Many men (though not all) enjoy penetration during fellatio—that is, as long as you don’t stop or interrupt the blow job. Fingers are wonderful to penetrate with, and as opposed to sex toys, they afford you the most feeling and movement. You’ll already have your hands on him caressing and adding to your oral encounter, and when he’s turned on you can experiment with massaging his buttocks and caressing the crack between his cheeks. If he responds positively, try slowly sliding a finger over the opening to his anus while you’re giving him head. Be sure your hands are clean (read: scrubbed—no dirt or grime under your nails) and your fingernails are trimmed and filed smooth. Make sure you don’t have any tiny cuts or hangnails.
If you’ve talked to him about penetration beforehand, you’ve got it under control and are way ahead of the game. Discussing anal play before you try it is advised, unless you and your lover already have sexual adventure and exploration on the table. Anal play for someone who’s not ready for it can be very unsettling; don’t guess how he might react, because for some guys, anal penetration is going too far. So, how do you add anal penetration to oral sex and make it pleasurable? Follow the three golden rules: go very slowly, listen to the person you’re penetrating, and use lots of lube.
If you know he’s into penetration, and he is at the point when he’s not sure if he should be thrusting into your mouth or bucking onto your hand, check your accessories. You should have plenty of lube, and gloves or finger cots. The anus is an unlubricated area; it does not self-lubricate like a mouth or vagina, and the skin is thin enough to abrade easily. Use lube, lots of lube. You can never have too much lubricant. Use a thick, water-based lube. For smooth hands and to avoid getting bacteria from the anus on your hands, have a latex (or nonlatex nitrile or polyurethane) glove at the ready, or already on. Gloves also provide a firm, slippery sensation that feels absolutely delicious on the delicate anal tissues.
With the flat of your finger, or fingers, press lightly on the opening and hold it there. Increase the pressure a little, massaging and pressing in circular motions. Go very slowly, and listen to his cues or verbal instructions—for some, simply having their anus touched is all it takes to push them over the edge. Pay attention to lubrication, and never rely on saliva. In porn films they make it look like that’s all they use, but that’s not the case—they just don’t show you the anal suppositories and numerous applications of lube.
Move your flattened fingers in a circular motion, and begin experimenting with penetration by pressing one well-lubed finger at the base of the opening (toward his tailbone). Massage the opening’s base, and ask him if he wants you to go farther. Slowly slide your finger in up to the first joint (about an inch), and hold it there for a few breaths. You’ll feel the ring of muscles around his opening squeeze and contract—just stay still as the muscles relax.
When you feel the muscles relax, slide your finger in slowly a little bit more, then back out, doing a gentle in-and-out, not all the way in yet. Once again, this may be all it takes for him to come, or to decide that it’s not what he wants right now—but if he does want more, following his directions and body language from here, you can progress to more stimulation. You can go deeper or faster, or even add more fingers—but the rule of thumb is to do everything so slowly that you can practically feel the seasons changing around you. Anal penetration hurts when you go too fast, you don’t use enough lube, the recipient isn’t relaxed, or he doesn’t really want to be doing it.
Once he’s anally warmed up and ready for more penetration, you can bring anal sex toys into the picture. Sex toys used for anal penetration must have a flared base, meaning a base that prevents them from being pulled into the anal canal, where they can get lost—a nightmare waiting to happen. The sphincter muscles have minds of their own and like to squeeze and contract at will; we cannot control them. This serves to push and pull things in and out of the anus, and once something gets pulled in, there’s no guarantee you’re going to get it out without a trip to the hospital—which is what you’d have to do to prevent serous injury if, say, a hot, battery-powered vibrator went AWOL. Take a look at a standard butt plug and you’ll see exactly what a flared base should look like. Buy toys that are safe for anal use, and don’t get cute with carrots.
Vibrators can feel fantastic on the ass during fellatio, and you can tease and penetrate while you suck. The thing to know about vibrators and anal stimulation is that the outer third of the anus, and the prostate, contain more nerve endings than the anal canal and respond best to touch and vibration. The inner portion, inside the canal, has fewer nerve endings near the skin’s surface and responds to feelings of fullness, pressure, and rhythm.
So, a vibrator will feel intense (intensely good) around the opening and the prostate area. But the vibration won’t be a factor deep inside—the size, shape, and motion of the vibe will. To maximize your buzz, select insertable vibrators that have the vibration located at the base. When bringing a vibe into the action, start on the lowest speed, and give him more as he asks for it.
Squirt liberal amounts of lube on any toy you use, and reapply frequently. You can fuck the daylights out of him anally with a dildo he likes. Or, insert a butt plug and keep it in place while you suck and bring him to orgasm; just don’t leave it in for extended periods, or it will get downright uncomfortable. Chances are good that his PC muscles will squeeze the plug out before he orgasms; if you like, you can hold it in place with your free hand. It can also get forced out during orgasm, which is an okay way to remove it. But if it’s big and stays in place, after he comes ask him to take a few deep breaths and let him know you are going to remove the plug on an exhale—then remove it on the second or third exhale.
In men, anal stimulation and penetration can crank up the arousal for a variety of reasons, some psychological and some physical. One big, or little, reason is that rising star on the stage of sex play, the prostate gland. Much ado has been made about the prostate, and this tiny celebrity of the glandular glitterati doesn’t show any signs of slowing down as men and their partners discover the erotic potential of prostate stimulation.
In most every sex book you’ll pick up, if you can find a reference to the prostate gland at all (without it being exclusively related to cancer), you’ll notice a few strange things about the way authors tend to deal with the subject. Some impart a homophobic tone that makes even me wonder if I’m repressing anything—and this goes for both male and female authors. It’s as if they wanted you to be absolutely sure they’re straight when they’re telling you about what’s inside guy’s butts, and that you are too, and that everyone’s still straight after they read about it. The concept of male anal penetration obviously carries a lot of stigma and shame for these authors. This would be funny, if it weren’t so frustrating trying to get information out of their texts. The other unfortunate thing most books do when they cover real-life, try-this-at-home prostate stimulation (which is rare) is rush through the material and present it in a cold context, as if no one would really try this during sex. The gay guides are straightforward and enthusiastic, but there aren’t many of them available. And the straight manuals never suggest that the man try to find the prostate for himself—especially during masturbation, which is something I highly recommend. Oh, and did I mention that prostate play, or the enjoyment thereof, has nothing to do with sexual orientation? It doesn’t. End of discussion.