Bottoming, crossdressing and bisexuality have got me hella confused.
Heather Corinna replies:
I'm very confused with my sexuality; I'm a 17-year-old Austrailian male who is definitely attracted to women, but at the same time have an attraction to men that mostly involves fantasies where I play the receptive "bottom" role. I have acted upon these fantasies and sought out sex with other men, however every time it comes to engaging in oral or anal sex I enjoy it far less than I thought I would, even to the point of being bored! Every time I swear it will be my last because I didn't enjoy it, but lo and behold I get aroused again and seek out sex with men, and leave again disappointed. I'm also not attracted to the actual man; more the penis. I don't know what this means; it's worth noting that I have engaged in sexual activity with women, in everything other than actual intercourse and enjoyed it greatly. Add to the confusion the fact that I have a longing to crossdress, especially in women's lingerie, and I'm about as confused as it's possible to be. Please help shed some light on the situation!
There's nothing like starting to put together all of the myriad complexities, preferences and desires of our sexuality to point out how silly it really is to suggest that human sexuality, sexual orientation or gender can be easily divided into such tiny boxes, is there?
The short of it is that I think all of this will become a lot less confusing if you can let go of whatever ideas you might have about sex and orientation being any one group of very simplistic things. I've said it before and I'll say it again and again: what's "normal" when it comes to human sexuality is a great diversity. Too, what our desires and sexuality are is often fluid, from decade to decade, year to year, day to day and situation to situation.
Here comes the long of it.
Given all of what you've posted, I think it might also be helpful for you to unpack some of your ideas or thoughts about gender roles.
For instance, while it could be that your feelings about genital sex with men are influenced by internalized homophobia (and we all have some of it, no matter how queer -- or not -- we are, believe me), on the other hand, you report having enjoyable genital sex with women without those feelings. So, you might want to consider that it might be role-play -- or simply some new, more flexible ideas about roles -- that could be the happy medium for you here. In other words, you could just as easily bottom with women and have them butch up their gender roles during that sex with you: if it's penises you're very drawn to, women do also have the capability of using strap-ons. If what you're drawn to in the sex with men isn't the men themselves at all, but the fact that you can have the role play you want with them: just know that's also an option with women, too.
Another option would be to engage in bottoming play with other men that doesn't go to genital sex at all, or have you always being a receptive partner, since it certainly doesn't have to.
One other possibility may just be that the types of genital sex you've been having with men just aren't doing it for you: again, what you do is up to you. If you want to have sex with men, that doesn't have to involve receptive anal and/or oral sex if that is boring or unfulfilling for you.
There's also no need to be confused or distressed about a desire to crossdress: it's not that uncommon, especially among heterosexual men -- but some bisexual and homosexual men have that desire, too -- and that may also be related to your desire to bottom, to boot, if you see the "feminine" role as one of a bottom (something I'd perhaps obviously ask you to examine if that's the case overall, since it's not so balanced to think of any one sex, race or orientation as somehow naturally being on the bottom, but that doesn't mean that it's problematic for you to role play with that in your own bedroom, either).
It can be a bit tough when you're young and you have desires like yours -- both in terms of bottoming and cross-dressing, as well as pretty clearly being bisexual -- which a lot of peer groups might view as abnormal. But they're really not. Certainly, a couple of these things are far less common, but they're all still desires which many people have. Sometimes, we're just precocious in our desires, realizing stuff we have outside the norm a bit earlier than our peers: but again, that doesn't mean you need to feel confused -- if you do -- about these things just because they may not resemble other teen sexuality you see. Like I've said, we're all very different, and we all also have unique timetables when it comes to our sexual development.
That given, with some of the alternatives I've suggested, it's sensible to be realistic and make clear that it may not be so easy for you to find partners that are a good match for you: certainly not as easy as it usually is for more heteronormative folks. Who knows: that may be part of why you keep returning to sex with men (or it may just be because you want sex with men, even if what's happened to date hasn't been all that satisfying -- lord knows lots of heterosexual girls your age are in that spot with the sex they're having, too), because it's at least one way you feel more able to address some of these desires. But over time, so long as we branch out past whatever our small peer circle is, more of those partners will likely show up, especially as you discover more channels to seek them out, and people's ideas about sexuality evolve and widen over time. Those partners may be male or may be female for you, and I'd say it's also worth considering that you may have met more female partners to date that are a better fit for you than the male ones you have had. Without sounding like some girl's pushy granny, you simply may not have met the right men yet for you, or may just need to pipe up about other things you need, like more verbal interaction, more play with the roles, etc. If it takes a few more years for you to find partners interested in and willing to explore some of this further with you, that's okay: none of us is harmed by not being able to fulfill every single kind of sexual desire we have at a given time -- just liek none of us is done harm by not being able to eat exactly all of the sorts of foods we might crave -- and all of us will have times in our lives when we don't have the opportunity to do so.
In case you needed to hear it: you're okay, and the desires that you have are okay, even the ones that are a bit more unusual. Plenty of people have unusual desires, or things that fall outside the norm in terms of their sexuality, especially considering how narrow the "norm" often is!
Our sexuality also doesn't have to "mean" something, nor does any one facet of it. Most sexologists agree that a lot of our desires not only are formed when we're very young, but are a pretty complex cocktail of a whole lot of things: life experiences, fantasies, personal identity, how we relate to others, biology and physiology...you name it, it's likely part of your sexuality. While it's often helpful and enlightening to analyze this stuff now and then, often enough, we'll have a desire or set of desires that we can't find any source of or particular meaning in. That doesn't mean something is wrong with us: it doesn't have to mean something. Rather, it just should ideally feel emotionally and physically good for both us and our partners, be an enriching part of our life, and be completely okay with, and safe for, everyone directly involved. In terms of evaluating your sexual orienation, everyone often has different levels and spheres of attraction: it's normal for bisexual people to have stronger physical or emotional attraction to one given sex or the other, for instance.
This may not be necessary, but as a sexual health educator, I also want to make sure that with all of this, you've got safer sex down, especially when you're having multiple partners or a lot of very casual partners. With male and female partners alike, it's critical that you're using condoms for oral and anal sex (you say you aren't having vaginal intercourse, but if you were, with that as well), and that you're being sure to get a full STI screening at least twice each year, okay? Multiple partners of multiple genders up your infection risks and those of your partners, and anal sex is particularly risky unprotected: be sure that while you're exploring your sexuality, you're also taking good, preventative care of yourself.