Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

Stevie's Journey Ch. 03

by gbr2004 on Dec 2, 2019
Fetish

I get up and put on some of my regular clothes, workout shorts and a t-shirt and flip flops. Try to digest what happened yesterday and how everything just spiraled out of control and now I find myself in this impossible position. It's like all choices have been taken from me and this group of people took over my life. It was exciting but I can't be doing the...

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

Yes, Mommy Ch. 03

by searic on Sep 17, 2017
BDSM

Here is the third installment of a story of loving spouses, the husband a sissy submissive to his Mistress/Mommy. She has invited over a girlfriend to witness and perhaps participate in his humiliation and degradation. At the end of Part II, the women were on the couch and the little sissy was on the floor. He obeys his wife's command to beg. * "Oh, please...

Dress Up For The Girls Next Door Ch. 02

by JackorJill on Jul 15, 2020
Transgender & Crossdressers

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot. “I have a few cold beers in the fridge,” she cooed. “Why don’t you take a b...

The Right Girl for the Job

by Stephen_Heathcote on Oct 13, 2017
Transsexuals & Crossdressers

"If you aren't here for sex, then why are you here?" Lacey asked. It was a reasonable question, given that we were sitting in the bar area of a brothel. "I have some very specific fantasies, things that I would never ask a civilian to do," I said. "Why not?" "Too embarrassing. I don't even know if I can tell you," I said. "There's nothing you can tell me...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

My New Life

by gbr2004 on Jun 1, 2020
Fetish

This story is totally fictional and involves forced fem, discipline, interracial sex, among other kinks. Kind of a long story with probably too much dialogue and not enough sex but I hope you enjoy it. *** I'm not going to take any more shit from this asshole. I'm talking about my stepfather. Sure, he's nice when Mom is around but when she isn't here, he t...

Trip to LA Pt. 02

by gbr2004 on Mar 3, 2020
Fetish

This story is just a figment of my imagination and shouldn't be read if you aren't into forced fem, sexual service and discipline. Otherwise, I hope you enjoy the story and I love to hear comments about my writing. *** All I can think about is how out of control this all is. Here I am, in LA, god knows where, dressed up in pink and white and looking like...

The Tasting

by IraIrene on Sep 16, 2017
Transsexuals & Crossdressers

"Mmm. You're pretty in frills, sissy. Pink polka dots look good on you, and your lipstick is just so. Lift up your skirt for me, show me the panties you picked out." "Aww, those are too small. Your cock is poking out. Hee! Now turn around and wiggle your cute little tush for me. Good sissy boy. Now get down on your knees." "I suppose you're wondering why w...