When I was a freshman in college I went out with a girl who was in HS. She was a blonde cheerleader, etc. and I was basically her first everything beyond a kiss.
Needless to say she had a curfew of like 11:00 PM and I was a partyer so our "dates" usually consisted of the two of us meeting in a parking lot, going somewhere else, sexing in my car then maybe getting something to eat before I dropped her off.
I often would sex her, then leave and go drink/party later that night. I also cheated on her mercilessly.
Probably one of the lowest things I did was the night before New Year's some of her friends which was mix of HS and college kids my age had a party at a hotel. She couldn't go for some reason (her parents were really strict) and we got the hotel room.
I had a fake ID and got the booze. About halfway through the party, I start making out with one of her good friends. Later that night I had her topless and giving me head and was going to sex her but her other friends stopped it.
Yeah, I was kind of an ******* back in the day.