In this week’s story, a woman flies to California to have sex with a hot actor in her hotel: 32, single, Los Angeles.
DAY ONE
6:30 a.m. As soon as I open my eyes, I have heart palpitations because I have a flight to catch this afternoon and wake up assuming I’ve overslept. Welcome to my inner life.
8 a.m. Showered with a fresh coffee, I think about what I have time to do before heading to JFK in a few hours. Will I have time to get a haircut and a blowout? Maybe … but wouldn’t it be nice to arrive in California with soft, straight, long yet shaggy hair? The look I always go for is “supermodel, the morning after.”
11 a.m. Quickly packing and closing up my apartment. I found a hair appointment — wish me luck. I remember my crotchless thong but leave my favorite lube behind since I’m bringing a carry-on.
4 p.m. On the plane, hair looking great, I take out All Fours. There are no words for how horny this book has made me. I feel like there are at least five middle-age women reading this on our Delta flight.
7 p.m. We’re on L.A. time now. I get a taxi to take me to my hotel in West Hollywood. I work for a talent agency, so I come to L.A. all the time and have a few favorite places to stay. This one I like because I stay in a small bungalow, and it’s private but not, like, scarily secluded.
9 p.m. I text the guy, Ian, that I’ve arrived and he can come over whenever he wants. He says, “Be there soon.” Hmmm. I don’t know if that means five minutes or two hours, but I don’t respond. I always play it very, very cool with men. It seems to work. About 25 minutes later, Ian texts that he’s at the bar.
10 p.m. We’re having a drink, but I am suddenly exhausted. Ian thinks I’m here for work, which is not entirely untrue, but I’m also here because a month ago, I fucked him at a party in New York. Literally, in the bathroom at a hotel party for a client. And now I’m curious if there’s chemistry. He’s an unemployed actor, but I can maybe help with that. He’s hot as hell and the sex was fire, so … here I am. But I’m wiped out! I tell him I need to call it a night. Being unemployed, he’s around all week, so I ask him if we can rain-check for tomorrow. He’s a gentleman and sweetly hugs me good night.
DAY TWO
8:30 a.m. Breakfast with one of my favorite clients here at the hotel restaurant. She is a writer and an actress, and I’m just her biggest fan.
10 a.m. Take a taxi to our L.A. offices. I feel empowered every time I walk in the doors, but I also feel very nervous and sometimes sick to my stomach. The entertainment industry is as brutal as you might imagine. Luckily, I have pretty thick skin.
1 p.m. Lunch with my ex. We broke up three years ago because I pretty much friend-zoned him after a year together. I just wasn’t feeling the lust. He’s an entertainment lawyer. He always has really good gossip, and today is no different. He’s telling me about an actress he’s dating and how much she hates herself. It’s unbelievable — this woman is gorgeous and talented. You never know, I guess.
3 p.m. Ian wants to take me to dinner tonight. I tell him to text me when and where.
6 p.m. Back in the hotel, I play with outfits and sip from a bottle of Champagne that was left here by the hotel staff, already chilled on ice. I contemplate masturbating simply because I’m horny but decide to wait to release everything with Ian. He says he’ll pick me up in 45 minutes.
9 p.m. After sharing a bottle of red wine and two bowls of pasta, I need this man in my bed. I have a strict “no drinking and driving” rule, so we leave his car at the restaurant and Uber to the hotel. We start fucking immediately. We do not need lube, not at all. Like, one minute of kissing and straight to me pulling his dick out and putting it inside me. This man has a beautiful cock. I wonder if he knows how lucky he is. I come right away and hope I can come a second time because he’s still going. Not that I mind.
10 p.m. I’m sexed out. It was amazing. I can tell Ian wants to sleep over, but I’m not into that, so I send him back to get his car and go home. I’m extremely satisfied.
DAY THREE
7 a.m. Wake up with zero regrets from last night. While waiting for room service, I take a morning swim in the hotel pool to help with the hangover.
10 a.m. Long day of meetings. On these L.A. trips, I try to interface with as many clients as possible. That also includes their managers, lawyers, assistants, etc. It’s good to know everyone, and I love it. A big part of my job feels like playing dress-up. I don’t know what the endgame is, but it’s a great way to spend my 30s. I do want to get married and have kids, but I’ve told myself that I don’t have to worry about that until I’m 35. For now, it’s all about killing it at work and having a lot of fun.
3 p.m. Working from the office for the second half of the day. A friend I did a big movie deal with wants to have dinner tonight. I’m pretty wiped out from the wine last night, and also, I want to reserve the option to fuck Ian later, so I make up some excuse about needing to see an aunt in Santa Monica later. It is kind of true — I do have an aunt in Santa Monica — and she does want to see me. But not tonight.
7 p.m. Shower in the hotel. Room service on the way for dinner. Ian texted earlier that he wants to come over. Should I take one night off and just eat a cheeseburger and watch reality TV? Yeah. I decide to do that.
DAY FOUR
9 a.m. At my office already. There’s a casting director here, taking a meeting with my colleague. I am trying to figure out how to ask her about casting Ian in something. It doesn’t really work that way, but it also can’t hurt to plant the seed.
1 p.m. I want to try this new restaurant tonight, but it’s pricey and I think Ian might have no money. I don’t care about that, but I also don’t want to make it weird since he always insists on paying. I decide to float the idea and let him make the call. I text him the name with a question mark.
3 p.m. Quick afternoon matcha with my boss. I really love him. He’s a dad and very warmhearted and drama-free. We talk about my clients and my performance and he pushes me to aim a bit higher, and I feel inspired rather than insulted. You can’t be so sensitive in this field; you won’t make it a day.
6 p.m. While I’m Ubering home, Ian texts that I should come over instead. Okay, so he’s too broke for this restaurant, but who cares. He says he’ll pick me up at seven.
7 p.m. I love that he always picks me up without me asking. It’s a turn-on. We drive about ten minutes toward his house, which is in Hollywood, kind of a sketchy area. But the house is adorable! It’s a tiny bungalow. Right out of a — dare I say — indie film. It’s decorated so cute too. I’m needing to fuck this man right now.
9 p.m. We just had so much sex. Now I’m starving. He makes me pasta with veggies in it — he’s a decent cook — and I ask myself if I should start seriously dating this guy? I wish he had more of a career. I know that sounds gross, but it’s my truth.
10 p.m. He drops me off at the hotel. We kiss good night with the most erotic tongue action. I taste the garlic in his mouth and I’m wet again. But I force myself into the hotel alone.
DAY FIVE
9 a.m. Breakfast with the aunt in Santa Monica! She’s kooky and I have so much fun with her. She moved out here to be an actress after high school and now sells real estate and designs jewelry, and I enjoy every second we’re together.
1 p.m. Since it’s my last full day here, I decide to work from the hotel. I need to start packing up, and I want to chill by the pool.
3 p.m. While lying out, I think about Ian and where I want it to go. I’m not dating anyone interesting in New York right now. I’ve recently met a few cute guys online, but they’re all so weird. One guy was really into kink, and that’s not my thing. The other guy already has two kids with two different women, and I’m not sure I want to deal with that. Both those guys, however, had stable jobs and good income. I am just not sure I can have an unemployed actor as a boyfriend. I decide to talk to him about his job before I leave tomorrow.
7 p.m. Tonight we decide to have a drink at my hotel and walk down the street for sushi afterwards. I’m happy I can put the drink on my room tab because I hate making him spend money on me, and he won’t let me pay when we’re out. Maybe he has family money? I kind of doubt it. Just not getting that vibe. I ask him about work … what’s his plan? He says he has some cool projects coming up. He’s booked some theater work. A buddy’s short film. He has some good gigs in the works — jobs that, if he books them, would mean good money and some street cred in the industry. I feel reassured. Also, he’s only 30. He tells me he works some “odd jobs” to help pay the bills, and it does turn me off a bit. Odd jobs are for your 20s, aren’t they? I know I sound like an asshole. Instead of sushi, I say we should order from the hotel and have it delivered to my room.
9 p.m. Back in my room, I decide to give him a blowjob. I want him to know how badly I desire him especially after that somewhat cringe conversation we just had. The blowjob turns into sex, of course.
10 p.m. We hug good-bye and I tell him I’ll see him in a month, when I’m back here for a work thing. He says he can always hop a flight to NYC, to which I say, “anytime.”
DAY SIX
7 a.m. I’m waiting for a car to the airport. It was a successful trip. I love L.A. and always feel sad saying good-bye to it. I could never live here, though. I’m very close to my parents and siblings, and they are all in New York. Two of my sisters just had babies, and I’m loving being an aunt and helping them with child care when I can. I’d never leave the family unit now.
3 p.m. By the time I get home, I’ve lost a full day with the time difference and flight delays. It’s nice to walk into my apartment, though. I strip off my airport clothes and stand naked — it’s too hot.
4 p.m. I order in and plop down on the couch with the remote. When the door buzzes with my food, I yell, “Leave it at the door, please.” I just don’t want to put clothes on.
6 p.m. Still naked, I take out my vibrator and try some new things. Like, going a little deeper instead of just on the clit. This is all inspired by the Miranda July book, by the way. Feels great.
9 p.m. I text Ian that I miss him. I love how low-key we both are about all of this. No drama. The casualness really works for me. The thought of him makes me smile. We text back and forth about little jokes and what we’re watching on TV.
11 p.m. Hard to fall asleep because of the jet lag, but I force myself to try.
DAY SEVEN
9 a.m. Head to the subway to go to my sister’s house because we’re going to drive to my parents’ house in New Jersey — she has a car and I don’t.
11 a.m. We’re all in New Jersey together. No one in my family gives a shit about my job, which is really nice, actually. All anyone cares about are my nieces and nephews. It’s a sweet relief after thinking about famous people and movie deals all week.
3 p.m. I go on a walk with my sisters and I tell them about Ian. They’re envious of the hot sex. They’re skeptical about the lack of a career. They remind me over and over about how money and stability really does matter, after all. But they’re in very different life stages than I am.
4 p.m. All this Ian discussion makes me feel guilty for talking about him. It feels mean. He’s such an awesome person. It’s just a horrible and unfair industry.
7 p.m. Back home. All the family time has me thinking about my future. Do I need to make some changes? Do I need to pivot? Cut Ian loose? Pursue him? I’m happy to feel confused — it means I care about my life, and it’s a sign that perhaps it’s time to reevaluate who I am and where I’m going.
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