Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

Sailing Away Ch. 18

by Jasmyn_White on May 12, 2020
Fetish

Chapter 18 It's hard to tell day and night when your quarters are below decks. The advantage is you can sleep in the dark as long as you like without disturbance. Point is, I fell asleep hard when we got back to the boat. We pulled away from the dock, and with the diesels turning, I have no idea what time it is, nor how long I've been out. It's a low rumbl...

"Friends" Ch. 01: Rings

by SylentWriter on Sep 13, 2017
First Time

Originally posted 5/12/16. Edit (5/27/16): In the weeks since I posted chapter 1 I have learned a lot about creative writing. I've revised chapter 1 to be more consistent in style with chapter 2. I hope it's an easier read. I want to thank Todger65 for re-editing chapter 1. He has saved me from embarrassment several times now. Disclaimer: This is a First...

My Amazon Army Ch. 01

by reynolddd on Sep 11, 2017
Sci-Fi & Fantasy

*This story mixes sci-fi, drama, action and lots of sex and violence. I hope you enjoy it. Chapter 1: The Revival I sat on my rocking chair, looking out on the lake. It was late in the evening and the sun was setting. Things were peaceful and quiet, just the way I liked it. There must be some activity happening on the lake as I noticed some lights movi...

Betrayal? Ch. 02

by homeforbreakfast on Sep 17, 2017
Loving Wives

I apologize to those who read the first story and did not get an ending. I thought I could tell it all in one story, but have since decided that I want to keep my options open. So here is part two, this one from Lynn's point of view. I appreciate any feedback. * I was on my way home from a wonderful night. Most people would consider my situation to be a v...

Girlfriend Taken by Bigger Cock

by maskrose on Sep 12, 2017
Exhibitionist & Voyeur

I barely know how to begin... It happened a year ago. My girlfriend Jennifer and I had just moved into a cheap apartment. We were both studying at the university, I was 26 and she was 24. She was the most beautiful girl I've ever seen. She had medium-short blonde hair, big brown eyes and a voluptuous body. She had perky c-cup breasts with small nipples and...

Expanding Horizons

by JacobGoody on Sep 16, 2017
Fetish

Adam was cute from the minute I laid eyes on him at a friends party. Skinny and bearded he was a plaid wearing hipster kid holding his beer and listening to friends tell ridiculous stories about art school. He kept a smile on his face, and whenever there was a pause to drink, his eyes scanned the room, sometimes making contact with mine. Eventually that eve...

After Hours Alicia Ch. 01

by NewAgeErotica on Sep 11, 2017
Group Sex

Alicia Reynolds was a rather transparent girl throughout high school. She didn't really belong to any of the cliques at her school. She wasn't pretty, perky, or rich enough to be considered a part of the "prep" clique. She wasn't into partying, doing drugs, or having unprotected sex, so she didn't fit in with the party crowd either. The nerds were more of he...

LOrd of VEgas Ch. 13

by PaulStevens on Sep 19, 2017
Sci-Fi & Fantasy

Edited by luvtaread * With the aid of Hephaestus Jill and Lloyd were able to re-enter Las Vegas. To further aid their attempt to get close to the Goddess they used their powers to alter their appearance. They hoped that by doing this they would be able to get close enough to execute the plan that Lloyd had come up with. It was not the best of plans but it...

Threesome, Anal Strap-On, & Angela

by LadyAnalLover on Sep 12, 2017
Anal

I had just began to really find myself sexually by my 3rd year of university. I had found out that I love anal sex, especially with myself and my ever growing set of toys. I had found out that I am a squirter and I learned complete control over the muscles that allow me to cum over and over on will. And while I had not had very many men in my life I had begu...

My Sensitive Breasts

by fantasyboy on Sep 11, 2017
Fetish

I was a slow developer as far as my breasts were concerned. All my friends at school seemed to have them months before me. But at last mine were beginning to form. I would inspect myself daily if not hourly. I was so keen for them to develop. This day I stood naked in front of the mirror in my bedroom admiring them. I lifted my hands to them and held them. I...