He was a TV star. She was a writer. When their love life started adding friends and strangers, things took an odd turn. A true story.

Our first threesome is after the opera. I’ve been dating my boyfriend – let’s just call him John – for a few months. I have a toothbrush at his apartment but not a set of keys. John is getting rich; he’s in a popular TV show – in fact, I can barely open a magazine without seeing his face. What he’s doing with me is a little unclear. I’m about 10 years his junior and absolutely unfamous. But I work in the media, which I guess he finds intriguing, and we get along rather well. Although he says up front that he can’t – and won’t – commit, he’s funny and charming, and I’m 24 and up for anything. Which leads us back to the opera.

At the intermission of La Bohème, we drink champagne on the terrace overlooking the fountain at New York’s Lincoln Center. He asks me what I want to do afterward. “Well, we could hire a hooker,” I say, wanting to turn him on. We’ve been talking about it for weeks. I’d told him I wanted to be with a woman, and he in shock – said he’d always wanted to be with two. We’re really no different from anyone else. For men and women the threesome has evolved into the Mount Everest of sex – almost everyone I know wants to try it, and if they haven’t they want to know what it’s like. Is it sexy? Is it too… much? I’m interested also for strategic reasons. John keeps talking about how he can’t be monogamous, and I figure if we cheat on our relationship together it’s really not cheating. As for hiring a hooker, I had never thought I’d do that, but it would allow us to avoid creepy solicitations of our friends (of course, we’d move on to that later).

Not surprisingly, John is intrigued by my hooker suggestion. “Not a bad idea,” he says, grinning. And though I’m not sure I meant what I said, he’s now so excited it’s too late to turn back. After the opera we race to his apartment, where he starts hunting for escorts online as I scour the classifieds in his magazines. In the back of a city magazine I find an ad for “highclass” escorts. He calls and orders us a young blonde one with “lots of experience with women.” The price is $1,000 an hour. Yikes. The rent for the apartment I share with two friends is $1,000. John gives his credit card information and his real name to the person on the other end of the phone. I know what you’re thinking: He’s a well-known person – what the hell is he doing? But John doesn’t care. It’s as though he’s ordering take-out Chinese. The woman on the other end says something. John laughs, rolling his eyes at me. “I’m glad you’re a fan,” he tells the woman, who I guess is the escort service’s madam. “That’s very flattering. Thank you.” I wonder if the madam will sell the story to The National Enquirer. I keep that to myself. Now it’s time to get ready. We jump into the shower; it seems like the polite thing to do. I wish I had some lingerie. We don bathrobes. The shower has sobered us up, which is not necessarily a good thing. John rolls a joint with some dried-out pot. Then we start cleaning furiously. He’s making the bed, and I’m washing the dishes. “I feel like I’m expecting my in-laws,” John says. He opens a bottle of wine. He putsa Massive Attack CD in the stereo. It feels as if we’re staying at a fancy hotel. I dim the lights more.

The doorman calls up to announce our“visitor.” He must know – doormen know everything. There’s a knock on the door. I freeze, but John lets in a small blonde Russian woman. She’s maybe 21, and she seems a little innocent for a hooker. Her English is broken, she has small, real breasts, and I’m prettier. Perfect. I offer her a drink, and while I get it John gives her an imprint of his credit card. (That will fetch a nice price on eBay, I think.) We make our way to the bedroom, where John has thoughtfully, if a bit cheesily, arranged and lit candles.

And so here we go. It kind of goes down the way you’d think it might. John tells the hooker I’ve never been with a woman and asks her to kiss me. “I want to watch,”he says. You know, it’s amazing how you can think the dialogue in porno movies is stupid, but then you find yourself in a real-life-porno film, and you say the same dumbass things. I tell her to “go down on me.” I can’t believe I’ve said that, but down she goes. Then John shows me how to go down on her. For a guy who claims never to have done this before, he’s got the fantasy mapped out.

I wish I could tell you it’s the most amazing sexual experience ever. It isn’t. But it isn’t bad, either – it’s a little like a boozy sex-ed class or a horny slumber party. You have to pay attention to other people’s feelings, and you have to keep your ego in check. I watch John have sex with the hooker, and strangely I don’t feel jealous, just a little competitive. Then we give him a blow job. “I’ve never been this hard before,” he says. (See what I mean about the porno dialogue?) But – and here I lay down my first threesome rule – I don’t let him finish. “You two should make porn,” the hooker gushes. And then she gets up to leave. Charlie Sheen knew what he was talking about when he said he doesn’t pay a prostitute for sex but also to leave. I’ve heard the Metropolitan Opera and church bells at dawn, but the sweetest sound I’ve ever heard is the door slamming behind that hooker.

The next morning, John’s out of bed early – he’s appearing on a talk show. I watch it in bed and wonder if the Russian will figure out who he is and brag. When I get to my office the next morning the woman who sits next to me asks how the opera was. “Nice,” I say. It was nice. And we’re just getting started. Remember what they used to say about crack – that all it takes is one puff and you’re hopelessly addicted? John and I became that way about threesomes. The very next night we hire another hooker from the same place. The madam tells John she’s got a “good one” for us, as though she’s got a fresh batch of Atlantic cod. (Frighteningly, she also tells John he looked cute on TV this morning.) But the madam needs glasses. The young woman who arrives at the door has stretch marks and fake boobs the size of beach balls, and worst of all she keeps talking about her little girl. It’s horribly depressing. She gets John to use some strange sex toy – a pair of mini silver vibrators – on both of us simultaneously. It feels like a scary gynecological exam. We shuttle her out the door after half an hour. Later the woman on the phone tells us, “You can always send her away for a refund or an upgrade.” Great. But John and I decide to go for a nonhooker partner, a civilian: a civilian would be exciting, sexier and a hell of a lot cheaper.

And John has just the one – he confides to me that he recently got a blow job from a pretty European woman at a nightclub, and, he says, she likes women! “Let’s fuck her!” I say. I know how twisted that seems, but in the moment, John’s fortunate round of philandering feels like great luck for both of us. We have someone! We meet the European at another club a few nights later. She has short, silky blonde hair and a tight, trim body, and she doesn’t speak English all that well. She’s hotter than the hookers and has much better style, too. The threesome isn’t exactly proposed as much as it just occurs. John’s hands are all over us at the club. Then we’re out the door and riding in John’s town car and – hello! – the European and I are giving John a blow job together while she has her hands between my thighs. I think, do other people do these kinds of things? And do cars really have security cameras in the back?

We go back to John’s apartment, and when I walk out of the bathroom they’re already sprawled on the bed, which makes me feel insanely jealous – so I join them. Her stomach is flat, and I hate that. But she’s hot and makes me come quickly. Then I return the favor. It goes on for a while. Here’s the thing, though: Unlike with a hooker, I can’t ask the European to leave after an hour. Worse, John snuggles with both of us. I keep panicking that I’ve started something I can’t stop. But once a week for about two months, we keep doing it. It evolves into a strange relationship. The European starts sending me emails. I email back. On my birthday she sends me beauty products as a gift. A co-worker asks me who they’re from. “Um, a friend,” I say. She comes to my birthday party, and my friends ask about her. “A friend of John’s,” I say. I guess she is a friend, but I wish John hadn’t invited her. My birthday night ends at a strip club, just the three of us with a stripper in a private room. Not exactly Eloise at the Plaza, I know. The stripper and the European are hitting it off. John gives the stripper an extra gate card to the nearby hotel suite he has rented for us for the night. I think he’s nuts. Won’t she tell a gossip column? We all end up in a Jacuzzi in the hotel room. John’s assistant – whom he made sign a confidentiality agreement, thank God – has stocked the place with water, candles, condoms, champagne and (a nice touch) extra toothbrushes.

Everyone eventually gets it on. The European and the stripper, me and the European, me and the… I lose track. To be honest, it’s exhausting, and I feel I’m fighting for face time with John. When he notices that my underwear matches the European’s, he says, “Look, she’s trying to be like you! Isn’t it cute?” I want to punch them both in the face. And I know it’s going to get worse when John insists the European join us at his summer house for a long holiday weekend. I demand she not show up until Saturday, and to put the European in her place I book her a bus ticket. That’s right,Threesome Girl, you’re riding the bus! Without her around, John and I feel like a conventional, functional couple. At least we can masquerade as one. We spend the day at the beach, go swimming, sleep in a hammock and even make love just one on one, which almost feels tame now, like going to second base.

The next morning we pick up the European at the bus stop. She seems pissed off about the long ride, which makes me happy. We go to a local grocery store, where – shit! – I duck a business acquaintance in the seafood section, ordering three lobsters. And it’s weird, because we’ve never actually seen the European in daylight, we have absolutely no idea what to talk to her about. I suggest a game of Scrabble, knowing full well that English is her second language. Then we bring her to a dinner party at a friend’s estate. Big mistake. It’s a snobby crowd, John’s the only man there with two women, and I’m convinced a few people have figured out what’s up. “So how do you all know each other?” asks a leering guy in a seersucker blazer. I notice his girlfriend kicking him under the table. When we get home the European doesn’t even want to have sex. I’m relieved. In the morning John tells me in a delicate voice, “She feels like she is ruining our relationship and is upsetting you.” No shit! I can handle threesomes, cheating, even watching my boyfriend sleep with other women, but I can’t take the European.

Back on the bus, toots! But it’s not the end of our threesomes. I just decide that our sexual partnerships must be quick and professional. No more emails, birthday presents and pseudorelationships. No more daylight visits. No more weird conflicts. And then I do the absolute stupidest thing I could ever do: I have a threesome with John and his exgirlfriend, whom he’s managed to talk into joining us. Twice. The first time is a micro-disaster; the ex stalks out of the room when John’s on top of me as if she’s experiencing a Vietnam flashback. The next time we try, it gets worse. Although I hook up with the ex – and I admit it’s extremely hot, kind of like Godzilla vs Mothra – John sleeps with her and not me. Bad move. The next morning I flip out on John and burst into tears. As I weep, I know that out there, women are getting mad at their boyfriends for not listening to them or not getting them Madonna tickets or forgetting their shoe size, and here I am, screaming at my boyfriend, a guy I adore, for not fucking me right after he fucked his ex-girlfriend. Yet we keep on planning trysts. John and I have become the threesome Sid and Nancy. We’re moving beyond threesomes. We sleep with a couple we know – a good old-fashioned Ice Stormstyle wife swap. It’s surprisingly fun and easy.

We plan an orgy for John’s birthday party. I know, I know: How do you plan an orgy? It’s not like a game of Trivial Pursuit. We try to grow one organically – hotel suite, lots of booze, friends who are curious enough to make it happen. And voila! It actually works. John hooks up with a college friend of mine, though I step in and stop him from fucking her. But I’ve invited the woman from the couple we swapped with (hubby’s traveling on business), and she’s eager, as is an old guy friend I always wanted to sleep with. The wife, my friend, John and I roll into a foursome. But for the first time I’ve ever seen, John can’t get hard. I decide it’s a sign – a tipping point, like the morning Joe Kennedy got a stock tip from his shoeshine guy and decided the stock market was going to crash. This is going to end, I think – and badly.

The next morning John sits in the hotel and opens his presents. It’s starkly sad to see him rip up wrapping paper, the room stinking of sex, cigarettes and strangers. John feels like a stranger too. I know we’ll never truly be intimate and alone. We can’t go back to what we were. Worst of all, I know it’s equally my fault. We last just a couple more weeks. John, predictably, moves on to a sultry “mattress,” a model-actress – collagen pumped-up arm candy who looks perfect with him on the red carpet. We still talk, though, and when he tells me he likes her because she’s “traditional,” my cheeks burn. She’s making him faithful, he says, making me jealous and bitter for months. Maybe men really don’t want the fantasy in the flesh; maybe in the end they prefer a conventional relationship. Maybe fantasies have a way of interfering with, even confusing, reality. But I’d do most of it again – and I wouldn’t say threesomes are toxic. Just remember this: Get out while it’s still fun.

by Anonymous

Illustration by Istvan Banyai

Published in Playboy South Africa April 2013