Sissy Chastity Gangbang Stories

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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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Cuckolding Sindy Ch. 02

by SindySuxALot on Sep 13, 2017
BDSM

Sindy listened intently over the intercom as Lucy was in the other room with her dates. The moans and groans were constant as her Mistress orgasmed repeatedly. It always turned Sindy on immensely to hear her Mistress with other lovers. She sat in front of the computer with her largest vibrating plug inserted in her ass and watched the sissy on the computer m...

Candi is a Sissy Cam Girl Ch. 01

by CandiCumminz on Jan 15, 2019
Transgender & Crossdressers

This is the 6'th story in Candi's tale. Please read the Candi's conversion series and Candi Gets an Upgrade for the full picture of what's happened so far. - Hi! My name is Candi Cumminz and I'm your new favourite bimbo sex-doll. My camera's always on and I'm always horny so stop by any time for a good time! I love dressing up for my fans and putting o...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

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...

A Sissy's Forced Gangbang Pt. 03

by sissy77 on Jan 12, 2018
Transsexuals & Crossdressers

This is the final part of the 'A Sissy's Forced Gangbang' series. I received a lot of positive feedback for the first and second parts and I am very grateful for the same. As for those who requested the next set of events, I would like to apologize for the delay in writing this piece as I was preoccupied with a few other things including a few sissy encounte...

A Sissy's Forced Gangbang Pt. 02

by sissy77 on Dec 8, 2017
Transsexuals & Crossdressers

This story is a continuation of the part one of the series under the same title. If you haven't read part 1 already, I highly recommend you do so before reading this part. ***** After snapping out of harsh daddy's words and contemplating what more humiliation was planned out for me, I lifted my head off the bed and was welcomed to the sight of big daddy's...

Marabogo: Cuckold Island Ch. 03

by eeric on Jan 21, 2019
Interracial Love

A crowded lobby stood in front of Joshua as he began to drag the suitcases towards the elevators. Luckily two of the cases had small wheels on them, which made it a lot easier. Though the laughter he got from the women he passed made the whole matter a lot more humiliating. Joshua could hardly fathom how this had all happened. Just a few days ago he had go...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...