Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

Of Two Minds

by Cyanlot on Sep 12, 2017
Transsexuals & Crossdressers

The middle portion of this story was intended to be conveyed in two separate columns, providing parallel presentations of different perspectives on the same events. Literotica's software does not permit such formatting. Accordingly, I have interwoven the material that was to be displayed side-by-side, formatting one portion normally and the other in ALL CAPS...

Neighbours Ch. 02

by chinookwind on Sep 14, 2017
Erotic Couplings

2.01 Mary, Sara and the Neighbourhood: 2.02 Mary, Sara, The reception: 2.03 Jessie and her Sybian Lover: 2.04 Jamie and the Semen Extractor: 2.05 Susan and her Robotic Lover: 2.06 Daniel, the Harness and his Sybian Lover: 2.01 Mary, Sara and the Neighbourhood: To the daily commuter, Willow Falls appears to be a nice, quiet suburban neigbourhood. Singl...

Made to Obey Ch. 12

by madetoobey on Aug 26, 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). I'd been forced into a chastity cage and made to wear panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being uncovered. I'...

Queen Yavara Ch. 29

by White_Walls on Sep 24, 2019
Sci-Fi & Fantasy

Part Ten: Adrianna's Story Author's note I decided to introduce the character of Adrianna (formerly Thomas Adarian) gradually throughout the story. At first, you only hear accounts of him, then you only see him through the eyes of other characters. It is only at the beginning chapter 20 that I let the story play through Adarian's eyes. I wanted to give the...

The Priestess of the Night

by Liver96 on Mar 9, 2020
Transgender & Crossdressers

Apologies for delay... A new round of my favorite thematic, Ancient History. Another shemale on male story, a little darker and rougher than the previous one (A Greek Woman In The Trojan Palace), a lot of betrayal and dishonesties in this one. Again, this conception is not intended to be strictly stick to Official History and Tradition, big thanks to my frie...

The Green Plague

by ScumDumpster69 on Nov 18, 2019
NonHuman

Author's note: Hey, this is my first time testing the waters of fantasy writing. It's a story about a feminine boy and a large, hulking shemale orc, during an ongoing war between orcs and humans. WARNING: Contains non-con. There is also a gore scene early on in this chapter, but it's not related to sex in any way, and doesn't involve any innocent or undese...

Lilith's Emporium - Rise of Ezranox

by maestro84 on Jul 16, 2019
Erotic Horror

This story is a special request and links to the Rak-Sasha series by author of the same name. Please enjoy. ***** Doctor Thompson, was so excited about the latest delivery to the museum. She had been waiting years to get a look at this book and now that it was here under the same roof as her she couldn't wait until morning as she slid her ID card and heade...

Made to Obey Ch. 13

by madetoobey on Sep 9, 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). I'd been forced into a chastity cage and made to start wearing panties all the time. Furthermore, a curious email I'd sent to "Bowser" before I was married led to my past fraudulent activity being unco...

Code Name Tequila Ch. 06

by Travel_by_day on Sep 15, 2017
Transsexuals & Crossdressers

"Code in." "Tequila, three-eight-zero-five-seven." "Hold please." There was a click on the line, and then silence. The amount of time it required for the line to be picked up was much longer than usual. Finally, another click and a voice came on the line. "Tequila, this is Black Oak. Where are you?" "An internet cafe in Cordoba, Argentina, about 3 bloc...

Christian College Sex Comedy Ch. 18

by FinalStand on Sep 25, 2017
Erotic Couplings

*If you make one person happy, you save the World. Make a million people happy and you become a politician* (Thanks for Fortima's presence fixing so many of my mistaks (Oddly there is no sex in this chapter; just prepping for the next rollercoaster) (Yes, this tale is supposed to be somewhat humorous and outrageous too. While not always comedic, I'd lik...