Dear Erin, So here's the deal. I'm 34 years old, and I'm at sea about my gender identity and sexual orientation. I was born and raised male, and it didn't work out very well for anyone, so I started living as me, which is Gail. Here is where it gets tricky.
Four year olds run around saying "Boys have a penis. Girls have a vagina." Wouldn't it be great if it were that simple? Some of us just don't have it that easy. My name's Gail. I look like my name might be Gail, or maybe Alison..but it's Gail. But I have my original equipment "down there". If I had surgery to make myself look more like a typical "Gail" down there, well, I could get naked in a locker room without scaring anybody, and maybe attract a wider variety of prospective partners. Other than that, I ain't feelin' the need to go "under the knife".
I feel like being in this in-between state will scare a lot of people off, and make me more socially awkward than I am with my clothes on. I am 100000% bisexual, but lesbians and bisexual women who are attracted to me initially, because they see Gail on the outside, tend to cool off when I tell them what they might see if we ever got beyond flirting.
Guys are WAY worse. They're SO insecure, except for the fetishists. There are guys who say "I watch so much shemale porn, that you're my fantasy come true."...These guys are usually the shittiest, most sexist bastards who wish they could have a 1950s housewife who looks hot, is submissive, can intuitively could give great blowjobs, and who can "think like a guy" about how a man wants to be pleased. (Some of them play this little game called "I won't say you're a guy, if you don't call me gay for thinking you're hot." Pretty gross, ay?). I know that there are a FEW guys who, if they saw the "right stuff" when I was naked, would be able to deal with my past. THOSE are some real men.
It seems like I can't be a lesbian, I can't be with bisexual women, and I'm not sure if changing my body is going to change all that. I'm seeing a shrink, and my shrink sees others like me. (Can you believe there are like tens of thousands like me???). My shrink says that if I don't feel the need to have surgery, doing it to get laid is a bad idea. That sounds right. But today there are all these LABELS! Everybody puts a NAME on everything. So...what am I supposed to be if I'm in between? "Transgender"? "Shemale"? Who's gonna fuck me? If I were ten years younger, I could be a hooker, but I don't want to do that.
What do you suggest?
Gail, I like to see myself as a free-wheeling, iconoclastic brand of advice columnist. I dance to the beat of my own advice drummer. My ideas might be unconventional - even controversial - but I'm committed to putting it out there and saying what's in my heart. So here goes:
Do not have elective surgery to remove your penis unless you are absolutely certain.
Call me crazy, but it seems like the kind of thing one shouldn't sort of guess they might kind of want to maybe do. In my humble opinion, a baseline requirement for medically altering one's junk is being at least as sure as you need to be before, say, getting a tattoo. And you don't seem even remotely tattoo-sure here. So I'm with your shrink on this one: let's keep the status quo below the belt.
That leaves us with the rest of your question. You've clearly had a variety of disappointing and confusing experiences with men, and a number of non-starters with women. And it seems like you're struggling with how to, for lack of a better word, market yourself for dating and relationship purposes. The phenomenon of the online dating profile inevitably leads all of us to hysteria-inducing confusion over what labels to choose. ("What's my body type? Curvy? A little extra? What does that even mean?") It's a universal conundrum that's brought to an existential scale for you (and, indeed, the many thousands of wonderful folks out there like you).
But it's a mistake to focus too much on self-presentation when dating. Lots of people of every gender and sexual orientation fixate on themselves and what may or may not be wrong or right with them, so much so that they never manage to progress into the other-focused mode one needs to be in to actually find love or even just a fun hook-up. In sex and dating, it helps to have faith in yourself as you are and focus instead on what you want, on what you're looking for.
The crazy thing about that, of course, is that we generally cannot accurately identify what we really want. People fill out dating service forms demanding minimum IQs and baseline heights and ideal body sizes for potential mates, but, when push comes to shove, they end up selecting romantic partners on completely different criteria. In the end, none of us finds love by advertising our labeled selves on a billboard or posting a detailed want ad. We find it by interacting with other human beings. Even people who connect online generally exchange emails or meet for coffee to see if they get along, and those conversations are not typically about sex organs, bank statements, or professional resumes. They're just simple, friendly human interactions.
So, my advice is to be Gail out there in the world. Join up with others who share your interests. You could go the route of, say, political groups that promote the rights of LGBT people and sexual minorities, but I encourage you to look beyond those groups as well. For the sake of your safety and sanity, you probably want to focus on communities, interests and activities that are generally accepting of queer people. I would advise against NRA ski trips or GOP fundraisers.
But there are tons of great options out there. Kickball and ultimate frisbee are just two of the many sports that feature co-ed adult leagues, and there are running clubs and yoga studios and hiking groups and lots of other places to enjoy solo sports with a group. There are queer book clubs and sci-fi book clubs, there are live events for people who enjoy the same online phenomena (xkcd has had some awesome meet-ups in the past), there are writing workshops and fermentation clubs and lots of opportunities to meet people you might not otherwise get to interact with.
Even if you don't meet a special somebody, I suspect that making new friends and just being your regular ol' human self in a group setting will give you the confidence to proceed into the more overt dating worlds of bars and websites with a greater sense of confidence and less confusion over how to label yourself. And always keep in mind that others are capable of expanding and transforming their own identities based on who they come to love. I know gay men who date trans men. I know lesbians who started to identify as bi when their girlfriends decided to transition. I know several trans women who are married to cis women and have wonderfully supportive partnerships.
Alas, it will be probably always be tough to figure out when to tell potentials about your anatomy... Based on your experiences, it seems like avoiding homophobic straight-identified men might be a good thing to try for a while. I'm not quite sure why you rule out lesbians and bisexual women so utterly. And what about other trans people? It seems to me that other out queer individuals, especially the more open-minded and curious among them, would make excellent potential dates for an awesome person like you. And no money needs to change hands!
What's clear to me, Gail, is that you're smart, you're interesting, and you approach others with an open mind and an open heart. I'm confident that you will find more and more people who share your awesome attributes and reciprocate your openness.
And you just have to be Gail.
Hey, you! Want some sex and relationship advice? Of course you do. Contact Erin here.