Tied Together Sissy Stories

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Lucy's First Submission Ch. 10

by StrictDom on Sep 19, 2017
BDSM

My new sissy boy has now been tied, hung, and forced to stand on tiptoes for almost 13 hours now. A few times, his legs gave way, and he collapsed, pulling the chain around his balls up. That chain was the only thing stopping him from falling, so all his weight was on his balls. Trust Me, those screams were beautiful, especially when I began beating his ball...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

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...

Humiliated Sissy Husband Ch. 03

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

"Come on Max, I don't have all day." Tanya was running the water in the kitchen sink making sure it was hot enough to shampoo Max's hair. Max stood just out of reach shaking his head. He was wearing a girdle, padded bra and a slip. He had a towel around his neck. He was wearing 6" red high heels because, that's what Tanya said sissies wore around the hous...

Humiliated Sissy Husband

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

Content Warning: To Literotica readers. This is a story of degradation and demeaning of the male sexuality as retribution for an extra marital affair. It consist of a strong female character and a wimpy willing male character. The sexual hypocrisy built in the story is intentional an meant to be part of the demeaning aspect. There is "NO" gay scenes in the s...

Tranny G, Gang Bang Queen, 5

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

I apologize - I had no idea I would continue to write about Chris and Tranny G or I would have numbered the stories. These two beloved people are so rooted in my life and there is so much to share. I never imagined I would share these stories with anyone. Since my husband and I became swingers, I had no idea what my interests would be, I just simply plunged...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...