when i was getting my first blowjob, she bit my balls on accident and i was like yowzers!
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Her teeth hit my penis, but I still had to smile and comfort her. 
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Having our favorite toy die right before finish
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I took a 9in penis fully up my butt in one thrust. I withered in pain for a solid 3 mins. One should ALWAYS prep and stretch and use lube when practicing anal. Definitely learned that one the hard way.
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I was a s&+ worker for 3 years and I had several guys hump the inside of my thighs thinking they were hitting it and I’ve had one guy hump my bellybutton raw, but worst experience has to be the one time I tried to take a 9+ inch penis and I cried half way through it hurt so bad felt really bad for the guy so I ended up giving him a BJ to finish him off.
I feel you on those 9in penises. I think my worst experience is the time I got ripped or the time I took that 9in penis up the butt without prep.