For this activity, use a butt plug (also known as an anal plug) like the the Buddy. These are usually short, diamond-shaped toys that bulge in the middle, but have a narrow neck at the base. Once the widest part is inside of you, your sphincter muscle contracts around the narrow neck, lodging the toy in place. The toy must have a flared base, which prevents it from slipping up inside you. Choose one with a modest bulge for starters, you can always work you way up to something larger.

• Prep. Make sure your fingernails are trimmed and clean. Keep a bottle of thick lube like Maximus nearby (the pump-style is most convenient). Make sure your toy is clean and has a flared base.
  


• Get in the mood. Listen to sexy music, read or watch erotica, play with yourself in the mirror—do what you usually do to get yourself excited.

• Get comfortable. Experiment with a couple different positions to find the one that is most comfortable and gives you access to your butt. Lying on your side leaves one hand free for your clit while another reaches back to your anus. You might try lying on your stomach with a vibrator strapped on or propped underneath you, and one hand reaching back between your legs. Or you might prefer to squat—a great position for getting a good look at your anus in the mirror, and for easing down gently onto a toy. You can also try this in the shower, and enjoy the combination of warmth, water and cleanliness.
  


• Have a look around. If you’ve never seen your anus, get out the mirror and have a look. Apply some lubricant to your fingertips and explore the skin all around the anus. Then gently tap on the anus, watching how it reacts as you do, noting any special sensitivity as well. Breathe deeply, focusing your mind on relaxing your butt muscles (unclench them if you’ve tightened up).
  


• Fingers first. As you exhale, gently insert your fingertip in past the anal sphincter, which has a tendency to contract when it meets resistance. If you have difficulty, massage the anus, and try pushing out (as if you were going to the bathroom), as you push your finger in. Once inside, hold still while you get used to the sensation. When you’re ready, move your finger around as much as you feel comfortable—many people enjoy a gentle circling motion—do this as long as it’s pleasurable.
  


• Slip in the toy. Withdraw your finger, add lubricant to your butt plug, and then try to insert the toy. If your toy is long or a bit soft, it might help to hold the toy near the top and guide it in. If you have trouble, stop for a bit, massage your anus, relax your muscles and try again. It might help to change positions too. Once inside, hold still with just a bit of the toy inside you, rather than pushing it in to the hilt, as your rectum will need a minute to get used to the object coming up (rather than going out). If you feel the urge to push out, that’s natural, since your anus is used to expelling objects. Try to relax your muscles and this feeling should diminish somewhat.
  


• Nice and easy wins the race. Once inside, slowly push the toy further in if it feels good. Keep adding lubricant, because slipperier is better. Your butt plug should get smaller at the base, and when it’s inserted as far as it will go, it’ll stay lodged in your rectum. At this point, you can leave the toy in place and go on to stimulate other pleasure points, or you can explore subtle variations in movement—try turning it slowly, gently pushing or tapping on it, or turning on/up the vibration if you’ve got a vibrating plug. (Some women find the vibration distracting, but I think it’s nice to have the option—you don’t have to have it on if it bugs you!) If you’ve chosen a butt plug with a gentle curve, make sure you insert it so that when it’s inside your anus the curve points toward your stomach. This position may indirectly stimulate your G Spot.
  


• Get a move on. Because the plug is designed to be “worn,” you are free to get up and go about whatever  business you like. I suggest spending some time exploring different possibilities—walking around the house, taking a stroll outside, cybering someone on your computer—anything that’ll keep you tuned into the sensations in your butt. Chances are, the longer you go at it, the more turned on you’ll get. As you get more practiced with the toy, this can be just the thing to get you “in the mood” for an adventure with a partner later on.
  


• Finish yourself off. You can just enjoy your anal plug and then remove it when it loses its thrill, or you can take your play to the next level, and try to orgasm with the plug in place. Get in a position that is both comfortable and gives you access to your clit. Use your favorite vibrator or your hand to masturbate until you come. You may want to remove the plug quickly after you come, but remember to do so gently.

Wait! You might also find…

• If you find you like movement in and out of your anus, try a slim dildo like the Mistress rather than a plug. To get a better grip, use a dildo with a long handle on one end or one of the bent double dildos like the Nexus.
  


• If you get one with a suction cup on the base, you can attach it to a wall, back yourself up against it, and penetrate yourself without having to use your hands.
  


• Use a dildo in your vagina and a vibrator on your clit while you have the butt plug in place for do-it-yourself double penetration.
  


• Your partner can insert your plug or dildo too, if you want to try this activity together. Just make sure it’s well-lubed, and that you’re in control of the action—ie., you say when to stop, go, speed up, or pull out.
  


• Anal beads or rippled dildos are another great toy for exploring anal play, as the sphincter muscles contract around each bead as they are inserted, which many find pleasurable.
  


• If you don’t want to worry about toy cleanliness, invest in a silicone plug or dildo. These are non-porous so you can wash them off easily with soap and water. Porous toys (those made out of rubber and cyberskin) can also be used with condoms.