Sissy Sex Stories

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Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

Pinky the Sissy Maid

by Pinkytoes66 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ;) This is part 2 of my current series. Part 1 was "Pinky's First Shopping Assignment". I've yet to decide on a title of the series and am open for ideas. Thank you. *********************** A few days after I completed...

The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

The Awakening of a Sissy Pt. 04

by sissyjolie4u on Jan 27, 2020
Transgender & Crossdressers

After a long evening of studying, practicing, and of course grooming myself, I woke to a message from Mistress. The message read; Sissy Jolie, douche your pussy, bath yourself, and be ready to meet. Make sure you douche and your trainer is inserted. I'll be over around 11 and I expect you to be in matching bra, panties and your heels. Also, ensure your cocks...

Sissy Chantel, New Reality Ch. 05

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, My Surprise. "Ohh, Ahhh...Wha...what." I say as I wake up and am lost with where I am and what is going on. "What the... What the Hell? Where am I and what is this? Huh, what the Hell? Why am I chained and padlocked around my waist?" I'm groggy and very confused as I look at the room, dimly lit with a single hanging light bulb, I'm on...