The Loser Jeff Stories

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

My Stories

Below you will find my crazy ass stories, read them NOW!

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The "I'm a Prostitute" Story

Posted on April 17, 2011 at 2:35 PM Comments comments (2)

Date of Happening: 2007
Date of Writting: 2011

Editor's Note: I will tell you that to this day this is one of the most random things that have happened to me in my entire life and I've had A LOT of random shit happen to me in my time.  With that said, get up and go watch a movie because it's not worth reading unless you're a crude pervert like me.

One Thursday night after work, I was to go out somewhere with the office (yes office, this was when I worked in an office environment) because it was "Team Night".  Basically every Thursday night the office gets together and goes out somewhere to a bar, restraunt, Sloss Fright Furnace, etc. and calls this event: Team Night.  Yeah, lame I know.  "Office Night Out" or ONO for short would have been slightly better.  Team Night was actually kind of fun despite the shitty name.  They had karaoke at one bar we went to, which was fun once I got hammered.  So most of the time I got drunk and more drunk, even though I had work at 8am the following day, but oh well shit happens.

On my way home (still drunker than a street bum) I had to drive through a small stretch of highway with nothing but a 24 hour gas station and a trucking company or 3 on it.  I'm going to pause here and let you insert your own Texas Chainsaw Nightmare on Friday the 13th joke for that one.  I pass the gas station and between it and the first trucking company, I see this fucking hot chick just walking down the street, alone.  Now what would Jeff do in a situation like this?


Still being slightly young and full of cum, I thought with my penis....again.  This has gotten me into trouble before (read my Blowjob Mishap story), but I said fuck it.  I pull over, roll down my window next to her, and whip out the most classic line ever:


"Hey, you need a ride?"


To my surprise she actually said yes.  She gets in my car and we start the usual chatting that you do when you pick up random strange girls from off of the side of the road.  The next part of this story I'm just going to do in context from the best of memory, after reading it you will clearly see that I truely am the King of Random.


Her "Hey thanks."
Me "No problem, the name's Jeff."
Her "I'm Desiree."
Me "Right on, so do you live around here?"
Desiree "No, but how do I get back to Columbus Georgia?"
Me "Georgia is about 2 hours from here and that's just the state line."
Desiree "Shit, I got court in the morning."
Me "Oh damn, I'm sorry."
Desiree "It's okay, so tell me about yourself, you got a girl?"
Me (laughing at the irony) "No, I seem to have bad luck with women."
Desiree "That's because I can tell you're a nice guy and women see that so they take it for granted."
Me "You're telling me."
Desiree "I'm hungry."
Me "I can take you to Taco Bell."
Desiree "Okay."

Boy am I a sucker when it comes to hot women.  I drive to Taco Bell, get her a taco or 2 and then she tells me that she should probably get back to that gas station that her ride is probably there.  On the way back, this conversation takes place:


Desiree "Hey wait, can you go this way?"
Me "Uhm sure."

I should win an award for Biggest Sucker.  After driving around because she's acting rather confused, I ask her what's up and eventually get back on course to the gas station.

Me "Are you okay?"
Desiree "Yeah, it's just the Xanax."
Me "What? You're on pills?  Are you a pill head?"
Desiree "Well no, well sort of, I mean I get them prescribed."
Me "Oh okay."

Some other random nonsense chatting took place and then she drops this bomb shell on me.


Desiree "I'm a prostitute."
Me (in shock) "Say what?!"

Okay she was wearing jeans and shirt and a jacket like thing.  She did not in anyway shape or form look like a hooker.

Desiree "Yeah, and for $80 I'll let you fuck me."
Me "Uhm, I don't have $80."
Desiree "Well do you have any money I can have?  I got to find my boyfriend so I can get back to Georgia."
Me "Wait, boyfriend?!?!"
Desiree "Well he's more like my babies daddy, but yeah.  He's cool though, he knows I fuck guys for money."

I didn't know what to think or how Jerry Springer this has become.  I pull into the gas station and park, we sit for a few minutes and start talking again.


Desiree "Please, do you have any money?"
Me "I guess I could spare $20.  I have to get it out of the bank though."
Desiree "Oh thank you!  Now I just have to find my boyfriend."
Me "I want something for it though."
Desiree "Like what?"
Me "I don't know, blowjob or handjob."
Desiree "What will cost you more than $20."
Me "Okay, how about if you let me jack off in front of you?"
Desiree "Okay I can do that, and I'll masturbate too."



Not too long after we have come to a very odd exchange agreement, her boyfriend pulls up in a SUV, she gets out and runs over to the driver side window.  I'm just sitting in my car at this point thinking what the fuck?  She then comes back over and asks me for my cellphone number.  I give it to her and we head back to the bank which is right across the street from the Taco Bell I was just  By now it's midnight or later and I'm running around with a crazy pill whore and her boyfriend when I should be at home asleep.  Story of my life.


I get to the ATM and my phone rings, it's a number I don't recognize so I answer and it's her.  She tells me that it's going to cost $40, not $20.  Thinking that I would get paid in a few days, I said fuck it and went with it.  I tell her to meet me in Taco Bell's parking lot in the back.  I get to Taco Bell and wait.  I see the familiar SUV pull in and the little blonde hottie known as Desiree jumps out and comes over to my car and gets in.

Desiree "You got the cash?"
Me (handing her the money) "Right here."
Desiree "Awesome, thanks."
Desiree "So for an extra $30 I'll let you fuck me."
Me "I would because you are hot, but I don't have the money nor do I have any condoms."
Desiree "Hey, you're right, we would need condoms."
Me "Yes, and plus I don't have much time now."
Desiree "Ohh okay."


Now picture this:  2 people masturbating in a Taco Bell parking lot late at night while the place is still open.  She then pulls down her pants and starts rubbing her clit.  I watch as my pants got tighter and tighter.  I pull down my pants and start beating my dick like it owes me money, mafia style.  She starts moaning and fingering herself.  She cums, then I cum.  Because that's the general Jeff rule, ladies first.


She gets out of my car, we exchange a few words, then she heads back to the SUV and gets in.  I'm still in shock and can't move.  I finally come to my senses and head home.  I get home around 2am, which was late as fuck because I lived with my mom at the time and my mom is the offspring of Adolf Hitler and the Wicked Witch of the West.  I creep inside (or try to), rush to my room and get into bed thinking "Wow, what in the fuck just happened? Did that really just happen?"  Feeling the sticky gooey left overs between my legs confirmed that it did.





The Blowjob Mishap Story

Posted on February 14, 2011 at 3:47 PM Comments comments (0)

Date Occurred: 1995/96

Date Written: 2011


Editors Note: When I was 16 (young, dumb, and really full of cum), I got the worst blowjob of my life...from a 13 year old. I'm writting this story only because it's funny to everyone but me, so you can laugh at my hulmiliations.


The day of my 16th birthday I was able to talk my mom into letting me get my drivers license (if you have met or know my mom, you know that talking her into anything is rather difficult). The next night my friend Michelle called me and asked if I wanted to come to her new years eve party at her house (I had to talk my mom into letting me go do this too). This was a great idea I thought and we set a time for me to arrive. I was more than excited, I was double excited as I just got my license, I'm single, and a hot single girl invited over to her party. Did I meantion her dad was cool with me crashing there for the night...with both of his hot daughters?


However, Michelle and I were just friends, strictly plutonic. She was one of those girls that you just absolutely have no sexual attraction to what so ever like they remind you of your brother/sister or cousin but cool all in the same? Yeah one of those. She was still hot though, just not my type...but her sister sure was! Before I left I took a shower, took a shit, and all the other usual 16 year old boy going out crap. On my way out the door I decided not to bring any condoms, because even though I thought her sister was hot, didn't mean that she thought I was anything remotely cute because I'm not. That move was just one of my many failures in life, go me.


I get to her house and there aren't that many people there, come to find out she either didn't invite too many people or some people weren't answering their pagers. Yes pagers, not cellphones, remember this is 1995 going into 1996. The Internet was just starting to infect random households. Facebook was a mere pipe dream at the time, as text messaging was. Those were the days!


We all had a little mini party, a sort of get together if you will. I started talking to Michelle's dad about just random shit. He was a cool guy, very mellow for the most part, at least he was around me. Turns out some months later I discover that he's a pothead. Imagine that? The closer it got to midnight, the more and more fucked up I got. Midnight came and went and I was tore up seven ways the Saturday. I don't remember how much I drank or smoked that night but it was a lot because at one point I was zoning in and out of falling asleep. Eventually, we all ended up downstairs in the basement where Michelle and her sister resided. We all talked some more and probably played some kind of crazy drunk game, but I don't remember as that was 15 years ago and I was trashed, so sue me.


More times passes and the people that were crashing, crashed. The people that were either leaving of their own free will or getting kicked out by Michelle's dad, did so. I was fortunately one of the ones that was allowed to crash until day light. Now before I continue, you may think you know where this is going, but you have no fucking idea. I didn't either, but now I wish I had.


Her dad's room was upstairs, so up the stairs he went and left just the 3 of us alone. This was great as I've just had a birthday a day before, I'm now sitting with 2 chicks with nobody else around, one in which I'm now giving fuck me eyes to, Michelle's sister. Now what happened next is kind of a blur so I'm going to peice it together the best I can here. Michelle decides it would be best to goto sleep as it's now around 2 or 3am, so off she darts to her room. Leaving me alone with her sister.


Her sister and I talk some more then start making out. Wow, here I am drunken stoned off my ass and making out with a 13 year old. Thank fuck I was only 16 at the time. We then start touching each other like 2 horny marmosets, it was awesome. I realizes where this was going and remembered something...I DIDN'T BRING ANY CONDOMS! FUCK!


Suddenly I get an idea. I will go ask Michelle for a condom! Excellent, now I can bang her sister 5 ways to Friday. What a way to bring in the new year I thought as I knocked on Michelle's door. Still drunk as a skunk, I stumble into Michelle's room. She wakes up and asks what I want. I must tell you, I was completely honest here.


Me (in a drunk 16 year old voice): I need a condom so I can fuck your sister. I left mine at home.

Michelle (half asleep in a hung over voice): Jeff, goto sleep. You don't need to fuck my sister.

Me (looking around her room in pure desparation): Michelle, I just need a condom!

Michelle: I don't have one.



Now one may think this may feel good as well it should, but there was something wrong. Something out of place as I was feeling pain around the head of dick which confused me. Though it was dark and I couldn't really see much, I was able to catch a glimpse of the most horrible thing you don't want to look at. SHE WAS USING HER TEETH! This girl did not know how to give head, at all! I'm guessing it was because she was 13 and hasn't had much practice like one of her 15 year old counterparts. She kept using her teeth and using her teeth, being shit-housed drunk to the point of the room nearly spinning 6 times over, I managed to utter the words "You're biting it!"


Yet, she kept on using her teeth. After of what seemed like a lifetime of pain, she stops sucking with her teeth and starts actually sucking the right way. This results in me cumming. However, as I'm about to cum, she pulls away and tells me to goto the bathroom. RIGHT AS I'M CUMMING ALL OVER MY FUCKING BOXERS AND SHIRT! Yeah go ahead and laugh, dickbrain.


I get to the bathroom and what I thought was over with, had only begun to surface. I look down at my cock and see yet another terrible sight. My fucking cock was bleeding! She had biten it so hard, it started to bleed! I grab some toilet paper and wipe the excess cum along with a mountain of blood off the my dick. At first, it wouldn't stop bleeding. I get water and throw it on my member, more pain comes as it burns. I wipe it off some more and somehow find band-aids to patch myself up, McGuyver style.  I get out of the bathroom and back to where the nightmare happened, only to find Michelle's sister crashed out. Great, now I can't scold for nearly going Lorena Bobbitt on me.


At this point I have no idea what time it is, but the sun is coming up and I'm the only one awake, so I decide that it's best to pass out myself, with my member looking like a mummy.


What a way to bring in the New Year. 

Drunken Neighbor Misadventures

Posted on November 19, 2010 at 3:55 PM Comments comments (0)

Date Occurred: 2005

Date Written: 2005

Date Revised: 2010


EDITORS NOTE:  This story took place while I was living in Chicago with my ex girlfriend.   It was originally called The Misadventures of the Drunken Neighbor, but I figured that was too long of a title for a story so I shortened it some.  I have revised it for content and grammar.


I came home from work one Friday morning and took a nap. I wake up sometime later and decided to watch Star Wars: Return of the Jedi.  30 minutes into the movie, my doorbell rings. Too early for the mail I thought, so I wondered who it could be. It could be my friend Kat, but she usually calls before she comes by. I answer and nobody says anything, so I answer again. This time a familiar voice is heard. It seems it's the guy that lives on the first floor (I am on the 3rd/top floor of my apartment building) and he wants to know that if I drive him to the liquor store he will give me $5. Needing money I said what the hell, okay.


Little did I know that next hour would be one of the most funniest times of my life.


He tells me to meet him outside in the parking lot in 5 minutes, so I pause the movie put some clothes on and head outside. I get to the back and I don't see him. So I wait a few minutes before going and knocking on his door. As I am about to knock he comes out and tells me that he needs 10 minutes to do something and that he will come get me when he is ready. Back upstairs I go. I continue to watch the movie as time passes on, however after about 25 minutes I finally decide that he must've forgotten or something. I then hear my doorbell ring again and it's him. I go downstairs and this time he is waiting for me. We get in my car and head to the liquor store. I noticed that he was drunk by the way he was acting.  At the liquor store he gets out and goes in. 10 to 13 minutes later he comes back with nothing and says okay let's go.  Back to the apartment building we go. As I'm walking up to my apartment, he stops me and asks if he left his beer in my car. I told him he didn't get anything. He agrees and goes into his place.


Back upstairs I unpause the movie, then I hear another knock at my door.  It's him yet again. He asks me if I am sure he didn't leave his beer in my car, again I tell him he never got anything but he can go look in my car if he wants. We go down to my car and he realizes that it's not in my car but it's still at the liquor store on the counter.  He tells me he will give me another $5 to take him back, but he wants to call and make sure it's still there first. So he goes back into his apartment and I wait around for him to come back. After about 10 minutes of waiting I go knock on his door, no answer.   He must've passed out. I then get an idea to walk around front and see if he's there. I turn the corner to see him sitting on his balcony holding a page from a phone book with his phone on the ground and the rest of the phone book torn up with pages everywhere. I try not to laugh and ask him if he is ready to go. He looks at me and asks go where? I tell him back to the liquor store. He then remembers and tells me to meet him around back again. I meet him in the parking lot and off we go the the liquor store for the 2nd time.


Back at the liquor store he gets out and walks up the the window, not the door mind you, the window!  He tries to open it as if it were the door. I laugh histarically at this. He gets inside finally and five to 8 minutes later he comes out, walks around my car twice then walks to the car next to mine, then back up to the door to the place and turns around and then finally sees me waving at him.  He gets in and we head back to the apartment building. He tells me that he doesn't have another $5 on him and asks if he can give it to me later. I said yeah sure whatever. Even though seeing him be completely shit-housed fucked-in-half was enough payment for me.


We get back to the apartment building and it takes him litterally 2 minutes to get out of my car. He finally gets out and thanks me and walks back around to his balcony. I then see my other neighbor that I hang out with at times and she motions me to come over to her car. I go tell her the that he's wasted and we just got back from the liquor store. She laughs and then starts to talk to me and asks if I want to hang out for a minute. I said sure and went up to her apartment to chill. About 10 minutes my roommate calls and asks me for something, so I leave and go outside to her car. I then tell her about my whole liquor store adventures. She leaves and I go back up stairs and finally get to watch the rest of Star Wars. What a great Friday afternoon I had, I got to watch my drunken neighbor be a shitfaced drunk. Hell like I had anything else to do right?



An Odd Night

Posted on November 19, 2010 at 2:26 PM Comments comments (0)

Date Occured: 2007

Date Written: 2007

Date Revised: 2010


Editors Note:  This is another story from my Live Journal that I wrote a few years ago.  It has to do with, and touches base on my Charlie's Days, which that story is coming.  I warn you DO NOT do anything that I did in this story.




NOTE: I changed some shit around in the below entry to protect my privacy. I also left some unimportant shit out.


After work one night I decided to go unwind and have a few drinks at the local club/stripjoint/bar. This girl I've known for awhile and haven't seen for awhile that works there (as a waitress) was all happy to see me. As the night came to a close, I waited for her to get off. She had told me she had to go pick up her friend from a club downtown after she got off prievously. I asked her what she was doing after that. She told me nothing, so I came up with a plan to follow her downtown.


Since I was drunk for the most part and stoned, and she was stoned, we ended up driving around downtown for a fucking hour looking for this club because she didn't really know where it was so we had to stop and ask 47 people how to fucking get there. Finally we find the club and it was closing, so I came up with a great idea to go back to her place.


We get back to her place and chill in the living room. We watch some videos on VH1 and smoke a doobie. Some minutes later she ends up passing out in the chair next to mine. Being horny from the weed I start to get a hard on and eventually start to stroke myself. Carrie Underwood's video comes on and I start beating it like crazy as Carrie is hot. I then realize I had nothing to cum on so I get up and hurry into the bathroom. I grab some toilet paper then head back to my seat. As the Carrie video is about to end, I stroke it like mad and look over at my friend right as I'm at orgasm. She didn't wake up at all! Of course I wasn't loud about it either as I can "stealth" wank with ease.


Posted on November 19, 2010 at 2:03 PM Comments comments (0)

Date Occured: 2006

Date Written: 2006

Date Revised: 2010


EDITORS NOTE:  This is an old story I wrote back in 2006 just a few months after I moved to here to Birmingham.  I have revised it for grammar, nothing else.  The full unrevised version can be found here: .  This story was written BEFORE I even knew Tucker Max (the guy that inspired me to write again) even existed.


I was chatting online to my girlfriend at the time and she tells me that she will be going out for the night and won't be back until Saturday. So I figured I'd work until about 7pm or 8pm and get off. Well this doesn't happen due to us being hella busy. I get off work around 10pm and head to my hang out...the local tattoo shop!


Upon entering a friend of mine tells me that he has something for me and whips out some pot.  This excites me. I go inside and was greeted by shits of loads of people. I quickly say hi to everyone and then roll one up and spark it. While doing so, this other guy (we will just call him T) decides he needs to make a beer run. This excites me more so I decide to tag along.  We get in his fast as fuck Honda and take off.  At the gas station we (which was about 2 miles away) blasted AC/DC Highway to Hell in which we listen to on the way there. Nothing really exciting happens next so I'll skip ahead to when we first get back to the tat shop. I come back with a 12 pack of beer and put the beer in the fridge but not before helping myself to one.  I go back outside to see 2 of my friends (who are girls) groping each other. So what do I do? Go get my camera of course!


Upon returning from snatching my camera, I snap a few pics of them, the other guys, the FoozeBall table, and myself. I can't wait to get those developed. T took the camera at one point too, no telling what he took. Anyway, several more beers and joints later we finally decide to head back to my one buddies house. 4 cars deep we jet onto the highway.  My buddy has an Acura, T had some really fast Honda (I don't do cars really), this other dude that knows my buddy had some sporty looking car I didn't catch the make, and me well I had a Saturn LS2. On the highway my buddy is ahead with T behind me and the other dude (I will call him V) behind him. I almost get in front of my buddy when I get stuck behind a semi.  FUCK! Oh well, we aren't really racing at this point so it doesn't matter. We all get off the highway and everyone is blasting their stereo except maybe for V because he's an older type dude. My buddy has as system and so did T, so my factory made stereo was flushed out.


Four roads and several turns later we hit the road that leads to my buddy's house. Here's the formation now as follows (remember this because at the end I too was like WHOA what the fuck!?): My buddy in front, T behind him, me, V behind me. We turn down the road and my buddy and T take off, I kept trying to keep up in my piece of shit car going 60mph in a 35mph but I couldn't. Oh and let me add that this is a 2 lane road, one side goes one way the other side the opposite way. As I'm trying to keep up I don't see anyone in front of me or in back of me. I speed up to see brake lights in the distance. Upon turning onto my buddys street I see everyone has slowed down, but as we pull into his driveway I notice my buddy in front of me. I park my car , get out and T is already talking to my buddy. He said he fucking Dukes of Hazard'ed it over this one hill. My buddy confirmed this as he saw it all. I missed it due to my car being slow as a sloth and my careful stoned driving.




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