If you end up spending a night on your own and you find yourself tired of the same old masturbation drill, consider the anal option. Both guys and ladies can enjoy a nice evening of anal masturbation -- soft candle light, sensuous music, lots of lulling lube, and butt hole. Even if you don't have an orgasm from anal masturbation alone, you can have hours of sensual pleasure, and when you do add genital stimulation into the picture, the eruption can be heavenly.

To start yourself off right, there are two things you want to do: get yourself relaxed; then get yourself horny. When you're horny, your anal walls swell and get sensitive. And when you're relaxed, the anal door opens more freely to guests.

Relax by taking very deep breaths. Deep breathing helps you relax overall, helps your circulation, and helps you to become more aware of your senses. As you inhale (to a count of ten) think about your butt hole expanding and make a note of the sensations you're having there. Expanding your butt hole on inhale and releasing on exhale is good practice. Study this process because if you're going to be inserting things, it's step one in an insertion process that allows your butt hole to "suck in" a dildo or penis. Practice can build the sphincter and other rectal muscles into a more powerful suction machine.

Once you're relaxed and aroused, it's time to party. Get out the water-based lube. If you're new to the joys of anal masturbation, all you may need are your finger and some finger condoms (or skip the finger condoms, depending on how "anal" you are about cleanliness).

Oh, and a mirror. The mirror has a dual purpose. It can be very stimulating to watch your finger playing around and in your asshole. And since there's a component of self-nurturing to your private butt play, the mirror also gives you the opportunity to inspect your sphincter for good health. Position yourself so that you're comfortable, you can easily reach your butt hole, and you can watch what's going on. Check to see there are no swellings, that it's not red, and so forth. And then enjoy its good healthy texture; its perfect form, the way it moves under your finger.

Start by massaging the outer ring; watch it pucker or pull apart. Meanwhile, masturbate your cock or clit; get yourself hard or wet. Notice that there's an inner and outer muscle -- you may want to explore them in the mirror before fully inserting your finger. Do this for awhile, watching and enjoying, letting yourself drop into deeper relaxation by degrees. Notice whether or not your asshole wants to cringe closed. You'll want to work yourself calmly toward an anal opening that looks and feels loose.

While concentrating on relaxing your sphincter muscles, breathe in and push your sphincter out. Touch your fingertip to the opening, then stop pushing as you exhale. You can squeeze your sphincter closed and watch/feel your fingertip slide in.
If it doesn't go this easily, return to "relax." Try inhaling to a count of ten and exhaling to a count of ten. Do this for a couple of minutes, then go back to the formula:

Massage
Relax
Push out
Suck in

As you work your finger deeper into your anus, you'll be learning about your inner curves. Take mental snap shots of those curves.

If you're used to entering a vagina (or you have a vagina) this is your chance to readjust your mental image of the passageway in question. Unlike the vagina, the rectum is kind of S-shaped. Feel free to explore it. On your way to deeper territory, you may find that your finger hits an impasse. This would be the hairpin turn that occurs right where the "sling muscle" cradles the rectal walls (creating an elbow). Not to worry -- you simply need to adjust your angle so you're not hitting a wall and the finger should ease on in.

Let this part of the process be ruled by the spirit of exploration and discovery. Ask yourself questions about your internal design and feel out the answers.

Make a mental note of the curves of this passageway until your finger is as far in as it can go. If you're a guy, this would be the time to feel for the little node on the forward side of your rectum (navel side as opposed to backbone side) that is your prostate. A slight massage here -- in small, soft circular motions -- might drive you wild, especially if you are also slowly working up and down your shaft with your free hand. Ladies, you will want to be massaging your clit or perhaps using thumb and forefinger of your free hand so that you can be working your clit AND giving yourself double penetration.

Now, while you're creating all these exciting sensations, whether you're a guy or a lady, you should let your wildest fantasies loose in your mind's eye. Fantasy is half the fun, and anal stimulation may conjure up new fantasies you never knew you had in you.

So this is a pretty easy process that should have you moaning at your own command. And here are a couple of variations:
-- Instead of inserting the finger deeper right away, you can go for wider by inserting two fingers, then possibly three. Use the same process of relaxation and arousal to loosen yourself up and make each new expansion go smoothly and comfortably.
-- Instead of using a finger, use a vibrating toy (plus plenty of lube). These sensations can be fun in the extreme.

For a nice, invigorating session of anal masturbation, don't worry about orgasm. Instead, let your goal be maximum stimulation. Consider your private anal session a grand experiment. Try different angles, widths, depths, and various combinations of both hands on and in orifices and genitalia to create optimum sensation.

You may bump into a couple of negatives.
-- Pain or discomfort. Do not be discouraged. Pain simply means you've got a wrong angle, or you're trying to rush things, and probably, you're not relaxed enough. Pull back, try more massaging than pushing or prodding, and go easy.
-- New sensations. The first time you play with yourself anally, some of the sensations you'll have will be hard to categorize. Here's where going slow and being observant come in. Pay close attention to the new sensations while adding something you know you find delicious -- like stroking your dick or pinching your nipples. This is sort of like running a fine wine around on your tongue as you bite into the filet of sole; a kind of disjunct co-mingling. And as you let these oddities play in your mind and over your body, you'll start to develop a whole new sense of taste. This sensual stretch is the payoff, the reason you may want to alternate genital masturbation sessions with anal ones.

Because we tend to store so much tension up in the rectal and sphincter muscles, anal self-pleasuring is a wonderful way to free up not only your sexual energy but more importantly, your capacity for intimacy and intimate connection with another. The problem is that the act of learning about and experiencing these great new sensations can actually be overwhelming when you're also trying to pleasure another person.

For example, in a lovemaking situation that includes anal interplay or penetration, many receivers have trouble asking for what they want. Or worse, they can be hesitant to say "no" to what they don't want. Or they can feel like they might disappoint their partner by saying something is uncomfortable. And when this happens, you get a tight butt muscle and your first night of partnered ass play could end up as nothing but bad memories and resentment. For happy experiences in the land of anal sex, the "grin and bear it" approach doesn't work very well.

Self-pleasuring is a way to combat this weakness. When it's just you, your toys, fingers lubes, and asshole, you're more likely to give yourself permission to not like something. Discomfort is usually a sign something isn't being done in the best way. Alone and without the pressure of wanting to please or wanting to be strong, you should be able to explore the negatives and use them as signposts, either to slow down or try a different approach. The results: first, you'll know what you can handle, what feels good, and how to ease into the more demanding aspects of anal intercourse. Second, having given yourself a relaxing, non-threatening and hopefully pleasurable massage, you will then have a baseline against which to compare future experiences with a partner.

For example, if your intimate anal play with a partner suddenly becomes physically uncomfortable, you will know and can reassure yourself that "anal sex can feel really great" and "it doesn't have to be this way." Rather than, "I guess this is how anal sex feels and I'll just have to put up with it."

In addition to reassuring yourself that there is a fun way to have anal sex, you will also know what that way is, the better for you and your partner to remedy any unpleasant situations. Perhaps it's simply a case of you needing to adjust your position; perhaps it requires your partner entering at a different angle, or more slowly. Without regular self-experimentation, you may not know these things, and as a result, you won't be prepared to create the best partnered encounter possible.

This means, once again, that pleasuring for one eventually has great benefits to pleasuring for two. So get off your butt and get in it.