The first/last time I had sex in a car

It’s finally summer time! Time for summer vacations, summer parties and summer flings! I have a lot of good memories during the summer. A few funny and uncomfortable ones as well. Like the first time I had sex in a car. Must of been summer of 2011. I just turned 21 and got my driver license. I was hype! Told myself I’m never taking public transportation again. Now that I had a license to drive, I was able to pick up my friends whenever and say “let’s go out!” and we could really make moves. So that summer I started to “find myself”. Started dressing up differently, had a lot of money in my pocket and was ready to do things differently than I used to. I didn’t even think how that would catch certain girls eyes because I was too busy living my best life. Now at the time, living in my old building I had a huge crush on a girl who lived 3 floors above me. Since forever I had a crush on this girl and for maybe a year I been telling this same girl about her. Let’s call her “Cheryl”. Now Cheryl I knew for at least 7 years up to the point. We went to high school together, we shared a few friends and recently at that time got reacquainted. She was the homie so I told her about every girl that caught my eye. So one day, I’m walking in my old neighborhood and I’m feeling myself. Got money in my pocket, got brand new clothes and I was writing a new movie I thought I would be filming soon so I was feeling like the man, like jack screaming “I’m on top of the world!” As I’m walking home, I see my crush walking my direction. All these thoughts were running through my mind. Do I say something? Do I say hi and keep it pushing? Do I ignore her? Before I can rationalize these thoughts, she was already 3 feet away from me.  “Hey you” I tell her as she locks eyes on me. She smiles back “Hey!”. In my mind I’m lost for words cause I never even thought I would have the courage to talk to her. I ask her “Do you remember me? When we was younger we (referring to my siblings) used to play with you and your brother at the park”. She laughs “of course I remember!”. So here we are, both smiling like idiots. I pass her my phone and tell her “give me your number, we gotta catch up”. She puts in her number immediately. When I say I felt like I upgraded to another level of life.... mannnnnnnnnn I was on a whole new high!!! So I text Cheryl cause at the time she was the only one who I talked to about girls I was really interested in and the last time I spoke to her, she made fun of me saying I would not only not talk to my crush but I also wouldn’t get her number. I text “Guess who just spoke to his crush and got her number.... this guy!”

She lol and congratulated me but something felt off. I paid no mind to it cause I was too excited about getting my crush number. We started texting that night but I wanted to play it cool so I held myself back from reaching out to her back to back.  Randomly the next day Cheryl text me and ask me to pull up to her place. She ask me to bring my car and a bottle over and we can play some card games. Now because Cheryl and I always met up with a bottles, some card games and friends I thought nothing of it until she told me it would just be us two. Still thought nothing of it even when she asked me would we be able to push the back seats down (at the time I was driving my mother Chevy suburban). It wasn’t until I sparked up with one of my boys I figured we wasn’t just going to drink and play card games. When I told my boy my plans, he laughed in my face. He said “Bro, y’all bout to have sex”. I’m like “What? Na!” in total disbelief. She’s the homie. We’re not even like that. Now my crush was cute but this girl was gorgeous. She didn’t even need make up to amplify her beauty. She was humble, funny and had a great sense of fashion. She was a very slim/petite woman with long Curley hair, her butt wasn’t huge but it had a cute jiggle and double Ds I couldn’t take my eyes off from but she was still the homie. A few other friends join the cypher, mostly girls and when they hear the story, they all agree.. “yeah you’re about to have sex!”.  Me being naive, I tell them they don’t know what they are talking about. I get ready to leave and I get word from my moms I won’t be able to use her car for the night. So I call up Cheryl to tell her and she goes “it’s okay, we’ll just hang in my dads car”.  Now the alarm starts going off in my head. “Wow, she really wants to spend time with me tonight? She never so persistent in seeing me... maybe she’s going through something and just want to talk.. fuck it.. just in case... I should bring a condom”. So I get to her place, she walks out and we both quietly entered the back seat of her fathers car. It got really dark really fast to the point I was only able to see her with the street light above us. We were drinking pinnacle vodka, straight no chaser. Taking shots after shots. I don’t even think we ever got to play any card games. I just remember we had that right amount of drinks and the right amount of laughs before it got real quiet. She tells she’s cold, so I wrap my arms around her. She lays her head on my chest and we laid there for about a minute. Without hesitation we found ourselves kissing. At first it was an innocent kiss... but then we couldn’t stop. Eventually she turns around and wraps her arms around my neck. I started pulling her closer and closer as we continue to make our heavy. She tries to wrap her legs around me but there was no fucking space in the back of her fathers Honda Civic. She then looks me in the eye and ask “Do you have a condom?”. Feeling smart about having one with me, I pull it out instantly. I help her take off her pants and noticed immediately she wasn’t wearing any panties. It was that moment I realize how naive I really was and the fact that women know they are going to (or not going to) sleep with you before they even step foot out the house. I try to take off my jeans and put on my condom but I couldn’t get my jeans past my knees because there was enough space to take off my pants completely. She didn’t care. Once the condom was on, she just started riding. Now I’m in complete disbelief. Never in my right mind would I ever imagine Cheryl riding me in the back seat of her fathers car. A man I never met.

So we’re doing it in the backseat of her fathers car and everything was going so well until she started crying. She completely stops riding and just starts crying with me still in her! She gets up off me and goes into the corner of the car and continues to cry. Now here I am, drunk, with my pants up to my knees, dick out, my naked cold ass on these leather seats, condom still on, feeling awkward in the tight space of a car of a man I never met. I didn’t know what to do so I did what felt right. I held her and played with her hair until she calmed down. She eventually would tell me it was the first time she done it in a while and she wanted to do it with someone she trusted. She’s been heart broken by her ex so she had a hard time dealing with other men but once she heard I was finally talking to my crush, she just wanted me for herself. I thought that would be the last time we would have sex but it continued with the following week after leaving the bar and taking the train/Van back (and I ran home in 15 mins instead of walking the usual 30 to get the car while she was still in the mood). We begin to have sex in cars alot. We had sex in the car after she saw the best man holiday, after leaving her best friends party but the last time we did it in a car, it was the last time we had sex period. Literally this time, last year. At this time we were trying to date but it wasn’t working out. She had a heavy case of FOMO and my dumbass looked through her phone and found out she was talking to other guys after she left her phone in my car. So I decided to give her some space and wanted to go our separate ways. We had break up sex at my place the day I saw the messages and I thought that was the end of it, but she calls me one night and tells me she wants to talk things out. I was packing up to leave and  shoot the first episode of my travel series in Fishkill New York but I said fuck, I’ll stop by one more time. She ask me to bring some weed so we can smoke as we talk. I get there and her dad was asleep in the backyard so we went back to my car instead lol. I had no intentions of having sex that night. Maybe it was the weed, maybe it was the back to back R&B songs, that right summer night  heat and breeze but something came over us that night. In between spliff and songs, we found ourselves all over each other one last time. We made love plenty of times since the first night in her dads car, especially when I moved into a new apartment and she would spend the night but this time, we wasn’t making love. We was fucking. That car was rocking like we were in the middle of an earthquake. We went round for round until we was out of breath and covered in sweat. Looking at each other in disbelief. It was supposed to be over but here we were doing it again. Nothing ever came out of it. We eventually went our separate ways and never spoke again.. but when someone asks me “hey, you ever did it in a car before?”.. I begin to think of those summer nights.