'I’m usually very comfortable meeting men, but with him, I’ve gotten tongue tied a few times. He is a millionaire several times over and truly dominant in the boardroom and bedroom'
By submitting your email, you agree to our Terms and Privacy Policy. New York’s Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. This week a health-care professional dating a much older man: 26, straight, single, Long Island. 9 a.m. I wake up thinking about a guy I’ve been seeing, Ben. I masturbate to the last time I saw him.
2 p.m. Ben calls me. We talk for an hour while I’m getting ready for work. I’ve been aware of him dating other women in Chicago, but I’ve never explicitly mentioned that I’m also seeing other men, until this call. When he asks me to visit next week I tell him I’m busy — I’ve already made plans to stay with another guy, Nick, for the weekend. I met Nick on the same website that I met Ben, a website for millionaires. Ben gets upset that I’ve now confirmed that I’m seeing other men.
7 p.m. I wait for Michael at the bar. I drove into the city to meet him and got my own hotel room a couple of blocks away. Hangovers suck less in a hotel room. 12:30 a.m. He invites me up to his room. Simon has a gorgeous upper-floor suite and there’s a bottle of wine waiting for us. Good. He’s planned this out. A perk of older men. We talk for a bit more. I tell him how I am into some BDSM; men love to hear this these days.
8 a.m. I get up and realize I’ll be doing the walk of shame for the first time since college. I’m getting ready to leave and notice that his dry cleaning is hanging in the open closet. The tags have his full name … which he’s never told me. A quick Google search brings up a university dean’s bio. He’s from the West Coast, recently relocated to the northeast, and enjoys Saturday afternoons cheering on his old college football team and spending time in the garden with his wife. Just as I thought.
7 p.m. I’m back home now and texting with James, another guy I met online. He wants me to come into the city on Thursday to meet for the first time. He also identifies as dominant, and I generally identify as submissive, so it’s worth a shot. 1 p.m. I stop at the same hotel and get a room. I’m going to have so many Marriott points if this keeps up. Ben calls to ask how my day is. We talk about some politics and recent news. He gets another call and hangs up abruptly.
We’re fully clothed and grinding on each other like drunk college kids. He grabs my hair and puts his hand on my throat. I like to be choked. Then, doggy style. Good, I think, I don’t have to see his face. He flips me over for missionary. His hands are in my hair and he chokes me. He lightly slaps my face. I come.
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