Dear Sasha, 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 gradually working towards more exploration and making sure there’s consistent trust on the way.
One thing we’re both interested in doing 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
Dear Heading,
Some people will do an enema before anal to make sure they don’t run across any stray plop. As for me, 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 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. Fingers will give you a good sense of how the area responds to touch and what it all feels like inside. Lubricant is the guiding light 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 http://tinyurl.com/2h5mra. Their five basic suggestions are really helpful along with the toys, books and videos they recommend.
Dear Sasha, 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 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
Dear Impass,
One of the top reasons people get involved in intimate relationships is to have some sex. If this fact fills you with silent anxiety, you should expect this is going to affect your sex life in precisely the way you describe. Imagine for a moment if we applied the same tacit approach to getting what we want out of other things that are as vital to us. It simply doesn’t make sense.
I believe the greatest fear we have when we express our desires is that someone will shut us down and by virtue make us feel unbearably 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 SM 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?”
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