Sissy Transformation Stories

14,811 results
Orientation
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Infinite Scroll

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

Scorned Bitch

by lyzunchik on Sep 16, 2017
Transsexuals & Crossdressers

"I'm assuming this is not entirely business," I asked Rod when I meet him for drinks after work. He's a fellow businessperson and we collaborate on some projects. I provide technical and consulting services that augment his contracts with various businesses and government agencies. "No, not really, but I thought it an appropriate segue to get you here fo...

Last Friday: First Sissy Experience

by sissysyzygy on Mar 5, 2018
Transsexuals & Crossdressers

Been a lurker for a little while, and thought it was time I contributed with a post! *** Title: Last Friday "You ready for your surprise?" she asked me coyly. "Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest...

Playing The Naughty Schoolgirl

by davidhtm on Aug 18, 2017
Fetish

Full permission is granted to reproduce this work, provided credit is given to the author. The following is an adult story. If you are not 18, you cannot read it. If you are offended by sexually oriented material, stop now. This is my second attempt at writing a story any comments would be appreciated. * * * * * I had been serving Bill and Jane for sever...

The Sexy Cuckold Couple Pt. 15

by cuckcpl4play on Sep 26, 2017
Fetish

PART 15 POOL 2 As we walked outside, I noticed that our private area was more populated than expected. There were a few more additional males but more than a handful of additional and very attractive females. Sir Jeremy approached my wife quickly and I watched as the other women gawked at her and then began laughing at her as several of them even engaged in...

Once Upon a Laundry Ch. 02

by thekestrelkid on Aug 7, 2018
Transsexuals & Crossdressers

At 7 sharp I knocked on Jessy's door nervous and anxious still not entirely sure what I was doing. I couldn't believe how hot a time I had down in the laundry room with her making me finger my own ass like a "pussy" and jerk off for her. The thought of taking it to the next level was exciting. Jessy answered the door dressed only in an over sized t-shirt a...

Feminized by My Girlfriend Ch. 02

by Trinni69 on Sep 25, 2017
Transsexuals & Crossdressers

I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as closely as I could and hoped no one would notice me. Luckily it...

Happy Endings Ch. 02

by desireethtttv on Sep 13, 2017
Transsexuals & Crossdressers

"So Desiree how did you like your first night at Happy Endings Massage Parlor?" queried Judy as daybreak shown through the open doors she was now bolting shut. Speaking with slight hesitation, I told her that I think I could become accustomed to the lifestyle quite easily. "You liked being in control of the men I had you pleasure tonight, didn't you Desir...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

Our Dinner with our Hostess

by wifestoy on Sep 16, 2017
Transsexuals & Crossdressers

After a very relaxing bubble bath I shaved Renee's legs and her sweet pussy, she gave me some pampering and shaved me. This was a real treat. I got a very sweet reward by Renee. She allowed me to eat some serious pussy after the bath. As we lay down on the rose petals the soft skin and mix of fragrance from the bath oils and rose petals was intoxicating. I g...