A new Sexuality - Todd Perkins.com
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 Painless Anal Sex...

No pain allowed
NO GO!  

You look at porn it seems common that when someone is first entered anally they make this face and scream in pain.

It almost seems as if this is the way it's supposed to be. I'm here to tell you that most of it is ACTING! It's bullshit! If you have ever watched a video on the making of a porn film you will see that when it hurts they stop action and make corrections. The actors aren't expected to tolerate pain... and you don't need to either!

There should be NO PAIN in anal intercourse!
Pain is the body's way of saying, "STOP!" If you are experiencing pain, something is wrong and you need to communicate with your partner so he does NOT continue. I had one partner who had watched so much porn that he didn't realize that anal sex wasn't supposed to hurt!

So many people automatically connect pain with anal intercourse and it does not need to be that way. There are a variety of things that can cause pain (that can be avoided.) Here are the main ones:

Causes of PAIN:
1. Not being relaxed
 2. Not using enough lube
 3. Going too fast
 4. Going to deep


The biggest source of pain is when the "bottom" (receiver) is not physically relaxed. There are two sets of muscles at the entry way to the anus (internal and external Sphincter muscles.) The external sphincter is voluntary (you can control it) and the inner one has a mind of it's own, it only relaxes when you are mentally relaxed. If you are uptight, then this muscle is also tight.

Physical Relaxation - Role of the "top"

One of the roles of the "top" (person penetrating) is to make sure the bottom is comfortable and relaxed before entering with his penis. Taking your time with foreplay, kissing and touching is a very good start. Before any penetration it's also important to assist the bottom in relaxing their anal muscles. This often entails using a tongue or finger with plenty of lube to gently massage their anus from the outside. To sensually stimulate the anal opening in a slow and gentle manner. This could take from a minute to 20 minutes depending on how you both feel.

After a while the anus automatically begins to relax and desires to be entered. It's at this point that you can SLOWLY insert a well lubed finger into the anus. A slight (up/down) wiggle-vibrating motion of the finger even enhances the pleasure as the finger slowly enters. Once inside, just hold still and allow the bottom to relax again. Once relaxed, do some gentle pushing against the muscle in different directions to open it farther. Avoid a lot of "in and out" with the finger. (The finger is much rougher than a penis, it can get the anal opening sore with too much motion.)

During this time the bottom should avoid tightening his/her ass. Simply relax and enjoy. If the bottom wishes to assist, when a finger is being inserted they can mildly "push" like they are taking a dump and the anus opens more allowing the finger to go in easier.

When one finger no longer feels tight, try pulling out and very slowly going back in with two (well lubed) fingers held close together (having your nails trimmed in advance will help matters!) Once inside, hold still for a bit to allow the muscles to relax, then do some gentle pushing against the muscles in various directions to open it some more. Slowly back out again.

For the average size penis, only two fingers are necessary to open the anus sufficiently to accommodate a penis comfortably. If you have a thicker penis, you will need to repeat this with 3 or more fingers.

This kind of foreplay for anal sex is important for all but veteran anal sex receivers. If the bottom is not relaxed and you try to force your way in, it can cause a stinging pain that is not very pleasant, yet does goes away after 10 seconds or so. The inner sphincter does not enjoy being forced open, and will let your partner know about it!.
Lubing upWarming up with 1 fingerWarming up with 2 fingers

Mental Relaxation - Role of the "Bottom"

Your anus can open to the degree you are relaxed. When relaxed this inner muscle opens to gentle pressure, when not relaxed it stays tight. Your frame of mind has a lot to do with how relaxed you can be.

For many people being penetrated anally takes a degree of trust in your partner. Trust that they are looking out for your safety and pleasure, and trust that they won't do things that will hurt. Communications is the key to maintaining a trust between partners and allowing the bottom to relax. When you feel that the top knows what they are doing and will be gentle, it makes the situation much easier. Make sure you keep constantly communicating with your partner. Let him know exactly how you are doing, what feels good and what feels not as good. Remember the top has no way of knowing when you are getting uncomfortable, so it is YOUR JOB to make sure there is ongoing communications.

Often before anything becomes painful, it starts to get very intense feeling. When you sense this coming, tell your partner to STOP. Explain that what they are doing is starting to hurt. Often the top will intuitively know why this is, and will learn not to do that anymore. But unless you tell them, they won't know.

Another key to relaxing is for the bottom to stay aware of any fears that come up and attempt to work around them. For instance, often the fear that their rectum will be dirty or messy will cause the bottom to not be able to relax. Rinsing out the rectum before sex can reduce this fear. Sometimes fears come up about losing control, simply changing positions can solve that. Whatever else comes up, try to do things to relax your mind of that fear. Taking several deep breaths often helps relax you as well.

Anal exploration can cause some pleasantly intense sensations in your body. Unless you are relaxed, these sensations can be a bit scary at first. If things become too intense, tell your partner. Ask him to slow down, pause, or to be more gentle. Communicating with your partner is the only way for him to learn how what he is doing is making you feel. As he gains more confidence, things just keep getting better and better.

A final note on relaxing... If you are new to anal sex, don't rush things. Take your time! The goal is to learn how to relax so you can enjoy the feelings. Realize that you both may not be able to do this on the first try. The objective the beginning is for the bottom to be able to relax, not for the top to get his dick in. The more you play with this, the more relaxed you get. Exploring your own ass with a finger or small dildo is also an excellent way to learn how to relax.

Take your time! It will be WELL worth the wait!

2. Lube, more Lube, and still MORE LUBE...

Unlike the vagina, the anus is NOT self lubricating. Trying to penetrate a bottom without enough lube is just asking for problems.

A note to tops here... DON'T BE STINGY WITH THE LUBE! Using enough lube is often the difference between being successful and things ending early because the bottom is sore! If things are not REALLY slippery, you need MORE LUBE!

A mistake MOST tops make is not pre-lubing the bottom. If you just put lube on your dick and stick it in, there will NOT be enough lube where it's needed the most, inside the anus by the 2nd sphincter. As you stick your dick in the lube on the head rubs off right at the opening, so the rest of the way in is done with NOTHING! Frankly, if the bottom experiences any pain, it's your fault... cuz your not relaxing them or using enough lube. The trick is to apply plenty of lube to the outside of their asshole as well as gently inserting a lubed finger into the anus. Once the anus is lubed AND your penis is lubed, you should have no problems at all!

Even with veteran bottoms who don't need to be warmed up (opened up with fingers), still place a goop of lube right at their hole before you enter with your lubed penis.

Adding lube during sex

You both are going along and things are feeling GREAT! Then at some point things seem to slowly change. The bottom starts to feel a slight discomfort and the top begins to notice it's not quite as slippery and pleasant as it had been. If you both keep going, things will be short lived. The bottom will say, "enough" as it starts to hurt, and the top will no longer be feeling the great sensations they were feeling. This is a sign that the lube has warn out or dried up! The solution is to simply have the top pull out, put a glop of lube on the asshole (and/or re-coat the penis) and you can continue.

In the early days of being a bottom, I couldn't understand why sometimes I could last a long time and it never hurt, and other times after a very short period of time I would be sore and would need to stop. The secret was the lube. When the lube wears out, it begins to hurt. Now I can tell when it starts to not feel as good, I simply ask for more lube, and I'm ready to go again! It's the difference between being able to be fucked for only 5 minutes or an hour.

Over time you will find some lubes seem to work better and last longer for anal sex than others. Explore and find what works best for you. Just make sure you use LOTS of lube to save your asshole from unnecessary friction!

For an article about Lubes, see: The TAO of Lube

3. Take is SLOW...

This is a message to the tops... SLOW DOWN DAMN-IT!
So many guys have seen these porn videos where the top rams his way in and then is pounding away at it. That may work in the porn videos, but your partner is likely to say NO MORE if you try that right away. Keeping it slow will ensure you partner's comfort and enjoyment of the process. It's not until your partner (the bottom) is really excited and comfortable that you can pound away at them, and even then it depends on how long your dick is and how safe the bottom feels.

If you are with a new bottom, don't even THINK about going fast until a couple months have gone by (unless they ask for it). All you have to do is be really stupid ONCE and you lose any trust you have with that bottom. They might go for YEARS without being willing to try it with you again. It's not worth the risk.

When you are warming them up take WAY longer then you think is needed. Go slow, be patient. Don't think about how it will feel once you get your dick in. Think about giving your partner pleasure by gently massaging their asshole (also called "rosebud".) The more patient you are the more "hungry" the bottoms asshole gets to want to feel something inside. As you massage the outside you will notice the hole slowly opening. As you keep your finger on the outside of the hole, circling around, laying on top of the hole, wiggling, etc... you will notice a point where as your finger approaches the bottom kinda moves their ass closer to your finger. If you held your finger still, they will often raise up and take your finger inside. They won't even be aware that they are doing it. This is how you know they are REALLY ready!

Once you have slowly worked in two fingers, they will likely be ready for your penis. Realize the possibility they may not ever feel ready on the first session. Be patient! When they are ready (they will tell you they want it!) Enter as slowly as you can. Often having the top in a position where they can control the rate of penetration (they ride you, or doggie style-they back into your cock) is best for their first time. Be very sensitive to where they are and make sure they communicate with you.

Once inside, rest until they ask you to go again. Realize they may feel all kinds of odd sensations if they are new to this. Just getting in may be enough. But if all goes well, you can slowly begin moving. The anus cannot take the kind of abuse that the vagina can, it is more delicate until the bottom gets accustomed to the process over weeks or months. Very slow thrusting is extremely sensual and can even be intense. Just holding still every couple strokes can feel REALLY good to the bottom. Paying close attention to your partner you will find out what feels good and what is not so yet. Over time and practice more and more things feel good for the bottom. Again, be patient!

If you have never tried slow thrusting before you might be amazed at how good it can feel for you as well! Take your time and pay attention to your partner. As they become more experienced you can try more things and do some pounding on occasion. For now, take it slow and gentle.

4. Going too DEEP...

Depending on the size of the top's penis, depth can be a MAJOR issue. Realize that the anatomy of the rectum itself is not as large as the typical vagina. As the person relaxes more, the rectum can "open up" and become longer, allowing the penis up into the colon. But this takes even more practice in relaxation on the part of the bottom. When the bottom is tense, the muscles make the rectum shorter, as they relax it gets longer.

You will need to be sensitive to how deep you go, especially the first time with a new partner. Some people can take a longer penis than other people can. The anatomy inside the rectum and large colon varies dramatically in size from person to person. Some people can only take about 5" and others can take objects as long as 12"-15" depending on how tense they are and the shape of their large intestine.

I remember vividly my second time being penetrated. I was so glad just to just have someone inside me again (after 10 years!) that I did not communicate very clearly what was NOT working for me. I just didn't know any better, I thought, "sometimes it just hurts."

Any way, he had a fairly long penis and was ramming me with a fair amount of force. This is normally not a problem, but I was somewhat tense. It was one of those extreme pleasure and pain at the same time kind of things. Well, while it was bareable during sex, I was sore for 3 days afterwards! I was NOT a happy camper! This has never happened since that time, because I learned to relax and communicate when something hurts... it was a valuable lesson!

The penis hitting the wall of the rectum can be pleasant for some, but is unpleasant for most people. Ask your partner to tell you when they feel pressure and slowly go deeper and deeper and see if they stop you. Some couples may never have an issue with depth, others may always have one. As you get to know the anatomy of the rectum this will all make more sense. Just make sure not to go too deep.

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Todd Perkins - Sept 2003
revised - Jan 2005
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