The lawyer who just wants a hot vacation affair

Illustration: by Marylu E. Herrera

This week a young lawyer has screaming orgasms at her beach cottage with a guy she met online: 30, single, Cape Cod.


9:15 a.m Actually, I’m on vacation, so I allow myself to sleep late. I’m renting a tiny house on the beach in Cape Cod. I’m turning 30 this week, so the trip is my gift to myself.

10:30 am I love and hate the fact that this place has no cell service. I have to walk down the street for a few minutes to get signal. I’ll take my coffee down the street and see what’s cooking in my inbox.

11 clock I am pleased to see that Oliver emailed me. He lives out here full time and we matched when I was scouting potential dates. We’re planning a cocktail at a beach cafe. Oliver looks too good to be true. I really wondered if he was a figment of my imagination or if he was married or otherwise going to disappear as soon as I arrived.

4 p.m I read and dozed on the deck. I am a lawyer working in finance and my normal life is extremely stressful. I have a lot of friends and a nice social life but honestly no time for dating. My last boyfriend was a few years ago. I ended up breaking up with him because everything was so boring. He was an adventurous lawyer with a low sex drive and a real mama’s boy. Sweet guy, but no thanks. Since then, there have been some drunk hookups and interesting online dates, but I haven’t had time to cultivate anything meaningful.

6 p.m When I drive to Oliver’s, I’m a little nervous. He looks really hot and sounds normal. It can’t be good.

19 o’clock He’s not that cute in real life, but that’s okay. Still, there’s something sad about him. Maybe he’s lonely. Part of me thinks I should keep drinking and then we can have a fun night and I’ll have a good story to tell. The other part thinks he’s probably not worth a hangover tomorrow.

21 clock i don’t feel it I tell him I’m going home because I’m tired. He looks particularly sad, which makes me even less in love with him. Maybe I’m a monster. But I’m really tired (and a little disappointed) and just want to go back to my tiny house and sleep.


8:30 am I’m angry with Oliver. I built it in my head and that’s on me. Back to the drawing board.

11:30 a.m I masturbate, which I do about once a day. Since I can’t get online, I close my eyes and think about fucking a (imaginary) hot surfer who rents a small house next to me.

14 o’clock Take me for a nice lunch in town. I’m really glad I don’t feel like shit today and kudos for ending the Oliver date early.

4:30 p.m I’m doing a pretty deep swipe session online. I still have three days here and would like to meet a few more men if possible.

17 o’clock Swim in the sea as the sun has calmed down a bit. Today was awesome!

19 o’clock I shower, go to bed naked, and start reading a new book. It really doesn’t get any better. I can hear waves from my window.


10:30 am I’ll take my coffee down the street to see if my stealing paid off. I met up with some cute boys. I’ll get straight to the point and tell the best prospects that I’m free tonight if they want a spicy margarita somewhere. First come, first served… I’m not saying that, but it’s my plan.

12:30 pm Oh, I almost forgot, today is my birthday. I’ve already celebrated my 30th in New York with friends and family. I’ll feel good when I turn 30. I like where I work. I’m comfortable with myself. I’d like to have a serious relationship soon, and if not, a few nights of rock star sex. I know I have to try harder to date, and this week is a fun kickstart for that.

3 pm I read my messages on the beach. There’s a guy named Tyler who’s here with his best friends from college. He lives in Boston and we have some things in common (similar work life, similar family life). We’ll pick a place to meet tonight. I have a very good feeling about him.

17 o’clock Tyler writes that his friends – two married couples – want to come tonight. Uhhh. I don’t need to make a fuss about it, but I’d rather not spend my birthday with shitty strangers I have to make small talk with. It also makes it seem a lot less like the first date. But I won’t say no! (I mean, can I say no?) I tell him I’m totally fine with it.

7:37 p.m I get there a bit late because it feels less awkward walking into their crowd than waiting alone at a big table for 5 people I have never met and who all live in Boston.

Tyler is hot. The friends are nice but a lot less edgy than all my NYC friends. Tyler and I do have chemistry though. My brain immediately tells me that I want to fuck him. The key comes through tonight.

8 p.m He’s sitting next to me and he’s already a little drunk. Not messy, but I can smell it on him. The way he snuggles up to me with his friends without any embarrassment makes me think he’s the group flirt who always has a new girlfriend. I shouldn’t be so quick to judge him, but I don’t want to be naive either.

21 clock They all tell funny college stories, and I’m like…um…. Haha.

9:30 p.m I decide to have a third margarita and fuck Tyler tonight.

10:30 p.m The friends roll home. Tyler wants to see my tiny house. I’m drunk. He is drunk. We decide to walk.

23 o’clock In my hut we tear each other’s clothes off. Tyler has a small dick, but he lunges at me like no one has ever done before. He turns me over and licks my ass and it’s heavenly. Before I come I tell him to put on a condom and we fuck like bunnies and have explosive orgasms. We probably woke up every tiny house in line, but I don’t care.

11:45 p.m I kick Tyler out and he kisses me on the lips before leaving. We’re both sweaty and salty, but the kiss is surprisingly sweet. I wouldn’t mind seeing this guy again.


9 am I hear my phone buzzing. I guess I suddenly have service? It’s Tyler checking how I’m feeling.

10 am I realize I never mentioned it was my birthday so I tell him he made me a great birthday night.

11 clock He’s shocked and insists on a proper birthday dinner tonight. I tell him I will allow it. Now that I’m sober, I’m less into Tyler than I was last night. But he’s very nice to texts and he rocked my world last night. We choose place and time. When he writes that his friends are coming, it becomes difficult.

19 o’clock We meet at a restaurant known for great seafood. Tyler looks really good. He has flowers for me as a belated birthday present.

9:30 p.m We share a bottle of white wine and obviously want to repeat last night, so we go straight back to my bungalow and start fooling around. The foreplay is overwhelming and I cum at least twice. I feel like I injected but he doesn’t mention it and I don’t ask.

23 o’clock My bed is too small for an overnight stay, so I’ll throw him out nicely. He’s leaving tomorrow, so we’ll meet up in New York. I’m happy with how our two-night affair went, but I’m not emotional that he’s leaving.


9 am I’m doing a spa day today as a birthday gift from my parents. Facial and massage await me.

4 p.m The spa was amazing. The only problem is that I’m so relaxed that I’m seriously concerned that I’ll fall asleep on the drive home. On the way out, I order a strong coffee from the small cafe in the lobby.

19 o’clock I’m all covered up and ready to get a good night’s sleep. I’ve barely checked my phone all day, but no texts to or from Tyler. It’s all ok!


13 o’clock As I drive back to New York, I smile to myself thinking about my screaming orgasms from Tyler. I definitely don’t regret it! It would have been nice if he was relationship material, but he isn’t.

4 p.m I’m at home in my apartment. I’m a bit exhausted from the drive, but I’m swiping on Tinder and Hinge and making some plans for tomorrow.

21 clock I start looking The bear. I’m very attracted to Jeremy Allen White who plays the main chef. I watch until I can’t keep my eyes open anymore.


10 am Classic Sunday brunch with a few friends. They’re all in relationships and I’m a little jealous of the stability. As a single woman, my vacation has made me feel both empowered and a little depressed. I tell everyone about Tyler. They all say I should give him a chance just because he’s cute and gives oral sex generously.

He writes after lunch. “Are you back in the big bad city? I’ll be there next weekend… bye?” I make a smack before texting him back.

3 pm I’m lying on my bed responding to some guys online. i really want a boyfriend Tyler was great and yes I will see him again but he probably won’t make it.

19 o’clock I take out my vibrator. I close my eyes and imagine being back in my beach cottage. This time a local chef comes over after his shift and fucks me until the little house shakes. I told you I enjoy it The bear!

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