Strapon Boy Stories

106,036 results
Orientation
Length
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Infinite Scroll

Confessions of a Blowjob Addict

by oraldave39 on Sep 12, 2017
Fetish

I would like to thank "Belle" for sharing her experience with me about losing her virginity. She is a close friend and the inspiration for this story. Belle did want me to relay to the readers that although she does go to adult bookstores and glory holes, she goes as a woman and only a couple times a year. I am a 37year old single fifth grade teacher. I am...

Irene Pt. 02

by arislesbos on Sep 15, 2017
Loving Wives

I was watching her face to catch any signs of emotions, as she removed the headphones. But she had a poker face for the last ten minutes. She was fully concentrated on the music and trying to hear every single beat and note. "So?" I said. "What do you think?" "I like it," she said. "You sure?" "Yeah, absolutely. You have talent, boy. That's fantastic."...

You Gave Me a Mountain Ch. 01

by DG Hear on Sep 14, 2017
Non-Erotic

Thank you to my editors LadyCibelle and Techsan for making this story a much better read. * I was sitting there in the restaurant in the quaint small town where I used to live. They had one of those tabletop jukeboxes and I was looking through the song titles. I remembered how so many songs seemed to be a pathway for me. I slipped in a few coins and pushed...

Sally Ch. 04

by Rosko Busby 2005 on Aug 29, 2017
Erotic Couplings

Chapter 3 concluded: "Although she is now 34 Sally still enjoys an occasional session in front of the cameras but her story concludes, as far as we're concerned, with a favour for a young friend she met at a recent party." Chapter 4: The final chapter Ambar becomes a mother. It's now August 2014. Ambar, Veena (her mum) and Sally are in the Oxford hospita...

The Therapist Ch. 07

by sm8100 on Sep 17, 2017
Fetish

It was impossible for James to focus on his work on Monday as the events of the day were little more than a prelude to his 6:00 PM appointment with Julia. The attending excitement and anticipation that accompanied regular visits with Julia were practically overwhelming for him to even comprehend. James thought about the time he had spent with Julia in recent...

Hunt of the Skinwalkers Ch. 01-02

by CalebHarwood1988 on Sep 16, 2017
NonHuman

Chapter 1 Friday December, 31 1999 New Year's Eve It is New Year's Eve in Havenwood, a small mountain town in the Golden Forest. Named for it amazing sunsets that gives the whole forest a golden hue. Deep in the forest, in a small log cabin a party is going on to celebrate the turning of the new millennium. In front of the cabin is a large yard covere...

Gangster's Moll Ch. 01

by LaRascasse on Sep 16, 2017
Novels and Novellas

This chapter is set roughly one year after the events of An Unlikely Romance Ch.08. I would suggest reading that story to get an idea about Monica. If not, you can just leave it at her being New York City's most ruthless cop, willing to do anything to get the job done. As always your comments and votes are much appreciated. "Get inside the mind of your ene...

Dan The New Girl Ch. 03

by janetjoneslovesyou on Mar 5, 2018
Transsexuals & Crossdressers

Back at Lucy's room, Dan put down the dainty bags of lingerie and girly clothes that she had bought for him. He had been totally and magically transformed into a girl for nearly a whole day now, and every moment was a thrill. He was ultra-conscious of his body - especially his gorgeous 32C boobs, firmly held in the bra that had turned him into a curvy and se...

Lola Lickett - Queen of Porn: Ch. 02

by FreddieTheCamel on Aug 31, 2017
Humor & Satire

Devlin Carter knew how to talk. When he was a skinny door-to-door household products salesman, people would buy toilet cleaner they never used just to shut him up. A random suitcase filled with dildos and X-rated VHS videos crossed his path and, after selling the lot in one day, Devlin knew that his future lay in the sex industry. Years later the VHS video h...

The Lost Prince Ch. 02

by notbreckenridge on Sep 19, 2017
Transsexuals & Crossdressers

Our journey from Camp Number 147 was a very sad and long one. I managed to sneak a few last peeks of the place that had been my home for the years during which my life had changed the most. Doctor Gorski watched me depart as long as he could, but the pain in his face and the biting cold soon proved to be too much for him. I imagined him going inside to rest...