I never dated or held a job during high school; my teenage years kind of snuck up on me and before I knew it I had graduated and was working my first job at the local movie theater. This is also where I met my first girlfriend. I felt very inexperienced so I let her make all the first moves. We were making out on her couch at home and she moved my hand down from her shoulder to her tit, which surprised me enough I exclaimed “Oh my God!” She just giggled, and things rapidly snowballed from there; I lost my virginity within the first week of dating her. She was far more willing to let me take off her bottoms than her top, which annoyed me, but hey, first pussy! I wasn’t too upset given the circumstances.
During those long, late night teenage phone conversations she had told me she preferred it when the man took charge, sexually. She wished I was more experienced than her, not less. However, I was a virgin and she was not, so I expected HER to take the lead and told her as much. So one night she and I were in her bedroom (with the door open to keep us from fooling around, for all the good that did!) and I was on top of her, kissing her. She reached under the pillow and produced a condom. We’d been talking about having sex so I wasn’t surprised. I rolled it onto my cock and got between her spread legs… and I couldn’t get it in!
The angle was just wrong and although I knew textbook female anatomy, the real world application was something else entirely. The reduced sensation from the condom probably didn’t help either. So after a few awkward attempts we gave up for the moment and went back to kissing and talking, albeit naked with the condom still on. About ten minutes later she said, “Ray?” “Yeah?” “Make love to me.” “Now?” “Now.” “Get on top of me.” And now that she finally took control, things went smoothly. She guided me into her pussy and slid down my cock, and I remember thinking at that moment, “Wow, I’m not a virgin anymore.”
The sensation was unusual, I’ve never experienced anything quite like it even afterwards; it was like all of the sensation was focused entirely on the ring of her vaginal entrance slowly sliding down my cock, almost like a cock ring. When she hit bottom she gave me a lustful look and asked if it felt anything like I expected. I breathlessly told her no, it wasn’t at all how I expected it to feel. We proceeded to make love, slowly and quietly so as to not get caught. Neither of us came, in fact neither of us came at all during that entire 6 month relationship! With 17 years of hindsight, I strongly suspect she didn’t really WANT to have sex so much as she did it because “that’s what boyfriends and girlfriends do.”
I know she felt a bit guilty for losing her virginity at 14, had yet to experience an orgasm, and probably had some issues with sex. I just wanted her to take the lead and teach me, she wanted the man to take charge so she could be swept up in it, and as a result we sort of fumbled around the whole relationship, sort of flying blind. If I had it to do over again I probably would have lost it to my second girlfriend, who was much more sexually assertive and would’ve ENJOYED “breaking me in.”
Ironically, it was after that that I gained enough confidence to take control in the bedroom, be rough if that’s what she wanted, and learn to FUCK instead of “making love.” So my takeaway is, don’t be in such a rush to lose your V-card that it prevents you from actually enjoying it.
- Name: Ray
- Gender: Male
- Age of Virginity Loss: 19
- Current Age: 36
- How would you categorize your story?: Regret
- Country: USA
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