Business Trip - Shared Hotel Room

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.

I glanced at my watch, "Damn, you're right. Well, why don't you get dressed out here and I'll change in the bathroom to give each other some privacy."

She nodded and started to drop her robe as she walked away. I saw her bare back exposed down to her waist before she turned the corner out of view. I stood there for a second taking in the teasing scene before rushing to get dressed in the bathroom. Quickly throwing on my work clothes, I barely had time to adjust my tie.

When I came back into the room, Jen had her back to me. She had on a conservative business skirt that went down to her knees, but not much else. Once again her upper, bare back was exposed to me and it was mesmerizing. I watched silently as she slipped on her bra and clasped it behind her back effortlessly. As she put on her blouse and started to button it up, I coughed politely to let her know I was in the room.

She turned as she finished buttoning the last few buttons, giving just the tiniest view of her cleavage before she was covered up. "You've got that bed head look mastered."

"That's because it actually is bed head." I joked. "You about ready?"

She threw her hair in a ponytail and we were out the door before the sun even came up. From there the whole day was a disaster. Bags under our eyes, constantly yawning, we were completely off our game. She had lost her irresistible charm and I could barely finish a sentence without losing my train of thought.

Several hours later, the day came to a close and all potential customers had left. "Well that sucked." She said plainly.

"Understatement of the year." I added. "Want to grab a drink before we head in?"

"I will need more than one." She lightly smiled.

There was only one bar at the hotel, and fortunately it wasn't too crowded. We found two seats in the corner and reviewed our notes for the day. Nothing went as planned. We agreed we'd need more sleep tonight in order to try to salvage the remaining few days of the conference. Even though we were both exhausted, neither of us was in a hurry to get back to the room. There was just awkwardness waiting for us there.

After finishing our drinks I said, "come on, it's getting late." She nodded unenthusiastically. The walk to the elevator was painfully silent. Everything about this trek back to room was taking longer than it should have. We waited for a few minutes for the elevator to finally arrive.

After I pressed the button for our floor, she leaned against the wall of the elevator lifelessly. "I cannot have another night like last night. I need to sleep." She said with her eyes slowly closing.

The door slid open and we walked sleepily to our room. She went into the bathroom and brushed her teeth without a word. As tired as I was, the anxiety of sharing the room with little privacy was starting wear on me. I turned out the lights and wasn't sure this night would be much better than the last. Jen returned from the bathroom wearing only her bra and panties, but it was hard to make out any details without the lights on.

I went to brush my teeth, and stripped down to my boxers again. My bulge was a painful, growing reminder that sleep would be hard to come by. I quickly left the bathroom and hopped under the sheets hoping she wouldn't notice my covered erection. I thought maybe she'd be asleep, considering she could barely walk back to our room, but no such luck.

Again I twisted and turned in agony. This was much worse than last night. There was more built up pressure in my groin and I was twice as tired as last night, but still wide-awake. My member pulsed painfully against my boxers and I simply couldn't take it any more.

"Jen?" I asked hesitantly.

"What?" She answered instantly and frustrated.

"I'm not sure I'm going to be able to get much sleep like this." I said plainly.

"Me either." She said with a sigh. "This is awful."

"It doesn't have to be." I said with the slightest bit of optimism.

"What do you mean?"

"Well, as I started to say last night, I know how much you love your husband. And I love my wife just as much." I paused, my nerves growing heavy.

"What are you getting at?" She sounded nervous but intrigued.

"Well, there's just something I usually need to...uh, or...well something that helps me fall asleep." I said awkwardly, hoping more than anything I didn't freak her out, or earn a slap from her. I barely made out that she nodded her head in the dim light, like she was thinking the same thing and just didn't want to admit it.

"This is really embarrassing, but would you mind if I...?" I hinted at it, hoping to god she wouldn't make me say it fully.

She didn't say anything at first, and I could hear my heart pounding it was beating so fast before she finally responded. "Yeah, Ok." She said softly.

Oh thank god, I thought. I could barely contain myself, I rolled onto my back, as was my usual custom. Sliding my hand into my boxers, I lightly felt my full length and rubbed my shaft against my leg...something I had done thousands of times before but never really noticed that's how I always started until I became hyper aware of every move in this moment.

I thought all of our problems would be solved if we could just relieve ourselves and get some sleep, but the awkwardness was only beginning to set in. In my head I imagined we'd both be craving this relief, but judging by the movement under the sheets only I was taking advantage of the moment.

As I lied there on my back, I was clearly pitching a tent through the sheets. Every hand movement I made felt painfully obvious, and I found it difficult to get a good rhythm going. I'd stroke a few times, pulling the skin up and down my shaft and then become overwhelmingly self conscious and back off for a bit. It would have been an incredibly pleasurable tease, if I wasn't so stressed.

I wasn't sure I'd even be able to finish at this rate, but then it happened; she let out a soft little moan. The kind that was so subtle, you just couldn't fake. She immediately caught herself and tried to be quiet, but she knew it was too late.

"Are you...?" Was all I managed to say.

I made out her slight nod in the dark room. My eyes had begun to adjust to the darkness and I could clearly see her upper arm steadily moving as her breathing became deeper. Oh thank god, I'm not alone I thought.

My strokes grew more confident and consistent making a light patting noise as my hand kept hitting the blanket covering us.

She sat up slightly and reached around her back, unhooking her bra. I could see the silhouette of her breasts as she slid the straps over her shoulders and down her arms, tossing it on the floor. Her nipples seemed to glow for a moment in the cool light before she pulled the sheet back up over her to cover herself.

My hand started stroking a little faster under the sheet, sliding up and down and giving a little twist when I got to the head. I felt a soft, warm hand on my shoulder interrupting my movements.

"Jason, this goes without saying, but you absolutely can't tell a soul about this...not even your friends or people I'll never meet. No one can know."

Her hand felt so warm, so soft, I forgotten what it was like to be touched by another woman, especially in such an intimate situation. The sheet that was balancing above her chest slightly fell and revealed the tops her perky breasts. I could almost make out the shape of her hard nipples under the covers before I finally snapped out of it.

"No one can know. It's not even a thing we're keeping a secret...we're just trying to get some rest." I could tell I was babbling and talking quicker than normal, so I stopped before I ruined the mood. She nodded in agreement and lied back down on her pillow. She let her hand wander back under the covers. I nervously moved the sheet down a little revealing her breasts, but still left myself covered below the waist. My arm flexed as my hand grabbed and massaged my member. I could tell her eyes were watching my movements, and I was watching hers. I couldn't take my eyes off her beautiful breasts lightly rising and falling with her increased breaths.

Her hand started to speed up as she watched my repetitive motions and soon she was arching her back, moments away.

I was getting closer and closer too. Now that I saw her arching I started to let go, and then panicked. Where was I going to finish? Normally I'd just aim back slightly and cum on myself, but I was afraid she'd be grossed out by that. I heard her moaning as she trembled next to me, but I wasn't even watching her. I was too focused on my own predicament as I let out a little gasp about to release, when she pulled the sheet off of me. It was just in time as she exposed my pulsing cock, I shot a few spurts onto my chest and belly as my body shook involuntarily from the eruption.