I had a similar occurrence when I lost my virginity. Roommate was out of town so the date consisted of a "Netflix and chill" scenario - watching some DVDs, and having a few screwdrivers (thanks to roommates ability to purchase alcohol). Cuddling on the couch escalated past the making out to "Let's take this to the bedroom".

During the fun stuff she suggested taking off the condom. This already felt amazing, why should I settle for good sex when I can have great sex? I have enough self control to pull out. Off came the condom and noticing how much pre cum there was I ran to the bathroom and washed off, gotta be safe about this. (Yes, modern me is perfectly aware of the flaws in the horny logic).

Round 2 experienced catastrophic failure almost immediately. Switching positions to doggy style, freshly cleaned and dried penis, it was an amazing few seconds before I felt a "pinch", then pain. Panic made things after this point a little hazy. She was scared she had done something wrong, I was scared I had broken my dick. So much blood.

After a long night spent in the bathroom trying to stop the bleeding enough to see what was actually wrong (and cursing an erection that didn't care what I wanted) we were able to see the torn tissue. Many dick pics from "uncle google" later, I was able to stop the bleeding and we were able to relax. The aftermath wasn't a lot of fun, but not really unexpected. Painful peeing, painful boners, painful showers, blood here and there...

TLDR - Tried to have dry sex with girlfriend. Annihilated frenulum. Pain, blood, blood. Get to joke with wife that she broke my hymen.