Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Getting Help Ch. 01

by azkelkel on Sep 16, 2017
Transsexuals & Crossdressers

I nervously sat in the waiting room for my 1:00 p.m. appointment with the therapist/psychologist. I found her through online searches, as I guess we do all things nowadays, where her credentials and location were most important to me. She received her various degrees from decent universities and chose to open up her practice in an area just far enough away f...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

A Sissy Saga Ch. 12

by Snurge on Sep 15, 2017
Novels and Novellas

Poppy returned to the dormitory much earlier than had been planned. Most of the students at the Grange were in special detention and occupied in doing things in preparation for Open Day, but he was no longer a proper pupil and for a while that afternoon he was a free agent. He was feeling active and restless, but he arrived to find the room occupied by the...

Cucky Trained by CD DOM Pt. 03

by sndycd on Sep 15, 2017
Transsexuals & Crossdressers

"Gather your things, it's time to go." "Yes mistress." You got yourself together but I told you not to clean the cum off your face so you walked out of the theater and out of the store looking like the cum soaked whore you are. As we walked out I said, to no one in particular, "I hope you all enjoyed my whore. She'll be back." Another two block walk bac...

A Phone Call

by trixie_leigh on Sep 2, 2017
Fetish

--Welcome to Mistress Wanda's World of S and M. THE home for ALL your most sick and twisted fantasies. Feel the sting of her whip. Hear the crack of her lash. Unleash your most INTIMATE desires. --If you're over 18 and have a credit card, enter the number now. --First time callers— [XXXX YYYYYY ZZZZ] --(laughter) --Very good ... Slllaavvvvvve. --Now, l...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...