Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Renee's Training

by UniversalReader on Sep 26, 2017
Transsexuals & Crossdressers

AU: The age of the characters in this story are not listed so that you can make the age fit you're desired age group. Assume by default that all characters are over 18. Nathan was an average teenage boy. He was slightly shorter compared to most of his friends at school; but other than that he was average height. He was thin, he wasn't very muscular but h...

Ms. Tanaka Fixes Me Ch. 02

by chenwanli on May 4, 2020
BDSM

Chapter 2- Ms. Tanaka Takes Charge Ms. Tanaka stood up, straightened her sheath dress and bowed to her daughter Hiroki to say goodbye. They exchanged a few final words in Japanese that I didn't understand, gesturing at me and smiling then Ms. Tanaka laughed throatily and demanded the rest of my clothes. I took my pants off from around my ankles and gave her...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

Developing Emma Ch. 04

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

Emma took comfort in the shoes he'd bought her as the days passed, and as she slept she thought hard of the warm suitor's face and kissed her pillow; her anus tingling sweetly on the butt plug, imagining the beautiful sensation she'd experienced when he'd mastered her for the first time. She yearned for him and hoped he'd not just used her for a moment's ple...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

Yeliza Awakens Pt. 02

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

Part 2 of 2, hope you enjoy. Feel free to leave comments or thoughts. Or not, all good. Part four: The reveal Seeing him fully dressed, submissive, and made to look like a girl, her power was readily apparent. She reveled in it. He was patiently sitting on the bed, waiting for her direction. This power was becoming addictive. She enjoyed it more every ti...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Abuse my Sissy bitch

by Red10Dog on Mar 3, 2020
Fetish

This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic! So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino. I am not ready dress him out in public yet, but I am getting close. I decide to slut mysel...