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The Careless One Night Stand Chronicles

Part one: The good, the bad, and the whiskey dick...

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This wasn't my first time riding in the one night stand rodeo, don't fret, I'll get to that story another time. I was currently working for a sports bar where our uniforms resembled busty lumberjacks. I had started talking to my ex-boyfriends best friend via Snapchat. I know what you're thinking, “What did he do to deserve that?" “That's fucked up", or my personal favorite, “You must be fucking heartless". Just a friendly reminder, you are reading The Careless One Night Stand Chronicles.

I didn't hate my ex-boyfriend, this wasn't a plotted revenge scheme, and no, he never did find out. Back to the story, my ex-boyfriends best friend came to visit me while I was working at said sports bar. To keep his confidentiality, we'll just call him Luigi. (Fitting since he is about 75% Italian). Luigi arrived to the bar with his buddy and sat in my section. I grabbed them a couple beers and we chatted over the next few hours.

After awhile his buddy got his bill and left, due to “work in the morning", and Luigi had asked me if I wanted to grab a drink after my shift ended. I accepted his drink offer thinking nothing of it. We decided to take our venture to a nearby dive bar where he proceeded to buy my tequila screw drivers. I faintly remember our conversations circling music and relationships, when the “Last Call" announcement was made.

I distinctly remember having this truly profound idea that we go back to my place and keep drinking. I had a stocked liquor cabinet and a fridge full of beer. Luigi, of course, agreed with zero hesitation. We got into my Jeep and embarked on our journey to my flat on the other side of town. We poured another round of drinks and I showed him around my 2-bedroom, first-floor flat. I sat across from him at my dining room table as we continued speaking about music. Luigi was a hippy at heart and a part-time DJ.

We are very different people. He enjoyed EDM, hallucinogens, and techno. I hate electronic music, hallucinogens, and anything that is tie dye. I truly don't think I was attracted to him to begin with. After I got up to pour another drink, Luigi asked me to sit closer to him. I had hesitated for a millisecond before I took the seat next to him. I was mid song change when I noticed Luigi's hand lightly rubbing my freshly shaved legs.

In complete shock, I questioned his long friendship with my ex. He charmingly explained to me how they had drifted in their friendship and how it would be our secret, if anything should happen. I remember staring into his hazel eyes, at the time they seemed to sparkle so innocently. I quickly snapped out of his vamp glare and he, gently, pulled me right back in. The more inebriated we got, the more I didn't mind his hands grazing my body to the vibe of the music.

It was at this point of the night that I had stripped down to my bra, thong, and socks. I was “Tom Cruise sliding" on my hardwood floors. Being as intoxicated as we were that night, fucking was the last thought that crossed my mind. Luigi spun my body to face him, his hand grazing my face, edging towards the back of my neck. I stared up into his melty, milk chocolate eyes as he drew my lips to his. Fuck. We were kissing.

His mouth fit so nicely against mine, like mouths do when you're that fucked up. The more we kissed, the more aggressive it became. That kind of making out where you just say “fuck breathing, I want you". Hands were grabbing lower backs, gripping ass, and pulling hair. Yes, it was as sensational as it sounds.

Eventually, we managed to make it to my bedroom. Clothes were coming off, drinks were being spilled. I shyly receeded under the covers, as did Luigi. There we were, naked and fucking hammered. Still making out, still turned on as fuck. Let me tell you the problem here, like many men in their 20s, Luigi doesn't know how to handle his fucking alcohol.

Yep, you guessed it, whiskey dick. As a women there is nothing more uncomfortable, than a man trying to shove their soft cock inside you. For those of you who think that whiskey dick is a myth, I hope you never have to experience a, putty-like, malleable penis inside you.

Luigi and I finally decided to give up on fucking, unfortunately, the moment had passed for me about 20 minutes before this. We fell asleep around 6:00 am and woke up around 9:00 am. I had to be at work at 10:30 am. We were clearly still in our drunk and stupor because I decided to quit my only job that morning. You didn't think it could get any better, did you?

I drove Luigi back to his car around the time I was supposed to be at work. As soon as I got home, I started drinking again. We texted back and forth that day and decided we should hangout again that night. Luigi showed up around 7:30, a case of beer in hand to replace the one we had finished last night. Round two, fast forward we're naked again. We have not learned from our mistakes folks.

I tried so hard to stiffen up his wet noodle. I spent more time on a handjob that night, than I've ever spent in my entire life. We decided to call it quits once again and just go to sleep, again. The next morning, I'm thinking this guy must have erectile dysfunction. There’s no way this shit happens twice. Oh people, it does.

Luigi finally leaves my flat and we text back and forth once more. Luigi insisted on coming over again, for the third night. He thinks it will be worth it, something about “redeeming” himself and showing me that his cock works, and that it works well. I can’t stand the temptation, so of course, I agree. This is the third night Luigi came to my place, the third night of binge drinking, and the final night I would be attempting to fuck him.

I’ve been drinking all day, what else do you do when you’re unemployed with a stocked liquor cabinet? Luigi arrives, once again, I notice him pacing himself. He maybe had three drinks that night, while I had around eight or nine. Fast forward to the bedroom, finally. I had almost forgotten what a hard dick felt like.

Long story short, we fucked. As I vaguely remember, it wasn’t that great. It felt similar to fucking the guy you had a crush on in middle school. You really wanted it, but it never met your expectations. To be fair though, I was belligerent beyond belief. What else is new?

Here is the best part: I told all my friends the reason I was not working anymore, (I was unemployed for about two weeks), was so that I could have a 3-day, sex fueled rendezvous with my ex-boyfriends best friend. Yes my friends, I really did quit my job to get laid.

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