Tristan Taormino is the author of several sensationally sexy and informative books including Down and Dirty Sex Secrets, Pucker Up: A Hands-on Guide to Ecstatic Sex, The Ultimate Guide to Anal Sex for Women. From college campuses to sex toy boutiques she tours the country touting the wonders of anal sex and the overall goodness of sex in all its frisky forms. In the Anal advisor columns, first published in the Village Voice, Tristan addresses the ifs, ands, and butts of anal sex.

You can visit Tristan at her official website, www.PuckerUp.com.
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Dear Anal Advisor:

My boyfriend and I want to have a three-way experience–he and his best friend (a guy) and me. It has always been a fantasy of mine and he too wants to go through with it. We both swing, so we don’t mind seeing each other with another person. I have never really done this before. I have sucked another guy off while my boyfriend fucked me. However, I have never had two guys penetrate me at the same time, but I really want to do this. I think the idea of having two cocks in me–one in my pussy and one in my ass–would be an unbelievable feeling. However, this seems to be a hard thing to pull off. Do you have any tips on how to make this experience as pleasurable as possible?

Thanks in advance,
Fingercuffs

Dear Fingercuffs:

Congrats for being able to voice your fantasy out loud and tell your boyfriend. Fantasies can be incredible forces in our lives. When you share a fantasy with your partner, it can bring you closer together–and you can have a hot time in the process! My first piece of advice is that maybe the two of you should practice some double penetration before you invite your friend over. Use a flexible vibrator or dildo in one of your holes and your boyfriend fills the other. Use lots and lots of lube, go slow, and work your way up to it. Communication is extremely important: you’re testing the limits of your body, so make sure you give your man plenty of feedback about how it feels. Also realize that some women can easily and comfortably accommodate something of size in their pussy and in their ass. Others will take some effort, with lots of warm-up. But some women may not be able to do it at all, since double penetration really depends on your internal map, and if there’s room for two. You are the one who will know best if it’s possible, so make sure you’re the one who’s in charge and calling the shots. Work out the kinks on your dildo before you plan your threesome. When you are ready to tackle two flesh cocks at once, use plenty of lube and go really slow. Depending on the size and height of all three of you, some positions will work better than others. You may want to straddle one man and have the other nail you from behind. Try to take one cock about halfway inside your pussy, then angle your body to take the other one in your ass. Both men should start with shallow penetration, so you can get used to the feeling. Remember that porn stars make it look easy in adult movies, but they are seasoned professionals! You may be much more awkward your first time around. Practice makes perfect.

Dear Anal Advisor:

What are your thoughts on what has become a new trend in adult films: the ass to mouth act? Have you indulged in this act, and how would you suggest one prepare for such a nasty maneuver? I would appreciate any advice you can give me.

Jacey

Dear Jacey:

Taking your dick out of a woman’s ass and directly shoving it into her mouth may make for exciting porn, but, in real life, it can be problematic. Bacteria lives in the butt that may not peacefully exist in the mouth, and could lead to an infection. No matter how squeaky clean her rectum may be, chances are there are at least trace amounts of fecal matter which may end up on your dick–do you really want to make her suck that off? Would you put it in your own mouth? I have a better idea. Fuck her in the ass til she’s right on the edge of orgasm, or you are. Order her to get on her knees and close her eyes. Talk to her, tell her she better open up her mouth for your cock. Have an anti-bacterial baby wipe stashed nearby, and quietly grab it, slide it over your cock, then toss it. Now proceed with sticking your rod in her mouth, keeping the fantasy intact, but keeping it clean for everyone involved.


Dear Anal Advisor:

I love it when my wife wears a strap-on and gives it to me in the butt. My problem is that she only does it occasionally. I wish she would do it more and enjoy it more, but I think maybe it's not to be. I've even thought about having a gay encounter so I can get fucked in the ass more. Any suggestions? Are there any women that like screwing guys?

Signed,
R.H.

Dear R.H.:

Are there any women that like screwing guys? R.H., is the sky blue? Do I love getting fucked in the ass? Yes, yes, of course there are women who enjoy turning the tables and being on the other end of a nice butt fucking for a change. Unfortunately, your wife may not be one of these dildo-wielding divas. Since you've already gotten your ass plowed by her before, I think it's fair to ask her directly why you're not getting the backdoor gift from her more often. Have you told her how much it turns you on? Your wife may have some issues with being the penetrator (instead of the penetrated), since it is not a straight woman's typical role; however, you can reassure her that there are plenty of other women giving it to their guys and loving every minute of it. Perhaps she hasn't realized her own potential for pleasure during strap-on sex. In addition to being a real turn-on upstairs (in her head), there are also plenty of ways for her to get off while she's got her cock in your ass. For some women, when the base of the dildo rubs against the clitoris and vagina, there is enough friction there to feel fantastic. Your gal should also consider the power of having balls. Some women simply don't choose a dildo with balls because they prefer a more non-realistic style dildo; however, balls do more than make it look real, they extend the base of the dildo and cover more surface area–which means more for you to rub up against. Think about it. If she wants to add a vibrator to the equation, she has several options. She could select a vibrating dildo, which will deliver vibration to both of you. She could try to don a wearable vibrator beneath her harness, but this may be awkward and interfere with the harness being tight enough. A better idea is the "Buzz Me" harness made by Stormy Leather and equipped with a pocket for a small vibrating egg (http://www.stormyleather.com). Vixen Creations has several dildos, among them "Treasure Chest" and "Bobby Sue," with hollowed-out bases (http://www.vixencreations.com). Stick a vibrating egg in the base of the dildo, tuck the battery pack in the side of the harness and she's ready for vibrating action, his and hers style! For double penetration (one for you, one for her), there are harnesses with two holes, one for the dildo to penetrate you with, another for a dildo pointing in her direction. The "Nexus" by Vixen is not an extra long jelly dong like you see in adult novelty stores. Instead, it's a two dildos-in-one package: she can have a dildo inside her pussy or ass while simultaneously penetrating your ass. I just love sex toy technology! If you want to learn more about strap-on anal sex, I highly recommend the videos Bend Over Boyfriend 1 & 2. Now, as for your idea about having a "gay experience" in order to fulfill your anal sex desires, don't you think that switching teams might be a little too extreme? Unless you are actually bisexual, and looking for a way to express your desire for men, if it's anal sex you want, I stay stick with your wife and see if both of you can get what you want and need out of the assfucking experience.


Visit Tristan at PuckerUp.com.