In this week’s story, a woman takes a trip to relax by herself, then meet up with an old flame: 30, single, Italy.
DAY ONE
7:30 a.m. Wake up excited for my first full day in Naples! I just got in last night. The plan is to spend most of the week solo in Naples and the surrounding area, before meeting up in Capri this weekend with a friend who I have a complicated (but sexy) history with.
9 a.m. I have a slow morning coffee in my little Airbnb and get ready to head out for a day of sightseeing.
12:13 p.m. Wandering around the city’s center to take in the sights. This entire trip was somewhat of a whim; I normally enjoy my life as a journalist in New York, but so far, 2024 has been challenging, to say the least. The year started with a case of COVID and a devastating breakup with a boyfriend I’d previously thought was The One. We were only together for a little over a year, but I was basically head over heels that entire time and just put a lot of energy into the relationship. He was kind, attentive, protective, attractive, and checked off a lot of boxes for what I wanted out of a partner, but he always maintained a certain aloofness. I figured we would just overcome it with time. But it turns out that aloof streak won when he basically slow-ghosted me over the course of a few months. He went away for the holidays and basically never came back. Or back to me, at least. It was my first big ugly-cry heartbreak. I cooked up this trip as a kind of Eat, Pray, Love healing excursion.
2 p.m. Aimlessly walking around the city after lunch at a street-side café. I’d like to think my waiter was flirting with me, but honestly he was probably just … being Italian. My real lunch date was Joan Didion, specifically The White Album, because why not be inspired by one of the greats during this week of delights.
6 p.m. Against my better judgment, I open up Feeld and see that one of my matches has messaged me. This was another post-breakup-delulu decision I made just before this trip: getting back on dating apps. This guy — whose profile name is literally just “Italian” — seems hot, but I don’t know much more than that. No harm in at least saying hello …
8 p.m. Quiet dinner and glass of wine at home, and then bed.
DAY TWO
9 a.m. Later wake-up today, and spend even longer lounging in bed. In real life, I cover national politics for various publications. I find it to be exciting, meaningful work, but it’s pretty all-consuming, so I intentionally took a complete break away from it on this vacation.
11 a.m. I’m really trying to remind myself to just fucking relax and be on vacation. Part of this entails a quick masturbation sesh, where I start to fantasize about any one of the gorgeous men I saw on the street yesterday having their way with me, but my mind inevitably drifts back to my ex. Ugh. I feel slightly worse now.
Noon Still feeling kind of down, so I’ve granted myself exactly one day this week to do absolutely nothing, and this is it.
3 p.m. I’m still hanging around the apartment snacking and reading and napping. A friend of mine calls these Piece-of-Shit days, and I think I deserve to have one on vacation.
5:30 p.m. Feeling a bit better now, so I bring a book, a sweater, and a blanket down to a beach not too far from where I’m staying. It’s chilly but beautiful. Still messaging “Italian,” and the conversation inevitably turns to sexting. (We’re messaging in Italian, but I studied here years ago so I know enough of the language to hold my own.) I’m down for a good flirty banter, but I can tell this guy wants to actually hook up and feel myself chickening out. I’ve been on a few dates since the breakup, but haven’t actually been intimate with anyone. Part of this trip was to help me “get back out there,” as I love vacation sex, but my gut tells me it’s not going to be with this guy.
7:30 p.m. Dinner for one at a little restaurant. My waitress gives me some great tips for places to check out over the next few days.
11:50 p.m. From Italian: “Where do you want me to come on you?” Yeahhhh, I’m out.
DAY THREE
9 a.m. Very excited to get up and out early for a spa day!
10 a.m. Checking in to this idyllic hotel that I definitely can’t afford, with yoga classes, spa treatments, and steam rooms.
1:30 p.m. Over a delicious meal, I fire up Feeld. This time I’m messaging with J, a British expat who’s living here now for work. He seems less horned up than the others, and he lives not too far from where I’m staying. Maybe I’ll actually see this one through?
3 p.m. While changing into my swimsuit in the women’s locker room, I take advantage of being alone in front of a full-length mirror to take some sexy pics to send to D, my most promising Feeld prospect back in New York. He’s another experiment to help me get out of my comfort zone: He’s an ENM married guy a few years my senior who I probably would have passed on if I had read the fine print. By the time I noticed the ENM thing on this profile, I had already developed a crush on him. I haven’t met him in person yet, but for whatever reason I find sexting with him to be incredibly fun and hot, so now I’m sending him a little vacation postcard.
6 p.m. Boooo. D hasn’t responded to my sexy pics!
10 p.m. At home, half a bottle of wine in, and I’m absolutely not leaving my apartment again tonight. Sorry, J!
DAY FOUR
9 a.m. Another day in paradise. Just lounging around.
11 a.m. More solo touring around in my little Fiat 500. This time I drive out to a little town for lunch and window-shopping.
3 p.m. I stop at another far-flung beach, and it turns out this one is topless if not fully nudist. It’s unusually warm out, so I hang there for a bit. Embracing a “when-in-Naples” mentality, I ditch my bikini top too.
7 p.m. Back in my flat, I spend some time reading the news and catching up on Twitter and email, but I really try to limit myself.
10 p.m. After a few hours of that, I put away my devices and go to sleep.
DAY FIVE
10 a.m. Last lazy morning in Naples. I’m puttering around, tidying up and getting ready to move out of my rented apartment and head out in time for my ferry to Capri.
Noon I grab some last souvenirs for friends and aggressively avoid the Feeld app on my phone. Sorry to the Neapolitan boys!
1 p.m. On the ferry, trying to ignore the butterflies in my stomach as I get ready to see my … friend? Lover? Here’s the deal with this guy: He’s Italian and lives in central Italy. We matched four years ago on a dating app in New York and went out for what was supposed to just be a one-night stand. He was in town on business for the weekend, I had just moved to the city, and we had a wonderful night drinking cocktails and speaking Italian and hooking up. He works for a multinational corporation, hence the travel to the States every so often. He’s not like, insanely wealthy where he’s flying me out to all these places. Nor is he a serial player who gets off on having a girlfriend in every major city. He’s just a nice, normal guy. I never expected to stay in touch after our first night in New York, but we did! We text fairly regularly and have seen each other a few more times since over the past few years, when I’ve been single, always on vacation, always just for a day or two. I can never decide if I actually have feelings for him or not.
4 p.m. I’ve checked in to our hotel in Capri and am waiting on the terrace for him to arrive. I reread the same paragraph of Didion like five times and suddenly … there he is! I’m genuinely so happy to see him again after so long. We head up to the room and get right to it. At first I’m so nervous my hands are shaking as I unbutton his shirt, but eventually I relax into the familiarity of him; how he smells, how his lips taste, how his hands feel on my body. It’s a quick romp and he comes on my boobs. I feel better now!
10:30 p.m. After a seaside dinner, the Lover and I are just walking around the city, bar-hopping and catching up. I’m so happy to be here in this place, next to this man.
2:20 a.m. We’re walking back to the hotel and … sneaking kisses and holding hands?! In some ways, this is way more intimate and unexpected than the sex we had earlier today. We’ve always had a clear attraction to one another, but up to this point we’ve sort of held back on being openly affectionate. This is really nice and sweet though.
2:30 a.m. Sloppy, romantic sex back at the hotel.
DAY SIX
8 a.m. I’m hungover as hell from last night but somehow find the strength to wake up for a yoga class at the hotel. I try to center myself and focus on my breathing, but keep smiling to myself having sexy flashbacks to last night.
9 a.m. Come back to the room to find a fresh-faced, shirtless Lover standing on the balcony taking a call. God, he is so beautiful. He’s already showered, so I quickly get ready so we can head out for a day of sightseeing.
1 p.m. Sharing a midday beer at a street-side café with Lover after walking around the central plaza all day. He’s been to Capri several times before and is a really great tour guide.
4 p.m. Chatting over drinks at our hotel, I lightly press at my one forever question for him, which is: Why is he still single? In the years I’ve known him, I’ve been preparing to one day be rebuffed when he meets some Italian beauty, but from everything he’s told me, he just prefers being a permanent bachelor. If anything, we had to put some distance between us last year when I was in my relationship in New York, which honestly made me sad. But I’m glad we’ve found our way back to one another.
8 p.m. After lounging by the hotel pool for a few hours, we head out locally in search of some dinner. It becomes clear to me that I really enjoy his company, not just his body. He makes me laugh, I like hearing about his family and his friends and his travels. Hmm, I can’t really afford to develop a full-on crush right now.
11:30 p.m. We’re back at the hotel and fucking. At first the lights are off, then when he’s behind me, he says, “I want to see, may I?” and turns on the lamp. Next thing I know, he’s in my ass! It’s not totally unexpected, as we’ve done anal before, and honestly he has a perfectly sized dick for it. I’m into it, he’s into it (and being able to see it, apparently), it’s superhot. He finishes and we go to sleep.
DAY SEVEN
9:30 a.m. We’re having breakfast at the hotel before he has to catch his ferry in a little bit. He’s heading back today, me tomorrow. I’m sad to see him go, so I feel a little melancholy at breakfast but peaceful.
10:45 a.m. Back in the hotel room, he’s packing up his things. We give each other eyes and it’s clear we want one last romp before he heads out, but the timing’s a little tight, so I just blow him quickly before he showers and heads out. I’m normally not the biggest fan of giving blow jobs, but I’m turned on by how much he’s enjoying this parting gift.
3 p.m. Back on the terrace by myself reflecting on the wonderful weekend.
5 p.m. I’m a little wine drunk, so I send him a sappy text saying I’m grateful he’s in my life, and he sends a sweet reply. And it’s true; I still don’t fully understand the extent of our relationship, but I’m glad to have it. We agreed he’d come to New York next time, though I don’t know when that’ll be.
9 p.m. One final dinner by myself at a local trattoria, eating pasta and sipping wine while watching the sunset (barf, I know, but it’s Italy!).
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Alyssa Shelasky , 2024-04-27 01:00:20
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