I am a gay man who got a crush on another gay man, a super-cute boy who just blew me away. In addition to being one of the most handsome men I've ever met, he's also funny, smart, and goes to my church. So he's a very kind and honest person. But. (Why is there always a but?) Come to find out, he is an FTM. I have a million questions whirling through my head. Let me try to ask you some of the most important ones because I think it would be really rude to ask him. I've tried to locate some information for guys in my situation, but there doesn't seem to be anything in print. Okay. First of all, what does this mean about me? He is pre-operative, I think, because he told me he had chest surgery but didn't mention anything else. So I'm falling in love with, if not a woman, at least a person with a vagina. Does this make me bisexual? I have never had sex with a female. I love gay sex because I just automatically seem to know what to do with a body that is like my own. I don't know if I can go through with having sex with him. I want to, but I feel uncertain about my ability to perform, if you know what I mean, and I don't want to hurt his feelings if my dick won't behave.
If we did get past the first date and have a relationship, what will I tell my friends? What will they think? How will I deal with it if they are snide and mean about him? I don't think I could stand it if anybody made fun of him. He has so much dignity and courage. I'm very tired of being single, and I think he really might be the one, but fuck, I'm confused and scared. Should I just tell myself it's too complicated and try to move on? Or is there some way to make this work?
You are a guy who got crushed-out on another person who looks and smells like a guy. So I would say that makes you G-A-Y, gay, honey. So calm down with the uproar about your own identity. You don't need to put yourself through that.
However. (Why is there always a however?) This doesn't mean that you and this particular transgendered man will be a good fit sexually. I understand your anxiety about his body. Even if he identifies as male, he still has some body parts that began life as female anatomy. So what does a Kinsey 6 man do with a guy who has a vagina?
The answer may be: nothing. You may decide that your performance anxiety is just too great to risk a sexual encounter. Or you may try sex once and then decide that it isn't for you, or that you wish it was for you but, as you put it, your dick won't behave.
But some of your anxiety may be reduced to a manageable level if you and your lust-object can have some calm conversations about what each of you want and what each of you feels he can do. If there is enough overlap, well, you certainly have at least as much of a chance of a fun evening as you would have if you picked somebody to go home with just as the bar closed. Also be aware that you don't have to move immediately into the realm of let's-take-our-clothes-off-and-fuck. Couples lose a lot of time to build intimacy and trust when they immediately forego all the preliminary stages of love notes and making out.
FTMs differ a lot in self-definition, body types, and sexual preferences. Some of us feel we are just male, some of us call ourselves transmen, some of us don't like the restriction to a male or female category. We can be gay, straight, bisexual, or asexual. Some of us have chest surgery (which leaves scars behind and often some areas of numbness on the skin or nipples), some of us don't, and there are many different opinions about what kind of genital surgery to get (if any). I doubt that your new friend is going to mind a whole lot of if you ask him politely, in a private place, if he can tell you more about what his body will look like when he strips. Share your own good and bad points. Hearing about your own physical insecurities will help him feel less singled out.
Then get down to it in terms of what has he done with other guys, what does he fantasize about, what does he know he likes or doesn't like, etc. And again, share your own history here. How do you both feel about oral sex, condoms, anal sex, lube, handjobs, massages, fantasies, verbal trips, jerking off, underwear, muscles, porn, rimming, fisting, kinky sex, and whatever else gets you hot. You may have met a guy who doesn't want any reciprocal sex. He may only be comfortable paying attention to your body. He may or may not want to jack off as part of sex. Maybe he is a top who wants to penetrate you. Although he will probably need to use a sex toy to do that, don't knock it until you have tried it. Some FTMs like anal penetration, and others do like vaginal penetration, but not all of us can deal with this.
Tell him about your insecurities. Let him know that you want him a lot, but you just aren't sure how your involuntary reflexes are going to react. Ask him if you can take this one step at a time, and learn together. He may have very little experience with a genetic guy's body, so you may have to teach him how to suck your dick, so it's not like you are the one who is going to have to do all of the learning. That's okay. Let's not let either one of you get boxed into the mindset that everything has to be perfect right away, or the whole relationship is hopeless.
Being a gay man, you probably like penises (or at least I hope you do!), so you are going to have some questions about what his crotch looks like. You might want to go online to www.lorencameron.com and buy Loren Cameron's photo book of FTM genitalia, Man Tool. He also has a book called Body Alchemy, portraits of FTMs that include a few shots of postsurgery genitals. Testosterone enlarges the clitoris until it can get two inches long and sometimes more when erect. A metoidioplasty is a minimal form of genital surgery that creates a scrotum with testicular implants and frees up the clitoral shaft so that it drops down and gets longer. This gives an FTM a small penis. Phalloplasty takes tissue from the forearm and skin from the thigh to create a larger penis (again with testicular implants), and there may be an implant of some sort to make intercourse possible.
Let's talk about some sex techniques that some FTMs enjoy. I'm passing on this information with the caution that it certainly doesn't apply to everybody. Kissing and backrubs are among the least scary of these options. Looking at your body, handling your cock, sucking your dick, fondling your balls, exploring your asshole: these are all activities that many gay or bisexual FTMs enjoy. He might like it if you caress his chest; ask him if he can feel his nipples or if he enjoys having them lightly pinched or sucked. Stroking his stomach, back, arms, and thighs works as erotic foreplay. If he wants you to handle his dick, treat it the way you would treat a small penis. Get your thumb and forefinger wet and gently tug on it, moving the foreskin back and forth. If he will show you how he beats off, you can see how hard and fast he likes to have his dick handled. Sometimes there is an especially erotic area on his dick, perhaps just where the head meets the foreskin, or right under the head, that is likely to trigger an orgasm.
If a hand on his cock is okay, a mouth is probably desired as well, and you suck an FTMs dick the same way you suck another genetic guy's cock, except that you won't have to worry about choking. Start easy and build up until you find a level of pressure, motion, and suction that make him respond with growing excitement.
Penetration tends to be more iffy with transmen, but as I said above, some of us like it a lot. Ask him if it's okay for you to touch him anyplace other than his cock. Rather than talking about vaginas, use gender-neutral terms. A lot of FTMs refer to the vaginal opening as the front hole. If he likes having that hole filled up, you can get some lube on your hand and see how many fingers feel good going in and out. The same guidelines apply to the ass. If he likes butt-fucking and you do too, then there's no worries; you'll be familiar with that anatomy. Putting your cock in the front hole does feel different than anal sex. There's usually less resistance. But you don't have to worry about encountering any shit or adding lube every three seconds. An FTM who has taken testosterone long enough to stop menstruating (or who's had a hysterectomy) is in no danger of getting pregnant, so birth control isn't a concern, but preventing transmission of STIs is! Wrap that rascal with a latex condom.
The big turn-off about that front hole for a lot of gay men is the idea that sticking your dick in there makes you straight, that you are somehow giving in to a society that told you not to be gay. But if you really support your friend in his male identity, you will see that this is dumb. He is a guy who has a bonus hole, that's all. And I'm sure you have a few friends who wouldn't turn down the opportunity to have an extra orifice! There are also some misogynist stereotypes about cunts in gay-male culture. But the fact is that a clean pussy just smells sexy, and doesn't taste bad, either. A sexually-active biofag who is used to the aroma of urinals and enemas and assholes doesn't have a right to complain about transmen's pheromones!
If he likes penetration and your dick is not cooperating, you can always use your hands or a dildo. He might like using a vibrator on his dick or vibrating eggs or plugs in either or both holes. If you keep an open mind about the possibilities, you can both get off. He may like to come once or he may have multiple orgasms.
What do you tell your friends if you wind up having a relationship with an FTM, and what would they think? Well, what other people think of me is none of my business, as they say in AA. You can drive yourself crazy trying to anticipate other people's prejudices and formulate responses. Don't jump into a state of defensiveness. Maybe you won't tell your friends he's an FTM. Talk this over with him first. If you do tell them, they will probably go through the same process of amazement and curiosity that you did. If anybody refuses to be educated and treat him politely, well, they can fuck right off, can't they? Such people would probably find a reason to be nasty about anybody you paired off with because they are miserable, green-eyed, catty bitches who can't stand to see anybody else be happy.
How often does anybody have such intense feelings about another man? I think you are lucky to have the opportunity for such a new experience. I wish you and your friend good fortune. There are lots of genetic guys and transmen who have made relationships work