Keepin’ it sleazy with NYC’s queen of Awkward sex stories

You might know Natalie Wall as the bawdy comedian that’s never afraid to share every dirty detail of her personal life. Or you might know her as Brokelyn’s own resident sexpert and astrologist. Or you might know her as the hostess extraordinaire of the beloved storytelling show Awkward Sex and the City, celebrating its four-year anniversary tonight at the Pleasure Chest.

But I know a different Natalie Wall.

For the last two years, I’ve joined Natalie on the road with the Awkward Sex and the City touring troupe, a national extension of the monthly New York City staple. I know Natalie as a one-woman wrecking crew: she’s a travel agent, a marketing whiz and, when four cranky comedians are coming off a cramped six-hour bus ride, the surrogate mom everyone needs, snacks and all.

Together we’ve filled more moderately-priced hotels with farts than I can count.

Before Awkward Sex and the City was a live comedy show, it started as a blog chronicling Natalie’s misadventures dating and doing it as an early-20s something with adult braces. It blossomed into a live storytelling show where some of the city’s most beloved performers recount their embarrassing exploits.

In a city overrun with great comedy shows, Awkward Sex still stands out. For starters, the monthly New York show is held in the basement of a sex shop. During most shows, Natalie leaves up the graphic visuals describing anal play, blowjobs and cunnilingus on the dry erase board from previous workshops held in the space. Plus, the show offers free beer and wine (yes, you read that right), so even the crowd is looser than a recently-fisted … well, you get it.

Ahead of the big anniversary show tonight, I managed to get Natalie to slow down long enough to discuss the evolution of Awkward Sex with the same casual ease we typically share discussing oral.

True to form, she held nothing back.

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How has the show changed over the last four years?

I think I’ve just watched myself become more informed about what sexual inclusivity means. The first show was nothing but white girls, and they were all straight. That was definitely just partly because these were the people I knew, but also that was just the world I knew! So I’ve got to really be humbled and learn about what sexuality means and what sex means to people on so many different levels. I’ve never heard a story similar to another story in the past four years.

The show seems to have become more outwardly political over the years. Was that an intentional decision?

It’s funny you say that because anyone I’ve ever been interviewed by has always been like ‘This is a very political show! This is like a fuck you to society!’ And when I started the show, I never actually saw it as that. It was definitely from my upbringing. I did luck out with family that was very open to female sexuality. But once people started saying [it was political], it was like, whoa, I didn’t realize how many people were jaded and how many people were guarded and how many people were fucked by their upbringing when it comes to sex.

It’s weird when we go to different cities and we’re not 100 percent sure how it’s going to be accepted. In New York City, it will always be accepted, but you go to Boston sometimes, and you get a weird Catholic vibe. Then you go down to South Carolina, and they’re like, ‘We love this! We’re not all crazy down here.’ This is wishful thinking, but I do wish it inspires other people, and it allows people to feel accepted and more willing to embrace their sexual awakening whenever and wherever it happens.

Totally! Even as a queer man traveling with you to other cities, I think what’s cool is, like you said, even cities you’d think are not down, end up being a sort of self-selecting audience. Like, if you’re going to a show called Awkward Sex, you’re coming in at least a little open-minded.

If you come to this show and you don’t realize what it’s going to be about, you’re a fucking dumbass.

What are some of the other differences you’ve seen between the New York crowd and an out-of-town crowd?

I think New York can be a little been there, done that. The other cities are more like “this is amazing!” New York can be a little “I’ve done crazier.”

I feel like you see that a bit with New York comedy and storytelling as a whole. Julio Torres even said something similar when we chatted a couple years back. New York crowds are used to seeing good performances, and you do get special treatment outside the city.

I think you’re right. When you see a show in New York, that’s not like the only part of your night. You have drinks before, then you have a show, then you have whatever’s happening afterward, like two or three things that don’t end until 4am. Whereas when we go to D.C. or Boston or Philly or Richmond, this is that person’s night. This is their event. And that dictates what they’re expecting and how they are.

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The Pleasure Chest is such a cool space. What does doing the show there add to the experience?

It definitely adds an element of sexiness to it. You go in and you have to wait in a sex shop. You get a discount anyway. There are not many people that come to this show alone, so you’re with your girlfriends or your boyfriends or you’re with your significant other, and that’s already getting you hyped to be like “I’ve never seen this sex toy before!” Then you go downstairs, you have your free alcohol, you have your stories, you have a blast, and it’s sexy, and it’s fun, and it feels underground, but it still feel kind of bougie, because we’re on the Upper East Side. I could not have asked for a better venue.

What are some of your favorite memories from the last four years of the New York show?

That’s a hard question, because there are so many. I loved Patti Harrison’s song, that was just an amazing routine that felt so genuine and so unique. She might have done it 1,000 times, but it felt like she had done it for the first time at my show. I truly felt honored. Lucas Connolly has this one story he’s told at both Awkward Sex and Awkward Poop that, I don’t want to give too much away, but it does involve something in his butt. It has such a beautiful hero’s journey to it.

I’ve been at shows where you’ve told stories about losing your virginity, about one-night stands and about pregnancy scares, not only in front of your parents, but also in front of your boyfriend’s parents. What’s that experience like?

I definitely get a weird high from it. I think it’s one of those things where if I have a show like this, then I have to be able to walk the walk. If I can go out and say ‘Oh, I can talk about this in front of anyone.’ I have to be able to really go out there and talk about this in front of anyone. I know if I’m doing this, it helps other people that are like, ‘Shit, if she can do this in front of her fucking mother and father, then I can do this in front of whoever.’ You’re sacrificing a little bit of yourself to show people that sex is OK. If we take away the stigma of talking about sex in front of your family, what else is next?

What’s the best sex advice you’ve ever received?

It has to be from my mom. She told me you need to have sex with multiple people, because you have to figure out what you like. I can honestly say, the first two or three years of my life having sex, there were no actual orgasms, because I didn’t know what I liked yet. You have to go off of what you see in porn, and you follow the lead of your partner. After I had a bad break-up, I had my year of dick. That year was just about figuring out what I like, and I did. I had so many orgasms. I think that’s when I realized my mom was right. You have to fuck over and over again. Then you’ll figure out what you like. And it’s OK to like what you like!

Enjoy some storytelling sexual liberation (and free libations!) tonight at Awkward Sex and the City’s Four Year Anniversary show, 8 pm at the Pleasure Chest.al

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