Sissy Fag Fucked By Boss Captino Story Stories

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A Visit to a Mistress

by fun4all6969 on Sep 19, 2017
Fetish

I have always craved humiliation ever since I was with a girl who humiliated me for my premature ejaculation and my small penis. I saw an ad online for a girl who loves submissive guys and we chatted back and forth for about 2 weeks before my business trip took me to where she lived. She told me it would be $250 for the domination session and that I had to p...

Abducted and Turned Out Ch. 04

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

I let the landlord in and he immediately pushed me over the arm of my sofa and yanked my skirt up and pulled my panties down. I moaned and purred while he plunged his cock in and out of my pussy, fucking me furiously for about 5 minutes until he filled me with a nice hot creamy load. Then, without a word, he zipped up and left. I stayed there for a couple o...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

Steve's First Adventure Pt. 02

by gbr2004 on Mar 26, 2019
Fetish

Total fantasy. Do not read if not into gay sex, domination and forced fem. ***** After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He...

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

Down The Path Ch. 03

by gbr2004 on Sep 14, 2017
Fetish

This story involves gay sex and forced fem, not your thing, move to another story. * I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't w...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Jennifer Monroe & the Ladies Ch. 02

by corduroysissy on Jan 14, 2018
Transsexuals & Crossdressers

Everyone stopped. The ladies all looked at Jennifer with their mouths hanging open, and Debbie just stood there mortified, not believing what he just heard. "Do you not speak English bitch, I said get the fuck out of here right now. That's your punishment." He didn't move. "Oh, are you feeling sorry now Tinkerbell, well tough shit, beat it, bye-bye." De...

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...