NSFWSex & SexualitySunday School

Sunday School: On Pegging

I’m a girl with a bisexual boyfriend. Neither of us have had anal sex or know much about it, but we both want to try. In his case, he wants me to do him with a strapon. Can you recommend me a good one that will give me plenty of stimulation too? Also, do you have any advice for backdoor first-timers? –Pitcher

I have a very excellent rule for anal sex, and it goes like this: if it hurts, you are Doing It Wrong. It applies to everyone, and every time I hear someone complain about a terrible experience they had with anal sex and how they’re never going to do it again because it hurt so much, I die a little bit inside. But that definitely won’t happen to you or your boyfriend, Pitcher, if you follow that rule.

Another almost-equally-excellent rule goes “too much lube is almost enough,” but I feel like that is a corollary of the other.

Anyway. For your pegging adventure, you will need equipment. Making specific recommendations is a little bit difficult without knowing precisely what gets you off, but here are some guidelines.

1. You will probably want to get a harness–there are several nice double-ended options that don’t require one, but without a harness they tend to offer less control, especially if you’re planning on doing anything vigorous (or are still trying to figure things out). Nylon costs less than leather and is easy to clean, but it’s less pliable. Metal buckles look awesome and are generally more durable than plastic, but they’re heavier and may pinch as the harness shifts. If you happen to live somewhere with a nice adult toy shop, go browse; if not, check out a quality online retailer such as Babeland. Lots of leatherworkers will also take commissions, if you can’t find exactly what you want. Try talking to sellers on Etsy.

2. You and your boyfriend should pick out a toy together. You definitely want silicone, because it’s flexible and durable and can be sterilized. If you like a lot of clitoral stimulation, get a dildo that holds a bullet vibe in the base; if vaginal penetration is usually enough to do it for you, try a double-ender. As for size, choose something modest to begin with–if your dude is really gung-ho about this, his enthusiasm may write a check his ass won’t be able to cash without violating my rule. If and when you want to upgrade, a quality harness should be able to accommodate several sizes (usually by swapping out an o-ring, which you can buy at a hardware store if your harness didn’t come with extras).

3. Get good lube. For a silicone strap-on, you want to get a viscous, slow-drying, water-based lubricant like Liquid Silk (I swear by that stuff). If you’re feeling really luxurious, you could grab some silicone lube as well for when it’s your turn to catch. Make absolutely sure that neither of you is allergic to any lubricant you plan on using.

Trim your nails. You may also want to pick up some nitrile or latex gloves if you don’t already have some, so that you won’t be cockblocked by a papercut. Even if you’re monogamous and don’t generally use condoms, for anal your boyfriend might want to wrap it up. You probably want to protect your sheets/couch/backseat/kitchen table with a rag towel, too.

Once you have all the equipment, pretty much all you have to do is follow the rule. Limber up before you get started if you’re planning on an unusual (for you, that is) position; glove up, lube up, and go slowly. If you’re not accustomed to anal play at all, it might start out uncomfortable, and that’s normal. If the discomfort becomes pain, take a step back and add more lube before starting again. As with a lot of sexytimes activities, if you listen to your bodies and communicate with each other it’s pretty hard to go wrong.

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Featured image from Led Zeppelin, In Through the Out Door, 1979.

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Rachel

Rachel

Rachel is a queer lady from Texas who currently resides in southeastern Wisconsin. She studied history at Texas A&M University and has spent more time than she cares to admit arguing social justice with junior Republicans. She volunteers with Planned Parenthood and enjoys knitting, media criticism, and comic book slash fiction.

4 Comments

  1. February 12, 2012 at 11:47 am —

    Not specifically an anal sex concern, but I’d add to your point 3 that if you’re using silicone lube with a silicone toy, you really should use a condom on the toy to keep the lube from coming into contact with it. Silicone toys are expensive, and using silicone lube with them will ruin their surface!

  2. February 12, 2012 at 12:51 pm —

    “his enthusiasm may write a check his ass won’t be able to cash”

    *giggle*

  3. February 13, 2012 at 11:50 pm —

    Just wanted to add to this as a huge fan of pegging. You alluded to it, but it’s something that should be very clear.

    You want to do a lot of foreplay. This is more than “go slow.” Start with smaller things like fingers or small plugs and work up to the strap on. Your boy should feel full but comfortable as the steps progress. Especially for new people, this will take time, but can be a lot of fun. It also gets easier as you do it more, but lots of foreplay goes right up there with lots of lube.

  4. February 20, 2012 at 1:48 pm —

    I’d like to add that you need to think about it this way: it’s the bottom who does the fucking. It sounds weird, but it’s really true. He need to take you in–you don’t really push. You’re there and he leads you in.

    Also to cut down on the Santorum, he can try douching earlier in the day. Don’t eat anything heavy or super sugary beforehand. He can get himself all clean and it shouldn’t be too messy. Of course, with anal you have to expect that a little poo might happen–don’t panic, and be a “gentleman” about it. Just clean up and continue.

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