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.