Losing your virginity, gay sex, and other worries

I lost Nanowrimo this year due to an insane November, but now that I'm off for the holidays, I've been trying to work on it again. And I've been enjoying it, but I've kind of gotten into a rut. I think I need someone to talk me out of it. Or give me some advice.

See, one of the major plot points of my novel is that my MC is still a virgin... at 31 years old. He was 18 when he adopted a kid and devoted his life to raising him, working two jobs to support him and everything. Now that kid is 13 years old and introduced him to the father of his best friend, who is also a single parent, and the two of them end up getting into a relationship. This is my MC's first time in a relationship with another guy -- he had a few "girlfriends" in high school, but that was all just for show, as he was too scared to let anyone know about his sexuality, and he could never bring himself to go very far with them. Things have been progressing nicely enough, and I'm just starting to get into the sexual aspects of it. My MC is insecure about his virginity, and the fact that he came prematurely when the two of them were making out isn't doing much for his confidence, although he feels a little justified in his premature ejaculation, since it was making out of the up-against-the-wall-grinding-against-each-other variety.

So here's the part where I'm conflicted. I want there to be a scene where things get dangerously close to sex -- my MC's going to be having those first-time jitters, and he's as nervous as all-get-out, and it leads to his partner finding out that he's never done this before. Being a respectable gentleman, his partner wants to back off because he senses that he's not ready for that step yet and it's too much too fast.

And eventually, I do want there to be that happy, romantic sex scene --the big climax, if you will-- after which my MC can shout to the world that he's not a virgin anymore and generally be an embarrassment to the both of them.

But I think my problem stems with the fact that it's hard to define just what sex is and what it means to lose your virginity. I feel like it's such a fuzzy line. And that is a debate that occurs with heterosexual individuals too -- people who consider themselves virgins in spite of the fact that they engage in oral sex, and that sort of thing. Now, my MC is obviously a virgin because he's never gone past above-the-waist groping and that was an incredibly awkward thing for him when he was back in high school and was dating girls because he felt obliged to. But how do I judge that defining moment when he feels satisfied that he's "lost" his virginity?

And to open up a whole new can of worms, there's the whole anal debate to throw into the mix. There's all these societal ideas that penetration is the only form of sex, and I'm not entirely sure whether or not my character goes along with that frame of mind. It's entirely possible that he does, but it's also possible that he might not be into anal, which makes it even trickier to build up to that climatic moment because there isn't... a set goal, maybe?

Ugh. It's all just been bothering me, and it's hampering my writing. I don't know where to take this. If you've made it this far through my rambling, perhaps you could give me some advice on how to approach this issue?

I made it thru all the rambling, but still not sure what your question is exactly. Virgin just means you haven't done it, whatever "it" is. "It" could be defined about anyway you like. I suppose the obvious definition would have to do with penetration, but it could be any other activity you might want to use. I keep thinking about the idea of virgin lips, meaning you've never kissed or been kissed. But that could also be defined In a gay sense, meaning someone who's never kissed or been kissed by someone of the same sex, if you wanted to make that distinction. Also, in gay sex, note that it's possible to be a virgin at penetration one direction, but not in the other. (if you're a bottom, you might have a lot of experience at being penetrated, but could still be a virgin at having penetrated someone else.). So it just depends how you want to define it. The important thing, I think, is to avoid getting hung up on labels and definitions, and concentrate on your characters and what they're willing and ready to do and what type of activities make them uncomfortable. I'm pretty sure that even at age 31, it's not going to be really odd to be a gay virgin. Some people just take longer to get started. And I imagine if his lover really, truly cares about him, that won't be a problem. But, see, now we're getting back to character issues and not definitions of what constitutes virginity. Your character, it sounds like, is going to be hesitant to take that BIG step to below-the-waist activities, and will most likely need a supportive partner. But if he really wants to take that step, it can happen. It might be awkward, or difficult, but to me that's half the fun of writing, is trying to recreate that incredible mixture of emotions that come with big changes.

Is any of that at all helpful? I'm still not sure I got to your real issue.

How do I judge that defining moment when he feels satisfied that he's "lost" his virginity?

I'm following up here with what I decided was your principle question. I think this is going to be a very personal decision on his part as to what constitutes virginity. And everyone will have a different answer. So only he will "know" when he reaches that magical moment. He'll probably have some "goal" or some definition of what makes him a virgin, and at what point he no longer considers himself one. As I said in my last post, it will most likely represent a fairly significant step for him. I'm tempted to give an example, but everyone is different, and what I think might be a good example for a defining moment might not be such a good definition for someone else. So.... I say ask your character. What do they think? What step do they think they have to take to lose their virginity? And yhat's your defining moment.

I think the first thing you need to do is just into your characters' head and just ask him...how does he define his virginity? Is it when the genitals are touched erotically? Oral? Penetration? All are fair game? I think once you climb over that hurdle everything else will fall into place, so to speak~