How to Do Sex

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Ryan O’Connell is a New York-based writer. He likes shoegaze, the Olsen Twins, and figuring out why people do the things they do. Oh, and he tweetsCheck back each Thursday for his latest Call Your Boyfriend column. (You KNOW you have a question. Send it to Ryan.)

Dear Boyfriend, 

Do you have any good sex tips? I have the sneaking suspicion that I’m bad in bed and I would like not to be.

 –Teach Me Your Ways 

Hey secret sex goddess,

I think everyone sort of wonders if they’re bad in bed. I mean, what do you have to go on besides orgasms (which, if you’re a female, might be faked) and your partner explicitly telling you, “You give great head/sex/body.” You never really know. I certainly don’t! One of the few times I ever felt certain I was doing okay in the bedroom was when my then-boyfriend’s best friend got wasted at a party and told me that she had heard our sexual chemistry was “off the chain.” Um, thank you! When someone’s telling their BFF the sex is great, you know they’re telling the truth. You don’t lie to your best friend about sex stuff. You just don’t.

Anyway, I’m no Kama Sutra but here are some things I (and many others, I’m sure) have picked up along the way. Take heed!

1. DO be confident. It doesn’t matter if you have no idea what you’re doing, just fake it till you make it, hon! And if you happen to be feeling like Carnie Wilson on a cheat day and experience an insecure moment about your body, don’t let it show! Because once you’re naked, nothing matters. People are not judging you. They’re just happy to be getting laid. I’ve NEVER looked at someone’s body before sex and been like, “No. Please return to sender.” I remember once hooking up with this really hot guy who I could tell wasn’t comfortable in his own skin and it totally killed it for me. It took him forever to take his shirt off and then when he did, he would cover himself awkwardly. I would never have noticed anything negative about his body until HE drew attention to it. His lack of confidence is ultimately what ruined it for me, not his flab.

2. DON’T be close-minded. When it comes to what you want in sex, nothing should be that embarrassing or weird. Now I’m not saying you have to go along for the ride whenever your partner wants to do something hideously kinky to you (boundaries and safe words were invented for a reason!). However, you owe it to your partner to communicate your turns on and turn offs. I once dated a dude who liked to make out with my armpit, which, you know, wasn’t necessarily MY idea of a good time but he liked it, so that’s all that mattered to me. I totally lent out my armpit to him because why not?! Your goal in sex should be to please your partner and to get pleased, so don’t ever let something as silly as an armpit kiss stand in the way between you and an orgasm.

3. DO be vocal. I’ve mentioned before in a previous column that I HATE IT when people make no noise during sex. It’s so creepy. Dirty talk, moaning, being loud — these are all things that can take sex from “Boring” to “Hey girl hey!” Seriously, whenever you’re having sex with someone and you feel like you’d rather be flossing because it’s so dull, incorporate some noise and words into it. I promise that, good or bad, it will put your head back in the game.

4. Speaking of heads, DON’T be in your head too much. I don’t know about you but I’ve definitely psyched myself out during sex. Like, if I’m taking too long to come during a blowjob, I start to feel guilty for making them work so hard. “They’ve been down there for so long,” I’ll think to myself. “I feel bad. I wish I could come now, damn it!” Then what ends up happening is that I don’t come at all because I’ve spent half of the blowjob suffering from analysis paralysis. It sucks! Sex is the one activity where it’s okay to send your brain to sleep away camp. You don’t need it. It’s excess baggage!

5. DO have sex at 6:00 AM when you’re half-asleep and accidentally have rolled over on a hard dick. My favorite thing is when you take someone home and hook up, but for reasons x, y, and z, you both don’t finish. Then you fall asleep and wake up as the sun is starting to rise and go for round two. You feel like it’s a fever dream because you’re half-unconscious and your breath smells like crap and your hair is fucked. I mean, there are a million reasons why you shouldn’t be having sex right now, which is why it’s so hot. You spent all this time getting ready to go out and look hot. Then you end up having the best sex of your life when you both are barely awake and look like shit. Love it.

So you got all that? Have hazy ghost sex at sunrise, lend out your armpit if need be, behave like a Ryan Gosling even if you’re more of a Steve Buscemi because it all looks the same in the dark, send your brain to the guillotine, and liberate yourself!!!! If any of these tips work, you’re dedicating your next orgasm to me, okay?


Have you ever had a “friends with benefits” situation? If so, how did it pan out for you? What advice would you give for people who are in a “friends with benefits” relationship?


Friend Needing Some Benefits

Ah, finally! A question about Friends With Benefits—a concept that has spawned two terrible romantic comedies and fueled the anxieties of single people everywhere! Is it just me or does Friends With Benefits seem like an urban legend? It’s sort of like a rent-controlled apartment in New York City. You know it exists, but where?

For me personally, I don’t think I’ve ever been in a classic Friends With Benefits situation. In college, I would get drunk with my gay friends and occasionally we’d end up rolling around in bed together, but I’ve never actually, like, looked at my best guy friend and thought, “Let’s hook up on the regular and pretend it doesn’t mean anything more than temporary sexual gratification.” The gay friends I would hook up with were never my close friends, and it’d never happen more than a few times. If we had been closer friends and we started hooking up semi-regularly, I’m sure the lines would get blurred and there’d eventually be a giant throbbing heart where once there was only a dick.

Granted, it’s different for gay men. The attitude towards hooking up with your friends is generally more casual. We understand that we’re both gay, horny, and just need to get off sometimes. That being said, if this person is your best friend in the whole entire world and you keep on falling into bed together, why don’t you two just, you know, date? If you’re having good sex and the emotional connection is there, what’s the difference anymore?

An arrangement such as friends with benefits has nothing to do with maturity level. There isn’t a group of people who can “handle” it…When you have sex with someone new, you’re always just rolling the dice and hoping it turns out favorably.

Sometimes I think Friends With Benefits is just a way for people to do what they want with each other without attaching a permanent label to it. While I I do think it’s possible to sleep with your friend without “accidentally” falling in love, the success of the arrangement depends on the seriousness of the friendship. If this person is on the periphery of your social circle, then fine! Go nuts! If it doesn’t work out, oh well, you two weren’t that good friends anyway! However, if you two are tight, you have to be aware that you could potentially be jeopardizing a friendship and changing the dynamic for the worse. Even if you are confident that you won’t develop feelings, are you positive that your friend won’t either? Don’t take their word for it. People say all sorts of things to get someone into bed with them. As a general rule of thumb: Don’t fuck anyone without the understanding that someone could end up getting fucked.

People like to think that they’re in control of their emotions, and that they can decide whether or not to develop feelings for someone, but it rarely works that way. Whether we like it or not, sex does change things — sometimes a little, sometimes a lot — but you can’t really predict the outcome. I’ve hooked up with people expecting to feel NOTHING because, duh, I’m mature/dead inside! Then after the fact, I am stunned when I discover I’m experiencing these pesky things called feelings. “Get them off me!” I’ll scream to myself, jumping out of the person’s bed. “Swat them away, swat them away!” But they don’t go anywhere. I had sex with someone and now I feel differently about them. Why is this still surprising to me? ‘

In other words, an arrangement such as friends with benefits has nothing to do with maturity level. There isn’t a group of people who can “handle” it because, oh my god, they’ve been having sex for so long so they can separate the physical from the emotional. No. When you have sex with someone new, you’re always just rolling the dice and hoping it turns out favorably.

My advice to people who are dealing with a Friends With Benefits situation is to pay attention to the dynamic. Does this person seem to be falling for you? If so, cease and desist! Or are you falling for them? If you are, you might need to exercise some restraint and stop hooking up to salvage the friendship. Because with every pelvic thrust, you’re getting in deeper and deeper. Yes, I know, terrible pun.

If neither of you are developing warm and fuzzies and the sex is good and the friendship feels stable, then congrats! You’ve won the Friends With Benefits game! Your prize is a person you can bang whenever you want without things ever getting weird. You are a rarity! Gold star for you, honey. Everyone else: Try not sleeping with your friends if you can help it. Life just ends up being simpler that way.