Luckily, there are things you can do to lessen any pain. While you don't want to drink so much that you get too numb, a drink or two to relax may be just what you both need. The prostate is a walnut-sized gland located just below the bladder and is highly sensitive to stimulation usually gentle finger stimulation through the anus. This is a different experience for you, and you need to gently guide your partner in, not the other way around. From men that have anal sex with their wives, to guys that try it early on in the dating session, these stories capture the essence of the sex act. But a whole dick?
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I actually prefer that. You can use either a external condom which goes on penises or sex toys or an internal condom which goes in vaginas or anuses, also called a female condom for anal sex, depending on your preference. While you don't want to drink so much that you get too numb, a drink or two to relax may be just what you both need. The same applies if you are using sex toys. Be sure to stock up on lube. Plus nothing says I love you like allowing me to stick it anywhere I want. Gay men have, like, the best sex ever.