Transsexual Stories

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Tiffany's Deal Ch. 01

by MicheleNylons on Jun 24, 2019
Transgender & Crossdressers

Chapter One -- The Deal Author's note: I know very little about playing poker. I have played blackjack in a few casinos in the USA, Australia, Europe, UK, even Vanuatu but that's the sum of my experience with gambling. Blame any factual errors squarely on me rather than my researchers, Google and Netflix xxx Michele Tiffany was not the name on her birth ce...

Shemale Surprise!

by BigAndy922 on Sep 14, 2017
Transsexuals & Crossdressers

I'm a country boy. About a year ago I left my small town and moved to the city so I could attend university. Initially, I had nowhere to stay so I was going to move into my cousin Mike's flat for a few days with him and his roommate, Sandy till I found somewhere of my own. Mike and Sandy worked together at a law firm in the city. Mike had a fiancée` but he...

Hypergirl

by DiamondStar on Nov 30, 2018
Transsexual

Samantha Kirk is a young and reverse college student. Despite being reversed, Samantha has a body that most women would love to have. She is six foot tall with a slim figure. She has perky C-cup boobs, a cute bubble butt that you put stand a quarter on, and nice long legs. She was not always Samantha. She was born as Rick, but she started transitioning at 12...

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Fun in Dallas with a TS

by Stryk on Sep 16, 2017
Transsexuals & Crossdressers

This is the story of one of my first experiences ever with a TS. All of my stories are 100% true It is my goal to one day be able to tell all of the sexual escapades I've had, largely thanks to the Internet. I am an average looking, slightly overweight guy. I am no stud or jock by any means. . I'm about 6'0 and just over 200lbs. Slightly overweight, defin...

Night at Amber's Ch. 02

by simple_jack on Sep 14, 2017
Anal

As Amber and Kara entered the dining room, Dax, freshly ass fucked, hung by his wrists and ankles in the corner with butter dripping out of his ass and the last remnants of cum flowing down his semi-erect penis and onto the floor. On command from Amber, Kashton released Dax and sent him upstairs to bathe and get cleaned up for the second part of the night. T...

Brittany's Apartment

by mrflex37 on Jun 1, 2020
Transgender & Crossdressers

"This is a bad idea, this is a really bad idea," I told myself. Truth be told, skipping class is one thing, but skipping class to hook up with a transsexual you met on Craigslist is a couple steps farther. To make matters worse, I only had a one-hour window to get here, do whatever we are going to do, and get back before my friends found it suspicious that...

The Company

by WhiskeyIsGood on Aug 6, 2019
Transgender & Crossdressers

Here's one I've had sitting on my desk top for quite some time now. I meant to release it earlier this year but I had some trouble figuring out a few of the details, and it slowed me down. Anyway, I am happy to finally share it with you all, and I hope everyone likes it. I definitely have plans to make this a series if I receive good feedback. Whiskey To w...

Alpha Gamma's Secret Ch. 3

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-7- "This has been an important and exciting year for our sorority," said Jessie, House President, to the assembled sisters of the Northeastern University chapter of Alpha Gamma Tran. Today was a very special day. It was the annual Commencement Ceremony which marked a successful end to the school year. All the girls had gathered in their sorority house's sp...

Emmy's Iron Maiden Glory Hole

by hummmph on Sep 16, 2017
Fetish

It has been a few weeks since Emmy had her way with me at her house. We have a peculiar relationship. We are like the best of friends when out having a drink, as we are now, and then when it comes to sex it is like she turns into a whole other woman and just becomes this wild volcano, erupting lava flow after lava flow of controlling sexual domination. There...

Family and Friends Ch. 02

by SplitLicker69 on Sep 16, 2017
Transsexuals & Crossdressers

Gabi and I left early the next morning to open our gallery and deliver the painting titled Silhouette at Sunset to the buyer, Sam Strickland. He said he had a yacht in port and planned to debark soon. I saw his yacht anchored in the deepest part of the bay. It is stunning, sleek and at least 250 ft long. She glistened in the morning sun and I snapped severa...