Femdom Sissy Stories

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Forced Femme

by Mrfriskay on Aug 11, 2018
BDSM

You've always been kind of a nancy boy. A little afraid of women, and awkward. The attraction has always been strong though, especially to dominant women. It was always obvious that you were a little different, but things changed when you met her. She wasn't typical in any sense of the word, and you find out the hard way.What's next? Annabel Lee, 6'1&q...

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Dinner Date with Mommy Pt. 02

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

Part 2 picks up right where Part 1 left off as Sophie prepares for the arrival of Victor. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and anal play, feminization/sissification, spanking, CBT, humiliation, chastity, and domestic servitude. Enjoy! _____________________________ Part 2 Sophie was sl...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Dinner Date with Mommy Pt. 03

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

Part 3 is going to go a little off track from the previous two parts. I've been asked numerous times for more backstory on Sophie and Amanda, so we're going to go back in time to the day after the events of Meeting Mommy to see how their relationship really began to evolve into the kafkaesque clusterfuck of sexual depravity you're all so fond of. This story...

Blackbone Crossing

by DonSwami on Dec 4, 2020
Fantasy

AUTHORS NOTE: This story is still a work in progress, I’ve got a lot of idea’s on where I want to take it and what different chapters are going to be. I decided to publish Blackbone Crossing because I really wanted some feedback/ideas. The story is open to other writers, so feel free to submit your addition! Some chapters I’m still working on and I haven’t p...

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Lessons Learned

by MsCM on Sep 16, 2017
BDSM

In the way of a warning: There is no category for 'bisexual' here, so I hope the tags help. Although this piece starts with a cross-dressing sissy/femdom scene, a lot of the later parts of the story is MMM, with the female character only turning up at the very end. It's not *forced* bi either. ***** The woman next to him at the bar lit a cigarette, a long,...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Sissy Academy

by Tricentennial on Apr 28, 2018
Transsexual

Your name is Allen George, you are walking home after work, when you get a message from your girlfriend, Samantha Conners, saying she has a surprise for you. With this is mind you hurry to your apartment. You get home and open the door to find it pitch black, you flick on the hallway light and take off your shoes. “Samantha?” You call out as you walk down th...

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Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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