Free Ride 'Em Cowgirl by Sadie Allison

to lube up, right?
    PRECAUTIONS. Anal play without a condom puts you at risk of sexually transmitted diseases and infections. Anal play without lube risks tearing the delicate lining in the rectum. HE-spot massage is not recommended during any prostate disorder. Please read AND PRACTICE all the safer sex tips in this chapter and in the Appendix at the end of this book.
    Going In For The Thrill
    Your first time can be very arousing—like you’re both virgins again. Go slowly, find the positions you like, feel the excitement build, and enjoy all the naughty new sensations.
    Warm up. Massage his inner thighs and inner butt cheeks, then try some oral love, swirling your hot tongue from his penis, closer and closer to your target. At the right moment, flick the tip of your tongue lightly on his tightly puckered anus You’ll not only send tingles throughout his body, you’ll swell his HE-spot so it’s easier to find and primed for your sensual touch.
    Lube up. Slather the sex lube on everything that will enter him. Try a nicely flavored lube if one of those objects will be your tongue. Now gently press your slippery fingertip onto his pulsing anus as your hot mouth once again finds his throbbing penis.
    Butt in. Slowly, sensually, insert your fully lubed index finger (or middle finger), inching it along the upper wall toward the base of his penis. Feel his rectum naturally curve toward the front of his body, along with the natural curve of your finger.
    Play around. Now that he’s all slippery-tight around your finger, softly wiggle it, adding a slow twist or two, or just leave your
    Dr. Sadie Sez: Just How Good Does Your Fingerplay Feel?
    Hmmm. Let’s see. You have an anus that’s just as sensitive, just as tight, and just as excitable as his. Does THAT give you any ideas? Perhaps you’ll take a test ride on a finger or sextoy yourself?
    finger still so his muscles can relax around it. The further in you go, the fewer nerve endings you’ll find, which means he’ll start responding more to pressure and rhythm than the touch and vibration that works so well closer to the entrance.
    Touch his spot. As soon as your second knuckle disappears inside, curl your finger toward his belly button, and feel around for a firm, round bulb that feels like the tip of a nose. That’s his HE-spot!
    Pleasure his spot. Using slow, gentle, “come here”-type curling motions, fingertip his HE-spot with the same pressure you’d use to rub your own eyeball. Run your fingertip all around till you find what he likes—up-down, side-to-side, off-center. Don’t stop your oral loving or handjob, either.
    Talk to the spot. Check in with him: faster? slower? softer? harder? (but not too hard). Keep stroking his penis or playing with his balls, too. You’ll know you’ve got it right when his legs spread wider, his breathing gets faster, he’s moaning or screaming and riding your finger like the stud he is.
    Bring it on. Whisper “Show me how you like it” and let him move on your now-motionless finger. Remember, unlike your G-spot, his HE-spot doesn’t need as much rigorous stimulation—and the right touch can trigger huge orgasms, even if he doesn’t have an erection.
    Rest your finger. Try a prostate stimulator. These are toys curved to stimulate his prostate and vibrate him to new spectacular orgasms. Or try a strap-on with a dildo (“pegging”) for advanced HE-spot loving (see chapter 18).
    Not Gonna Do It? You’ve Got An Alternative
    If he’s too squeamish to let you slip your finger inside, you can actually stimulate his prostate from outside his body—and although it probably won’t give him an orgasm, it’ll still feel great.
    Drizzle some sex lube onto two or three of your fingertips, and press them gently into his taint (perineum). You can also make a loose fist and rub lightly with your knuckles, directing your pressure up toward the base of his penis. Try circular strokes or back-and-forth pressure till you find what he