Good Vibrations Magazine

In the last two “Male Pleasure” columns (available in the archives above), I talked about how you could bring up the subject of male anal love and get started playing with your boy’s butt.

If everything’s gone swimmingly, you might want to expand your technique, adopt new tools and help your man enjoy new forms of anal pleasure. This third — um, entry — will cover anal penetration of men with dildos, anal beads, butt-plugs, and vibrators. I’ll also say a word or two about oral-anal pleasure.

The most important thing to remember is, as I’ve said before, anal sex is not a goal-oriented activity. All anal play does not have to proceed to penetration. The exterior of the anus is very sensitive, and you can have hours of fun just playing with it.

But if he’s enjoying himself and you’re enjoying yourself and you both — um, dig — the idea of deeper exploration — then on with the show.

Rimming

First, a word about rimming. Some of you may be wrinkling your noses, but almost anyone who enjoys anal sensation and has had the pleasure of being rimmed will tell you that it feels incredible. For the giver, it can be a lot of fun, as well. In one sense, it’s vaguely similar to cunnilingus — but you can do it on a boy as well as a girl!

Unfortunately, rimming isn’t the safest activity in the world. Though it’s relatively low-risk for transmission of HIV, it’s a high-risk activity for transmission hepatitis A, B and possibly C (which are collectively much more common than HIV — and much, much easier to transmit), as well as intestinal parasites and a whole host of other sexually transmitted diseases.

That’s why the kitchenware manufacturers of the world thoughtfully invented plastic wrap. Well, maybe it’s not why, but that certainly is a nice image, isn’t it? Place a dab of lube on his anus, spread some plastic wrap between his cheeks, and have as much fun as either of you can stand. Another option are Dental Dams and the thinner (and therefore more sensation-transmitting) Glyde Dams. Plastic wrap, however, has the advantage of being dirt cheap and not tasting like anything. You can also spread oil-based goodies like whipped cream on the wrap (your side of the wrap, silly, not his) to provide you with hours of tasty delight as you explore his sensitive side. Dental dams aren’t safe for use with foods that contain oil.

If you do rim without protection, ask him to wash well with soap and water — and rinse well (unless you actually like washing your mouth out with soap). Afterwards, rinse your mouth with antiseptic mouthwash. You can still catch many very nasty things, but these two measures will lessen your risk substantially.

Lubricant

I keep saying this, but it’s really, really important. You don’t want to end up in the middle of a hot and heated session and run out of lube. Not everybody prefers thicker lubes for anal play, but they’re a good idea when you’re just starting out, because they provide a little more cushion. Thick lubes like For Play Lube deluxe Cream, Embrace, or Slippery Stuff Gel are excellent for anal play.

The silicone-based Eros Lube can be a nice change of pace, but remember not to use it with cyberskin or silicone toys — it’ll ruin them. Similarly, don’t ever use an oil-based lube like Men’s Cream, petroleum jelly or baby oil with latex toys, since they will slowly dissolve the toys (as well as any condoms, gloves or dental dams they touch). In any event, petroleum jelly tends to dry out anal tissues, and baby oil is too thin to be ideal for anal play. Neither are recommended.

The Prostate

Many guides to male sexuality ignore the prostate, which is a mistake. It’s a walnut-sized gland several inches inside the rectum — the depth varies from man to man, but you can sometimes reach it with your fingers; other times a dildo is required. Women don’t have a prostate — but, in fact, it’s theorized that the prostate is the male equivalent of our G-spot, so it won’t surprise you to hear that many men experience mind-blowing sensation and even orgasm from prostate stimulation.

If you find his prostate for the first time, I would advise you to be gentle — poking it indiscriminately can hurt. But gentle stroking can drive him out of his mind. Remember that not all men enjoy prostate stimulation — anal play can feel great without it. But many men really, really love it.

Anal Plugs

As I mentioned in the last column, fingers are not exactly the smoothest part of the human body. Therefore, even if fingers didn’t feel good inside his butt, a narrow anal toy like the small Majestic Plug, the Slim Jane, the Little Flirt, or the petite Shapely Plug can feel great, since, conveniently enough, they come without fingernails, calluses, or knuckles. The Little Flirt has the advantage of being silicone, so you can boil it to disinfect it before and after use. If you prefer to use a condom to keep your plug clean, you can pull the end of the condom over the base of the plug and tie it, or cut one of the fingers off a Latex Glove and stretch it over just the insertable part of the plug.

Another point about butt plugs is that they’re a little misnamed. They can be left in the anus if you like while you go about other delicious business, but in my experience they don’t always stay put without a hand, surface or harness to hold them in. This is especially true of smaller plugs, making them better adapted to play with the same way you would play with a dildo. The silicone (and festive-hued) Tristan Plug definitely stays put — but it’s a little wider than some beginners will want to try.

Whatever you insert into his butt, be absolutely sure that it has some kind of flange or base wider than the inserted part. Unlike the vagina, the anus is deep, and it’s easy for non-flanged toy to slip in there. It sounds silly, but you’d be surprised how easy it is to lose hold of something when your hands have half a bottle of lube on them.

Vibrators

Vibrators can be especially fun for beginning anal explorers. The vibrations tend to relax the anus, making penetration easier — and just generally feeling damn good. Not everyone likes them, but given the availability of inexpensive vibrators, they’re definitely worth a try. Again, make sure that you use a vibrator with a flange or attachment at the base so it doesn’t slip all the way inside his butt. If a vibrator slips in there when it’s turned on and you can’t get it out — that really means a trip to the emergency room, and fast. The heat generated by the vibrator’s motor can cause serious problems.

The Scorpio is Good Vibrations’ most popular vibrating toy for anal beginners. It’s relatively inexpensive, thin and easy to insert. Other great vibrating anal toys are the Arrow Twist Vibe and Ruby Vibro Plug. The Red Rider Plug has the added advantage of having two thicknesses you can play with, so it’s splendid for beginners.

Remember never to put a vibrator like the Smoothie in his butt because — you guessed it — it doesn’t have a flange. Smoothies can feel great on the outside of the anus, however.

Anal Beads

Other good anal toys to try are Bubble Beads and Anal Beads. Both of them are relatively small in diameter, but their geography will usually require you to insert them with fingers inside the anus, so they’re probably not the best toy for absolute beginners. The usual concept behind anal beads is that you insert all or most of them, then pull them out either one at a time or all at once, quickly, just as he reaches orgasm. There’s nothing that says you have to use them that way, but I’ve had rave reviews of that technique from more than a few male friends. If you’re going to try that, though, use lots of lube, since whipping out an insufficiently-lubricated set of grape-sized friendlies will put a major buzzkill on that orgasm he’s having.

Dildos

As with all anal play, it’s a good idea to start small. That’s not to say men don’t like big things in their butts — in fact, a lot of them like very big things in their butts. But with a recipient who’s new to anal penetration, it’s best to be conservative. “That feels so good, I want more!” is so much sexier than “Owwwwwwwwwwch!” or “Get away from me with that monster!”

Again, be sure that any dildo you put in there has a base substantially wider than its shaft. It is not fun to go fishing around for something that’s slipped out of your hand, and if something really gets stuck up there, it means a trip to the emergency room.

Silicone dildos like the Rex and Hot Rod tend to be a little more rigid than non-silicone toys, making anal penetration a little easier in some peoples’ opinion. Non-silicone dildos like the Pearl Jelly Dildo, the Jelly Jewel Amethyst or the Duke, on the other hand, tend to be cheaper, meaning you can try different sizes and shapes without cashing in your stock options. Latex toys can’t be boiled, but you can keep them clean with condoms, or by just scrubbing them down with antibacterial soap after use. They also tend to collect lint, so you might want to rinse them before use.

Many dildos look like penises. If your man is squeamish for any reason about enjoying a dildo that looks like human equipment, some excellent “non-representational” dildos are the Babe, Queenie, Silk and Willow.

Again, go slow — in-and-out isn’t necessarily the end-all-be-all, any more than it is with you. He may like in-out-repeat a lot, or he may just prefer the feeling of fullness that comes from having a dildo inside him. Either way, he may enjoy it if you stroke or kiss his penis and the rest of his body, keep eye contact with him, and/or tell him exactly how sexy he looks with his legs spread and a dildo in his ass.

If he loves this more than either of you ever dreamed he would and finds himself hungry for more, more, more — remember, there’s always Randy. He’s very friendly, but I wouldn’t suggest bringing him along on a first date.

Next installment will deal with strap-on dildos, double dildos, and what to do if you’re lucky enough to have one of those lucky anal invaders with a flesh-and-blood penis, also known as a man.