Best positions for first-time anal sex?

Question: 

I was here earlier. As a general update, I've been using plugs generally whenever I have a bowel movement and masturbate afterwards. I've noticed that it's now pretty easy for me to put a rather large (1 inch at widest point) plug in, but I'm still a bit too scared to use my dildo.

My BF(22) is the same size as the dildo, so I know it will be a very good thing to practice on, but I don't feel quite ready yet. I suppose the more I use the plug, the better I will get at taking things. Anyway, my BF and I want to try anal sex, but we're a bit lost as to what position is best for first time. He suggested leapfrog, but then I worried about him putting his weight on me. I don't feel comfortable using that for something I'm still scared about trying.

What position helps for as little discomfort as possible? And what type of lube should we use?

Our plan right now is a nice shower/enema to clean up (do I have to poop or is that not required? would a laxative be best then?), an oil massage, a couple of drinks (I relax quite a lot back there) and then ease into it with plugs and fingers.

But no clue on position or lube, or what to do afterwards. My biggest worry is that we're going to try it, and I'm not going to enjoy it at all.

Answer: 

Spooning on your left side is almost without question the best way to start out. You lay on your left side with your right leg ahead of your left and your knee bent so that your body is shaped like a lower-case 'h'. This is the position that the medical world uses for all sorts of procedures requiring entry into the rectal area. It is the most natural position for the body to relax the sphincters and it also creates a perfect path for the penis into the rectum.

It also prevents the receiving partner from being smothered.

It also gives the receiving partner easy access to her clitoris (which I highly recommend for anal).

With all that said, I strongly urge you guys to start out just doing some anal play for a while. Keep playing with plugs (analingus really turned my wife onto anal sex, she prefers it now). If it takes a few weeks before you're comfortable trying the penis, then wait at least that long. Moving too quickly can sour the experience, but moving only as you are feeling comfortable to do so gives you the best chance of being one of the girls who discovers that anal sex is actually intensely pleasurable once you conquer the mental block.

My wife and I do a lot of anal sex and have been for a while. We have written a fair bit of info directed to curious couples like you. The older articles have a lot of tips on how to get started and so forth. You might have a gander at some of the first ones. There is also some info about cleaning out beforehand, etc. Do not use a laxative. Generally just having evacuated within a few hours is adequate for cleaning out, then a shower and a soapy finger exploration can confirm readiness. If needed/preferred, a small water bulb to clean the rectum is great, but avoid large bag enemas and never take laxatives of any sort. That will get your entire system moving. If anything, immodium (which slows down your system) would be a better preparation and then a cleaning of the rectum would be the last step - for someone really worried about it or doing a really long and deep session.

Ask your question:

If you need to attach photographs or audio, do it here.
It is optional and we will not publish it. This will be used only to let you know when you question will be answered.