Sissy Story Gangbang Stories

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Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

After The GangBang

by Angelscuck on Sep 17, 2017
Loving Wives

I woke up about 8am. I was sore all over. My ass hurt and burned like hell and my jaw ached. Then it all came back to me. Angel's gangbang. Or should I say Angel and my gangbang. Sure, she was fucked in the ass, mouth and cunt by over twenty guys, but I took my share of cocks too. I was caked all over with dried cum. I felt her stir next to me. She was a...

Introduced to Black Dick

by Phantom8JMF on Sep 16, 2017
Transsexuals & Crossdressers

This is a story that is one of many in which it is time for me to share. In a nutshell, my name is Dean, my mother had a thing for Dean Martin it seems, but I go by Dina. I am a 26 year old white pre-op transsexual that has no interest in switching my outside in, if you know what I mean. I was born to a single mother, never knowing who my father was. Conside...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

My Wellhung (15"BBC) StepDad

by BibiBimbo on Apr 22, 2025

2 days after Bibi's 18th. birthday, the Sissys Mum brought her new NiggaMaster/Husbond-to-be with her home where Bibi was introduced to Rex, the WimpWuzz's next NiggaStepDad, who was 2m high, Wellbuild & Muschular weighing 125kg & Extremly Wellhung having 15" looong & 4½" thick Big Black NiggaCock.. He liked how the Bibi dressedUp as 'B...

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This is What I Want

by bisissystephenie on Jan 22, 2020
Fetish

My wife Pam has started going out for a "Girls Night Out" and this time she came back a little tipsy. And very late! She knows how I love to give oral sex to her and she hardly ever says "No". We went to the bedroom and she laid back on the bed. I got in my position, on my knees and between her legs. I started kissing her knees and going up. She stopped m...

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

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A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

Pleasing Angel

by Angelscuck on Sep 13, 2017
Erotic Couplings

It had been about two weeks since Angel's gangbang. Her sexual appetite seemed to have increased since that fateful night. I was kept very busy spending a lot of time sucking her sweet pussy nightly which I loved to do. She had multiple orgasms but never seemed to quite get enough. Due to my erection difficulties from the radiation treatment of my prostate...