Shannon Boodram's Guide to Navigating Every Awkward Sexual Encounter

All those conversations you need to have but try to ignore? We're dealing with them rn.

By: Meagan Wilson
Photography: Leslie Kirchhoff

Sex, like most things worth doing, can be weird. And messy. Sometimes uncomfortable. But fun! And mostly hard to talk about. It’s only further complicated by past experiences, good and bad, that are unique to every single person—like a snowflake!—and for that reason, certain conversations require various degrees of delicacy.

But we’re mere mortals. Who are we—really, how are we—to tell you how to handle these situations when they arise? Which is where Shannon BoodramShan Boody—comes in, as a sexologist, author, all-around-expert and professional big sister. If there’s a sexual situation that throws you for a loop, leave it to her to deftly deal with it, all with a precise mix of grace, smarts, wit, and realness. So in an effort to figure out the answers to some common sexual FAQs, we consulted Boodram (and deftly deal with them she did).

 

HOW TO NEVER FAKE AN ORGASM AGAIN:

 
“One, you do have to be able to make yourself orgasm. We put a lot of emphasis on men, when a lot of women don't self pleasure. You have to know how to bring yourself to orgasm and know what that path is.

“Also, be patient. I think women have this internal clock in their head, like, 'it's taking too long'. We're naturally empathetic, we think we're there to make their experience good. In our minds, if it's taking too long, the guilt comes in and will stop it. If you don't orgasm in ten minutes, rather than just sitting there and enjoying it, you're like, 'oh my god, I'm not coming, this isn't working'. So they're disappointed afterwards. Ask your partner to be patient, know what works for you, and once you're in the moment, just keep exercising that.

“It's important to have that conversation eventually with your partner. For a lot of us, the problem is you start off faking it, and then we transfer over to a long-term relationship, and the other person will continue doing that exact same thing that they think ‘works’. That's a shock to your partner. Be honest, make it fun. Bring stuff home; bring coconut oil into the bedroom—it's a great lube; touch yourself, guys love that. Make your pleasure a priority, a fun addition, not, 'you're failing, you suck'. How can you make it better for both of you?”

 

HOW TO DISCLOSE A STI TO A PARTNER:

 
“Everyone I know who has a STI knows more about it than the average doctor, which is the great thing about the internet. They know their disease inside and out. You have to provide a lot of information for your partner. You know that when you were diagnosed you went through a ton of emotions: shock, 'my life is over', 'I don't know who I am anymore', 'I can't have sex anymore'. But then you started to learn more, and realize, 'it's not as bad as I thought'. But it took you a while.

“If you're disclosing to your partner, give them that same space. Saying, 'hey I have herpes, and it's Simplex Virus 1, or Simplex Virus 2. I haven't had an outbreak in this much time, you're only contagious at this time according to these studies, here's what I take for medication'. Wanting them to feel like if you continue, they'll be safe, and not limited. Making sure they feel comfortable.

“Practice that dialogue. Most people with STIs, their biggest concern is not outbreaks—a lot of treatments are really good these days, even people with HIV, their virile load is so low. The biggest thing is not dying of illness, it's dying of stigma and shame. A friend of mine who has HIV always says, 'I got this from doing the same thing most people did last night—I had sex with my partner, somebody I loved and trusted, who was carrier, and I wasn't aware of that'. Be patient with people, and don't expect everyone to welcome you with open arms. You didn't welcome your status with open arms.”

 

HOW TO BUY YOUR FIRST SEX TOY:

 
“Know what you like; know what works for you. I’m a big proponent of ‘sex languages’. If you need a lot of friction, you’d get something higher-powered. If you’re visual—I wear a vibrator necklace in public as a symbol of my sexual liberation, and I love that it’s this chic, sleek, silver object, not this pink, vein-y, Nickelodean looking penis. Buy something that doesn’t make you embarrassed: you don’t want to feel like, ‘ugh, this is so gross and weird’ everytime you go into your drawer and take it out. What turns you on aesthetically is important.

“What I would say is foolproof is getting a curved, G-spot toy—people always go for dildos, I don’t know what the point of that is. You need pressure more than anything else. And then a small, vibrating bullet, for the clitoris.”

 

HOW TO BRING UP TRYING SOMETHING NEW IN THE BEDROOM:

 
“The two approaches I like are, ‘I had a dream last night, here’s what I wanted to do, in my dream, I was doing this, you were doing that,’ The second is porn. Having a visual back-up, so the person can see it, because sometimes hearing about it is a little overwhelming”.

 

HOW TO HAVE ANAL SEX FOR THE FIRST TIME:

 
“You need to go mad slow, and have a lot of lube. I think anal sex is not sexy. And that’s not a bad thing—I think it’s a very intimate experience. But it can be excruciatingly painful. Add one finger, two, go back to one. It’s a muscle, so you want to relax it the same way you would at the gym before going into hardcore exercises. A lot of people have a bad first experience because they just go right into it, and then they think it’s not for them. Be prepared to stop if it hurts.”

 

HOW TO FEEL MORE CONFIDENT IN THE BEDROOM:

 
“I’m a big proponent of, ‘meet yourself where you are’. Confidence is not one of those things where you can just feel it. If you have stretch marks that drive you crazy, I can sit here all day and tell you that they’re normal, that every woman has them, that it’s a beautiful thing, but you hate them. So wear a fishnet stocking bodysuit that makes you feel like a warrior princess in the bedroom, so that you’re not insecure about cellulite or stretch marks, so you’re able to focus on the pleasure. Whatever makes you feel insecure, you’ll work on it over time; but in the meantime, support yourself! Put yourself in situations that make you feel good.”

 

Shot on site at Fleur du Mal’s dreamy downtown New York studio and headquarters (you might remember it from this). What’s even more dreamy? Their lingerie.

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