Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

Sissy College Ch. 01

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

All characters 18 and above. This series will eventually be filled with all the raunch you desire, but I like a little foreplay first. So sit down, slip down your panties, and enjoy! I love your comments! Chapter 1: Mathematics Welcome to Chester College: An exclusive all-boys Sixth Form College catering to talented young men from across the country aged...

Aunty's Toys Ch. 01

by novelcriss on Aug 21, 2018
Fetish

Simon rang the door bell, prompt at 2 pm, somewhere between nervous and excited and wondered quite how he had reached this point. He had met Sally in, of all places, a crowded cafe at King's Cross when all the trains were late. She'd pulled up a stool next to him , asked if it was okay to sit and started chatting. She was so easy to talk to, middle aged, n...

Controlling Sissy Janice Pt. 02

by sissy_janice on Jul 6, 2020
Fetish

Lilly instructed me to go upstairs and strip, and to remove my wig. "I have to get some bags out of my car. I want you naked and in the shower when I come back." I did as I was told. I was in a bit of a fog. I was now going beyond what I'd ever contemplated. Even if I'd worked up the courage to tell Lilly the truth, the most I'd have hoped for was the occas...

Such a Deal Ch. 04

by Angelscuck on Aug 31, 2017
Fetish

Sasha had me strip down while she cleaned me up. I was then told to put on a shorty nightgown. I was then taken to a bedroom and allowed to rest. I was exhausted. We had been at it for seven hours. I was awoken at mid-night by Sasha and dressed as before with fresh makeup applied to my face and hair re-arranged. "We have company and you are the entertai...

Sissy Life Pt. 04a

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

That's it then. I am going to be whipped by my wife's - my Mistress' - lover. I had offered him use of my mouth in a vain attempt to stave of the beating to come, but as he said, why would he be interested in my mouth? He has my wife's whenever he wants. He has no interest in sissies, this isn't his fantasy - he's a man. A real man. 'I said get over here a...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Sissy Jessica Kinky Office Shagging Ch. 02

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi again this is Sissy Jessica Howells , the kinky 0lchfa schoolgirl with an excited cock inside her navy, blue panties. At this moment my cock is inside Georgina Harris's mouth. Georgina, my 23 year old ginger girlfriend, has her head between my legs, giving me a fantastic blow job. Just feeling her long, red hair against my balls, gives me a weird sensatio...

Discovering Amber Ch. 07

by Ms_Allison on Mar 25, 2019
Transgender & Crossdressers

Mistress notes: The morning after is always fun, people tend to get caught up in the moment, sissies included, and amber was no exception. The fact Jenn and I were there to remind her of all of it just made it better! The fact amber seemed to really enjoy humiliation only added to the whole experience. Ms. Allison ~~~~~~~~~~~~~~~~~~~~~~~~~~ The following...

Tales of Seth and Travis Pt. 01

by pantywriter on Sep 16, 2017
Transsexuals & Crossdressers

The early June morning dawned misty but cloudless; it was forecasted to be one of those absolutely perfect late spring days with dry air, sunny skies and temperatures in the seventies. Nothing could be better. Whether it was the weather, or just his state of mind, but Seth woke in a wonderful mood. He sang quietly to himself as he made his bed, tidied up h...