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Article by Maya Vukovska

We lose things all the time. Car keys, an umbrella, a glove, and sometimes even our minds (especially on a Black Friday and during Christmas holidays). So, what’s the big deal with losing your virginity, you’d ask. You can’t use it as an additional asset to your LinkedIn profile, so why need it anyway! Well, the thing is that once you’ve lost your anal virginity, it’s highly improbable to have it back.  If you are in a phase of your flourishing active gay life when you are considering handing out your V-card, it’s wise to inform yourself in advance what to expect.

Gay men do not always agree when it comes to defining gay virginity. To many, you stop being virgin the first time you have oral. However, there’s an unspoken rule that goes, “If someone puts his dick in your ass, it’s penetration, and once you’ve been penetrated, your precious V is gone.” End of discussion. There’s sex, and then there’s anal sex, and the latter is generally considered to be the very definition of gay intercourse. If you are still technically virgin intact, but you think you have found the right penis to do the job, here is what you should know.

Don’t succumb to peer pressure

Peer pressure is always tough to deal with, especially when it comes to sex. And when it comes to gay sex, the situation can get really tense. If your gay social circle is trying to convince you that you are not really gay until you get bum-drilled, ignore these voices hard. All in all, what they are saying is that you’re gonna get fucked before you fuck someone, and it’s pretty much inevitable. OK, that must be true, but still, it’s important that you do it when you know in your heart that you truly want it. Being emotionally ready is of top priority. Because no matter what they say, or what you have experienced so far, sex IS emotional.

Prep yourself

It’s not as easy as it looks in porn! If you have concerns about your first time (which is completely normal!), maybe you should start with baby steps. In this case, anal beads. Of course, first you make sure they are the right size for beginners. Some experts in the area recommend using a vibrator to learn how to relax the anus. You should get used to the idea of something getting through your backdoor. Beside beads and vibrator, you may also consider using rimming plugs and regular dildos. These toys will not only open the anus, but will also arouse you in a way you’ve never experienced before. And yes, that will prep you for the real dick penetration.

And PrEP yourself

All sexually active and responsible people know that any sex puts them at risk for sexually transmitted infections. The magic PrEP pill will prevent HIV infection. Condoms, on the other hand, are cheap and available, and can easily become your Batman fending you off not only AIDS, but also other badass diseases, such as chlamydia, syphilis, and gonorrhea.

Yes, it might hurt

You know what they say - no pain, no gain! So, you must be prepared to face reality. If you have never tried it before, then you should know that your ass will be tighter as the buttocks of a straight man going to jail. Your ass expands to harbor a penis, and the stretching will hurt. I have to be Doctor House honest here and warn you that if you don’t use lube, a lot of lube, you can suffer a lot more than you expected. The keyword here is “communication”. Talk to your partner, and negotiate breaks whenever you need them.

Shit happens (literally)

There’s nothing you should be ashamed of. It’s what your body does, and it’s beyond your control, like it or not. I understand that you want to avoid the embarrassment, so clean your butt before the intercourse using a drugstore enema. It’s super cheap, but you need to carefully read the instructions on the box in advance. Usually, enemas contain laxatives. But since you don’t need to relieve constipation, make sure you empty out the laxative and substitute it with plain water before use. The simple rectal bulb syringes can spare you the mess to some extent, but sometimes sex may happen out of the blue, with no enemas around, and then you will have to face the reality. When you are having anal, you are going to deal with poop at some point.

Assume the right position

I won’t recommend doggy-style no matter how appropriate it may sound. This position puts your partner in full control, and this is not what your beginner ass might like. On the other hand, spooning is a great pick: it gives an extra touch of intimacy, and will also help you relax. During the action, have him jerk your cock to increase your pleasure level.

Being a bottom doesn’t make you “the girl”

It only defines what you’re doing during sex, and nothing else. And whoever dares call you “Mary” can go play with their own balls.

First time might suck

Whatever happens this first time you shouldn’t allow it to affect your confidence. You may not orgasm during anal, since it’s not unusual to lose erection for a while, especially if you are uncomfortable. Take it easy, and let a different set of stimuli kick in. Remember that it will get better with time. Just give your ass some time to relax and reflect on what’s happened to it.

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