10 Steps to Great First-Time Anal Sex

Many people believe that anal intercourse hurts and that it is always an uncomfortable experience. This is quite simply false. If it hurts, you’re doing it wrong. Actually, anal intercourse can provide a unique form of pleasure for both men and women. Anal sex is enjoyable for men because the tight anal sphincter rings provide strong sensations to a thrusting penis.

Generally, for women, the pleasure derived from anal intercourse is due to the shared nerve endings located between the rectal wall and the vagina, and/or from indirect stimulation of the G-spot. The anus contains many nerves as well, which can also react in a pleasurable manner when excited. My post Anal Sex from a Female Perspective describes what anal sex feels like for a woman. If you want to try anal sex with your wife or girlfriend, but are uncertain of her reaction, use the approach I recommend in How to Make Her Want Anal Sex.

If you follow the ten steps below, you can ensure that your first anal sex experience is pleasurable rather than painful.

1) Get clean. It goes without saying that if you’re sexually stimulating an area that’s usually devoted to elimination, you need to ensure that it’s squeaky clean. Have a relaxing bath or shower beforehand and thoroughly clean the area. If you’re self-conscious about your lover seeing your anus in full for the first time, why not gently shave or wax the skin between your butt cheeks? You’ll be surprised how much more relaxed and confident this will make you.

2) Don’t rush into it. Engaging in foreplay or even intercourse before trying anal sex for the first time can help you relax. Analingus (oral-anal contact) is another great way to “warm-up” the anus and can be very pleasurable in and of itself. Run your tongue over the anus, licking it in soft, wet strokes, or circle it, running your tongue around the edge of it slowly and delicately. Flick the tip of your tongue rapidly over the opening, or try inserting your tongue as far as it will go pushing and stroking it back and forth. Try brushing your lips over the spot or sucking hard on the anus.

3) Use lots of lubricant. Since the anal region is not self-lubricating, anal lubricants are extremely helpful for making penetration more comfortable and pleasurable. Water-based and silicone-based lubes work well with both latex and polyurethane condoms. Many couples prefer a thicker lube (a “gel” rather than a “liquid”) for anal sex. Use as much lubricant as possible. You really can’t use too much.

4) Fingers first. The sphincter muscles around the anus will not allow things to pass through easily unless you start small and take it slowly. Apply lube to one finger and gently insert it without moving it around in order to condition her to the sensation of something being in her anus. Once she is comfortable with being dilated, slowly start to move your finger in and out and around. Gently stretch her anus by pushing outward on her anal ring, as if it was the center of a clock face, pressing out towards 1, 2, 3 o’clock, etc. Once she has learned to enjoy the insertion of a single finger, try inserting a second. Always go very slowly and be sure she remains relaxed. Don’t forget to use lube on each finger you insert.

5) Get in position. Choosing the best position may make the difference between a painful or pleasurable experience. Though doggie-style may be the most popular anal sex position, it’s not necessarily the best one for beginners. Missionary position (man on top, woman on bottom) allows the woman to fully relax her anus, making penetration much easier. My article Which Anal Sex Positions Are Best for Beginners? describes several anal sex positions, and tells you which ones are best for beginners and why.

6) Enter slowly. When you’re ready for penetration, take one or both of your hands and use your fingers to pull your butt cheeks gently apart. This will help guide him into your anus without too much prodding, making it a lot easier for both of you. He should begin by slowly and gently inserting the tip of his penis into your anus. Remember that it’s normal to feel some discomfort or even slight pain because it’s your first time (just like with first-time vaginal sex) though if you’re in a great deal of pain or feel very uncomfortable, ask your partner to stop immediately.

7) Go deeper. Once your partner has inserted the tip of his penis, ask him to slowly penetrate your anus further, but at a gentle pace that you feel comfortable with. This means it could take anywhere from 30 seconds to five minutes before his penis is fully inserted. Breathing deeply and talking him through what you’re feeling will help keep you both stay relaxed. Continue like this until his penis is fully submerged.

8) Gradually build momentum. Once his penis is fully inserted, the key to great anal sex varying the angle, depth, and speed of thrusting and gradually building up momentum. Clenching your anus can enhance the sensation for your partner.

9) Don’t forget the rest of her body. Stimulating other parts of her body during anal sex can help make her feel more relaxed and provide a greater thrill for both of you. While thrusting in and out, reach around and finger her clitoris. While orgasm may occur purely from the anal sex, this added stimulation will lead to a more intense sexual experience.

10) At the end. Immediately following climax, she may become extremely sensitive to penetration. Thrusting or pulling out should be done very gently after orgasm. Also, remember that once your penis has been inside the rectum, don’t put it inside anywhere else until you have washed yourself.

These days more and more men are becoming interested in anal pleasure and comfortable with the idea of letting their female partners take control in bed, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It.

Anal sex is one of the most erotic and satisfying sexual practices you and your partner can enjoy. It may take some time to get it just right, but if you follow these 10 steps, you will both have lots of fun trying. The most important aspect of anal sex is communication, so be sure to talk to your partner about your anal desires before, during, and after your first session of anal sex.

You’re reading this because you want to make your sex life exciting. You want to make it hot. Passionate. Mind-blowing. You probably want to find ways to please your partner. OPRAH! love expert Michael Webb reveals how to bring back the fire to your love life. So, if you’re ready to add more heat to the bedroom, click here.