Sissies Stories

490 results
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Infinite Scroll

Charlies Sissies

by Bisexual Zam on Apr 29, 2025

Once upon a time, there were three very different little boys... who grew up to be three very different Glammed-up, twerkalicious, super slutty Booty Boiz. They have three things in common: They're brilliant, beautiful... and they work for me. My name is Charlie. The sissies were hired, trained, and given new identities. Their old identities are lost to the...

Don Venuto's Sissies

by marybethsanford on Aug 18, 2017
Fetish

Players: Capo De Matzo, counsel to Don Venuto. Don Venuto also known as the Godfather; Mario Venuto, son of Don Venuto; Ms. Rosa Cappella, professional dominatrix; Carol Evans, mother of Mark Evans; Mark Evans aka Martha Evans; Helen Andrews owner of the Little Miss Muffin Boutique; Ralph Summers, a friend of Mark, aka Robin; Steve Franks, friend of Mark, ak...

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Robin and Jimmy Olsen - Sissies Ch. 03

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Part 3 Jamie’s story The few days before the date in Part 1... The car pulled up at the curb and Jamie got out of the passenger side door. She was a bit wobbly on her three inch heels. The car sped away fast, as if the driver was feeling guilty about what he and Jamie had just done. Jamie opened her purse and tucked away the fifty dollars she had stuck i...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

Of Dickgirl Mistresses & Dickgirl Sissies

by keemt on Sep 24, 2014
BDSM

There was a knock on the door, here in your top-level apartment. You open the door and look down to find a woman, kneeling on the carpet with her head facing down. Her long, straight black hair flows over her pale naked figure. Although you can't see everything of the woman's body, she is obviously in good shape. Her hair and posture is even blocking a v...

WORLD OF SISSIES

by Emmza on Dec 4, 2020
Fetish

*You wake up in a daze, you do not know how long you have been passed out for, feels like ages, years even.. You finally come to your senses to see a blue elf about 5 feet away from you, going through some weapons in a chest, "Ah yes, this will do nicely" the elf says as she finds a bow and some arrows, you make a crackle with your chain, She looks...