Sissy Deepthroat Stories

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The Adventures of Sissy Madison Ch. 02

by sissymadison on Mar 6, 2018
Transsexuals & Crossdressers

They all got into Kim's car ready for the trip. Haley turned around as soon as Kim started the engine looking Madison up and down. "You are just sooo cute, I can't even get over it!" and with that Haley got out and hopped into the back seat with Madison. "So do you like being all dressed up like this?" Kent nodded but didn't say a word. "Oh don't be l...

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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Trapped and Trained Ch. 02

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stocki...

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...

Mark Ch. 01

by evangelick_my_balls on Dec 12, 2018
NonHuman

1 The beginning of the gospel of Jesus Cum, the Son of Godcock; 2 As it is written in the pornos, Behold, I send my messenger before thy face, his cock hard and throbbing, which shall prepare thy anal way before thee. 3 The voice of one crying out in ecstasy in the wilderness, Prepare ye the way of the Lord, make his paths straight and his dick hard. 4 Jo...

Jezebel's Magic: Becoming Josephina

by twiddershins on Aug 31, 2017
Fetish

Jeff was just a regular dude when he met Jezebel. They had lived together for a few months and at first they seemed satisfied with each other. They got along fine and would have appeared like any normal couple in public, but that was now long ago. Even then, Jeff had felt lucky to have her because of his tiny penis! One Saturday night, Jezebel came home lat...

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

Neighbourhood Terror to Sissy Pt. 19

by Fibaro on Apr 13, 2020
Transgender & Crossdressers

Chapter 21 John had been looking forward to this very moment that he wasn't about to just get it over with. He was going to savour it as much as he possibly could. These contacts proved to be such a good find. They allowed him to stay anonymous as long as he didn't give away his voice while still not covering the sissy's face. A face even John had to admi...