Transsexuals & Crossdressers Stories

15,868 results
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Infinite Scroll

Weekend with Elaine Ch. 05

by clarepanties on Sep 26, 2017
Transsexuals & Crossdressers

The following morning, Sunday, I woke to Elaine's normal want, i.e. to perform oral on her before anything else. She removed Jenny's panties and presented her now shaved cunt to me. It was, of course a pleasure to service the woman who was becoming my Mistress. This servitude was immediately followed by Jenny moving into position. Elaine reminded Jenny, "We...

Weekend with Elaine Ch. 01

by clarepanties on Sep 26, 2017
Transsexuals & Crossdressers

Well, a very nice surprise has come along. A very old girlfriend has invited me over to her place in Norfolk for "an interesting very long weekend" in 10 days time. Instructions are to follow. The last time that we spent together was more than interesting and definitely explored some new experiences for me, and also for her. And it is some of this that I wil...

Ladyboy Maid

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'Hi,' she said, her voice sultry. 'I'm the new maid. Lisa.' The new maid had turned up at the house of Mark and Susan Reynolds. Mark had answered the door, and he was impressed. Lisa was around thirty, with large brown eyes and wide red ruby lips. Her exotic features made Mark think that she was from somewhere near Persia. She was about 5'6" in black high-...

The Ballad of Jaimie and Vera Ch. 03

by AwkwardMD on Sep 14, 2017
Transsexuals & Crossdressers

After the 'Establishing Shot', Vera and I hit the road. We rented an RV and set out cross country. Vera called it "Jaimie Bradley's Sexual Awakening Tour 2013: Coming to a city near you!" The plan was to go around and find people I could have sex with, have them sign a release, film it, and put out a DVD. Or start a website. That part of the plan was fuzzy,...

Mia Mine Ch. 09

by cliptoe on Sep 26, 2017
Transsexuals & Crossdressers

I want to send out my thanks to all of those who have read my stories. I especially appreciate the kind and encouraging comments, and yes, even the votes. This chapter is a continuation of a growing relationship, so for a better understanding of some of the background I suggest starting from the first chapter and working through, as always this is the reader...

Modified Ch. 01

by KegRoller on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: For those inclined with this particular fetish I hope you enjoy the story. As a reminder, this is a work of fiction. Any similarities of characters or places in the story to actual people or places are completely coincidental. Also, I in no way endorse the actions that take place in this story. This story is fantasy dealing with non consensual...

Modified Ch. 05

by KegRoller on Sep 12, 2017
Transsexuals & Crossdressers

Penny is sitting in her biology class, tired and sore, trying to make sense of what just happened to her. She went to the campus nurse's office hoping to take control of her situation, but instead was dominated by an insane doctor. The doctor tied her to the examination table and then proceeded to ram a huge dildo into her pussy, all the while telling her ho...

Dressed So Ch. 03

by MadQuill on Sep 25, 2017
Transsexuals & Crossdressers

The Master Tess needed a shower and I had to prepare some quick notes. Then I showered and dressed. I grab my bag and one of her coats and asked Tess to get moving. She quickly called the Lobby and asked the doorman for a cab to downtown. We chatted quietly as the elevator descended and I lightly kissed her. "I need to stop at my place. I can't enter the...

Ivana Pushing Sissy's Limits

by frezrevup on Sep 16, 2017
Transsexuals & Crossdressers

"You look ravishing," my wife Ivana said as I stood before her in a short red velvet dress with white tights and black Blahnik mary janes heels. She walked over to put a hair band in my long black hair. It was down to my shoulders now, flat-ironed straight. We stood together in front of the mirror after she was done. In her heels, Ivana was four inches tal...

Jacki's Journey into Sissyhood Pt. 05

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

We finished our drinks and talked in excitement about the forth coming party. Steve then caught the glint of headlights as they turned up the driveway. "I better go make sure the valets get started parking the first cars right, or we will never get all of them in here." Steve sat down his beer and headed for the door, "Be back in a minute girls." Seeing the...