Most painful? Let’s see, me and a special lady were having a bit of adult fun. I was feeling extra good this day so I was really giving it to her. She remained quite wet, so there was no need to add lube or get her any more ready than she already was. About 10-minutes into it, we began changing positions. She laying on her back on the edge of the bed, legs reaching behind my head as I stood on the floor next to the bed. I started stroking and got a little too into it and slipped out. Not wanting it to happen again, I reached forward to pick her up and hold her in my arms. The only problem she thought I was leaning forward for a kiss. My forehead found her nose and she shrieked in pain. She threw herself down on the bed, finding her laptop with the back of her head. She then sprung up, this time her forehead finding my nose. Before I knew it I’d lost control and began to climax as blood poured from my nose. As I struggled to hold my composure, my legs gave out and I somehow fell in such a way to fracture my toe.

So there we were, walking into the hospital - well she was walking, I was limping. She had a shiny red nose and a purple forehead, I had a bloody shirt and a slightly red forehead. Upon first seeing the doctor, he thought it was a domestic dispute, but after awkwardly explaining it was a sexual accident, the three of us laughed and as we left he told us “leave the trapeze acrobatics to the clowns”

Yep, not my best moment, but we still laugh about it to this day.
A week later I had to see the same doctor for cracked ribs - not sex related though.

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