If you haven't read Part I of the Anal Play for the Straight Guy series, click here.

An Arlington Boy Guest Post:

Okay, so now your new plaything has come in the mail. And much to your relief, the packaging didn't read: CONTENTS: ONE ASS BLASTER 6000. WARNING! RECIPIENT IS MOST LIKELY SOME KINDA PERVERT AND BELIEVES IN SOCIALIZED MEDICINE.

Your normal masturbation sessions may involve your hand playing the role of the village bicycle. Get up, get off, get out. But tonight you're not going to be with the village bicycle. You're going to treat your ass like someone who plays hard to get: be convincing; take it slow; and be gentle. You get the idea. Your hand is the town slut. Your ass is that rich, stuck up chick whom you finally convinced to give you the time of day.

First, make sure you're alone. Unless you're an exhibitionist, in which case knock yourself out. But do lock the door, shut the blinds, and turn off your phone.

Try pouring yourself a drink to relax a bit. Grab a towel and get comfortable, either on the floor or on your bed. Find a really hot porno, and either pop it into your DVD player or fire it up on your laptop. Since you're doing something you've never done before and are most likely going to be nervous, make sure it's one that has at least one scene that gets you off.

Next, take some time and do whatever it is that makes you feel good. Don't rush. You want to spend some time really getting yourself turned on. When you're starting to feel really hot and bothered, work your hands down to your perineum (the soft, fleshy area between your anus and your balls) and start massaging it and warming it up.

When you're feeling nice and relaxed (and turned on!), take a small dab of lube and apply it to one of your fingers. Then, start circling your anus slowly and gently. Just give it a soft massage in a circular motion. You want to make sure that part of your body is nice and relaxed. When you're feeling confident, slowly insert your finger in juuuuuuust a bit, and rotate it around and massage the entrance to your anus. Give it a good little massage, but again, take your time! And enjoy yourself!

Okay, so now's where the rubber meets the road! Take your plug, and coat it with a generous amount of lube, spreading it out all along the length of the plug (leave the base dry). Wipe off any remaining lube from your fingers, and take a nice, slow deep breath in and out.

Insert it gently and slowly. While "MORE FORCE" might be great for DIY projects such as that screen door that just won't close right, this isn't something you want to rush or use any amount of force on. You might try wiggling it around in a circular motion (gently) while you're (again, gently) pushing on it. Take it slow, and take lots of deep breaths. There's no hurry!

Fact: you actually have two sphincters in your anus. I'm willing to bet the plug started to go in nice and easy. That's your outer sphincter. Hey, this doesn't feel bad! And then you worked it up a bit more and OMG I GOTTA GO TO THE BATHROOM!!! Congratulations, you just found your inner sphincter. Think of your outer sphincter as the TSA: it'll let anyone come in. Think of your inner sphincter as an elite bodyguard (bootyguard?): none shall pass!

Don't worry… just keep your plug inside you as far as it'll go comfortably. It's perfectly normal for you to feel like you need to move your bowels the further up your plug goes. Keep on watching your movie, pleasuring yourself, and have another sip of your drink. Relax. Your ass will start to get used to the plug, and eventually (particularly as you start to get more turned on—whether from the movie, the plug, or your own self-pleasuring) it should go in the rest of the way. And if it doesn't? No worries. Try it again later.

You've probably read the words "relax," "slowly," and "gently" enough to piss you off by now. Good, because that means I'm driving the point home. Anal play (especially your first time) needs to be taken at a relaxed pace. Rome wasn't built in a day, so don't worry if it takes you a while (even over the course of several sessions) to feel comfortable enough to put your toy all the way in.

Now what? Well, a plug isn't designed for in-and-out action. It's designed to stay in and give you a sense of fullness. So take a few deep breaths, enjoy the feeling of your plug inside you, and gradually bring yourself to climax.

As you start to get to the point of no return, you're going to find something really interesting going on. Your plug is *really* going to start feeling good inside! In fact, your anal muscles are probably going to start milking the plug. This is why your toy has a flared base. To prevent all that slipping and sliding and milking from making your toy rocket up inside you! You might notice the reverse: as you start to ejaculate, your plug actually shoots out of your ass!

Congratulations! You've just taken the first steps to a whole new world of pleasure! Don't be in a hurry to clean yourself up. You did something that a *lot* of people aren't comfortable with. You may have a whole host of feelings going through your mind and your body right now. Relax and enjoy yourself for a bit.

As you continue with your experimentation over the coming days and weeks, you may find you want to get a new toy that's a bit bigger. From personal experience, as good as my Little Flirt toy feels, you'll get only so much mileage out of it before you want to use something larger. Again, take your time, get a plug (or another toy) that's a little bit bigger, and start the whole process over again.

I hope my post has helped demystify anal play and has shown you that there's a whole new world of pleasure that's just waiting for you to explore. If nothing else, I hope you keep this in mind:

If you tried it and enjoyed it, there's nothing wrong with you, and you're perfectly normal!

If you tried it and didn't enjoy it, there's nothing wrong with you, and you're perfectly normal!