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TITLE: A Business Trip Encounter
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LOCATION: JustAnAverageJohn
AGE: 31 - 40
VOTES: 2,150
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I sighed as I pulled into the Doubletree parking lot and put the rental into park. After a tough full day of contract negotiations with the government contractor, I was ready to plop down on my hotel room king-size and call it a night. My heels had been killing my feet all day, but I knew I needed to dress to impress as those misogynistic clowns masquerading as modern men were going to discount me and defer to Mike, my junior on this program. And that's exactly what happened multiple times; at least when they weren't trying to catch a glimpse down my white silk blouse. I hit the steering wheel with an open hand in frustration before I shut off the car. I replayed a few moments of the tense negotiation in my head before I let out another sigh and reached for my Kate Spade laptop bag in the passenger seat and opened the door.

Walking into the hotel, I realized that the light lunch I had--partly to keep the negotiations going, partly as a sign of fierceness--wasn't helping my mood. I looked to the left toward the hotel restaurant and felt the pangs of hunger hit harder than I expected. A quick pivot and a few steps later, I entered the restaurant from the hotel lobby. At half-past five, it wasn't too busy, so the hostess seated me quickly at a table for one. Minutes later my order had been taken, and before six o'clock, my meal was done and I was out the door, charging it to my hotel room. Upon entering my room, I placed my Kate Spade on the desk and flopped backwards onto the bed, phone in hand, carefully slipping off my Steve Maddens from my stocking feet with a well-practiced movement. I brought my phone up to my face and stared at the screen. It was still a photo of Jack, my now ex-boyfriend. I set the phone down on the bed next to my right hip and closed my eyes. I left him just two days before this trip, and while I wanted to call him as I usually did upon returning to the hotel room, I knew that I no longer could.

Don't get me wrong, Jack was a great man: well-educated, very well employed, and a great friend, but as a lover, he really missed the mark. I was happy with him in most aspects but the sex. Oh, it wasn't as if he was too small down there--I'd had smaller and larger before, but he just didn't have the finesse, and he was as vanilla as Breyer's. It also didn't help that his sex drive was about a tenth of mine. When it happened, it was nearly always the same, and variety is the spice of sex life. I let out a light grunt and sat back up, hands instinctively going to straighten my hair. Grabbing my phone as I stood up, I slipped my heels back on. Thinking of Jack made me need a drink, and during dinner I saw the well-stocked restaurant bar. I grabbed my hotel key and my matching Kate Spade wallet from the bag and walked out of the room, automatically glancing at the connecting room door to ensure it had remained locked.

Sitting at the empty bar, I mouthed "top shelf Cosmo" to the brunette behind the bar. She nodded and grabbed the bottle of Belvedere, holding it up for my approval. I smiled and nodded, and she went to work. Thinking about sex with Jack had a conflicting response: while my mind went to frustration, my body responded positively. I could feel a growing warmth down there. I frowned, knowing that it obviously didn't remember the frustration and the need to "take care of things myself" when he left afterwards to clean up.

"Blue moon, draft," said the male voice to my left. Standing no taller than five foot nine, the obvious businessman sat down three stools away. He turned my way and smiled, then turned his smile down. "Bad day?" he asked. At that time, I realized I had been frowning, thinking about Jack's inadequacies. This man's piercing blue eyes looked at me with tender kindness under his sandy brown but graying hair. He looked like he would have fit in at the negotiation meeting today, yet another fiftyish white guy trying to act impressive. I must have frowned again, as he muttered "Sorry" then turned away.

I sighed and shook my head slightly. "No, sorry, not you," I said. "Yes, it was a bad day. You know how travel on the road is, I assume?"

He turned back to face me as the bartender set my pink Cosmo on a little cocktail napkin in front of me. "Charge it to your room, dear?" she asked in an unexpectedly coy tone. Her voice made me smile.

I nodded. "Two fourteen," I said fairly quietly. She nodded back with a smile and went to the draft tap, grabbing a glass for the Blue Moon.

The man next to me waited politely through the transaction then said "Yes, I know the exact feeling. I definitely spend more nights at hotels--and hotel bars--than I do at my flat in Dallas. Where are you from?" I noticed he kept his eyes locked on mine, not even a quick glance at my decolletage. I wondered if I was losing my touch.

"Atlanta," I lied. That's always what I tell people who ask where I'm from. It's a big enough city that no one assumes you might know someone they know. I took a sip of my Cosmo. Strong. Perfect.

"Were you here to see the 800-pound gorilla, too?" he asked. I coughed slightly at this: the defense contractor I was here to visit definitely acted like one and I'd used that exact description in the past. I didn't realize it was a common saying.

"The one with the armed guards?" I asked. "Yes."

He smiled. "You have to love the metal detectors and bag inspection, am I right?" He paused as the bartender set down his beer on the napkin. "Two twelve" I heard him say. She nodded and headed back my direction, cleaning up something near me.

"Well," he said after taking a healthy drink of his beer. "I hope we're not chasing the same contract." A group of five other businessmen came in, ties loosened, and sat on the far side of him, loudly talking about some sports game. The bartender looked up at me, smiled, and, turning away from the new group, subtly undid a button. She grinned at me as she turned away to the five new customers, newly improved for increased tips. I flushed thinking about her sneaky move.

I shook my head at the man. "Just a renegotiation," I said. "Not an open bid." The five newcomers asked for the flatscreen channel changed and volume increased. The bartender--now with another button undone--obliged. I saw all five men stare at her cleavage. I wished her well with her tips.

"I'm sorry, what?" the man asked, raising his voice over the five men, all now groaning about some score.

"I said it was a negotiation, not an open bid," I said more loudly. The man cocked his head and stood up, moving closer. He gestured to the seat next to mine. I nodded.

"I caught 'not an open bid' so I'm happy," he said, sitting down and replacing his napkin with a new one from the dispenser. I noticed he looked down at my left hand. He may have noticed that I looked down at his; I was feeling the Cosmo coursing through me--what can I say, I'm a lightweight. He gestured to the barkeep for another beer, and hesitating a beat, pointed to my drink. I also nodded at the bartender. She smiled at both of us, filling the beers for the five loud sports enthusiasts.

"Flight out tonight or more work to be done tomorrow?" he asked, obviously trying to make small talk. He appeared to be concentrating hard to not look at my neckline while I was looking at him. I chuckled softly to myself.

"One more day of negotiations," I said as I picked up my Cosmo. The cocktail napkin stuck to the glass for a moment then fell off the bar, landing near my feet. He quickly bent to pick it up for me. A gentleman. Or at least not a fan of litter. Wasn't sure which.

Standing back up, he said "Nice shoes. Jimmy Choo's?" He set the napkin aside and got me a new one. A gentleman, I decided, as someone concerned with litter wouldn't want to create more.

I smiled. "Maddens," I said, putting my nearly empty drink down on the new napkin. I decided to take a stab. "Your wife wear Choo's?"

He shook his head. "She hated heels," he said. "But she left me four--no five years ago, so maybe she's changed." He smiled again. "Oh, so sorry, where are my manners. Bill." He offered his hand. I offered my hand in return and my name. "Nice to meet you," he said, as the bartender set down our second drinks. I picked my first Cosmo up and drained what little remained, setting it aside. I was feeling flushed.

He looked down into the remnants of his first beer and appeared to contemplate. "You a road warrior, too? You said negotiations, so contracts or program management?" He finished his first beer in one gulp and set it down on the napkin, pushing it away.

"Contracts," I said matter-of-factly. "Dear God, I wouldn't want to be in program management. People think working in contracts is dull, but I couldn't imagine being a PM," I said, picking up the second Cosmo. As I took a drink, I saw him cringe ever so slightly. I almost coughed as I stopped drinking and said hastily, "Let me guess, PM?"

He picked up his second beer and nodded. Dear God, was I being a fool. "I'm sorry-" I could feel my cheeks begin to burn as I started to apologize.

"No, no, no. If I could do it over again, I wouldn't be in PM either. I'd choose something less stressful." He took a sip of his second beer. "Like maybe brain surgeon." He forced a grin.

I took a large gulp of my Cosmo and couldn't believe my audacity. "I'm so sorry," I started again. "Let me get that beer for you." I flagged the bartender and motioned that I wanted to cover his beer cost.

"Please, you don't have to," he said. I shook my head.

"I insulted you and your profession," I continued, as the bartender, now down one more button on her blouse and showing a massive amount of cleavage and lace bra, came over. I turned to her, saying "Let me get his last beer." She nodded. I finished my Cosmo, getting more flush. I turned back to Bill, who was also checking out our bartender, saying "You know, I should just call it a night. It's an early morning tomorrow."

Bill nodded. "Thank you, but you didn't need to get the beer." He finished his drink and set it down on its napkin. "You know, I need to head out, too. Let me walk you to the elevator."

I smiled and stood up, almost losing my balance in my Maddens, and started for the elevators. Bill quickly caught up and, intercepting me, pressed the elevator call button. When the door opened, he gestured for me to go in first, then came in behind. He hit the "2" button and looked quizzically at me. I nodded, "I'm two as well." He smiled. I may have blushed.

The door opened on the second floor, he motioned for me to go first, and I teetered out on my heels, heading to the last room on the right, my 214. As I passed 212, he paused. As I turned to my door, I looked over to see him smiling at me. I nodded and said, "Good night." He smiled back. I opened my door and went inside.

Closing the door behind me, I was suddenly overwhelmed by the full brunt of the vodka in one swoop. The room was dark other than the light next to the king bed, set low. I felt my cheeks flush--and my pussy suddenly wet. I gently kicked off the Maddens by the door and stepped into the bathroom. Looking at myself in the mirror, I felt a wave of eroticism go through me. I grinned at myself and opened my toiletry bag's secondary section. From within, I pulled out my trust battery-operated friend. I smiled; yes, this is what I needed tonight.

As I left the bathroom for the bed, I looked over to the connecting room door--the door that led to Bill. I smiled to myself and unlocked my side, opening it up. His door was still there, closed; I don't know what I would have done if his had been open. I paused, looking at the door to his room, then I stepped over to my bed, arranged the pillows against the headboard.

I set my vibe on the bed then took off my dress, dropping it to the floor. Standing in my stockings, I removed my bra and matching panties, set them on the side table, pulled the covers down, then hopped up onto the bed. I leaned back against the pillowed headboard and, spreading my stocking-covered knees to each side, closed my eyes.

When masturbating, I usually envisioned Jack as I wished he was, but as I lay there, eyes closed, tenderly touching myself, Jack kept morphing into Bill. Jack's dark hair changing to Bill's graying sand, Jack's brown eyes shifting into Bill's blues. I decided to just go with it as I brought the vibrator to my lower lips and took a quick breath as it touched me. I let out a soft moan as I teased it around. In my head, Jack kept looking like Bill, then switching back to Jack. Keeping my breathing steady, I kept up teasing myself with the gentle vibrations.

I thought I heard a door open--I hoped I heard a door open. In my head, Jack morphed back into Bill, and now in my mind I was seeing Bill standing at the door, watching me. It turned me on more, the thought of it, and I began to focus the vibes where they counted. Eyes closed, taking in the full sensations, soft vibrations in the air, I almost didn't hear the soft thud in the room. I opened my eyes slightly to see that my dream was real, and Bill was there, standing by the open connecting doors, having just dropped his pants onto the floor, cock in hand.

With my eyes partly opened, I smiled and widened my knees to provide a better view. I closed my eyes again, focusing on the buzzing hitting me where I needed it most. The room, quiet other than the soft vibrations, allowed me to hear some rustling coming from the adjoining doors. Peeking once more, I saw Bill had removed the rest of his clothes, dropped onto my room's floor. His erection was hard and a little bigger than Jack's. For being around 50, he was fairly fit; not a washboard stomach, but not chubby, either. His legs were hairy and strong; his chest hair was fairly sparse but graying. He had shaved entirely down there. It was a welcome sight. I felt the need to moan.

"Come to help?" I asked in my softest, most demur voice I could do while enjoying the sensations. He took two steps toward my bed. I slid down off the pillows, pivoting toward him and widening my legs to better his view, but he took it as an invitation and laid down between them. I was about to say something when I felt the warmth and roughness of his tongue right below my clit. With the vibe on top and his tongue slowly moving up under it, warmth and pressure building, it was a miracle I didn't cum right then. I gasped out a "Dear God!" at the sudden increase in sensation. He put his arms under each of my thighs and grabbed my ass with both hands, burying his face deeper, his tongue's pressure increasing as he licked side to side under my clit.

"Oh, yes!" I nearly shouted as I came hard and suddenly. My back arching, my hand having a hard time keeping the vibe right where I needed it. It had been years since Jack had eaten me out, and I didn't realize how much my body had craved for these sensations. Bill kept his tongue moving under my clit, my hand kept the vibe moving slightly side to side above my clit and his tongue, his hands squeezing my ass, my breathing heavy.

The second orgasm felt just like a stronger continuation of the first, and I gasped again with a "God, yes!" barely squeaking out of my mouth. I pulled the vibe away and grabbed his head with both hands, entwining my fingers in his short hair. I guided him upward for more direct pressure on my button, and he took the guidance well. I let go of his head and grabbed my breasts with both hands, squeezing my nipples between my fingers and I gripped them. The sensations were off the wall; I'd never had anything close to this with Jack, and I now felt a strong carnal desire to be filled. "Yes!" I shouted for sure, this time. "I want you in me," I said between heavy breaths. "I want you in me now!"

Bill nearly leapt up to me, his hands on either side of shoulders in an instant. As he had gone down on me, my legs had naturally spread out wide, a side-effect of years of yoga, Pilates, and stretching daily. I was sopping wet from his tongue treatment as well as my own juices as he entered me quickly, fully in one thrust. I gasped from the sudden feeling of fullness, of my pussy being filled. Bill let out a soft moan as he his pelvis slapped into mine. My God, I thought, he's twenty times better than Jack and he only just started!

Bill stayed there, fully in me, looking down at me. I took the opportunity to take a good look at what I could see: not bad for what I assumed was 50, with a somewhat fit dad-bod look, partially graying chest hair. His arms looked muscular, not in a weightlifting way but in a natural way. He looked me in the eyes as I scanned him, then I met his gaze. He smiled. I smiled. "Fuck me hard and fast," I said as coyly as I could. As an invitation, I spread my stocking-covered legs into a straddle and made a show of squeezing my own breasts. He glanced at my widened legs, smiled a gorgeous smile at me and said in a throaty growl, "As you wish."

I thought I was prepared for his first stroke as he looked me straight in the eyes, but the force and quickness were more than I expected. His first stroke set off a loud crack as his skin slapped into mine, the force of which jolted me into pile of pillows behind me. I gasped so loud the hotel bartender most likely heard me. I let out a low moan as he pulled out, then gasped again as he thrust again, as hard as the first. His technique was otherworldly, as his cock stroked my engorged clit going in, but his change of angle mid-thrust had his head rub right across my G-spot inside. Bill had a good dick and knew how to use it. Jack had clearly been more subpar in technique than I thought.

Each thrust created a sensation that left me in a dizzy, blissful haze. I closed my eyes to focus on the feelings awakening from his actions and my own nipple stimulation. The clitoral stroke, the G-spot pressure, all ending in a sense of complete fullness led to a third orgasm in less than a minute of Bill's strong, emphatic plunging within me. As I moaned in pleasure, smiling from eye to eye, legs fully spread to accept him, I could hear his breathing, not nearly as labored as I expected. Bill had stamina, another shortcoming of Jack.

Minutes later, as the fourth orgasm wracked me from my clit to my head, I opened my eyes with big smile, letting out a moan of passion. Bill, eyes closed, focused on the task at hand, continued his pulsing at full force. "Bill," I said breathlessly, and he opened his eyes. "Faster?" I pleaded. Bill smiled, and from an unknown depth of energy reserve, found what he needed to meet my demand. I closed my eyes as squealed aloud as a fifth wave swept through. Dear God, I thought, why had I been putting up with Jack for so long? I've needed this for years, and only now am I finally getting what I deserved.

I opened my eyes again to see Bill, now showing some strain and fatigue--finally! I smiled as big a smile as I could and wrapped my legs around him. "Go ahead," I whispered between breaths and involuntary moans. I pinched my nipples hard. "Fill me, Bill. Fill my pussy."

Bill smiled the largest I had seen him as he unexplainably increased in speed even more. I uncontrollably gasped again, and as I felt a record sixth O build, he slammed into me one last time, emptying deep within me. His pulses triggered my last orgasm, and I let out a low raspy wail as it hit me as hard as the previous ones. He held himself in me as he finished inside, not that he could pull out with my legs wrapped tightly behind the small of his back. He gazed down at me while he worked to catch his breath as I lay there recovering from the waves of ecstasy that had been pouring through me for what seemed like hours in my semiconscious state. I weakly smiled at him with eyes mostly closed.

Bill smiled back at me, a thin film of sweat coating his face. I released him from my legs, setting them wide, feeling the sweat-soaked stockings clinging to them. "Thank you for that," I said in a near whisper. "My God did I need that." I reached up and stroked his cheek with the back of my hand.

"The pleasure was all mine," he replied. "I hope I was able to provide what you needed?" he asked with a twinkle in his eye.

I weakly nodded, eyes still mostly shut. "Yes, oh yes," I said emphatically. "That was one of the best fuckings I've ever had." He smiled and slowly removed his still somewhat-hard cock from me. The sensation of being empty hit me with a longing to return to being filled. I sighed at the sense of missing something I had become accustomed to.

He stood up and mentioned getting cleaned up. I lay there in blissful afterglow.

I fell asleep.

I woke in the morning, still nude except for my stockings, my mind still swimming from last night's erotic experience. I quickly showered and dressed, always glancing at the connecting door; my door was wide open, his was closed. Finally, after reading for what would hopefully be the last day of negotiations, I went to his closed connecting door and pushed. His door opened to a room that was slept in but otherwise completely empty. Bill's luggage was gone. A small tip was on the dresser by the television for housekeeping, more evidence of generosity that I already was well aware of. My negotiations wrapped up that afternoon, and Bill didn't show up at the hotel bar that night, even though I waited.

Every lover since him has been a disappointment in the end when compared to Bill. I keep hoping I'll see him again; I've been back to that same customer several times since then, always staying at the same hotel, hoping for another encounter.

Perhaps one day I can relive the best hotel stay I've ever had.

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