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Panicking because of my first meeting (and possibly first time sex with a guy)

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So, I met this really nice guy on a dating website and it's been almost a year now that we were in touch. We tried to meet earlier, but because of our working schedules things didn't work out. But now that we both will be able to take our annual leave from work, we will be meeting for the very first time.

He's visiting from a whole different continent and I don't want to make him feel at unease at all. In case you're wondering, he's the bottom and I'm the top. He will be my very first guy to have sex with, and this is making me panick; the simple fact that I might screw things up and not live to our sexting, especially that I have only been with girls (vaginal sex) and I didn't really like it so I'm not that experienced in that either.

He's older than me, and is way more experienced when compared to someone like me. One other concern is that I have a very thick and above average length meat, which I'm afraid will prove as difficult for him to take. I really care for him and I don't want this to be anything that he regrets, actually I want our first time having sex to be something that we will never forget (in a good way of course).

So my question is, assuming that he's staying for a week, should I just wait until he asks for sex or should I present the idea myself? Also if we both got into it and I'm about to go in, what should I expect/do to make sure this will be something that we will enjoy?
 
Virgin here as well, but I think I'm still justified in saying that if you want to have sex, there shouldn't be anything wrong in asking or initiating.

Obviously, it probably shouldn't be the first thing you say to them (though who knows they might be into that kinda directness?) but it's not a bad thing to be honest about what you want and start things. Hopefully the opportunity to bring it up will arise organically but even if it doesn't that's okay.

And conversely, if you find yourself not wanting to have sex for any reason it is also still okay for you to hold off until you are ready.


Again, I can't speak to what you should do because I don't have any experience. But I can tell you what I would do and why.

I find knowledge really empowering. So to make myself feel more secure, if I was worried about not knowing what I should do to make the sex we might have special and enjoyable I would talk with my partner about my reservations so they could help me get outside of my head and do a little pre-planning so I don't feel so overwhelmed with not knowing what to do.

I might also do a little independent research as well about some common do's, and most importantly, don'ts.


Have you talked with your partner about any of this stuff? Like how you're worried a bit about hurting them? I think it'd be good information for them to have. Maybe they'd know to pack a butt plug or an array of dildos to prep themselves to minimize the risk of being hurt. I'd imagine that'd make you feel less anxious.


Last thing I want to say is that I think it's really admirable that you're putting so much consideration into your first face to face visit. Sounds like your partner is really lucky!
 
I agree with seacore, don't get all inside your head. You are giving him your cherry. He'll respect that too. Be excited, not worried.
 
Thank you SeaCore for your reply.

I have done a light research on the do's and don'ts as you mentioned, but they were very general and mostly intuitive. I just thought that someone with an experience similar to mine would come across this thread and maybe calm me down a bit about it.

We have talked many times before about it, especially when he stated that he feels somewhat "intimidated" by the size of my erection and we kind of set some rules for when we are in bed. We never got to be in bed since then, but I think it's a good idea to bring it up again and talk about it.

And thank you so much about your kind remark, but he IS a great person, and taking care of him is my top priority.

- - - Updated - - -

ballcaphair said:
I agree with seacore, don't get all inside your head. You are giving him your cherry. He'll respect that too. Be excited, not worried.
Click to expand...

You are definitely right. I guess I'm just overthinking this. I can't deny the excitement, but I do get a little anxious about it and I should talk to him about it again.
 
Sexting sets up expectations. You might want to refrain from sexting when you haven't even met the guy yet. So far, is this all just typing (meaning, on a screen)? If that's so you have no idea what the person will be like IN PERSON.

Have you tried Skype yet or FaceTime or something like that? You will at least have seen his face (and presumably, since you went ahead and "sexted" each other - his body) so there won't be any surprises.
It is easier to have sex with someone you've had FaceTime with than someone you haven't seen their face or body (in realtime). Doing that, their body language gives you cues about them - and gives them cues about you.

This was the advantage before the Internet: you had to actually BE there in person (well, on the phone, too), but usually you were face to face with whoever you wanted to have sex with. You'd either like how they presented themselves or you didn't. Sexting is - a LOT - a fantasy world (even with pictures), and I can see how it can create expectations people then have to worry about meeting.
 
mcbrion said:
Sexting sets up expectations. You might want to refrain from sexting when you haven't even met the guy yet. So far, is this all just typing (meaning, on a screen)? If that's so you have no idea what the person will be like IN PERSON.

Have you tried Skype yet or FaceTime or something like that? You will at least have seen his face (and presumably, since you went ahead and "sexted" each other - his body) so there won't be any surprises.
It is easier to have sex with someone you've had FaceTime with than someone you haven't seen their face or body (in realtime). Doing that, their body language gives you cues about them - and gives them cues about you.

This was the advantage before the Internet: you had to actually BE there in person (well, on the phone, too), but usually you were face to face with whoever you wanted to have sex with. You'd either like how they presented themselves or you didn't. Sexting is - a LOT - a fantasy world (even with pictures), and I can see how it can create expectations people then have to worry about meeting.
Click to expand...

We started off by texting, but a couple of weeks in we began to use Skype. We haven't actually done "dirty camming", so the sexting was all via typing.

I know that not everyone gets how this feels, concerning that we have never actually met in person yet we developed feelings toward one another, but it happened. And it took us a while to feel that, it wasn't a random "I love you" that got us where we currently are. Complications because of borders and VISAs are what's getting in our way to meet, we could have met long ago to wipe away any bad thoughts either of us has about how it will feel when we're in person.

I know for fact that while sexting things are just taken to levels they might never reach in real life, and I'm more concerned about how well I will do than about him. I have my own insecurities -and so does he of course, but having not been with a guy in bed before is what scares me the most.
 
take your anxieties, put them in a metaphorical box, and push the reset button. that helps me.
 
So you HAVE Skyped. That's good. You've looked each other in the eyes. So it's been more than sexting.

Just take things slowly then. I met my British boyfriend on a website, and even when he was coming to the Northeast, and I volunteered to put him up, I didn't expect we'd have sex. I hadn't any idea how I'd feel about him until I saw him, besides which, my offer was void of any expectation. I was just being hospitable, since he'd never been to Connecticut. we just talked the first couple of days he was here. I didn't kiss him until the 3rd day, which pleased him. He didn't feel rushed. Maybe that won't work for you, but you do have choices here. You can just kiss or hold hands for a day or two. You can even admit you're feeling excited but anxious and ask how he's feeling. Communication is really, really undervalued nowadays.

As I said, Expectations still create anxiety. Don't exacerbate things by being in your head all the time and then by rushing into sex.
 
Talk to him, explaining and questioning like you are doing here.
 
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