It was one of the most pathetic experiences of my life. So pathetic that I will only reveal it on an anonymous porn board.
I was a junior in HS. He was too. In the beginning, we were just pals. Then it turned emotional. For me, anyway. I let him squeeze my tits. And He let me stroke his dick. We kissed & flirted all the time. Whoop-dee-doo.
So one day we ended up at his house. He told me to come with him down to the (unfinished) basement. (imagine a cold, dark, cement room that smelled like mildew.

) My dumb, vulnerable, silly ass did. He threw his tongue down my throat. He then told me to lay on a pile of (dirty) laundry on the floor.

And just like a young girl crying out for negative attention, acceptance and approval, I did.
He removed my panties, fingered me for 10 seconds and then penetrated, unprotected. It hurt, but apparently not enough for me to tell him to stop.

About 1 minute later, he pulled out and squirted what seemed like a gallon of cum on my stomach.

He so elegantly wiped me off with a towel from the pile of laundry.

Bastard. Then I went to the bathroom and saw why they called it "Busting the cherry". Total time elasped: 4 minutes.
He was young and dumb and so was I. Therefore, I have no regrets. It was the 1st of many important, powerful life lessons about men, relationships & self-worth: If you allow a ninja to treat you like dog-shit....he will. Period.
Today, we no longer talk, but we have mutual friends. He is married to a celebrity wife. I see him on TV from time to time. From what I understand, he regularly has affairs and has several children by other women. Oh-fucking-well.