Cuckold Sissy Maid Stories

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The Boss's Office

by Mistress Sierra on Sep 17, 2017
BDSM

She dresses in her usual attire: a white button up blouse undone to just the top of her cleavage; a black skirt and matching blazer; black, sheer stockings, and black pumps. Her make up is done in a professional manner finished nicely with red lipstick. Her red hair is done up in a bun with wispy stray hairs hanging down on the side and in back. She takes on...

The Arrival

by freaky_devil on Sep 16, 2017
Novels and Novellas

My name is Sandra and I am a 22 year old girl from Austria. I consider myself good-looking and smart. The first I know because I always got the guys I wanted to fuck, and the second I know because I never had a problem mastering my studies, and studying Computer Science is not really a common choice for a girl. I always had a thing for the computer stuff. F...

Michael's Exploration Continues

by cuckietex on Sep 16, 2017
Transsexuals & Crossdressers

The contents were now strewn on his bed. Michael decided to take a bath, and while the water was filling, he undressed, his mind filled with a compulsion to express his dark, unfulfilled feminine self. Naked, he walked with purpose to the cabinet that housed his shaving supplies, picked up a razor, some shaving cream and put them on the side of the bath. The...

The Trade Pt. 02: Nursing an Idea

by jdjangles on Sep 16, 2017
Transsexuals & Crossdressers

Sam finally called me back. It took about two weeks, and I imagine fear was the cause. I was sipping at a glass of scotch, relaxing from work. My day job I should say, Sam and others like him were my real work. I let the phone ring, almost to the point of going to my voicemail, then I answered. "Sam," I greeted, "it's good to hear from you, are you enjoyin...

The Poker Game

by spankherDaddy on Sep 17, 2017
BDSM

I watched as Rita and David came into the room. Daddy was watching my reaction to their presence. We both knew I was uncomfortable meeting with them...intimidated by another Domme. He stroked my hair before rising to greet them. "Good morning, Rita," He said with a smile. "Hello, David." David gave a little wave to me and said hello. "Hello, Alan," Rita r...

A One Night Stand for Tranny G

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

The time had arrived for me to travel to see Tranny G, yet something felt different. I mentioned that HE is a soldier and really, I was never angry about the rape. It was such an experience, that I wander back to and repeat in my mind again and again, wet with the memories of the fear, the fight, the ultimate pleasure. I might as well tell you that I see mys...

Grad Student Slave Ch. 02

by scslutforcock on Sep 17, 2017
BDSM

The dinner went until 10, but I barely remember the end of it. Even as I was cleaning up after, all I could think about was what would happen to me tonight. I couldn't believe the situation I had gotten myself into. Or the man I had gotten into it with. Had it been a nice blowjob, I wouldn't have minded servicing my benefactor regularly. Hell, I probably wou...

Mistress Jamie Return: She Does

by gomez8 on Sep 17, 2017
BDSM

Mistress Jamie has been keeping watch over me. She read my story and has responded. This is her message to me. ------------------------------------------------ "I can't believe the new levels of boring these conferences have reached." You think to yourself as you take a vacant stool at the bar. "What can I get ya?" asks a female voice. "Damn! She is mighty...

Party On

by Sensualist2 on Sep 15, 2017
Group Sex

So there I was, on my belly, naked ass in the air, while this woman I'd only met ten minutes before, was standing over me, straddle-legged, strapping an odd contraption around her hips. It was black, a soft leather triangular piece with a hole in it in front. Two straps went under her crotch and apparently hooked to a wide black strap around her waist. Nice...

Phonesex & More

by burningdog on Sep 1, 2017
Group Sex

I met Sarah in Portland Chat—big surprise there—in late winter 1999. The Internet is the easiest way to meet people. "Does anyone want to talk on the phone?" she asked the room. Bored and a little lonely, I Instant Messaged her. We began chatting. She emailed me her picture. She was chubby and cute. I gave her my phone number, and five minutes later we were...