Sissy Pills Stories

15,811 results
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Length
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Infinite Scroll

Brianna's First Day as a Daughter

by Sissy_Sammi_ on Jan 7, 2018
Transsexuals & Crossdressers

*All characters are 18+ years of age. ***** Brianna started her new life the following day. She tried to straight-face her way through school, hard to do with her new plug and cage, but she managed it. She didn't run home after school this time, though, as she found it a little uncomfortable to run with the plug in. She walked briskly back home and up her...

Cockland Island Pt. 03

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I think my dreams that night were pleasant. I was kind of still just transforming back then. But when I woke up, I remember the feeling of my butt plug in my ass was pleasing and that my caged cock was perfectly sissy cute and I was good with that. It was kinda a trip to look in the mirror and see it all. And walking with the plug, sitting with the plug....

It's a Wonderful New Life

by alexyzia on Sep 16, 2017
Transsexuals & Crossdressers

I met Sherry at a bar. Imagine that. I often picked up women at bars. I'm a good looking man, have a nice sporty car, cash flows freely from my pockets - at the bar anyway. So I do OK at snagging a tipsy babe for a nights folly. But all of the sudden karma has caught up with me. When I hit on her she told me to back off or I'd be sorry. When I persisted, pol...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

His Breeding Cow

by SWGirl on Sep 12, 2017
Interracial Love

(DISCLAIMER: If you're not a fan of interracial sissy cuckolding, go no further. Don't bother with the righteous indignation or the crude comments. Celebrate why you're here in the first place and move on.) "He said he wants me off the pill, he's going to breed me Tony!" "What!" I said. "Jenna, he can't do that.... You can't do that. You're my wife." I w...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Wife Humiliates, Hubby's Turned On Ch. 02

by Quietoldie on Mar 17, 2020
Transgender & Crossdressers

Bernie (formerly Bernard) That night after Carol had told me she was going to look for another man to inseminate her Carol took me by the hand to our bedroom and dressed me in the loose bra and panties along with the nightie she normally wears to sleep in. "You can wear them from now on sweetie, I've decided to sleep naked in future. You don't mind, do you...