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Add: 5 August 2015 / 17:34
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Traveling for work was never my favorite part of the job but I didn’t really mind it. Hell, it got me out of the house for days at a time which was something I needed every once and a while. With my husband and two kids, the term “me time” was pretty much nonexistent. The added bonus of it all being on the company dime was just an added bonus.
This trip was a little different though. Normally, I traveled alone and my sales pitches were done solo. This week I had Scott, our newest salesman with me for a little on the job training. Scott had done inside sales before, but being on the road was new to him so the company wanted him to watch me in action before setting him free on his own. I suppose a little help wouldn’t hurt. I made sure he was up to par on the sales figures and quotes to that we could tag team the presentation. As far as pitches go, this was a big one. It was only July but this one sale could put me over the top for my yearly quota and set me up for a nice bonus at the end of the year.
We met at the airport and grabbed an afternoon drink at the Chili’s. Scott was a nice guy and we shot the shit about our bosses, coworkers and other trivial nonsense that new colleagues talk about at first. He was a nice guy, which made this easier. I had worked with some real assholes since starting my career fifteen years ago. He was fresh out of business school, having just finished his MBA. His school had a program that allowed students to enter the MBA program right after undergrad, so he had the brains for the job but just not the experience yet. I liked that he was humble enough to admit that.
We landed in Rochester around 6pm and grabbed a taxi to take us to the hotel.
“Can I help you?” the young girl behind the counter asked us when we walked into the lobby of the Holiday Inn.
“Yes, we have two rooms for tonight. They should both be under my name, Holly James, or under our company name, EQP,” I told her and she typed away at the keyboard
“Ah, yep. Here it is, Ms. James. Room 904.” She said as she prepared the key card.
“There should be another one… for my coworker here.”
“I’m sorry. I only have you down for the room. Let me check to see if anything else is open.” More clicking away at the keyboard. “Well it looks like we are completely booked for the night. There is a big educational conference tomorrow morning in the lobby that has us at capacity. There should be a couple other hotels in the area if you don’t mind staying in separate places.”
I was beyond annoyed but I understand how these things go sometimes.
“That’s fine. We’ll find something.” I said, turning my attention to Scott, “You don't mind do you? Let’s grab dinner and pull something up on the iPad. I have a corporate card so it should be fine.
An hour later…
“What do you mean you’re booked too?” I half yelled, half pleaded into the phone, “You're the last hotel in the city!”
Apparently, the little blond at the Holiday Inn was mistaken. The conference might have taken up a few rooms but there was also a national motorcycle rally going on all week and people from all over the country were taking up every room in the city. Great. Of fucking course. We headed back to the hotel.
“Well, Scott, it looks like we’re sharing the room. I’ll sleep on the floor or something,” I said.
“That’s fine with me. But don’t be ridiculous. I’ll sleep on the floor,” he replied.
It was about 9:20pm at this point so we decided to get ready for bed. The presentation would begin at 7:30am the next morning and I needed my rest to be on top of my game. At this point, this isn’t a big deal. Two adults sharing a room is normal on a business trip. Scott brushed his teeth, washed his face, and pulled the extra blanket from the closet. He tossed a pillow from the bed on the floor and laid down.
“Listen, this is ridiculous. We’re adults. We can share the bed. I’ll sleep under the comforter, you use that blanket. It will be fine,” I told him.
“Are you sure? Won’t that be weird?” He asked.
“I’m sure,” I replied and turned to head into the bathroom to get ready. Here’s the great thing about being a 37 year old woman: the confidence. I know this guy won’t try anything. I’m married with children. I put it out of my mind and that was that.
There was one problem though. I had a bit of a routine on my road trips: a long, hot bath and a session with my vibrator before I fell asleep. It always did the trick to relax me and ease my mind before sleep. I guess I’d be going without tonight. I finished my bedtime preparation and returned to the room.
“Alright! Let’s get some sleep,” I said as I turned the corner, trailing off because Scott was already asleep. Jeez, so much for being nervous! I laid down on the other side of the bed and got under the comforter. I wanted to turn on the TV but was afraid of disturbing Scott. So I closed my eyes and forced myself to relax. Twenty minutes later, I was still staring at the ceiling. Ugh, what I wouldn't do for a quick masturbation session with my bullet! With my eyes now adjusted to the dark, I glanced over at Scott.
As I looked over, he shifted from facing away from me on his side to his back. In the dark, I saw a slight lump under the heavy blanket above his mid-section. I giggled like a little girl. Oh, to be young like he is! I wondered if my husband still got hard in his sleep like that. I know he woke up that way most of the time but as soon as he fell asleep? I wasn’t sure.
Alright, that’s it. I’ll sneak into the bathroom with my iPhone and get one out the old fashioned way, with my fingers. I quietly rolled out of bed and tip toed to the bathroom. Once inside, I pulled up PornHub on my phone and selected the first video on the page. The preview showed a younger man fucking a “MILF” doggy-style. How appropriate, I thought! The video was 13 minutes long, which was plenty of time for me to get this done. In fact, I was only going to give myself about 4 minutes so I wasn’t gone too long. I put the phone down for the video to load and took a look in the mirror as I shimmied my sweatpants and panties down. I lifted my shirt and looked at my tits. Honestly, not too bad! My D breasts had a slight sag to them but my tummy was still flat and my hips had only gotten slightly wider since my 20s.
I looked down at the phone - still buffering. What the fuck? I had already been in here a couple minutes. I realized the wifi was probably maxed out from a full hotel. Shit. I noticed a pill bottle on the counter as I turned off the wifi, hoping the 4G would be faster. Ambien?! No wonder Scott was out so quickly! I turned my attention back to my phone only to see I had no signal what-so-ever. Fine, to the spank bank! I sat down on the toilet and spread my legs, closed my eyes, and began rubbing my clit. I was getting wet but wasn’t feeling my orgasm building as fast as I needed it to. The pressure was having the opposite effect I wanted it to. I looked at my phone and saw I’d been in the bathroom for 11 minutes!
Defeated, I pulled my pants back on and went back to the bed. I sat down and groaned out of frustration, no longer worried about disturbing my Ambien-addled coworker. I laid down and focused on sleep. Just sleep, Holly! 
The harder I focused on sleeping, the more the tingling, unfinished business between my legs. He’s not waking up, just finish here, I thought. I slowly worked my hand inside my panties and began rubbing my clit. The naughtiness of it was really getting me going. After a couple minutes, I changed it up and slipped my middle finger into my vagina and curled it to hit my G-spot. I felt a little tremor and know I was on my way. I went back and forth between rubbing my clit and fingering myself. I felt the familiar feeling deep inside me but couldn't get over the edge.
Cough cough
Scott coughing in his sleep scared the hell out of me. I was so close to my orgasm, I had almost forgotten about him! Now it was gone; back to square one. I looked over at him to see if he was still sleeping. Sure enough - sound asleep, flat on his back… with that lump still under the blanket. I don’t know what came over me, but I reached over and flipped the blanket off the lower half of his body. Maybe it was my unbearable horniness from my failed orgasm. Who knows why I did it but there I was, staring at the bulge in his sweatpants, which now seemed bigger after removing the heavy blanket. Fuck it, he’s not waking up, I thought and leaned over, grabbed his waistband, and pulled it back.
The result was a perfect 8 inch cock flopping out and hitting him in the abdomen. Holy shit, this is happening. Scott hadn't budged. I laid back and jerked him off with one hand while working my clit with the other. After a few minutes of this, I felt my body tense and an orgasm wracked me. I moaned loudly, too loudly. I dropped his dick and rolled over quickly, praying he wouldn't wake up. Moments passed and there was no sign of movement. I rolled back and stared at his cock, still hard and hovering above his stomach. I almost felt bad jerking him off for 5 minutes without letting him cum - even if he was sleeping.
My mind clouded by my arousal and already halfway down the road, I decided to take this as far as I could. I slowly straddled him, lining up his beautiful dick with my dripping cunt. Even if he does wake up, how mad could he be?! I slid down his pole and felt another orgasm building. Without the normal responses from him, it was hard to tell where he was. Could he even cum while sleeping? I decided then to just get myself off ASAP and if he came too, great. If not, at the least, we would both sleep well. Win-win, right? I squeezed his cock with my pussy and sped up my gyrations. Just as I was about to cum, I felt his dick grow even harder and explode inside me. No warning, no expression. Just a silent orgasm. This put me over the edge as I came for the second time tonight. I rolled off him and tucked his cock back into his pants. Surely he might notice some of my dried cum on his dick on the morning but I was no longer worried. I was finally ready to sleep…
Suddenly my alarm was going off and I was waking up from a deep sleep. Last night’s actions came rushing back to me. I was embarrassed. I mean, I had just molested a man without his consent. I noticed he was already out of bed and brushing his teeth. He stepped out of the bathroom and I said good morning.
“Hey! Morning! How’d you sleep?” He asked, cheerily.
“Oh… just fine. Tossed and turned a bit but that’s it. How about you?”
“Fantastic. I barely moved…. I did have some crazy dreams though… Fuckin’ Ambien, ya know?” He replied with a wink, “You’re tossing and turning didn't bother me at all!”
He had been awake the whole time! I turned a deep shade of red and rushed into the bathroom to shower and get ready for the day.
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