15 Awkward Things About Sleeping With A Guy For The First Time

It doesn’t matter if it’s a one-night stand, a casual friend with benefits, or the start of something real—the first time you have sex with someone new, it’s awkward as hell. Here are some of the worst things about it:

  1. How sometimes it’s planned and sometimes it’s not In a perfect world, two people are on the exact same page when it comes to sleeping together, but that doesn’t always happen. It can be incredibly weird if one person shows up totally wanting it and the other person was planning to actually watch Netflix and legit chill…
  2. The panic if you haven’t “prepped” properly The first thought for most girls when we realize sex is about to go down is desperately trying to remember if/what areas we shaved that morning. Some guys don’t care about maintenance, but we can’t help it that we want to be pretty everywhere even if he won’t notice.
  3. Wondering if he manscaped For those of us that prefer clean shaven lower halves on our men, not knowing whether or not he did his prep work can be just as stressful. What if we’re hot and heavy and then I’m totally turned off by his lack of cleanup?!
  4. The lights on/lights off debate When you’re hooking up with someone new, you usually haven’t had the talk about what to do with the lights. You can usually ask and play it off like a joke or just get up mid-make out and turn the damn thing off, but there’s still the moment of hesitation that’s unavoidable the first time you sleep together.
  5. Praying he has protection if you don’t Ah yes, the condom conundrum. You don’t want to bring a whole stack and appear too easy, but if you forget them and he doesn’t have any either, you’re SOL. It’s even more awkward if he whips his junk out with no condom and you have to grab him by the shoulders and be like, “Hell no, dude!”
  6. Is foreplay still a thing? When he’s going for the home run it’s hard to know if he’s cool with stopping at other bases or not. Should you take your time driving him nuts with that blowjob or is he expecting you to skip to the main event? Is he going to give you any attention at all beforehand? (P.S. the answer had better be yes.)
  7. Having no clue how long the sex will last When you’ve never had sex with that person before, you have NO idea what to expect in terms of duration. How are you supposed to know if you should run to the bathroom first or maybe grab some crackers if you don’t know whether you’ll be done in five minutes or two hours?
  8. Being self-conscious about every little thing Even if you’ve already done “everything but” with someone and feel otherwise comfortable with them, sex is so intimate and so exposing that it’s totally normal to be uber self-conscious. Worrying about how your body is jiggling, how different areas are smelling and what he thinks of the moans and spasms you can’t control (hint: he loves them) can feel pretty awkward the first time around.
  9. What if I don’t finish? Sex with each person is different and what worked for you with one guy won’t necessarily work with another. Hopefully whoever you’re sleeping with cares about your orgasms to help you get there, but it’s hard going into a new situation not knowing whether or not you’ll get to enjoy yourself too.
  10. What if he doesn’t finish? It’s true that not every guy gets off from sex every time, but it usually happens—and being the girl when he doesn’t finish can be traumatizing for your ego. If it’s your first time with someone new and they can’t come, you’re bound to feel super awkward. Just make sure you talk about it (so weird, but so worth it) so he can reassure you that it wasn’t anything you did (or didn’t) do!
  11. If he does, WHERE?! If you haven’t had the conversation about where you want him to cum (inside, chest, stomach, etc.) and you’re already halfway through sex, it’s going to be a very hectic few seconds as you scramble to make your preferences clear. Everyone is different, so make sure you have a game plan.
  12. Having to clean up after yourselves Depending on where he decided to land his load, one of you (preferably him) is going to have to take care of the mess. This might be the most awkward part of the whole encounter, not knowing whether he wants tissues, towel, wet wipe, etc while he’s lying there totally exposed.
  13. Not knowing what to do afterward After everything is said and done, you might be unsure what happens next. Do you cuddle? Do you spend the night? Do you say thanks and give him a little pat on the back? HELP!
  14. Wondering if it’ll happen again Sometimes once sex has become part of your routine with a new partner, it’s expected all the time. Other times, it’s just an added bonus on top of how you usually fool around. Either way, you’ll have to have an awkward conversation about what it means going forward.
  15. Wondering how it changes things Though not always true, often times sex is the thing that takes relationships to the next level. Whatever you do, make sure you’re both on the same page. Worst case, you decide not to do it again, but if it was freaking awesome, you’re in for lots more fun in the future.
We only have one chance to live this life and I'm making the most of it. I'll make plenty of mistakes along the way but each one will send me further down the right path.