Strapon Sissy Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Power of Panties - The Beginning

by satinmarabana on Sep 12, 2017
Transsexuals & Crossdressers

When I was growing up, underwear was just one of those details of life. Always wear a clean pair in case you get in an accident! Sure it was nice to get sexy pairs as I got older. I still remember my first satin bra and panty set from Victoria's Secret, a gift from my older sister who delighted in showing me the ways of the world. But I never understood wha...

Discovering Amber Ch. 06

by Ms_Allison on Feb 12, 2019
Transgender & Crossdressers

Mistress notes: Once you understand them sissies are rather easy to manipulate and control. It's just a matter of finding which buttons are the ones that need to be pressed and when to press them. amber has a weakness for lingerie, heels, and humiliation. Additionally, she was very easily brought to her knees at the promise of an orgasm. Getting dressed up...

Discovering Amber Ch. 07

by Ms_Allison on Mar 25, 2019
Transgender & Crossdressers

Mistress notes: The morning after is always fun, people tend to get caught up in the moment, sissies included, and amber was no exception. The fact Jenn and I were there to remind her of all of it just made it better! The fact amber seemed to really enjoy humiliation only added to the whole experience. Ms. Allison ~~~~~~~~~~~~~~~~~~~~~~~~~~ The following...

Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

Discovering Amber Ch. 08

by Ms_Allison on Apr 23, 2019
Transgender & Crossdressers

Mistress notes: After 8 or so months of going to the club twice a month amber became a welcome regular and a great dancer. Actually, she danced better in 5" heels than in men's dress shoes, which I obviously teased her about often. I also made sure to keep her embracing her comfort level with being groped while dancing. Her dance partners soon learned her li...

Brandi's Turn Pt. 02

by 9volt on Mar 3, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** So we woke up with my sister looking, mouth agape, at my husband in his torn panties, garter belt stockings and bra and me with a 6-inch strapon cock jutting from my otherwise naked body. There wasn't even a blanket handy to pull over ourselves. There was a pretty awkward silence...

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...

HSPL - Trip to the Sorority

by sissydn on Aug 7, 2019
Transgender & Crossdressers

"After being left on the road by Meghan and Sophie, princess was caught by Cindy and her companions. Zoe, apparently the leader in the group, had informed sissy that she could get back to Sophie and Meghan if she pledged the sorority and joined with honor. If she chooses not to pledge, they would drive her to the other end of town and leave her there in her...

My Girlfriend Made Me a Sissy Ch. 03

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

I lay on Jess' bed waiting for her and wondering what would happen for ages. She was in another room getting ready for her new lover, I was already dressed up. Pale blue, see through panties and matching bra, a short black skirt and a blue vest top. With my make up done to show off my pretty green eyes and my long brown hair styled wonderfully, I looked like...

Birthday Breaking

by purekink on Sep 19, 2017
Transsexuals & Crossdressers

I had no idea what my girlfriend had planned for me that day - and if I did, I'd probably still have gone along with it. My birthday wasn't that special an occasion for me. I had no family and having recently moved, I'd no real friends in the city. But Gen was determined to give me a time to remember, and said she'd arranged a small gathering with her frien...