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And then there is an issue of the massage table versus the bed. If you already have a massage table, try it. She might enjoy being able to stand up while she’s playing. Or she can perch between his legs on the massage table. If you don’t have one, I’m not sure it’s worth buying one for just this purpose. A big bed, or even a towel on the carpet, really does work well because it gives you both more room to spread out.

Here’s a technique for going deep inside him, to reach the top of his prostate. Position him on his back with you sitting on his right (assuming you’re right-handed) alongside his belly. Then you bend forward and slide your right index finger inside him from between his thighs. You may end up bending forward so far that your shoulder is all the way down against the bed◦— in other words, with you lying on or kneeling over his right leg.

Another position is recommended while using the Aneros prostate massager which we will talk about in the next chapter. This position is on his side with both legs bent, the top leg bent more than the bottom. This, by the way, can also be a good for prostate massage without the Aneros.

Sex Toys

Toys offer an easy way to add spice and pleasure to your sex life, both for men and women. The toys that concern us here are those meant for anal insertion and massage. All can be used with a partner or solo.

The insertion of toys may not be entirely pleasurable for some men right at the start, just as prostate massage may not feel good at first. Therefore, beginning anal play needs to be gentle and should be combined with genital pleasure to build the positive association for men.

You must be careful about one thing: do not insert any toy into the anus that lacks a flared base or other guard. Toys have a way of disappearing inside, possibly necessitating an embarrassing emergency room visit. Believe it or not, that happens all the time. If it happens to you, make things easy for everyone and just tell them the truth in the emergency room. They have seen it all, lots of times!

The primary types of sex toys for anal play are prostate massagers, butt plugs, dildos, and vibrating toys.

The Aneros prostate massagers and similar devices are getting rave reviews from many men. Their use is entirely hands-free, because they have little wings that stay outside and perch on the perineum. During prolonged play, you may need a washcloth to pad the wings if the pressure on the perineum is a bit too much.

The Aneros looks a little like a narrow asymmetric egg. At one end is a neck, with little wings that stick out sideways at the tip. To use it, apply lube and insert the egg-shaped part slowly and carefully. Once inside, the device stays in place very nicely, all by itself. To generate more intense pressure from the Aneros, contract your anal sphincter (the muscle you also use to stop the flow of urine). You can contract a little or a lot, and you can do the contractions slowly or fast.

The Aneros works well slipped inside while the man receives a genital massage◦— that is certainly a special treat. Also, some men enjoy having sexual intercourse with it in place. Then it works fine either with the man on the bottom or on top.

Regular butt plugs look like little cones with narrow necks and flared bases, designed so they will neither fall out nor get lost inside. They come in a bewildering variety of sizes, and it may be best to start really small and work up. Butt plugs are usually inserted and then left in the anus, rather than providing an in-and-out motion. Be careful to insert the toy slowly and gently (and remove it that way, too) for a maximum of pleasurable sensation. Butt plugs can pop out if the wearer moves a lot or bears down.

Dildos usually look like penises, more or less. However, some are designed to seem ‘lifelike’, and some are works of art, resembling animals, people, etc. They also vary a lot in size. For anal use, be sure to get one with a flared base so it cannot be sucked in. Dildos tend to pop out even more than butt plugs if not held in by a hand or clothing. Use them with a very gentle and very slow in-and-out motion and with lots of lube.

Dildos work well for anal play for both men and women since it’s possible to start small and gradually increase the size of the dildo you are using. Better too small than too big for pleasurable first experiences. It’s nice to have an array of sizes and shapes on hand so that the receiver can choose the one he’s in the mood for.

A dildo can be used with a strap-on harness by women or men. The harness used can be traditional position, with the dildo located where a penis would be. This provides more of the look and feel of sexual intercourse. Alternatively, the harness can be wrapped around the thigh. This method is less tiring to the wearer of the harness, and actually provides for more precision of movement.

When planning to use a butt plug or dildo for anal play, it is best to cover it with a condom. Use a non-lubricated condom because it is less sticky, and put it on ahead of time so that you do not need to interrupt your play.

Condom use is especially important if you are using safer sex practices with your partner. But even if you do not need to use barriers for safety’s sake, condoms make cleanup much easier. They also prevent discoloration and clinging odors.

The tricky part about shopping for sex toys is that there are zillions of them, ranging greatly in price, material and quality. So research and shop carefully. It is possible to spend a lot of money and end up with a closet full of sex toys that mostly go unused. Educate yourself before you buy.

Many toys are silicone or rubber-based (it should say on the packaging) and thus cannot be used with any greasy lube or oil, which damage the material. If you use a silicone sex toy, use only water-based lube. Or you can cover the toy with a condom and then use any lube.

Small butt plugs can be inserted entirely into a condom, flared base and all. For larger dildos, the condom is rolled onto the shaft, just as on a real penis.

There are also some sex toys that are meant to be hand-held, either by the man or by his partner. They clean up well in hot soapy water, so you may not wish to use a condom with them.

These toys are S-shaped or shaped like a honey-dipper. You hold them in your hand, slide them in, and vary the angle by applying pressure on the handle. It can be quite a bit of work to use these, but many people love them. If the active partner gets tired, you may prefer to switch to a toy that stays inside by itself.

You can also find some anal and prostate toys that vibrate. Again, make sure that they have flared bases so they can’t vibrate their way too far inside the rectum. The jury is out on these toys: often, the vibration is too weak to make a difference, or is not in a good location to feel really great. There is huge variation of opinion on the benefit of these toys, due to anatomical differences as well as preferences in individual sensation. So you really just need to do some experimenting.

However, there is one vibrating sensation that most men like: the good old Hitachi vibrator that is so beloved by women. Hold in on his perineum, using a little hand towel between the vibrator and the skin to dampen the intensity at first. It can also be used directly on his penis.

Remember to use a lot of lube with any insertion toys. Sometimes it can be difficult to get the lube where it is really needed, which is on the inside the anal opening. One method is to coat the toy (or the condom that is covering the toy) with silicone lube first, and then use water-based lube after that.

Another way is to insert some lube before beginning with the toy. There is a device called a ‘lube shooter’ that is sold in sex shops; the Aneros company has a similar device called the Marksman. This is a blunt syringe, whose tip you carefully insert into the anal opening, and then push the plunger to slide a measured quantity of lube inside. Make the use of a lube inserter be part of playing, rather than just a preparation for play. And be sure to coat the butt plug or dildo with lube as well, even though there is already lube inside.