March 11, 2008 | Sex Life

Up my bum, you say?

Let's face it: anal sex is an acquired taste. And just because you're gay doesn't mean you like taking it up the bum. It can hurt and it will certainly feel a little weird the first time. That said, it can open you up to sensations that are as wonderful as they are intense. 

If nothing has ever slipped passed your sphincter, shoving a dick up there is not the best first step. After you've gone to the bathroom (you know what we mean) run a warm bath to help you relax. While laying back in the water you can start exploring your bum with your fingers. No need to push inside yet; you'll want to use some lube for that! Just enjoy the feeling of the outside of your rosebud being played with.

Once you hop out of the bath and dry yourself off, head to your bed with a towel. Covering your anus and finger with a liberal amount of lube, explore your ass a little more aggressively by slipping your finger inside. You can move your finger in circles, pump it in and out, and even dig around inside of your hole to see how different amounts of pressure, and different positions, result in unique sensations.

And it gets better...

Feeling daring? Try slipping in a second finger! Don't work too fast; take your time and ease it in.

After you've done this a few times, you are ready for something a little more substantial. Always opt for a dildo over some other household item; fucking yourself with a zucchini, wine bottle or traffic cone may seem like a great idea in the heat of the moment, but you risk tearing the lining of your anus (ouch!) or having something get lost inside your bum (try explaining that to your doctor).

Before using the dildo, you'll prepare yourself with some more fingering. As you start to feel relaxed and ready, add more - as in lots of - lube to your ass and the dildo. Find a position that works best for you: maybe hold your knees up with a pillow under your lower back, or lay on your side with legs pulled towards your chest, or even doggy style - and slowly push the dildo in.

You may want to start with something a little smaller.

Relax. Relax. Relax. Take it slow. If it starts to hurt, slow down even more. Let your ass get accustomed to the new sensation. It may feel like you're squatting on a boulder at first; this feeling with change in a a minute or two. If it doesn't, then you'll need to find a smaller toy or try again another time.

Eventually you should be able to work the whole thing in. Voila! You are half way there.

Now, you need to pull it out. Once again go slowly. It's going to feel like you have to go to the bathroom again. This is normal. And yes, you may even have an accident. (They don't tell you that in sex ed, do they?) Your body is naturally designed to  push things out down there and if it does happen, welcome to the club. It's not the end of the world, so don't feel bad about it. Too often this feeling keeps many bottoms from really enjoying the experience.

You okay? Good. Start working the dildo like it's another man's cock. Push it in and out at different speeds, or differing angles. Try changing your position to see what feels best. Maybe even try squatting on it as if you were riding that hunky bartender while he lays beneath you. You'll soon find what works for you.

Pierre Fitch won't leave home with it.

There is a second feeling you may come across. With the dildo, or a real cock, inside you, you might think you need to pee. Again, this is normal. Urinating is very unlikely. Try masturbating a little and learn to use the feeling to help you orgasm like you've never been able to before.

When you're ready to get off this crazy ride, take your time withdrawing the dildo. With all that action up the bum you may make a bit of a mess. Dirty lube, or more, may come out. No need to worry; again this is normal and the experience of about 99% of the men who have bottomed before you. That's why God invented towels and soap. (Well, He may have created them for other things, as well.)

You'll also find that your ass stays open for a while. Your sphincter has been stretched and will tighten again, don't worry. This is why it is so important that you never force anything inside so as not to damage it; with enough lube and patience, you'll not have anything to worry about.

After a few more solo flights, you'll be ready to play with the big boys!