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In an actual relationship that wasn’t just a crush? I’d say 14. I may have still been 13, can’t remember. I was a freshman. No major serious relationships until I was 16, and even those weren’t awesome. But after lots of flings I swore off men except for flirting until I met my husband.
Kissed a couple girls when I was 14. Went out with a girl for a couple months when I was 17 and in the 11th grade. She was never my girlfriend. We fooled around a few times, everything but sex. My best friend gave me a condom when her and I first started talking. It may have been a month later, when we first fooled around, and I had lost the condom somewhere in between. So we didn't have sex, but did pretty much everything else.
Made out with a few girls in between 17 and 20, had a few dates, nothing else. Then started hooking up with a girl at 20, lost my virginity to her. She wasn't my girlfriend, either. Just 2 months after that, I started going out with another girl and we became official after about 2.5/3 weeks and 5-ish dates? Maybe 6? That was my first girlfriend, and we went out for over 5 years.
16 was my first real relationship. Lasted 1 year which is a long time for that age. She is the only person in my history of GFs that I am not on good terms with.
Girl held my hand at 14 once. Went to junior prom at 16. Nothing more till I turned 20. Horrible experience, pretty much ruined any chance at a normal life. Life isn't horrible, it is just I ended up with someone like me, who is like me due a much different reason. While I love my wife, I wish I would've had a much more normal/average relationship life growing up. I know things would be different know, likely for the better. In the end, it is what it is.
13....cafeteria talk was interesting with this one. She had a bondage PC game in her room the first time I went in there. Didn't lose my virginity or anything, but definitely eye opening. Left me after about a month for a much older guy.
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