Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Thai Graduation Photos

by StarfireMayo on Sep 17, 2017
Loving Wives

Part six of the erotic photo journals of an English Teacher in Thailand. * Noi looked up at me with those cute mischievous little eyes of hers. Her mouth encircled my cock tightly while her head bobbed up and down on my dick, helped by my right hand firmly pushing down on her head to ensure she took all my long white cock deep into her throat. She had wok...

Makati Ch. 08

by massageaddict on Jul 15, 2020
Novels and Novellas

Chapter 8 I awoke early, having a busy day in front of me. After getting cleaned up and spending some time packing up my clothes and work items, I headed down to breakfast about 7:30am. I stopped off at the restaurant and ordered my coffee and an English breakfast and headed to my seat in the smoking area. When I rounded the corner, I was a little surprise...

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...

Craigslist Encounters Ch. 01: Craigslist Cumslut

by xploring96 on Feb 5, 2018
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission, and denigrating terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. There maybe additional chapters to this story depending on how this is one is received. If you would like to see a second chapter let me know b...

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...

Red Pt. 03

by aausaheb on Jan 8, 2018
Transsexuals & Crossdressers

*Sometimes our heart reacts in ways we would have never imagined. Certain keys unlock certain lockers in our brain, which we never knew existed, and new caves reveal themselves; caves that are waiting to be explored. This is a continuation of the adventure Avi wanted to go on but has now gotten Shana interested and excited. To see how the unknown winds drag...

Made to Obey Ch. 01

by madetoobey on Jun 18, 2019
Transgender & Crossdressers

Let's get this straight. I'm not gay, not a sissy or faggot, I'm a normal 30ish heterosexual guy okay! So why you might ask am I writing this dressed in a dark blue dress, black stockings with suspender belt, light blue panties with a white polka-dot pattern and bow, matching bra, 3-inch-high-heels, with my cock in a chastity-cage and with my hair, make-up,...

Promiscuous Parents and Sons

by walterio on Sep 14, 2017
Novels and Novellas

PRELUDE While Pete, Kurt's dad was spending the day with Sandy's mother Lisa, the two twenty somethings were involved with passionate sex. Sandy was sitting on Kurt's body with a thick cock buried in his ass. As Sandy rode his muscular neighbor, Kurt reached up with both hands and fondled the effeminate blonde's cute titties and tweaked the sensitive nipple...

Learning About Kathoeys

by walterio on Dec 2, 2019
Transgender & Crossdressers

PRELUDE Andy Morris was waking up slowly and as he stirred, he felt the presence of another body in bed. He rolled to his side and saw the lovely Jasmine who had stayed the night. She was on her side facing away from him and he took in her naked beauty. He recalled the night before and the marvelous sex they had together. As he looked at her incredible ass,...

Recruited Ch. 01

by Rstyusameg on Sep 2, 2017
Transsexuals & Crossdressers

All characters are fictional, except me, everyone in the story is over 21. My stories will involve, male/male sex, cross-dressing, and bad language, so if this offends you please don't bother reading. I stare at myself in the bathroom mirror, carefully applying finishing touches to my pink lipstick, I'm ready. I walk downstairs to fix myself a drink, exu...