Gay Sissy Boy Stories

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The Birth of a Sissy

by sissymedic1426 on Sep 14, 2017
Gay Male

After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the...

From Alex to Lexi Ch. 02

by oskarwild on Sep 14, 2017
Gay Male

Lexi drifted back into wakefulness, opening his eyes slowly. At first he was disoriented, not remembering where he was or how he had come to be here. Then he became aware of the man lying next to him. He could feel his hairy chest and feel his stomach rise and fall against Lexi's back with each breath he took. He could feel the man's large hand resting on hi...

Power Trip Ch. 05

by Wally_West on Sep 26, 2017
Gay Male

Colin stood in front of the toilet relieving himself through the opening at the tip of his chastity cage. He was growing used to its weight and presence, finding less discomfort from the device every day. He was happy it was Saturday and he didn't have to go to school; Colin wondered what his step-mother had in store for him, as their sexual activities were...

Turning Myself Gay

by bart_allen on Apr 10, 2018
Gay Male

How did I end up as... well, you'll see. That's the whole point of writing this all out. A little story about how my life got flipped, turned upside down. Humorous references aside, my life certainly has changed, and was done on purpose. I guess I should start at the beginning, but that's difficult. My start was boring. No different than most people, I suppo...

An English Boy Gets Turned Out Ch. 03

by RustyRover on Sep 14, 2017
Gay Male

Mr Tobias was at work earlier than normal today. He had an early meeting with Mick to discuss the new star of their porn website. The Porn industry used to be a license to print money but that had changed over the last few years. Now there was more free porn available than paid for porn. Between Porno YouTubes knock offs, torrents and all these other sites e...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...

I Turned Myself Out Ch. 04

by drmweaver705 on Sep 14, 2020
Gay Male

All characters are over 18. This story contains bisexual and cuckolding activity as well as fetishistic name-calling. If you don't enjoy these things, this might not be the story for you. *** Porn seduced me early in life and, even as a married man, it commands part of my loyalty to this day. It happened that I became bored, or maybe just desensitized, to...

Danny Darling Ch. 05

by bjmichaels on Sep 14, 2017
Gay Male

"UNBUTTON YOUR SHIRT AND OPEN YOUR SLACKS, YOU LITTLE WORM!!" she screamed in my ear. I stood there stunned; frozen in place. I couldn't believe the abrupt change in Mrs. Nelson's demeanor. The normally sweet, good-natured woman had never made even the slightest derogatory comment to me, and she certainly never raised her voice when she reprimanded me for...

Sissy Bottom Has a Nite Out Ch. 02

by lostsoul1974 on Sep 14, 2017
Gay Male

Last night, my friend Eric and I had some really hot sex down at the Adult Theatre. Eric had me wear a pair of my wife's panties and I was a sissy fuck-boy for a whole theatre full of horny men. My wife is out of town for the weekend, so we are gonna be as lecherous as two bisexual fuck-buddies can be. This morning, I awoke to the sensation of Eric's hand s...

Cum on Panties

by jakladd on Aug 30, 2017
Gay Male

Cum on Panties - Our phone sex is always so hot, you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings & high heels, telling me how perfectl...