I Went to One of Times Square’s Last Remaining Peep Shows

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Remember Saturday, April 18th? Sure you do. It was the first gorgeous spring day in NYC when you all wore shorts and had boozy brunch outside and I couldn’t get a cab because the rest of New York was in them. Well, while you were out basking yourself in sunshine and unlimited watered-down mimosas, I was basking myself in the gritty underbelly that is Times Square’s last few remaining peep shows... and then spent the next 36 hours showering.

Ryan Craggs/Thrillist

One might think that the lingering remnants of Times Square’s famed peep show culture would be seedy, dirty, and altogether a little disturbing. But in reality... it is actually all of these things. Combined. And amplified. To an extraordinary level. We all have heard the storied past of Times Square in the 1980s, told to us in hushed, reverent tones from the boozed-up guy at the back of Jimmy’s Corner. We’ve heard the decrepit troubadours sing their lyrical poems about all the hookers, drug addicts, and a plethora of peep shows that Giuliani did away with in the mid-'90s and replaced with Olive Garden, Neil Patrick Harris, and all the M&M's (thanks a lot, Giuliani). Still, tucked among the life-sized Spongebobs, Jersey Boys, and a Forever 21 that extends to the high heavens, exists about 10 remaining peep shows in Times Square, bringing the hardened New York old-schoolers (ahem, and yours truly) a taste of NYC’s fabled, folkloric past: naked ladies undulating in tiny, private booths while you sit awkwardly for the longest two minutes and 19 seconds of your entire life in a chair that was last Lysol’d the day before never. Ahh, New York.

I made my way to 8th Ave between 43rd and 44th to the Playpen, a sex store-meets-entertainment house that shares the block with a Harlem Spiritual tour company and a Starbucks. Past the first floor array of condoms, tassels, and sex toys du jour, I made my way to the back of the store to an elderly gentleman guarding the staircase to the upstairs den of depravity. "Hello sir, I would like to see the show, please." He directed me to the third floor. Following the GIRLS GIRLS GIRLS banners, I climbed to the top.

Flickr/John Chandler

At the top of the steps sat three, full-figured ladies chattering away in husky voices, their pink, fish-net outfits leaving little to the imagination... I’m guessing 3pm on a Saturday afternoon is not peeping prime time.

I’d imagine that typically you could choose your own lady, but for me it was the other way around. Ebony liked me from the very beginning and beckoned me toward her. Not one to be rude (and quite honestly plain terrified), I accepted. $30 gets you the basic strip show, while a cool $40 will grant you access to the elusive self-pleasuring room and the company of two women. Saturdays typically aren’t my days for self-pleasuring in front of two middle aged strippers, so I went with the basic package. Ebony started peeking into the six private booths to find one that was "clean." This is exactly what you want to hear at your first peep show.

"Okay Meagan, because I like you I’m going to show you something that usually costs extra"

When she found one that suited her, she sat me down on the questionable chair and went around to the other side of the plexiglass window. I inserted my money into the electronic slot and the screen over the window raised itself, revealing Ebony’s very bare ass bopping up and down. Alright, so I guess we’re just diving right in. Two minutes doesn’t leave a lot of time for chitchat. This all would have been well and good if not for the fact that Ebony was about 18in from my face and kept saying my name over and over again while she rubbed various parts of her body. She could very clearly see my expression, which I hoped looked turned on but could probably be more accurately described as hopelessly awkward and uncomfortable.

"Okay Meagan, because I like you I’m going to show you something that usually costs extra," she helpfully offered. Fan-f***ing-tastic. Can’t wait.

Flickr/Gerry Kollmuss

I told her I thought it looked very nice. There may have also been a thumbs up involved.

As the final fanfare died down, I felt a wave of relief. It was almost over. "Stand up, Meagan," Ebony commanded. Umm... what? There’s more? I didn’t want to be argumentative in the tiny booth on the top floor of a Times Square peep show so I did as I was told.

"You have very nice thighs," she told me. "Lift up your skirt to let me see." For a hot second I blushed with pride and actually put my hands to my skirt, contemplating returning the favor. All of a sudden the curtain rolled itself down and Ebony opened the door telling me for an extra $20 I could continue the show in the back room.

Sh*t. She got me. She never liked my thighs. She didn’t care about what I had going on. I was just a dollar sign, no better than all the other chumps who have wandered into these rooms looking for a little validation and a couple minutes of attention from a naked stranger. Times Square 1, Meagan 0.

I think this will probably end my career as a Times Square peeper. No regrets (actually ALL the regrets), but I’d like to limit my sexual adventures to more modest endeavors like actual sex, in the privacy of my bedroom. At the very least it was a lesson in the history of our great city and a cautionary tale about what happens when you decide to opt out of bottomless brunch on the first beautiful Saturday in New York. It will never happen again.

Reach out to us at sex@thrillist.com with your sexiest stories, worst dates, nakedest parties, and any and all questions you want answered or looked into about sex and dating in New York City.

Meagan Drillinger is a freelance writer for Thrillist. She’s still in the shower. Follow her on Facebook, Instagram and Twitter at @drillinjourneys.