440-pound virgin Gregg Casarona sent his girlfriend to the ER, because he sent her head straight through the basement’s sheet-rock wall during his first time.
Gregg and Jen had been dating for about one month, then they decided to eat the forbidden fruit. Sadly, the first time he has sex is awkward, the big inertia put 110-pound Jen’s head through the sheet-rock wall. Gregg’s first reaction was “OMG, I killed her, in my first time.” Fortunately, optimistic Jen pulled her head back from the wall and asked Gregg to continue. Gregg immediately sent her to the hospital and she was diagnosed with a concussion. That story happened around 8 years ago, now they have broken up but still are close friends and Gregg has successfully lost 220 pounds.
Does anyone has more memorable or more awkward first sex?