Sissy Bareback Trainer Story Stories

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The Awakening of a Sissy Pt. 07

by sissyjolie4u on Mar 9, 2020
Transgender & Crossdressers

I was a giddy as a school girl knowing that I would be sleeping with Tim, Curiosity was building inside me. I was going to sleep with a man for the very first time. What was the special surprise that Tim had planned for me. All night long, as we watched sissy porn, Mistress kept harassing my pussy with various levels of my trainer. I was happily enjoying us...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...

The Awakening of a Sissy Pt. 05

by sissyjolie4u on Feb 3, 2020
Transgender & Crossdressers

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers. As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

Another Weird but Satisfying Dream

by MrJimJim on Jan 22, 2019
BDSM

This story is not true. I just felt the need to get another recurring dream down in words to share with you. I hope you enjoy it! -- It was late. I was tired. I'd had one of those work days that makes you want to scream FUCK YOU to the entire world. I walk in the front door, set my keys on the table, and walk into the kitchen for some water. I go to the...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...