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.