Bottoms. Just how painful was penetration for you when you first first bottomed for a guy?

[BB4fking]

I remember the first guy I let try to fuck me. I had been to a ‘JO club’ I San Francisco which I seem to recall was supposed to be about jerking off. A guy drove me back to my hotel and came up to my room. I told him I’d not been fucked before but was willing to try. We persevered for some time but despite my willingness I couldn’t stop clenching my ass and he never fully penetrated. The guy  didn’t have the experience or patience to coax my hole open. My first fuck was months later and I can’t remember the details but I know it was with the guy who became my partner. He had a big thick cock but was gentle, skilled and patient so I’m confident it would have been a good experience.

[Teddybb]

Painfully forced but towards the end It was pleasurable pain. Then his brother fucked me with his brother's load as lube. 

[nwohionegbttm]

My first time I was 12 and raped by an older guy in an arcade restroom stall in South Carolina.  It very much hurt.  But for some reason that experience is what made me bisexual from a very young age.