Despite the progress we have made, many people still love labels, especially when it comes to sexual preferences; with ‘tops, bottoms and sides’ – it sounds like a NSFW gameshow hosted by Michael Barrymore.

But there’s no reason why you should be restricted to just one – versatility is the spice of life, after all. Or the bedroom, at least.

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Dr. Evan Goldstein, of Bespoke Surgical, (an expert practice in the sexual health of gay men, and all-round well-being of their bottoms) explains how you can move from active to passivo without injury – but with all the pleasure.


“I believe there are 4 key things that help make your first time more pleasurable and less prone to injury: relaxation, communication, (plenty of) lube, and proper positioning.”

So yeah, notice he didn’t say anything about poppers. (Which have also been known to caused the anal capillaries to pop and bleed, increasing risk of infection).

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If it’s your first time bottoming, something you’ve only done once in a blue moon after too many vodka sodas, and/or your partner is particularly big/girthy, Goldstein recommends dilating.

“This will help your muscles relax and also help lubricate the entire anal canal.  There’s really no such thing as too much lube, especially when you’re just starting to bottom.”

Hear this hennies, lube is your FRIEND. This isn’t Brokeback Mountain y’all, leave the spit and pick-up the real deal.


“The best position to start with is the bottom on top, which allows the bottom to have total control of the depth and speed of penetration that feels right.” Goldstein suggests.

“Only after the bottom feels themselves relaxed and open, and there’s no longer any discomfort, then it’s probably safe to switch things up—change positions, increase the depth, and adjust the speed.”

Remember it’s not a marathon, there’s no rush, or harm in taking things slow.

[RELATED: Getting to the Bottom of Our Sexual Preferences]

“Since everyone’s body is different (on the inside – as well as out), you’ll have to experiment to find which positions are most comfortable,” Evan continues.

“Things like length, girth, and curvature of the top’s penis, as well as the overall position of the bottom’s pelvis is key here”.

Penises come in all shapes/sizes, but so anuses; and they slot together much like a lock and key, some fit more comfortably than others. So when you find your ‘key’, lock him down.


“Good communication is equally important to let your top know what works and what doesn’t. Don’t be afraid to speak up. If you’re not having fun, your top probably isn’t either.”

Unless he’s Topher DiMaggio.

“It’s OK to be especially picky during your first rodeo because you want a top who will be patient and make you feel totally at ease. The more tense you are, the more likely you will be to clinch up, which you definitely want to avoid.”