Sissy Transformation Stories

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Infinite Scroll

My First Time as Sara... Pt. 03

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I've been with Steve for a couple of months and to say I've been happier than at any time in my life would be a gross understatement. Being with Steve has been an awakening. I'm no longer afraid of life. I was shy and timid as John. I didn't make decisions. I didn't take the lead in anything and was easily bullied. My ex fiancé was the worse bully. As Sara...

Panty Fantasy-Hurricane Kate Ch. 01

by eliasrotica3 on Sep 14, 2017
Fetish

'A day like any other,' thought Kyle to himself. The view outside his Research Triangle Park office was a little boring with the leaves all fallen and the snow not yet come. It felt good anyway to see the world and the weather. Kept him from getting office fatigue. He liked his job as a senior accountant but he did get a little bored by the routine at times...

Mistress and Master

by davemacc65 on Sep 16, 2017
Transsexuals & Crossdressers

I had been to Mistress Elaine's and Master Johns several times but today's visit was different. Mistress Elaine had buzzed me in the gate but it was James their butler who waited for me at the door. I had not met the staff of the house properly but I had heard them moving around and cleaning. I had wondered if Mistress had more slaves but the people I had br...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

The (un)Pleasant Rise to Power

by Cynthia Sissy on Oct 10, 2019
Transsexual

"There it is, at long last!" I exclaim, as my eyes set sight on a lone statue in the centre of the chamber. It was surprisingly well lit by the rays of light seeping in from cracks in the ceiling. I scan the area for any obvious traps, and after considering the month long journey it took to get here from the capital it seems like dying at the foot...

Open in Reader

The Inner Slut Ch. 07

by sub2femdom on Aug 22, 2018
Fetish

Chapter 7 - Lexi's Training Two weeks have passed. Amy is proud of Lexi's progress. They've spent about two hours each night practicing makeup, walking in heels, poses, and attire. Lexi even acts more feminine, especially when Mike is around. More than once, Amy has noticed Lexi staring at Mike, specifically at Mike's cock when it shows through his shorts...

Covid 19 - Pete Turned into Charleigh Pt. 03

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes." Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certa...

Dear Karen Pt. 02

by Da_Vida on Sep 16, 2017
Transsexuals & Crossdressers

02.20.09 Dear Karen, We have come a long way in a few weeks. A few days into our new arrangement I went into the bathroom and BJ was standing in front of the commode taking a leak. I told him I wanted him to stop, which he did as he gave me an incredulous look. I told him to put the seat down and to sit. After he was sitting, I told him to pee his heart ou...

Such a Deal Ch. 02

by Angelscuck on Sep 13, 2017
Fetish

Her request made my cock hard. I couldn't have fantasized a better situation. I ordered the Lobster, she had the Prime Rib. I watched her skillfully dissect the meat and devour it like a female lioness eating a gazelle. She was magnificent! We made small talk throughout the meal, never alluding to the proposition we had just discussed. We were on an equa...

My First Time as Sara... Pt. 02

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I look up at Steve and give him a genuine smile. A smile that tells him I want and crave him. In a whirlwind day that started with me buying some girly stuff to enjoy on my day off from work, is now ending with another mans cock in my lipstick covered mouth. I have his legs open and I'm on my knees. My hands are now running over his muscular and tight leg...