I want…double penetration

To you, double penetration (affectionately known as DP) may seem like a porno circus trick. But the idea of getting filled up and stretched out has always appealed to me, and since group sex has moved from fantasy to common practice for me, I’m hungry for a new challenge.

Before starting, I talked to a longtime friend and dirty-adventure coconspirator with some personal experience. Jefferson, something of a New York playboy who records his exploits on his blog, One Life, Take Two, was the perfect go-to dude to help out with the mechanics. “My advice on position,” he advised, “is to regard one cock as the anchor, with its possessor reclining under the woman, with the second cock entering her from the rear.”

Worrying about keeping one flesh-and-blood dick happy and excited seemed tricky enough, so I arranged to borrow Jefferson’s girlfriend, Madeline (who also has a sex blog, MadelineintheMirror), and combine her with my boyfriend, Bobby D. And so on a sunny Sunday afternoon, while other East Village denizens were still waiting for tables at 7A, I was getting my nether orifices filled up by my boyfriend and a strap-on.

We started with a good old-fashioned threesome—a two-girl blow job, one girl on cock and the other riding my boyfriend’s face—before we got more advanced. I encouraged them to tongue-fuck my “naughty hole” (as Bobby D affectionately calls the anus), and after I had a sheet-soaking orgasm, we decided that Bobby D should enter me anally, on the principle that my vagina would be more stretchable once I was half full (an optimist’s DP!).

Though we were prepared to do the standard anchor position with Madeline on her back on the bottom, me in the middle and Bobby D fucking my ass from behind, we somehow worked ourselves into a weird position (Madeline joked: “Right foot green!”). With me on my side, they went at me piston style, resulting in three heavy orgasms for me, a squirting one for Madeline and an anal cream pie (a.k.a. come in my anus) from Bobby D.

Afterward, I lay in my sticky, postcoital trance for a while and then realized that I was totally famished. Over a sushi dinner, Bobby D and I reminisced while Madeline, having returned to Jefferson, sent me naughty text messages. We may have a date next month.

Jamie says:

When choosing a third party, you have a major decision to make: Should they be a friend, a stranger or someone in between (e.g., your local Starbucks barista)? I’d recommend the in-between person. Friend: too dangerous relationshipwise. Complete stranger: too dangerous in other ways. In-between person: They know you know where they work, so they’ll be on their best behavior. Of course, if things get awkward, you will have to find a new coffee place.