Note: this is one of my favorite fantasies. I've read other submissions with similar settings, but they all seem to jump into an affair without much thought. That's just not how I imagine it happening. So here's my take on the classic business trip fantasy with a few of my personal kinks thrown in. I hope you enjoy and would love to hear your thoughts.
*****
Jen and I arrived at the hotel late in the evening. We were working all morning long finishing up our sales presentations and going over the final details before boarding a plane at 6 p.m. We landed in the middle of Kansas for our Mid-American conference. I hated this conference. It was always so boring. There's only one hotel in the whole Podunk town, and it has the only restaurant. But for some reason, the farmers in this community loved to buy whatever we were selling. So my company continued to come back year after year for the 3-day conference. These three days made up roughly 35% of our yearly commission, so it wasn't a question of going or not, just a matter of getting through it.
At least this year I had a coworker come along so we could do twice as much damage. Jen was new to the company, but not new to sales. Hell she was built for sales. Impossibly charming, with light brown, shoulder-length wavy hair. Her blue eyes seemed to glow. As if that wasn't enough, her slender, toned body with tight curves was enough to make any man melt. Even as an adult you could just imagine her as the most popular girl in school who intimidated all the guys. At least that's how I always thought of her. She had on a tight business jacket and skirt combo that barely showed some of her cleavage. Unnecessarily formal, but it also made her look even more intimidating.
We arrived at the hotel and went to the front desk to check in. "Hi, we should have reservations for two." I said with a yawn, hoping soon I'd be resting in my bed.
"Yes, here you are sir. One room for you and your guest." The desk clerk said with a smile.
"Wait, what? No, we should have two reservations...two separate rooms." I look over at Jen. "You did remember to book your room, didn't you?"
"Me? I thought since you asked me last minute to tag along you already had everything lined up." She said with a panicked look.
My face dropped. It was a total oversight rushing to get everything ready in time. I turned to the desk clerk who had been waiting patiently while we bickered like an old married couple. "I'm sorry, but would you happen to have an extra room we could check out?"
She began typing quickly and staring at her monitor before returning to me, "I'm sorry, we're completely booked for the conference. It's the one time of year we're full, and even have a waiting list."
I was about to ask if there was anything she could do, or if there were any other places in town to stay, but I already knew the answer. This hotel practically was the town. It was almost midnight, and we didn't have much choice. "Looks like we're staying together, Jen." I said with a phony smile, which she returned right back.
"Oh joy. Can't wait." The sarcasm was painfully obvious.
The woman behind the counter handed us our key cards and we made our way to the elevator. At first, neither of us said a word. I was trying to determine whether or not I should tell my wife about this. Judging by the way Jen was playing with her wedding ring on her slender finger, I'm guessing she was wondering the same thing. She looked worried about disappointing him.
"Just tell him it was my fault. Tell him I forgot to book a room, and we had to share a room. He'll probably want to kill me, but at least he won't be mad at you." I offered as an olive branch.
"Actually, I think he'd still want to kill me. I'm not even going to mention it. Let's just get some sleep tonight, and hopefully a room will open up tomorrow." She said with a smile, obviously covering up the stress she was feeling.
"That's probably a good idea. I'm sure my wife wouldn't like the idea much either." We both let out a nervous laugh and went back to staring at our luggage. I was imagining how much my wife would actually hate the idea when the sound of the elevator door opening finally snapped me out of it. We rolled our suitcases down the hall and came to our room. I slid my key in, and pushed the door open. The room was incredibly dark before I finally found the lights. It was just as I feared. A tiny, one-person room with one fairly small bed that was right next to the bathroom. My heart sank, and I could tell it made Jen even more uneasy. There was virtually no privacy.
"I, uh, I'll just sleep on the floor." I offered politely as I started to unpack some clothes into the barely functional closet.
"Nah, don't bother. This room is so small there's really no point. I guess I'll go get ready for bed in the bathroom." She grabbed some things from her suitcase and rushed in and closed the door behind her. The walls were so thin, I could actually hear her moving behind the door. I heard the shuffle as she removed her clothes and turned on the sink to wash up. I really wasn't trying to be a pervert, but the whole thing felt oddly voyeuristic imagining what she was doing in there. It was kind of fun in a distracting sort of way, keeping my mind temporarily off how uncomfortable it was.
A few moments later she was back wearing a short cotton, white robe that went down to her mid thighs. It was tied tight around her waist, and I could see a fair amount of cleavage through the top opening.
"There was only one robe in there, so I took it. I hope you don't mind?" she asked as she walked over to her suitcase and tucked in her clothes she was previously wearing. "I wasn't planning on sharing a room, so I didn't really bring any pajamas to wear. I usually sleep in, well..." and she awkwardly trailed off and looked back toward her suitcase.
"No problem at all." I said trying to be as accommodating as possible, but then it hit me...I didn't have anything to sleep in either. I went into the bathroom and quickly brushed my teeth. I took off my buttoned shirt, pants and undershirt. I was left standing there in my boxer briefs. I was covered, but not by much. You could make out the entire shape of my soft, thick shaft and my bulge hanging below. Here goes nothing, I thought as I returned to the room.
Jen was in bed, still in her robe and under the sheets. She was putting some lotion on her hands and looked over at me. Her eyebrows arched. I could tell she was not expecting to see me in just my boxers. I could feel her eyes giving my six-foot muscular frame the once over and then slightly lingering on my manhood, making out the shape before quickly looking away. In almost in any other circumstance I would have felt flattered, or turned on even, but in this instance it was just a sign of how uncomfortable this situation is. I turned off the light and climbed into bed next to her. Without touching her I could feel her warmth heating up under the sheets. We both just lied there, staring up at the ceiling on our backs as our eyes adjusted to the dim light coming through the window.
I didn't have to look at her to know she was wide-awake, just like I was. Normally if I was at home I would try to have sex with my wife to help me sleep, or at least that's how we used to be. That turned into more of me quickly jerking off after she had already fallen asleep. But even that it was out of the question now. Knowing that I couldn't relieve myself, made me realize how necessary it had become for me to sleep. And my tired body was reacting in kind...just the thought of it started to make me to grow harder. I rolled over on my side with my back facing her, so she wouldn't see my growing erection nearly poking a hole through my boxers. It started to hurt being held down for so long, and the more I thought about it, the harder it got. I tried to focus on anything non-sexual, but it was no use. I just lied there, in frustration and pain and wished for morning to come quickly.
I heard her roll over letting out a similar sigh. I looked at the clock, it was nearly one in the morning, and we both had to get up in just a few hours. Each second ticking away, I could feel a little more pre-cum starting to ooze out onto the front of my boxers. I had to do something.
"Uhh, Jen?" I said, already beginning to feel slightly embarrassed and nervous to bring it up.
"Yeah?" she said quickly.
"We have to get up in a few hours to get ready...we're really going to be no good to anyone if we don't get any sleep."
"Yeah, I know. We're going to be a couple of zombies out there." She said sounding equally frustrated.
"I know how much you love your husband, and I love my wife just as much. I'd never do anything to hurt her..."
"Yeaahhhh...?" she said a little nervously.
I wanted to keep going, the words were almost out, it was painfully obvious in my head what I was hinting at...I needed relief, but I just couldn't bring myself to ask. This was a coworker, I didn't even want to think about what would happen if I asked if I could masturbate and she was offended. I could be fired, sued, or just humiliated if she spread the word around the office.
"Nothing, don't worry about it, Jen." I chickened out. "Let's just get whatever sleep we can."
"Ok." She said flatly. And I understood completely. It was hopeless for both of us, but not much we could do about it.
The night seemed to drag on forever. I'm not sure if I got much more than 15 minutes of sleep the whole night before the alarm went off at 4 a.m. "Stupid farmers starting their days so damn early" I mumbled to myself as I shut off the alarm.
I'm not sure how much sleep Jen got, but judging by how little she moved when the alarm went off I would guess not much more than me. Her back was facing me as she lied on her side. I shook her shoulder lightly, "We gotta get going if we don't want to be late."
She rolled over and grumbled. Her eyes barely open, her robe loosened as she turned revealing more of her cleavage than she probably wanted to show.
She let out and exasperated sigh, and closed her robe as she sat up. "Jeez, I slept like shit." She said wiping her eyes.
I never heard her swear before, but I completely understood her frustration. "Me too." I said, keeping my back to her as I stood up to find my clothes for the day. I was partially hard and made sure to hide that fact from her. God, have I been hard all night? I didn't think that was possible, but it certainly would explain why I barely slept. Grabbing my clothes, I headed toward the bathroom and saw Jen dart in there before me. She shut the door nearly right in my face, but I'm not even sure she saw me walking toward it.
I lightly knocked on the door. "Jen? Are you going to be long? I gotta get in there and get ready." As soon as I said that, I realized how selfish it sounded. I'm sure she wanted to get ready and it would probably take her twice as long to do so. I heard the toilet flush and she walked out clutching her robe tightly. She did not look happy.
"Sorry to burst your bubble, but neither of us has time to get ready. First day registration and setup starts in just a few minutes." She said brushing her knotted hair away from her drowsy eyes.
