1. Use lube. I don’t care if you get caught up in the moment. Before you stick your dick in her pussy, you get her wet, and before you stick it in her ass, you slather on lube. It’s not an option. It’s an order.
2. You have no idea how sexy male moans are. If she can’t see you while you’re behind her, make sure she hears you. What’s the point of agreeing to anal if she doesn’t think you’re enjoying it? Show her how fucking into it you are.
3. If she’s never done anal before, don’t stick your dick in her the first chance you get. Start out by using a finger. It’s the gentlemanly thing to do.
4. Go slow. I don’t care if she’s begging for it. You should still take your time when entering her so that she doesn’t scream out in pain. Her ass and her pussy don’t work the same way. You have to remember that.
5. Don’t ignore her clit or her pussy. Use your hands or a sex toy to play with them, so that she has the opportunity to get off, too. You shouldn’t be the only one with an orgasm at the end of the day.
6. Foreplay still matters. You can’t go right for the goods. You still have to put in effort. You still have to seduce her.
7. Squeeze her ass. Slap her ass. Kiss her ass. Do whatever the hell you want with it, because she’s given you permission to play around.
8. Don’t go straight from thrusting into her ass to thrusting into her pussy. That can spread a shit-ton of germs. If she ends up with an infection, she’s never going to let you near her ass again.
9. Make sure she’s completely at ease, because that’s the only way she won’t feel any pain. I don’t care if you have to give her a back massage or whisper sweet nothings into her ear. Do whatever you can to relax her muscles.
10. Wear a condom, even though you won’t be able to get her pregnant. Then, if things get a little dirty, the mess will be on your condom and not on your dick.
11. Or, you can just do it in the shower. Whatever mess you create will get all over the tub instead of all over your sheets.
12. Anal is still sex, so you should still use your signature moves, like pulling her hair and digging your nails into her waist.
13. The point of anal is to do something “taboo.” So you might as well throw some handcuffs into the mix to feel even naughtier.
14. Pick the right time to ask her for anal. It probably isn’t a good idea to initiate it after a visit to Taco Bell. A bad experience will make her swear off of anal for good and you wouldn’t want that.
15. After you orgasm, return the favor by rewarding her with oral. Show her how much you appreciate her willingness to let you into every one of her holes. It’s the only way she’ll ever agree to let you do it again in the future, even if it is only on your birthday.