Sissy Boss Stories

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Orientation
Length
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Infinite Scroll

Another World Ch. 02

by dragontatto on Sep 13, 2017
Sci-Fi & Fantasy

Alexa watched as her brother, Andrew escorted in their new lab tech. Both carried the glow of satisfaction. She smiled at both of them in greeting. She would have to pull Grace aside later and talk to her. She was sure that her brother had treated her new friend well. After Andrew passed her, she caught Grace's eye. 'Meet me in the break room,' she mouthed....

Center of Attention: My Boss Ch. 02

by cheatingwife on Sep 17, 2017
Loving Wives

This is the second part of my sexual experience with my boss, Dr. Scully. Last time I told you about our failed attempts to have sex in his car and our successful sexual experience in my tub. All three of these experiences happened while my husband was out of town. When my husband is in town my time with Dr. Scully was more limited, but we did have a time s...

The Waitress Ch. 02

by showife on Sep 25, 2017
Erotic Couplings

Here's part two. Thanks to those who thought it would be worth writing. There will be more as I find time to write. If you haven't read part one it contains all the background and you may want to read it first. * I showed up at the restaurant a few days later for my weekly breakfast stop and was more that a bit curious about what I was going to receive fro...

Farmer's Daughter

by chevy3210 on Aug 31, 2017
Erotic Couplings

She squealed with delight as the young blonde haired stud sank his 9" shaft of man meat deep into her aching cunt. The youngest daughter of a local farmer, the short, heavily busted, voluptuous black haired girl was just at this moment crouched over taking a fat giant cock right into her burning hot pussy. "Damn you farm girls sure are sweet lil pusses," T...

Giving the Boss a Present

by Brookell on Sep 14, 2017
Fetish

On this fine and lovely Monday morning I was cursing the sunlight through my office window under my breath. The first workday back after New Years was always hell! Not only did nearly two weeks of work pile up, but the too much partying last Saturday night while watching the Wildcard games was still bouncing around the remains of his brain. "Headache" was su...

All My Christmases at Once Ch. 01

by HenryWilcox on Sep 2, 2017
Fetish

This is my first attempt at a story, so please let me know what you think of it. Sadly, it is a work of fiction. (C) 2000, Henry Wilcox Permission to post this on the internet is granted, provided this notice is left attached. * It was the office Christmas party. The company had hired out a hotel and conference centre for us to use, and had organised an e...

Shemale Pussy

by Anal Slave on Sep 12, 2017
Transsexuals & Crossdressers

My wife Carol loves to bring she-males home for me to suck and fuck while she watches and masturbates. She works at a club that has she-male entertainers and there's nothing like having a hot she male straddling your lap so you can oil her smoothly shaven body down with baby oil. It's even better when she raises herself up slightly and spreads her ass cheek...

Blonde Ambition

by SweetGeorgiaBelle on Aug 18, 2017
First Time

I drive up the long winding driveway to the house with anticipation and a bit of dread. I had been planning this for quite some time but working up the courage to act had taken longer than I had imagined it would. My palms feel a bit damp but not as damp as my crotch. I blush momentarily at the thought of how aroused I am. My heart feels like it is beating s...

Lunch With The Boss

by Rontonia on Sep 12, 2017
Erotic Couplings

I parked my car and walked up to the door at the end of the two story motel building, as I'd been instructed. I pulled at the door but it was locked. Of course, I don't have a key card. I'm standing there wondering if he saw mw pull in. He told me the door had been unlocked, so would he just wait without looking for me? "Sorry," Dick pushed the door open,...

Photographs and Memories

by dwaino on Sep 17, 2017
Loving Wives

Over the years, the wife and I have experienced the pleasure that comes with the adult lifestyle that few couples successfully enjoy. She has always been amorous, and her sexual appetite has at times been insatiable. I am not the jealous type, and actually enjoy sharing her with various partners that she has had over the years. While there isn't much we don'...