Archive for April 6th, 2009

Well, this weekend was a blast – I’ll certainly be writing about it later, and posting links here when the videos go up. Suffice it to say for now that I worked hard and I’m still not fully recovered, but I think we got some great material.

But now, to your questions! This week, I’ll be answering only one: it’s a big question about which I could go on at novel-length, but instead I’ll try and keep it around a thousand words.

Dear Delilah,

My partner and I have recently started experimenting with some new flavors of kink. Among these, we’re playing around with me fucking him in the ass with my silicone cock. This is something we both want to do, a lot. But we have a hard time talking about it, and also a hard time doing it in a way that won’t hurt my sweetie. I’d like to get better at both breaking out the toys and segueing into this kind of scene, and at being a gentle, competent top in the scene. Any suggestions?

Aroused, Sensitive, Sweet – Frustrated, Underprepared, Cautious, Kinkster

First of all, ASSFUCK, you win for the best acronymic nom-de-plume yet. So right there you’re ahead.

But your question, right! For those of you playing along at home, our gentle reader is referring to “pegging,” a term coined in a Dan Savage column in 2001. A pretty good wiki article about it is here. Specifically, pegging refers to the act of a woman fucking a man in the ass with a strap-on. It may be done in a sweet, loving way or in a brutal way, in a dominant/submissive context or not. And it has a lot of baggage attached to it: heterosexual men often associate being fucked in the ass with being gay. So it’s little wonder that it’s difficult to talk about. In my experience, even men who really love it either find it hard to talk about wanting it, or feel the need to couch it in a “sissifying” context, where their desire to be penetrated is a ritualized removal of their manhood.

In your case, though, it sounds like you both know that you want it, and so perhaps the more difficult project is not talking about it but getting the party started. You used the word “top” in your letter, and I’m not sure whether you mean it just as in you being the “active,” penetrative partner, or in a D/s kind of context. Either way, though, one of the difficult things for some women is that you are probably the one who needs to initiate this kind of scene – and this can be difficult, as women are not socialized to initiate sex. What with this type of act being such a delicate subject for many, it’s even more difficult. You need to accept that you might bring it up at the wrong time, when he’s not in the mood for it or ready to try it. But it’s still likely that you do have to bring it up, and you may have to do it more than once.

I do have some suggestions, and would be happy to share. First, there are the ways to work up to the actual pegging part. Then, there’s how to initiate a scene.

If you’re worried about hurting your partner – and it’s good that you are – then you should work up to the actual silicone cock part. Besides the fear and pain that can accompany anal penetration, there’s the problem that your cock is, well, synthetic, and it doesn’t have nerve endings that connect to you and help you know what’s going on with your partner. Start with fingers. Or rather, start with one finger. Slip on a latex (or polyurethane, if he or you are allergic) glove, get plenty of lube, and gently work it around just the outside of the anus to start. Little by little, you should be able to work it in, though there’s no need to rush. Words of encouragement are good here. Eye contact is great, too. I recommend starting with him lying on his back, knees up. You’ll feel when the sphincters relax and allow you to move in a little more.

When you’ve comfortably got a finger inside (which may take more than one session!), try a small toy. This could be a wearable toy, but it should be narrow, and you should start by holding it in your hand. You’re probably a lot better at using your hands to feel your way places than you are at using your pelvis. Lube the toy well, and ease it in with the same care you used with your hands. Make sure at all stages that you give him the option to make it stop or slow down.

When you’ve done this a few times with good success, and are at a stage where you can move the toy in and out and have that be a good thing, you’re ready to strap on. I’ve found that a great way to work with a strap-on cock is to have whomever I’m planning on fucking suck my cock first. The visual component of that, plus the receptive partner’s acknowledging of the cock as a cock and not an inert piece of silicone, helps me connect with the toy and feel it as more a part of me. Once you feel “plugged in” to the cock, find a comfortable position (again, I recommend having him on his back at first), and guide yourself in. Don’t move at first; just give him a chance to relax and adjust to the feeling of fullness. After enough practice, you should be able to go to town. And remember: there is no such thing as too much lube.

You might also try working with a buttplug, especially if you do want to add a D/s component. Once you’ve reached the point where you can comfortably get a finger inside him, having him wear a buttplug for a while before he comes to see you can be a great way to get him both revved up and relaxed for further action. (Incidentally, my favorite source for these types of toys is Blowfish.)

Now the second part of this is: how to initiate all of this? Well the good news is, if you start with just a finger, all it takes is grabbing a glove from the bedside table, dousing it with lube, and beginning. If the project progresses well over several dates, then eventually the rigamarole of strapping on won’t seem quite so difficult to transition into.

What I recommend is this: when you’re planning on going from fingers to toys, have the toy on the bedside table, out and ready, before you start playing around. Giving the toys that you’re going to use a presence in the room is a simple way of raising the subject.

When you get to the part where you’re going to strap on for the first time, have everything you need laid out on the bed. Lee Harrington once wrote brilliantly about strap-on sex being a very deliberate act of love, more intimate than almost any other kind of sex or play. Playing up the deliberateness, rather than trying to escape its inherent awkwardness and interruption of action, ritualizes the experience and adds to its sexiness.

There is much, much more information available about this, in books like Anal Pleasure and Health and countless other titles: if you’re a bookish sort, do your research beforehand and enjoy!

Also, I’m a horrible voyeur, so please do write back and let me know how it goes!

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