Sissy Boi Stories

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I Am Sissy

on Apr 29, 2025

Hi boys, my name is Eli but I now go by Eve. I finally decided to come out of my inner closet and allow myself to be what I really want to be… a pretty sissy boi that craves cocks, lots of cocks everywhere in or on me. I have always been a small and slender boy, even in high school before I graduated, I looked like I was younger, I even had some of my teache...

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

X-Change: The Frat House Blues

by MrYowman on Sep 16, 2017
Sci-Fi & Fantasy

The world had been changing rapidly. Maybe for the better, maybe for the worse, that was yet to be determined. But the progressive political movement of the early twenty-first century had definitely made grounds, if not economically, at least socially, especially where sexual and gender norms were concerned. Science too, had made this new world more bold and...

The Ex's New Toy Pt. 03

by Urtoy2be on Sep 15, 2017
Fetish

Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind. The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

Cleaning Her Kitchen

by michaelssubmission on Sep 17, 2017
BDSM

"Today you will learn to clean the kitchen, but more specifically how to clean my kitchen," she said, looking directly at me. "You will begin by going to the cabinet above the stove and removing the box that is there. Place it on the floor next to my feet. I reached up and opened the cabinet. I am not tall and it meant reaching up on my toes. Naked while sh...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...

Sutters Hollow Ch. 02

by BlackMadonna on Nov 19, 2018
Sci-Fi & Fantasy

SugarPucker Creek If there was one name in all of Sutter's Hollow that was almost always linked with troublemaking and mischief, it was Bobbi-Jo Butters; just plain BJ to those who knew her well. Bobbi-Jo was a down home southern tom boy with short muss-cut dark brown hair, freckles in all the naughtiest of places, and big beautiful baby-blue doe-eyes that...