Puddin' Hooks Up With His Boss

Off the bat, I must tell you that this happened my senior year in college. I would never hook up with any of my superiors at my present place of employment for a number of reasons, the least of which is the fact that I'm married.

Anyway, I worked for Residence Life as a "Security Guard" at the front desk of one of the on-campus apartment buildings. I use the term "Security Guard" lightly, as I kept that place about as secure as Paris Hilton keeps her vagina. Unless the person coming in readily admitted that he was there to rape girls, I didn't really care that much. And even that guy seemed pretty cool, so I let him in anyway. There were 2 types of people in my situation... the people like me who got paid close to minimum wage to do nothing because they needed money to buy beer, and the people who made Res Life the most important thing about their college experience. The latter were the same people who would tattle to DPS when you were having a kickass party. Fuckers. (By the way, I believe PV was an RA in college. What an assbag.)

Well, my direct supervisor, who may have been in grad school or something, had a little crush on me. But I assure you that was the only thing little about her. Here is a picture of her:

And that's her good side. She always flirted with me when she would check on me at the desk. It was gross. I'm no GQ model, so I don't know what the big deal was. Anyway, she loved me. And I knew that. And I hated it.

A quick sidenote... women in college sometimes pick an arbitrary character or animal to be their favorite, and they cover their cars, walls, notebooks, purses, whatever with it. You know what I'm talking about - Tweety Bird, Ducks, etc. My boss chose cows. I shit you not. She had to be tipping the scales at Super Heavy Weight, and she chose fucking cows as the animal to love and have all over her shit. Now, she wasn't 7'2" or anything. Apparently she was as dumb as she was fat.

Back to the story. She got my AIM screenname from one of my friends, and would periodically IM me. Remember in college and grad school when AIM was the rage? I bet I haven't logged on in 2 years. Anyway, the first time she IMed me, I had no clue who it was. She told me, and I cringed. I couldn't block her, because we apparently had mutual acquaintances, and she would know if I was ducking her. Plus, she's my boss. At least tolerate this for a while, right? Haha. No.

One night I had come home drunk. Let me rephrase that... many nights I came home drunk, but on this particular night, I decided that drunk IMing, which I had previously and ever since condemned, was a fantastic idea. So I was typing completely inappropriate things to some of my female friends. What do you think happened, when all of a sudden, an IM from my fat fucking boss appears! Since I was saying inappropriate things to 10 other girls, I decided that one more was no big deal. Well, my boss was sober as can be, and took it as me being interested. With the number of female friends telling me to stop typing and go to bed increasing, my chances at ass were dwindling. If the title of the entry didn't clue you in, I think you now know where this is going.

So my boss and I are chatting, and she invites me over to her apartment. Immediately, I recall the old adage: "Fat chicks give great head." Who couldn't use a blowjob, right? It's 3AM, I'm drunk... it's destiny! So I take the 10 minute walk to her apartment.

I knock on the door (which has a cow dry-erase board on it). She opens the door, and fills the entire doorway. She invites me in, and I recall thinking that unless she moves, there was no way I was getting past her. Well, she moves. Cows everywhere. Fucking calendar, fucking dishes, fucking screensaver... EVERYWHERE! I'm starting to regret my decision to come over, when she asks me if I want to make out. Of course, I don't want to, but to get my BJ I probably have to stomach the foreplay a bit. So we, umm, make out.

I can say with 100% certainty that it was unlike any other make out session I had ever had before or since. At the time, I was 6'2, 250. I'm a big guy. When I made out with my boss, I was ON TOP! It was surreal. I tried to enjoy the novelty of it as much as I could. If the positions had been reversed, I would not be here today to share this story, and my boss would have a tragic story to torment her for the rest of her fat years.

Well, even drunk, I can only put up with so much of this. So we stop making out for a bit and she wants to talk for a while. Fuck. Really? This is why I walked my drunk ass to the other side of campus at 3AM? Hell no. Well, she stuns me with a question... "Are you attracted to me?" This is by far the dumbest question a woman of her caliber can ask. There are essentially 2 possible answers: 1) the painful truth; or 2) a lie. She should know this. I assume she has seen herself in her extra wide mirror or has had to pay for multiple plane tickets before. Why the fuck would she ask me that? Well, even drunk I'm still a tad clever. So I avoid option 1 or 2 by throwing a question right back... "Would I be here if I weren't?" Ha! Brilliant! She totally bought it. Again, she's apparently as dumb as she is fat. Regardless, we're headed to the bed and I'm headed for my blowjob. (I can't believe that fucking bed held the both of us. It must have been really really close to the max capacity.)

So I lay down and she begins to take off my pants. With moderate whiskey dick and moo moo doing the work, it was a challenge to get, umm, prepared. So I thought of this:

(God she used to be hot!)

I was able to distract myself enough to achieve an appropriate level of excitement. Wait... what the fuck is... ouch... are those her teeth?? Jeezus christ! My fat boss was practically chewing on my dick! Well, it didn't feel good. It didn't feel good at all. I almost smacked the top of her head, which certainly would have made this story better. But I decided to grit my teeth and bear it. Regardless, the old adage was wrong... i.e. I reject the universal truth that fat chicks give great head.

So I give her the courtesy of letting her know that I'm about to pop. In what was no shock to me, nor should it be to you, she decides that she is, in fact, hungry. Let's just say, no clean-up. At this point, she had not yet taken off her clothes (thank God). Even if she had, I'm not sure I could have found her vagina without a helmet and a dipstick. But I get the sense that she wants to get naked. How dumb is she? Most women know the following, but for those that don't and are reading this... never EVER get a guy off first if you want yours. Never. It'll only happen if he's in love with you, and sometimes not even then. Right, honey?

Well, she asks me to make out with her again. Given what just happened in her fat mouth, there is no way I'm going to make out with her. I know for a fact at least one thing that was in there, and there may have been blood and little bits of flesh as well. No way. No fucking way. But, I have an idea. I kindly tell her that I don't like making out after I just blew up in a girl's mouth, and I asked her if she would mind brushing her teeth. She viewed this as a reasonable request, as I'm sure she hadn't had any action in a really really long time. A ha! My plan was working. She went into the bathroom to brush her teeth (and probably apply deodorant to her arm and fold-pits). I pull up my pants and get the fuck out of there. Part of me wishes I could have seen her face when she got out of the bathroom. But most of me is delighted I didn't have to see what was behind (in, over, and around) Door #2.

What a night, right? Yeah, well, I got fired the following week. Something about how I didn't follow Res Life protocol when working the security desk. Yeah right. So NOW they are going to start enforcing that policy? Nevermind that the given reason was completely true... it was a total pretext. I was kinda pissed, because there went my alcohol revenue source. But whatever, it meant more time to do my favorite collegiate activity - nothing. I think I'm still paying Citibank for the alcohol they bought me the rest of the year.

There's a brief follow-up to the story that I'll post soon.

~Puddin'