Gay Turned Sissy Stories

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PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

The Parade Pt. 03

by Paperpiece on Jul 13, 2020
Gay Male

'Word' / words enclosed by apostrophes = thoughts "Word"/ words enclosed by quotation marks = spoken words *** Though the scent of coffee stirs me, it's the plug getting shoved in my ass that actually jolts me awake. Sore all over on a bed that isn't mine, tangled in its sheets, there's dried cum on my face, back, and between my thighs but there he is, lo...

The Set-up

by drmweaver705 on Jan 29, 2020
Gay Male

All participants are 18 or over. ***** It promised to be a very fine session. Amanda had tested all the restraints and Victor was held firmly in place on the bed. She had promised to fulfil his deepest fantasies today. It was Saturday, they were childless and neither of them had to go to work. They could spend all day in bed. He was naked and his cock was...

Turned into a Sissy Slut Ch. 01

by i_like_it_like_that on Sep 14, 2017
Gay Male

My name is Mark. I'm 18, and am around 140 lbs, thin, with a kind of girly ass. I began to fully embrace my love of dicks by watching hours of gay porn and at the same time embraced my feminine side by buying and hiding a lot of women's clothes. Still, by the time I was 18 and going off to college, I had not done anything with a man. It's not that I didn't w...

Turned into a Sissy

by drogon01 on Sep 14, 2017
Gay Male

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested. I was at university at the time but was home...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Becoming Mark and Janet's Girly-Boy

by BuckyDuckman on Mar 30, 2020
Gay Male

Who knew taking your turn at washing the dishes could turn sexy? That's exactly how it started as Janet squirmed up close to me, wrapping her arms around me from behind and pressing her chest against my back. I might not have had hands on my back but I swore I could feel her stiff nipples poking me. "Hey baby?" she cooed, kissing the nape of my neck and se...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

Let It Be: Eric & Maury

by sissyrikki17 on Oct 15, 2017
Gay Male

Eric had just come in through the screened side door to the lanai after mowing the front yard. He'd removed his sweaty workclothes and now turned under the lanai shower in the nude. The shower water was tepid but relative to the late-morning summer heat it felt positively refreshing. So refreshing, in fact, it was giving Eric a hard-on. From a short distanc...

Turned at the ABS Ch. 02

by Want2serviceU on Aug 29, 2017
Gay Male

I was half sitting half kneeling on the floor of an ABS with cum dripping out of my ass, cum on my face in my mouth at least the taste was still very much in my mouth. There was still a few men looking at me while I stood up gathered my clothes. Two young white guys with cocks smaller than I had just had grabbed me and used me like a sex doll, then pushed me...