Today’s #AskMeAnything comes from a conversation with a friend of mine who has finally convinced her husband to try anal sex. That’s right, plenty of women want to try it, but their partner is the one who is nervous! Curious what the #AskMeAnything is? Check out the official AMA page on my site over here.

Q: Do you have any tips on anal training?

A: Well, yes, I do, and this post is going to be super long because of it. The main thing with anal sex is that everything is about preparation and thinking ahead. Vaginal sex can be spontaneous and wild and crazy, but to be quite blunt – spontaneous when it comes to anal can lead to some very messy and unpleasant surprises. However! That’s what this post is all about, and I’m going to share some of my favorite anal prep & training items that you might want to try. The links are all NSFW (not safe for work) and should only be opened where no one is going to be peeking over your shoulder. ^_^

What do you mean by prep?

First, I mean getting yourself clean down there, and I mean really clean. We all know what butts are generally for, and (unless that’s part of your kink) most of us don’t want to deal with poop. Now, even if you use an enema, and clean, there’s still going to be some clean-up required after anal sex, and sometimes things just happen, but preparing is the best way to avoid nightmare situations.

Getting down to basics, an enema is basically flushing some warm, clean water up into your bowels, letting it sit for a bit, and then letting it go. If you read a lot of BDSM/humiliation stories you may have come across this as a sort of punishment, but I promise that a normal enema isn’t really unpleasant… more just awkward. It’s the addition of things that can make an enema a punishment (like lemon juice, cold water instead of warm, or diuretic things like epsom salt). My favorite one (used by my gay best friend, and many of his gay friends, and they swear by it for bottoming) is this: Beauty Molly Superior Medical Materials Enema Bulb. It’s $8 and can hold enough liquid to do the job and is SO easy to clean – and it’s medical grade. The things you can get at your local sex shop aren’t always the best materials, and some of them are just scary when you consider their sources, but this is a good one.

But how do you do an enema?

Easy. You’ll want some lubricant, I highly recommend KY Liquid Water-based Lubricant. Get a teensy bit on your finger and swirl around the anus, then dip the finger just inside. Wash your hands, get the water warm (NOT HOT) and fill the enema bulb. You’ll have to take out the spout for this part so it’s easier. Then when it’s full, replace the spout, get on your hands and knees on the bathroom floor (definitely bring your phone/book for entertainment) and insert the tip all the way in. Squeeze the bulb to push all the water in, pull it out, toss it in the sink to wash later, and then stay on your knees but put one shoulder to the floor. This is uncomfortable, but necessary to have gravity assist in washing the water up through your bowels. I usually set a 20 minute timer, and then wait – but if you feel “urgency” before the end of the 20 minutes, and you can’t wait, get up and release on the toilet. There will be some mild cramping, and sometimes some fleeting moments of urgency, but if they pass when you take some deep breaths, you’re fine.

This is one of those times where rinse & repeat isn’t just a suggestion, if the water is really cloudy/dirty you’ll probably want to do a second round, but a 2nd round doesn’t take as long. Maybe 5 – 10 mins. Then hop in the shower, and get all squeaky clean. Use some body-friendly soaps like Summer’s Eve Sensitive Cleansing Wash to clean yourself with. In the shower you’ll want to wash the whole downstairs shabang, and normal soap can be drying and irritating – definitely not what you want before sex of ANY kind. Also, side note, the summer’s eve wash is great for post-sex too because the whole chemical balance can get knocked off and this helps.

What about the actual anal training?

Let’s be honest, you want your anus to be tight. If it were really loose you wouldn’t be able to hold in much of anything, and it is because it’s so tight that anal sex can be a bit painful without the right prep (& also why many men enjoy it so much!). So, warming yourself to the idea of anything going up there takes a bit of time. I always suggest grabbing some lubricant and trying it in shower first. Turn off the water, kneel down or crouch down, get some lube and start out with one finger, then two. Trust me, you will want to know what this feels like before someone else does it first. It gives you time to ease into it, work your way up. Once you’ve done your fingers, you can “graduate” to larger items. Let’s talk about those options…

Staged dildos – There are about a million varieties on the internet for these, but for these I prefer something a little “softer” for first starting out. This set on Adam & Eve are nice, although the small and medium are MORE than enough, the large is a pretty big step-up for anal play and unless your partner is larger than the “large” I’d maybe set that one aside for vaginal play. These are nice in my opinion because you have something to hold on to and really control the insertion, but they still have a solid enough base not to “lose” them. IMPORTANT NOTE: If you’re not aware, your body will most definitely take something through your anus and not give it back without a lot of help if it doesn’t have a base. This is why people end up in the ER with funny stories because they tried to use something that was not meant for anal play.

Staged butt plugs – Also, a million varieties here, but the cool thing about butt plugs is you can wear them for extended periods to get used to the feeling of something inside you. For actual anal training, I still recommend the dildos because you have more length at a standard width to get used to the stretch vs. a butt plug that has a certain “flare” point, and then it goes down to the much, much smaller section just above the base. Butt plugs are also more challenging for beginners because they get wider faster. These are a great option for plugs because not only are they cute with their multitude of options for the “gem” on the base, there is also a really small one for when you’re just starting out, and then another one that is still not very big. The 2nd one in the set I linked is closer to the actual width for men. Of course, there are much, much bigger dildos / butt plugs / etc out there for if you want to get really adventurous, but I find that these do well.

For both of the above options I recommend patience. Work with them ON YOUR OWN at first so you can control the speed of entry. You can take a break if it’s too big, and stop if you’re not ready for that size yet. The shower is the best spot for this because you can instantly clean off, you just want to make sure that the water isn’t running all over you because you don’t want to wash the lube away.

Lube + patience = fun anal play. No lube and/or no patience = not fun.

That is true for both prep, and for anal sex. Being clean and warmed up before anal sex will make it a lot more fun to do the actual deed (just don’t use TOO much lube, or that won’t be fun either). Having your partner involved in the warm up can be hot! Let him open you up with his fingers, have him talk dirty to you. Nothing is better than being on your knees on the bed, or bent over the side of it with your legs spread, and having him call you a “dirty girl” or have him tell you in explicit detail how he’s going to use you / take your ass / etc. We see it all the time in erotica, and it’s hot for a fucking reason! There’s nothing better than slipping into a mindset as you get warmed up from fingers and/or toys before he fucks you.

For actual anal sex there’s a lot of positions, and you can try as many as you like. On your stomach, on your knees, in a kneel (where your legs are under you, or slightly wider than you, but your chest is down on the bed), etc. You’ll need to figure out what is best for your body type, and you + your partner. It sounds odd but pushing out when they start to insert will actually help. Clenching will hurt, tightening down will hurt. Deep breaths, open up, push out, let them in.

But, what does it feel like?

Aaaaand here’s where we go back to the tried and true of everything when it comes to sex. What feels good for some, may not feel good for others! I get off from being caned, for others that would be an instant safeword! Some women absolutely love anal sex. Their nerve-endings are in the right spots, they are wired in the right way physically to get a LOT of pleasure from it. Others get off on the submission of it (this is totally me) and enjoy it because of the act itself, and all of the dirty talk. Some women just don’t get anything from it. Sorry! But it’s true. Just like every other kinky, sexual thing, some things just aren’t for everyone and it won’t matter how much prep / warm-up you get, if you’re not wired right for it, you may not ever like it.

Trying something new is always scary, and that’s normal. This is something really cool to try, that has a lot of great resources out there, and there’s probably more support around you for tips + tricks than you even know. I’ve captured a HANDFUL of ideas here, and I know there’s a million more. This was the absolute basics of anal training / anal play / anal sex.

What happens… after?

Afterwards, you’ll need to clean up. A shower is best, soap and a wet cloth to wipe off a minimum for both of you. No matter how clean you are, there is still plenty of bacteria in the backdoor of the funhouse to cause trouble, so BOTH parties should clean up. FYI: Going anal to vaginal, or anal to oral are both recipes for infections. Some people still do it, and that’s their choice, but it’s a recipe for a yeast infection at the minimum and much worse things at the other end of the spectrum, so I’m going to state it here that I don’t recommend it. You’ll also more than likely have some air up there that will need to come out at some point, so just be prepared for it. If there wasn’t a condom involved, you’re going to have to let the semen out at some point too! These are all the things that don’t show up in porn, by the way, because they’re the not as fun after work of sexy time.

So, should I try it?

That, lovelies, is up to you. The best part of this is you can order this stuff for yourself, try it out, and see how you feel. Watch some anal porn, read some hot & kinky books with anal play in them, get yourself wound up with the idea that anal can be fun and sexy and fabulous. THEN go forth and try it. Chat with your friends to see if they’ve done it, get some tips + tricks from your gay besties (he’s been my anal 101 guide since we were seventeen! LOL). Either way, whether you like it or not, anal is just another way to experience sex with your partner, and there’s no reason to run from it until you’ve tried it and made the personal decision.

Just remember to go slow, be patient, use a reasonable amount of lube, and relax into it. Enjoy it. Talk dirty. Play out some inner fantasy and HAVE FUN.

I do hope this helps, lovelies, because it’s definitely a topic we want to ask questions about, but often get too embarrassed to actually go out and ask, however anal is one place where knowledge really is power – and I hope this has empowered each and every one of you.

Until next week!







PS – My #AskMeAnything series was referenced in an article on Simply Pleasure on Friday where they linked to my AMA on sub drop! So exciting! Check it out if you get a minute. ^_^