Sissy Gym Stories

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From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...

Submitting to Dominance Ch. 02

by _pdy_ on Sep 28, 2020
Transgender & Crossdressers

This is chapter 2 in the Submitting to Dominance series where our heroine Perry has some alone time with the man who will take her for himself. I welcome all comments, criticisms, suggestions, and feedback, but in general I just write these stories for fun so please take that into consideration. Thanks and I hope you enjoy! --- The drive to Perry's was ex...

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

A Husband Named Cathy Ch. 02

by cathynylons on Sep 18, 2017
Transsexuals & Crossdressers

When Toni had finished inserting my butt plug she turned to me and said, "There, now you'll see how much more feminine you walk. We will be going out later this afternoon so I think now would be a good time for you to go to your room and think about your behavior yesterday." I went to my room and sat at the vanity and began applying my eyeliner, eye shadow...

A Sissy Saga Ch. 23

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Pardoe's heart pounded like steam-hammer as she made her way to her room. It had been such a long time since she'd had a young girl to herself, to take command of, to admire and to love, and she knew Mrs Amos's niece Lizzie was a real doll. On the way she passed the Joanna television-person ensconced with Gloria in the stair well of the third floor, bot...

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Miss Guided Pt. 05

by MissMarianne on May 6, 2019
Transgender & Crossdressers

We had a lovely dinner after which Donna walked us back to the new apartment. I decided to make us some coffee while Donna and Charlene had a conversation in the dining room. I could hear everything they were saying. "So, Charlene, Susan has told me that you have been a very bad girl. You were very naughty and need to be punished she said. I am very disa...

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...