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Editors Note: This column is part two of a four part series about rounding the proverbial bases.

If getting to first base can land you in MIT Medical – then going further can sometimes only get worse. Second base is typically defined by fondling and groping — what this really means is frantically ripping off each other’s clothes and exploring each other’s human anatomy first hand (quite literally). It’s a prelude to fucking, and unless you’re roommate is coming back soon, you’re probably going to take off your clothes. So, transitioning from the vanilla making out to throwing clothes into the abyss of a messy room can sometimes get awkward.

The awkwardness starts at the beginning — unclasping the bra. Even experienced guys sometimes struggle with this. It’s incredibly embarrassing when someone turns on a light just to figure out the clasps. Usually, a simple inward push should work — especially if the girl is less busty. If she’s bustier, there are more hooks — so, work each hook one at time if it seems too complicated to do it in one swoop. If she’s wearing a sports bra, that should be easy — just slip it over her head. Come on, guys, its simple classical mechanics. Girls, if it’s taking too long, just help the guy out, unhook the bra yourself; I mean, come on, you do it every night.

After the bra comes off, here’s where a lot of guys mess up. There’s a difference between fondling and squeezing. Applying too much pressure doesn’t feel good — I’d even liken it to getting your “family jewels” squeezed. So, follow the golden rule here, don’t grab or squeeze. Also, girls, guys don’t care much for anything done to their chest.

Now we’re getting to the bottom of this — the “private” parts. First of all, for both genders, keep your nails well-groomed: no one wants to get scratched. Well-moisturized hands are also a luxury. Make sure the girl is well-lubed — otherwise, it just hurts. Start off slowly, don’t just jab a fist in there — that’s just proof porn lies. Also, that can be dangerous. Gynecological emergencies are unnecessarily embarrassing— getting injured while hooking up, while possibly funny, is not fun to explain to your parents if they’re footing the medical bill. Guys run the risk of less injury here — I’ve never heard of a handjob hospitalization. All guys masturbate — most give themselves a handjob on a regular basis. Because they masturbate, they know what they like. I encourage good communication here — each person’s anatomy is slightly different, and if something feels good, why not tell them? The angle is important for both guys and girls, and you should let your partner know when theta is just right. (I’m worried that line is way too nerdy and proof of MIT’s effect on me.)

The prelude to sex doesn’t need to be awkward — it can actually be the best part. So, note where you threw your clothes, and just enjoy yourself.