Ok so I've been dating this guy for a couple of months and the other night I decided I was ready to have sex with him. I am a virgin and he is not, however, we never talked about it directly. I was obviously a little nervous, but ready. So things start escalating, he puts the condom on, and we are ready.

But there's an issue- he's not the smallest and I'm a virgin, so I'm pretty tight

In fact, I'm so tight that he can't even "enter"

It's not just the fact that I'm tight that affects it

His condom didn't have any lube, he didn't really do much foreplay, etc.

We tried TWICE that night and it just didn't happen.

Fast forward to the next day, he messages my BEST FRIEND asking if I'm a virgin. He told her that he asked me if I was and I said no.

EXCEPT HE NEVER ASKED ME AND IF HE DID I WOULDN'T LIE.

Has this happened to anyone else? Or something similar? Or is there something wrong with me?

Also, just thought I'd throw in that he also told her that if I am a virgin he "wouldn't wanna because he's not like that" and I haven't heard from him since the night we tried having sex. And I'm a little heartbroken. Please let me know what I should do

This is the conversation when he messaged my best friend (blurred out names for privacy purposes)