Sissy Pills Stories

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Unknown Waifish Model Ch. 01

by Couture on Sep 12, 2017
Transsexuals & Crossdressers

We lay curled up to one another in the hotel bed, Sandra and I. I looked forward to the day we'd no longer have to make do with hotel beds and the occasional foray to my apartment. Yes, one day soon, she would leave her bastard of a husband and move in with me. God, she was beautiful. Her blonde hair was mussed up, as she lay on the pillow. Her face had th...

Shruti and Vaibhav Own Me

by smileymanav on Sep 14, 2017
Loving Wives

Totally Humiliated My name is Manav, I am 22, and when my story starts I had been married to my beautiful strong-willed wife Shruti for just two months. She is 21, with long Raven hair, large firm breasts, round ass and gorgeous long legs. One evening Shruti was sitting on the bed, and I had just finished getting naked for a sex session with her. She looke...

Let The Festivities Begin!

by fantasywriter on Sep 16, 2017
Transsexuals & Crossdressers

My thanks to LaughingDad for editing my words. It was his first attempt here on the site and he did a wonderful job. Thank you again Sir. The voice at the other end of the phone brought a smile to my face. Very few knew my secret, it wasn't something that came up in polite conversation. Luckily one of those who did know favored a facet of the scene which...

Jenny Plays with the Big Girls Ch. 05

by Johnboy9 on Sep 12, 2017
Transsexuals & Crossdressers

Well, that was one fine mess we got our Jenny out of that last story, wasn't it? Whew! This story is a lot calmer and yet a promise of more to come. I again want to thank all supporters and interested ones who have urged me to continue this tale of our Jenny to see what will happen to her in the end of her journey through this unfortunate (?) web in which sh...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Wife Left Me so I Could be a Girl

by TammyPanty on Jul 10, 2018
Transsexuals & Crossdressers

I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with my mother until she unexpectedly passed away when I was 23 year...

Another Submissive Slut Ch. 08

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I had hurried home from the porn shop only to run into Derrick in the lobby of the building. Lucky for me his mother emerged from a hallway and he could only cast me evil looks. His mother however took the opportunity to lay into me about my behavior and image. I realized as I slunk away from the verbal abuse that the chain around my waist was probably visib...

To Be, or not To Be; Fucked

by JakeInalake on May 29, 2020
Fetish

Gabrielle was far from below the average highschool boy standards of excellence. For starters, he was way shorter than any boy he knew, he was a stout 4 foot eleven inches, making him even below or barley on par with women. He was very curvy and feminine growing up as well, attempting many sports like track or swim had only decreased his hope in attempting t...

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Halloween Pool Party Pt. 02

by sissymissyct on Sep 15, 2017
Fetish

Maddy Returns I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why do...

Eve Quest

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 1 My name is, or maybe we better make that was, Andy Moore. Until recently my personal identification was in the name of Jamie Jo Moore and everyone I knew called me Sissy. My parents died in an automobile accident when I was twenty-four years old leaving me an estate of around $3,000,000.00 and an eighteen percent interest in an insurance company...