The Loser Jeff Stories

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

My Stories

The "I'm a Prostitute" Story

Posted on April 17, 2011 at 2:35 PM

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.





Categories: None

Post a Comment


Oops, you forgot something.


The words you entered did not match the given text. Please try again.

You must be a member to comment on this page. Sign In or Register


Reply Anon
9:14 AM on April 20, 2011 
oops wrong thing. anyway lmao youre a liar thats not your rule you always go first
Reply Jeff Stoney
1:37 PM on April 20, 2011 
Anon says...
oops wrong thing. anyway lmao youre a liar thats not your rule you always go first

Really now? You know this for a fact? You must be one of the girls I banged when I was drunk, came, and then passed out before you could. Sorry about that!

Recent Videos

1463 views - 0 comments