sex diaries

The Writer Sexting Internationally and Trying to Ignore Alarm Bells

Photo-Illustration: James Gallagher

This week, a writer fresh off a five-year relationship and unsure about a guy he’s been talking to: 29, bisexual, London.


7 a.m. I wake up brutally hungover with a pounding headache, then reach for my phone on the bedside table. There’s a waiting Snapchat message from a now-familiar name. I smile a small smile and fall back asleep.

9:30 a.m. I know I should get out of bed, because it’s Saturday and it’s still relatively sunny for London at this time of the year. I think of how Adam, my ex-boyfriend, would insist that we spend a day like this one catering to his friends’ plans and not having sex. We were together for five years and broke up about three months ago. I met him at a work party — it was instant attraction, then very traditional dating. But we never lived together because he was hesitant about it, which was something that made me realize it was never going to work out between us. I do miss the ritual cuddle. But I’m also relieved that I can now do whatever the fuck I want.

10 a.m. I open the Snapchat message. It’s a little nerve-wracking, but I grin when it opens: “Is it weird that I’ve just woke up from dreaming about you?” So he is still into it.

A few weeks ago, I began chatting with a handsome American who lives in the East Village. It began on a gay webcam site, which I’m not exactly proud of — but ever since our initial contact, we’ve been exchanging messages about poetry and relationships and what we’d do to one another if we lived in the same city. I think I like him.

2 p.m. Snapchat messaging the American all day, and then meet my sister and one of my best friends for brunch. We eat Korean and they ask me how I’m finding single life. I lie and say I haven’t thought about it that much. One notes that this is the first time since she’s known me that I’ve really been single — I was with my girlfriend for seven years, and with Adam for five. I was just 16 when I met my ex-girlfriend, and then six months after we broke up, I was with Adam.

3 p.m. Lunch wraps up, and the American sends me a video of him playing with himself underneath some tight boxer shorts. I have to be incredibly tactical so my fellow diners don’t see me watching it. I hit the repeat button, watch it again, and again, and immediately get hard.

5 p.m. Watch shit films with my housemates, and go upstairs to send the American a video of myself grabbing the bulge in my boxer shorts. I make sure to angle it so it looks bigger than it actually is.

7:30 p.m. Do all the inane life admin before a working week begins. Then I talk to the American about poetry and how I’d like to read some aloud to him one day. He likes U.S. poets, which is great, as I love early Plath and Auden.

Day Two

9 a.m. My workload is mad. I look at the plus 2,000 emails in my inbox and don’t know whether to laugh or cry.

3 p.m. It’s nearing lunch, and I’ve been telling the American how much I want him. He seems amenable to the idea, then sends me a photo of his bulge under his desk. I get ridiculously turned on by this and wish I could go masturbate.

6 p.m. I pack up and joke with my boss that I’m not coming in tomorrow, I’m far too busy. From there, it’s onto a fourth date with a guy I met a few weeks back: Matt. We’ve got dinner planned.

He’s younger than me, at 24, and very nice. We met on Bumble, and I was a bit taken aback with his confidence to actually call me before our first date. We have a laugh … I can’t stop looking at him. He’s really good looking.

8 p.m. I’ve confirmed to Matt that I’m not looking for anything serious. This is a lie. If I met someone on par with the way I initially felt for Adam, I’d be with them in a heartbeat. I hate not being in a relationship, and not being told I’m desirable.

10 p.m. We take a walk around the neighborhood (we live in the same area) and then make out for quite some time outside my house. I can feel how hard he is as I pull him close. He’s an exceptional kisser. I think about inviting him in, but chicken out. Something doesn’t feel quite right yet.

Day Three

12 p.m. Mildly hungover after too much red wine, and awaiting the American’s Snapchat message like a junkie.

1 p.m. It arrives. He says he’s working from home and wants to spend the whole day wanking with me.

3 p.m. He takes a photo of himself looking ridiculously hot, topless, taking a conference call. I melt.

5 p.m. I make my excuses and leave work early, dashing home to get in front of my webcam. He appears on my screen and is better-looking than I remember. He keeps staring at me and saying “eyes” whenever I look up. This makes me feel good.

7 p.m. We do a slow dance around the idea of having full-blown cyber sex (whatever that is), but keep getting sidetracked into conversations about our hometowns, our families, and the differences between rural England and America. The two sound really different — largely because we don’t have semi-automatic firearms in my hometown. I tell him that my parents have been married for 33 years, together for 40. They’re super liberal and great. Pretty idyllic childhood, but a tough act to follow when your parents are childhood sweethearts.

Conversation turns to how we’d probably lose our jobs if we lived in the same city, as we’d spend all day having sex with each other. I can’t argue with this.

7:30 p.m. He’s got to leave my screen — my housemate is coming back. I could speak to him all evening. When I ask whether he wants to do this again, he says definitely, 100 percent. He seems as into it as I am. I mention that I’m in New York for work in the new year, and again, he seems into it. The idea of us meeting in real life seems more and more like a realistic proposal.

10 p.m. After the gym, I get showered and get into bed. I wank myself off thinking about the American and come so hard it hits the headboard. That’s never happened before. I realize I haven’t had physical, actual sex in about four months and feel like a totally tragic bastard.

Day Four

12 p.m. Uneventful day at work. Still loads to do. Still thinking about the American but also having increasing text exchanges with Matt. He’s very funny and sharp, and asks big questions for a 24-year-old. At that age, I was just taking pills on the weekend and living as cheaply as possible. Ah, London.

3 p.m. Agree to meet with Matt tomorrow for dinner.

4 p.m. Check-in text from my ex, Adam. It’s nice to hear from him, but occasional dispatches feel strange from someone I spoke to all day every day for years on end. We say a coffee on Sunday would be nice. I hope we’re right.

6 p.m. The American and I have been exchanging Snapchat messages, and I pluck up the courage to ask for his proper mobile phone number. He says his on-off-on-off thing (they’re off at this time) is deeply jealous and intense and is prone to snooping. I’m not really sure of the explanation, and tell him that he has no obligation to tell me his business anyway. The American says he does, because he likes me. I’m trying to ignore the alarm bells.

7 p.m. Meet friends for dinner and we have a few pints. Desperate to talk about the strange and attractive American man but resist.

Day Five

7 a.m. I’m feeling angsty so I go to the gym. Still feeling weird about the cagey response from the American re: his phone number, so avoid sending him a Snapchat.

8:30 a.m. Get into work, and really hit my stride. Get a lot done. Almost the weekend.

6 p.m. I leave work and Matt meets me promptly by Pimlico. We go to a Chinese restaurant and I feel quietly smug at how good the food is (this place was my idea).

8 p.m. We’re leaning in toward each other at the table. He’s really pretty. We talk about getting mashed in the back of Ubers and the construct of governance, and if anyone is ever really able to live outside it. His thoughts are abstract and free, mine very practical. I worry I’m maybe a bit too pragmatic/cynical for this blue-eyed 24-year-old.

10 p.m. We’re at his place, making out on his bed and it feels fucking great. I kiss down his body multiple times before slowly removing his clothing. I catch a glimpse of myself in the mirror and think I look pretty good, to be honest. He seems to be enjoying things a lot.

10:30 p.m. This feels too good. The actual act of sex is lot better than I remember, and I feel a million times lighter as soon as I start going. I keep my eyes shut for most of it and nuzzle my face into his neck. I’m imagining it’s the American for the entire duration, putting his words into practice on someone else, and repeating our imagined exchanges in my head (how he’d moan, what we’d do).

As soon as I come, I’m incredibly annoyed at myself for thinking about him, and feel really unfair to Matt. I take off the condom and we cuddle before falling asleep. My sexual frustration has lifted, but has been replaced by a thick smog of guilt.

Day Six

7:30 a.m. I leave earlier than I should, and give Matt a kiss as he stays in bed. We make plans and I hope I stick to them.

11 a.m. A colleague who is well on the cusp of becoming a friend asks me in the kitchen if I’m okay. I answer positively, but she says, I know you split up with Adam and it’s alright to talk about it. I’m stunned she knows, then remember a drunken conversation I had with her at a staff party about a week ago. Must try harder to keep mouth shut.

6 p.m. After exchanging messages with the American, I’m becoming increasingly agitated about the whole thing.

8 p.m. It’s a friend’s birthday that evening. I’m exhausted from partying all the time. I say I’ll be late and take my time getting ready.

8:15 p.m. I’m on my laptop undertaking a one-man mission to find the American online. He told me his workplace. He studied languages. It doesn’t seem enough info to go off, and so I resort to trawling LinkedIn.

9 p.m. It takes an hour, but I’ve found him. False name. False age. But it’s him. I know something isn’t right, and follow the breadcrumbs onto Instagram.

He’s in a very serious long-term relationship. The sort in which the boyfriend takes up the entire feed. My heart sinks, and the frankly ludicrous idea of us spending entire weekends together in New York fall into oblivion. Start to question how good of a man the American is, and feel terrible for his boyfriend. Their first Instagram photo dates back almost five years. I feel sick.

10 p.m. A friend — one of the few I tell everything to — picks me up in a cab en route to the party. Everything comes out. Our voices get high-pitched as we agree that people are, generally, fucking shit.

1 a.m. I’m hammered, but not feeling the party. I’ve ignored the American’s messages and I’m disappointed in myself for letting him get stuck in my head.

A mate who left the party earlier texts me. I was ready to go straight home, but instead, I get an Uber to his.

2 a.m. We sit and drink beer and talk about relationships. I start to get upset, saying that without Adam, I feel incredibly lonely. My friend puts his arm around me and tells me not to worry about being by myself so much.

Day Seven

9 a.m. I wake up hungover, with a watery stomach. I hastily book an Uber and say good-bye and feel thoroughly wretched.

1 p.m. Adam and I meet as arranged, which I’ve been dreading. This is not a good day to see him.

He arrives, and I remember how handsome Adam is: objectively, universally handsome. Ridiculously so. I feel sad and conflicted but realize that there is a total lack of sexual chemistry, too; we’re just old friends these days that were once in love. We get a coffee. It all feels eerily similar to the postpartum dinner I had with my ex-girlfriend: a quiet understanding that we love each other, but both painfully aware that we’d done the right thing. Adam says he misses me, and I really miss him too, but don’t want to say it or else I’ll cry. I really, really hate crying.

6 p.m. The American sends me a dirty picture, and asks how my weekend has been. I say fine, until I found out he was lying. There is a very long pause.

7 p.m. He begins to explain that he felt a connection, and couldn’t bring himself to tell me about his relationship and that really, he can’t stop thinking about me. He and his boyfriend are at a crossroads, he says. They’re not in a happy place. I’m not sure whether to believe him and we both agree that we shouldn’t talk to one another anymore. He takes my email address on the off chance he’s in town and single and wants to follow-up on all the conversations we’ve had about everything. I know this won’t ever happen. He sends me a five-line poem he wrote about me, and I repeat it over and over in my head. It’s very well-written, which almost makes it all hurt more.

11 p.m. American follows me on Instagram. I follow him back.

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The Writer Sexting Internationally and Ignoring Alarm Bells