48 Hours to Go: First Night Nerves

It’s exactly 48 hours until my next date with Jock. I think it’s going to be *the* date; the one where we fuck for the first time. Anxiety is taking over and I’m overthinking absolutely everything. I’m beyond nervous. That’s how I know I really like him: the thought of being in his presence makes me so nervous that I just can’t think straight.

I’m not prepared for this. I wanted to book a bikini wax but I’m not sure I’ll have time for it. Between you and me, things aren’t exactly looking pretty downstairs. Like, it’s been a little while since One Ball and I last fucked. I’ve let the landscaping slide a little. Not to an outrageous state, or anything like that. But still, I need some work, you know?

And what am I going to wear? It’s a sleepover but are we doing something first? Dinner? Drinks? Do I need to pack heels with my slippers, a dress with my joggers, help a girl out?

I’m so nervous.

Have I said that already? Let me say it a hundred more times because he makes me so nervous. I normally find this part of a relationship super exciting – and I am super excited about it – but I’m also filled with all sorts of other feelings. Guilt over One Ball, for example. And worry: will this new guy break my heart? Will he even get the chance to break my heart? And then there are the nerves because I really, really like him … have I mentioned how nervous I am yet?

But I’m also really very excited about getting my hands on my new boy toy for the first time, and I definitely think we should talk about that feeling a little bit more. First-time sex has always been a real ‘thing’ of mine. A kink? Fetish? I don’t know. Whatever it is, I like it. Those nervous butterflies you get when exploring territories unknown has always been a really sensual and sexy experience for me even when my lovers have been less than thrilling.

I think it’s because you just don’t know what you’re going to get. Is that person going to be good in bed? Well-endowed? Patient enough to learn how to make you really cum? What are their moves? Will they be compatible with yours? Are your moves going to be good enough for them? Will you have as much sexual chemistry with your clothes off as you do with them on?

We’ve covered a lot of ground in our text conversations which have definitely crossed more than a few lines on more than one occasion. He likes his ladies shaved. I prefer to be waxed but I’ll settle for shaved. I’m not a fan of my own pubic hair. If I could permanently remove it, I would.

I also know that he has quite a thing for matching lingerie, but then again, what person wouldn’t want their partner to dress up all sassy and matching and sexy for them? We’ve not really gone into the specifics but he did tell me that he thought booty shorts were hot. So what do I wear? Should I go out and buy something booty shorts-based especially for the occasion? Or do I just pull out that sexy little black lace number; bra, panties, stockings, garter belt, all matching and hot as fuck? He said he likes pink too, but will he appreciate the neon pink set I’ve got?

And what about my self-harm scars? He’s definitely going to see those unless we have sex at night, with the lights off. Do I tell him about them beforehand, or shall I just pretend they don’t exist and hope he doesn’t spot them and want to talk about them? He already knows that I’m quite shy about my body and that I do better with the lights off, but what about the morning after? Will he be able to see my scars in the morning light?

And moving aside from the lingerie and self-harm scars, which outfit shall I wear? Are we going out or is he just taking me back to his place? Should I wear heels? Are his housemates going to be in or can I just go full sexy-slut, nothing on but matching lingerie beneath a belted jacket? Is this a casual event, or a smart one? Little black dress and heels, or jeans and a comfy tee with Converse?

And should I grab a bottle of wine for us to drink? Or is that his job? Should we both just grab one each just in case? Is one going to be enough? I’m nervous and I think a few drinks will help, but I don’t want to get drunk. Not out-of-control drunk, anyway. Or blind-drunk. It would be nice to remember the date and our first time fucking, you know?

And let’s talk about the fucking a bit more (because why not?). Do I go into the date with the expectation of fucking him? Or does that make it too easy? Should I hold out for the fourth date as I originally planned? Shall I hold back and play it cool, making him work for it and really driving him nuts? I know he likes the thrill of the chase but honestly, I don’t know if I have enough self-control to fend him off if he tries it on. And that reminds me: condoms. Do I just buy regular condoms and hope they fit? Or should I go prepared with a range of types and sizes just in case he’s rocking a super-schlong/micro-penis/allergy of some kind? I’ve got 48 hours to get my shit together … please help me.

It feels like I know NOTHING about dating.

Wish me luck, peeps.

I have no fucking clue what I’m doing.