Sissy Bet Stories

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Ms. Alexandria - Interview No. 02 Pt. 01

by gasissynora on Nov 4, 2019
Transgender & Crossdressers

This is the second part of the Ms. Alexandria series. I believe it will stand alone, but will make more sense if you read the first part of the story, "Ms. Alexandria: The Interview." * Ms. Alexandria: The Second Interview -- A day out. Part 1 I get home from the interview, feeling that it went very well. I am also extremely horny so I strip down to my li...

On Line and Linda

by vinceh23 on Sep 16, 2017
Romance

Linda and I had met through one of those ubiquitous on line dating sites. When I saw her photo it grabbed my attention. We all have certain characteristics in face shape, eyes, kips, those things we can't necessarily define but when we see them we know immediately that we like that face. And she was tall, 5'9", and though not slender she was not overweight....

Sissy Hubby

by rj1774 on Mar 18, 2020
Fetish

In case these are not the fetishes you like; this story features pegging, CEI, and sissy training. * It had been a very long week at work, but I had finally made it to Friday at 3pm and was excited to relax over the weekend. Then a text from my wife of five years came in that started the snowball rolling down a steep mountainside. "Hi! I have to run a few...

The 19th Hole

by skywayscribe on Sep 12, 2017
Group Sex

Sissy and Michelle were having lunch downtown Minneapolis when Michelle starting asking Sissy how Chuck was at fucking .... Sissy got wet then and there and told Michelle, "If you only knew...." Who knew that would be the beginning of a fabulous experience for Chuck ... and Michelle ... and Sissy. Michelle and Sissy continued their afternoon downtown girls...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

Becoming Mindy Ch. 02

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Thank you for the positive feedback from my first story. As I recall things I wrote about in my diary, I am not going to be writing on all of them. Just the ones that are important to my story and/or just some memorable events (i.e. the first time I..). I hope I am able to write them in a way that you find as enjoyable reading as I had living them. I have se...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

Mistress Chronicles Ch. 02

by MistressMtoyou on Sep 25, 2017
Fetish

2 – Hurry Background/update In my last story, my new subject Muffin and I had our first live session. He is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professes to be most interested in being gradually transformed into a sissy maid and forced to serve in variou...

Neighbourhood Terror to Sissy Pt. 16

by Fibaro on Jan 6, 2020
Transgender & Crossdressers

Chapter 18 Marcy had hoped the stop at CC's would have been the last one. She had suffered enough embarrassment for a day. Lisa's claim that they still had a few errands to run made her worry that it wasn't all over after all. Her worries were soon confirmed when they stopped in a rather seedy looking neighbourhood. Getting out of the car Marcy knew better...

The Dragon Ring Ch. 03

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Three Fool me once shame on me, fool you twice...? I awoke in the early dawn. The sun yet to broach the horizon, but casting its rosy glow high into the cloud speckled sky. Sissy was lying across me; her head nestled into my shoulder, her arm curled around my neck, her hips across mine and her foot wedged twixt my knees. I reached over and smoothed her...