This is going to be a bit complicated, so I apologize in advance.

I am a queer, cis-gendered woman in my 20s who prefers male partners (sexually and romantically). For awhile now I’ve really enjoyed straight anal porn and fantasies, but have never felt comfortable with the idea of receiving anal or pegging. In my fantasies my perspective has always been that of the male and I’ve only recently realized that this is not because I want to get fucked in the ass or fuck a guy in the ass—it’s because I want to fuck another girl in the ass. As awesome as this revelation was, I have a few roadblocks to actually achieving this fantasy:

1. I have never had sex with a woman. The only thing I’ve ever done is make out with girls, but not even girls I’m attracted to.
2. I’ve never had anal sex in any form, though I’ve read a lot of how-tos and know the general theory behind how to make it good for both people, and I don’t really think anal’s something you just bust out with on the first fuck, especially if it’s the first time you’re having sex with a person of the gender you aren’t usually sexual with.
3. I’m in no way interested in having any form of a relationship with a woman, and I’m worried that without one I won’t find someone to help me fulfill this fantasy—partly because I am usually only attracted to women I feel an emotional bond with (as in, my friends).
4. I’m not out (well, I am to like 3 people), and I don’t ever intend on being fully out. Yes, I know this is partly due to internalized homophobia; yes, I know that’s massively fucked up (especially because I’ve been involved in several queer rights groups); yes, it’s also because I’m a bit of a coward and am afraid of the fallout with my family; and no, I still don’t ever want to come out completely. However, I feel like I would need to be out to pick up women in bars, etc.

I’m currently dating a guy who is everything I’ve ever wanted, but I’m not sure how he would feel about me sleeping with a woman without him, especially given the fact that I get emotionally attached easily to people I’ve been intimate with. I’d be interested in doing a group-type scenario, where I’m a temporary dom to a random sub girl in front of other people and he then doms me, but I’m strangely uninterested in threesomes.

I realize that my first step should be to find out how my guy feels about the whole thing and my second would be to decide whether he or my fantasy is more important if he’s not down, but the steps that come after it, like actually going and finding some hot femme sub to fuck, freak me the fuck out. A lot of it has to do with my previously mentioned internalized homophobia and my lack of desire to have anything more than casual sex with a woman, but I just feel so screwed up and jumbled in my head about this. I guess I don’t really have a specific question—just a desire for any advice you can give me at all.

Scared Wannabe Anal Pirate

My response after the jump...

Okay...

You're not sexually attracted to women you don't know—because you have to have some sort of a relationship with a women before you want to fuck her in the ass—but you don't wanna realize this assfucking fantasy with a woman you know because you tend to become attached to the people that you're intimate with and you don't want to be attached to the woman whose ass you fuck; you can't pick up strange women—women you wouldn't be attracted to anyway since you wouldn't have a relationship with them—because you're not out (and as much as I hate to be the bearer of bad news: very few of the out lesbian and bi women who congregate in dyke bars are dying to get fucked in their asses by "queer, cis-gendered" closet cases with zero interest in a relationship and boyfriends at home), and you're never coming out because you're a coward and you can't hit on your friends because then they would know you're not entirely straight—although I wouldn't describe you as anywhere near queer—and the news would quickly spread that you wanna fuck all your female friends in their asses and that could complicate your friendships and what if you family finds out and blah blah blah Eyes Wide Shut completely unrealistic dom/sub assfucking scenario... and scene.

Can't help you, SWAP.

I get lots of letters like yours: bisexual but not out, no intention of ever coming out, never had a relationship with a same-sex partner, never had sex with a same-sex partner, and an opposite-sex partner at home who doesn't know/wouldn't approve/wants to watch. So you're not alone. And, like so many of the closeted bisexuals who write me, you've got all the sex-radical/women's studies lingo down pat: you're cis-gendered (whatever to "cis"; here's hoping it winds up in the same landfill with "monosexual," and soon) and you're queer! Just not out! And never had a same-sex experience! But you're TOTALLY a member of my great, big, loving LGBTQITSLFABDB family. (That's lesbian, gay, bisexual, transgendered, queer, intersexed, two-spirted, leather/fetish, and allied, blah-de-blah).

You're not queer.

Now you don't need my permission to call yourself queer—very quietly, where no one can hear—and, hey, I knew I was gay when I was 14 and I wasn't out to anyone and being closeted didn't make me any less gay. So being a closeted bisexual doesn't make you any less bisexual. (But I was FOURTEEN FUCKING YEARS OLD when I was gay and closeted and still living at home with my Catholic parents—Catholic and religious parents—and I somehow managed to come out to my whole family by the time I was 18. Ova the fuck up, SWAP.) But "queer" to me has always implied a degree of bravery and bravado, a what-the-fuck attitude, and a life lived openly and honestly. If someone like you is queer, well, perhaps membership criteria are laxer than they should be.

Sigh.

Sorry to unload. It's just that questions like yours—and, truth be told, people like you—annoy me. Because everything you want you can have: there are kinky bi women out there who would be into the scenario you describe: you, your strap-on, your boyfriend. But those women are not going to kick down your closet door and beg you to fuck their asses. You'll have to go find one, SWAP, and finding one—or a series of them (fantasies rarely evaporate once they've been realized; if you like it, you'll want to do this again and again)—will require you to do what everyone else does when they're looking for a sex partner or a playmate: advertise, flirt, drink, flirt, hit on people, and, if nothing else works, rent. But you'll be outing yourself in the process, which you don't want to do/are too cowardly to do, which brings us back to...

I can't help you, SWAP—but you can help yourself.