After its opening weekend, we noticed that Luca Guadagnino’s latest film, Challengers, had everyone hot and bothered but left some viewers wanting more. On social media, we saw the movie inspiring smutty fan fiction that would send even the raunchiest Wattpad users to horny jail, and even the film’s star, Zendaya, seems to be playing along with blurring the line between fiction and reality by releasing the inaugural “cover” of Challengers magazine. So we couldn’t help but imagine what the film’s epilogue could be in “Sex Diaries” form. The below is total speculation and contains spoilers for Challengers. Enjoy reading this in your incognito window!
This week, a recently retired and even more recently divorced tennis player is settling into single life and figuring out what he wants in a relationship. 33, single, upstate New York.
DAY ONE
11 a.m. Yawning, stretching. I’m a recently retired tennis player, and these days, I really luxuriate in the opportunity to sleep in after more than 14 years of an unforgiving athlete’s schedule.
11:15 a.m. After about 15 minutes of processing my new reality (a lot has recently changed in my life), I get out of bed and go over to the window. I just moved to an old farmhouse in the Hudson Valley, and I love looking out at the vast expanse of trees dotting my backyard and the river in the distance. I make a mental note to call my contractor; I’m building a massive playground for my daughter. I can’t wait to watch her frolicking out there.
12:20 p.m. Breakfast. Or should I call it lunch? A protein bar and a handful of almonds; old habits die hard, I guess.
2 p.m. Call with my agent. It’s stressful; he’s really pushing me to get back out there, career-wise, and I’m not ready. My other big life change is my divorce, which was recently finalized after a pretty brutal court battle. My wife, T, was also my coach, so our lives were heavily intertwined, and even though she cheated on me with my ex-tennis partner and former best friend, P, she showed no mercy when it came to splitting our assets. She says I wouldn’t have any of my major career achievements, and therefore most of my possessions, if not for her, which is true enough. She was a huge tennis star herself when we first met as teenagers and would’ve gone on to become a history-making legend in the sport if not for a career-ending knee injury. She was insanely talented and understood the sport in a way that few others do. Was it worth the emotional destruction? I’m still not sure …
3:45 p.m. My ex’s mom picks up our daughter at school and brings her home. The one thing T didn’t fight me on is custody; she’s busier than ever. She’s coaching a new up-and-coming player who seems on her way to winning the next Open, and of course she’s spun our very public divorce to her own benefit — she started a podcast about the effect that being an athlete has on your mental health and relationships. She’s also launching a clothing line and her own high-fashion tennis magazine. Since we’re technically co-parenting, we still have access to each other’s Google calendars, and I couldn’t help it — I looked through the pitch deck linked in one of her meetings. She’s modeling all the clothes, of course, and she looks amazing. I sometimes can’t believe she married me.
5:30 p.m. Dinner and a movie with my daughter. Getting to spend so much time with her is such a gift. We’re watching Puss in Boots again — she loves it and so do I. Even though I didn’t “win” the divorce, I don’t have to work much these days. I still have a few sponsorships going, which involves posting on my Instagram Stories and occasionally attending a dinner. I’ve never had so much control over my own life, and it’s a little scary. In a way that kind of turns me on …
9 p.m. Daughter is all tucked in, and this is when the loneliness tends to hit. I can’t help but wonder what my ex is up to right now, and I spend a few minutes Googling her. I snap out of it and open up Bumble. I initially tried to make an account on Raya, but I haven’t been approved yet and I’m embarrassed to ask anyone to recommend me. In the meantime, Bumble works for me; I like a woman who takes charge.
9:45 p.m. Chatting with R, a woman whose profile photos drew me in immediately — she has that slightly undone, French-girl look with red lipstick, and she’s a ballerina. I was hesitant about matching with her since she’s married. She’s in an ENM relationship, something I’m newly learning about as I reenter the dating pool. I guess that’s kind of what my marriage was — without the “E.” Long before my wife and I got together, when she was dating P, we were a pretty good trio. The night we both met T, we almost had a threesome, and I think we were both disappointed it didn’t happen. P was always a bit flirtatious with me, but he was also that way with basically everyone.
10:30 p.m. Things are getting hot and heavy with R. She tells me she’d love to meet in person … but she says her husband, who’s bisexual, wants to meet me, too. I’ve always considered myself straight, but maybe it’s time for me to test the waters.
11 p.m. Browsing a porn site, which I don’t normally do. I’m more of a romantic. Still, if I’m considering a threesome, I want to see what I’d be getting myself into. I fall asleep to the sounds of sucking and fucking.
DAY TWO
9 a.m. I’m up a little earlier this morning; my agent convinced me to show my face at some ESPN party. My ex is probably going to be there, so I’m dreading it. Or am I? Maybe it’ll be nice to see her. Maybe she’ll realize she misses me. Ha.
10 a.m. My stylist, M, is here. I really enjoy being dressed by her, but I’m not sure if it’s the clothes or just the feeling of being so carefully caressed by a beautiful woman. Sometimes I wonder if I should ask her out, but I don’t want to cross any inappropriate boundaries.
Noon In a town car on the way to the city. I respond to R’s message from last night, explaining how I fell asleep. She responds right away: “Can we meet soon? We’ll take very good care of you ;).” I’m still not sure how I feel about it.
3 p.m. Ahead of the party, my agent is having me take a few meetings about potential commentating roles. They’re all ready to hire me right away. It feels good to be wanted, but I tell all the execs the same thing, that I need another year or two to enjoy my retired life upstate.
8 p.m. Party time. Immediately upon walking in, I spot … P? Ugh. What is he doing here? It looks like he’s been here for a while. I’m not sure how he got an invite, but no one is paying him any mind as he chows down on mini-quesadillas and chugs margaritas. We make eye contact, and he smirks — he was always charming — and saunters over, still chewing. We had this weirdly intimate moment the last time we saw each other, and I’m still not totally sure where we stand. But before he reaches me, my agent grabs my arm. He wants to introduce me to some young tennis player he’s representing who’s apparently a big fan. I manage a stiff wave in P’s direction as I’m whisked away.
9:45 p.m. T finally shows, strutting in behind her new star player. Behind her, with a possessive hand around her waist, is the actor she’s been spotted with lately. I would be jealous, but I’m told he’s very gay and still closeted for some reason. Anyway, they’re doing the whole song-and-dance dinners at Carbone and pap walks around the Lower East Side.
10:15 p.m. She and the actor were immediately swarmed and are still posing for photos. Of course, I’m watching. I think now that we’re divorced, I’m starting to truly understand her. Our sex life was always mismatched; I enjoy the intimate moments leading up to sex — flirting, cuddling, foreplay — as much as or more than the sex itself. She approaches sex the same way she approaches tennis With ferocity and candor. Of course, it was the best sex of my life, every single time, but I always felt a bit hollowed out after, and she’d basically roll over and go to sleep, or worse, get out of bed to go downstairs and work. Usually, she was only in the mood after a big win.
10:23 p.m. P taps me on the shoulder. He says it’s nice to see me, and it feels like he means it. He updates me on the extremely unemployed lifestyle he’s been indulging in. We joke about whether the boarding school where we met would hire him. I realize how intensely I miss him.
10:30 p.m. They start passing around dessert: mini-churros dipped in white chocolate. P inhales three of them, gazing into my eyes every time he takes a bite. Is he … ?
11:13 p.m. I come back from the bathroom to find T and P talking to each other, and a wave of anger takes me. Suddenly I don’t miss him at all. T looks angry and irritated and eager to get out of the conversation, so I swoop in. We haven’t seen each other in weeks, but we need to discuss plans for our daughter’s birthday. Logistically, we’ve always understood each other well.
1:05 a.m. It is way past my bedtime. I duck into a bodega on the corner to grab a BEC and a chocolate bar for the two-hour journey home. I love being able to indulge in stuff like this now. But I ultimately regret my decision; while waiting for my order, I watch P get into his dingy SUV, which is parked across the street. He doesn’t drive off, and I soon understand why. Coming from the opposite direction and now wearing a baseball cap and a hoodie, T power walks to his car and gets in. Wow. So they’re still fucking. I shouldn’t be surprised, but I am. I decide then and there that I’ll be going forward with the threesome.
1:20 a.m. I take one bite of my sandwich and doze off in the back seat of the Range Rover before I can finish the rest.
DAY THREE
7 a.m. I wake up disoriented and extremely uncomfortable, with a sore neck. My ex-mother-in-law gets my daughter ready for school while I try to sleep off a hangover in my bedroom. Even though I only had one drink last night, I feel like a messy 22-year-old. Am I a bad dad?
1 p.m. Awake again, for real. Feeling refreshed.
3 p.m. I gather the courage to text R. We agree to meet for coffee first, just to see what the vibe is like. We decide on 4 p.m. tomorrow, and I text my ex’s mom to see if she’s available to babysit again, just in case. I tell her I have a date, hoping it’ll get back to T.
5 p.m. My daughter’s home, and I decide to try and avoid screens tonight, still feeling some residual dad guilt. Instead, we jump on the trampoline, then I read her three more chapters of Frindle.
8 p.m. My daughter is sound asleep, and I’m exhausted too. I take a bath and then get into bed.
DAY FOUR
9 a.m. I’m up. Big day today …
11:32 a.m. When I was training for tennis, I’d go to the gym every day, sometimes twice a day. Now, I stick to twice a week. I try to pump myself up for the date with some weights and finish off with an hourlong trail run. Turns out I have a lot of nervous energy to burn off.
3:45 p.m. I’m at the coffee shop, trying to act normal … whatever that means. I sip on a mint tea. No caffeine for me, and it’s helping with my nerve-induced nausea.
4:02 p.m. R and her husband, D, are walking in. He’s taller than me — so is she, actually. She’s wearing a white button-up with no bra and a gold R necklace, tucked into black wide-leg jeans that somehow still hug her ass. Her hair is clipped back with strands framing her face just so. D is in a leather jacket, a plain white tee, and light-wash jeans that fit him so perfectly I feel both underdressed and overdressed in my linen shorts and Ralph Lauren sweater. I was trying to show off my legs, but I feel ridiculous all of a sudden. I should’ve called M for some advice. I get up to greet them and they both hug me and kiss me on the cheek. Am I already turned on?
6:15 p.m. We’ve been talking for more than two hours. They’ve explained their approach to ENM and how they first opened up their marriage, and I’ve spilled my guts about my divorce. Despite that, they both still seem interested — in me and in what I have to say. It’s really wild to have two people paying such close attention to me, laughing at my jokes, touching my arm … They invite me to their house, which is a 15-minute drive away. I drove here and so did they, so I follow them, wondering what they’re saying about me inside their Prius.
7:42 p.m. We’re all on the couch, halfway through a bottle of wine, when R trails off mid-sentence and turns to me, lazily tracing my jawline with her fingertip. I’m immediately turned on; I already have a semi when she finally leans over and kisses me, and it soon becomes fully hard when she brings her hand down to my crotch. D, on the other side of me, starts kissing my neck, and it feels good. I like this, I think. My hands are on R’s waist. D takes one of them and guides it to his crotch so I can rub his dick, and I do. It’s a natural enough movement; I’ve done it plenty of times to myself. He’s slightly bigger than me and significantly girthier, which makes me insecure. Actually, his penis reminds me of P’s. Ugh. Not what I want to think about right now. I focus on the kissing and fondling that’s happening instead.
8:07 p.m. We take it to the bed and start undressing. I strip down to my boxers; R is in her button-up and a thong; D is fully naked. I start unbuttoning R’s buttons, still kissing her, while D fondles us both.
8:20 p.m. R wants me to go down on her, which I do happily, while D eats my ass. This, I’m not so sure about. I try to focus on what I’m doing, but I can’t. I stop and say I’m not really into the ass eating. R and D both look a bit disappointed, but they say it’s fine and that it’s not for everyone. D asks me what I’d like instead. I ask if we can all cuddle. I spoon R and D spoons me, and I feel so held. But when I feel D’s dick against me, my own immediately deflates. It’s the weirdest thing. R keeps rubbing her ass against it to try and bring it back, but it doesn’t work. I’m so embarrassed.
9 p.m. We’ve tried just about everything to get me hard again. I apologize, and they tell me it’s fine, but I can tell they’re both still horny and out of patience. We all start kissing again and then they start fucking, one of them occasionally turning to kiss me. I feel like such a loser. As soon as they’re done, I tell them I should be getting home, and they explain the way out, clearly ready for round two, this time just the two of them. I quickly dress and leave them in bed.
11:09 p.m. Home. I think threesomes are not for me. I fall asleep the moment my head hits the pillow.
DAY FIVE
10 a.m. I wake up to a notification that I’ve been approved for Raya. This timing couldn’t be better. I take a long, hot shower to wash off the embarrassment of last night and then text R and D to thank them for the experience. “Sorry it didn’t go as planned,” I write. “I guess this means I’m not a threesome guy.” Does it also prove I’m straight? I’m not sure, actually. But for now I’ll stick to single women on Raya.
3:22 p.m. It turns out that E, a recently retired women’s soccer pro I’ve met before, lives nearby. We match and start chatting. She asks me what I’m looking for. “I’m a romantic,” I finally write back. She says she’s looking for something more serious — and monogamous — too. She’s bisexual and says playing professional soccer was a lot of fun, but it made her love life chaotic. She wants stability now. I can offer stability, that’s for sure.
4 p.m. I ask her to meet me for dinner tomorrow at a nice Italian place. She says “yes” right away.
9 p.m. I have a bath and start reading this book called Conscious Loving the Journey to Co-Commitment. I realize co-commitment is what I want.
10 p.m. In bed, still reading. I fall asleep 30 pages in and dream that my date goes so well I propose at the end. Maybe I need to chill.
DAY SIX
11 a.m. Another trail run to calm my nerves; I end up accidentally running a half-marathon.
2 p.m. I eat a PB&J and take a nap. I want to be at my best tonight.
6 p.m. I make myself an espresso and down it in one gulp. I put on my nicest black jeans and a white button-up. Yes, this outfit is inspired by R. She looked good! Sue me.
7:30 p.m. I’m seated at a cozy corner table, and E walks in right on time. She’s wearing a simple black dress and looks gorgeous.
11 p.m. The restaurant is closing, and we’re still deep in conversation — we’ve talked through our entire relationship histories and I’ve told her all about my daughter, whom she thinks is adorable. She Uber’d here, so I offer to drive her home. Before we get in the car, I ask if I can kiss her and she agrees. We make out like teenagers, giggling and shy with an undercurrent of fervent need. I ask if she’d rather come home with me. “I’d love that,” she says.
11:45 p.m. We’re in bed. I’ve lent her a T-shirt to wear and she looks incredibly hot in it. We start making out again, but it’s slower and more sensual, like we’ve got all the time in the world. There’s no rush. We dry hump a little but don’t have sex, instead cuddling and talking for another two hours. This is bliss. I think I’m in love.
DAY SEVEN
10:24 a.m. I wake up and we’re still spooning. I’m the little spoon, so I turn to kiss her. “You’re perfect,” I tell her. For the first morning since my divorce, my ex hasn’t even entered my mind.
11 a.m. We’ve both fallen back to sleep; she’s using my chest as a pillow, and I lean down to kiss the top of her head. She stirs and kisses my cheek, then my other cheek, then all over my face. My eyes well up and she asks me if something is wrong. It’s the opposite, I tell her. I’m just so grateful for the affection. She smiles and kisses away my tears, then tells me she’d like to sit on my face. My favorite position! I can’t believe my luck with this woman.
2 p.m. We’ve spent the day in bed and are both starving, so I order sushi. I ask if she’d like to stay over again tonight. She says “yes” without hesitation. I put in another order, this time a grocery delivery, for the electric toothbrush she usually uses, her favorite toothpaste, and all the skin care and hair products she likes. Might as well, right?
3:10 p.m. We put a movie on and dig into the sushi, then fall asleep cuddling again.
5 p.m. I’m awoken by the doorbell. Ah, the grocery delivery. I let her sleep and clear off the right side of the bathroom sink for her, arranging everything neatly on the vanity. This feels so right.
5:40 p.m. She wakes up and goes to pee, yelling that she loves the sink setup. “I just realized you haven’t been inside me yet,” she adds. “Let’s change that.” I hear her showering, and half an hour later she comes out completely naked and all lotioned up.
6:30 p.m. We’re kissing. She takes off my T-shirt and boxers and pushes me onto the bed. We get to it and I only last about five minutes. I’m a little embarrassed and tell her it’s been a while. She tells me not to worry and we go back to cuddling, which we do for the rest of the night while watching Ted Lasso.
10 p.m. I fall asleep with her in my arms, and I dream about having sex with her again — except this time, P is there, watching. Laughing at me. Joining in. Fuck. What does this mean …
Want More Challengers?
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- A Film Lover’s Guide to the MMF Threesome
- A Courtside Wardrobe for Keeping Two Men
Katja Vujić , 2024-04-29 20:15:29
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