Chronicles of a Libertine: The Art of Double Penetration

by Emmanuelle Undine on July 1, 2010

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Here’s one sex act you didn’t see on Team America: double penetration (dp). A now integral part of two-guys-and-a-girl threesomes and free for all gang-bang scenes, double penetration has saturated mainstream porn. Before you try dp at home though, heed my warning. Contrary to the ease with which guys position themselves and slide their cocks into a female performer’s orifices in your favorite films, in real life dp is nothing short of an acrobatic feat.

My fascination with a particular subcategory of dp – ass/pussy double penetration (or “apdp” for short) – started long before I became exposed to the practice online. In my previous post I elaborated on my recurring dream of being ravished by a tentacled leviathan. Examined in the clear light of day, this story helped me realize that a part of me was driven by a primal, submissive yearning to be completely filled in a way that far exceeded what any one man can accomplish alone. French philosopher and hardcore fiction pornographer Georges Bataille would equate my dream to an expression of my desire – the desire of a discontinuous, individual being – to experience a sense of profound continuity. Furthermore, he would likely argue that my dream lays bare the notion that what is at stake in any form of eroticism, be it sexual, romantic, or spiritual, is the dissolution of constituted forms (bodies, identities).

The enlightened context of Bataille’s take on sexuality not only fascinated me as a result of its associations with Tantric sex, but also gave me license to explore my tentacle porn dream and experiment with apdp. Contrary to the woman who posted an online video clip of herself shitting an octopus, however, my research didn’t involve a necrophilic act of bestiality. Instead, I attempted to adapt my fantasy to real-life, multiple penetration scenarios involving inanimate objects and, eventually, consenting adults.

At first, before I worked up the courage to ask two men to fuck me in tandem, I played with toys. With one dildo in my ass and another in my pussy, I masturbated in countless different positions until I finally figured out my preferred double penetration angle. Even if you never graduate to practicing apdp with men, it is well worth a try with props. The seismic orgasms you’ll experience on account of having your sphincter, G-spot, and clit stimulated at the same time are mind-blowing.

As soon as you raise the stakes by trading toys for hard cocks, however, apdp transcends the private sphere of closet masturbation and becomes a collaborative art form. As with any art, success requires practice, skill, and commitment. Beyond the physical challenges involved in apdp, to enjoy a mutually satisfying session you should be aware of two pitfalls before getting started: performance anxiety and over-stimulation.

Keep in mind that although the idea of an apdp threesome may appeal to most men, in actual practice it is not uncommon for them to feel overwhelmed – at least the first time around. For one thing, the membrane separating your vagina from your rectum is thin, and some guys may be shy about crossing swords or feeling another cock in such close proximity. Likewise, some straight guys find it challenging to maintain an erection in front of other men. In my experience, creating an open, accepting, and non-competitive atmosphere that fosters communication and exploration helps all participants to overcome their respective fears.

Over-stimulation, on the other hand, causing guys to get off too soon and the woman to forgo orgasm altogether, requires the same amount of patience to work through. While premature ejaculation may be embarrassing for guys, repeated apdp practice quickly desensitizes them. The situation is not as simple for the woman. In my case, achieving orgasm requires concentration and the ability to let myself go – two things I can easily do during an intimate, one-on-one session with my lover, but have been unable to manage in a threesome. Yet. Nonetheless, I’m confident that in time I will overcome my mental block and be able to experience the full force of a double penetration orgasm. What makes me so certain? I know one thing for sure about apdp. As with any art, repeating the process will eventually give rise to something beautiful.

Read all of Emmanuelle’s sordid sex stories.

  • Tony Stark

    Is this pic of you as well? Love your articles by the way. Would you like to be my assistant? I think Pepper is due for a raise. Let me know.

    Tony “Ironman” Stark

    • emmanuelle undine

      Hi Tony,

      I’m thrilled to hear that you enjoy my posts! Thank you for taking the time to write in — it means a lot to me to hear from my readers. Unfortunately this is not a picture of me (I get too caught up in the action during sex to remember to snap pictures!). As for my replacing your dear Miss Potts, I’m not sure if I’d make an adequate assistant. My magnetic charms are limited to seducing men and bringing them to orgasm. Levitation and disintegrating bullets are far beyond my skill. :)

  • Tony Stark

    Is this pic of you as well? Love your articles by the way. Would you like to be my assistant? I think Pepper is due for a raise. Let me know.

    Tony “Ironman” Stark

    • emmanuelle undine

      Hi Tony,

      I’m thrilled to hear that you enjoy my posts! Thank you for taking the time to write in — it means a lot to me to hear from my readers. Unfortunately this is not a picture of me (I get too caught up in the action during sex to remember to snap pictures!). As for my replacing your dear Miss Potts, I’m not sure if I’d make an adequate assistant. My magnetic charms are limited to seducing men and bringing them to orgasm. Levitation and disintegrating bullets are far beyond my skill. :)

  • douglas

    Emma,
    Well, as always, your writing is as exciting as ever and I must say, well thought out. I’ve had the pleasure of two girls, but as you’ve indicated, was too anxious to do the two guys and a girl threesome, although the opportunity has presented itself a couple of times over the years. Perhaps if I ran into someone who was as thoughtful and nurturing as your are about the whole “process,” it might not be so bad. Still, I don’t know if I can get over the whole mental block when it comes to crossing swords – definitely would kill the moment. Maybe you would have better luck in your individual quest for ecstasy if you tried DP with two transsexuals (pre-op). Just putting it out there…

    • emmanuelle undine

      Douglas,

      Thank you for your continued supportive and candid feedback. I’m really glad to count you among my readers! I understand your hesitation about a two-guys-and-a-girl threesome, but with the right people and under the right circumstances it can be a lot of fun.

      As for transsexuals, I’ve been very curious about them for some time now, particularly pre-op trans with penises but who identify as and look like women. (As always, my interest was roused by a book: French philosopher Michel Foucault’s _Herculine Barbin: Being the Recently Discovered Memoirs of a Nineteenth-Century French Hermaphrodite_.) I have often wondered about how transsexuals relate to gender, how they experience sexuality, etc. In terms of my own fantasies, I sometimes wonder what it would be like to have sex with a woman who has a penis….

  • douglas

    Emma,
    Well, as always, your writing is as exciting as ever and I must say, well thought out. I’ve had the pleasure of two girls, but as you’ve indicated, was too anxious to do the two guys and a girl threesome, although the opportunity has presented itself a couple of times over the years. Perhaps if I ran into someone who was as thoughtful and nurturing as your are about the whole “process,” it might not be so bad. Still, I don’t know if I can get over the whole mental block when it comes to crossing swords – definitely would kill the moment. Maybe you would have better luck in your individual quest for ecstasy if you tried DP with two transsexuals (pre-op). Just putting it out there…

    • emmanuelle undine

      Douglas,

      Thank you for your continued supportive and candid feedback. I’m really glad to count you among my readers! I understand your hesitation about a two-guys-and-a-girl threesome, but with the right people and under the right circumstances it can be a lot of fun.

      As for transsexuals, I’ve been very curious about them for some time now, particularly pre-op trans with penises but who identify as and look like women. (As always, my interest was roused by a book: French philosopher Michel Foucault’s _Herculine Barbin: Being the Recently Discovered Memoirs of a Nineteenth-Century French Hermaphrodite_.) I have often wondered about how transsexuals relate to gender, how they experience sexuality, etc. In terms of my own fantasies, I sometimes wonder what it would be like to have sex with a woman who has a penis….

  • small1sh

    APDP is something I’ve been wanting to try for years. However like you wrote I’m concerned about maintaining an erection with another guy present. Also finding a willing female partner to participate, then another male has been difficult.

    • Emmanuelle Undine

      Hi small1sh,

      Have you tried looking for willing participants online? Also, you could look into visiting a local sex club on one of the nights when they permit entrance to single men: Often couples look for a third party with whom they can play…. Good luck in your quest for dp! (about maintaining an erection in the presence of another man: From what straight men who practice dp have told me, you can condition your mind to do that. It takes time though….)

  • small1sh

    APDP is something I’ve been wanting to try for years. However like you wrote I’m concerned about maintaining an erection with another guy present. Also finding a willing female partner to participate, then another male has been difficult.

    • Emmanuelle Undine

      Hi small1sh,

      Have you tried looking for willing participants online? Also, you could look into visiting a local sex club on one of the nights when they permit entrance to single men: Often couples look for a third party with whom they can play…. Good luck in your quest for dp! (about maintaining an erection in the presence of another man: From what straight men who practice dp have told me, you can condition your mind to do that. It takes time though….)

  • Txl752

    I love DP
    You are right about new guys to DP. I find that by the 3rd 3some with new guys they last longer and are more into fucking me and loosen up. It also helps if my husband let’s us have some alone time first.

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