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Where can a straight guy find a transsexual woman who is NOT a hooker and just wants to be friends (with benefits)? I know of one club where they hang, but they are mostly hookers there. I would like to go someplace where I could meet one and see if we could hit it off and go from there. I know they are out there, but I just can’t find them! Help a brother out! PLEASE! PLEASE! PLEASE!
—Lonely Tranny Lover
If what you’re looking for is a transsexual who’ll allow you to fuck her—or who’ll fuck you—but who won’t require you to have an actual relationship with her, LTL, then you’ll have to pay some nice woman for her time and her emotional distress, like all the other straight guys out there into MTFs. Why do they have to pay? Because, LTL, it’s kinda shredding to sexually service someone who’s embarrassed to be seen in public with you. Just ask any openly gay man dating a closet case and/or a Catholic priest, or any BBW sleeping with a man who’s married to a rail-thin trophy wife he isn’t physically attracted to. Someone who puts up with that kind of bullshit—“You blow me, I blow you off”—should be compensated for her time, pain and suffering.
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 non-trans women want. Be open to an actual relationship, LTL, and you’ll have an easier time finding a non-pro who’s open to you. —Dan
I’m a 24-year-old straight female in a relationship. The sex is great, except for one thing: My boyfriend is so fucking quiet while we are having sex. No words, no moans, a stone-cold facial expression. I know he is enjoying himself because he always comes and he initiates sex as often as I do. However, his stoic demeanor makes it hard for me to really get into stuff that isn’t directly pleasurable for me. It’s hard to be motivated to choke on someone’s cock when they look and act like they can’t even feel anything.
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.
Why is he so quiet? What can I do?
—We’re Not In The Library
Stop treating this like it’s a problem, WNITL, even if you experience it that way, and start treating it like a challenge and a game.
Give him a blowjob, choke on that cock, bring him right to the edge, then pull his cock out of your mouth and say, “Do you like that? Are you close? You want me to keep going?” Then look up at him and slowly stroke his cock—not fast enough to get him off, but not so slowly that you’ll have to start that blowjob all over again—and wait for his response. When he says something, his dick goes back in your mouth. When he stops talking, his dick comes back out. Or if he’s fucking you and he’s getting close, wrap your legs around his ass and pull him in and hold him there so he can’t thrust. Then say, “Feel good? Getting close? Wanna finish?” Don’t let him budge until he talks; don’t let him continue if he stops talking.
Be playfully, sexily confrontational, WNITL, and you’ll be able to extract the feedback you want during sex while helping him get over his insecurities about how men are supposed to act during sex. —Dan
My boyfriend/fiancé likes to be put in a cage, and we have a very scary-looking cage 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 for me to 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.)
I’ve been reading your column since I was 19 (I’m 27 now), I’m GGG, and I’m happy to do this for my boyfriend. And knowing he’s in there waiting for me—and doing crunches to pass the time (you should see his abs!)—does make me horny, too. The issue: I won’t leave our apartment when he’s locked up. What if there’s a fire? Or we get burgled? Or if there’s a meteor strike? Or a terrorist attack? He says I’m being paranoid and that it really turns him on to know that I’m out with my girlfriends, having drinks or whatever, while he’s locked up in my closet “with the rest of my things.” Who’s in the right here?
—My Boyfriend Is My Prisoner
P.S. Our only other conflict: He insisted we find a place with two closets, one of them walk-in, because he wants to be stored in my closet, not a shared closet, “with the rest of my things.” (That phrase really turns him on—he’s one of my things!) We passed on some beautiful apartments because the closets weren’t perfect, and my mom—who helped with the down payment and apartment-shopped with us—thought we were crazy. If only she knew!
You’re in the right, MBIMP. If there’s a fire or a robbery or meteor strike—or if you get hit by a car and wind up in a coma for three months and he slowly starves to death in your apartment—then you could go to jail for manslaughter and/or negligent homicide. So that fiancé thing of yours shouldn’t be left alone when he’s in his cage; no one should ever be left alone tied-up and/or imprisoned. If he insists on you going out on a cage weekend, MBIMP, then you’ll have to hire a sitter—bondage, not baby. Take out a personal ad, lay out what you need (someone to be there, in case something happens, but that’s all), and very, very carefully interview applicants. Better yet, get involved with your local BDSM group, make some kinky friends, and see if anyone is up for a little bondagesitting.
Or, hey, you can live a little dangerously: Give your boyfriend a cell phone, don’t go far, and instruct your prisoner to call if he smells smoke while he’s doing his crunches.
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