by
Stillherer
on Sep 16, 2017
Transsexuals & Crossdressers
It was the 70's. Young, carefree, long-haired hippie, away from home, traveling around the country - having a ball. A couple guys I met and I decided to go for some beers. The local Y was in a sleazy part of town. So we ended up a pretty seedy bar which was hosting a rather bizarre strip show. At another table was an older guy that had been at the Y that aft...
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by
darladevour
on Jul 25, 2018
BDSM
My leg nervously rocks beneath me in my desk chair as I look at my phone. 11:58 a.m. Shit. I unlock it, scroll over to my text messages and open up my message for fag. "Two minutes, boy, and I'm heading your way. You'd better be hungry." It was lunchtime.
I hop into my car, buckle up, and drive the 3 short miles to his workplace. As I drive up, I see fag wa...
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by
corduroysissy
on Mar 6, 2018
Transsexuals & Crossdressers
Mistress Betty - Part Two
When Karen returned from the kitchen she was holding a drink in each hand and the sight awaiting her not only shocked her, but stopped her dead in her tracks. Betty had her skirt pulled up on her belly and Debbie was between her legs licking her pussy. Betty's face was upturned, her eyes were closed and she had a very contented smi...
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by
corduroysissy
on Jul 24, 2018
Transsexuals & Crossdressers
As Casey sat blindfolded and sipping his drink he thought about asking Mistress Dorothy just how many mystery dates there would be, but he decided against it. She was treating him pretty nice and he didn't want her to think he was complaining. After sitting quietly for several minutes he heard her make a phone call, then listened to one side of a conversatio...
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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...
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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...
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by
corduroysissy
on Dec 18, 2018
Transgender & Crossdressers
Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...
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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...
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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...
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by
corduroysissy
on Aug 1, 2018
Transsexuals & Crossdressers
Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out.
Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again."
She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?"
She chuckled. "Sorry siss...
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