Unhealthy Rebound Sex

I was taking a recent break up pretty badly… spending a few days in my bedroom drinking beer, binge watching the first three seasons of Scrubs and feeling sorry for myself. Unlike previous bouts of self-loathing after a break up, I found myself completely uninterested in sex. Or companionship. Or any sort of interaction with anyone. I spent these weeks writing terribly derivative and attention-seeking blog posts about how unlovable I am. How I’d never find someone. I was fucking 23 and stupid and emotionally immature and thought that I could make my ex feel sorry enough for me to take me back. Don’t ever do this.

My self-involved diatribes didn’t cause her to fall in love with me and come running back… but they definitely caught the attention of Nikki. I’d never met Nikki in real life. She had done some freelance writing for me the previous year and we were connected on Myspace and Livejournal, but we rarely talked… until my blog posts were plagiarized My Chemical Romance lyrics, changed to vaguely reflect my sadness.

Her approach was very blunt… a public post on my Myspace wall stating simply, “Hey – we should hook up.” It was the early 2000’s and I was oblivious to the meaning of “hooking up,” so I replied with a simple message asking if she’d like to get some pizza and hang out sometime. Her response was more aggressive, “I guess, whatever, but I want to make out with you.” After making it extremely clear that neither of us were interested in more than physical fun, we agreed that I’d pick her up at midnight.

Nikki lived two hours away. This would prove a major annoyance, a source of comfort, and some awkward interactions when I moved to the area a few years later. I was a few minutes early when I pulled up to her driveway. She texted me and told me to park around the block – she still lived at home and her dad was a really strict republican. HUGE red flags, but I was already $35 worth of Bush-era gasoline and two hours into this adventure.

At 12:01, Nikki hopped into my car and told me that we should go find a cemetery. Owing to her comments about her dad, I was scared she might be lying about her age, so I awkwardly carded her, confirming that she was 19, and covering up my concerns with a teasing joke about how I guess I wouldn’t be buying her a drink that night. She responded by leaning across and licking my neck and telling me which way to drive.

We drove for about 20 minutes before finding a cemetery. At the time, I was driving a 1990 Buick with bench seats, so Nikki moved to the center of the seat and began rubbing my cock over my jeans. This was the height of the Myspace Scene kid era and I was already hard, so while the efforts were appreciated, the sensation was uncomfortable, so I unzipped my pants and pulled my erection through my pants.

Nikki immediately spit on my cock and started working me with her hand. She was inexperienced, so I told her that I liked it slow… so she slowly stroked my cock until we pulled into the cemetery parking lot, then leaning over to lick me awkwardly from base to tip for a few minutes.

Author’s plea to automakers: Please bring back bench seats. Author’s plea to persons interested in learning how to give good oral: Watch my wife blow me. 

What Nikki lacked in experience and skill, she made up for in willingness and enthusiasm. We walked through the cemetery looking for a secluded area to fool around, finally sitting up against a mausoleum wall. Nikki crawled on top of me and started aggressively kissing me.

For the people who need a bit of a visual, Nikki was very short, maybe 4’11” and thin with tiny breasts and a small bubble butt. She was naturally a redhead, but very self-conscious about it and dyed her hair black. She wore heavy makeup to conceal some of her freckles. That night, she was wearing a tight skirt and a hoodie.

As we made out against the mausoleum wall while she grinded against me in my jeans. Again owing to the tight jeans, this became uncomfortable and I wanted to make this girl cum. Reaching under her skirt, I found that she’d conveniently forgotten to wear underwear that night and that she was absolutely soaked. I slid my middle and index fingers into her while working her clit with my thumb.

Unfortunately, Nikki had a hard time keeping quiet and we were busted by a security guard before I was able to get her off and we had to run, her skirt rolled up over her ass as we ran to my car. I was simultaneously extremely horny and couldn’t stop laughing as we pulled away.

We were in rural Pennsylvania, two hours from my apartment and her parents made going back to her place impossible. I suggested that we just park somewhere and fuck in my backseat, but Nikki didn’t seem into it. She suggested finding an abandoned building. I was game… but we never found a place and ended up doing the next best thing – I shelled out $45 for a shitty hotel room.

We checked in at the front desk, our intentions obvious to the elderly man working the front desk, who missed my less than discreet attempts put my hand up Nikki’s skirt and rub her clit right just feet away. When we got to the room, she wanted to shower, so I walked to my car and picked up a case of beer I’d brought, put it on ice, and shotgunned two bottles while waiting for her.

I was probably overthinking things, but since she took the time to shower, I decided that I should do the same. Nikki came walking out of the bathroom, wrapped in a towel, grabbed a beer (which I still think about to this day – she was 19), and laid on the bed. I excused myself, taking two beers with me because shower beers rule, and proceeded to take one of the fastest showers ever.

I walked out of the shower, wrapped in a towel, and the sight in front of me made my jaw drop. Nikki was completely naked, rubbing her breasts with one hand, while working the neck of a beer bottle in and out of her pussy. I dropped my towel and walked over to her, trying to not be noticed as she fucked herself, then I grabbed the beer bottle.

I maneuvered myself between her legs and took the beer bottle, continuing the job she had started earlier. She was pinching her nipples and writhing, while repeating, “don’t stop. don’t fucking stop.” I doubled down on my efforts and began working her clit with my tongue while continuing to pump her pussy with the beer bottle. As she started to cum, I slid a finger up her ass. She was done. My face and hands were soaked. The sheets were soaked. The room smelled like an orgy. That was fun really fun, though I had yet to cum.

That happened the next day.

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