Personal-Ad Adventure

No sooner had I penned my column on threesomes than I received an e-mail whose subject line read, "Rachel, will you answer our Craigslist ad?" Normally, I would delete such a message, figuring it for spam or some cheesy come-on. But I open it, and find a woman who identifies as bi, asking if I'd be interested in sex with her as an exhibitionist thrill for her boyfriend's 30th birthday. Whether it's that her name sounds familiar, because I've been feeling dejected and unwanted, or just a simple hunch, I entertain the notion. I ask her to send photos. When I see one of her on a Mermaid Parade float looking hot and tattooed, I agree to meet with Angie.

Within five minutes of sitting down to brunch with her at Public, I know my hunch was correct. We have a fabulous meal, and it's not because Maggie Gyllenhaal is sitting a few feet away. Angie's a far cry from what one might expect from such a stereotypical request. She's just gotten out of a nine-year, live-in, monogamous relationship with a woman; is gorgeous, smart, and funny; and is connected to the dyke community. We talk about everything from careers to Augusten Burroughs, and it isn't until we're getting up that we get down to specifics about the date.

She pulls out a reporter's notebook, jotting down my various turn-ons. We're oddly in sync, and when I ask if it might be OK if I fool around with her boyfriend, her eyes light up. In one of our subsequent e-mails, she asks if I like having my hair pulled. Little does she know I once wrote a story entitled "The Real Reason I Have Long Hair." It's been a while since I bottomed to anyone—since I let that side of my sexual persona take over, or rather, surrender. A huge part of my arousal process involves taking cues from the other person, so the fact that she wants to tease and beat me makes me want to do it even more.

As it turns out, on the night of our appointed date, Angie is violently ill. We both wonder whether this is a cosmic sign, but agree to reschedule. In the meantime, she tells her boyfriend, Dean, who is touched by her gesture and extremely interested. We agree to meet for an overnight visit at their upstate home. Some of my excitement for the encounter dies down in the ensuing weeks, but as the big night approaches, it returns with a vengeance. She picks me up at the train looking even hotter than I'd remembered. We have dinner and talk animatedly, then go home only to nervously stare at each other, talking but not touching.

Upcoming Events

Dean joins us and we continue to sit around. Finally, I take off my glasses, my horniness signal. She pounces on me, and in minutes we're kissing and licking and biting. She gets the upper hand. I wind up on their bed, bent over on my stomach as she slips off my favorite skirt to reveal a lacy red thong. Angie fondles my ass, admiring it. "I want you to take Dean's birthday spankings. I think I'll start with my hand," she says, almost to herself, and then lets loose with a series of wallops.

She makes me count. "One," I squeak out, adjusting to the sweet pain.

"Backward," she clarifies, and I find myself having more than a little trouble absorbing her increasingly harsh blows while counting down from 30. I wind up skipping 16, and we have to start over, and by then she's taken out a large, solid, metal-reinforced paddle. She strikes mostly on the outer edges of my ass, rather than the center, and it hurts and feels good all at once. She teases me by pulling at the thong and stroking her fingers over my wetness, then returning to the task at hand.

After I successfully get to "one," I'm filled with pride as well as arousal. She soothes my hot skin with ice, letting the cubes melt down my legs before sliding the remnants inside my pussy. She rakes her nails along my skin, biting me on the back of my neck, marking me anywhere she can. It's been so long since I've submitted sexually like this to anyone, offering myself up to them to do as they wish, but partly because she's so clearly at home in the top role, bottoming to her feels totally right. Dean looks on with fascination, and then they both start to attack me. I feel hands and lips everywhere, and when she spanks my pussy, the act brings tears of pleasure to my eyes.

The most porno moment comes not when we both suck his cock, or when I watch them fucking while he goes down on me, or even while he looks on as she slams her fingers inside me. Those all feel, oddly enough, perfectly natural; a little wild and crazy, but hot and comforting too. The cliché arrives when, as Angie's undressing me, she asks if I'll do them a favor. I'm expecting some wild sex request, but instead, I'm asked to put my glasses back on to indulge Dean's spectacles fetish. I giggle as I do, because we look like two sexy schoolteachers getting it on. We tumble together in various sexual permutations for a few hours, then snuggle under the covers. As I'm drifting off to sleep, he slides on top of her and they begin a round of frantic fucking. I'm so tired, it's all I can do to watch them go at it.

I couldn't have predicted a more perfect personal-ad encounter. What I loved best was not her ability to read my submissive tendencies like a book, knowing just how to bite my back and order me around, nor even that she was so stunningly gorgeous I'd stare longingly, marveling at her amazing body, nor the ejaculatory orgasm she coaxed from me. What made this night so special were the glimpses of raw, honest emotion, the ones that make sex worth it for me: pouring out my heart to her about my not-so-secret crush, Dean telling me he's nervous even as I'm going down on him, all of us laughing when I bungle the countdown. I got all of that, along with a chance to do their dishes (a fetish of mine), mind-blowing orgasms, and a night of feeling utterly beautiful, wanted, and wanton. As Metro-North whisked me back to Manhattan, I congratulated myself on trusting my instincts. I'm so glad I didn't hit the Delete key.

Please visit

Sponsor Content


All-access pass to the top stories, events and offers around town.

  • Top Stories


All-access pass to top stories, events and offers around town.

Sign Up >

No Thanks!

Remind Me Later >