This was during my time in college, so it has been a while, but I still remember this quite well. A little background: Anne and I became friends our second to last semester. She was cute, but had a boyfriend, so I never really tried to flirt or anything like that. One day when we were checking out our midterm grades (same course), we decide to have lunch, where she confessed that she really liked me and that things weren’t going to well with her boyfriend. I comforted her as best as I could without crossing boundaries. We started talking more, texting, flirting, etc. It was hard not to ask her out, but she needed to take care of things on her end.
Eventually, I broke down and asked her to go to the movies with me after finals. She agreed and the day before, she breaks up with her boyfriend. The day of, I meet her on campus with a huge smile on my face. We hug and go to the movie theater.
Sexy stuff starts here ********
The movie starts, and I wrap my arm around her. She leans into me and I am thinking of quickly kissing her on the cheek, but she turns her face towards me and we start making out. I decide to press my luck and start fondling her boobs. We put a coat over us and she starts guiding my hand lower. At this point, I am rubbing her thighs and crotch over her jeans, my lips on hers. I could feel warmth coming from her crotch and this, along with her soft lips were really turning me on.
At this point, she is rubbing my crotch and undoing the zipper on my jeans. She succeeds and all of a sudden, her warm hand is on my cock. She wraps her hand around the shaft, with her thumb on the tip. She moves her hand up and down and it felt amazing. I decide to return the favor and undo her jeans as well. I stick my hand under her panties and she is soaking wet. I play with her clit, dragging my fingers lower until they are inside of her. She is moaning in my mouth as we continue making out. For the rest of the movie, she is playing with my cock, while I am fingering her and playing with her clit. I don’t cum, but she does several times before the movie ends.
We leave the movie theater and I offer to driver her home. On the way there, we talk about what just happened and what it means for us. We are still horny and would like to continue fooling around, but she lives with her parents. No problem, we find a neighborhood near her. I park in a secluded spot and we get in the back seat (SUV, so I drop the seats to give us more space). We start making out again, this time more aggressively. Since we are now alone, we don’t have to cover up. In no time at all, we are both naked in the back of my car. She is absolutely gorgeous and soaking wet. We were both virgins, so we didn’t have sex, but we continued making out and playing with each other. Her hand felt so good on my cock and her swollen pussy felt amazing under my fingers. My mouth alternated between her lips, neck, boobs and nipples, and my fingers between fingering her and playing with her clit. I was super nervous, so I still couldn’t cum. She came a couple of times in my back seat.
Eventually, we got dressed and got back in the front seat. I driver her home and she suggested we watch a movie. It was getting late, but I didn’t have anything going on, so I agreed. We went in, sat on her couch and started watching a movie. Her mom was around, but eventually she went to bed. Once we were sure she was asleep, we started making out again. Like in the car, our clothes came off pretty quickly; this time, I got on top of her, my cock near her boobs. With one hand, I was fondling her boobs, with the other, fingering her. Her hands were on my chest and cock, jacking me off. I made her cum a couple more times, and this time, I couldn’t hold it in. I came all over her boobs and neck. It was so hot to see her covered in my cum like that. She looked at herself and was surprised. She said that next time, she will take me in her mouth so that clean-up is easier. I helped her clean up, we got dressed, kissed once more. I then went back home, happy in the thought of getting a girlfriend.
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Source: reddit.com/r/gonewildstories/comments/b3giuj/my_best_first_date_ever_long
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