May 9, 2012 

I am a 26-year-old straight guy. My straightness and guyness are recent revelations, and it feels amazing to be able to confidently state this. Here is my trouble: I’ve had gender issues for the past five years. My now ex-girlfriend of three years said she couldn’t be with me anymore due to these issues. Our breakup was a result of my apathy in the bedroom, which was tied to my gender issues, and her fears of me transitioning into a woman. I can see now that my insecurities about myself caused me to be a selfish partner in many ways, but mainly in the bedroom. I now realize I was allowing my sexual kinks to get the best of me. I get very turned on by the idea of giving head to a guy, but in reality, it is not something that I enjoy. I also find lingerie to be very arousing. I allowed myself to focus so heavily on those aspects of my sexuality that I became insecure in my masculinity inside and outside of the bedroom. I also ended up ignoring the majority of my sexual desires as a result of my insecurity in my gender identity. I have now stopped repressing my lust toward women in general, something I had been doing that negatively affected my ex.

I am asking you, I suppose, for some advice. I am still in love with my ex. I am prepared now to be the boyfriend that she wanted me to be. But how do I prove to her that I am no longer the apathetic, distant, and repressed lover she was with for three years? I find myself overwhelmed with regret. She saw me as someone who couldn’t do the things she needed, when in reality I was just paralyzed by my insecurities.
Found Myself Lost

You’re not asking me for some advice, FML. What you’re doing is handing me a dog with a bloody, torn-up ass and saying, “Hey, Dan, I totally screwed the pooch. Unscrew it for me, wouldya?” Some days, half the mail is from remorseful pooch-screwers, and I do what I can to unscrew their pooches. That’s part of my job. But not every pooch can be unscrewed, FML, and your pooch looks eternally screwed to me.

It wasn’t your gender issues or kinks or anxieties that screwed that pooch. You don’t have to apologize for your gender issues. You were working through some serious shit. What you can be faulted for, FML, is your thoughtlessness, your inconsideration, and your neglect. You were so wrapped up in your own drama that you could barely perceive, to say nothing of meet, your girlfriend’s reasonable sexual and emotional needs.

We don’t have to be perfectly healthy or issue-free before entering into a relationship, of course. If that were the standard, no one would ever be in a relationship. However, we do have to be in relatively good working order, and you were not. Your girlfriend wasn’t looking for an issue-free guy; no such animal exists. But she wanted a guy who could have his issues and still make an effort to meet her needs. And your poor, neglected, taken-for-granted girlfriend stuck it out for three long years, hoping you might turn into that kind of guy-with-issues, before finally calling it quits.

And damn her timing, right? Because everything magically fell into place the moment she walked out.

So what can you do now? You can tell your ex that you’ve come to a couple of big realizations: You know yourself to be a straight man now, and you can see that you were a terrible boyfriend then. You were so wrapped up in your own anxieties and kinks and insecurities that you couldn’t meet her needs then, but you can now. The only way you prove this to her, of course, is if she takes you back. Considering the price she paid when you were struggling—inconsiderate, selfish, thoughtless, neglectful boyfriends are no fun, gender issues or no gender issues—she’s likely to pass. Because life is basically one big issue after another, and she may have concluded that you’re incapable of having an issue and being a decent boyfriend simultaneously.

If she doesn’t take you back—if that pooch can’t be unscrewed—resolve to learn from your mistakes, FML, and refrain from screwing the next pooch that comes your way.

Our next concern is who to invite into our bed. We would prefer it to be someone we wouldn’t have to see again, so friends are out. However, I am concerned about just finding a random person on CL or Adult Friend Finder, because being in a lesbian relationship, we definitely have run across men who think we “just need the right penis.” Basically, I want a man who I know is friendly with the queer community and will respect our relationship and our boundaries. Where do we look for this?
Another Bi Woman

Established couples that want safety, respect, and a measure of accountability from their very special guest sex stars, ABW, should look first to flirty friends and friendly exes. But you two, like so many threesome-seeking couples, want the perfect person to materialize immediately before sex and disappear immediately after. That means finding and vetting a stranger. And online personal ads are the best way to accomplish that. State in your profile that you’re looking for someone who 1) is queer-friendly, 2) respects your relationship, and 3) doesn’t think the “right” penis will turn you both straight.

Some guys will tell you whatever you want to hear, of course, which means you could wind up in bed with a man who doesn’t believe any of those things. But he’ll know to keep his mouth shut, ABW, and since you’re not going to see him ever again, does it really matter what he thinks?

As for your fear that your girlfriend won’t speak up in the moment: Address that with her, address it at length, and consider taking penis-in-either-of-your-vaginas sex off the menu for your first threesome.

I’m not one to toss that cruel “there’s someone out there for everyone” bullshit around. Fact is, some people do wind up alone. But kinks usually aren’t the reason. Whatever your kink might be, shy lil’ kinksters, there are kinksters out there who either share it or will spark to it.

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