sex diaries

The College Student Whose Exes Are Hooking Up With Each Other

Illustration: by Marylu E. Herrera

This week, a student manages complicated feelings about transition, their exes, and a new hookup: 22, single, Chicago.


8:30 a.m. My roommate’s door is ajar, which means she must’ve slept at her girlfriend’s. On most nights I can hear them having sex and it wakes me up because our walls are half an inch thick and her room is technically my closet. It reminds me of how single and alone I’ve been in my bedroom.

9 a.m. Take my estrogen. It’s been nine months now. Four since I’ve developed breast tissue. A little less than three since I need to shave half as often, two since my dick doesn’t get quite as hard. The last few weeks I’ve been crying like a madwoman. My second puberty. My body is changing so much right now, it’s hard not to feel alone.

11 a.m. Class ended last week, and I should really be getting ready for finals, but I can’t exert the energy. I text my friend H if she wants to make dinner together. I ask if we can make that miso soup she made for me last week.

4 p.m. I love going to the grocery store. I buy tangerines because they make for a romantic, simple, agreeable image. I’m developing a taste for simple pleasures that remind me there is an existence beyond queer panic and overwhelm.

8 p.m. H and I sit on my back porch and drink miso out of the pot we cooked it in. Broth drips off our spoons onto the grass and I remind myself to be grateful. Since I started hormones I’ve been trying to keep a running list of things going well that I don’t want to change, like sharing soup and spilling it.

H asks how I’m doing. I start talking about my ex, G.

I broke up with him NEARLY A WHOLE FUCKING YEAR AGO. I still romanticize him. He’s pretty and cis and is decidedly gay, not queer. I tell H I still think we can get back together, but he refuses to see me.

I tell H he won’t talk because he’s still hurt, I imagine, because of how it all ended. I broke up with him in a restaurant bathroom after he refused to have a threesome with the maître d’, who asked us to come home with him after I bummed a cigarette. I wanted an adventure — to watch a stranger fuck him in front of me — but he said no. So I told him he was anchoring me too hard and left him.

What I don’t tell H is that a week before the bathroom incident, I told him I wanted to buy women’s underwear and he said he wouldn’t like that. He actually said “ew.” It played out like a casual moment that he probably forgot, but I didn’t. I started hormones three months later. Thinking about that makes me cry.

10 p.m. After a while, H hesitantly tells me G has been hooking up with my ex, A, who I dated before G and dumped me when I got too invested. We all go to college together, so H knows them, too.

I don’t say anything for a while. A while for me is like 30 seconds. In those 30 seconds I decide I am going to proceed … with grace? But what would that grace be? Those fucking cis men.


8 a.m. H checks on me with a text.

11 a.m. I’ve come three times in the last two hours thinking about G and A in bed together. I make a pact with myself that I can’t jerk off to my exes forever.

So I text J that we should hang out. J is simple and sweet and cis and wants to kiss me and I think he may make me feel more sane, and acceptable. We make a plan for tonight.

9 p.m. I walk over to his place. We make out and he sucks my half-hard dick. I sleep over and forget to take my T-blocker.


9:30 a.m. I walk home without waking up J and tear up on the way. I sit down in the alley between my house and J’s. G’s is around the corner, A around the corner from him. I silently cry my fear away.

10 a.m. Get home. Roommate and her girlfriend are cooking pancakes. I close the door to my room and take estrogen and the T-blocker I forgot from last night.

10:30 a.m. Go for a run.

12 p.m. I find my friend at the library and attach myself to her hip. I haven’t done any school work in three days. I watch Real Housewives while my friend studies for the MCAT. She’s gonna be so successful.

8 p.m. I go back to J’s and sleep in his bed. I dream about A and G coming over for dinner at my parents’ house. They’re touching each other under the table and I’m pretending not to see.


11 a.m. Wake up in J’s bed. He asks if I want food. We make eggs. I hold him from behind. I’m doing well. I eat a bite. I think I’ve turned a corner.

1 p.m. Okay, I lied. I cry a bit when I’m alone at work. I’m a docent in the art gallery in our student center, where we average like seven walk-ins a day.

6 p.m. I go over to J’s after class. We torrent Everything Everywhere All at Once. The quality is grainy. I don’t like that, so I start kissing him. He asks if we can take off our shirts, I say sure, but as I take off what I’m wearing I surprise myself and tell him something honest … how I haven’t been with someone since I’ve developed these tiny boobs. He says he could play with them, if I’d like? Sorry, but that is literally the last thing I want,” I tell him. We both laugh. It feels like the first sweet thing in a few days.


10 a.m. Forgot my T-blockers again. I think it’s really bad to keep forgetting them but I forget about it. I walk home alone.

4 p.m. I walk to the library and attach myself to MCAT friend’s hip. I watch Real Housewives and she prepares for the future.

I realize I’ve forgotten to submit a paper so I send my professor a pity email, and say I missed the deadline because balancing gender transition with school has been “a bit of a whirlwind.” That’ll buy me some time.

9 p.m.  It’s Thursday so I can drink a little. I take too many shots and dance to a student DJ in a low basement. I’m secretly hoping I’ll see A and G. I don’t, sadly, but this is good for me.

11 p.m. I text J to come over. But I pass out before he responds.


10 a.m. Wake up nauseous and go on a run.

12 p.m. I text J that I’m seeing him tonight, no questions asked.

4 p.m. Work at the gallery. Crickets, so I lie down in the closet. I think about my transition, and wonder if I’ll feel differently this summer, away from campus. I sigh in the relief that it won’t feel this way forever.

7 p.m.  My professor answers. She totally understands. They always do.

12 a.m. I’m in J’s bed, and he asks to have sex. I hesitate and tell him he has the same name as my brother. I ask him to wrestle. I’m deflecting and trying to think at the same time.

I know he’s a bottom. I know I don’t necessarily want to put my penis inside him but I’m trying to move into something new.

I don’t know exactly how it happens but I tell J everything going on with A and G. He knows my history with them. I tell him that they’ve been hooking up. I tell him how unstable it’s been making me feel. I tell him I’ll have sex, but that I might start crying, but that I want to. He says okay. He is actually cool.

I last about two minutes. Then we can’t stop laughing.


9 a.m. I walk home. Avoiding the alley. When I get home my roommate and her girlfriend sipping coffee. Their legs are on top of each other.

2 p.m. I text H that I’m doing so much better.

7 p.m. Open my notes to figure out what that fucking paper was supposed to be about.

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The Student Whose Exes Are Hooking Up With Each Other