Jack

I grew up in Austin, Texas, but when my mom remarried when I was around 25 she moved to the Ft. Worth area. Visiting her is nice, but I hardly know anyone there so I get pretty bored during a long visit. That’s where Tinder and Bumble come in handy. I debated whether or not I wanted to swipe right on Bumble on Jack for a minute before ultimately saying “fuck it” and going for it. We were a match, and since Bumble requires the woman to make the first move I went ahead and sent a pretty generic “hey how’s it going” message, and he responded almost right away. It turns out Jack was also visiting his family and just as bored as I was on a Monday evening, and after maybe a few minutes of conversation we decided we both needed to get out of the house and get a drink.

 

Jack wasn’t exactly my type, I’m not usually into bald guys, but he had a great smile, had the whole cute Italian thing going for him, and he looked like fun, so I was game. I met Jack at a bar not too far from my mom’s house, close to Texas Christian University campus (oh the irony), and he greeted me with a huge smile and hug. I could tell he had a good energy about him as we started to talk and get to know each other. Jack was a professor at a pretty well-renowned university who would be spending a few months writing his first book this winter, so we shared war stories of the writing process, and commiserated over the struggles of writer’s block. I told Jack all about my Instagram and my blog and he was enthralled with my dating stories.

 

“I’m gonna do what it takes to make the blog,” Jack said with a smirk.

 

I wasn’t sure if he meant he’d do something terribly embarrassing or if he meant he was going to blow my mind, but either way I was excited to find out.

 

We decided the bar we were at was a little too dead so we needed a change of scenery, so after one beer we hopped in the car to find a more lively spot. After cruising around for a little while, laughing and realizing more and more that we were both total insane people, we pulled up to a dive bar that I can’t remember the name of and parked across the street. It was Monday, so everywhere was pretty dead, with nobody walking around, and before we got out of the car Jack said “I need to kiss you first.” We made out in the car like teenagers for a few minutes, and I knew the rest of the night was going to be fun.

 

Once we finally stopped acting like we were 16 and on a date to the movies, we went into the dive bar and had a couple more drinks. I almost never wear a bra or panties, and this night was no exception. Jack noticed and ran his hand up my inner thigh under my dress, right there at the bar. I tossed back the rest of my drink, looked at him and bit my lip. He smiled, leaned in to kiss me, and kept going with his fingers, teasing me under my dress, and then asked the bartender for his check. It was most definitely time to go.

 

We hurried to the car where we got in and realized, oh shit. We are BOTH staying with our parents right now. Jack was driving his dad’s car, and we couldn’t go back to either of our places, so we had to improvise. Jack drove to a dark parking lot nearby and we crawled into the back seat. It was only at this point that I noticed that the radio had been on this late 90s alt rock station, which only added to the high school nostalgia of the entire thing. Jack and I started going at it, aggressively making out, and he laid me down and pushed up my dress and started devouring me like I was his last meal. It was so hot, and just as I thought I’d cum soon he ripped off his shorts, revealing quite an impressive package and he slid in. He was just the right amount of rough, pulling my hair, lightly choking me and pretty much fucking my brains out. I came hard and as soon as I did, so did he, without missing a beat or even pulling out. While I realize getting cream pied on a first date isn’t exactly the smartest or safest thing I’ve ever done, it was so fucking hot I didn’t care.

 

Hoe tip: if you’re gonna make reckless decisions, at least make sure they’re fucking fun.

 

The windows of Jack’s dad’s Honda Accord were fogged up, R.E.M.’s “Losing My Religion” was on the radio, and I was getting railed out in a back seat in a dark old parking lot. If that doesn’t bring back some teenaged memories, I don’t know what does. We fucked a couple more times (shout out to Jack for having outstanding stamina), and then decided it was getting late and we needed to get home. Jack drove me back to my mom’s house, which just so happened to be in the same neighborhood his parents lived in. We pulled up to my mom’s house, Jack kissed me one more time, and as I got out of the car I said “oh, you made the blog.”

 

Jack drove off, and I snuck back into my mom’s house with cum dripping down my inner thigh, really rounding out my trip down memory lane. I hopped in the shower, and laughed at myself the entire time in there, grabbed some water when I got out and crashed. Jack and I are still in touch, and I’m sure we’ll see each other sometime when we’re both home for the holidays. Can’t wait to make another mess in the back seat of his dad’s Honda Accord.