There's no doubt about it, the thought of anal sex is pretty frightening — especially if you've never done it before.
Even for those of us who consider ourselves pretty open when it comes to sex, anal is intimidating. Between worrying about the pain factor and any mess involved — we've all heard the war stories — anal sex is definitely something that takes some guts to give a whirl.
We asked the sexperts to demystify anal sex for first-timers, and it turns out that certain positions are all you need for an enjoyable experience. Well, that and a lot of lube. For the love of all that is holy, don't forget the lube.
In the traditional cowgirl position, your partner lies down while you mount on top — yeehaw! As the partner on top, you can ease into anal penetration by moving up or down as needed. Pro tip: Make sure your bottom partner does not begin to thrust until you're good and ready.
Certified Master Sex Expert and Educator, Sex Coach and "So Tight" Sensual Fitness Personal Trainer Nikki Ransom endorses the cowgirl position for anal newbies. She explains, "This position will allow you to control the pace and depth that his penis goes inside of you. Remember to go at an easy pace and stay relaxed. It helps to have had an orgasm already and be highly aroused."
Jessica O’Reilly (a.k.a. Dr. Jess, Ph.D.), author, international speaker and PlayboyTV's sexologist, offers an alternative to the cowgirl in her book The New Sex Bible, "If she doesn’t like the sensation of deep penetration, but he desires more stimulation against the base of his shaft, she can reach backwards with a warm, wet hand to grasp the lower half of his shaft. Her hand becomes an extension of her butt while providing a physical buffer to ensure only shallow penetration."
This position is most often associated with anal because it has major advantages. As the partner on the bottom, you can stay loose as you control penetration to increase pleasure. Getting busy on all fours may be your best bet if you have attempted and found anal painful in the past.
Patricia Johnson and Mark Michaels, co-authors of Designer Relationships, Partners in Passion, Great Sex Made Simple, Tantra for Erotic Empowerment and The Essence of Tantric Sexuality, recommend doggy style for first-timers and those who may have had an unpleasant experience before. The couple says, "Anal sex should never be painful. Always use plenty of lube and proceed slowly and gently." Ransom adds, "Rub and stimulate your clitoris too to make it even more pleasurable."
In The New Sex Bible, Dr. Jess has a different take on doggy-style anal sex. She recommends the modified doggy to give the receptive partner more control, support intimacy and provide the opportunity for double penetration. Dr. Jess explains, "She assumes a kneeling position with her butt cheeks on her heels and her knees spread wide open. She places her hands on her knees or the bed for support. He assumes the same position behind her and adjusts his height so that the head of his [penis] rests below her bum. He remains static as she lowers herself onto his head and takes a few deep breaths before sliding farther down his shaft. She drives her butt and hips up and down at her own pace as he reaches around to fondle her breasts or rub her clitoris."
This position is preferred if you are looking for extra intimacy during the act. Start with your partner sitting as you mount his lap, face-to-face. Once again — as the partner on top, you can control depth of penetration to stay comfy. Face-to-face anal has the added bonus of extra stimulation for a woman: breasts, clitoris, go crazy!
Johnson and Michaels love face-to-face anal for the toe-tingling intimacy it provides. They confirm, "This position facilitates using eye contact and breath to build even more arousal."
Dr. Jess agrees. She says, "I like this position as it allows the 'mounter' to exercise a good amount of control of the depth and rhythm of penetration. Wear a vibrating c*** ring for this one to provide extra pleasurable sensations as the top partner grinds against his shaft."
Next Up: Good old missionary with a twist
Originally published January 2015. Updated January 2017.
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