Shemale Gloryhole Stories

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Infinite Scroll

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...

SEXretary

by sexy_jessie on Sep 26, 2017
Transsexuals & Crossdressers

Sam Nichols had a comfortable, reasonably well paid job in a computing firm called Stewart Computing. He was twenty two and had recently graduated college and had been lucky to find such a good job in the firm on the edge of San Diego, just a couple of hours drive away from where his parents still lived with his younger sister Lizzie in the small town of Riv...

The Swagman

by ausfet on Mar 14, 2018
Non-Erotic

Urban sprawl is an incredible event to witness. Human settlement is not unlike a seething mass of ants, growing ever stronger and larger each week. 'God, it's just so ugly isn't it?' Caroline asked. The development she was staring at from the passenger seat of my car was the epicentre of my new job. The average lot was five hundred square metres and with o...

A Ski Bunny is Born Ch. 02

by Nikki H on Sep 18, 2017
Transsexuals & Crossdressers

My first real man. Hugs and kisses to everyone who contacted Kim and I expressing how much you enjoyed our first episode. This is the second part of our life story so far, and is the first follow up to 'A New Ski Bunny is born'. It recalls the first time that Kim and I included guys in our sexual exploits. After I made the big decision to change my lif...

Amanda and Me Ch. 06

by Tallnhard1 on Sep 11, 2017
Transsexuals & Crossdressers

The room was still dark when I awoke. Blinking the sleep from my eyes I sat up in bed and glanced towards the window where the faintest of light was beginning to creep in under the blinds. It was definitely too early to get up so I lay back down and closed my eyes, letting my mind wander over the last week of my life while I listened contentedly to the sound...