friend Pete would always stop by in the middle o ..continue reading

My BBW Mother

My name is Pete, I am 28, live in the UK and have a good job. I am a fairly good looking guy, 6'0, and quite muscular. I live with my mother Denise who is 54. I used to live in London and have a gorgeous girlfriend up until the age of 23. She was bl ..continue reading

My first time encounter with a ladyboy

I had been eyeing her up across the bar for about 20 mins when she finally noticed me. She flashed me a cheeky grin and I could feel the front of my pants start to tighten. I told the bartender to bring her a drink and when he did she looked over and ..continue reading

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Mama's Gigolo

I know a bunch of this stuff, probably 98 percent of it, is false about incest. But in email chats with this guy Long Boy Slim, he convinced me to let him post this story I forwarded to him, word for word. It's true. It's what happened between me ..continue reading

Dod's Mum - Ssbbw sex story

Belinda was a wonderful person, great personality, bubbly; jocular and always full of fun; she’d a list of friends as long as your arm. However, she had one large problem and she herself would be the first to admit it; she was built like a brick sh ..continue reading

Ms. Kelly toy boy gangbang

I turned on the hot water, grabbed the baby oil and starting lathering myself up. I could see my breasts glisten in the sun, dripping oil all over my body. Saturday was boy’s night and I was preparing. I dipped 2 fingers in my pussy and began playi ..continue reading

Megan's Diary - helping out a friend

Just the first of many accounts of my own sexual experiences (long blonde hair, 5'6, brown eyes, curvy figure,32 D breasts, Spanish descent, light skin) “OMG!, you want me to what?”, I shrieked out in utter surprise “I need you to come with ..continue reading

A Brazilian Welcome

Jackie's mother greeted her with a smile and a letter when she returned home from high school that day in late January. It was Jackie's sophomore year, and she had applied for a scholarship to study abroad. All through school, Jackie had studied ..continue reading

My fantasy

Growing up you sometimes remember some weird things. I remember the first time I saw a girl with a shaved pussy. It was my sisters friend Becky. She and my sister were laying out in the backyard of our house trying to get a tan. I was not trying to b ..continue reading