Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Sabrina Pt. 02

by GeneraZ on Mar 25, 2019
Sci-Fi & Fantasy

Chapter 6 As Paul and Sabrina spent time together the time flew by, and seemingly in the blink of an eye a semester had passed. Though the demands and distraction of his incredible girlfriend had done considerable damage to his grades Paul had never been happier. Nevertheless, he worried what he'd tell his parents when they'd ask and learn how badly he'd be...

My New Neighbours Ch. 04

by csm1967 on May 6, 2019
Transgender & Crossdressers

We must have drifted off as I woke with a start and it took me a moment to realise where I was. We were still in the bedroom and I was cold from the air conditioner. I continued to lay there as Katie was asleep on my chest. I looked at her and smiled and once again was thankful that I had a partner that allowed me to fulfil my sexual fantasies. However, the...

Cassandra Ch. 01

by AngelCherysse on Oct 13, 2020
Transgender & Crossdressers

Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these are her stock-in-trade. Cassandra flaunts her outrageous bod...

It Was Just Sex, Honey Ch. 01

by Night Scribe on Sep 19, 2017
Loving Wives

I guess you might say I'm a lucky man. My name is Paul, and I have a runner's body which has stayed with me since college. That's how I got to college in the first place. I was good at running the hurdles and even better at the sprint races. If it was a mile or less, I was your man. At least I was good enough to get an athletic scholarship. I even got to try...

TV Blowjob Slut for Blacks Ch. 03

by barbielovesbjs on Sep 11, 2017
Transsexuals & Crossdressers

The man sitting next to me driving is Darnell. He's a total black playah who owns a black bar near my house. He has his arm around my neck in a triumph of ownership. Basically I'm trapped in his black Lincoln Navigator, forced to listen to his gangsta rap and he's got a good buzz going. He's really happy because I'm wearing every piece of a little sexy outfi...

Sissy Hubby Ch. 06

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

As I stood under the showerhead, the hot water pouring over my body, I could think of nothing except Ben's cock sliding in and out of my throat. My freshly pierced "clitty" tingled with excitement and became semi hard. I stepped out from the shower before I started stroking it, quickly drying my body with a clean, fluffy towel, taking extra care around my be...

A Wife's Lover, His Boss Ch. 02

by keptsissy on Aug 30, 2017
Fetish

"I take it she's spoken with you about me, about me and her?" He sits behind his desk and stares at me. He's aloof. He's never said more than two words to me before, passing in the hall at best. I'm so nervous I can hardly speak. When we got invited to his all-company BBQ party at his house it was the first time he'd ever really paid any attention to me. Mo...

Summer Hire Ch. 17

by brentaden on Sep 15, 2017
BDSM

Dinner Date Melissa stared at the door, feeling very uneasy about her motivations. She had endlessly dithered about how to dress for her dinner "get-together" with Deborah in the city. When Melissa had called Deborah the previous day to ask about getting meeting for dinner on one of her days off, they had wound up chatting for over an hour, as though they...

Temptation Ch. 11

by Ada Stuart on Sep 19, 2017
Erotic Couplings

Jeff called her a few days later. "Hey, Amy, how are things going?" "Not too bad," she answered and stared at her messy house and at her computer that was filled with sexual fantasies about Nick. She hadn't been able to do anything besides writing lately and she felt like a complete mess. "So is Nick around or are you two still busy wearing out the bed sp...

Oops, I Did It With Britney Pt. 02

by britneyfan on Sep 14, 2017
Celebrities & Fan Fiction

3. I'm Not a Girl, Not Yet a Woman As you can imagine, the sight came as quite a shock to me. My eyes practically popped out of their sockets and my mouth dropped open at the sight before me. Britney Spears, America's sweetheart, the world's sexiest superstar, the woman I had spent the last five years lusting after, was no woman at all. Sure, she had those...