Gay Sissy Transformation Stories

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It Could Be Worse Ch. 06

by eviltwin52 on Sep 14, 2017
Gay Male

In chapter 5 Leon took control of what he called his new sissy and fucked Cin into submission. We both became addicted to his superior black cock. Besides falling for his cock, Leon's predatory nature was evident. He wants Cin and I to prostitute ourselves for him. In the throes of black cock lust, we agreed. It could be worse Part 6 "Did you remember t...

I Turned Myself Out

by drmweaver705 on Jan 29, 2020
Gay Male

All characters are 18 or over. ***** My journey must have begun with my discovery of porn. When I was eighteen, I discovered a trove of porn magazines hidden out in the abandoned shed of a derelict and condemned house near my childhood home. This was the first time in my sheltered life I had ever seen anything like it. The magazines varied from soft nudit...

Nephew's Readjustment Pt. 16

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. ***** That evening Nicholas took a very long shower. He was finally unlocked again, and the soreness of his anus made it difficult to clean. Despite being free,...

House Rules Ch. 06

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Eleven WORK TO DO & BUTTERFLY KISSES I fixed breakfast the morning for the both of us. I was wearing pink hipster panties with the word SASSY across the seat and a white cami with pink trim which showed my flat belly. The material was lightweight and tight against my lean torso. You could clearly see my nipples which were as pointy as gumdrops. My...

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...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....

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...

Center of Attention Ch. 02

by michbics on Sep 15, 2017
Gay Male

I woke up the next morning with a hard on and a very sore ass. In saying that, it didn't take me long have the urge to call John. The escapade I had with him and his friends made my transformation to a cock loving whore complete. I couldn't think of anything else other than a big cock fucking my ass and one in my mouth. I was longing to go another round with...

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...