Ladyboy Fuck Guy Stories

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Sex with Shonda

by rawpump on Sep 16, 2017
Transsexuals & Crossdressers

I'm a workaholic by nature. I love my job but that's not why I work so much. I work long hours simply because when I get home I don't quite have anything productive to do. I just sit down in front of the television or I chat over the internet. Life at home is dull so the best solution seems to be engaged in work. Often on Friday, after work, I head to the...

28-year-old Bisexual Stepfather Ch. 18

by walterio on Apr 16, 2018
Novels and Novellas

AUTHOR'S NOTE: Reader feedback was to continue with this series. Thank you! Reminder: This series contains straight sex, bisexual sex, gay sex and incest. ***** DAY TWO OF THE CRUISE That morning Dustin was up early and decided to get a quick workout in before breakfast. He went to the fitness center whish was virtually empty. There were only a few other...

My Cleaner

by gendidi on Sep 13, 2017
Transsexuals & Crossdressers

I'm a 40 years old married man. My wife is much older and we stopped having sex a few year ago. We spend a few months a year in our homes in UK and Malaysia. I have never had experience with a ladyboy my whole life. Just not my cup of tea. We went to LOS a few times and saw ladyboys on the street but nothing happened. Due to my looks, I did attract some femb...

My Diary Ch. 01

by sexually__confused on Sep 16, 2017
Toys & Masturbation

This diary will chronicle my explorations into my sexuality and explorations of my deepest forbidden desires. Thank you for any feedback, D. Chapter 1. March 27, 2010 I am somewhat confused and frustrated in my sexuality. I am a 28 year-old male and am relatively straight. I do, however, enjoy anal play during masturbation - a fact I have not shared with m...

Getting the GED

by turo69 on Sep 16, 2017
BDSM

Part One Well how did I get here? Bob Tucker, newly retired at 55, not buff but not quite squishy, fairly comfortable, never married and still a certifiable horn dog. An athlete through college and still pretty active, but with an overactive sex drive. My investments and real estate holdings together with a 20 year pension courtesy of our local school distr...

Meat

by xploring96 on Sep 15, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. * James was supposed to meet a friend for a late dinner at "Meat," the best steak restaurant in town. Then just as James arrived, he received a text informing him something had come up, and...

Home Again

by PeggyBuxton on Mar 6, 2018
Fetish

The senior year at the university was over at last. Tom had already broken up with Carrie. She was his mother's age and married. It wouldn't have lasted no matter how good the sex was. There had been two others before her, both similar ages, both married. He was handsome and could have had his pick of beautiful coeds. They never seemed to offer the same exci...

Cockatoo Pt. 17

by nikkiesilk on Sep 19, 2017
Transsexuals & Crossdressers

Previously in Cockatoo James, recently divorced, travels to Bangkok on business for a fresh start. He meets Alex, a friend from their university days, whom he discovers is now transgender. Alex and her partner, Areeya, a Thai girl, run a successful restaurant and ladyboy bar on Koh Samui, an island off the coast of Thailand. James falls in love with Alex an...

Cockatoo Pt. 20

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** I glanced back as I left the bar at Tony, who was smirking all over his face and I swore to myself I would wipe that look off his face as soon as I could. I hurried back to the apartment, where Alex was working on some business for the restaurant. I let her listen to the conversation on the tiny recorder I had used to tape everyt...

Jamie's Descent Pt. 03

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

The limousine took me to Harley Street, home of the UK's private health industry, for the medical Vanessa had mentioned. To me it had seemed less of a medical and more of a preparation for something. There were a lot of the usual blood pressure tests and urine samples, but there had also been a lot of measurements taken, especially around my upper body. The...