Gay Sissy Strapon Stories

795 results
Orientation
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Infinite Scroll

What Being a Sissy Wife Means to Me

by SissyWife on Aug 18, 2017
Gay Male

I am a sissy wife. I hate clichés as much as the next girl, but sometimes they make for the most apt of descriptions. I have a job, friends, and a life. I go out, I go out for movies and drinks. I enjoy long walks and drives, and I love travelling to new places and locations. And yet, there was something missing. There was something that was needed. I found...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

Sissy Veronica

by slavegurl_veronica on Sep 16, 2017
Gay Male

Hi. My name is Veronica. I am a 21 year old, 135 pound, pale white sissy boy with dark brown eyes and hair. My master is Derek. He is 6 ft 5 in, 175 pounds of beautiful black stud. I have a sissy playmate named Alex who is also Derek's pet. As I already described in an earlier story, Alex's sister Cecilia is responsible for hooking us up with Derek and intro...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...

The New Gym Member

by exaucer on Sep 14, 2017
Gay Male

Wanting to get in to better shape I decided to join a nearby gym. Moreover I was feeling the need to look at other men naked. With your experience you will know the type of young man I am. I am the one who spends longer than is necessary in the shower, stealing looks at other men's cocks. I am the young man who is slow to get changed, sitting there pretendin...

My Girlfriend Turned Me Gay Ch. 02

by keithdavis1010 on Sep 25, 2017
Gay Male

Note: This story starts where "my girlfriend turned me gay" ended. These stories are for entertainment purposes. I am not making a statement or soliciting debates about consent. Not to wax philosophical but how many of us are really free to make choices. As hard as it is to understand for some, many straight men do fantasize about being taken anally – usuall...

Taking the Neighbor Ch. 08

by jjdtx on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. *** Melissa and I fucked again in the pool house, then headed inside for a hot shower, then off to bed. She was dozing when I got a text from Allen. "You up?" "Yes" I replied. "How was the rest of the evening with Wendy?" "Great, still no head, but jerked me off!" "Are you home yet?...

Party Pizzazz Ch. 02

by bjmichaels on Oct 6, 2020
Gay Male

Party Pizzazz Ch. 02 by BJ Michaels If Tommy hadn't kept such a close eye on me all night at the party I would've ended up as a boy-toy for one of those rich men. That's what he told me afterwards in the car on the drive to his apartment. "Lucky for you I happened to overhear those five assholes bidding on you or you'd belong to one of them now," he said...

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....

My White Boy Sissy Pt. 01

by wolf_hunt on Feb 25, 2019
Gay Male

This is part 1 of an ongoing series. It's just an intro with only a blow job scene. In future chapters there will be more including forced feminization, anal, humiliation and much much more. Hope you enjoy my story. All characters involved in sex are 18 or older. This is from the perspective of a black teenager as he turns a sissy nerd into his bitch. ****...