OK, so you’ve done it. You’ve successfully talked your significant other into trying anal sex. The candles are lit. The music is playing. You’ve accomplished what many men dream of — and if you want to keep living that dream and enjoy anal sex more (or ever find yourself having anal sex again) you won’t fuck this up.
Seriously, don’t fuck this up. You won’t get a second chance if you do.
Fortunately, The Doctor is here to walk you through this and there are definitely more than a few ways you can make sure that she not only likes it but wants to do it again.
- Use lots of lube. Don’t just spit on your hand and rub it on your dick. Don’t stick your dick in her pussy and think that her juices are enough. Use lots of lube. I can’t repeat that enough. Don’t skimp here. Seriously. Don’t. Anal sex hurts the first time or the first few times. There’s no such thing as too much lube.
- Pick the right time to ask for it. Don’t bother her after a large meal at Taco Bell, for instance. That’ll probably create problems with anal sex in general and no one’s gonna have a good time..
- Don’t just stick it in. I know you’re excited, but you’ve got to rev the engine before you start driving. Eat her out. Start with a finger in her ass while you do it, especially if it’s your first time. Anal sex is still sex. Do what you normally do but, you know, with anal. It also helps to try different anal sex positions and find what works best for her. Remember: anal sex hurts at first even if you do it 100% correctly. My significant other likes to be on top when having anal sex for instance, so she can control it.
- Don’t be afraid to enjoy the benefits of delayed satisfaction if she’s new to it. Maybe work up to it over a couple weeks. Use an anal trainer kit if you want (you can buy sex toys like that at Doctor Buttstuff’s store). Work up to having anal sex. It’s not a race to the finish and if you treat it like that you definitely won’t have anal sex again anytime soon.
- I can’t emphasize enough how awesome anilingus is. If she’s opening up the field, have some fun with it. It feels great. I don’t care if you think it’s gross. She’s probably doing this for you (at least at first), so you should reciprocate.
- Give her a backrub. Buy massage oil. The more relaxed she is, the better having anal sex going to feel for both of you. And if you want to have anal sex again, you’ll want to make sure she comes out of this feeling great.
- If she says stop, stop. If you do that, you can revisit it later when she’s more comfortable trying anal sex. If you don’t, you show her that she can’t trust you and trust is a huge part of what you’re doing here. If she wants to stop, you’re going to be tempted to stick it in her pussy instead. Don’t do that either unless you wash up first. You might give her an infection and no one wants that — especially her. As I have already said, don’t fuck this up.
- Feel free to make it as “naughty” as you want. That’s part of why she’s doing this. Go all “50 Shades” on her — not the “misogyny and domestic abuse thinly disguised as a romance novel” part of course, but handcuffs and blindfolds can go a long way in her feeling like your dirty little princess.
- Finish the job with oral sex. She did something awesome for you and she might be a little sore from having anal sex so you want to end it on a high note. You want her to remember how much you appreciate her opening every single hole to you, so eat her out some more. She’ll appreciate it and you’ll have fun. It’s a win-win.
- If there’s a mess — and there may be — don’t tease her about it no matter how funny you think it is. Or you can take preventative measures. An anal douche can go a long way in paving the way for anal sex. Lay out some towels. In any case, don’t make a big deal about “cleanup.” Also, cleanup is your job. Deal with it.
In short, use lots of lube, show respect, and do all you can to make sure she wants to have anal sex again.
After all, you don’t want to go through the trouble of convincing her to try anal sex just to screw things up by making sure she has a bad experience. You want her to enjoy anal sex more than she thought possible. It’s that simple.