In this week’s story, a woman has a wild one-night stand in her Porto hotel room: 44, single, Portugal.
DAY ONE
7 a.m. Land in Lisbon after taking a red-eye from New York. I get my luggage and hail a cab. This trip is all about clocking some solid “me” time. I’ve been divorced for several years now — it was a toxic relationship with an addict — and it did a number on me. I date a little here and there, and have casual sex on occasion, but as cheesy as it sounds, I’m really in a deep and loving relationship with myself right now.
10 a.m. Finally arrive at the hotel, ready to take a long shower, get into my bathrobe, and have a siesta. But I can’t check in until 3 p.m. Shit. How did I not think of that? I leave my bags at the hotel and head out. I take myself on a little walking tour of the area, but I’m dying for my room at this point.
2 p.m. The room still isn’t ready, so I go to a café to eat pastel de nata — it’s like a custard cup. Whatever. I’m feeling ultradisgusting now, and I don’t even think it’s that great. Everyone around me is in groups. I love solo travel and normally it doesn’t make me feel insecure at all — empowered if anything — but right now I’m just feeling out of sorts.
3 p.m. The hotel texts that my room is ready. I literally run there and immediately hop in a shower.
6 p.m. I’ve pre-signed up for a food tour. I get there and it’s all Americans. They’re like the cast of Grey’s Anatomy, all recent med-school grads. There is one hot doctor with them, who is actually in his 30s.
8 p.m. We’re on a walking break. The hot doctor makes a beeline for me. I’m thinking, “I manifested this to happen.” I knew there would be romantic and sexual adventures on this trip. I’m not searching for them, but I’m open to them. He’s making small talk with me. I’m feeling giddy because he’s cute and nervously flirting with me. The walking tour continues. He’s hanging out near me now. This is exactly how I wanted to start my trip!
10 p.m. I end up tagging along with the doctors. We all go to a bar. The cute doctor and I are getting a little cozy. We’re trying each other’s cocktails and talking a lot.
11 p.m. We end up sharing a big Uber van since they’re all staying near me. The hot doctor and I sit in the back of the car. He leans over and kisses me. It feels so high school and I love it. I’m like “Can I have another?” It’s cute. It’s apparent that he’s going back with his group, as they get dropped off first, but he asks me to text him that I’m back in my room safe and sound.
11:45 p.m. We text a little about how fun that was. I knew tonight wasn’t going to end up with anything wild, but it got me off on the right foot.
DAY TWO
9 a.m. Wake up and feel very happy that I’ve opted in for the free breakfast. While eating, I take inventory of my life. Only last year I opened a hair salon. I just moved to a new, better location. I’m growing and expanding my business. In New York, I work 12-hour days, five days a week. All I do is work and watch Love Island. And now here I am taking a three-and-a-half-week trip around Europe. I become a new person when I’m on vacation because I am literally so stress-free.
1 p.m. I just want to walk around and get to know Lisbon today. I do a little shopping.
3 p.m. I’m thinking about texting the hot doctor, but I also like the way it ended. I decide to leave it at that. Instead, I make plans to go out tonight. I go on Tripadvisor and buy a ticket for a bar crawl.
5 p.m. I rest a little. I try to read It Ends With Us, which I want to finish before seeing the movie.
10 p.m. The bar crawl starts. Everyone is 20 years old. I tell them all that I’m 44. I’m older than everybody combined. Most of them are from New Zealand and we’re all hanging out. I love TikTok, so I’m like, this is the perfect time to do the apple dance. I mean, the best way to bond is to do a viral dance, right? After that, I drink a bunch of disgusting sangria, pull an Irish exit, and get myself home.
DAY THREE
10 a.m. Breakfast like a queen.
11 a.m. Looking up the location of this baking class I signed up for today. It’s walkable from my hotel, which I love. I decide to take it easy in my room until then.
2 p.m. I’m at the baking class. The gorgeous teacher ends up being my partner, since per usual I am the only one here alone. I can cook, but I can’t bake for shit. My pastry, however, comes out the best because my partner is the fucking teacher! It’s really fun.
5 p.m. Back at the hotel getting ready for my night out. I have a blind friend date with a gay and fabulous cousin of a friend. I am trying to convince him to meet me at the fanciest place in Lisbon. Once I tell him I’ll treat, he’s sold.
7 p.m. This guy is as fabulous as I dreamed he would be. He’s also Colombian and I speak Spanish, so it’s nice not to have to use Google Translate to communicate in Portuguese. We have dinner: beef carpaccio and chicken croquetas. We take a lot of selfies.
9 p.m. We go to a bar nearby. Eventually, I tell him about my love life back home — how I got divorced and really went through it; my ex was an addict who recently passed away. I explain how I’ve spent the last year getting to know me and what I want — even if it’s just sex right now, I want it to be meaningful, pleasurable sex.
11 p.m. He asks if I want him to read my tarot cards? I do. The cards tell him I’m in the best place in my life and that an epic adventure is coming my way. What a great way to end my last night in Lisbon.
DAY FOUR
10 a.m. Take the train from Lisbon south to Estômbar-Lagoa, on the coast. I love taking the train.
1 p.m. Check in to the most glorious hotel. They let me into my room right away, so of course I’m thrilled about that. I take a nice nap.
2 p.m. I go downstairs and order a mojito. I still have the damn book but don’t even read a page. The drink kicks in and I’m thinking that I want to amp up the adventure and explore another town.
3 p.m. I hop in an Uber to Albufeira, a town I know very little about but heard was fun and coastal. I’m blasting “I came here for love!” from Love Island in the Uber.
4 p.m. I’m horrified when I arrive. It’s the Cancun of Portugal. I’m in hell. I’m surrounded by bars with drunk people everywhere, bad music, everyone is here from the U.K. looking to party and plastered. It’s spring break on steroids. I take a million videos to remember how bad it is.
6 p.m. I can’t find any good food, so I get pizza. It’s tragic eating such shitty pizza in a place like Portugal! I call myself an Uber back to the hotel and decide to start fresh tomorrow.
9 p.m. Close my eyes, blissed out in my 5-star hotel, and go to bed.
DAY FIVE
9 a.m. I’m taking myself on a boat ride today. I feel very luxurious doing this.
11 a.m. The people who manage the sailboat are a lovely, older Portuguese couple. I like them immediately. We hook up the Bluetooth so I can play my music.
1 p.m. I am loving these people. It’s like they are the main characters in the movie that is my life today.
2 p.m. I ask them about their secret to happiness. I also ask them for advice on how or where I should find love, if that’s what I even want? We get pretty deep into it.
4 p.m. It’s time to dock the boat. We talk about how I wish I saw the sunset and they invite me on their own private boat later tonight. I’m so touched by this.
8 p.m. I’m on their boat. We see the sunset. We take a million pictures of each other. I feel a friendship love story with them that reminds me not all love stories have to involve men or sex. I eventually go back to the hotel to sleep knowing I have an early morning heading to the airport to fly back up north to Porto.
10 p.m. I schedule the Uber for the morning, which I didn’t know you could do. Someone named Gabriel confirms.
DAY SIX
8 a.m. Last wonderful breakfast here.
10 a.m. Gabriel pulls up. All six feet and five inches of him gets out of the car. The way he handles my embarrassingly enormous luggage, which has a huge orange tag that reads “Heavy” on it, and tosses it in the back seat, turns me on profoundly. He speaks zero English. I speak zero Portuguese.
10:30 a.m. I’m in the backseat. He tells me — all via Google Translate on my phone — that he likes my face. It’s very early for me to start flirting this heavily. I tell him I like his face too. He says, “I want to know you!” He’s telling me he wishes I wasn’t going to the airport. By now, I have already made up my mind that he is the epic adventure from the tarot cards.
11 a.m. He tells me that I’m early for my flight, but I always get there early in case I have to fight with the airline about my heavy bag. He asks if he can take me to a beach by the airport for five minutes so we can talk and get to know each other. I tell him that if I miss my flight, he’ll have to drive me the five hours to Porto. Then I have an idea. “Actually, are you up for an adventure?” He says, “Yes.” I say, “You’re driving me to Porto.” The flight was cheap. Whatever.
I get into the front seat. He sticks out his hand and says, “Gabriel.” I give him my name. He says in very broken English, “Nice to meet you.” Out of a movie, he kisses me. It’s obvious to both of us that he’s coming to Porto to hang out with me as a lover, not an Uber driver.
11:30 a.m. He makes a quick detour to his apartment and gets fresh clothes to change into in Porto. On the way there, I call my one Brazilian friend who lives in Norway, and I make my Brazilian friend talk to Gabriel on the phone in Portuguese. I make sure my friend approves. He says, “He’s a nice guy. He’s not sketchy. He’s studying for his master’s degree; just have fun.” So it wasn’t entirely irresponsible … Gabriel also gave my friend his information, phone number, Instagram account, etc. I feel more safe now, though I never felt unsafe with him.
3 p.m. We’re driving. We’re holding hands a little bit. I’m horny. We’re talking about all our favorite positions. It’s all through Google Translate. Sexual tension is through the roof. I’m telling him “I’m insatiable.” He’s telling me he’s hard.
3:30 p.m. We get gas. I buy him a chocolate bar. It’s romantic.
4 p.m. We get to Porto. I tell him to valet his car. He’s never valeted a car before! It’s adorable. I’m kind of acting like a sugar mama. I’m like, “I’ll treat. Who cares?” The hotel room is sick. It’s the nicest room I’ve ever stayed in. I’m flabbergasted but trying to be like, “This is my life, welcome.” The first thing he does is shower. He comes out of the bathroom smelling like my favorite Byredo scent — it’s a miracle that that’s the soap they have at the hotel. Like, what are the chances? We start getting down to it. It’s really fun. His dick is huge. He goes down on me, we fuck, I have a couple orgasms. It’s really, really good sex.
6 p.m. He’s still hard. He’s throwing me around the room. It’s insanely wild. But I need to stop. There is only so much I can handle. I’m like, “Are you close?” He’s like, “Not even.” I tell him we need to pause. I need a break! He’s very cool about it.
8 p.m. I shower and put on a pretty dress for dinner. He takes a new outfit out of his bag and the clothes still have their tags on. It makes me feel really good that he was waiting for a special occasion to wear those clothes, and I was the special occasion.
8:30 p.m. We take some pictures. He’s so much taller than me! Then we go to a Brazilian steakhouse. This man can consume endless amounts of meat! I’m basking in all of this.
10 p.m. After dinner, he tells me he’s turned his Uber back on to make some money for his drive back. We take a nice stroll first. He walks me to the hotel. And then he leaves! I’m honestly so excited that he’s leaving. I couldn’t do a round two of that sex with that massive dick. And I really wanted to sleep in my nice hotel bed by myself. The entire day could not have been more perfect. We said we’d keep in touch, obviously.
DAY SEVEN
9 a.m. I wake up at my leisure and text Gabriel to make sure he got back okay. We have some cute banter.
10 a.m. Gabriel sends me a list of everywhere I have to go in Porto, a full itinerary. It’s so sweet. Where to grab a beer, where to sit by the river, where to watch the sunset.
2 p.m. I get lost in the streets following his list. I’m feeling elated. It’s only day seven of this long trip but I’ve already had the exact adventure I wanted.
3 p.m. I’m texting my best friends in New York about how I slept with my Uber driver. I knew no one would believe me, so I’m glad I have the pictures to show it.
5 p.m. I get a text from Uber for over 350 euro. I text Gabriel, “What the fuck is this?” He’s like, “Oh no!” He didn’t properly shut down Uber for the drive. He tells me how to fight it. He feels really bad. Uber immediately refunds the money. Crisis averted!
9 p.m. I’m lying in bed replaying last night’s sex. I think I might never tell a man “I’m insatiable” again. Careful what you wish for! I mean, this man had the penis of a mammoth and I have the body of a tiny woman. Still, the sex was animalistic but never rough. It didn’t give me a moral hangover. It all made me feel really good. Needless to say, he gets a five-star rating.
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