Losing your anal virginity: Young man prepares for a romantic date: puts condoms in the pocket of classic pants. body part: men's tight ass. Remember to protect. safe sex, AIDS. office worker holding condoms in hand

Bottoming is a milestone in the lives of many gay men, but before you dive into the fun, there’s the matter of losing your anal virginity. Indeed, bottoming often marks a rite of passage. (Unless, of course, you’re analphobic or one of those boring “total top” types. In which case, you’re seriously missing out.)

Still, losing your anal V-card can be a scary thing. But it doesn’t have to be!

Some people, especially fundy Christians, see virginity as some kind of trump card to hold over potential suiters. A sacred act that must take place only after marriage. We don’t see it that way.

For gay men, it represents just one of the many remarkable ‘firsts’ in life— like your first great French meal, your first drink, the first time you hear a Madonna song, or even watching your first football game.

In that spirit, here are five tips to help make losing your anal virginity a pleasant experience:

1. Finding your fellow

A gay couple in tank tops

We like to think of losing our virginity as this magical thing between two people who are deeply in love, but the reality is, very few of us actually keep in close contact with the guys who popped our cherries. Chances are five years from now the closest relationship you’ll have with the man who holds your V-card is a Facebook friendship, if that. And that’s okay.

That being said, you probably don’t want to lose your virginity to any old Joe Schmo off the street, although that actually sounds fun now that we mention it. Seriously, don’t agonize over finding someone special and being in love and all that like an evangelical might.

Avoid other fumbling virgins. Just locate a decent-looking, trustworthy guy whose danced the chocolate cha cha once or 500 times before so he can show you the steps. And this is probably the last time you will ever not be a size queen.

2. Location, location, location

The place where you first have your peanut butter stirred is also important. For the rest of your life, the topic of how you gave up your V-card will undoubtedly arise at parties and other social gatherings, and you want to have a good story to tell.

“I lost it in the penthouse suite of a 5-star hotel,” is sure to impress people.

“I lost it in the back seat of mom’s minivan.” Not so much, although that would work, too.

3. Cleanliness is next to godliness


We’re about to get down to the nitty gritty, so brace yourself, virgins.

An unclean butt has a way of instantaneously killing the mood. So wash, wash, wash. And then wash again. If you are doing it publicly as performance art, you might want to repeat the procedure one extra time.

Losing your anal virginity is stressful enough. (Side note: We like to think of it as gaining a sex life, not losing anything worthwhile.) You don’t also want to be concerned about having an accident on your maiden voyage down the Hershey Highway. One way to reduce this fear is by conducting an enema 30 minutes to an hour before engaging in anal sex.

How does it work? Easy. You insert the tip of the enema , squeeze the water, hold it in for a minute or two, and then release. Full disclosure: Doing an enema isn’t pleasant, but it takes less than five minutes and it makes for a nice clean dip in the pond. If you are feeling less than solid due to the nerves, you may want to pop an Imodium or three.

4. Condoms, lube, and more lube

Condoms are good. Use them with an ample supply of latex-safe, water-based lube. The bottom line (pun intended) is this: The first time a man plows your backfield might involve a little pain. It will be much less painful, however, if you slather yourself up beforehand. You may also find loosening your sphincter with a finger or three helpful, or using a toy, like a dildo or small plug. Of course, the best way to relax is with a good old fashioned rim job, which your top will likely provide with gusto. (After all, it’s the polite thing to do.)

If you are one of those guys who is hell bent never to use a condom, make sure to talk to your doctor about PreP first.

5. Relax and enjoy

After a minute, discomfort subsides. Granted, it can feel like the longest 60 seconds of your life, but once you get through it, it’s done, your muscles have relaxed, and all you can think about is the deeply pleasurable sensation happening in your loins.

So take a deep breath, throw those legs in the air, relax, enjoy, and welcome to the club!

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