Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Futanari Notebook Ch. 23

by sexgundam666 on Jul 31, 2019
Sci-Fi & Fantasy

Life is strange. It throws absurdities at people without warning. Mary having a dick was one, and Dakota being gay was another, then Zoey... Now Ashley had been afflicted. The signs were clear after the first three. Rachel hadn't blinked when Dakota acted weird, she had expected the girl was gay or at least bi, but the former queen bee of Saint Puella was an...

Made to Obey Ch. 03

by madetoobey on Jun 24, 2019
Transgender & Crossdressers

Reprise. I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. Could I pass the tests? We reached the li...

Sissy PRIDE!

by nancyvasquez on Aug 27, 2018
Transsexuals & Crossdressers

I'm just sitting around, painting my toenails, and thinking how blessed I am to have been born a sissy. Of course, it wasn't always that way – I wasted so much of my life trying to fight my reality. It wasn't until I went through puberty and I saw that I was not developing physically like the other guys my age that it really began to concern me. I saw them,...

Daddy's Droid Ch. 11

by Cordelia Speedicut on Mar 9, 2020
Sci-Fi & Fantasy

Chapter 11: Tuesday, Again (still) - The Bootique Less than an hour before, I'd bolted awake to find myself seated on a metal chair with no personal memories to speak of, in a concrete room full of villains and stolen pleasure-droids. So that sucked. Also, my butt had felt like I'd just been reamed and, disturbingly enough, I'd been less concerned about the...

A Masseuse Named Eve

by Legatus on Sep 13, 2017
Transsexuals & Crossdressers

This is my first submission, I hope you enjoy it. I tried to focus on character development, so this may be a bit longer than most are used to. **WARNING: This story contains a hermaphrodite/dickgirl/shemale with an inhumanly large cock and lactating breasts. There's shemale on male sex, lactation, and unrealistically large cum shots. If that isn't your thi...

My Journey Ch. 07

by npanxx on Sep 25, 2017
Transsexuals & Crossdressers

This is the seventh installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapters 1 thru 6 first. Thank you to all who read my first six submissions and provided feedback. All characters in this story are over the age of 18 years. _________________________ John came down the hall in his terry cloth robe and t...

Code Name Tequila Ch. 07

by Travel_by_day on Sep 14, 2017
Transsexuals & Crossdressers

The Brazilian immigration agent looked at the passport. American. April Cho. He looked at the picture, and then up at the woman standing in front of him. Thin, tall Asian woman. The woman smiled. The agent looked back down at the and flipped through it until he found the Brazilian Visa. It was a ninety day work visa. "Purpose of visit?" the guard asked in m...

Barbie Jo Adventures Ch. 06

by barbie_jo_69 on Sep 13, 2017
Transsexuals & Crossdressers

Chapter 6: Barbie Jo's New Girlfriend This story is a fantasy story, and with all fantasies we can imagine that no evil exists. That also means no disease, so with no disease to transfer to someone else, no need for protection. Remember it is a fantasy world, in the real world evil and disease exists. Protect yourself. * Saturday When I woke up, I was al...