Sissy Doctor Stories

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AliExpress and Sissy Downfall Pt. 09

by His_fag_wife on Aug 20, 2018
Transsexuals & Crossdressers

Charlie stood wobbling slightly, on the 5 inch heels. Legs a little apart to accommodate the very substantial base of the Fenrir Dragon cock currently stretching her wide open, holding her buttocks apart and her asspussy wide open with the 2 1/2 inch diameter. She felt better now, shattered and tired but she was basking in the looks of approval from both her...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

The Awakening of a Sissy Pt. 05

by sissyjolie4u on Feb 3, 2020
Transgender & Crossdressers

There I was, on my knees, in very skimpy feminine undergarments, locked in a room in the back of an ABS, with 6 men and my Mistress. This was the start of what was to be the other portion of my punishment. Mistress walked toward me with that evil grin of hers. As she was approaching me, she said, "Jolie, these men are here to assist me with your punishment...

Relief

by Svenskaflicka on Aug 17, 2017
Exhibitionist & Voyeur

Appendicitis. A weird and difficult word. What it meant was that the reason why Ricardo's mother had been in such pain the past few days, the reason why she had walked bent over double, wincing with pain as she went about her business, the reason why she had collapsed at work and had to be taken to the hospital in a hurry, the reason why she had to have an o...

Mikey becomes Melodie Ch. 02

by tiffanyfoxe on Jul 14, 2020
Transgender & Crossdressers

I lay there under this incredibly beautiful fully transformed girly-boy, her lipstick covered lips still softly and tenderly kissing me, kissing my lipstick covered lips, my rouge covered cheeks, my eye shadow covered eyelids and my mascara coated lashes, showing how much she loved having me under her, her huge still hard cock buried deep inside my pussy/bot...

The Visitor Ch. 06

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

The shower when it came on surprised me, he had the shower head in his hand and played the spray up and down over my body, I blinked, recoiling in my shock and looked up at him, the shower gel squirted at me. "I like a clean sissy" I just hated that alien electronic voice so much, but I knelt there in front of him only too glad to be rid of the smell of hi...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Jamie's Descent Pt. 02

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

'That's it, baby,' Vanessa purred as she snaked her hips forwards and back, gently sliding the strapon in and out of my mouth. I could no longer think rationally, as any self control I still had slipped away and trance like, my eyes closed, I sucked the rubber phallus in and out of my lips. 'Baby, you love this don't you?' Vanessa's voice took on a hypnoti...

Coming Home, Coming Out Pt. 10

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This chapter marks the end of this series, which seems to have run its course. I am grateful to my readers who have commented on my story. As ever, I should remind them that this is a work of total fiction. All characters are at least 18 years of age, and everyone who participates in any of the sexual practices described does so consensually....

Making of a Porn Queen Ch. 03

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

Sunday morning I woke up with some one licking my ear. When I open my eyes I saw it was Tracy who was doing the licking. I smiled up at her then I saw the clock on the bedside said it was after ten. I jumped up and said as I tried to get out of bed, "I'm sorry Miss Tracy. I'll get your breakfast right away." Tracy pulled me back onto the bed and said, "I...