The Anal Sex Position Guide (17 page)

Penetrating someone while wearing a strap-on is a learned skill, so give yourself some time to get the hang of it. Start out slowly and follow the penetration tips from the previous chapter for initial insertion. Once you’ve got the dildo inside his ass, begin by rocking your hips slowly toward him. Find a position that’s comfortable for both of you, so you can practice your thrusting techniques.

There are many different ways for a woman to get pleasure during strap-on sex. For some women, when the base of the dildo rubs against the clitoris and vagina, there is enough friction there to feel fantastic. Some women get enough clitoral stimulation from this action to have an orgasm. You should also consider the power of having balls. Some women simply don’t choose a dildo with balls because they prefer a more nonrealistic-style dildo; however, balls do more than make it look real, they extend the base of the dildo and cover more surface area—which means more for you to rub up against. Think about it.

If you want to add a vibrator to the equation, you’ve got several options. You can select a vibrating dildo, which will deliver vibration to you and your partner. You can try to don a wearable vibrator beneath the harness, but this may be awkward and interfere with the snugness of the harness. A better idea is to use the Buzz Me harness, made by Stormy Leather and equipped with a pocket for a small vibrating egg or a mini-vibrator. There are also dildos with hollowed-out bases made for vibrators; choose a small
vibrator that runs on a watch battery or a more powerful one with a battery pack; tuck the battery pack in the side of the harness and you’re ready for vibrating action! For double penetration (one for you, one for your partner), you can buy a double dildo made especially for harness use. The Nexus by Vixen is not an extra-long jelly dildo with a head at each end like the ones you see in adult novelty stores. Instead, it’s a two-dildos-in-one package designed so the harness wearer can have a dildo inside her vagina while simultaneously penetrating her partner with the other end.

Of the anal sex positions covered throughout the book, some work for women wearing a strap-on with their male partners; others take a few adjustments to account for height, weight, and other factors; and some just won’t work at all. I highlight some of the best positions for female givers and male receivers in
chapter 12
.

MANY OF THE POSITIONS
covered throughout this book can also work well when the female partner uses a strap-on dildo to penetrate the male. Some of the same pluses and minuses apply, regardless of the gender of the partners, including which positions work well for face-to-face communication, eye contact, kissing, genital stimulation during penetration, and who’s in control of the action. Here are highlights of the best positions for women as givers and men as receivers, and some tips to go along with them.

With him on his back, if she moves between his legs and remains kneeling (doesn’t lean in to lie on top of him), she can easily play with his penis and balls while she penetrates him. He can also touch himself, leaving her to concentrate on establishing a rhythm since she’s in charge of the thrusting action in this position. A pillow or a Liberator Shape under his butt will help angle his body and give her better access to his anus. He can also reach down and help guide the dildo inside, giving him the ability to go at his own pace. Pretty much the same downsides covered in the previous discussion of Missionary apply here; for example, he has to be flexible enough to bring his knees to his chest or fold his legs back over his shoulders in order for this position to work well.

Like its counterpart, Cowgirl, this is a wonderful position for newcomers to strap-on anal play. If she feels nervous about taking full control of the penetration and thrusting (or if she has limited mobility), Cowboy puts him in the driver’s seat. He can ease himself down on the dildo, then be in charge of the angle, depth, and pace of the penetration; he can find the perfect combination for prostate stimulation. If he likes genital stimulation in addition, he can stroke his own penis as he rides the dildo. Partners can make eye contact, talk to each other, touch each other, and do plenty of kissing. This position makes some men feel especially vulnerable or self-conscious or too much as if they are on display, so make sure it works for both of you. If the man is much taller or larger than the woman, she may not be able to sustain his weight on top of her; in that case, try Froggie position, so that he is crouching over her but doesn’t actually rest his body on top of hers.

Doggie Style is a great position for women who are just starting to explore how to properly wield a new toy between their legs! It gives them a chance to find their center of gravity, practice their hip action, and get used to the rhythm of thrusting. Remember guys, this way of giving pleasure may be brand new to your partner and will take some getting used to before she can master the hip action! If a woman loves to look at, squeeze, or spank her partner’s butt, this gives her the best view and the most access. If couples want to explore dominant/submissive role play during anal sex, Doggie Style can work well to help a woman channel her inner mistress and a man surrender to her will. If he puts his head down while his butt is in the air, his body is angled well for her to stimulate his prostate. A few tips, ladies: Reach around to stimulate his penis and balls; have him come back onto the dildo and show you the speed and rhythm he likes; hold onto his hips to give yourself more leverage. Also, run your fingers up and down his back—for a more intense sensation, use your nails!

For those who enjoy rear-entry positions, Tailgate is a must-try. She maintains her control of the penetration in this position, but he doesn’t have to stay on his hands and knees, so this is a good choice for men with knee problems or less strength. Unlike Doggie Style, Tailgate provides the opportunity for a woman to lie completely on top of her male partner, bringing a new level of intimacy to their lovemaking. Many men will enjoy feeling their partners’ weight on top of them as well as the woman’s breasts rubbing against their back. Plus, she has the opportunity to grind her vulva against the base of the dildo for extra clitoral stimulation. Be aware, though, that both you and she will have very limited access to his penis and balls, so this position is best for men who enjoy anal play without other genital stimulation.

Why should men have all the fun? If your guy is an exhibitionist and likes to show off, or you’ve always wanted to role play your Chippendales fantasy, then it’s his turn to sit on your lap and shake his money-maker! With the woman seated in a chair (make sure it’s one that can sustain plenty of weight), he straddles her lap facing away from her and lowers himself onto the dildo. This is a kind of Reverse Cowboy, where he controls the angle of penetration as well as how deep and fast he wants the penetration to be. She gets to sit back and watch the show—literally! If the guy is much taller or heavier than his partner, this probably won’t be workable.

For couples who’ve tried and enjoyed Doggie Style and want to take it to the next level, give Flying Doggie a go. If he likes fast and hard thrusting and she feels confident in her strap-on skills, Flying Doggie is a great way to give them both what they need. He kneels on all fours at the edge the bed and she stands behind him. She may want to stand on a sturdy stool in order for their bodies to line up well. Ideally, she will come at him from slightly above, the perfect angle for direct prostate stimulation. You can also try Stallion, where both partners stand, and he leans over the bed or a piece of furniture; this position only works, though, if partners are about the same height or she’s taller than he.

In this Doggie-Spooning combo, he lies on his side and she kneels and enters him sideways. As in rear-entry positions, she takes charge of the thrusting, so this can be a good position for men who want to feel “taken” by their partners. This is also a good position for heavier men or those with limited mobility. While she retains a full range of motion, he may be able to take less hard thrusting because he is on his side. For some men, there just won’t be enough direct prostate stimulation to make this position a home run.

In Upright Missionary (right), he lies on his back with his legs up in the air. She comes between his legs and can grab his thighs for support and leverage. She has easier access to his penis and balls as well as his chest and nipples. He can watch her as she penetrates him, which some men find incredibly arousing.

Spooning (shown below) works well for people of many different body sizes and heights. Because penetration is not as deep, when using a strap-on, make sure the dildo is long enough since you will lose several inches. This position leaves plenty of room for him to touch himself or for her to stimulate his penis during penetration. There is plenty of skin-to-skin contact, but some couples may prefer a position where it’s easier to look at each other and kiss.