My Boss Made The Mistake Of Sending Me And My Cute Co-Worker On An Out-Of-Town Business Trip


We don’t normally go out-of-town for work; maybe two, three times a year, at most. When we do, we usually go alone. There’s never really been a need for more than one person.
I had just been promoted a couple of months prior, so this was my first big test in the new position. The company decided to send Shannon, a cute blonde intern who was fresh out of college and quickly impressing our bosses, with me. The hotel wasn’t far enough away to take a plane and it made no sense to take two cars, so we planned to take the four-hour trip in my car.

A lot of my friends gave the usual responses when I told them I was going out of town with my cute co-worker, which I kind of expected, but I was surprised that my dad seemed a little worried. He called me as I was packing the night before. “Zach, make sure Shannon doesn’t come on to you while you’re driving.”

I couldn’t tell from his tone if he was kidding or if he was serious. In any case, I didn’t plan on anything happening, plus, she was seeing someone. Aside from the fact that the thought never occurred to me to begin with, the fact that she was unavailable was added re-assurance that nothing would happen.

We didn’t know much about each other before the trip, but over the four-hour drive we learned a lot about one another. She learned that I played soccer for a number of years and can’t cook a decent meal, while I learned that she was born in Texas and can absolutely slay Eminem’s part in “Forgot About Dre.”

We checked into the hotels and headed for our rooms, which were right next to one another, and unpacked before heading out to grab some dinner. It wasn’t until the check was on its way that I realized she had not mentioned her boyfriend, or anything involving her relationship all night.

On our way back to the hotel, I figured that it couldn’t hurt to ask, so I did. “So, how are things with Vince?” I asked. She flinched. I don’t know if she knew that I saw her, but she quickly composed herself. “Um, well, we’re not together anymore,” she said, clearly caught off guard. “You know how it is.”

I asked if she wanted to talk about it, but she politely declined. “Thanks, though,” she said, grabbing my hand on the shifter. After about a second and a half, it hit her that she was holding my hand, and quickly pulled away. “I’m so sorry about that,” she said, nervously. I laughed, “It’s okay, I won’t tell anyone.”

As we walked through the hotel lobby, I thought about whether or not I would try to kiss her at the end of the night. By the time we reached the elevator, I knew that it was a horrible idea. I had too much to lose for something that I wasn’t even sure she wanted. We got to our floor and didn’t give each other so much as a hug goodnight.

As I was washing my face, I heard a knock at the door. I dried off and opened it to find nobody there. I went back into the bathroom, heard another knock, and again opened it to an empty hallway. Looking around, I heard another, softer, knock. It was the door between our rooms.

The distance from the front door to the side door couldn’t have been more than three steps, but each one felt like a mile. I felt my heart beating harder with each one. I reached for the knob and opened it.

She was standing there in what looked like nothing but a t-shirt. “Hey,” she said. “I have a question for you that I need to ask and can’t wait until the morning.” I stood there, shirtless in my gym shorts, and inquired.

“And that is?”
“Whose room are we staying in tonight?”

I wrapped my arm around her back and pulled her towards me. “So I guess this means yours?” she whispered. I kissed her, walking backwards into my room. She kicked the door closed on the way in. I slid my hands down her back and under her ass, grabbing it tight before lifting her up. She wrapped her legs around my thighs as I pressed her against the wall and kissed her neck. Her arms were around my neck, her nails gently grazing my scalp as she began breathing harder.

I let go of her ass and wrapped my arm around her torso, my other hand running through her thick blonde locks. As I continued kissing her neck, she started nibbling on my ear. I couldn’t tell if it was me kissing her or the hot breath of my heavy breathing, but she began to moan, softly.

She pulled away, then stared at me without saying a word. I looked into her bright blue eyes and leaned in to kiss her. She leaned back. I leaned in more. She leaned further back.

“Why are you teasing me like this?” I whispered. “Because I like seeing how much you want me.” She slowly wiggled her hips against my groin. “How badly do you want me right now?” I couldn’t even bring myself to say something sexy back because all I envisioned at that moment was fucking her. “Bad,” I said, softly.

“Show me how bad,” she challenged, wiggling her hips slower.

Without hesitation, I grabbed the collar of her shirt and ripped half of it off in one motion. She gasped, as her tits were now inches away from sliding out of her shirt. I didn’t waste any time, and ripped the rest of her shirt before taking it off her.
She was gyrating against me, grabbing my hair and kissing my neck, harder this time. Her kissing turned into sucking, which turned into nibbling, which quickly turned into light biting.

“What are you gonna do to me?” she sighed in my ear. I buried my face into her chest and started sucking her tits as I walked across the room with her still wrapped around me.
“Mmmm, I like where this is going,” she moaned, her head tilted back in ecstasy.
I got to the windows and opened the blinds, then pressed her naked body against the glass. The chill from the winter cold caused her to arch her back in shock. “Oh… wow,” she panted. “Now what?” As I started to kiss her again, I began pulling my shorts down. I rubbed my cock against her clit and started to slowly slide it in to her wet pussy. “No,” she whispered. “Let me.” She reached down to start playing with herself. She slowly fingered herself before massaging the head of my cock.

“You’re pretty big,” she smirked, guiding me into her tight pussy. As I began to thrust forward, I could feel her starting to flinch again… this time, in a good way. I could see her eyes start to squint, so I wanted to make sure not to hurt her. “You OK?” I whispered. “Yeah, you’re just… thick.” When I got all the way inside her, I could hear the vibrations in her breath as she panted. “OH! Wow.” It took a little while for her to adjust. “Mmmgh fuck,” she groaned, before getting comfortable and working her hips with the rhythm of mine.

I started fucking her harder, her breathing getting heavier. I wrapped both of my arms around her and pulled her off the glass while still inside of her. I pulled her against my chest and starting fucking her even harder. Trying to muffle her screams, she started biting my collarbone, her nails digging in to both of my biceps.

“You’re going to make me cum, Zach,” she panted. “Don’t stop.” The closer she got to climax, the harder she sank her teeth into me. “Oh my God. Oh my God,” she moaned. “I’m cumming. Oh my God I’m cumming!” She grabbed my face with both of her hands and kissed me, passionately. When our lips broke, she pressed her hand against my chest and leaned back, telling me to move back towards the bed.

“Relax a little bit — I got this,” she smiled. I finally pulled out of her to let her down. I couldn’t tell who had more trouble trying to stand; her legs had been wrapped around mine for so long and mine were beginning to buckle after a while. “You must be exhausted,” she said, massaging my cock. “Take a load off.” I laid down on the bed and she slowly crawled on shortly after. She ran her hands up my thighs before swallowing my cock without any assistance. Exhilarated, I couldn’t help but close my eyes and enjoy myself. When I finally opened them, she was staring back at me, the head of my cock still secured in her mouth.

“You’ve been missing quite a show,” she said, holding my cock while licking it out of the side of her mouth. “You won’t want to miss this.” She twirled her tongue around the head of my cock and slowly started working her way down my shaft. Every time I thought she was going to stop, she kept going.


She stopped when she reached the base — the first girl to ever deep-throat me.
The feel of my cock touching the back of her throat and her entire mouth around me was too much. I could feel myself ready to cum, but I wanted to give her a warning.

“Soon,” I groaned.
“Mmm, are you going to cum for me, baby?” she whispered. Again, she started going down on me. Just as she was reaching the base again, my legs started convulsing as I exploded into the back of her throat. I grabbed the edge of the bed and squeezed it tight until my body finally relaxed.

She slowly pulled herself back up the shaft of my cock and licked the head for an additional clean-up. “Jesus Christ, that was incredible,” I sighed. Once I caught my breath, I pulled her up under my arm to unwind. I could feel my heart pounding against her soft cheek. I’ve always been one to give first, receive last, if at all, so I felt a little guilty that I didn’t take of care her, orally, beforehand. “You didn’t even let me go down on you,” I said, nudging her. “I guess I owe you one.” She quipped back, “And a new shirt.” Thought Catalog Logo Mark

About the author

Zach Armstrong

More From Thought Catalog