HomeTravelsThe lawyer who just wants a hot vacation

The lawyer who just wants a hot vacation

Illustration: by Marylu E. Herrera

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

DAY ONE

9:15 a.m. I’m technically on vacation, so I’m allowing myself to sleep late. I rent a small house near the beach in Cape Cod. I turn 30 this week, so travel is my gift to myself.

10:30 a.m. I love and hate that this place has no cell service. I have to walk a few minutes down the road to get a reception. I grab my coffee on the road and check out what’s cooking in my inbox.

11 a.m. I’m glad to see that Oliver emailed me. He lives here full time and we hit it off when I was lining up potential dates. We plan to have a cocktail at a beach cafe. Oliver looks too good to be true. I really wondered if he was a figment of my imagination, if he was married or if he was going to disappear as soon as I arrived.

4 p.m. I read and dozed on the deck. I am a lawyer who works in finance and my normal life is extremely stressful. I have lots of friends and a great social life, but honestly, I don’t have time to hang out. My last boyfriend was a few years ago. I ended up breaking up with him because it was so boring. He was an unadventurous lawyer with a low libido and a real mama’s boy. Honey, but no thank you. Since then, there have been some interesting drunken encounters and online dates, but I haven’t had time to cultivate anything meaningful.

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

7 p.m. He’s not as cute in real life, but that’s okay. There is still something sad about him. Maybe he’s alone. Part of me thinks I should keep drinking and then we can have a good night and I’ll have a good story to tell. The other part thinks he’s probably not worth the hangover tomorrow.

9 p.m. I do not feel it. I tell him I’m going home because I’m tired. He looks very sad, which makes me even less in love with him. I may be a monster. But I’m really tired (and a bit disappointed) and just want to go back to my little house and sleep.

DAY TWO

8:30 am I’m disgusted with Oliver. I built it in my head, and it’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 connect, I close my eyes and think about fucking a sexy (imaginary) surfer who rents a little house next to me.

2 p.m. I invite myself to a good lunch in town. I’m really glad I didn’t feel like shit today and I’m glad I ended the date with Oliver early.

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

5 p.m. Swim in the ocean since the sun has calmed down a bit. Today was hot!

7 p.m. I take a shower, go to bed naked and start reading a new book. It really doesn’t get any better than that. I hear the waves from my window.

DAY THREE

10:30 a.m. I take my coffee on the street to see if any of my moves have paid off. I matched with some cute guys. I’m going straight to the point and telling the best prospects I’ve got a free night tonight if they want to grab a spicy margarita somewhere. First come, first served… I’m not saying that, but that’s my plan.

12:30 p.m. Oh, I almost forgot, it’s my birthday today. I already celebrated my 30th birthday in New York with my friends and family. I feel good about turning 30. I like where I am professionally. I am comfortable with myself. I’d like a serious relationship soon, and if not, a few rock star nights. I know I have to try harder to date someone, and this week is a good start for that.

3 p.m. 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 things in common (similar professional life, similar family life). We choose a place to meet tonight. I have a very good feeling with him.

5 p.m. Tyler texts that his friends – two married couples – want to come over tonight. Ughhh. I don’t need to make a fuss about it, but I’d rather not spend my birthday with shitty strangers to chat with. It also makes it seem a lot less first date. But I’m not going to say no! (I mean, can I say no?) I tell her it looks perfect on me.

7:37 p.m. I get there a little late because walking through their crowd is less inconvenient than waiting alone at a large table for 5 people I’ve never met who all live in Boston.

Tyler is HOT. The friends are nice, but a lot less pissed off than all my friends in New York. Tyler and I have chemistry. My brain immediately tells me that I want to fuck him. The key goes tonight.

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

9 p.m. They all tell funny stories in college, and I’m like…uh…. Haha.

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

10:30 p.m. Friends go home. Tyler asks to see my little house. I’m drunk. He is drunk. We decide to walk.

11 p.m. At home, we tear off clothes. Tyler has a small dick, but he falls on me like no one else has. He turns me around and licks my ass, and it’s divine. Before cumming, I tell her to put on a condom and we fuck like rabbits and have explosive orgasms. We probably woke up every little house in the row, but I choose not to care.

11:45 p.m. I fire Tyler 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.

DAY FOUR

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

10am I realize that I never mentioned it was my birthday, so I tell him that he gave me a great birthday party.

11 a.m. He is shocked and insists on a real birthday dinner tonight. I tell him that I will allow it. Now that I’m sober, I’m less of a Tyler fan than I was last night. But he’s very good at texting, and he turned my world upside down last night. We choose a place and a time. If he’s texting that his friends are coming, it’s going to be a rough patch.

7 p.m. We meet at a restaurant famous for its excellent seafood. Tyler is really handsome. He has flowers for me as a belated birthday present.

9:30 p.m. We shared a bottle of white wine and clearly want to repeat last night, so we head straight back to my bungalow and start having fun. The foreplay is amazing and I come at least twice. I feel like I squirted, but he doesn’t talk about it and I don’t ask.

11 p.m. My bed is too small for a slumber party so I kindly kick it out. He leaves tomorrow so we plan to meet in New York. I’m happy with how our two-night adventure went, but I don’t feel any emotion at his departure.

DAY FIVE

9 am I’m doing a spa day today as a birthday present from my parents. Facial treatment and massage are waiting for me.

4 p.m. The spa was amazing. The only problem is that I’m so relaxed that I honestly dread falling asleep on the way home. When I leave, I order a strong coffee from the small cafe in the lobby.

7 p.m. I’m settled in and ready for a good night’s sleep. I barely checked my phone all day, but no texts to or from Tyler. All good!

DAY 6

1 p.m. As I drive back to New York, I smile thinking of my screaming orgasms from Tyler. I really don’t regret them! It would have been nice if it was relational material, but it isn’t.

4 p.m. I am at home in my apartment. I’m a little reader-worn, but I’m gliding through Tinder and Hinge and making plans for tomorrow.

9 p.m. I start watching the bear. I’m very attracted to Jeremy Allen White, who plays the lead chef. I watch until I can’t keep my eyes open.

DAY SEVEN

10am Classic Sunday brunch with a few friends. They’re all a couple, and I’m feeling a little jealous of the stability. As a single woman, my vacation left me feeling both empowered and a bit depressed. I tell everyone about Tyler. They all say I should give him a chance just because he’s cute and gives a generous blowjob.

He’s texting after lunch. “Are you back in the big, bad town?” I’ll be there next weekend… See you? I take a moment before answering him.

3 p.m. Lying on my bed, I respond to guys online. I really want a boyfriend. Tyler was awesome, and yes, I will see him again, but he’s probably not going to cut it.

7 p.m. I take out my vibrator. Closing my eyes, I imagine being back in my beach cottage. This time a local chef comes after his service and fucks me until the little house shakes. I told you that I appreciate the bear!

Want to submit a sex diary? E-mail sexdiaries@nymag.com and tell us a bit about yourself (and read our submission conditions here.)

Must Read