Sissy Fag Stories

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Orientation
Length
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Infinite Scroll

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...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

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...

Jennifer Monroe & the Ladies Ch. 03

by corduroysissy on Jan 31, 2018
Transsexuals & Crossdressers

Debbie gave Miss Jennifer's boot one last kiss, took a few seconds to straighten out his dress, then walked over and knelt submissively next to Patty in front of Miss Marsha. She let Patricia continue to suck her dick and lit a cigarette, she didn't even look at him, in fact she totally ignored him for several minutes. She did however blow smoke in his face...

Casey's Submissive Journey Pt. 03

by corduroysissy on Dec 16, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part One Audrey was dressed in a pair of tight black mid-wale corduroy jeans and had an 18" dildo sticking out through the fly of her pants. She laughed maniacally and grabbed Casey's balls. "I own you sissyboy. First I'm gonna yank on your sissy balls til you beg for mercy, then I'm gonna fuck your sissy ass with my big cock...

AliExpress and Sissy Downfall Pt. 04

by His_fag_wife on Dec 30, 2017
Transsexuals & Crossdressers

As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets...

Mistress Sylvia Pt. 02

by corduroysissy on Dec 19, 2018
Transgender & Crossdressers

Having gotten a good look at what would be his future living quarters, Debbie followed Mistress Sylvia through a doorway and down a second corridor of bedrooms. She explained that the rooms were where the fags did their whoring, and the door at the far end of the hallway was the client's entrance. Just before the end of the hall was a set of double doors on...

AliExpress and Sissy Downfall Pt. 09

by His_fag_wife on Aug 20, 2018
Transsexuals & Crossdressers

Charlie stood wobbling slightly, on the 5 inch heels. Legs a little apart to accommodate the very substantial base of the Fenrir Dragon cock currently stretching her wide open, holding her buttocks apart and her asspussy wide open with the 2 1/2 inch diameter. She felt better now, shattered and tired but she was basking in the looks of approval from both her...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...