My partner and I have been gently exploring together. He’s had experience with BDSM and, although I’m new to it, I am really into it. We’ve been reading erotica and doing some role-playing and are working up gradually to more exploration and making sure there is consistent trust on the way.

One thing we’re both really interested in doing that we’ve never done before is having me penetrate him with a strap-on. We have one, of modest size, and we’re both excited to try it but uncertain how to proceed. Can you give us some suggestions for preparation so that the experience can be relatively clean and not too painful for him?
HEADING FOR A LAND DOWN UNDER

Some people will do an enema before anal sex to make sure they don’t run across any stray plop. I find it unnecessary, but I had enemas as a child in conjunction with health issues and hospital visits so I have unhappy associations with them. I don’t love it when someone pulls a dildo out of my ass that has shit on the end of it but you do get used to it; just throw it in the sink with some hot water and soap and return to the scene. Also, if someone’s got something in my butt it’s because we’re friends and friends don’t judge friends for having a digestive system. Shit doesn’t always make an appearance but as I’ve said before, the ass is where it lives (though not specifically in the area you’re exploring, that’s just its front door, so to speak) so it’s kind of like going to, say, France and expecting not to run into any French people.

What you might want to do is start with fingers and work your way up to the dildo. Lubricant is the guiding tool of anal sex and I find silicone lube the most long-lasting and slippery, though you are often warned not to use it with silicone toys. Speaking of which, one of my favourite anal toys is called the Raspberry Kiss. It’s shaped like a bent finger and the small insertable provides a deliciously deep vibrating option. And check out Come As You Are’s web page on anal sex at www.tinyurl.com/2h5mra. Their five basic suggestions are really helpful.

All tied up inside
I’m in a relationship with a girl who is the best thing that ever happened to me. The thing is, I can’t get fully erect with her only because of a different relationship a few years ago. This other girl was very submissive and loved to deep throat among other things. And, if you haven’t guessed, my new girlfriend can’t do those or chooses not to. So my question is: what measures can I take to help me get over this comparison or help her get more open to things?
MR. IMPASS

I believe the greatest fear we have when we express our sexual desires is that someone will shut us down and by virtue make us feel intolerably vulnerable. But if you are able to see your desires as valid and natural, you’ll recognize that they deserve to be verbalized. How about saying to your new girlfriend, “I’m sure you’ve noticed my dink’s been a bit floppy. I’m really into being dominant and that’s informed the way I get excited. Would you be interested in trying a few consensual S/M scenes? I really dig you and I’d hate to lose you because I’m having trouble expressing what I want. And while we’re on the topic, is there anything different you’d like to try?”  

LOVE BITS
Last week, in response to a letter from a fellow with Asperger’s taking “tentative gestures” towards his sexuality, I asked pros and clients to share their thoughts about the value of gaining erotic experience with a sex worker. “G” wrote, “I was a virgin who had not been in anything resembling a relationship at age 24, when at the encouragement of some close friends I bit the bullet and saw a service provider. While this was a positive experience, Aspie’s statement rings very true to me. This was three years ago and while it helped take away the mystery and the fear that I would never get laid, it hasn’t changed my inability to relate to women in a non-professional environment, and I definitely don’t feel any more prepared to relate sexually to a partner than before.”

Amanda Brooks writes: “I’ve seen virgins before. It’s a little awkward, but my goal was to make them comfortable and give them some confidence. Getting that first experience is important, especially so late in life. [He should] do his research to find a reputable woman who seems kind and intelligent. Chances are he’s not her first. He may not ‘learn’ anything, but then, whose first experiences were teaching labs anyway? Learning comes with many partners, not the first. A good pro will give him pleasure, relaxation and no emotional problems. Then he can go forth and conquer.”

A counsellor for children with Asperger’s commented, “I would imagine the thing that makes it difficult for this person is that sex seems to be all about communication, precisely the element of social functioning that those with Asperger’s are lacking.” She recommended Aspie contact the Geneva Center for Autism (www.autism.net), if he hasn’t already, as they have programs for adults.

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