Sissy Cage Stories

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Infinite Scroll

Last Friday: First Sissy Experience

by sissysyzygy on Mar 5, 2018
Transsexuals & Crossdressers

Been a lurker for a little while, and thought it was time I contributed with a post! *** Title: Last Friday "You ready for your surprise?" she asked me coyly. "Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd 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 bac...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

Something New Something Old Ch. 03

by dorian87890 on Sep 25, 2017
Fetish

Ted's life had been turned upside down in the last five weeks. He was currently on his hands and knees in the bed of his neighbors' Josh and Nancy. A pair of pink panties were at his ankles and he was wearing a matching pink bra. His cock dangled between his legs trapped in a cage. Nancy was behind him with a strap-on. She was fucking Ted mercilessly. Josh...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

28 Days

by tinywhiteboi on Dec 2, 2019
Interracial Love

28 days. That's 4 weeks since my last orgasm. And I was so horny, to the point of constant distraction. It was all I could think about. My locked little penis was dripping into my panties, and my little balls were swollen. Six weeks ago my wife, Angie, caught me jerking off to interracial cuckold porn, a video with the cuck locked in chastity. She'd come ho...

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...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...