The Riskiest Places to Get Off (And the Surprising Lessons They Taught Me)

Why pay for a city tour when you can get hands-on with urban exploration? (Literally. Quite literally.)
Get hands-on with urban exploration

Unconventional masturbation spots can lead to unexpected discoveries — whether about subcultures, niche hobbies, or even yourself. Here are some weirdly educational possibilities:

1. Abandoned Office Building (After Hours)

Unexpected Lesson: Urban exploration, local history (finding old paperwork), or how quickly security actually responds.

Bonus: You might stumble upon a time capsule of 90s corporate culture.

2. Public Park (Deep in the Bushes at Night)

Unexpected Lesson: Nocturnal wildlife habits (raccoons are bold), or that your city has a secret midnight frisbee golf league.

Bonus: Overhear conspiracy theorists debating aliens.

3. Rooftop of a Parking Garage

Unexpected Lesson: Astronomy (great star-gazing), or that your town has an illegal rooftop party scene.

Bonus: Find a forgotten joint left behind by a stressed-out office worker.

4. Church Bathroom (During a Weekday)

Unexpected Lesson: Overhear a surprisingly intense AA meeting or the secret sins of the choir rehearsal.

Bonus: Discover the anarchist nun who runs a zine distro.

5. Behind a Restaurant Dumpster in an Alley

Unexpected Lesson: Kitchen workers’ secret smoke-break gossip (chefs are drunk).

Bonus: Learn how to repurpose food waste into compost.

6. Empty Movie Theater (Midday Weekday Showing)

Unexpected Lesson: Film projectionists still exist, and they’re bitter about digital.

Bonus: Discover a cult following for terrible B-movies.

7. College Library (Restricted Archives Section)

Unexpected Lesson: Radical 1970s feminist manifestos or how to forge a rare book dealer’s signature.

Bonus: Find notes from a decades-old student affair in the margins.

8. Laundromat (Late at Night, Top Loader)

Unexpected Lesson: The underground economy of people who trade vintage band tees.

Bonus: Learn which detergents are a scam from a retired chemist doing his socks.

9. Empty Train Car (Last Stop of the Night)

Unexpected Lesson: Hobo graffiti symbols and their meanings.

Bonus: Overhear a conductor’s secret folk music side gig.

10. Storage Unit (Rented Just for This)

Unexpected Lesson: The bizarre subculture of storage unit auctions.

Bonus: Find a box of 80s love letters from a failed punk band.

Our takeaway:

If you’re confident no one can tell what you’re doing in the cereal aisle, relax and take a look around. You might discover one of our city’s weird microcultures.

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