Sissy Trap Stories

19,529 results
Orientation
Length
Source
Infinite Scroll

The Bearing

by SecondCircle on Aug 29, 2017
Erotic Horror

This is an entry for the 2013 Halloween Contest. Be sure to place your vote and check out other entries. Thanks. **** "It's that offensive line, man," Gary said. "You can't do anything with a line that's in shambles." I took a drink of my beer and nodded. "I wish they would've spent some money on that instead of those puny running backs and receivers t...

Not Drunk - Plastered

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

I was to marry on Saturday week and didn't want a stag night. The very idea of getting blindingly drunk with a loud, raucous bunch of mates unpalatable. I told my best man it wasn't required and to say nothing to my fiancé, Lily. Over the years I made many girlfriends and still secretly saw them on a platonic basis. I preferred their company to guys. One ni...

Red Wine On Her Yellow Dress

by Winterfrog on Sep 17, 2017
Loving Wives

Many thanks to snowbear for the editing of this story. * ROBIN'S STORY It was a bad day. It really was a very bad day for me, indeed. I had lost my job and I had lost my apartment. Though none of these matters were my fault, they happened with the worst possible timing. Only one week ago my girlfriend of one and a half years and I had agreed that we wer...

Daddies New Girlfriend Ch. 02

by LilLindaMelons on Oct 8, 2019
Transgender & Crossdressers

Part 2 AKA A walk in the park After the torrid love making session he had enjoyed with his Father just over a week ago, Jerry knew his life would never be the same. That night Doug had tenderly held his special Gurl against his chest and had warned his son that if he ever caught him dressed up as Cynthia again he would not be able to control himself becau...

Guarded Ep. 03

by GCStargazer on Dec 23, 2019
NonHuman

Leo strode over to the check-in desk of the hotel lobby. He was still in his leather pants, his jacket open and plainly exposing his sculpted muscles for all to see. The front desk girl gave a polite bow to him not seeming the slightest bit surprised by the display. "Good evening Mr. Montone, your room is ready for you already. The penthouse suite on the top...

Decorating Her Dainties Ch. 03

by wordyone on Oct 3, 2018
Fetish

Back at work in the new year, I was missing Sophia's horny body. A sight for sore eyes amongst the chaotic views of site work. She turned up all overalls and paint rags one lunchtime at the end of the first week. I was mortified when she took her bag of used nylons away with her. I had missed her naughty little body and her cheeky ways but to have a little...

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...