Sissy Transformation Stories

14,811 results
Orientation
Length
Source
Infinite Scroll

Kiah The Black Goddess

by Samuelx on Sep 17, 2017
BDSM

What's up dear readers? My name is Kiah Halls and I'm a young Black woman living in the City of Atlanta, Georgia. After completing my bachelor's degree at Spelman College, I enrolled at Georgia State University for my MBA. When I'm not in class, or at work, I'm having wicked fun in the realm of BDSM. I've become a dominatrix, kind of, and I'm really enjoying...

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

Jenny and the Wedding Dress

by Gemsissy on Sep 13, 2017
Fetish

I parked my car on the side street as I'd done a dozen times now. I was very excited and my cock was hard in my sissy panties as I got out of the car. Grabbing my gym bag, I felt the weight of the breast forms I carried in it, excited to put them on soon. I'd waited several weeks since my last visit to save up a nice amount of mad money. I never got out of a...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

The Sexy Cuckold Couple Pt. 12

by cuckcpl4play on Sep 19, 2017
Fetish

AGAIN, cuckold story with humiliation and if this offends you, please don't read! While fiction, we have experienced ample aspects of this story and this lifestyle. ***** Part 12 Vegas The men hustled out of the limo and rushed up the stairs to get a seat in close proximity to my wife. Master ordered me to keep sucking the used condom and rather than allo...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

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...

Discovering Amber Ch. 05

by Ms_Allison on Dec 24, 2018
Transgender & Crossdressers

Mistress notes: To say both amber and Jenn were surprised when Jenn entered my condo would be an understatement. I had given Jenn "some" warning as to what she might find, but she was expecting me to be dressed up for her not amber. Poor amber had the biggest crush and attraction toward Jenn as well, it was hard not to though, Jenn is gorgeous! It was time...

Away with the Lads

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You're invited to Dublin, Ireland with 10 other lads from your village. It's planned as a weekend of copious quantities of drink (Guinness), fast food (beef burgers and chips) and cultural interest (Girls). You fly from Southampton and costs are kept to a minimum. Aiden, The only Irish born lad in the group fails to show – selfishly this is good news, as unl...