u/undergivnajohan

Having worked sixty-hour weeks for the past six months ever since graduation had taken its toll, tired and run down, I was looking forward to my first long weekend. I scrolled through the internet for any sort of chance to escape the city and the looming presence work seemed to have even on those rare moments of free time. Too expensive, too long, too boring, one option after the next fell for one of a thousand reasons. As time ticked on, the only even remotely reasonable choice seemed to be a cruise with an age limit of 30. Maybe a couple of blackouts was just what I needed. A credit card later, and I had the ticket in my email.

Two days later, I had a weekend bag slung over my shoulder, two shots coursing through my blood, and the sea water was washing away every last care and worry the city held as the queue to get onto the boat moved like molasses, slowly one step closer. Eventually, I made it to the top and showed my ticket to the attendant.

"Johan, is that you?"

The words sent a chill down my spine. I wasn't supposed to know anyone here. This was just going to be a chill weekend.

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A cruise with a simple rule: men under 30, women over 40. And I just ran into the one person I never expected to see here,my former teacher/boss.

TLDR: A guy sneaks into his crush's room during her son's party, plants files containing his own blackmail material onto her computer.

The air is warm, almost too warm as we celebrate Caleb, your son and my best friend for most of my life. We had always been inseparable during our time together, until my parents decided their perfect genius needed a better start and forced me to go to a stuffy private school. It did wonders for my grades, I even graduated early, but I would have rather spent those years with him, my best friend, and with you, my crush for years now. But as it always did, different schools meant less time together, and soon enough we were drifting apart. The one thing that never changed, however, was my feelings for you, Caleb's mother.

Having excused myself to use the bathroom, fueled by my first tastes of alcohol, I snuck back into your house. The laughs and happy voices from the party grew quieter as I ventured deeper, down a hall, up a staircase. Halfway up, I froze, questioning myself as I had countless times whether this was really a good idea. The little USB stick in my pocket felt like it was burning against my thigh as my pulse quickened. Closing my eyes, I took a couple deep breaths, remembering my favorite quote: "Life without risk is more bland than oatmeal." With steely resolve, I pushed through, making my way the last few steps until I saw your bedroom. The door was closed, of course, no one should be up here.

Each step made my heart beat harder. As I reached for the handle, the sounds of the party downstairs were all but gone, hidden behind the pounding of my own heart. Pushing down the handle and letting the door swing open, I was met with a wall of your scent. My knees went weak, and I had to reach for the door frame to keep from falling. Each subsequent breath breathed more and more strength into me, as you always have, until within half a minute I was back to full strength. I took a few careful steps to make sure my knees would hold my weight as I made my way inside your room, heading straight for your computer. Pulling the tiny USB from my pocket, my fingers trembled so badly it took me a second try to get it out. I prayed as I pushed it into your computer that you still had the same password as years ago. My hands shaking made it hard and time-consuming to type, but eventually I got it right. My heart skipped a beat as I pressed enter and it started to load. Each second before confirming the password was valid felt like a lifetime, but finally the computer screen lit up, I was in. A couple clicks of the mouse later, and the files I had prepared on the USB were on your computer. Pulling the USB from the computer, I swallowed as some sort of finality washed over me, calming my nerves for the first time in weeks. All the blackmail material on me was now on your computer.

With steps light as a feather, I walked around your bed and headed for your door, stopping mid-step as I saw your hamper. My pulse quickened again, back to thumping in my ears. Reaching out, I lifted the lid, revealing your dirty clothes. Leaning my head out the door, I tried to listen for anyone in the house, but all I could hear was my heart. I couldn't see anyone, and so with one final moment of bravery, I reached down and grabbed a pair of your panties. Telling myself it was a fair trade for all the blackmail you now had on me.

With only a couple of regulars still left by eleven in the evening, I rang the bell, signaling it was the last call of the night. I filled a couple of glasses, and everything seemed fine as they took it in stride. Everyone, that is, except a booth overflowing with middle-aged women doing what they could to make the night last longer. Sitting among them was my mother, who just so happened to own this little bar. Even as I closed the doors behind the last of the regular crowd, I knew my night was far from over.

My mother's best friend from college had finalized her divorce earlier today, and as had become tradition, all the sorority sisters who still lived in the same town came together to celebrate her freedom, something of a regular occurrence around this place as of late. In the past three years, this had happened four times already; it seemed that the men they had picked couldn't quite keep up in the long run.

Making my way behind the bar, I grabbed a couple of bottles. Looking up, I tried to gauge what level of drunk this night was headed towards. Looking down at the two bottles of red, I sighed, knowing bringing them would just have me taking two trips to bring tequila instead. Swapping them out, I put on my best smile as I walked the short distance to the table, placing the two bottles in the middle, only to be met with some very loud "Whooooing." I fished my phone out from my pocket and pulled up Spotify, handing it over to the divorcee. "Your choice of music tonight!" I said with a smile.

Hours later, I was woken by the sound of my phone ringing. Eventually, I got my bearings and tried reaching for it, only to find my arms tied to the headboard of my bed and a warm body cuddled up next to me. I sighed, annoyed I couldn't answer, figuring I had a bit too much to drink last night and that the woman next to me was my girlfriend. Extending my neck to try and see who was calling, a chill ran down my back as I saw the name: "Babe <3." Not my choice for a contact name....

With only a couple of regulars still left by eleven in the evening, I rang the bell, signaling it was the last call of the night. I filled a couple of glasses, and everything seemed fine as they took it in stride. Everyone, that is, except a booth overflowing with middle-aged women doing what they could to make the night last longer. Sitting among them was my mother, who just so happened to own this little bar. Even as I closed the doors behind the last of the regular crowd, I knew my night was far from over.

My mother's best friend from college had finalized her divorce earlier today, and as had become tradition, all the sorority sisters who still lived in the same town came together to celebrate her freedom, something of a regular occurrence around this place as of late. In the past three years, this had happened four times already; it seemed that the men they had picked couldn't quite keep up in the long run.

Making my way behind the bar, I grabbed a couple of bottles. Looking up, I tried to gauge what level of drunk this night was headed towards. Looking down at the two bottles of red, I sighed, knowing bringing them would just have me taking two trips to bring tequila instead. Swapping them out, I put on my best smile as I walked the short distance to the table, placing the two bottles in the middle, only to be met with some very loud "Whooooing." I fished my phone out from my pocket and pulled up Spotify, handing it over to the divorcee. "Your choice of music tonight!" I said with a smile.

Hours later, I was woken by the sound of my phone ringing. Eventually, I got my bearings and tried reaching for it, only to find my arms tied to the headboard of my bed and a warm body cuddled up next to me. I sighed, annoyed I couldn't answer, figuring I had a bit too much to drink last night and that the woman next to me was my girlfriend. Extending my neck to try and see who was calling, a chill ran down my back as I saw the name: "Babe <3." Not my choice for a contact name....

With only a couple of regulars still left by eleven in the evening, I rang the bell, signaling it was the last call of the night. I filled a couple of glasses, and everything seemed fine as they took it in stride. Everyone, that is, except a booth overflowing with middle-aged women doing what they could to make the night last longer. Sitting among them was my mother, who just so happened to own this little bar. Even as I closed the doors behind the last of the regular crowd, I knew my night was far from over.

My mother's best friend from college had finalized her divorce earlier today, and as had become tradition, all the sorority sisters who still lived in the same town came together to celebrate her freedom, something of a regular occurrence around this place as of late. In the past three years, this had happened four times already; it seemed that the men they had picked couldn't quite keep up in the long run.

Making my way behind the bar, I grabbed a couple of bottles. Looking up, I tried to gauge what level of drunk this night was headed towards. Looking down at the two bottles of red, I sighed, knowing bringing them would just have me taking two trips to bring tequila instead. Swapping them out, I put on my best smile as I walked the short distance to the table, placing the two bottles in the middle, only to be met with some very loud "Whooooing." I fished my phone out from my pocket and pulled up Spotify, handing it over to the divorcee. "Your choice of music tonight!" I said with a smile.

Hours later, I was woken by the sound of my phone ringing. Eventually, I got my bearings and tried reaching for it, only to find my arms tied to the headboard of my bed and a warm body cuddled up next to me. I sighed, annoyed I couldn't answer, figuring I had a bit too much to drink last night and that the woman next to me was my girlfriend. Extending my neck to try and see who was calling, a chill ran down my back as I saw the name: "Babe <3." Not my choice for a contact name....