Sissy First Time Stories

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A Little Twist Over the Road

by mdw_dark_angel on Sep 17, 2017
BDSM

Master is an OTR driver for a national corporation. That could make things very difficult for O/our relationship as W/we would not be able to see Him very often, for very long at a time, except that - sissy, affectionately known as pet, and angel, referring to this girl - are His relief drivers. W/we travel with Him everywhere so it makes life a bit more exc...

The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

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 Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Growing Pains

by Spoox on Feb 8, 2020
Romance

Tip: This is a slow burner loosely based on my experiences. If you want something to wank off to, skip to the chapter First Date and the options that lead off from there. Don woke to the electronic buzz from his alarm. He rolled onto his side and reached for the snooze button. On pressing it, he heard the familiar pitter-patter of feet on the stairs. "G...

Isabella's Reversion Pt. 05

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Jack's Bully Ch. 01

by Alpacawreck on May 22, 2018
Fetish

*Everyone in this story is at least 18 or older* ***** Jack couldn't wait for the bell ring so he could go home and masturbate. He hit snooze too many times this morning so he didn't have time to rub one out before walking to school and his cock had been aching all day. To make matters worse it seemed like every girl had worn leggings that day and while it...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 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...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

Kym's Day of Reckoning

by Dirt Man on Sep 19, 2017
BDSM

The flat looked pretty much the same as the other residents on the street. Aged in the special care all English tenement houses have acquired since the last world war. However I wasn't so much interested in the landscape, or the architecture as I was the young married Goddess who had at last answered the door. "Mrs. Adams?" I inquired. "Yes?" Her voice an...