Where it happened: My car
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Well, my first time wasn’t exactly how I imagined. I was 16 and dating this girl for about two months and it wasn’t easy to get her either. She was still hung up on her ex and she was kind of wishy-washy with her feelings toward me. I ended up saying that I loved her first and then we decided to date. One morning when I picked her up (a couple weeks after I had received my first blowjob) we decided that we would have sex the next day. She wasn’t a virgin, I was; however, I had experience with fingering a girl my freshman year. Anyways, I picked her up around 4:30 am before school on a Wednesday and boy was it awkward. She got in the back and got ready and I just sort of stared at the condom. I felt confident because she really enjoyed my hands, but was still a bit scared because I didn’t know about my penis. So I climbed in the back after she was ready and wouldn’t you know it, I couldn’t get hard. So I just pushed him in and it seemed to work, cuz I got one massive erection. My virginity was gone and it was awkward. She was happy and told me to start moving. Lots of fumbling, and being in a car was not a good idea. God, it sucked for me haha. I’ll admit that she was tight for doing it with one of her ex’s a lot, but I didn’t cum. But one magical thing happened: suddenly she tightened up a lot and dug her nails into my back (holy shit it hurt) and she moaned really loud. I was just kinda thinking and asked if she came. Apparently, it was her first time cumming by someone else. I was pretty damn proud, but it was about 6:50 and school started at 7:20… So we had to cut it short.
We only did it another time around Christmas (I still never came cuz a drunk dude cock-blocked us in the park and we hightailed it outta there), and then I broke up with her. I felt like a jerk, but she started smothering me and I just wanted to be single again – I’m too young to be having sex anyways. She’s dating some dude she picked up a few weeks later, so I think she’s happy (though he looks a bit like me :- ).
I didn’t have the greatest experience, but making a girl cum with my mouth, hands, and member made me feel pretty confident. I like being single.
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