Getting Anal Sex Right – The First Time

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This article contains things that may make you feel uncomfortable – including poop. If you will be grossed out or offended, stop reading now. It is intended for mature, open-minded adults only. Thanks.

Anal sex can be tricky to get right, especially the first time. And since it’s something many people have questions about, I’ve decided to write this brief overview of a couple easy-to-do anal techniques. If you or your partner are hesitant about trying anal sex then admirable sex advice bloggers Dan and Jennifer have a nice video aimed at helping you decide if this is something you should try. If you decide it is, then by all means use one or two of the below suggestions. Remember this should be fun. If it feels like a chore or icky or whatever then it’s not going to work! Relax!

Note: These techniques are written from a female/male (penetrator) perspective, but can be used on any willing, um, A-Hole of your choice!

Easing Your Way Into Anal Sex

Step 1) You must both be “in the mood” for any anal action to happen! I can’t emphasize the importance of being turned on enough. To start, a nice relaxing bath/shower is a wonderful idea. Do what ever it takes to get your partner as excited as she could possibly be. For some women this may be half an hour of oral enticements, for others it may be a kissing marathon, it doesn’t matter. But whatever road she chooses, do it until she’s literally dripping for you.

I’m not sure how much men do or don’t understand this, but there comes a point during prolonged “foreplay” when women feel an urge to have something inside them. No kidding. It goes beyond reasoning and straight to instinct (at least it feels that way!). You’ll know when she’s reached this blissful state of need, usually because she’ll say things like, “Please, God please now!” or “I need you” or, if she’s the straight forward type, a simple “Fuck me!” will undoubtedly clue you in.

Step 2) Now you can go ahead and start with the lube. And then More Lube. And then One Finger. Just one to start…You are Not in a hurry! The important thing for the woman is to stay relaxed and uninhibited. You can help with this by keeping up other sexual stimulation (like circling her clit with the fingers of your other hand, or kissing her deeply…The main point is to distract her from your One Finger). By doing this sensations will start to blend together for her, and she’ll actually enjoy the New Sensation rather than feeling afraid of it. If she’s doing great and still begging you for more, try inserting a second finger. This is when it may become a bit painful, so go slowly and let her tell you when enough is enough.

*Some people prefer putting a condom or latex glove on their fingers before anal penetration. It’s healthier in terms of keeping the bad bacteria where it should be, and makes penetration a little smoother.*

Step 3) Congratulations, you’re ready for the big moment! But wait, before you go plowing into anything just yet, make sure you’re wearing a condom and very well lubed up. Even if you’ve been married for ten years and never use condoms, do it this time. The bacteria in that particular part of her delectable anatomy can cause your most precious pecker a not-so-precious infection. Consider yourself warned.

And like the rest of this journey, your mantra should be “Go Slowly!” In fact, why not let her be on top? If she is willing, the woman-on-top position is the best for first time anal sex because she can control the pace and depth. It also puts less stress on the sphincter which means it’s be more comfortable for her and less likely to cause small tears/bleeding due to the inevitable stretching. Once you’re in and out a few “painfully” slow times, she’ll probably get used to the new sensations and set a pace that’s good for you both.

If you both made it happily this far, great job!

Step 4) Clean up. Once your orgasmic fantasy sex is over, please take a moment to wash up with soap and dispose of everything carefully.

Now That You’ve Read the Do’s, Here are a Couple Important Don’ts:

1) If something goes wrong please don’t be embarrassed to go to a doctor asap! Anal sex, especially if done roughly, can cause real medical problems. If she experience abdominal pain, bleeding more than just a small toilet “wipe,” or if he experiences itching, burning, etc. go to the doctor!! Trust me, it won’t be the first time they’ve seen this stuff.

2) Don’t make a big deal about the “brown” on the condom – if there is any. Be an adult and don’t embarrass the person that just allowed you into her most sensitive place! This will certainly be the first and the last time if you do.

One way to avoid this is to try and go to the bathroom a few hours before the intended sex – but this is admittedly hard to control. Other people use water enemas to “clean out” the passage…But that’s a whole other post in itself.

3) Don’t expect to complete the entire process on your first try. It takes most women a lot of time to get ready for this (mentally, physically, and emotionally) so expect to break down the steps into a few sessions that build up. For example, try one finger the firs time and then continue with your “regular” sex routine. Try two fingers the next time, etc. Building it up in this way will make it seem less scary and more approachable. Be willing to talk through any of the fears or discomforts that come up.

4) Don’t expect anal sex to be an every-time-sex kind of thing. Even if you both had an excellent time, many women like to save anal sex for “extra special” occasions. Then again, a few women love it so much they want it that way or no way…But those are the exceptions.

That’s it. I hope this was helpful to you. If I missed something, or you have another technique that you’ve tried and loved, leave a comment and let us know!

Other Helpful Resources:

Expert Guide to Anal Sex – DVD
Anal Sex Secrets – DVD

Anal Pleasure Toys:

Anal tool – Probe
Pearl panther – Rabbit vibrators
Thai Anal Beads