Bro Has Sex With His Boss, Plus Dude Endures the Worst Hook Up of His Life

by 6 years ago

So I just got promoted and moved to a new site at work. What I didn't know was that along with a pay raise and a kickass polo, my new Assistant Manger position would come with some bonus perks. My new boss is 28 and had been eyeing fucking me up since I interviewed a couple days before for the promotion. We will just call her “the boss” for simplicity sake.

After my first day on the job the boss starts texting me a lot. After the second day she starts snapchatting me suggestive pictures while she is out at the bar. It's a Thursday night, and I had a big weekend of raging coming up so I decided to just kick with a few bros and smoke some wax for the first time. (That shit is unreal fyi). She starts texting me that she wants to come over and drink at like 3am so I kick the bros out and pick her up and bring her back to the mancave.

We start pounding drinks at my place and soon enough we are in the bedroom listening to the weekend and doing the dirty. We've been going at it for like a half hour and I get tired and start trying everything possible to finish so I can catch some shuteye. Smacking her ass, pulling her hair, the works… but it just wasn't gonna happen especially with rubber on so I pull off the condom and raw dogging it…She starts saying all this freaky shit like how this was my “employee training seminar” and the shit she wanted to do to me at work. I end up finishing and busting all over her titties. She got so wet that she soaked through my sheets and we had to pull the covers off. I try and pass out, and she won't let me go to sleep cause she keeps grabbing my dick.

We go round two.

I pass out for a half hour and get woken up for round three.

At this point its 6am and I am so tired that I can't even get up from the bottom so I let her do all the work. After that I take her home. The next time we are at work she whispers to me that she wants to blow me in the bathroom. Normally, I would be down for that sort of thing, but see the thing is we work at an elementary school with little kids… and I am not trying to be a sex offender. Work is gonna be a whole hell of a lot more interesting now, though.

Just say no, Bros….to speeding and blow jobs in a school zone. NEXT!

It was the last semester of my senior year in college. Needless to say I was drinking a shit-ton.  Well this one fateful Saturday night I was in my fraternity’s basement, absolutely plastered, and lookin for some ass. Now, for anyone who has never been in a frat basement for a dance party before, it is dark and loud, with the only available lights being the black lights. The point is that it’s hard to see. Well I’m scanning for someone to dance with when I see a lone girl eyeing me up, standing in the darkest corner of the basement (That clever, clever, unattractive girl). We will call her ‘Sinead O’Connor’. I saunter on over to Sinead, we go through the formalities of dancing but really its straight to the dance floor make out and grope session.

I get her to leave with me, and as it turned out she was just visiting for the weekend, she used to go here so she is just seeing some friends. Perfect.  Well we get back to my place, fool around, then, only when she is  COMPLETELY naked on my bed, does she decide to inform me that she is on her period, and we can’t have sex.  Now, this is fine, I am not the kind of guy to relentlessly pressure someone into banging, that decision is entirely up to the lady, but why wait until you are completely naked on my bed to tell me? Who could possibly benefit from this? Well I say fine, thinking there is still something coming (if you catch my drift), but I was mistaken.  It seemed that since she wasn’t going to get any, neither was I.

Well by 4:00am I am pretty wiped and too nice to kick her out (won’t be making that mistake again), so I try to just fall asleep. Well as it happened during the course of the 3 hours we had known each other she decided that she had a pretty big crush on me, and kept saying weird dramatic things like ‘don’t fall asleep, this is our last night we have together! We have to make this count!’ Literally, she would not let me fall asleep; every time I drifted off she would shake me awake, but still wouldn’t touch my Johnson.  So I essentially just played dead until she passed out (the sun is coming up now) and I go out to the couch to finally fall asleep. I wake up at 10 hoping to find her gone from my room. Not so.  She was curled up to my pillow, still naked, so I had to wake her up and escort her out.  As she departed I noticed that her right eyebrow had smeared off, but I chalked it up to nothing more than self-conscious chicks drawing on their eyebrows to make them look perfect or whatever.

I return to my bed to get some much needed sleep, pull back the sheets and discover an ENORMOUS red stain in the middle of my sheets.  Utterly horrified I decide I have to take a shower, immediately, or else I will vomit everywhere. So I grab my nice, white, cotton towel from my door, open it up to wrap around my naked waste, and discover yet another big red period stain!  It’s like this girl just decided that since she liked me it would be okay to bleed out all over my room! Or else she had an utter emergency and decided to use any available loose clothe in my room.  So I washed it all with enough bleach that it ate through my sheets, then I slept outside on the couch for a week as a precautionary measure.  Disgusting right? It gets worse!

After going to share this story with my bros, as one must, my friend recognized her name.  “Wait, you said her name was Sinead? Like, Sinead O’Connor??” yes? “Holy shit man! I know her, that chick is bald!” Apparently she had some kind of condition that she could grow no hair, so she had to wear a wig all the time (see: drawn on eyebrow).  Although, I wouldn’t have known because we never got to the hair pulling portion of the night (imagine what a shock that would have been).  Well, to top this all off, she gave me an awful case of pink eye(s) that lasted for a week. It was unequivocally the worst hookup of my entire life.

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[Sex with boss image via ShutterStock]


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