Anal Sissy Stories

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Jack and Jill Pt. 05: Thailand

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab...

Fukee Sukee Beach

by JamesMiehoff on Nov 19, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Tom and Friends Adventures

by Mobman1 on Oct 25, 2020
Exhibitionist & Voyeur

In the night of Falmon, we come to see over the house of the young characters of the Story.What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy) What's next? Lisa Emma Sori Paige Tom (sissy) Ethan (sissy)...

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Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

Caught in Panties & Dominated Ch. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Rick's big hard cock, ramming in and out of my sweet mouth. Past my tonsils and into the back of my throat. My heavy breasts bouncing inside my tight blouse, my stiff nipples poking straight out. On my knees, in my tight skirt, toeing my high heels into the floor behind me. And my dick getting harder and harder and harder in my panties. I could feel my precu...

A Sissy Surprise

by nancyallen on Sep 16, 2017
Transsexuals & Crossdressers

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into the bedroom and stopped dead in my tracks. My boyfriend was on...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...

Suddenly Sarah, A Different Tale

by grizzley123 on Sep 14, 2020
Fetish

Suddenly Sarah, A Different Tale ************************** This is an alternative Chapter 2 to the Suddenly Sarah story I wrote recently. It takes day number two with Sarah in a whole different direction. It likely helps to read the first story. The themes of this story are not for everyone, but for those that like submission I hope you enjoy. As always,...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...