I Slept With My Ex’s Brother

You guys... Just, woah. I left his place a few hours ago, and I’m just lying in my bed writing it all down to clear my mind. So here it goes...

12 years ago, I was 18 and started dating this guy I met while we were working at a summer camp. We were both hired as counselors and started a sweet summer fling that slowly fizzled out once we went home. We were each other’s first real relationship. We met each other’s families and friends. But we lived in different towns about 2 hours away, and when we started attending colleges that were even further away, we mutually decided to call it quits after 5 months. We never had sex, though other acts were performed. He moved on almost immediately. He had a new girlfriend within a few weeks, and they ended up getting married and now have two boys together.

I had met his older brother while my ex and I were dating. I thought his brother was very attractive but didn’t think of him romantically. He was 28 at the time, recently passed his bar exam, and beginning his career as a lawyer. I liked talking to him, but he was just my boyfriend’s brother... Again, I was 18 and hadn’t even started college yet when we met. I was very immature, and he seemed like a full blown adult in comparison. He was NOT on my radar.

Fast forward to 2019, I broke up with my longtime boyfriend of 8 years in April after discovering I had been cheated on multiple times. After learning the depths of his infidelity, I felt disgusting. He made me feel like a piece of trash that would never be enough. I felt boring, ugly, undesirable... If there was a negative emotion you could have about yourself, I felt it.

I moved out of our shared apartment and found a little downtown studio just for me. My first time living on my own. I posted a photo on Facebook of me in my new place sipping champagne on my balcony. Soon after, out of the blue the brother of my ex from 12 years ago sends me a DM.

”Welcome to the neighborhood,” he wrote. By happenstance, I moved in about a mile away from him. We casually catch up and swap messages over the next few months.

Then... this past week, he asks me out for drinks. I’m a little surprised, a little flattered, a little confused, and a little excited. We make plans to meet at a bar about halfway between our places.

I hadn’t dated anyone since the break up in April. I made a few ill-fated attempts at dating apps, but I didn’t enjoy it. Tinder was one of the ways my boyfriend found other women... kinda hard for me to use it after that.

Friday night rolls around, and I walk to the bar on a breezy summer night. With the meeting place in sight, I recognize him from afar, waiting for me outside. He’s dressed impeccably sharp. Much taller than I remember. Five o’clock shadow. Bright blue eyes. Inviting grin. He has aged, but the years make him look masculine and self-assured.

We greet with a hug, exchange pleasantries, and head inside. We settle into a pair of stools on the far end of the room.

I like him more with every word that comes out of his mouth. He’s smart, funny, sweet, driven... I push the whole “I DATED YOUR BROTHER” thing out of my mind... Right now, I am deaf to any arguments that would tell me not to continue down this path.

After a few hours, a few drinks, a few casual touches, and a few flirtations, we settle the tab and make plans to go to a nearby karaoke bar. I can’t tell if it’s first date excitement, 3 glasses of Pinot Grigio, or a summer night stroll in the city, but it’s all very intoxicating.

As we’re walking, I’m telling him a story when he casually reaches for my hand. I completely lose my train of thought. I stop talking mid-sentence, then stutter, then apologize for stuttering. He breaks the tension with a warm laugh. I have to laugh at myself as well.

He stops walking, and gently pulls my hand so my body will turn to his. He leans in and kisses me. Fireworks. Trumpets. Audience woo’s. Its all happening.

The kiss gets deeper. His touch stronger. The wine has gone to my head, and I say to him, “How far are we from your place?” (LIKE WHAT AM I EVEN SAYING?! WHO IS THIS WOMAN?! This is new territory for me!) He kisses me again, then says resting his forehead on mine, “Really close...”

We get to his building, and I’m immediately taken aback with how nice it is. We take the elevator to one of the top floors. He opens the front door, and it’s breathtaking. Floor to ceiling windows with stunning views. He pours me a drink while I stare at the city below trying to spot familiar landmarks.

We briefly continue the conversations we’ve carried on throughout the night. Me on the couch and him on a chair across the room. My glass is almost empty when he gets up to sit next to me.

I decide to make the next move. Setting what’s left of my drink down on the coffee table then leaning into him as my lips find his. It’s an intimate kiss. Soft lips and gentle tongue. After a minute, I feel him start to guide my hips to the end of the couch. His hands move under my dress, slowly taking off my panties. Our lips part. He pauses to kiss my neck, then my chest, then my stomach, and then... well... lines get crossed. Business eventually moves to the bedroom, and things are officially complicated.

The whole night was amazing. Really amazing. He was handing out orgasms left and right. I fell asleep next to him and woke up to another round. Afterwards, he asked me to stay, but I needed a minute to myself to process what happened.

Is this a one night stand? Rebound sex? Or the start of something? Something what... something inappropriate? Something good? I’m not pretending to know any of these answers. And maybe, it’d be easier to just vanish before they could be revealed.

So here I am... hours later... re-playing in my head the mindblowing sex I had with this fantastic man who happens to be my ex-boyfriend’s older brother... Lord help me.