Miss Information
A closeted guy told me he wanted to experiment with me. How should I proceed?
by Cait Robinson
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Dear Miss Information,
On New Year's Eve, I met a closeted bisexual guy in his thirties who told me that he wanted to try fucking a guy. As a twenty-something gay guy myself, this is a fantasy realized. What is the best way to navigate the situation? Should we discuss beforehand what he's comfortable doing? I'm quite a sexual person and would love to be able to play out some fantasies on a newbie. But I don't want to get into this situation and have him to freak out when it comes down to having sex. When we kissed on New Year's Eve, it was the first time he'd done anything sexual with another guy, and he was very keen. What to do?
— Un-Closeter
Dear Un-Closeter,
I love that you are taking this guy's sanity into account, even if it's just for the sake of fulfilling your fantasy. It's a responsible and generous approach, and one we should all take with our partners, no matter how experienced.
It's a great idea to talk to him first to get a sense of what he expects/wants. You can also keep your antennas out for any hint of weirdness (i.e. any hesitation, nervousness, Republican senatorial affiliations, etc.). Better plans are laid while the clothes are on. This way, by the time you get into a dark room, you know he wants to be there and he knows you're looking out for him. That kind of trust will reap dividends.
When you're in the moment, keep an eye on him. You don't need to ask if he's okay every ten seconds, but get consent before anything big, and keep communication lines open and light throughout. Also stay tuned in to nonverbal cues. If you are afraid of overstepping bounds, let him take some agency: put yourselves partway into a position, then let him take the initiative on the last bit. You also may want to arrange a "safeword" if you don't think the standard "ow" or "wait, stop" will work.
Before you go in, be clear on how you will react if he panics, backs out, or otherwise seems hesitant. This possibility may be remote, but it is nonetheless a possibility. If he chickens out — explicitly or implicitly — it's game over. Under no circumstances should anybody be wheedled into a sexual act they are not prepared for, period. If you think it will be hard for you to respect this, or that the temptation to whine/beg/plead will be too strong, do both of you a favor and bow out now. Otherwise, you run the risk of being both his first and his last.
Commentarium (14 Comments)
I hate to be wet blanket, but honestly, the couple in the second letter should just break up. If they really feel that strongly about each other, they can remain on friendly terms, and maybe if they wind up living in the same place, then they can try a relationship again. Trying to keep this a relationship afloat while he tries to launch his career, and while she goes to school, is being a servant to too many masters. Neither one of them will give the rest of their school/work the focus it needs because they are distracted by the relationship, the relationship will probably eventually buckle under the stress of separation, and they'll wind up regretting not putting more into the other aspects of their lives. They both sound pretty young, and this relationshp sounds like a limiting factor on their individual potentials.
LW#2: The truth is, you are less important than his career right now. He has made that decision, and frankly, it's probably a pretty wise one. You have also made the decision that he is less important than your education --after all, there are schools in Florida, yeah? Neither of you are wrong for these decisions/priorities. But it's not benefitting anyone to pretend that your relationship is or should be #1 on both of your minds.
Now, as to whether or not you stay together: That's really up to you two. It sounds like you won't be getting together sooner than four years from now. If that sounds unbearable, you should probably just end it as amicably as possible, as Been there suggested. And you don't sound selfish at all, but you do sound a little bit immature, unwilling to accept that in life, there are things that you need to do that are more important than the things that you want to do; you can't just determine for your boyfriend's life and decisions for him — as much as he may love you, he has to look out for himself and his future.
When you're going for your first real good job after college, sometimes you have to move cross-country to get what you really want. Unless you're living in a place that happens to have a lot of the kinds of positions he's looking for, it may not be the place where he wants to "set roots." Give him a chance to explore all of his options, and if that's too hard, you may want to consider opening your relationship or ending it.
When you catch yourself thinking, "if he loved me, he would _________," you're going down a dangerous path. You're probably thinking about following some script you have in your head and not looking at the real, loving person in front of you.
He is - wisely - focusing on creating the foundation for an adult life. He needs to do that to feel successful and be self-sufficient, which will make him a better partner. He wants to be with you and even cries when it's time to part. He sounds like he is worth waiting for if you can realize he loves you in his own way, not in the way you thought someone would when you were little and dreaming of your future life. I'm not trying to be hard on you. Navigating an adult relationship is hard because it often means giving up long-held fantasies for what will eventually be a better reality.
Distance is hard but not insurmountable when two people have a clear vision of what they are working toward. If you aren't ready to give up the script in your head or believe you will never be happy unless that script is followed, it might be time to break up. Good luck.
Relationships work when two people share a strong emotional/romantic connection, and when the timing is right. The timing may not be right for the couple in the second letter. LW2, if you do end up growing apart and away from each other, try not to blame yourself or him. It sounds like you care about each other, but you may be growing into different people, with divergent paths. You have to be true to your own vision of your future, and let him do the same, and then see if those visions eventually line up. It will either happen or it won't, and there's no way to force it.
Thanks to all of the positive good advice in the comments, and from miss info. It was really hard to compose a letter where the most important bits of the story came across.
As for schools in florida, Yes there are schools in florida. I currently attend one, But it is still far from him, and it is the one my scholarship paid for. As for the script in my mind, there isnt one. I'd just like to point that out.
Since writing in, my boyfriend and i have sorted this problem out for ourselves. He was the one to bring the issue up, without myself mentioning it. He has changed his goal from a Desk job that he apparently hates, to something he enjoys doing, and is even a movable career. This first year I am sorting out my life, and he is sorting out his. Our relationship is still intact and he is moving in next year. Even if it takes a little longer, i feel better knowing when I will get to be with him, rather than having no idea at all.
My biggest issue is that I didnt bring up how i was feeling about the distance because I was worried it would come across as selfish or needy. I was afraid that I would unintentionally be giving him a choice.
If this message sounds immature also, I apologize. I'm just not very good at putting down my thoughts and feelings into a composed form.
Well hell, no matter what anyone says thanks for updating us on the letter. It's super rare that happens and it's always something I've wanted from these things.
I bet the "bi" guy in the first question has banged dudes in the past.
Possibly. But then everybody has a first time.
Something to remember is that that can be real physical danger with "straight" guys who veer into gay territory. I've seen it myself if milder forms: guys who come onto you when they're horny only to angrily accuse you of seducing them the next morning.
A gay guy I knew started doing coke with a 20 year old "straight" dude at a party. They went upstairs and started getting frisky. The gay guy went down on the kid and at some point the kid freaked out and started to beat the shit out of him. Left blood on the walls of the bedroom and he had to be hospitalized.
So, be careful out there.
Yeah, I've got mixed messages from this guy. I think he has some unresolved issues to get through before I jump into anything sexual. Didn't hear anything from him post-NYE. Although this weekend I woke up having received a drunken sex text from him during the night and a second sober text apologizing for said message and that he had drank too much blah blah blah. I think I may well steer clear!
I am bi and agree with being careful. The first time I ever got together with another guy he was cool about asking at each stage if I was comfortable. But he also knew that I was into experimenting. I have just heard too many stories of straight guys freaking and something bad happening.
They are afterall, straight. I guess.
Ok, so i'm wondering in the first question, why the gay guy just didn't do the deed that night (New years eve) with the bi guy? I mean, why not? Now he's in this mind-bending conundrum on how to get back to the SAME point he was with bi-boy on NYE!
As far as Too Selfish for Love goes, if he has enough money to pay his bf's bills for month (or until he could find a job), why not just use that money to continue visiting him once a month? OR, is the REAL reason, he wants to lock his BF down because he's having feelings of insecurities due to the long-distance (and his BF's new zeal for wanting to work in his chosen profession).
Just sayin'!
Long distance relationships are a bad idea unless both parties feel very strongly about them. From the letter it doesn't strike me that is the case here.
The only ones I know of that have worked are where the parties just feel like they will die if they are apart, but are responsible enough to stay focused on school/work and hence not move.
My wife and I lived 3 hours apart at the beginning, and it took less than six months beofre I was looking for a job in her town.
Now you say something