A Tourist's Guide to the Prostate

Hey, cutie. Just wanted to let you know that this story originally ran in our March issue, so if you like what you see, you should probably snag a hard copy ASAP. Bye!


The prostate, a walnut-size gland right below a penis-haver’s bladder, is one of the most erogenous zones on the worldwide pleasure map. And while its main “industry” is helping to produce semen, the trendy-chic reason to pay it a visit (through the rectum—no direct flights, bb!) is because it can feel really effing good for your partner. Like, oh-my-god-I-forgot-my-own-name good. Which means that even as a nonlocal, you can still be part of an explosive experience. After all, sex is at its most deeply satisfying when both parties feel new levels of pleasure.

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Not for nothing, we also need novelty where we can get it right now, and this opens up so many erotic options: Next-level orgasms! Different power dynamics! New toys! Temperature play! So until real travel is a go, making this ~special occasion~ trip can fill ya both with happy memories. Bon voyage!

What to pack

Lube is to prostate action what sunscreen is to an island getaway: absolutely fucking necessary. You’ll be traveling through the anus (more on this later), which doesn’t self-lubricate like the vagina, so you need lots of lube. Oil- or silicone-based anal formulas are best, but make sure you’re not using them with any silicone toys or latex condoms/gloves,
as they can break down the material. There are also plenty of water-based anal lubes. Whatever you get, the thicker the formula, the better.

If you’ll be bringing along a toy, make sure it is curved specifically for prostate play and has a butthole-safe flared base or loop for easy removal. (We’re all trying to avoid trips to the ER right now, remember?) There are tons of prostate massagers that are specially designed to target the area, and different textures and functions = more sensation. Glass and steel toys can be heated or cooled for extra sensation (run them under cold water or warm them up with body heat). Icicles’ No. 46 toy (that’s it right under here) is made of glass, so it works with all kinds of lube. And any toy with vibration can help relax the area—and will feel good for both of you if kept in during P-in-V.

Icicles No 46 Curved P-Spot Glass Butt Plug

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$29.99

How to get there

You can take the scenic route and start off slow with a perineum massage (that’s the external spot between the testicles and anus) during a hand job or oral sex, suggests sexologist Megan Stubbs, EdD. Use your knuckles to press in and knead for maximum oh là là.

Prostate milking: exactly what you think it is.

Once ready to bring the party inside, Stubbs says to use a well-lubed toy or finger to slowly penetrate the anus. Curved toys will give you a boost here, but if you’re going old-school, try to insert your finger(s) about two to four inches in, and flex them in a “come hither” motion toward your partner’s belly button (make sure to check in throughout to see how they’re doing!). If you feel two lobes (hence le walnut analogy), you’re there.

While some people can orgasm from prostate play alone, they’re more likely to get off when it’s combined with a hand job or oral, so don’t be afraid to multitask.

What to see when you arrive

If you’re feeling adventurous, you can try a little highly sensorial “prostate milking.” This stimulates the gland to produce fluid that combines with ejaculate to create a milky white liquid, explains Evan Goldstein, DO, founder and CEO of Bespoke Surgical. Use your finger pad to slowly massage the prostate from left to right, starting from shallow in the anus, then getting deeper. Don’t stress if it’s not instant orgasm. It can take a few tries (especially if this is unexplored territory).

If you have time, try…

Pegging! Use a strap-on and get behind your partner for all the zhuzh of prostate play plus a switched-up power dynamic.


How to be a respectful guest

  • Don’t show up uninvited. Make sure you get clear consent before diving in.
  • Do a pre-trip mani. Clip your nails, pls.
  • Take your time with foreplay. New experiences call for care and attention.
  • Don’t be a dick. Ideally, the receiver of anal play can try to poop beforehand to clear their bowels, but even still, you might come across some fecal matter. It happens! Treat your partner with the same comfort you’d like if it were *your* butthole.

Sex & Relationships Editor Carina Hsieh lives in NYC with her French Bulldog Bao Bao — follow her on Instagram and Twitter • Candace Bushnell once called her the Samantha Jones of Tinder • She enjoys hanging out in the candle aisle of TJ Maxx and getting lost in Amazon spirals. 

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