The Loser Jeff Stories

Things you didn't want to know about me and not much more.

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The Worst Sex I Ever Had

Posted on September 30, 2010 at 1:09 PM

Date Occured: September, 2007
Date Written: September, 2010


This story revolves around my one and only one night stand. Normally I don't do this kind of shit, but I was 27 at the time and single with no girlfriend material in sight.  It's one of those situations that you just kind of get yourself into and then once you're in you realize that you made the wrong decision and want to back out but it's too late, the shit roller coaster  has already embarked.

In late 2007 I got a job as a sub contractor working for AT&T in their sales department for their home side products (that means non-wireless shit for those that didn't get that). My job was to go into the wireless stores and try to sell people DSL, unlimited long distance for their landline, or something else that nobody ever wanted.

The best part about this job is that you and only you go out the stores, except for when you get paired up with a coworker, which I never did. One day while I was working this one store in east bumblefuck Alabama, otherwhise known as Jasper, I decided to take a break or lunch break or shit break or some kind of break to go into the grocery store next door.

I find something to buy and goto the check out, where I find a girl I will call "CrazyPsycho" looking rather sad or pissed off or some kind of twisted combination of both. She wasn't a bad looking girl, big boned but not over weight. Her attitude was less than that, giving off some kind of "I don't want to fucking be here much less help you in purchasing your drink" persona. I think nothing of it, and try to make a little small talk which results in me just paying for my shit and leaving.

Sometime later, I'm sitting around try to do my near impossible job because every has cellphones when I see the girl from the grocery store walk in with some dude that looked like he'd just been molested by the Adams Family and then passed onto the Munsters for extra added in creepiness. I will call him "Fester".  They get helped with whatever they needed help with, then CrazyPsycho notices me from the grocery store and decided to come over and talk to me. I guess she got over her bitchy attitude. We start shooting the shit and talk some. Fester was bi or gay or something because he kept trying to touch me and make passes at me. Sorry guy, I don't do dudes much less ones that look like they were born right into the movie Night of the Living Dead. After talking to me, getting my phone number, and rubbing me, CrazyPsycho and Fester leave, but not before CrazyPsycho tells me to call her later tonight. Awesome....or so I thought at the time, little did I know that karma was about smack me down like Mike Tyson.

I get off work and head back to office, then home. This takes awhile as my office was about 50 minutes away and then my house was 20 minutes from there. I get home and change clothes and bullshit around with my roommate some before I decide to call her. When I finally get around to calling her, she tells me that she's still at work but will be off in an hour. This works out well as it takes about an hour to drive out to where she works and lives.  I get to her grocery store and go in. I find her just getting off work and walking my way to greet me.  We walk back to my car making small talk along the way. As we get into my car, she starts asking me questions like do I like her, do I think she's hot, etc. Then she says I can touch her if I want, so I lay a hand on her left breast and squeeze.

After more talking (and groping) we decide to go back to her place, she tells me that she lives with her parents (I think she was only 19) but that won't be an issue as we can go in her room. We get to her house and as we walk into the kitchen, she decided to dart somewhere and leave me with her relative of some kind. I guessed her mom but it could have been her cousin or aunt or someone which was a very odd moment for me which I won't go into because I don't remember what was said...yeah it was that awkward.

She comes back and says we can go in her room, so we do. We are sitting on her bed when her mom or whoever screams for her. You see, here in Alabama the rednecks prefer to scream across the house or yard to get someone's attention, yeah it's one of those southern things.  She leaves the room and comes back, but doesn't close the door. I ask why is the door open, she says she has to leave it open. Okay no worries, she had a huge walkin closet, we could go in there. WRONG!

So with the door wide open and her not wanting to go in her closet and shut the door, we decide to fuck on the floor by her bed...with our clothes on. We go at it for I don't know how long (it wasn't very long at all because I was paranoid and uncomfortable as fuck so my goal was to get in, and get out).

Finally, as I'm pounding away it looked and sounded like she came, okay awesome now I can come and get the fuck out of here. I pull out, take the condom off, and ask if she will suck me off. She does and it was almost the worst head I've ever gotten in my life, only 2nd to this girl I fucked around with on my 16th birthday that used her teeth and made my dick bleed, obviously not knowing how to suck dick but that's a whole other story entirely.

She's sucking me off and as I'm about to cum she pulls away and jacks me off all over my clothes!  WHAT THE FUCK!?!?! After I cum and think we are all done I start to get up (with jizz all over me) and leave. She then tells me that she didn't cum and wants me to finger her. I tell her to give me a fucking towel first, she does, I clean up as much as I can and then start fingering her. I can't remember if I went down on her or not but that's probably a good thing since the whole situation was a fucking disaster. I finger her and I guess she gets off. By now I'm super WHAT THE FUCK!? , uncormfortable as hell, and this mental basket case in all into me...great, story of my life.

We finish, put what little clothes we took off back on, and then I get the fuck out of there.  She tells me to call her...yeah right, I'd rather stick my balls in the microwave. I make a B-line for my car, get in, and haul ass as fast as possible away from her house.  She called me a day or 2 later, I talked to her for a whole 2.3 minutes then make up some lame excuse to get off the phone. I was not digging this chick, but she wouldn't stop calling me so what do I do? I let my roommate at the time start answer my cellphone. This was funny as shit because he could do a great impression of me while stoned, so she never knew that she was talking to him, she thought it was me talking to her.

I have no idea what my roommate told her, but everytime she'd call I'd hand him the phone. Finally she stopped calling me and I didn't know why at first as she'd been calling me for nearly a week straight everyday just about. Then my roommate filled me in on his fiendish plot.  He had made up some crazy shit and told her that I became gay and started liking a dude I worked with.  The funny thing is, they would talk for a good 20-30 minutes each time she'd call and I'd give him my phone. Who the fuck knows what else he told her or how far into detail he went into my new gay experience with a coworker, but whatever it worked and she stopped calling me. Just goes to show how smart Jasper, Alabama girls are.

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1 Comment

Reply Tamz
3:39 PM on October 28, 2010 
TOO MUCH STALKER STYLE!!! HILARIOUS!!! (I must say that stories about disappointing sexual escapades... they totally make my day!)

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