Butt Boys: Sex on the Micro-side

A preamble, my lambs. Butt play for men is still a touchy topic. Nary will you see many straight men rushing to tell of their adventures with butt plugs, toys, and butt sex, much less the enjoyment that can come from it.

We can elaborate all day on why there is still so much taboo around butt play in general, and even more so, butt play for men. My guess is that is has a lot to do with implied femininity due to the act of penetration, thus dislodging the concept of man/masculinity and insinuating (gasp!) potential homosexuality. This concept, of course, has been feminized, and what could be worse for a man than to take on feminine or homosexual traits when neither butt sex nor penetration is not inherent to either identity. Okay, maybe there is also some fecal fear in there for the dirty birds.

But I digress.

Yet the stigma remains, and unfortunately so, because anal play, when done well, can be pleasurable and open up a new world of sexual adventures. Hell, the funny fact about this whole matter is that men have a little bit of a leg up in this game (isn’t that always the case though?) since a man’s prostate gland is more easily directly stimulated, as well as slightly more connected to the pleasure buttons in the genital region.

So this week, we will be taking a plug at two questions, both of which seem to be asking the same thing: How can I provide anal pleasure for my male partner? Don’t worry kitten, we’ve got you covered.

Q. So my boyfriend is bisexual and enjoys being fingered (in and about his anus) and I’m just wondering what the proper technique for that might be? I’m assuming I should first say goodbye to my fingernails unless I plan on using some sort of butt plug.

A. My first question love is, what does being bisexual have to do with enjoying anal fingering? I won’t make any assumptions about why you wanted to include the info, and as a favor to the world and the knee-jerk reactionary militia that can be the Internet, I’d like to assume the best and just think it’s an extra bit of info, not as a reason of why he likes anal fingering.

As far as your fingernails go, if you have Naomi Yasuda style nails, which are amazing and potentially not so anal friendly, I’d say, shed the style for the time being. Shorter nails, while not a requirement, will cut down on two potential obstacles: 1. Accidentally cutting your partner’s anal tissue walls and surrounding area and 2. Cutting down on the amount of stuff underneath your fingernails, post-play (though, let’s be honest, a good washing of the hands should help). The whole idea of fingering an anus is that the pressure will come directly from your fingers, which means lots of direct contact. And those lovely Hello Kitty, diamond-inspired, amazing nails that you can’t wait to put on Pinterest and who can blame you? They might add some trouble to the mix. Lose the nails for now and keep ’em short and sweet.

As far as proper techniques go, like many sexual activities, there never is one failsafe method that works all the time. Everyone is different and responds in their own way to pressure, speed, penetration style, etc. What usually works best is to have your gentleman lie on his back, legs spread upwards to the ceiling. This position enables you to find your partner’s prostate more readily and tends to be the best position to stimulate it. Before you both begin, if either of you are worried about those scary sounding “anal fluids,” I’d recommend maybe having your partner do a nice little cleanse a few hours before intended anal play. Have a little cup of coffee or a laxative if you are about that life. This should get out any creeping and incoming bodily movements. Also, you can always put a lubed up condom over your fingers to avoid any fecal bits, which yes, it is the anus, so there will be some. Some couples feel more comfortable and protected using a condom while anal fingering, some don’t, it really is whatever you both prefer.

Now that your gentleman is in a comfortable position and you are ready with either a lube-condom covered finger or a lubed up finger, start by just massaging the area around his anus, concentrating on the perineum (that’s a fancy word for taint). With your lubed finger, start by slipping one finger in, whether just the top or the whole finger. Again, the key with almost any anal activity is to go slow because this ain’t a race, and there is definitely no anal sex trophy, though feel free to add one to your sex life. Use your finger to softly massage the interior of the anus, changing pressure and movement to your partner’s reaction. At this point, see if you can slip another finger in there, and begin heading for the prostate gland, which is about two inches in the anus, and should feel like a small “bump.” At this point, it sort of a players’ game, and depending on what your partner likes, you can start fondling the prostate to whatever they prefer in speed, pressure, or stimulation. You can always mix it up with another activity, be it involving the penis, balls, or whatever floats y’all’s boat.

Q. My boyfriend and I have already experimented with anal fingering and a bit of anal sex (me receiving for the anal sex part and us both receiving for fingering) we would like to try using a butt plug. How do you get started with them? Do you have any suggestions of types to try for beginners?

While not totally relevant, unless you are planning to make a butt plug from a potato (which I recommend not doing), we have talked about the joy of butt plugs and how best to find one that fits your needs in our DIY sex toy piece! Butt plugs, like any other sex toy, are really a personalized piece. Sure, there are great and amazing toys out there, but when it comes down to you, it’s all about personal preference. Want a butt plug that is no joke? Try a bigger, rounder butt plug that is going to fill you up, to use the phrase lightly. Want to understandably stay in the kiddie pool of the butt plug world? Try something a little more beginner friendly, like anal beads. Of course, the options in between are there, with everything from vibrating to silicone, prostate stimulation oriented, and lube and toy combo packs. If you are just beginning, I’d say start small. I know it can feel intimidating to go into a sex toy store and see the XX Ripple 4000, but remember, you are there for your pleasure, and the good folks who work in sex toy stores are there to help you, not judge you. Plus, online sex toy stores are awesome.

So, musts for butt plug play? If it goes in your butt, it needs to have a flared base. Let me repeat that: anal toys should have a flared base. One more time for the people in the cheap seats: into butt = flared base. I hate to be that off-the-hinge lady with her urban legends about lost toys and items in the anal cavity, but kids, this is a very, very, real problem. Your anus is much stronger than you think it is, and with one fell swoop, a nice little sex toy, sans flared base, can accidentally get swooped up in there, and present one of two options: A very awkward retrieving session, or a very awkward trip to the ER. Please refer to this fine gentlemen, who live-tweeted the retrieval of his anal vibrator. While I appreciate his candid approach to destigmatizing a very real problem, it’s best to avoid finding yourself in that situation in the first place. Flared base, babies.

Another must? Lube. Lube is going to help out in any object or body part going in an orifice. Think of the slip-n-slides of your childhood. When wet, the slip-n-slide was the best ever, right? You can go in and out, slide and all the fun was had. Without water, the slip-n-slide was literally, an extended trash bag that hurt like hell if you tried to fling anything onto it. Take it from the slip-n-slide: lubrication is good. Try and find a lube without glycerin, since it tends to sting some folks. In my recent article, All for One, One for Lube, I talked about how oil-based lubes tend to be the best for anal play, if being used with glass or stainless steel toys, or, use silicone lube if you are using non-silicone based toys. Water-based lube will do in a pinch, but the downside to water-based lubes is, since it is water-based, it tends to absorb and evaporate, thus, many re-applications.

Just like inserting fingers into your butt, you want to go slow, working your way up to what feels good to your partner, pressure and speed wise. Again, it isn’t a race. You both are here to make yourselves feel good and to make each other feel good, so there aren’t “musts” on what that looks like. Work your way up to finding a pace that is pleasurable to both of you.

Again, don’t let the stigma of butt play keep you or partner from trying out anal play, toys, or sex. Anal play is not some dark horse of sexual activity, it’s just another route to having fun. In the end, that’s what this should be about, whether the what is beads, plugs, or fingers. Fun.

Got a ques­tion to ask, sub­ject you’d like us to dis­cuss, or myth you’d like us to bust? Keep “˜em com­ing! You can send us an anony­mous mes­sage via the Ask Us! fea­ture here

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TheLadyMiss

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