Bootleg Anal is when a woman cant adequetely take/recieve more than the tip of a mans penis in her anal cavity. It counts as anal sex, but much pleasure isnt derived from the act.
"Did you go home with Stacey last nite"?
"Yeah...we hooked up. she was on her period, so I got some bootleg anal. she was pretty drunk but it was still difficult".
the act of only rolling a condom past the tip/head of your penis, to avoid the boring feeling of sex inside of a piece of rubber. Made famous by Porn legend Ron Jeremy
"I didnt want to wear a condom, but since I had to, I just did the Ron-Jeremy-Roll and got it poppin".
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