sex diaries

The Long Island Woman Refusing a Threesome With a Pushy Couple

Once a week, Daily Intelligencer takes a peek behind doors left slightly ajar. This week, the Single Long Island Woman Refusing a Threesome from a Pushy Couple: Female, 33, Long Island, editorial assistant/social media consultant, mostly straight, single.

DAY ONE

12:15 p.m. Trainer texts to confirm plans tonight. He went to my high school, but found me on OkCupid recently. We’ve been out a few times and even though he’s not exactly my type (he’s a little more muscular than I’m used to), he is cute and sweet to me.

7 p.m. Trainer picks me up and takes me out for burgers. I’m not even hungry. We make awkward small talk and I wonder if we actually have anything in common. I kind of wish we could just get to the sex already.

7:30 p.m. Teacher messages me to say hello and I miss you. I miss him, too. He lives in another country and only spends the summers here. When Trainer is in the bathroom, I answer that I’m on a date. He writes, “Hope you’re having a good time. If you’re happy, then so am I.” I’m not that happy, but I’m okay. We both know I’m only going through the motions of dating because I can’t be with him.

8:15 p.m. Back at Trainer’s house, he finds a movie on TV. Why do we need the pretense?

8:17 p.m. We’re already making out, ignoring the movie. In a few minutes we’re both naked and I have no patience for foreplay tonight. I keep telling him to do me harder and he keeps falling just short of hard enough, but I orgasm anyway. I get on top until he finishes and then we both lay in bed together.

8:45 p.m. After what feels like only a few minutes, he’s hard again. I go down on him for a while and then he enters me from behind. I orgasm twice more, then he finally does and we both fall asleep.

10:30 p.m. Trainer is snoring next to me. The TV is still on but I don’t know where the remote is, so I listen to it as I drift in and out of sleep.

11 p.m. Check my phone and see a text from Engineer. I was supposed to hang with him the other night, but the trains weren’t running because of the weather. We were just friends — having met through mutual friends last year — but we recently fooled around after a party. I was looking for an easy one-night stand, but he said he wasn’t “allowed” to have sex with me. Turned out he has a girlfriend. They are in an open relationship, but she has to meet me before things go any further. He’s pushing for a threesome, but I’m not really interested. I’m open to threesomes but prefer not to be a guest in someone else’s relationship. Also, his girlfriend is twenty years older than us.

11:20 p.m. Make Trainer drive me home. Even though it’s only a few blocks, I don’t want to walk home alone in the cold, but I definitely don’t want to sleep over.

12:30 a.m. Finally get to bed, feeling a little sore from my night with Trainer but not quite sore enough.

DAY TWO

6:45 a.m. Message Teacher to say hi. Even though we promised to move on and just be friends (at least until the summer), our conversations always seem to turn to sex.

7:15 a.m. Touch myself as I think about our conversation and our summer together. As much as I’d like to find a real relationship and be happy, I also really want to be single this summer when he comes back.

12:50 p.m. Trainer texts me. He wants to see me again soon, but I can’t decide how I feel about him. He’s really sweet to me and the sex is good enough, but I can’t help compare every guy to Teacher and no one can measure up. And I mean that literally — his penis is huge. But he’s also just a really great guy and I don’t know when I’ll get ever over him.

2 p.m. Check OkCupid and find two new messages from guys in New Jersey. Too far. Yes, I recognize the irony that I won’t date someone from out of state, but I’m hung up on a guy who lives on another continent. I notice that Trainer has suspended his account. I can’t explain the sense of panic this causes me.

5 p.m. Remind myself that Trainer’s profile said he wasn’t looking for a commitment of any kind, which was part of why I agreed to hang out with him in the first place. I make plans to see him later in the week.

7:30 p.m. Agree to meet Engineer and his girlfriend after work tomorrow. I’m already pretty sure that I’m not interested in pursuing anything with them, and have tried to make him understand this, but he still wants us to meet. He says not to rule anything out. He wants to start with a platonic dinner and see how we feel. I agree, mainly because I’m very curious about her.

DAY THREE

10 a.m. Chat on Facebook with a cute guy friend who is going through a divorce. I have a tiny crush on him but it’s not something I would pursue. Yeah, I’m lying. It is something that I would totally pursue … if I thought it was even a remote possibility, but I know it’s not. He is completely out of my league.

5 p.m. Dinner with Engineer and girlfriend. I remember not to wear heels, as Engineer is shorter than I am. His girlfriend seems cool and I enjoy the conversation, but I feel no chemistry at all, with either of them. After dinner, she brings up the threesome idea and is just a little too pushy about it. She asks a lot of specific questions about what I’d like to try, as if it’s already a done deal. It makes me wonder if he has misrepresented the situation to her. I say I haven’t really thought about it and thankfully Engineer changes the subject.

8 p.m. We stop at a drugstore so they can buy condoms and batteries, and I excuse myself to go home.

DAY FOUR

12:15 p.m. Text Engineer that I had a nice time at dinner, but that I don’t see a threesome in our future. He says he’s surprised and recommends we hang out again before it happens. I clarify: It’s not going to happen. I don’t even want to have sex with him at this point.

2 p.m. Engineer asks if he can give my phone number to his girlfriend. I say no. What the hell is wrong with them?

7:30 p.m. Flirt on Facebook with a cute guy friend.

9:45 p.m. Browse OkCupid. Bored.

DAY FIVE

11 a.m. Text Ex-Boyfriend to say thank you. It is the anniversary of our breakup and despite my mixed up feelings for Trainer and Teacher, I’m actually pretty happy with my life right now. In a weird way, he’s responsible for that and I’m actually grateful. It’s the first nice “conversation” we’ve had in months. We both wish each other well and I feel really good about it.

8:30 p.m. Trainer picks me up and asks what I’d like to do. I don’t want to do anything but him. We eat a quick dinner and then go straight to his bedroom. We watch the first fifteen minutes of a cheesy nineties movie before my clothes start coming off.

8:45 p.m. He’s still so hesitant, as though he’s afraid of hurting me during sex. I assure him that he doesn’t have to worry; I like a little pain with my pleasure. He finally gets it and is rougher during sex, pinning me to the bed with the weight of his body. I wrap my legs around him as I orgasm. He flips me over and slaps my butt. Not a proper spanking, but it’ll do. He holds me by the neck and does me from behind until we’re both satisfied. Then he pulls a blanket over us and promptly falls asleep.

11:30 p.m. The movie I’ve been watching from Trainer’s bed ends and a show I’m not interested in watching comes on. I have to learn where he puts his remote. I wake him gently, because I want to go home, but he starts kissing me again. The roughness of his stubble on my neck feels so good and before I know it, we’re having sex again, all over the bed in various positions until we’re both sweaty and out of breath.

1:15 a.m. Wake up, still in his arms. I think maybe it’s not such a bad place to be. I run my fingernails up and down his back and kiss his neck and his chest. Eventually I’m going down on him while he pulls my hair. When we’re done, I remind him that we can’t fall asleep again because I need to go home.

DAY SIX

1:45 p.m. Chat with Teacher a bit. I tell him a bit about Trainer and he laughs at the story of my awkward encounter with Engineer and his girlfriend. I like that we can talk about this stuff. He knows how I feel about him, but he also knows that it’s not fair for either of us to wait around for each other.

9:30 p.m. Engineer tells me that he got the okay to have sex with me one-on-one, but he follows it up with a ton of questions about whether Trainer is cool with it and if we can get his permission. I explain to him that we’re pretty new and haven’t made the decision to be exclusive, therefore I don’t need to share every explicit detail of my life with him or get his permission for anything. Engineer gives me some story about how his “morals” don’t allow him to “sleep around” unless all parties are aware. I’m annoyed at his choice of words and all his attempts to defend them just dig him in deeper. He’s being a judgmental hypocrite and I’m completely over it.

11 p.m. Vent to my best friend about tonight’s annoyance. She agrees that Engineer is officially more trouble than he’s worth. “This is like the hardest you ever worked to not sleep with someone.”

11:30 p.m. Distract myself by chatting with a different cute guy friend on Facebook. I should’ve gone out tonight. I stayed in to catch up on work and then spent half the night too distracted by bullshit to get much work done.

DAY SEVEN

9:30 p.m. Drinks with the girls at a dive bar. There are no cute guys here and unfortunately Trainer is away for a few days. We exchange crazy dating stories and I think I win with my Engineer story.

11 p.m. A 23-year-old boy tries to hit on me. I’m more annoyed than flattered. When I try to turn him down nicely, he asks “What, do you hate me because I’m a foreigner?” Um … no. But I kind of hate him for asking such a ridiculous question.

2 a.m. Fall into bed alone, very drunk. Teacher should already be up and starting his day, so I message him to say good night/good morning.

TOTALS: 4 acts of intercourse; 2 acts of fellatio; 1 act of masturbation; 3 awkward dinners; 2 unwatched movies; 0 threesomes.

Threesome Sex Diary