Hotel sex and unexpected hook-ups weren’t on my mind when I was packing for this trip, but that is what happened. I always expect work trips to be boring. The last thing I expected was a hot hook-up with a co-worker in my dark hotel room.
As a freelancer, I’m rarely included in corporate work trips. So when my client invited me to their annual marketing team off site, I jumped at the chance. After years of being a remote freelancer, I was excited to meet some of the people I have been working with in person, and let’s be honest, I was not going to say no to a free vacation.
When I arrived in Wyoming, I was pleasantly shocked to discover that the company had rented an entire resort for us and given me my own two-bedroom condo on the grounds.
Once I got settled into my room, I headed to the hotel conference room for a meet and greet cocktail hour with my co-workers. Since this was my first time meeting most of these people in person, I decided that I was going to go into it cute, comfortable and professional. I slid into a pair of fitted jeans, with a black button up shirt and a pair of cowgirl boots to keep the western vibe of the resort.
After the meet and greet, a lot of people were tired from traveling and went back to their rooms for the night. I wasn’t tired just yet. So I decided to decompress for the day at the bar.
I was just starting my second drink for the night when I heard a man’s voice behind me say “Do you mind if I join you, Katrina?” I turned around to see Connor standing behind me. It was all that I could do to keep from rolling my eyes. I had worked with Conner on a few projects since freelancing with this company and he was the biggest asshole I had ever run across. He is a know it all, and clearly has no respect for women in the workplace.
Ever the professional, I managed to stifle the urge to roll my eyes and tell Conner to fuck off. Instead I managed to give Conner a smile and invited him to join me. At this point in the evening, hotel sex and hook ups were the furthest thing from my mind.
By our third or fourth round of drinks, I had begun to soften on Conner. In person he was funny, and charming. We commiserated about some shared pet-peeves about work, and learned that we have a lot more in common than I thought.
As we talked, I noticed that Conner is pretty hot. He’s tall, well over six feet. With dark brown hair, and his casual corporate style hid his full sleeve of tattoos on his right arm. We started this conversation on opposite sides of the table. Like opposing heads of state preparing for negations. But now, we are sitting next to each other shoulder to shoulder.
I could feel Conner’s hand on my knee slowly working his way up my thigh as we laughed and talked. My hand landing on his hard chest after a few of his deadpan style zingers.
At some point I looked around the bar. The music that had been a steady hum to the evening had been turned off. The bartender was wiping down the counter, and I saw a bar back making his final rounds. All signs that the bar was getting ready to close. I looked at my phone, it was almost 2 am.
“Christ”, I said. “didn’t realize that it was this late. Conner stretched his long legs out in front of him as he leaned back in his chair. “See,” Conner said, “I’m not too bad once you give me a chance.” I rolled my eyes and smiled.
Looking outside of the lobby windows it was dark. The kind of pitch black eerie dark that you only get in the middle of nowhere. “Where are you staying?” I asked. Conner nodded towards the darkness. “I’m on the other side of the property, near the cabins.” I shuddered. “That is a long walk in the dark.” Conner laugh, a slow grin spreading across his face. “One more drink?” he asked. “Sure,” I nodded, “one more drink”. I should have known from that moment that we were walking down the path of a hotel sex and a corporate hook up.
For a second, I thought about just letting go on his way. The chemistry between me and Conner was real. But he is married, with three little kids at home. But, I was four drinks into the night. And the thought of making him stumble back to his cabin on the other side of the property felt unnecessarily dramatic. This wasn’t going to be a hotel sex hook up. This was me being kind and giving a drunk co-worker a safe place to land.
I let out an exhale, and grabbed my bag and pushed myself away from the table. My condo is closer. You can crash there. Conner raised his eye brow. “Settle down, cowboy”, I laughed. “They gave me a two bedroom condo. You can crash in the guest room tonight. Better than you getting lost in the woods trying to find your room in the dark.
“So, is this the part where I find out that you’re a serial killer who lures co-workers out to the woods?” Conner asked. I laughed. “Dude, you were the one who suggested another drink.” Conner smiled. “I’m pretty sure that you just invited me back to your place.”. I stopped, and turned to face Conner. Looking up at his handsome face and looking him square in the eye as I said, “No, I offered you safe lodging for the night. If you wind up dead wondering the woods in the middle of the night, I don’t want anyone coming to me as the last person who saw you alive.”
Conner reached out and put an arm around my shoulders, pulling me close to him. I was freezing outside, and being next to him felt warm, and safe. “Very generous of you” Conner said. His lips brushed against my forehead, almost as if he was going in for a kiss.
Conner let out a whistle when we walked into my condo. “You won the room lottery for sure. I have to share a cabin with Ken.” I laughed, “Freelancer perks, and hazard pay for dealing with you.” As Conner took in the space, I opened up the mini bar in the kitchen and grabbed a couple of glasses.
Conner walked up behind me as I mixed the drinks. Wrapping his arms around my waist, pulling to me close to him. I could feel his cock stiffening against my ass. Any thoughts that I may have had about not having hotel sex on a work trip was totally out the window. Conner spun me around and kissed me slow and deep.
I pushed him back, to break our embrace. “Stop,” I said, “we can’t do this, you’re married and I’m pretty sure it’s an HR issue.” Conner pulled me closer, and said “Thank god this isn’t an HR off site.” before Conner kissed me again. I wasn’t thinking about consequences as Conner grabbed my ass, and lifted me into his arms.
Conner carried me into the master bedroom of the condo and laid me down on the bed. I started to unbutton my shirt as I watched him pull his shirt over his head. Just looking at his muscular body covered in tattoos.
Conner pulled off my boots as I wiggled out of my jeans. Sitting up in bed, I unbuttoned his jeans. I tried to hide my surprise when I pulled out his thick, nine-inch cock. Conner moaned as I slid his cock into my mouth. Swirling the rim of his head around my tongue before sliding him as deep into my throat as I could. Sliding my tongue up and down his shaft.
Then, Conner pushed me back on the bed. I could feel his big hands pushing my panties to the side and sliding two fingers inside of my dripping wet pussy. My back arched as he kissed my neck and pulled my tits out of my bra with his free hand.
I pulled Conner down on top of me. Grabbing his hand to pull his fingers out of my pussy, I licked my juices off of his fingers as he slid his throbbing cock into my cunt. I tightened my pussy around his shaft as Conner drove his hard cock deep into me.
Feeling goose bumps on Conner’s shoulders I knew that he was about to cum. Conner whispers in my ear, “It is going to be hard for me to pull out. I want to cum inside of you so bad.” I dug my nails into his back and said “If you pull out, I will never speak to you again, and all of your projects go to the bottom of my to-do list”.
The next morning, Conner and I joined the rest of the team for breakfast before the first meeting of the day. While we were in the buffet line, Ken, Conner’s roommate for the trip got in line behind us. Ken jabbed Conner in the ribs, whispering that he noticed that Conner never made it back to the cabin. Conner nodded and told Ken that he didn’t want to get lost in the woods in the middle of the night, so he stayed in my guest room, before loudly telling everyone in the line that I had been given a condo while the rest of them were bunking together in different cabins.
As our co-workers started asking me about my condo and how I got so lucky, I looked over my shoulder at Conner. He winked at me. I smiled, appreciating the way he took everyone’s minds off of us walking into breakfast together. Taking their attention away from our hotel sex corporate hook up.
You think this was a bad decision? I call it experience. If you want more of that energy, don’t miss my phone sex operators guide to having great sex—I’ll show you exactly how I do it.
And when you’re ready to stop reading and start experiencing it for yourself… I’ll be waiting.
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