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".
(n) A person who you may tell to their face they are your friend or a person who you don't actually like/trust for whatever character flaw. They may be in your friend circle but on a one-on-one basis they are not a friend to you. However you keep them around because for whatever reason it may be, they help you in some way.
Jim: Why do you chill with Eric? I hear he snitched on Kenny. Plus he's kind of a dick to your sister.
Greg: Because he can get me alcohol. He's pretty stupid so he doesn't know I hang with him just to get me drinks. He's just a bootleg friend.