Sexual Relationships 
Sexual Health 
Many people reading this myTake will already have the opinion that anal sex is disgusting, gross, filthy, and anyone who engages in such conduct is a pervert, slut, or whore. If you are one of those people, stop reading this. I'm not interested in changing your opinion and you won't change my opinion, so why bother?
If you have tried anal sex and thought that maybe it could be better . . . well, maybe it can be. I will offer some suggestions that you might want to try. If you have never tried anal sex and you are interested but perhaps scared, I will offer some information and suggestions that may lead you to think differently about "the forbidden."
When we were toilet trained by our mothers, we were told that "back there" is a private place and no one else should ever see it. For most people, having someone see you anus is more taboo than having them see you vagina or penis. That is a great psychological barrier that many people will never overcome.
If you can get over the awful embarrassment of having someone see "where your turds come out," anal sex offers much pleasure which can be added to your panoply of sexual delights. In both men and women, the area around the anus is very highly innervated. This tissue can respond negatively to minimally unpleasant stimuli as well as responding pleasantly to pleasing stimuli.
So, how is it possible that anal sex can feel good in any sexual way? When penetration proceeds beyond the anal sphincter, men and women's anatomy varies. If a woman inserts her finger in a guy's anus up to the second knuckle, her fingertip is applying pressure to the guy's prostate gland. The prostate gland is actively involved in ejaculation and pressure on the gland usually feels pleasant and arousing. (Hint: If a guy enjoys anal play, giving him a prostate massage while also giving him oral sex will make him your sex slave for life!) When a woman has her anus penetrated, she can feel the stimulation in her vagina, because there is only a thin membrane separating the rectum and the vagina.
My advice on how to have anal sex is based on the assumption that you have never done it before, you are scared, nervous, and a bit embarrassed. It is assumes that you have a willing and cooperative partner. I will suggest a series of steps that will take you beyond your fears and inhibitions gradually. If you do not need to take small steps, you can try condensing the many steps into a few. In fact, most people who read this will think it has been broken into too many steps. I am trying to help those who want the adventure but who are terminally anal shy.
It would be supremely arrogant for me to pretend that I can describe what this experience is like for a woman. How would I know? I’m a guy! But I have had anal sex with several partners and I know what they have told me about the experience. So the steps in “how-to” are told from a guy’s perspective. If you ladies have anything to add to this description, please leave comments.
To the extent that it is practicable, I suggest that a guy go through the same steps that the girl goes through - talking about it, showing it, touching it, even experiencing some penetration. A lady is more inclined to think that you will understand what she is doing for you if you have experienced it yourself.
Talking about anal sex. The first barrier is simply talking about your anus and the idea of having anal sex. Decide what you are going to call "it." For most people, "anus" sounds too clinical. "Asshole" sounds derogatory. Some girls are more comfortable calling it their "bum" or "back there." Others say "pucker" or "rosebud." You can call it "Patricia," I really don't care, as long as you both know when you are discussing your "back door."
Talk with your partner about your experiences. "No one's ever seen or touched my bum. If it happens, you'll be the first." "I've never had anal sex but I heard that it can hurt so it scares me." "The idea of having your dick in my ass is really exciting but I'm also a little bit scared so I need you to be patient." "I've always wanted to try anal sex but when I suggested it with other partners, they acted like I was a pervert for even thinking about it."
The more you talk about it, the more it will become "normal" and not quite so frightening. Talking about anal sex before you begin exploring makes it more likely that you will continue to talk about it WHILE you are exploring, and communication is essential to a pleasurable experience.
The first viewing: look but don't touch. If you have been intimate on many occasions, you have probably seen each other's heiney holes. When a guy is giving a girl oral sex, he usually gets a glimpse of the back door, unless all of the lights are turned off. Each partner gets a look at “the promised land” when they are using position #69.
The first time that you are deliberately and intentionally allowing your partner to see into the forbidden zone, have an understanding that this is looking only and there will be no touching. It is probably easier to allow your partner to look at your sinkhole after you are sexually aroused so by all means do engage in some foreplay. Guys, once your partner is aroused, ask her to roll over on her stomach and give you a viewing. She can reach back to spread her cheeks and you can get as close as you want but don't try to bend the rules: no touching! Anal sex requires trust and that means consistently following whatever agreements you have.
Compliment her on having the confidence to do that and assure her that seeing her pink eye has you aroused and excited. Then, man up and offer her the same opportunity. Roll over and give her a look at your back door. Does that make you feel a bit self-conscious? Well, now you know how she felt just a few moments previously.
The magic moment arrives: touching! Anal sex is something that is easy to over-think. If a girl is concentrating on what you are about to do, she can get herself too anxious to be receptive to any pleasurable stimulation. As before, the key to touching is to have her already aroused. The ideal approach is to be involved in mutual oral sex with her on top. When she is right on the edge of having her orgasm, touch the tip of your finger to the middle of her orifice. Don't try to penetrate her but apply light pressure. If you are successful, her orgasm will expand exponentially and she will go wild with sexual abandon.
Now that she has experienced anal stimulation in a positive context, it should be much easier to proceed. Next time you are going down on her, lightly stroke along the folds of her pucker. Her actions will tell you if she wants more.
The penultimate thrill - digital penetration! Digital penetration does not mean trying to hide your iPhone in her derrière! "Digital" in this context refers to your finger. When she is again aroused and receptive, the next step is to penetrate her. This requires two things in copious amounts: lube and patience. Use a quality lube like KY or Astroglide because, unlike the vagina, the anus has no natural lubrication. Most often, girls who complain about pain with anal intercourse either attempted it without lube or without sufficient lube. The second most common problem is that the guy was in a hurry and did not take time to proceed SLOWLY as he should. Guys, make sure that your fingernails are trimmed short and do not have any sharp edges which would cause her pain. You are going in to SENSITIVE territory!
For penetration, you need to choose a position that is comfortable for both partners. The most commonly used positions are doggy-style position, girl laying flat (perhaps with a pillow under her hips to increase the elevation,) or spooning. For anal fingering, spooning is not a comfortable position.
Apply a generous amount of lube to either your index or middle finger and then apply more lube directly to her bum hole. Place the tip of your finger in the center of her pucker and slowly push in until you have just penetrated and then stop! She needs time to accommodate and get accustomed to that feeling. As you pushed in, you probably felt her clenching, trying to resist your effort to penetrate.
This is a reflex, an instinctive action that you will need to overcome when it is time for the main event.
When she gives you the go ahead signal, resume pushing in - slowly - until you are fully penetrated. Stop and let her get accustomed to that sensation. Then start pulling back - slowly - until your finger is almost out, reverse direction and repeat but slightly faster. Before long, she will be accustomed to your thrusting with one finger.
If she is comfortable with the idea, you might try adding a second finger and penetrating again. I think it is preferable to substitute a vibrator or dildo that approximates the size of your penis. Cover it in lube and start slow but she will probably accommodate to the size of this toy much quicker.
You guessed it! The Main Event! If she has been penetrated with a vibrator or dildo that is about the size of your probe, she should not be worried . . . but she will be. She has heard that anal sex is painful, that she will be bleeding afterwards, etc. and she can't forget what she has been told.
Have her as aroused as you can get her, clitoral stimulation, nipple play; whatever it takes, do it. The more aroused she is, the more receptive she will be and the more likely that she will have a positive experience. Again, apply lube to your finger and to her anus and penetrate her with your finger. Ask her if she is ready; it is important to make sure that she understands that she is in control of what will be happening.
Place the tip of your penis at her anus and begin pushing forward. It is quote common for women to instinctively clench their sphincter and that will be difficult overcome as long as she has the gate closed tightly. Suggest that she try pushing out (as if she is trying to empty her bowels, but explaining it in those terms at that moment will probably be a mood destroyer.) Ironically, when she tries to push out, her sphincter relaxes and it is easier for you to penetrate her.
As soon as the tip of your penis pushes past her sphincter, she will probably tell you to stop. That doesn’t mean pull out, get dressed, and go home. It only means that she needs a few seconds to accommodate to this new feeling. If you remain motionless for a few seconds, she will probably start to relax and deeper penetration will be both possible and pleasurable. When she is ready, slowly (that means SLOWLY!!!) push deeper until you have penetrated as deep as you can go. If you have a normal 5-6” penis, you can probably fully penetrate her. If you are one of those guys who posts questions asking “is my 9” pecker big enough?,” she will probably tell you to stop before you are fully submerged. Or she may be too afraid to even let you try anal sex with her. Bigger is not always better.
When you are fully penetrated, again pause and allow her to get accustomed to feeling something in her ass. If possible, reach under her and play with her nipples. If you are in a doggy-style position and can manage it, reach around and play with her clitoris. Any other form of sexual arousal will enhance the experience for her.
After a few seconds at a standstill, reverse engines and begin to withdraw, but don’t withdraw completely. I know that some porn shows guys doing anal, pulling out completely, repeatedly ramming back into her gaping ass. That’s just porn. Don’t do it. Just begin a regular, slow, rhythmic thrusting action.
While you are doing this, talk to each other. “Baby, your ass feels so good, I’m not gonna stop until I cum in you.” “Baby, your dick makes me feel so full!”
If she feels adventurous or even more uninhibited, give her a vibrator to use on her clit while you are thrusting in her ass. Or she can put the vibrator inside of her if she prefers G-spot stimulation. If you do opt to use a vibrator for the double penetration effect, use a small vibrato that she can almost completely bury inside her manhole. If there is much vibrator exposed, you will feel it with your balls and it is not arousing – perhaps even aversive - for many guys.
Tell her when you are close to your orgasm. “Baby, I’m so close to cumming! I need it so bad! Oh, here it is!”
When you cum, it may be the most intense orgasm you have ever experienced. First, you have broken a psychological barrier and a social taboo by having anal sex. Second, the anus can feel much tighter than a vagina and the physical sensations are more intense. Third, one of the important aspects of sex is the trust that is displayed by allowing someone to see you naked and use your body for sex; anal sex is the ultimate test of trust and it can actually make you feel incredibly close to your partner.
Some girls orgasm from anal sex. Usually, the women who orgasm are having some other kind of sexual arousal, either from fingering their clitoris, using a vibrator, etc. Also, women are more likely to orgasm if they can relax and stop trying to clench their sphincter.
After you cum, do not immediately withdraw. Wait for your partner to suggest that you pull out and then do it slowly. After you pull out, spoon behind her, hold I her in your arms, and tell her how incredible she felt. Tell her how wonderful you feel that she could trust you enough to have that experience. Ask her how it felt for her. If she has not yet had an orgasm, it isn’t time to sleep; don’t close those eyes until you have given her an orgasm, either through oral sex, fingering her clitoris, using a vibrator on her, whatever it takes.
If she is willing to try it again, wait a while before you suggest another holiday in the heiney. Don’t make her think that you are going to want anal sex every time you get in bed. Ultimately, you will not want that and her willingness to give you some anal satisfaction is probably based upon the assumption that it will only be an occasional adventure.
Some partners have some conflicted feelings about doing kinky things like anal sex and they don’t really want to have any discussion about it away from the bed and the passion of the moment. So, the next morning, while you are sitting at the breakfast table, don’t say, “Holy cow, it sure felt good cumming in your ass last night! Can you pass the orange juice?”
If your partner did not enjoy the experience, try to talk about it right then and there. Was she unable to relax? Did you not use enough lube? Is it just a psychological thing about “that’s where the turds come out. Nothing is supposed to go in there.”? Some women will never be comfortable engaging in anal sex and, almost always, it is based on psychological factors instead of physical factors. It is as if they have decided they don’t like it before they even tried it. If this is the attitude you encounter, don’t try to challenge it; you can’t win that discussion/argument.
Anal sex is not for everyone. If having anal sex is important to you, find a willing partner and have the experience, But . . . keep it in perspective. Anal sex is just one of many possible sexual activities and if you are looking for a long term relationship, there are many other factors much more important.
I hope this gives you some perspective and insight into a frequently maligned activity. If this was helpful, please leave a comment.
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