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Sleeping with someone for the first time can bring up all sorts of insecurities and awkward concerns—you’re probably sleeping at the guy’s house for the first time, maybe he’s seeing you totally nude for the first time, and maybe you’re not even clear how strongly he feels about you. Trust us, we all feel this way. Here are 15 things we all worry about when sleeping with someone the first time.
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Should my bra and underwear match?
Sure you don’t match them every day, but does he think you should have at least matched your bra and underwear the first time he saw you in nothing but those?
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Is he used to this type of wax job?
Maybe the other women he’s been with shaved, or left a landing strip, or did a full Brazilian…or maybe he’s into the all-natural thing.
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Is he surprised we’re doing this so soon?
I tried to wait the appropriate amount of dates but was he thinking he’d have to wait longer? And does that make me look to eager? Or even promiscuous?!
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Am I supposed to sleep over?
Or is that a “girlfriend” thing to do? Or if I leave, does that make it seem this was only about the sex for me? Do I ask if I should sleep over? Or does that make me look insecure?
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Am I supposed to leave early?
Should I get out of his hair in the morning as soon as possible? Or am I supposed to wait to have breakfast with him? If he gets up and showers while I’m still in bed, do I wait for him to be finished or disappear while he’s still in there?
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Can I sleep naked?
Is it weird if I just remain naked after we’re done having sex? Or does that make it seem like I’m a bit too comfortable here? If he puts on his boxers, should I put on my underwear? If he stays naked, do I have to stay naked?
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Should I sleep naked?
Maybe throwing on PJ’s or my bra and underwear right after sex isn’t the sexiest thing to do. Maybe I’m supposed to stay naked so that he knows I’m up for another round when he is…
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Do I need to put clothes on to go to the bathroom?
If I do sleep naked, do I have to put clothes on just to go out into the hallway to go to the bathroom? Or would he freak out thinking a neighbor could look in the window?
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Will he think I’m a you know what if I go down on him?
Will he think I give it up too easily if I go down on him the first time we do anything sexual? Will that make him think I do that all of the time?
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Will he think I’m selfish if I don’t go down on him?
Will he think I’m selfish if he goes down on me and I don’t on him, or does he maybe like the idea of just pleasing a woman and earning her going down on him?
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Is it too soon to try weird positions?
Are we supposed to stick to missionary and the “normal” positions the first time, or will he think I’m boring if we do? OR will he think I’m a freak if I maneuver us into a ton of weirder positions the very first time we have sex?
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Is it weird if there’s a lot of kissing?
Is that too “intimate” when we’re not really in a relationship yet? Will he feel smothered if I’m kissing him a lot?
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What do I say to his housemate/neighbor?
When I run into his housemate or neighbor in the morning, clearly seeing me leave in the same clothes I arrived in the night before, do I say something about it? Or act totally oblivious?
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Is my body what he expected it to be?
Did he expect abs? Or maybe my stomach looks better than he expected! Did I wear too much of a padded bra and he is disappointed in my real girls? Or was he pleasantly surprised I had so much up there?
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Can I use his toothbrush/is it weird that I brought my own?
I’d really like to brush my teeth and wash my face, but am I making myself too much at home if I use his products? OR, I know I have a toothbrush and some makeup remover in my purse…will it look like I planned all of this if he sees I brought that?
