Shemale Boss Stories

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Business Trip Delay

by fishgullet on Sep 13, 2017
Erotic Couplings

My boss stuck his head in the door and told me to pack my bags. Sales had hooked a big fish and wanted someone from Tech Services to come to the final pitch to answer all of 'those' questions. Apparently it was my turn and no amount to complaining was going to get me out of it. The salespeople were leaving in the afternoon so that they could have the evenin...

Working Girl

by piekna on Sep 14, 2017
Erotic Couplings

I was sitting at my desk, processing orders and talking to clients on the phone and just basically bored out of my mind. I was also talking to him on Messenger. There was something about him that just made me smile when we talked, and something that made me do all sorts of things I shouldn't do, just because he asked. This time, he told me to take off my ny...

Meghan Ch. 06

by nan12345 on Sep 15, 2017
Exhibitionist & Voyeur

Jeremy Yesterday, Friday evening, Meghan called and enquired as to whether or not I had masturbated since she last saw me and, again, I was able to truthfully answer 'no'. The fact is, that I rather like not doing it; I think about it all the time, get hard as can be, frequently leak a little pre-come but then, deliberately, cool myself down by thinking of...

The Home Improver Store Ch. 02

by Bonodono on Mar 20, 2018
NonHuman

Disclaimer- all names, characters, places, situations, etc are fake and for entertainment value only. They do not resemble any real situations, places or people. Any resemblance is purely coincidental. PPS- sorry for the name, I couldn't really think of anything and then Die Hard 2 came on and well... yeah. ***** "Why am I going with you again?" Anon asked...

Bradley's BJ Queens Ch. 02

by RockSteele on Apr 10, 2018
Group Sex

***ALL CHARACTERS ARE OVER AGE 18*** BZZZ. Taylor was just getting out of class when her phone vibrated. As she pulled it out of the pocket of her skin-tight jeans, she was hit with a pang of regret. She and Carly should not have given Bradley their class schedules. A line in the sand should have been drawn. However, it was 3:30 PM, she was getting out of...

Mom's in Town Ch. 06

by 1sfshermale on Sep 26, 2017
Group Sex

With one hand remaining on her head, holding her mouth on his cock, he used the other hand to pull on the stainless steel chain of the slut's nipple clamps. "OOOOOOOOOOhhhhhh" was all she managed to scream as her nipples stretched from the upward pull. She could not speak because her tongue was trapped under the slab of cock in her mouth. It could only feel...

Sex Lies and Lamborghinis Ch. 02

by aussie_101 on Sep 14, 2017
Erotic Couplings

I was back at the station, locked in an archival room in the basement with Ian, the records boy. I was bent forward over a desk that had been cleared in a hurried fashion with my skirt pushed up my back and my panties around my ankles, my brow furrowed in deep thought while Ian's cock pumped, slowly and rhythmically, in and out of my lightly-grasping box. I...

If It Makes You Happy Ch. 04

by Rocketspeedfish on Oct 13, 2017
Fetish

It was more than a bit awkward that night at the Morgan's. Just as Trevor requested, Vanessa left Jeff's cum in her hair. It had dried by now but a few large pools were visible. "I'm honestly surprised," Vanessa said finally speaking up. "You never expressed yourself like that. It took me by surprise. I had no idea you were into that kind of thing." "I'm...

Oscar Bait Ch. 03: Aish & Stakeholders

by nextcenturyromeo on May 16, 2018
BDSM

Aishwarya walked back through the same hotel lobby in the same tiny little dress. She felt like her pussy was peeking out from under the micromini dress as it felt so swollen. Even after hours of hard fucking, the leering glances of the watching men were turning Aishwarya on and she was running a serious risk of leaking her juices down her thighs before she...

So, I Now Love a Succubus! Ch. 02

by SEVERUSMAX on Jun 18, 2018
NonHuman

"Oh, damn, she really was cheating on you, wasn't she?" Autumn giggled as we discovered my still frozen wife, Lizzie, in the arms of another...woman? My wife was having a lesbian affair, I realized, which was a little bit of a shock, but then it made a certain degree of sense. Her previous partner, prior to me, was a woman named Vanessa, and sure enough, t...