Gay Straight To Sissy Stories

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Cocklust

by TerriC on Oct 6, 2020
Gay Male

I was horny the moment I woke up. My cock was hard as I showered and got ready for work. I slipped into a pair of blue nylon panties, something I usually only did on the weekend, and finished dressing for work. The drive in was crappy, traffic sucked, but it wasn't so bad while in my panties. Wearing them may have been a mistake though, I was semi hard when...

Afternoon Fun Pt. 02

by Hawkeye1981 on Mar 6, 2018
Gay Male

Tim and his mom ate dinner. She was a typical working mom. Tim's dad had left years before. Tim listened but didn't really pay attention. His mind was completely on Bill's hard cock. How it felt in his mouth. Tasting the rich cum flooding in. Tim felt his erection throbbing in his pants. His balls ached needing a release. "Tim are you listening to me?" His...

House Rules Ch. 04

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Seven PRETTY PINK BOTTOMS The first step on my trip down that path happened one hot Sunday afternoon. I had just come out of my bedroom after spending a few hours in the pool. I was wearing a pair of loose fitting boxer shorts which hung low on my butt. I was drying my hair with a towel. Mr. Clemons was there to meet me in the hallway with that...

Transforming Tim

by oskarwild on Sep 25, 2017
Gay Male

The Elevator Rafe could hardly wait for his lunch hour to come. But he wasn't hungry for food. He was hungry for the new elevator boy. The new boy was just the type Rafe lusted after. He was short and slim; probably five-six and maybe a hundred twenty pounds at the most. And he was young. All of the elevator boys the building employed were high school seni...

Nephew's Readjustment Pt. 14

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn'...

My Wife Hands Me Over to My Dom Ch. 03

by FantasizeAndRealize on Mar 6, 2018
Gay Male

It has been almost three months since my wife Susan found out about my gay affair. Since she found out she has been handing me over to my Dom, in person, every week for our sessions. She has gotten to know Carl, my Dom quite well. They love talking about me as if I am not even there. Susan really enjoys taking me to Carl and picking me up after our session...

Gay Whore

by Bonemeal on Oct 12, 2017
Gay Male

It all began when I was hitching through rural North Carolina back in the early 1970s. I was a young, tight feminine looking man. Light brown hair and long legs. My eyelashes are naturally long and people have said I have eyes like a girl. I was in the navy and that particular day I was wearing my uniform as we did in those days while on liberty. I watched...

The Mas-gay-rade Ball

by BluJBooty on May 10, 2020
Gay

You are Vance the Second prince of the Royal House of Chardeny and the declared crown prince... and you hate it. Your entire life has been scheduled and decided for you. You take massive amounts of lessons on etiquette, swordplay, history, etc..., you have a fiancé from the ducal house of Argent that you have never met, let alone like, love, or even want to...

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First BBC

by smoothbtm76 on Jul 6, 2020
Gay Male

I always thought of myself as bisexual. I had gotten my cock sucked by older men who liked twinks and I had sucked cock in turn. I had topped older men and had my ass played with and toyed and even fucked a couple times but hadn't really gotten into that too much. I had been to bookstores and theaters and played there but nothing really changed. That is, unt...

Tame Cocksucker

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. The idea for this story was suggested by donaldelliott11, with thanks. ***** "With this ring, I thee wed," Angelica said. With this yoke, I thee burden, Artie's mind echoed, just one moment forgetting the perks that came with marrying this fat, moody cow. Everything had moved so fast. Artie had the good fortune of working f...