Sissy College Stories

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Six Months

by JamesMiehoff on Dec 10, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Attack of the Yellow Convertible

by 4glory6 on Sep 1, 2017
Group Sex

Gail nudged Sam's body off her stomach and to the side. He was lost to the world. She had about ten minutes she figured before he started to snore and she'd be forced to get up and go to the guest room. The mention of "guest room" got her off on the cryptic e-mail message she'd gotten from her cousin, Faye, earlier in the day: "Landed in PBurg. Docking soon...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Summer, My Sister's Best Friend

by SusanJillParker on Sep 12, 2017
Romance

This is a Summer Lovin' contest story. Please vote. * Stephen's love of his life is his sister's best friend, Summer, a woman eight years older than him. Summer, I'm in love with Summer, my sister Christine's best friend and I don't know what to do about it. Love at first sight, it all started the first time I saw Summer in the summer of 1968. She was in...

Sissy's First Time

by Sonjas_pet on May 23, 2018
First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoi...

Sissy Training Week 01: Induction

by Peggylea on Mar 17, 2020
First Time

Some years ago I was under the supervision of a Domme Mistress called Neve who organised for me to undertake a course in sissy training so I fully understood my role as a smalldick submissive. She found me a place on a 6 week sissy training course with a teacher called Mr Deal who was very experienced and had devised such a program. I was to meet Mr Deal a...

Sissy Training Week 02: Obedience

by Peggylea on Mar 17, 2020
First Time

Week 2 Obedience I arrived at Mr Deal's my Master for the second week of the sissy course. Nervously I knocked on the backdoor to be greeted again by Mistress Rhea. She took my coat and led me straight to the changing room where I stripped naked as last week. Mistress R led me into the kitchen area and told to wait for my Master. Then assistant Toby came...

My Girlfriend's Sissy Roommate Ch. 04

by SEVERUSMAX on Nov 21, 2017
First Time

"So, you softened up faster than I expected on the issues of fellatio and vaginal sex, babe. Not that I mind, as it's between you and Rain, and I think that it's rather sexy, anyway, but what prompted that? Just the knowledge that Rain has meekly accepted his lot and will be a loyal husband to you? I wouldn't go so far as to call him a cuckold in the typical...

Teacher Wife Goes Black

by easyballs on Nov 25, 2017
First Time

This story is about a married wife who makes her small dick husband a sissy slave, and eventually finds some real cock to fill what she has been missing but it comes from an unexpected source. If this type of story offends you fuck off and read the beano or something negativity I get daily, so it won't be new to me. ***** As I sit here writing this I am na...

Sissy Boy Secretary Ch. 09

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he...