Mastering Multiple Position Sex (26 page)

POSITION 1

POSITION 3

CRESCENDO

This Chapter’s Positions and Their Degrees of Difficulty:

XXX
XX
  
POSITION 1
: The Fireman’s Pole

XX
XXX
  
POSITION 2
: Transition

XXX
XX
  
POSITION 3
: The Ramp

In spite of the potential it offers for pleasure and excitement, whether for reasons or rumors of religion, hygiene, or supposed pain, anal intercourse remains a difficult subject to broach in a relationship. So before you initiate a healthy conversation about introducing anal sex into your bedroom so you can learn to enjoy a “backyard get-together,” let’s dispel a few misconceptions and discuss how to talk about anal sex.

Anal sex is dirty
. Though a potential for germs does exist—inevitable, considering the anatomy involved—there should be “no traffic in the tunnel.” That part of the rectum is not home to any fecal waste, but an anal douche or enema can help alleviate a couple’s concerns. It’s also important to use a condom as often as possible, and, despite what you may have seen in erotic films and magazines, not to shift from anal sex to other forms of penetrative intercourse to avoid cross-contamination.

Anal sex hurts
. By following five simple steps to help you relax, you can have anal sex that is as pain free and as pleasurable—if not more so—than other forms of sex. Anal sex is one of those parts of life that follows the axiom be careful what you wish for, because you might get it. People who predict that it will hurt are likely to feel pain, and those who slide under the covers expecting fun and excitement will probably be back for seconds.

Anal sex can cause serious permanent damage to your rectum
. When done safely and as one item on your sexual menu, anal intercourse will not damage the rectum permanently.

If a heterosexual man plays with his own ass or asks his girlfriend to, that means he is gay OR anal activity can make him gay
. Using a finger, tongue, or toy for anal play can no more make a heterosexual man gay than eating bananas would turn him into a monkey. Besides, not all gay men participate in anal sex and not all monkeys eat bananas. To every man reading this book, I give you permission to explore every part of your body; perhaps if you were to “press the P-spot”—your prostate—or even get close to it, you might have pleasure like you’ve never had before. Believe millions of happy hets: Anal play doesn’t make you less heterosexual—just more sexual.

Setting the Stage

When thinking musically about anal sex, your soundtrack should be Louis Armstrong’s
We Have All the Time in the World
rather than Rimsky-Korsakov’s
Flight of the Bumblebee
. Relax, because good things come in those who wait. The five notes of anal intercourse are:
communication
,
trust
(both in yourself and in your partner),
lubricant
,
breathing
, and
time
. Copious amounts of each will maximize you and your partner’s backdoor bliss. When all of these are present, you can do the most important thing relating to the enjoyment of anal sex: RELAX.

To maintain and build on communication and trust—the two things that should be present in every sexual relationship—the bedroom is the sexual venue for this chapter.

Take time to make the room—and your partner—as comfortable and as worry-free as possible. If something distracts—or worse, startles—the penetrated partner, it could end the anal experience and make it difficult to return to a stress-free state of mind.

Please also take the time to clean yourself inside and out before you proceed. If tonight’s “the night,” slip something comfortable in, namely an anal douche or enema, before you slip into something more comfortable. Fans of anal sex will even involve their partner in the cleansing process, which adds another level to the experience. You can buy enema bags or bottles online or from any drugstore.

Warm-Up: Rub Them the Right Way for Trust and Relaxation

The five elements necessary for pleasurable intercourse (
communication, trust, lubricant, breathing,
and
time
) are not only essential for engaging in anal sex, they are also key ingredients in a time-honored sensual practice: massage.

The gentle and caring
laying of hands
can convey an entire love story to your partner. A massage also steadies our breathing and calms us. And because massage is intended to relax us, it takes time and patience—a lesson that applies to the enjoyment of anal intercourse as well.

Both our skin and rectal lining lack lubrication, and one of the best all-natural lubricants for massage just happens to be my favorite lubricant for sex: organic coconut oil. Solid at room temperature—“sex butter”—and ready to melt on or in you, coconut oil has a fragrance that evokes the tropics, and it might become your second favorite thing in the bedroom after this book. You should scoop the coconut oil into two saucers: one for the “pre-game show” massage and the other for the “main event.” For hygiene reasons, don’t scoop directly from the original container.

Full-body massages are fabulous, but there are three reasons why a backside-only massage is best in this instance. First, the starting position for sex will have her facing her partner, so we aren’t looking to the massage to establish intimacy. Second, because her breasts and vulva remain hidden while she’s lying on her stomach, his sexual thoughts will not be genito-centric. Third, with her butt facing up and directly in front of him, an end is in sight. Most importantly, faceup-first massages can make many people nervous, because all their vital organs are exposed, and—again—everyone should be relaxed for what’s to follow.

He should take time during the massage to become aware of her breathing, which he can do by listening to her breathe or feeling her back rise and fall under his hands. Straddling her legs and facing her head, he can push down gently on her back and up toward her shoulders, as she exhales, and then let his hands trail lightly back to their starting point when she inhales. He can then rub her arms, legs, feet, fingers, shoulders, and back, staying away from her butt for as long as possible—partly to build anticipation, and partly to keep her from thinking he is headed straight for anal sex. While massaging her, be careful not to tickle her; causing her to giggle will tighten the orifice that you are hoping to relax. An effective and affectionate way to help her stay relaxed is to keep one hand on her at all times, especially because she is face down and cannot see what he is doing. He should focus on calming her and on building trust. He should keep his hands away from the valley between her two butt muscles until she signals that she is ready for the next phase. A simple and practical signal might be that she pulls one knee toward her or under her, which exposes her rosebud to his fingers.

At that point, she is inviting him to explore her ass, but he should refrain from penetrating her. Instead, he should lube his fingers using the other saucer of coconut oil, and then the penetration can begin. She can continue to lay flat, or he can slide a small cushion under her navel to elevate her ass.

He can trace around her anus with his oiled fingers and use one of his smaller fingers with light pressure to penetrate the opening. She remains in complete control, so he should not try to enter her any harder than she wants. To open that first sphincter even wider, it helps if she presses her rectum out, as though she is trying to expel his finger. This phase of anal stimulation provides all the elements of great anal sex, and allows for the penetrator to introduce an ample amount of lubricant into the penetrated area. For a technique that feels wonderful to all receptive beginners, he can insert a finger just up to one knuckle and pull and push ever so slightly while remaining inside of her. I call this game “Tug of Wow,” and it can be used to heighten partner or solo sex.

As she begins to relax, he can switch to a different and equally well-lubed finger, even using two fingers with advance notice and her approval. When she is relaxed, lubed, and comfortable, and when she has learned to control her breathing and the depth of penetration, the couple is ready for the next step.

Though this may seem like a huge amount of time to the penetrator, it is necessary for the penetrated partner. If the roles were reversed—a woman can penetrate a man with fingers or toys (known as
pegging
in street lingo)—men would have empirical evidence about just how important those five steps are for relaxation derived from communication, trust, breathing, lubricant, and time. So, gentlemen, if your partner writes me about what an amazing and patient anal lover you are with her, then I pray she’s got you pegged.

POSITION 1:
The Fireman’s Pole

To help a woman relax during anal sex, she should feel in control. One of the best ways to do this—and one of the best ways to position her rectum in a way to accommodate his cock—is for her to be on top with her hands in his for support. This lets her control the depth and speed of penetration and she can get off at any time she feels uncomfortable. Quite often, when the man is on his back, gravity pulls the blood that should be in his cock to his back, glutes, and legs. Her pull—squeezing her sphincter around his cock as she moves away from him and releasing her anal grip each time she lowers herself onto him—should be enough to compensate.

For anal sex, I encourage clients to have antibacterial wipes on hand, and this would be an ideal time for him to cleanse his fingers, as he transitions onto his back. The first position continues with the trust that the couple has built up to now, and it allows for the woman to manage the depth and tempo of the penetration. It also permits eye-to-eye contact.

Lie down on your back, with your head on a pillow. To ensure your hard-on, stroke yourself as she mounts you.