Bondage Sissy Stories

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Orientation
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Infinite Scroll

Do I Want To Leave My Wife?

by Gretatv on Sep 16, 2017
Transsexuals & Crossdressers

Dear Readers, hope you enjoy my little fantasy. * I sat there thinking, turning my glass between my hands, not listening to what was happening around me. Why did it happen? Once again I had had a quarrel with my wife. This time it was too much. I knew I shouldn't have raised my voice and yes I should have been calmer and maybe even docile to her. I mean it...

Family Chastity Story Ch. 02

by antares34 on Jul 3, 2019
BDSM

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+. ***** Having grown bored with how things were progressing with my sissy son, I have recently ventured into a new and fun project –filming and distribu...

Fender Bender Ch. 03

by SissyAndi on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: The following is purely fiction and the property of the author. Any feed back would be greatly appreciated. Susan called me early Monday Morning and asked if I wanted to come over and lay out by the pool with her, she told me that Mark had a business meeting and would be gone most of the day so it would be just us girls. I remembered what h...

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...

Humiliated Sissy Husband Ch. 04

by rik581 on Oct 9, 2017
Transsexuals & Crossdressers

"A Second Helping" "Come along now Max, the guys will be here soon. You still have chores to do first before we are ready," Tonya called out from the open motel room door. The door was wide open as she waited for Max to get out of the car and come in. She had parked in front of the room but across the parking lot. It would be a good 50' walk for him in 6"...

Almost Damsel Almost in Distress Ch. 03

by shawnavinyltv on Aug 24, 2020
Transgender & Crossdressers

I felt Alex moving around the bed, I figured he was going to pee, and sure enough, he came back a few moments later and snuggled back into me. I did really want to ask him about last night's adventure and if he was my mystery lover or not. Though I was pretty sure it was him, the thrill of not knowing, made me wonder who else it might have been. The thought...

Familie mal anders

by Herrtobi27 on Aug 2, 2020
BDSM

"Hi, mein Name ist Tobias Schneider und bin 19 Jahre alt. Ich bin ein Einzelgänger, besser gesagt mache ich mir nicht sehr viel aus anderen Menschen. In meiner Freizeit gehe ich gern in den Park Joggen oder schraube an so manchen Dingen in der Garage. Körperlich bin ich sehr Fit und würde fast schon sagen Muskulös. Um ehrlich zu sein Sexuelle Erfahrunge...

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Devoted Cuck Ch. 02

by cuckyfucky on Dec 18, 2018
Fetish

This is Chapter 2 of my ongoing series. Chapter 1 can be found in my profile. ***** I was cleaning the kitchen in my sissy maid outfit when the phone rang. Seeing it was Lina, my wife, I immediately picked it up. "Hi cucky, are you finished with your chores?" she asked. I could hear music in the background and so I knew she was still at the club. "Yes L...

Suspected Affair - Confirmed

by 69Jance on Jun 1, 2020
Transgender & Crossdressers

Second Part of Suspected Affair After confirming my suspicions, I was looking forward to seeing what was next with a hot wife and a pair of handsome twins. Actually though, from what Maxwell said, they all were looking forward to bringing me out of the proverbial closet and see what is next for their new sissy. Maxwell had said "We should go meet Heather a...

Just Look at Me Now Ch. 02

by GFfan on Mar 2, 2020
Transgender & Crossdressers

When I arrived at my first scheduled play date with the kinky lesbians Jude and Becky, I was extremely well prepared logistically. I had triple-checked the items I'd been instructed to bring and completed all my assigned tasks, including shaving my legs. Emotionally and psychologically, however, I was shakier. I had loved the impromptu feminization we had in...