Sissy Wearing Her Rubber Bloomers Stories Stories

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Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Keith's Caught in a Costume

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

It was the giggling that began to pull Keith out of his head. Sitting in English class, halfway through the fall of his senior year of high school at St. Michael's Catholic, Keith couldn't find the energy or heart to care about Hester Prynne or her scarlet letter. So, he'd let himself drift off into fantasy. This fantasy - like many of his since the beginnin...

Keith's Caught in a Costume Pt. 03

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith's alarm went off and he silently reached out a hand and silenced it. He'd hardly been able to sleep at all, tossing and turning with worries about what school would be like today. It had been less than a day since his life had turned into a nightmare - his incredible teacher had caught him rubbing himself in a cheer uniform and then he'd had to buy pan...

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Keith's Caught in a Costume Pt. 02

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith steered his car into the parking lot of Northmark Mall and into a parking spot. Then, his hands returned, zombie-like, to the steering wheel, and he stared off into the distance. He couldn't believe what had happened. He'd got caught, rubbing his dick, dressed in a cheer-squad uniform, by the hottest teacher at his school. She'd humiliated him, made hi...

Susuruss Pt. 21-23

by Macjay on Aug 18, 2017
Fetish

At last the cab delivered them home and they staggered into the hallway with considerably more luggage than they'd left with. Kate was very tired but David who had slept for about 5 hours was feeling OK. So he told Kate to take a shower while he began the unpacking. As he was about to carry the last of the suitcases upstairs the doorbell rang and it was thei...

Masculinity Lost

by GoldenCone on Apr 22, 2025

One strange day in the midst of the 20th century, a pink star lit up the night sky. From then on, the out-and-out Man has been a fading breed. The star's so-called 'gender-rays' disrupted the natural sex and sexuality of the human race, and some generations on the terms 'man' and 'male' are practically gone from the English language. Nowadays, young boys gro...

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In Search of Tamar Ch. 8

by miskeivitch on Aug 30, 2017
Erotic Couplings

I sat in the hotel lobby room waiting for Tamar. I whiled away the time with the current edition of the Jerusalem Post and numerous cups of Israeli kafeh botz. The cut and thrust of Israeli politics was interesting enough but what I really wanted were the latest CFL football scores. That day in Israel, the sports pages consisted of third-rate soccer teams fr...