Sissy Gangbang Stories

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Favorable Odds

by Fiend21 on Apr 11, 2017
Amateur

Watching your parents' SUV drive off down the road, you're left standing in front of the massive red brick building that serves as the Clear Water Institute's main center. You glance around, seeing a shining blue lake that you assume has given the campus its name, a large metal building you assume is a sports hall and two large dormitory buildings. You grima...

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Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Mary Becomes a Whore

by Juggerhead on Jul 30, 2019
Transgender & Crossdressers

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went o...

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

Gothic Sissy Gets Gangbanged by BBC

by Satanicsissybitch on Apr 17, 2019
Transgender & Crossdressers

I'm really a pretty normal girl for the most part. Normal in the sense that I'm not unlike most people. I love music, albeit heavy metal, I love clothes and shopping, although most of my wardrobe is made up entirely of black dresses, band shirts, fishnets and cute thigh highs. I love to read and write, I love hanging out with friends and going out to concert...

Ugly Duckling to Sissy Princess Ch. 06

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

I was terrified, yet part of me was aroused to have such beautiful girl and gurl touching my body. It felt as if they were preparing my body for a sacrifice. Vanessa and Bernice seemed to want to sync their attacks. I could feel the tip of Vanessa's cock at my back door and the tip of Bernice's strap-on cock on my lips. I looked straight into Bernice's eye...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Abducted and Turned Out Ch. 03

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

...... So, he walked up and positioned himself at my cum soaked pussy and penetrated me, and as he did I couldn't help but moan and encourage him by saying, "Fuck my pussy". As he was pounding me relentlessly for the next few minutes, he began to tell me about himself. "I noticed you the day you moved in. I knew you were a slutty little sissy then, and I k...

The Journey Pt. 01

by MissYellowPanties on Sep 13, 2017
Transsexuals & Crossdressers

Part 1 The Journey. I sat in the back seat of the car, my legs stretched in front of me and crossed at the ankles, the short skirt I wore barley covered my panties, and I could feel the cool leather of the seat press against my legs. I smiled at the reflection of the drivers hungry eyes in the rear view mirror, longing, lust, and power, mixed together in...

Beauty and the Bully

by xaitonnar22 on Sep 13, 2017
Transsexuals & Crossdressers

The sun was high in the sky, yet a cool breeze blew over the busy metropolitan city of Kingston, California. The students at the local high school, Kingston High, were outside enjoying their half hour of lunch under the warmth of the sun high overhead. Jason Lane darted nervously between the buildings on his way to his next class. Most of the other student...