Sissy Fucked Stories

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Orientation
Length
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Infinite Scroll

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

The Surprise

by MissJAS on Sep 28, 2020
Transgender & Crossdressers

We started on kink, two friends seeing who could take a conversation farther. Two grown people with vastly different pasts but a mutual understanding that sex and what felt good didn't really have to make sense to anyone but you and who you were with. Not that we agreed on everything, but we agreed that if you and your partner were both consenting adult part...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

Steph's Descent Ch. 09

by 62_goo on Aug 31, 2017
Fetish

Steph woke up and looked at the sleeping form next to her. Her first thought was of her husband, Phil. But a split second after that thought entered her head she realised that it was Amanda her girlfriend sleeping next to her. She thought about how much in love with Amanda she was and also of the situation she found herself in. It had started when she was f...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

Young Master Ch. 04

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"I can explain..." I was standing in a French Maid outfit, with a sissy's cum still dripping from my chin because as usual she missed a spot, and I had just been caught bent over a desk getting pounded from behind...all I needed to make it the perfect shit storm was for Dale to notice my cock was stick disturbingly hard in my panties for some mind boggling r...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...