The Teasing Penetration Anal Sex Technique

The Teasing Penetration Anal Sex Technique is a method for gently introducing your man's penis into your body and getting you used to being entered. It is a much more effective way of preparing you for anal sex than fingering. This method should help you if you often experience discomfort or pain initially during anal penetration. Anal sex should never be uncomfortable or painful, and with the Teasing Penetration Anal Sex Technique, it won't be. Best of all, this method not only makes anal penetration more comfortable, but also is quite pleasurable for you and him!


Once you are in position and ready for penetration, grab the base area of your man's penis and gently caress your anus with the head. Just do light, circular motions around the opening. As you do this, every so often allow just the head of his penis to enter you. Squeeze it tightly with your sphincter muscle, release it, and go through the circular motions again. If done correctly, this should start to feel like teasing for both you and him. Yours is the circular motion, and for him, it is the almost getting in and being squeezed, but being denied the chance to slide all the way in.

After a little while, place the head of his penis inside you and then let go of the shaft and place one of your hands just under his belly button, but tell him not to move. With him in place and your hand gently holding him back from pushing, begin to squeeze the head of his penis. Squeeze and release rapidly while in this position. Remember, you are supposed to be caressing the head of his penis with your anus, so vary the tightness and speed. Your goal is to turn him on and drive him crazy.

Next, after doing a few of these, tell him to push in slightly - but only slightly. Give him the chance to do what he has been aching to do since you started, but make sure he only gets a little taste of what he wants. As he starts to slide himself inside of you, make sure you continue to cause friction by squeezing and releasing. This will give you a lot of pleasure, but also will feel very good for him.

It is entirely up to you how far in you allow him to go. It's best to only allow a partial insertion of the penis and then gently use your hand to push him back out. By now, he really wants to go for it, but making him wait a bit longer adds to the fun.

Once he is back to the original position with only his penis head inside you, it is up to you what you do with him. The longer you squeeze and release, the more ready you will be for him. When you feel ready, tell him to push himself all the way up inside you. Both of you will have been waiting for this moment to arrive as you increased your teasing. When he rams it up inside you (and he most likely will ram it), continue to squeeze and release your muscles around his entire penis. He will absolutely love this sensation, and he deserves it after holding out for so long.

The Teasing Penetration Anal Sex Techniques is not only a great way to prepare yourself for anal intercourse, but also a lot of sexy fun for both you and him. Experiment with the technique and make it your own. Don't be surprised if your man doesn't want to begin anal sex any other way!

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

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My First Anal Sex Experience

My posts about anal sex have always been among my most popular with readers, especially my post 10 Steps to Great First-Time Anal Sex. However, my own first-time anal sex wasn't planned (at least by me) and didn't follow the ten steps.

My first anal experience happened during my senior year of high school. My mother was out of town on a business trip, so my boyfriend came over that afternoon after school. We drank my mother's vodka while we watched a movie. It didn't take long for both of us us to get pretty drunk (which helped a lot for what was about to come). Soon, we had forgotten about the movie and were in my bedroom, stripped down to our underwear, making out.

It wasn't long before my bra was off and then my panties. Almost as soon as my panties came off, my boyfriend started going down on me. Back then, being eaten out was my absolute favorite thing, so I just lay back, enjoying the wave of endorphins washing over me. Suddenly, I felt a sensation I hadn't felt before. My boyfriend was running his tongue along my perineum and getting closer to my anus with every lick. There was a part of me that wanted him to stop, but there was another part of me (the drunk part) that was telling me to relax and enjoy the sensations.

I had to admit that it felt good. My boyfriend did the trick where you blow on all the wet spots, and it was driving me crazy! He pushed my legs back even farther and dove right in, I'd never felt a tongue on that part of body - ever - but it felt incredible! He pushed his finger into my butt, and because it was so wet back there, it slid in easily.

When my boyfriend finally came up for air, I was afraid that he was going to try to kiss me. Instead he rolled me over on to my stomach so that I was lying flat on the bed. He pulled off his boxers, and then he climbed on top of me. I was really nervous about what he was going to do next (though I had a pretty good idea). Without saying a word, he pressed the head of his penis against my anus, and I remember whispering to myself, "Oh, my god. Oh, my god." He was really going to put it in my butt, but I wasn't as scared as I though I should be. I actually wanted it.

He used his legs to spread my legs wider. I felt him press harder against me, and then the head was in. He started very slowly, but after a few strokes, he pushed all the way in.

It felt very tight inside, and I thought he was going to rip me at first, but I took deep, deep breaths and did my best to relax. Fortunately, my boyfriend wasn't that big. If he had been any bigger, I don't think I would have been able to take it.

Although it still hurt, with every stroke it also began to feel good. It felt so good that I even put one hand underneath me and got myself off. (I'd never touched myself during partner sex before, so that was another first.) It was a very intense orgasm because of the amazing sensation of feeling him so deep inside me as my muscles contracted. My boyfriend came inside me right after I came .

Afterward, when I asked him how he knew I wouldn't make him stop, my boyfriend smirked and said, "When have you ever stopped me from doing something?" I didn't like his answer very much, but I had to admit he was right. Not long after, though, his cockiness caused him to go too far. To read about what happened, click here.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

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Anal Sex for Beginners

For many people, anal sex is the ultimate taboo. Many people are attracted to it precisely because it's so taboo and mysterious. Others haven't tried it yet and are curious.

What Is Anal Sex?
Anal sex is the act of placing a finger, an erect penis, or object into the anus of another person to give and receive sexual pleasure. Some people also enjoy oral stimulation of the anus, known as analingus or rimming.

Does Anal Sex Hurt?
Anal sex should not hurt. If it hurts, you're doing it wrong. With enough lubricant and enough patience, it's entirely possible to enjoy anal sex as a safe and fulfilling part of your sex life. If you follow these 10 Steps to Great First-Time Anal Sex, you can ensure that your first anal sex experience is pleasurable rather than painful.

Why Try Anal Sex?
For men and women, anal sex is a different, tighter sensation, it’s a little bit naughty, and it provides some variety to normal sex. The anus and the rectum are sensitive areas. There are a wealth of muscles and nerve endings around the anus, and the right kind of touch can feel fantastic. A woman's G-spot can also be stimulated indirectly through anal play as well, and anal orgasms are possible. Anal Sex from Female Perspective describes the erotic sensations a woman feels during anal penetration.

Anal Sex for Men
All men have a prostate gland that can be reached through the rectum. Many men have orgasms just from pressure on the prostate. Prostate Massage for the Ultimate Male Orgasm explains how to massage a man's prostate for his sexual pleasure. Some couples are even exploring male penetration by the female partner with a strap-on dildo, a sexual practice known as Bend Over Boyfriend or pegging.

As more and more of us explore various pleasure zones throughout ours and our lovers' bodies, the anus has received the attention it so richly deserves. In spite of (or is it because of) the pervasive taboo, anal eroticism can become an important part of your sex life, whether as main course or appetizer.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

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How to Have Anal Sex with a Big Penis

Can a penis be too big for anal sex? Probably not, though size does matter. However, a big penis doesn't have to be a deal breaker. With proper preparation, enough lubrication, the right position, and relaxation techniques, having anal sex with a big penis can be comfortable and pleasurable.

1) Preparation. One way to prepare yourself for anal sex with a big penis is butt plugs. Get one butt plug as large as the diameter of your partner's penis and one or two smaller ones. Use the smaller ones as "trainers," if necessary, and work up to being able to insert the largest one. You can wear a butt plug during the day to prepare for anal sex that evening, or wait to insert it prior to foreplay. If you wear it while having vaginal sex, he will love how tight it makes your vagina feel. Once you're able to insert and wear the large butt plug, penetration with his penis should then be fairly comfortable.

2) Lubrication. Since the anal region is not self-lubricating, lubricants are essential to reduce friction and discomfort during anal sex, and even more so with a big penis. A good choice for anal sex is Astroglide, a super-smooth, long-lasting lubricant that can be found at many neighborhood pharmacies. Use as much lube as possible. You really can’t use too much.

3) Position. Though doggy-style may be the most popular anal sex position, it’s not necessarily the best one if your partner has a big penis. Missionary position (man on top, woman on bottom) allows the woman to fully relax her anus, making penetration much easier. Another good position is side anal or "spooning." The woman lies on one side, and the man approaches from the rear. The woman can relax her anus, and the man can easily access the entire anal area.

4) Relaxation. If you have pain when his penis is inserted, have your partner stop, but not pull out. He should just hold his position while you take several slow, deep breaths and relax the anal muscles. Pushing out (as you would for a bowel movement) will help to open those muscles and allow them relax against the penis. The pain should subside though you may still might feel some discomfort from having something pushing into you and being stretched open. Try to stay relaxed as he continues to push his penis in further. Any time it hurts, have your partner stop while you take slow, deep breaths, push out, and relax until the pain subsides.

If the man exercises patience and control, most women will be able to accommodate any size penis using the above techniques. The incredible sensations of fullness for a woman and tightness for the man make anal sex with a big penis worth the extra time and effort.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

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How to Make Her Want Anal Sex

Do you want to have anal sex with your wife or girlfriend, but are uncertain about her reaction? Many women are curious about anal sex, but are scared about comfort and safety issues. Some women who are unwilling to try anal sex with their current partner may have had a bad experience with an impatient or ignorant lover in the past. That's why I don't recommend asking a woman for anal sex without some careful preparation. Instead of asking her to try anal sex, it's better to make her want anal sex.

Anal sex can be very pleasurable for women because the rectum shares a wall with the vagina, and the sexual nerves are actually closer on that side, which makes the sensation unique, stronger and quite possibly orgasmic. My post Anal Sex from a Female Perspective describes what anal sex feels like for a woman. I am a firm believer that once a woman experiences the sensual pleasure that anal play can bring, she’ll allow you to explore the possibilities a little further, and, given sufficient time and patience, will eventually allow you to take it to the ultimate step of full anal penetration.

The key to the approach I recommend is to "train" her to associate anal sensations with sexual pleasure. The next time you’re going down on her (twice as many women orgasm from oral sex as from intercourse), move your hands around and cup her butt cheeks, squeeze and massage them, and then let your finger(s) wander into her crack a little bit. Get her to pull her legs back towards her head (so you can have better access to her vagina), and lightly bite/nibble around her butt in places you can reach, and run your tongue as close to her crack as you can comfortably (for you and her).

You must keep your eyes and ears open during this to gauge her response. If she moans a little louder, squirms a little bit more, or provides some other positive feedback, then go on to the next step. If she jerks away or gives you a negative reaction, don’t press the issue. Just try again the next time and hope for a more positive reaction.

If you’ve gotten your positive feedback, and are confident about proceeding, lube up a finger and slide it down into the crack of her butt and over her anus (this assumes she’s pulling her legs back for easy access). Don’t let it linger there. Just run it right over the anus slowly and see how she responds. Again, judge her reaction to decide whether or not you should proceed.

If you get another favorable reaction, try it again and this time, let your finger linger there, and perhaps perform some light massage on the anus, especially as you are performing cunnilingus on her. Her nerve endings will already be lit up down there, and everything in that area is interconnected anyway. As long as she doesn’t think you’re about to invade, you should get a noticeable increase in positive feedback.

Assuming you are successful, put a little lube on your finger and slowly, with circular motions, stroke the outside of her opening. Then gradually insert your finger inside the anus. Do not move it at first. Just allow her to enjoy the sensation of fullness in the anus.

Slowly insert the finger up to the end and make circular motions with the whole wrist, without moving the finger in and out. These motions will be felt in the vagina. While you're doing this, do something else, such kiss her breasts or stimulate her clitoris. Try to make her experience pleasurable. A woman who enjoys anal foreplay will eventually begin to give anal penetration some serious thought.

Getting her highly aroused goes a long way toward reducing inhibitions. If you take advantage of her uninhibited state, you can probably progress to the point where she’ll allow you to penetrate her anus with a finger, then two, and maybe even proceed to the point of using a small sex toy. The key here is to make sure that you don’t rush things. If you take your time, and let her get comfortable with the idea of anal play, you should eventually reach the point where she’ll seriously consider allowing you to try full anal penetration with your penis.

When she does, be sure to follow the 10 Steps to Great First-Time Anal Sex unless you want the first time to be the last time. A bad experience can turn her off to anal sex altogether - at least with you. On the other hand, anal sex can be one of the most erotic and satisfying sexual practices a woman can enjoy. It's a different, tighter sensation than vaginal sex, and, if the clitoris and/or vagina are stimulated while you're inside her, it can take her to another sexual realm.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

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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.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

Read more »

Which Anal Sex Positions Are Best for Beginners?

Many women are curious about anal sex, but are scared about comfort and safety issues. Some women who are unwilling to try anal sex with their current partner may have had a bad experience with an impatient or ignorant lover in the past.

However, anal sex can be very pleasurable for women because the rectum shares a wall with the vagina, and the sexual nerves are actually closer on that side, which makes the sensation unique, stronger and quite possibly orgasmic. 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.

For those couples trying anal sex for the first time, choosing the best position may make the difference between a painful or pleasurable experience.

1) Doggie Style is probably the most commonly thought of anal sex position. The woman kneels on all fours, and the man approaches from the rear. Though this is the most common anal position, it's not necessarily the most comfortable, or the best beginner position, as the woman tends to tighten up her anus in this position.

2) Flying Doggie is a variation of the popular doggie style position. The man stands behind the woman and places his feet outside the legs of the woman. You'll find that the man will be positioned higher and will be inserting into the anus in a more downward fashion.


3) In the Wheelbarrow position, the man approaches the woman from behind, similar to doggie stye, but lifts the woman's legs into the air. The woman must support herself with her arms only, or lie flat on a bed or chair.

4) The Anal Drop position puts the woman on top and the man on the bottom. You might think that this would be the best beginner position since it gives the woman control over the depth and speed of penetration, but being on top causes the woman to involuntarily tighten up her anus, making penetration difficult.

5) In the Anal Kama Sutra position, the man lies flat on his back with the woman on top, facing the man's feet. The woman should lean as far toward the feet as possible and then commence pumping. This angle tends to maximize anal pleasure for the woman while delaying orgasm for the man.

6) Side Anal is a good beginner position. The woman lies on one side, and the man approaches from the rear. The woman can relax her anus, and the man can easily access the entire anal area.

7) The Missionary position (man on top, woman on bottom) is the best beginner position for anal sex. It allows the woman to fully relax her anus, making penetration much easier. The woman lies face up with a pillow under her pelvis and her legs pulled up. The man should kneel or lie facing the woman and insert at an angle that is comfortable to both. In this position, the woman can relax several muscles necessary for pleasurable anal sex.

Women are often just as excited as men to be venturing into the anal aspect of sex. Many couples find that anal sex is a tremendous tool to enhance their regular sex activities. It's a unique feeling that is completely different to vaginal sex and worth experimenting with.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.

Read more »