The Divorced Business Owner Sleeping With a Younger Man

This week’s sex diary.

In this week’s story, a woman manages her housecleaning business, celebrates her daughter’s birthday, and finds time to cook a sexy meal for her new lover: 50, in a relationship, Brooklyn.

DAY ONE

8:20 a.m. The drilling has begun. The building next to me is doing construction. A gut reno, “to the studs,” which translates to “rich assholes.” But I’m used to it: I live in Greenpoint. My parents were Polish immigrants. I live in their building. Everyone else around us is straight out of Girls. But wealthier and ruder.

10 a.m. If I sound like a grumpy old lady, I am. But sometimes I’m not. I have a new boyfriend, Theo, who makes me feel like a totally different person. I’m divorced, my kids are out of the house, and in walks Theo. He’s ten years younger than me and has given me a sexual awakening. It’s been a few days since seeing him, since he had to visit his mom in the Midwest, but he’s back tomorrow.

11 a.m. I pop my estrogen pill. I’m in perimenopause. Who isn’t? I feel like it’s all I read about, although maybe that’s an algorithm thing. The pill is supposed to make my vagina less dry — how sexy am I? — and it works. I’d never tell Theo about any of this, of course. He thinks I’m a hot and horny divorcée — which essentially I am!

3 p.m. I do some calls and emails for work. I own a housecleaning business, and I have about seven employees. My role is totally managerial at this point. I don’t clean houses. I’m very good to the women who work for me. I was in their shoes, cleaning, for many, many years.

6 p.m. One of my daughters is coming over for dinner and to do her laundry. Both of my kids go to college upstate and live in dorms there during the year. During the summer, one of their wealthy new friends invited them to crash at her parents’ huge apartment in the city. It’s obnoxious, to me, but fun for my girls. They come home to see me every other night regardless. They want food and nurturing from me, and I don’t mind one bit. Their dad is involved with them, too. He lives in New Jersey now. We’ve been divorced for ten years and separated for 15. He was a shit husband, but he’s turned into a decent man and co-parent.

9 p.m. While watching TV with my daughter, I tell her Theo is home tomorrow. They love following my love life. I’ve had a few boyfriends throughout the years, but none of them were hot like Theo. And none of them had me quite this whipped — my daughter tells me the term is dickmatized. We both giggle. I tell her, “No comment.”

DAY TWO 

9 a.m. My daughter slept in my bed, and we wake up late. She has to rush off to her summer job, which is nannying for a family in the city.

10 a.m. One of my cleaners is having an issue with a dog, who is standing at the entrance of the apartment she’s supposed to clean and scaring her to death. I call the owners to see if they can come and get their dog. They screen my call. It’s so rude. My cleaner is literally terrified of this dog and doesn’t want to enter the apartment. I can’t blame her. I text the owners, who write back that the dog is harmless. My girl still won’t go in. I totally have her back. She doesn’t deserve to be frightened. I tell the owners that she won’t clean if they don’t come get the dog. They ignore my text!

11 a.m. I text again and again. Finally they respond that they’re at work and can’t deal with this right now. They’re like, “The dog is friendly!!!!” They’re very irritated by me. I know at this moment they’re going to fire us. I feel upset about that, but you know what? Fuck them. I tell my girl not to enter an apartment that she feels uncomfortable in. No way. I tell her she’ll get paid, by me, and not to worry.

2 p.m. I go on a long walk around Brooklyn to think about tonight. Theo picked a restaurant for us to go to, and I look up the menu on my phone. We’ve been together for about five months. We met online. We have not talked about if we’re dating other people. I don’t really care if he is. I’m not trying to marry the guy. It’s fun dating him, and it’s amazing fucking him. I’ve never been interested in remarrying and I already have my children, so what else do I really need from a man?

6 p.m. Theo texts me the address of the restaurant. It’s in Williamsburg. I can walk there.

7 p.m. I walk in sneakers and change into heels outside the restaurant.

7:15 p.m. Theo walks in a few minutes after me. He looks so good. He’s tan. He’s smiling. He walks over to the table and I stand up and we kiss — it’s a really sexy one. He tastes like mouthwash and smells like a dab of expensive cologne. I want to fuck him right here right now!

9 p.m. Another great meal with great convo. We always have the best time.

9:30 p.m. We go to my apartment and start having sex right away. He tries to go down on me, but I just want to have sex. I put him inside me, and we fuck on my bed. I want him to come inside me. It feels so much better that way, and it’s not like I can get pregnant anymore. We both come. That was insane.

10:30 p.m. We are both so sweaty. We take a shower together. I got breast implants a few years ago, and for the first time in my life, at age 50, I love being naked in front of someone else.

11 p.m. Theo can’t sleep over because he has an early day — he works in law enforcement — and he lives all the way on the Upper West Side. We kiss deeply before he goes, and even though I want to fuck one more time, I let him leave.

DAY THREE

8 a.m. I wake to a “Good morning, sexy” text from Theo. I think what young women don’t understand is how easy it is to keep a man’s interest. You just cannot be needy. You can have needs: sex, honesty, empathy — whatever. But you can’t be neeeedy. There is a difference!

10 a.m. My other daughter comes over. She wants to nap in her bedroom and wants food. Again: always my pleasure. She also wants a Theo update. The girls are so cute about him. They have not met him yet — I don’t see why they should? I am good at compartmentalizing.

2 p.m. I have about six new referrals just this week. That makes me feel really good. So I spend a few hours talking to new clients about what we offer and our rates. It’s strange how no one likes to pay their housekeepers. It’s, like, the one thing left that no one cares about in terms of pay equality. I must have said, “You get what you pay for,” 20 times or more this afternoon.

5 p.m. I take a yoga class. I do yoga or Pilates at least three times a week. I have to keep this banging body up!

7 p.m. Cooking dinner just for myself. I like being alone. I eat in front of the TV. I’ve earned this level of relaxation with me, myself, and I.

8 p.m. Theo and I are texting about what to do tomorrow night. He suggests some movie-under-the-stars event. I don’t want to sound like a whiner, but it sounds like that will kill my back — and the bugs! I pivot and suggest I cook for him, and we eat on my patio. What man can refuse that? Theo sends a dozen thumbs-up emojis, and I take out some cookbooks while I finish watching Presumed Innocent.

DAY FOUR

9 a.m. A trip to the farmers’ market is my favorite way to start the day. I buy all the good summer produce: tomatoes, basil, corn …

10 a.m. I do a few hours of work to make sure all my cleaners are set for the day and all my clients are happy.

1 p.m. Take a Pilates class at the local gym. If I’m being honest, I hate everyone there, but that’s okay!

3 p.m. More work housekeeping — no pun intended.

5:30 p.m. I pour a glass of white wine and start cooking. I am making a simple pasta tonight with a strawberry-shortcake trifle for dinner, but I want to make sure everything tastes just right.

6:30 p.m. Theo arrives with another cold bottle of white wine, which we open. He puts some music on on my record player. It’s jazz, but I’m bad with music, so I couldn’t tell you who.

7 p.m. We dance a little around the kitchen while kissing, and it is as cheesy and wonderful as it sounds.

8 p.m. Dinner is delicious. He’s cleaned his plate twice. He’s a very lucky man in this moment, and we both acknowledge that. I sit on his lap, and he reaches up my dress. My patio isn’t very private, so we move to my bedroom.

10 p.m. Such good sex. It was soft and rough and just so pleasurable. No one has ever made me come like this guy. I’m so, so, so attracted to him. He asks if he can sleep over, but I lovingly kick him out. My girls will be here in the morning for one of their birthdays, and I want to tidy up and prepare for that. It’s nice that he sort of begs to stay, though — even if the answer is still “no”!

DAY FIVE

7 a.m. Ouch, I’m hung-over. I think perimenopause and alcohol are a very mad match. I used to be able to drink like a fish with no issues the next day.

8 a.m. I’m cleaning my house and doing some baking for my daughters. I have a cake for later, but we’ll start with breakfast.

10 a.m. My girls arrive. I’ve made birthday pancakes for everyone with a great fruit bowl and beautiful healthy smoothies. After breakfast, we’re going into the city to see a show.

3 p.m. We’re on the train home. We saw a popular Broadway musical that was fabulous. One of my kids wants to be an actress, so she especially found it inspiring. Their dad had bought all three of our tickets, which was sweet. We are barely in touch, but he’ll do nice things for me now and then.

5 p.m. Back at my apartment, we’re having birthday cake and Prosecco and girl talk. I love hearing about my daughters’ lives. I am so blessed how happy and healthy they both turned out to be. It’s all I could ever ask for.

7 p.m. They want more details on Theo, and after two glasses of Prosecco, they convince me to FaceTime him. They want to see what he looks like. He picks up right away with a big smile on his face. He knew we’d all be here today, so I guess he knew what to expect. He says hello to all of us and asks about the play. He’s home watching TV and eating sushi. He’s super-charming to my girls and makes a big deal about me, telling them what a beautiful person I am. I know my girls are happy to see someone appreciate me so much.

8 p.m. The girls are going into the city to party with their friends. We had such a good day together. I’m exhausted!

DAY SIX

9 a.m. A small drama with one of my cleaners. Her key will not work. They’ve changed their locks and forgot to give her a new key. The people are in the Hamptons, and we all have to scramble to get her into the apartment. These people are really nice, however, and offer to pay a little extra for the lost time.

11:30 a.m. I’m deep-cleaning my own house. Cleaning is definitely my therapy.

1 p.m. Yoga class. I can’t believe how strong my core is. I’ve only been doing yoga for a few months, and I already see such a difference in my body.

4 p.m. I’m on my front porch reading, and the people doing construction walk over and try to make small talk with me. I cannot stand these people from “hello.” We’ve met before, but this is the longest conversation we’ve ever had. They’re just privileged trust-fund kids. I find it all so boring and shallow. They say they love the “diversity” of Brooklyn. Okay, sure. 

5 p.m. Yesterday, Theo invited me to a birthday party for one of his work colleagues tonight and texts to see if I’m going to go. I had told him I’d think about it, but I don’t really want to go. I don’t want to be the cougar. I’m not ashamed of it, but, honestly, the party just doesn’t sound that fun to me. Plus, let him miss me!

9 p.m. As I get into bed, Theo drunkenly calls to convince me to come and meet him. It’s loud, and I’m sure everyone is very drunk. There’s no chance. I tell him to have fun, but not too much fun.

DAY SEVEN

9 a.m. Sunday is the only day my cleaners don’t work, so it’s a day off for all of us.

11 a.m. I’m on the train to go visit my girls at their friends’ parents’ apartment, wondering how fancy it will be.

1 p.m. The apartment is insane. Their parents are both finance people. I don’t envy them one bit. We’ve done okay for ourselves over in Greenpoint.

3 p.m. Since I’m in the city, I text Theo to see if he wants to meet up after I visit with the girls. I’ve been to his apartment a few times, and it’s only a few train stops away. He takes a while to text back, which is unusual. Maybe he got into some trouble last night. Again, I’m fine with any of it.

6 p.m. It takes three hours for him to text back. He normally writes back instantly. He says he was napping. Could be true. He asks if I’ll come back into the city and cuddle with him. I tell him, “No way in hell.” The trains were so messy today. Instead, we make plans to go to dinner tomorrow night, after he finishes work.

8 p.m. Theo sends me three restaurant options and tells me to pick one. Everything feels right as rain.

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