Finger, Cock, Strap-on, Dildo, Butt Plug
I think you see where I'm going with this...
Most men can experience the intense mind-blowing power of an anally-induced orgasm. Women have long written about discovering that their men, even those who are initially opposed to anal play, can be brought around by using a finger in her BFs ass during sex. This is certainly not the same as a doctor doing a proctology exam. It wouldn't do for the doctor to gently ease his finger into his male patient's butt, although it would be better if he did. Our macho, non-submissive-male culture has done a good job of turning most men off anal pleasure. And so, part of the purpose of this blog is to rectify (pun intended) the idea that anal pleasure is something all men should enjoy, without guilt, shame, feeling submissive, or embarrassed.
To avoid the dynamics of complicating this with a partner (male or female), let's begin with a solo experience. I'm mainly speaking to straight men with virgin assholes, rather than gay men, although some gay men are also turned off by anal play.
Start with a finger...
Have a bowel movement, shower, and clean the anus as deeply as you dare with a wash cloth. I think most of us take the time to clean "down there" when we bathe or shower, so touching the back end is not entirely foreign to any man. Now, instead of getting dressed and going out and doing macho things, decide you're going to take time to masturbate before you get dressed. But instead of just laying back and pounding your pole, lay back, put a little lube on your finger, spread your legs (best to raise them to your chest), and allow your butt cheeks to naturally spread open. Begin to lightly apply the lube around your anal opening, and then begin to gently massage that area, focusing your feeling right there, just outside the anal vault. And then start pushing the tip of your finger into the opening. If all goes well (how can you be embarrassed if you're alone?), push the finger in farther and withdraw slowly, push the finger in farther and farther, in a slow steady in and out motion. Almost any man should feel how pleasurable this simple act of fingering himself actually is. Now, you're going on a safari to find that glorious prostate. It's toward the front of your body, not so far in that you can't reach it with your finger. Once your anus goes "zinnng!" you know you've hit the P-spot. Just keep massaging your prostate until you come. Let your body dictate how fast and hard you drive your finger into your ass.
Gay men will move on to a cock; straight men will move on to having the GF use a strap-on, a dildo, or a butt plug...
Of course our busy schedules preclude spending too much time alone engaging in anal play, and that's where extended butt plug use comes in nicely. If you want to edge all day, you can with a butt plug. You can't with a dildo, unless you're going to start wearing a harness, just to keep the dildo in place as you go about your day; but the simpler the better. Further a dildo, with no shaft that allows the sphincter to close around it is going to become uncomfortable too fast. The butt plug is usually shorter than a dildo, as well, since you'll only be wanting to reach as far as the prostate. Anything past that is kind of wasted (no nerve endings to feel it), and if the plug fills the entire rectum (about seven inches deep) it will also tend to become uncomfortable too quickly.
In conclusion about beginning to explore your anal sexuality, don't push yourself. Do only what feels good and not what causes too much pain. Take it slow, use lube, and do it in private for awhile before you complicate your anal play with a partner or spouse.