Q Where can a straight guy find a transsexual woman who isn’t a hooker and just wants to be friends with benefits? I know of one club where they hang, but they’re mostly hookers there. I’d like to go someplace where I could meet one and see if we hit it off and go from there. I know they’re out there, but I just can’t find them! Help a brother out! PLEASE! PLEASE! PLEASE! —Lonely Tranny Lover
Best of Chicago voting is live now. Vote for your favorites »
It’s nice that you’re willing to be friends with the transsexual you’re fucking, LTL—that puts you above most straight-identified men who are into trans women. But most trans women, hookers or not, want more than that. They want love, companionship, intimacy, and a commitment—you know, all that shit nontrans women want. Be open to an actual relationship, LTL, and you’ll have an easier time finding a nonpro who’s open to you.
I’ve mentioned this to him several times after sex, and he just laughs it off and then says something like, “Do you expect me to scream like a girl?” I’ve told him that that’s not at all what I expect. I just want some sign of life! One time, I purposely remained completely silent during an orgasm, like he does, and he became very self-conscious. He didn’t believe me when I told him I came, and I asked him how he likes it when I’m quiet. He thought this was funny, and then things went back to normal.
Q My boyfriend/fiance likes to be put in a cage, and we have a very scary-looking one in my closet. (God help me if my mother ever finds it—I’ll be in more trouble than that guy whose mother found his life-size sex doll!) His biggest turn-on is to come home on Friday night, go right into his cage, and have me keep him there until Sunday morning. I only let him out if he needs to have a bowel movement or if I want to screw. (There’s a bottle of water in his cage if he gets thirsty and an empty bottle if he needs to pee, and he doesn’t get fed much because he’s not exactly burning calories in there.)
A programming note: Lots of folks have asked me where my iPhone app is. Well, I didn’t have one—until now. The Savage Love iPhone app has been submitted to Apple. Will they accept it? Or will it be too porny for Steve Jobs? Stay tuned.