Sissy Anal Training Stories

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Making Francesca Ch. 06

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

The next morning Justin woke Frank up, "Rise and shine sleepy head. Mistress Celia has decided that you can bathe yourself now since you've been such a good girl. Now let's get cracking." With that Justin reached down and unlocked the chain from Frank's ankle that was attached to the wall. He then clipped the leash on to Frank's collar and led him into the...

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Behavior Modification Institute Ch. 06

by NancyPan on Sep 12, 2017
Fetish

Ms. Panington screamed and pushed me from her lap. The arousal monitor alarm was blaring. Ms. Jensen leaped to her feet and ran to Ms. Panington's side. Upon seeing the mess, she shouted, "Naughty sissy! Didn't you hear the alarm?" I lay on the floor ashamed and humiliated. I had heard the alarm begin to sound, but I so much wanted to cum I had thrust my co...

Just Look at Me Now Ch. 04

by GFfan on Jul 15, 2020
Transgender & Crossdressers

Let's see... where was I at the end of chapter three? Oh yes: seated on a footrest wearing lingerie and my pink collar, with my eyes adjusting to the bright light now that my blindfold had been removed—and adjusting to the sight of Jude's strap-on in front of my face. "Have you ever given another guy head?" Jude asked. "No, never!" "How about getting a bl...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...