Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

Dog Kennel

by Dylan987 on Sep 19, 2017
BDSM

I waited in the car for ages trying to summon up the courage to go through with my idea. After finding the human puppy school on the net I had contacted the 'trainer' and he'd invited me along to his kennel to see how I liked it. So here I was, and I decided to go ahead and give it a try. I knocked on the door of the ordinary three bedroomed semi and must ha...

Evening Drink

by PaulaApril on Mar 12, 2019
Erotic Couplings

Michelle swirled the wine glass and giggled. Its contents rose up towards the rim before sliding back. It moved slowly, like a syrup. She watched until it settled back before raising her eyes to Matt. He lay back over the sofa with his feet apart slowly stroking his erect cock. "Hmm. You've gone to a lot of effort." She said in her squeaky girly voice....

A Fairy's Tail - Origins Ch. 01

by EHMiller on Jul 31, 2019
Sci-Fi & Fantasy

Author's note: All characters depicted in this work of fiction are 18 years of age or older. These chapters are an exploration of the backstory of our favorite fairy Fiellen and may not contain as much explicit sex as you have come to expect from A Fairy's Tail in some chapters. *** It was nothing more than two worn down wheel ruts where folks in days p...

Hunted Blood II: Dark Reign Ch. 2

by AmenRa on Sep 15, 2017
NonHuman

Japan was much the way Michael Stone remembered it. He had spent a great part of his youth here. He looked at the buildings as the taxi he was in drove through the streets of Tokyo. Not much had changed. The neon signs still glared above, while the streets and sidewalks were covered in people of all races. That would make hunting here harder, he knew. The t...

Duplex Ch. 11

by naughtyboyincali on Sep 25, 2017
Exhibitionist & Voyeur

When Mary pulled into her garage and closed the door behind us, I could finally relax. Except for a brief stop at a rest stop, I'd been laying back in her passenger seat, completely naked, and hairless with an erection. She kept me excited the entire time. When she would pull into the left lane to pass cars, I would press myself as a far down into the seat a...

Sex Education Class

by DariusTDK on Sep 13, 2017
Group Sex

My name is Nicola, I'm 23 and I'd been checking out adult contact sites on the Web for some months. The results had been astounding. I started doing this in the first place because I like sex very much indeed; I had recently finished with a boyfriend and didn't want another relationship right away. Now, for the very first time, I discovered the joys of casua...

Zeb, Deborah, and The Garbage Men

by flabuf on Sep 17, 2017
Loving Wives

I'm enjoying writing here on Literotica and appreciate the kind comments of many readers. Others, you know who you are, love to leave comments which are just rude anonymously. If that's your ilk. Please take this invitation to move on. If not, I hope you enjoy my take off on Geoffrey Chaucer's part in 'A Night's Tail' where he told his tormentors he would ev...

Untitled Ch. 01

by elite1 on Sep 16, 2017
Sci-Fi & Fantasy

This is chapter 1 of the untitled series. One day I will be creative enough to come up with a name but for now this will have to do. Each chapter is taken from the point of view of a specific character, it will all start to come together in the future after the characters have all been introduced through their respective chapter. As in the prologue, this is...

Toy Boy Joy

by alexcarr on Sep 17, 2017
Mature

To be quite adamant I'd had it up to here with George, my ex who did my head in. He'd lost all feeling for me, romantic or otherwise and the 'otherwise' was like doing it by numbers, absolutely no fun at all. I was thinking; "why am I doing this if it is doing nothing for me anymore?" The only one who was getting his fill was George with a quick in and out j...

First

by Samuelx on Sep 14, 2017
First Time

Right now, I am lying in bed. There is a gorgeous young man next to me. A fine and sexy young man. Blake Mitchells is his name and he's my best friend's twin brother. He is lovely and we've just spent a wonderful night together. We made love. It was a first for both of us. I feel wonderful. It feels great to be next to him. Maybe it's the magical time we've...