BayAreaBtm
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Guess I'm one of the lucky ones: First time I tried taking a cock in my ass was as a teenager—and there was no real pain or discomfort, I just wanted MORE cock and cum . . .
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A few years ago I had a hookup (with a guy I've since lost touch with, but he was fun AF for reasons below among others . . .), where I met him at his place, and started off things there. We then upped the ante by walking to a park down the street from his apartment, and just off the path running through the middle behind some trees and bushes, we kept up the fucking for awhile before moving indoors again. Fairly standard outdoor exhibitionist stuff, even at night (which it was) . . . aside from the fact that about 50 feet or fewer away was a sidewalk where I could see people walking to and fro on the park's edge . . . . . . that, and the police station on the OTHER side of the park's boundary. We obviously didn't get caught by civvies or cops, but still added a fun element to things 😉