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My boyfriend let me experiment on him with a strap-on. At first he didn't like it, but now he loves it. Now I want to have sex with another guy and watch him suck a real cock. How can I get him to try this?

Pretty Eager Gal

Jesus Christ, PEG! I have plowed years—years!—and thousands of words—thousands!—into convincing straight boys that there's nothing gay—nothing!—about a woman fucking a man with a strap-on. Whether he's penetrating her or she's penetrating him, I told 'em, it's still straight sex. And people were buying it! (Well, not the editors of Vice Magazine, but they're not human.) And then you come along, PEG, and undo all my good work in less than 50 fucking words! Now every guy whose girlfriend wants to peg his ass is gonna think it's some vast conspiracy to turn him into a dick-lickin' bitch!

I can't bring myself to answer any more letters this week. I mean, why bother when all my hard work can be undone in an instant by a thoughtless person who can only think about what she wants? So I'm turning this week's column over to a pack of female-to-male transsexuals. They've got some good advice for The Impossible Fantasy, the gay man who's attracted to "guys with pies," or hypermasculine FTMs, but wasn't having any luck finding an FTMGWP willing to sleep with him. Take it away, gentlemen.

As a gay-identified FTM, my first reaction to TIF's letter was, "Wow, too bad that guy comes across like such a creep." Given that reaction, I'm not terribly surprised he's having trouble fulfilling his fantasy. As a public service, I'll try to unpack (ahem) why that was my reaction.

1. Most transfags are not and do not consider themselves hypermasculine, so that could be part of the problem right there.

2. Even if he isn't too particular about that aspect, many transfags are, strangely enough, not all that into traditional gender roles, so the hypermasculine requirement is probably off-putting to more people than just me.

3. There are definitely transfags into having sex "up front," as they say, but it's not something people like to advertise. So initiating contact by saying "I want to fuck your pussy" may be off-putting.

4. A lot of transfags—not all, but a lot—are into the leather/S&M/other-weird-stuff scene, so if he's not looking there, that may be another reason he's not finding many.

5. Like you mentioned, Dan, a lot of transfags feel that finding a gay-identified man who will accept their genital arrangement is a lost cause and aren't looking all that hard. If TIF is looking mostly in places—web or real life—that are geared toward sex and dating, he's probably not going to run into many transfags. He might have more success making contact through groups with political aims or through support groups.

Alex

I'm a gay bio-male with a comment for the gay man interested in "guys with pies." Based on what I know of my FTM friends, here's a suggestion: When you meet a gay/bi FTM, don't call his genitals by female names. Call it his cock. Treat it like a nice, hot cock. By accepting his body for what he might prefer it to be, you have a better chance at making him want to be with you.

Charles

I'm a transman—queer identified, post-op (chest only)—who might have a few insights for TIF. An obvious one is that transguys often have resentment toward their pussies. They identify as purely male even though technological restraints in the medical field aren't able to offer them anything more than a lifeless flap of skin taken from their own forearm.

A lot of transguys (including myself) began their transition by first identifying as a butch lesbian. Being in the lesbian community during a time when you're forming your identity can bring you into contact with the notion that penises are oppressive and gross and a symbol of the patriarchy. For transguys who followed this path, those ideas might be a little hard to shake.

On to the Stone Butch phenomenon: Many butch lesbians don't like to be penetrated because they feel disempowered or feminized when they're being fucked. Some transguys definitely continue to uphold a very strict no-penetration policy—some even have no-touch policies.

TIF mentioned that most of the FTMs he's met have been straight identified. For many FTMs, especially recently transitioned ones, there is often an obsession with "passing" in society as male. A lot of FTMs wear very stereotypical male clothing and act in very stereotypically male ways in order to pass. And what does a stereotypical male find attractive? Women. Tits and ass.

Personally, I'm not strictly gay identified because I love fucking women, but I also enjoy getting slammed by a hard cock every once in a while by a guy with a tight chest and stubble on his chin. As an FTM who sought for so long to acquire a male body, how can I deny the beauty of the male form? I have no doubt TIF will eventually find an FTM who is willing to "bottom out" for him. We're definitely out there.

One of Many Guys with Pies

A thought from an FTM for TIF: I transitioned six years ago and this is the first time I have encountered the phrase "guys with pies." I Googled it and only got porn sites (and people upset about Ann Coulter getting a pie in the face). He might want to rethink his language. Calling a cunt a "pie" just sounds childish. That said, some FTMs appear to find the term "mangina" seriously erotic, so maybe I'm just straight-laced.

And while I'm here, Dan: When you periodically respond to those pre-op FTMs moaning that they can't get a date, your answer annoys me a bit. You state that most gay guys don't want anything to do with trannies, end of story. My experience has been that a lot of gay guys will give it a whirl if they've never been with a tranny before. Relationships are tricky, absolutely, but a reasonable amount of confidence and getting laid isn't.

Paris

If that chap TIF isn't aware of the porn performer Buck Angel, he should be. He's exactly what TIF is looking for.

Keefer Reefer

Holeeeee shiiiiiiiiiiit.

I Googled "Buck Angel," checked out his website, and then had to spend the rest of the day in a dark room with a cold compress over my eyes. Like, wow. If ever there was proof that there's someone out there for everyone, hypermasculine FTM porn star Buck Angel is it. (Check Buck out at www.buckangel.com.) He's just the thing TIF has been looking for—just the thingless thing, I should say. Enjoy, TIF.

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