Sissy Boss Stories

46,032 results
Orientation
Length
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Infinite Scroll

Fair Swop?

by Britease on Sep 14, 2017
Loving Wives

A little snippet. A quick flash story for you all. No sex whatsoever, and little background. You've been warned. +++++++++++ "Wow! This one's nice." "Nice doesn't describe it," I told the beautiful woman hanging onto my arm. "It's the new Jaguar F type - R. Five litre supercharged V8 and does 0 to 60 in four seconds and just short of 200 miles per hou...

The Shadow Man Pt. 01

by RaeynaRed on Sep 13, 2017
Erotic Couplings

He sits in the shadows of the bar, quiet, alone—drinking rum and Coke. I know this because I saw the top-heavy waitress take his order, and then I heard her tell the bartender that that's what she needed for "the guy over there." Her boobs jiggled as she tossed her head in the direction of her customer. I've been watching him out of the corner of my eye. Hi...

Pippa and Harry Ch. 06

by ColinRupert on Sep 17, 2017
Loving Wives

Please do not read if you do not like stories where the wife finds she likes to be the 'boss' and the husband finds he likes to to 'submit' and particularly plese do not ready if you dislike Cuckold stories... For the rest of you guys a short chapter... but hopefully a fun one to kick on with some more 'games'... The following morning I was awake quite...

Getting Rid of the Blues Ch. 02

by Realistic Angel on Sep 12, 2017
Erotic Couplings

Alex caught her breath as she walked out of the bar. He had never made eye contact with her before let alone speak to her. She felt a familiar pulse growing between her legs. She truly did wish he had jumped over the bar and fucked her. However, it was too late now. She had to make it home for a new pair of panty hose. Alex had promised her boss that she wou...

My New Friend Amber Ch. 04

by oddwon69 on Sep 16, 2017
Fetish

I was left kneeling on the beach, naked, with cum dripping from my pussy, and my boyfriend leaving arm in arm with the woman who had just made me come by humiliating me in front of the whole beach. I layed back on the sand and watched them walk away. Then I wondered how I would ever get home…..or even off this beach. Everyone around the crowded beach looked...

I Hate You, Call Me

by unexplored_worlds on Aug 29, 2017
Erotic Couplings

This is a bit of a weird story, to say the least. It's got elements of true tales to it. It's part fantasy part reality. Truth is, I like being someone's fantasy girl; but what happens when that desire becomes insatiable? * You want to know why I started texting you? Why I started sending you partial nudes and telling you all my dirtiest fantasies? Let's...

A Time To Work or a Time To Play

by WileyAttitude on Sep 1, 2017
Group Sex

I had just opened up my own hair salon and I had room for two more stylists. I ran an ad in the newspaper and was waiting to see what kind of people answered. Crystal called me up and asked if I still had a couple of booths open for stylist, since she was the first call there definitely was. I told her sure but I wanted to meet with her before I said she cou...

My Father's Boss' Daughter

by CaliDude86 on Sep 2, 2017
Erotic Couplings

When Adam was informed that his father’s boss Mr. Lelan and his family would be staying at their house for a couple of days, and that Adam was to be the attentive host to the Lelan’s 18 year-old daughter Alise, Adam groaned. He had met the elder Lelans before, and not only were they loud, overbearing and rude, but they were nothing to look at. Immediately, t...

Alice & Joel: Back At The Hotel

by May27 on Sep 13, 2017
BDSM

She stepped into the frigid air conditioning of her hotel room, leaned back against the door and took a deep breath. She'd met him, spoke with him, touched him, flirted with him, tasted him. She was desperate to finally feel him inside of her, but since she fled the restaurant the way she did...she had no way of knowing when he would show up. But he woul...

The Switch

by Julia7642 on Sep 2, 2017
Fetish

I woke up at 6:00 a.m. to get ready for my interview where I had to be "Julia". I just loved becoming a hot sexy girl. I took a quick shower, shaved my legs then began to transform. I put on a red lipstick, mascara, blush and then I put my shoulder length brown wig on. I then put a sexy pair of black lace thong panties on, nicely tucking my dick away. I then...