When you are both ready for more, here’s how you massage the anal opening. First put on a glove. You might want to start with just the one hand. But eventually, you’ll want to use both, so keep extra gloves handy. Then take a long time to caress the outside of the anal opening lightly. Again, make the touch so very light that it hardly feels like touching at all. Often the most intense response comes before there is any firmer touch.
Just tickle with no lube, and be sure to reassure your partner that you’ll not be going inside without asking first. That way, they can really relax and enjoy the great sensations. And do move slowly.
That may be as far as he wants to go, and that’s just fine. However, if your partner wants more, put lube on your gloved fingers and caress slowly and lightly. Here’s the most important part: pay close attention to what your fingers are feeling.
Let your finger do the walking, millimeter-by-millimeter, as you explore the skin at the anal opening. Remember that the one of you receiving this external anal massage is feeling tons of sensations through the millions of nerve ending there. Even though it may not look like a lot is happening, you can be sure it is having a fab impact.
Some specific moves to try:
Start in the middle of the anus, slowly stroking outward with the tip of one finger. Then reverse, stroking from the outside toward the center. You can put the pad of your finger on the anal opening closer in or further out and make lighter or firmer circles all around the opening. Just remember: slower is better.
Flatten your hand, then you put the little finger side along the ass crack. Using lots of lube, slide it up and down, letting each bump on the edge of the hand push a little into the anal opening. Just a tease; nothing more.
Take one thumb and slide it down the ass crack over the anal opening and a little bit further. Then take the other thumb and have it follow the first one. Keep that going like a roundabout for continuous sensation.
Tickle the anus with the tip of a butt plug or a dildo for a different sensation. For real intensity, you can also use a vibrator.
During this focus on anal play his erections may decrease for a while, which is totally normal. Erections will come and go, and that’s fine. When his penis is soft, that doesn’t mean he is not happy. It just means his focus is elsewhere.
External anal massage may keep both of you satisfied◦— even challenged◦— for months before you move on to the exploration of the inside. Or you may find that a few minutes of it has the lucky recipient begging for an internal massage. And it will be different on different days. Just remember the idea is to have fun and make connection, not to meet a predetermined goal.
Getting Inside
Why all this fuss about getting inside? Why a whole chapter on it?
Think about why you have been hesitant to experiment with this kind of sex. Probably, you were concerned about messiness, discomfort or even pain. And rightly so since it does take some knowledge about techniques (though nothing complicated) to avoid discomfort.
The whole process should always be pleasurable, or at least comfortable. Otherwise something is wrong and you need to stop right away. Or try something different or wait for another time.
When you have something, like a finger or a toy, in your butt, it is normal to have the unsettling feeling of needing to poop. But as you get used to anal play and realize the message is misleading, you’ll learn to relax about that.
In a medical office like mine, doctors do internal anal exams by using a little lube and asking patients to bear down as if they were having a bowel movement. Then they slide the finger in, do the checking quickly and get back out. And they just hope that it wasn’t too uncomfortable for the patient.
However, when you are with your partner, the priorities are very different. The idea is to have fun, and that means you should take a lot of time. You can also make sure that he is turned on by giving him genital pleasure. And before entering, you also make sure that he is warmed up with plenty of external anal play.
For some, the external anal stimulation takes only a few minutes before your partner is ready for more, as in, “Please baby. I’ve been waiting for this all my life.” Or he may feel differently; it might take years before he wants you to enter him. Both are fine and normal.
Going inside the butt requires care and attention on the part of both partners, so it is important not to be drunk or high. If it is normal for you to have a glass of wine, that may be okay. However, if you aren’t sober, there’s the risk of emotional upset later, of doing too much too soon and then regretting it. Also if you are not paying close attention, there is a risk of harm to the anal area.
You never, ever want to force anything, either emotionally or physically. If you need to be drunk to be willing to try anal play, just don’t do it. Sometimes, people use drugs like poppers to try to get the anal sphincters to relax. That is a really bad idea. It is much better to take more time, until he has learned to consciously relax those muscles. Until he can do that, what’s the point of rushing? This is supposed to be fun.
Also don’t ever use numbing creams or gels that are often employed to slow down ejaculation. If your body feels pain, you definitely do not want to mask it. You just need to listen to your body, and to keep your common sense engaged.
If your partner is truly ready, here’s how to enter. First, put on a glove. And you use lots of lube because, unlike the vagina, the anal canal does not produce any lubrication.
Remember, too, that you can use band-aids over the fingertips or cotton balls inside the fingers of the glove to avoid giving discomfort. This works really well for just going inside. But you can’t feel much with your fingertips covered. So once you actually get to the stage of massaging the prostate, you won’t want to cover your fingertips. Short fingernails are ideal, but usually they do not have to be super-short.
Remember to keep the penis stimulation going the whole time and to watch him closely. Is he holding his breath? Is he catching his breath? Do you hear a little gasp? All three are signals to slow down. Also watch his face for reactions. The breathing part, by the way, applies to you as well as your partner.
Back up for a moment. You have one hand on his penis and one hand on his butt. Then you ask, “May I go in?” and wait for an answer. This is really, really important. Don’t ever surprise him. Provide him with warning, as well as with a chance to say no. If he does say yes, still take your time and go in slowly.
The funny thing is that, very often it is difficult to tell for sure where the anal opening is. So it is totally okay to put your finger in one spot and ask, “Is this the right place?” Then request that he push down, as if he were having a bowel movement to help him relax his sphincter muscle. Now you press in with your finger tip, as if you were ringing a door bell. Push a tiny bit and stop, giving you both time to get acquainted. When you feel the muscle relaxing, gently push in a bit further. Just this much is bound to be exciting. You really don’t need to rush in at all.
At this point if he says “stop,” don’t remove your finger abruptly, that is too startling. Simply stop moving and then slowly slide out. If he does not like your finger inside, then revert to gentle external massage and wait for another day.
Going inside him can be emotional for the guy. It can be arousing, it can be pleasurable, or it can be sort of just neutral. And if the gal is on the receiving end, the same possibilities apply. It can be an emotional experience, exciting and/or pleasurable. Or it could be not much of anything.
However, for the gal who is doing the finger inside the guy, it can be really exciting for her to be the one who is penetrating. When everything’s working, everybody wins.