by
keptsissy
on Sep 25, 2017
Fetish
"I wouldn't blame you if you left me but it would break my heart if you did."
She's sitting at the dining room table. She just came home from being with her lover. She's been gone over night. There is a large stain on her blouse. I know it's his cum.
"He fucked me twice and then he had a friend of his fuck me while he watched. I kept thinking about you the...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
I'd just turned 18 and it was high school graduation. Most of my graduating class was at the raging pool party at my best friend's house. I lived next door to him and his parent's house was the place to be that day and most hot summer days. I didn't think much about the fact that his dad kept talking to me about 'the future' or that he seemed to be around wh...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
It wasn't long after I became his lover that he had me seeing other men. The first time was at a party he took me to several months after I started seeing him. He had me go down on a friend of his while he watched. Assured me all was okay, it would be 'safe'. 'Just do it, you'll do that for me, baby, right?'...I did. I actually enjoyed it. I found out early...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
He's up over the top of me, slighty off to my side with his left nipple in my mouth. He has his hand on my penis and strokes me softly as I suck, nibble and kiss him. I can still taste his cum in my mouth. I can taste my rear end too, it was all over his cock when he came in my mouth.
After he fucked me for over an hour he finished in my mouth. It's the fi...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
"Look at you. You're beautiful, honey."
She sits on the couch and stares at me, a big smile on her face.
"You're the daughter I never had."
She laughs, looks adoringly at me. I'm wearing a short soft tight-knit pink off-shoulder dress. White short stack heel summer shoes with ankle straps that show off my pink toenails. And under it all white satin pantie...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
When I saw the light go on in his garage I felt faint. I had been daydreaming about him, his taste in my mouth, thinking about what it felt like to suck him. Every time I thought about pumping him with my mouth my little thing would get hard. He hadn't fucked me yet, not like I now wanted him to. He'd run his cock up between my cheeks and cum all over my che...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. M...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
"Hold still!" Felt his hand come down across my rear so hard I saw stars, wanted to cry out, stifled it as best I could. He slapped me again much harder, loud 'crack' as his large hand came down across my bare butt, made my cheeks quiver.
I pulled forward but could not get away. He had the index finger and thumb of his left hand in a vice-like circular gri...
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by
keptsissy
on Sep 26, 2017
Transsexuals & Crossdressers
He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...
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by
keptsissy
on Sep 18, 2017
Transsexuals & Crossdressers
I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tuc...
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