This Week’s Sex Diary: The Mom Role-Playing As a Naughty Student

As told to Alyssa Shelasky, Cut columnist and editor of the “Sex Diaries” column since 2014. She is also the author of the essay collection ‘This Might Be Too Personal’ and the memoir ‘Apron Anxiety.’

Illustration: Marylu Herrera

In this week’s story, a woman and her primary partner bring another couple home: 49, in a relationship, Manhattan.

**9 a.m. **Stephen and I started dating three years ago. We’ve been in an open relationship the whole time. When we met, I was in an open relationship with someone else who was my primary partner. When Stephen and I became primaries after about six months, I broke up with the other guy. Neither one of us has another steady partner right now. We’ve lived together for a little over a year. We each have two kids from previous marriages who are with us on and off throughout the week.

Stephen’s sister is visiting, and we’re all hanging out in the living room before she leaves later today. It’s been nice but also a lot of socializing for me. Stephen says we can cancel our plans for tonight if I want to, but I tell him it’s fine. I don’t like to cancel plans; it gives people the wrong idea.

**12 p.m. **I meet a colleague from my former nonprofit career at a café downtown. We talk about having or not having kids. She is married and doesn’t want children. I never tell anyone they should have kids, but I can’t imagine life without mine.

2:30 p.m. I walk over to the wax salon. After the lady, whom I love, waxes my pussy, she says, “Now you are cute again!” Once I asked her if she was going to retire, and she said, “no,” she’s “going to be waxing” my daughter someday; I’m not sure how I feel about that. Anyway, it was nice to see her, and now I’m cute again, ha!

3:30 p.m. Two texts from Ben. He got in touch yesterday for the first time in eight months. I had assumed he wasn’t into me. Our first date was a pretty standard date for what I was looking for — primarily sex with a good connection. But that day, we talked about the fact that we both are into role-play. So on the second date, we role-played that he was my doctor and I was the patient. He did it just the way I like it, being in the role from the time that I showed up and not dropping the role until he came and we were lying together afterward. We talked a little that night about roles we’re into, and a teacher-student dynamic came up. When I texted him back last night, with no introduction, I said that my parents were so disappointed in my last test score and I really hope he’ll find a way for me to make it up. So now we’re really in it.

**5 p.m. **I ask Ben if I could make up for my bad test score on Monday. He says, “I’ll warn you that it’s going to take quite a bit of effort to get you to a passing grade, but I think we’ll both be satisfied in the end. Monday after class sounds good.” I respond, “Oh, I am definitely going to try really hard and do everything you say. I want to prove to you how good I can be.”

6 p.m. Stephen and I leave to meet a couple we met online. We picked a bar that’s close.

**7 p.m. **We all sit in the back and talk. I can tell that Yvonne is not in as good shape as Stephen would prefer, but she has big breasts, and I don’t, and he likes the variety. She’s laid back and not pretentious, which is good. Her boyfriend, Dan, also isn’t really my type. But I find my bar is lower with a guy in a couple than if I am going to be with him alone. If I’m alone with someone, it’s just them turning me on so I prefer to be really attracted. Watching Stephen with another woman turns me on, so I can always focus less on the guy in a couple.

8 p.m. We take them back to our apartment and hook up. When Dan first undresses, I can see his erection through his boxers. I love that. So many guys over 45 have challenging erections. Which I totally understand and it’s not that I get annoyed, but I find it super-hot when a man gets an erection for me. We get in bed and undress the rest of the way. His dick is thick, not quite as long as Stephen’s. I’ve never really seen a bigger dick than Stephen’s. Maybe once. But Dan is a good size. We make out for a while, and then he gets a condom.

8:30 p.m. Stephen and Yvonne are on the bed with us. He gives her oral for a while, and she goes down on him too. She seems to really like him giving her oral, which is often the case; he’s good at it. As I mentioned, I find it super-hot watching him with other women. I especially like when they go down on him, and then when he fucks them. It’s really good watching him from behind when he’s fucking someone, because that’s an angle that I never get to see when he’s with me. Dan and I had decent chemistry, and fucking him was fun. I am blessed in that I come really easily as long as the guy is reasonably tuned in to me and not too small. I watched Stephen and Yvonne for a lot of it, and Dan watched them too, which I liked.

**9:30 p.m. **These casual encounters never last long, and I like it that way. The couple leave and it’s just me and Stephen in bed, falling asleep.

7 a.m. Stephen has a soccer game an hour away, so we hop in the car. I go with him because I like to run around the park while he plays there.

1 p.m. Finally home, eating lunch together. I tell Stephen about my plans with Ben, about the back and forth and the role-play. He remembers Ben and thinks the whole thing is hot. Stephen never gets jealous unless someone makes me come more than he can, which hasn’t happened since very early in our relationship.

3 p.m. It’s nice to have the house back after hosting a guest for a week and “guests” last night.

5 p.m. I suggest to Stephen that we go out. I order an eau de vie. There’s a really nice energy between us tonight, which I don’t want to attribute to the alcohol but it probably doesn’t hurt.

9 p.m. Back home on the couch, Stephen starts rubbing me in this way that he does when he wants me, and it inevitably turns me on. I am always amazed when I fuck him for the first time after being with someone else, at how perfect he feels in me and how much better it is. He comes in me, from behind, which I like because he seems to comes hardest that way.

7 a.m. Stephen is up and out. He works in health care and starts a new job at a hospital in the city. It means I have the house to myself and can putz around yet still have plenty of time to work. I’m a freelance writer and not super-busy right now, but I have things I need to work on.

**10 a.m. **I write a little, then check my bank accounts and my budget and make sure I’m solvent. I make a to-do list. Feeling productive.

11 a.m. My brother calls. He’s been having problems with his fiancée since May; they were off and on all summer. He says it’s over for real now. He sounds numb.

3p.m. Taking a break. Tired of working. Make a salad for lunch.

5 p.m. Ben texts, confirming that tonight works but that he has to grade papers so I’ll have to leave on the early side. He says he’s looking forward to seeing some hard work from me and that he would hate to see me fail. I tell him I will definitely show him how bright I am.

5:30 p.m. Stephen has his kids here tonight but I don’t have mine, which is why it’s a good night for me to go out. We talk a little about the new job; it seems good.

6 p.m. I take a shower, then I put on my schoolgirl-fetish costume that I’ve had for a while. It’s a white collared top that ties between my breasts and leaves my stomach bare, and a red plaid skirt that is so short it barely covers my ass. Then I put on a see-through white thong. I call down to Stephen, who is with his kids in the kitchen, and ask if he would come help me with something. He comes up, and I ask him how I look. He kisses me really deeply, then grabs my ass and tells me I look hot. He looks turned on, I love it.

7:30 p.m. I knock on Ben’s door. He lets me in and takes my coat. I’m pleased with his reaction; it’s subtle, but he notices my outfit (obviously hard to miss). We go into the living room and start talking. He tells me that he’s always been distracted by me. I say I’ve been distracted by him too. He tells me all of the teachers are after me, that they talk about me in the break room. He asks me whether I’ve been with any boys my age. I have a moment where I have to decide whether I’m going to play the innocent student or the slutty student. I choose the latter, because that turns me on more. I say I’ve been with lots of boys. He tells me to take off my clothes, then gives me oral sex from behind while I lean on the back of the couch. I suck his dick. Then he fucks me on the couch really hard.

8:00 p.m. Did I mention Ben is 30? We move to the bedroom and fuck more. We keep up the roles. Then we both come and he immediately switches to telling me about his real life. I know he is married and open, but he told me he started dating someone else who had been taking up a lot of his time. I have no problem at all being the third in line (or, for that matter, maybe I was even further down the list). I like having “comets”: men who come in and out of my life. I’m also not interested in emotional attachment with anyone but Stephen. Role-play is good to inhibit emotional connection.

9p.m. Before I leave, we talk about other scenarios we want to try next time. I tell Ben that I’ve never been with another man who is so into role-play. I’ve always been into it; I remember trying to get my high-school boyfriend to do it. I forget to tell him that I often fantasize about a boss-intern scenario. I’ll text him that later.

**12 a.m. **I tell Stephen all about my night. It turns him on for me to talk about being with other men. We almost always fuck after I get home from being with someone else. It’s always really good sex; it’s like I’ve been primed and I can come even harder. Tonight I go on top, because we both know that’s how I come the hardest.

8 a.m. Stephen seems a little distant this morning. Maybe it’s stress from the new job. I don’t ask because I want to give him space.

10: 30 a.m. I’m feeling kind of depressed. I wonder if it’s a downward swing from the alcohol the other night. I pretty much gave up drinking a few months ago, but I thought maybe I could drink occasionally. Maybe I can never drink again.

11 a.m. I’m supposed to be working on a freelance writing project, writing a case study about innovation in the environmental sector, but I can’t motivate myself at all. I’m just sitting around feeling sorry for myself and eating chocolate.

**3 p.m. **Playing games on my phone.

**7 p.m. **The funk lifts. I finish a draft of my freelance project and feel good. Stephen is working late tonight.

9 p.m. Stephen gets home and seems really disconnected from me, still. I ask him about it, but he says it’s nothing.

7 a.m. Stephen is off to work. I’m trying to motivate myself to write.

**10 a.m. **I’m on the phone with a friend who’s having trouble with her parenting. Her kids are still little. I’m so glad my kids are teenagers and self-sufficient.

**3 p.m. **Working, but not getting much done.

5 p.m. I don’t know what’s up with Stephen. On Wednesday evenings, we have all four of our kids together for dinner. We usually buy prepared food together, then pick up his kids and drive home. But Stephen hasn’t said much to me about our plans tonight. Does he want me to take care of it myself? I don’t really want to, but I know the kids need to eat.

**6 p.m. **I end up at the store, buying a simple rotisserie chicken. I text Stephen to see what his timing looks like … my teens are already at the house. He says he’s still picking up his kids and running late on everything. I feel annoyed by this.

**7:30 p.m. **Stephen is not helping with dinner or clean-up. I get it, he’s tired, but I’m tired, too, so I get annoyed. He makes a snarky comment about how I stack the dishes on the rack and I snap at him a little, then he leaves the room. Now I’m very upset.

**9 p.m. **Stephen tells me that the wife of a friend suddenly passed away. It’s very upsetting to him and me. It’s obviously not the only thing affecting his mood, but he’s not sharing more with me. I end up laying in bed with my daughter, who is dealing with her own stuff, and I want to be there for her.

9 a.m. Meeting over coffee with a colleague.

11 a.m. I text Stephen about how shaken I still am about the death of his friend’s wife. He is too.

1 p.m. Networking call, don’t think it will go anywhere.

3 p.m. Trying to work, very distracted by the fragility of life. I also hope my brother is doing okay; I haven’t heard from him since the other day.

6 p.m. I work on a school project with my son tonight, then make dinner for my kids. Stephen is scheduled to work late.

**9 p.m. **I ask Stephen what’s going on, again! He says he’s depressed. This isn’t news to me. We talk about his recent therapy session and he confesses that he told his therapist he wants to be dating more. He had a steady thing for well over a year with this woman who I really liked, but it ended in the spring and he really hasn’t dated alone since then, only couples with me. It kind of makes sense, but I still challenge him because it seems like he’s had opportunities that he hasn’t acted on. As we talk, I’m feeling panicky.

I’ve struggled with jealousy ever since we became primary partners. I’ve worked hard to understand it, including a ton of therapy. I feel like I get closer and closer to figuring it out but never quite do.

Sometimes when the jealousy is really bad I think it would be easier to be monogamous. But then I think about all of the benefits that I get from it, the role-playing (which Stephen won’t do), my ambiguous relationship with my best guy friend, and the time some guy came over to fix my computer and I made out with him before he left … I don’t want to give that up.

**9 p.m. **After a lot of talking, Stephen starts to come on to me. He has a huge erection. But tonight, I just can’t. Which is incredibly rare for me. I have barely ever rejected his advances.

8 a.m. I go running to try to get rid of the nervous energy.

**10 a.m. **Texted Stephen that I can’t stop thinking about how good his cock looked last night. He said it will look good again tonight 🙂

1 p.m. While eating lunch, I tell myself that I’m feeling reasonably good even though my daughter is home and struggling, which weighs heavily on me at all times.

5 p.m. Stephen and I take all our kids out to dinner. It’s a really great time.

**9 p.m. **Stephen and I have incredible sex. It’s been such a crazy week, so emotional. But the sex was amazing. I felt connected, and he made me come a lot (as always). It was nice to lie with him afterward.

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The Mom Role-Playing As a Naughty Student