NOT Your Grandma's Book of Progressive Erotica: Vol 6

Tight Mess

Since moving back home, I hadn't been on a single date, so I was beginning to get in touch with old flings and even some friends who I hadn't talked to in a while. One of my friends that I grew up with on my street happened to be out jogging the one day I was washing my car, so I stopped her. At first she didn't recognize me, but once she did, she gave me a hug and suggested that we go for coffee that night.

I drove over to her house after dinner and she came out in sweats before I even had a chance to get out to ring the doorbell. She brought me up to speed on how things had changed when I was away out west. Of all the things she told me, not a lot surprised me. She had dated a friend of ours and after a few months found out he was quite the douchebag. We laughed at him together as we pulled into the drive-thru and ordered our drinks.

We drove around the city until we came to a park that we used to frequent when we were younger. Drug dealers used to use the parking lot, but that hadn't happened since we were young teenagers. The chance of cops bothering us as we drank coffee was slim to none. We continued to talk about the past, what I did out west and what she was currently doing for work. Eventually we got to asking each other about dating again and it snowballed into her asking me if I liked her.

"Have you ever thought about dating me?" she asked.

"Well," I began, "I don't know. We grew up together, so my mom and dad might find that weird, or perhaps cute – they're strange like that."

She laughed and then put her hand on my thigh. Glancing at the back seat, I knew what she was trying to point out to me. Whether we dated or not, she needed a good lay and so did I. We hopped in the back seat over the center console and began making out like crazy as we pulled our shirts off one another.

I never really got to check her out prior to that day and it showed when I was genuinely surprised by her nice round breasts as they were held up in her bra. Even when I stopped her when she was jogging, I didn't take much notice of her breasts when they were in a sports bra. She undid her bra and then I saw just how nice her nipples were as well. Her face was cute, but her body was looked phenomenal. She must have been taking really good care of herself since I left by the look of things.

The last thing for each of us to come off were our pants. Her sweat pants came off quickly and then I saw that she wasn't even wearing any panties. Clearly she had decided well before the date that we were having sex since I had never met a girl who once went commando.

Caressing her breasts as she went down on me, I laid awkwardly in the back seat of my car. It wasn't going to be the most comfortable experience, but it would be the first time I ever tried it. Her mouth and tongue felt really good on my cock and I couldn't wait to fuck her pussy. With that thought in mind, I then reached for it and began to rub it as she seemed to be nearing the end of my blowjob.

She slid forward and I did my best to spread out on the back seat so she could ride me. Adjusting several times, she then slid down onto my cock and began to rock back and forth on it. Her pussy felt so good that it made me wonder why I hadn't thought about dating her prior to that moment.

Riding me for some time, I started to get a cramp, so I sat up in the middle of the seat as she tried both forward and reverse fucking while trying not to hit her head on the headliner. Near the end before her orgasm, she was leaning on me so hard that the seatbelt was digging into my back. It really hurt, but I didn't want to ruin the moment if she was about to cum. Once she did, I had her lay on her back and pounded her pussy until I was ready to cum as well.

I pulled my cock out of her pussy and then tried to get to her mouth in time, but I tripped over the hump of the car and shot my jizz all over the side of her face and the seat instead.