What was your cringiest sexual experience?

I'm probably late to the party but it was my first time ever.

So I was dating this guy who was 20 for a while and being a horny teenage that I was, I suggested we take it a step further than just cuddles and makeout sessions, if he was okay with it. He said yes, but noted was a virgin, too, which honestly surprised me.

We gradually undressed while making ou and then we took off our underwear. Note that this was the first time I saw a penis, specially an erect one in real life, so when he displayed his way-under-average penis, I thought nothing of it, until he said: "Well, this is it", with the "this is my tiny schlong and it's all you're getting" tone in his voice. I found his lack of confidence and shame a bit weird and disheartening, but we put on protection and went ahead. He didn't even know how to put on a condom at first and ruined one while trying to put it on. When we finally geared up and got to business, it wasn't much for me, he was sweating profusely and well, it was my first, weird and uncomfortable time.

And then he was about to come. I've seen tons of porn by then and wouldn't have an issue with him cumming on me, as long as it wasn't in my eyes or hair. But no.

Even though he was wearing a condom, the guy got up, pulled out. Took off his condom.

Then ran across the room to his closet, opened it and came on the clean clothes neatly piled on the bottom shelf. He could have done it on the hardwood floor for easy clean up, but nah.

I figured he was just out of it the first time, but he continued to do it every time we had sex. I fled after a few times. It was just too weird.

/r/AskReddit Thread