Mar 081999
 

I have just started working as a professional dominatrix, and some of my clients (men) want me to fuck them in the ass with a strap-on. Any advice for a novice in that area?

–Mistress Scarlett, Minneapolis, MN

I am so glad you brought this subject up! I just went to a play party at a small dungeon, and watched an amazing anal scene. A tall, gorgeous dom with fiery red hair and thigh-high PVC boots had her sub on his knees sucking her strap-on cock with his hands tied behind his back. He was a little wisp of a thing, but boy could he fit that big cock in his mouth. After he serviced her, she put him on a bondage table on his back, and basically tied his knees to his chest with some beautiful rope work (red, of course). When she snapped on a latex glove, you could see his eyes get big and glassy. She started working her fingers in his ass, and he squirmed and moaned, but couldn’t go anywhere. She came to the edge of the table and started teasing him with her greased-up cock. He went nuts. Finally, she gave it to him, all eight inches, and he was in heaven.

Now for my advice:

There are so many men out there who enjoy having their assholes stimulated, played with, licked, and penetrated. And, according to lots of men I’ve talked to who are into power play, they especially love to be anally penetrated as part of being dominated, disciplined, even punished or humiliated. In addition to all the nerve endings in the anal area, men have a pleasure spot that’s just too good to overlook — the prostate gland. You can stimulate the prostate with your finger or a dildo.

First, you want to choose a harness that fits you well — the snugger and more secure the better; there are many different kinds (usually made of nylon or leather), and you should definitely try them on in a sex toy store if possible to see which works best for you. For beginning anal players, I would recommend a smaller dildo to start out, but of course, you should find what works best for you and your clients.

As the one doing the penetration, you should also experiment with different positions. I know that the first few times I fucked someone in the ass with a strap-on, I had the person in traditional doggie-style position for several reasons: 1) doggie style gives you a clear view of the butthole, so you can see what the hell you’re doing 2) the position allows for a good angle of penetration, towards the prostate in men (and towards the G-spot in women); and 3) it’s an easy angle to get your balance, establish a rhythm, and get some good thrusting going. So, you may want to start out that way, but you can also try missionary (usually with legs over the shoulders) or man-on-top. Although, as a dominant, I would say that putting him in a position with his ass in the air and head down is probably the best way to go, both practically and for its obvious submissive possibilities.

Anal penetration requires patience, practice and lube, lots of lube. Make sure your bottom is warmed up with lots of teasing. When you start out, you want to go slow and let the butt get used to having something inside it. Always work your way up, adding more lube as you go. When he’s finally read for that big silicone dick, be gentle at first; the more you go easy in the beginning, the more his ass will open up and trust you later on when you really want to ram the guy!

For more on this subject, definitely check out the fabulous video series: Bend Over Boyfriend (Fatale Video) and Bend Over Boyfriend 2: Less Talkin’, More Rockin’ (S.I.R. Productions). There is also a good book called The Strap On Book (Greenery Press) and another called The Ultimate Guide to Dildo and Harness Sex (Cleis Press).

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