Sissy Bet Stories

70,272 results
Orientation
Length
Source
Infinite Scroll

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

Sexy

by SweetOblivion on Sep 16, 2017
Transsexuals & Crossdressers

"Hi sexy," he grinned impishly out at her, blinking his eyes to adjust them to the bright sun, as he opened the front door to greet her. "Is Dora...?" She began and then did a double take: "What do you look like, Marcus?" "Don't you love the ice blue?" Lindsey looked the young man up and down and, smiled, despite the initial shock. He was wearing a pale...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Luke's Field Trip

by LucyAnn51 on Sep 16, 2017
Transsexuals & Crossdressers

All characters in this story are over 18 years old. This is a work of fiction and any similarity to other works or real people is simply coincidental. Hope you enjoy, love you dolls! Xoxo ------------------------------------------------- Luke was a sissy. The kids at school called him mean names and threw things at him. They played keepaway with his book...

Something New Something Old Ch. 03

by dorian87890 on Sep 25, 2017
Fetish

Ted's life had been turned upside down in the last five weeks. He was currently on his hands and knees in the bed of his neighbors' Josh and Nancy. A pair of pink panties were at his ankles and he was wearing a matching pink bra. His cock dangled between his legs trapped in a cage. Nancy was behind him with a strap-on. She was fucking Ted mercilessly. Josh...

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

Lock Your Phone

by Iamasissy on Sep 15, 2017
Transsexuals & Crossdressers

I am a sissy and I love it like most sissies I dream about belonging to a man to be owned by him. I fantasize about being outed and being forced to become a transsexual. I put out adds on craigslist NY looking for a Master. I take lots of pictures dressed, I take videos dressed saying my name is Karen I am a sissy and I want to become a transsexual for a rea...