Sissy Spanked By Alpha Male Stories

340,027 results
Orientation
Length
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Infinite Scroll

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

It’s actually called Huntington Island. And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries. I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private re...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Slutty Blonde Girlfriend Cheats

by mastersofwar3 on May 30, 2018
Loving Wives

Larsen was a tall hot blonde Junior at college. She had long wavy blonde hair and a big round ass, she looked like a model. Her ass was perfect, she was on elf the hottest girls in the school. She dated a guy named Zach for a couple years too. One weekend night she was over at her neighbors house, Hayden who was a senior. She was with Hayden, her brother Con...

Topped from the Bottom Ch. 05

by cutebabysadie on Sep 14, 2017
Fetish

Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be more specific in just 10 minutes she would be orgasming and screaming Mark's name. It ends with Todd humiliated on his kne...

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Cosplay Wife, Cuckold Life

by SatinSlip on Dec 3, 2017
Exhibitionist & Voyeur

My wife and I were high school sweethearts. Kimberly was a brilliant, lovely girl. With big breasts and long curly red hair. Academic and popular. I was nerdy, and smart. A bit to feminine to be handsome. I was shy and weak. Neither of us had been with other partners and our sex life was pretty vanilla going into our mid twenties. Mostly missionary style...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

The Galactic Gynarchy - John

by gynarchite on Nov 24, 2017
BDSM

Kidnapped by the Galactic Gynarchy - John's story John awoke with a pounding headache. Gradually regaining his senses, he realised he was not lying flat but on a slab at a forty-five degree angle. He tried to move his legs and arms to get off the slab, only to find them locked in place. Able to move his head, he looked down at his body. Naked! He was nake...

Katie and Rex Ch. 01

by EmeraldSolitaire on Aug 24, 2020
BDSM

Katie DuMont is a beautiful, passionate, and intelligent woman. She has always considered herself an alpha female and a committed feminist from the early age she could see how patriarchy and the way it promoted false so-called "traditional gender roles" has caused so much harm and the most for the men who found themselves the losers of life, especially amon...