Transsexuals & Crossdressers Stories

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Sarah Asked to Work as a Hotel Maid

by SarahCD on Dec 17, 2018
Transgender & Crossdressers

A few weeks before the events described here, I had watched a transgender porn video. It was about a guy who dressed as a French Maid and worked in a hotel. I was so excited by what happened to him, I wanted to give it a try. I searched on-line for an LGBTQ friendly hotel and found a promising one close by. I emailed them and asked if I could tryout as a 'ma...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

Dani and Paulie Ch. 01

by dani247 on Oct 31, 2018
Transgender & Crossdressers

I only ever told my father one lie. That was about the boots. I was about to turn 18, jobless, directionless and pretty screwed up to be honest. There had been rows, fights, shouting matches and long frustrated silences about what I was doing with my life, but I had formulated a plan. Kind of. Two years prior I had finally admitted to myself, and no one else...

Magic Dress - Felicity Pt. 02

by SlightlyRude on Apr 9, 2019
Transgender & Crossdressers

CHAPTER 3 One day, rummaging around in the study she came across my butt plugs. "Are these what I think they are?" I said they were. "And how often do you use them?" I said not since she found out about Felicity. "And how do you feel when you use them? Are there any men in particular you think of?" I said I didn't think of men at all, it just seemed nice to...

Magic Dress - Felicity Pt. 01

by SlightlyRude on Apr 9, 2019
Transgender & Crossdressers

My wife knew about my secret stash of porn. At least she thought she did. Having discovered it, she pretended she did not know and did not look there. That let me hide my real stash under a false bottom in the chest. I encouraged her with her hobby of photography, and now she often went out for the day on a weekend with the club to shoot some landscapes or w...

Sarah was Naughty in the Sauna

by SarahCD on Jan 16, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...

The Present

by HSMan on Jan 16, 2019
Transgender & Crossdressers

"I've bought is a present." She said, "I can't wait for you to see it." She added. Despite my attempts she wouldn't let on so I was intrigued to say the least. I arrived at her place a little later than I'd have liked to, driving with a hard on is distracting to say the least. She met me at the door dressed in a short pleated skirt, white blouse, stockings...

Submission is the Ultimate Pleasure

by StephaniePlayland on Aug 7, 2019
Transgender & Crossdressers

Another installment of Stephanie and Sir. There isn't much time to get ready. Luckily I keep part of myself shaved, so it's a quick shower. Take an enema and douche to clean myself out. A girl needs to be ready to receive. A little lube to help slide the plug into place I need to be nice and relaxed so Sir can fuck me. Next I tuck and tape my little clitty...

Treat Her Like a Lady

by justincbenedict on Aug 7, 2019
Transgender & Crossdressers

"Remember" Diehl said warningly to Quinn, the new sorority pledge. "You have to keep your weight down, and eat like a bird." Quinn looked over the table in pain at beautiful Diehl, full of red hair and vigor. God, she's so beautiful. Quinn had been at one time Azrael "Quacks" Quackenbush, point guard on the Buttermilk State University Buccaneers, basketba...

The Bimbo Dildo

by Sissyhalo1 on Dec 24, 2019
Transgender & Crossdressers

It came to me through a yard sale at this house full of super hot chicks in town living together selling all their ex-boys stuff. It was a smooth ivory dildo a full foot long and super realistic and thick too. It made my pussy twitch just looking at it. All of them, all of them were super hot but too hot that porn guys wet dream with round perfect asses,...