What was the most painful experience you had during sex or masturbating?

[josephinelcajon]

LOL I was like 10 stuck my dick in a vase to masturbate and got stuck! Mom and I tried lube that just felt good making me even harder. so then we tried masturbating me in hopes the orgasm would soften it. I did orgasm but no luck getting it out. We finally tried ice to shrink it which took a long time but finally got it to slip out. It was so painful! We harmed me up with a hot washcloth and lotion that made me hard again and painful. We LOL about that for years!

[shinnaeun]

My ex every time we slept together. He basically would go so hard and not take his time or anything, it was bad, especially cause he was pretty big and I’m too tight so it would always hurt.

[MayBrayNaughty]

Being interupted at the crucial moment and not being able to climax when I was sooooooooooo close 😬

[BlondeGoneWild]

Having my nipple tazed

[Anonymous]

Never had a painful experience