If you travel enough you start to see the same faces. Business travels seem to take the same flights. They go to the same cities. They stay at the same hotels. Everyone picks an airline or hotel chain based on a loyalty program. So if you spend a month in the downtown Hilton in Minneapolis, it's not uncommon to run into someone you met in the bar a year later in the same hotel brand in another major city.
It's not like you become friends. You might strike up a conversation in a bar. But mostly it's just a polite nod when you see the same face again in the parking garage or getting off the elevator. It's probably not that much different than people with traditional jobs in skyscrapers or giant corporate campuses. There are people you know, but you don't really know.
Life on the road is lonely. It's virtually impossible to have a relationship back home when you spend most of the week in a hotel. People have different ways of coping. Most drink too much. Others spend every waking moment focused on work. And some turn to sex.
Everyone has their preferences. For some it's blowing off steam with a co-worker after spending hours together doing business. I've known tons of consultants who ended up in passionate, tumultuous affairs with their colleagues. I've also known men and women who preferred to troll the bars looking for meaningless one night.
I was no different than the rest. I'd fucked co-workers and clients and had both go terribly. I'd slept with flight attendants and women who worked at hotels. And more than once I'd gone back to a strangers room after sitting in the hotel bar until last call.
The hotel bar was the easiest. There wasn't much downside, unlike fooling around with a colleague. And it didn't require the effort of building a rapport with someone you talked to in two minute doses when you were finding your seat or checking in. The only downside is that it was always a complete chance. You couldn't go to the bar looking for something. Most nights the room was filled with men. And not every woman was looking for a one night stand. You just had to get lucky and sit down in the right seat on the right night.
Most of the encounters were forgettable. Just a good time between two strangers who were often half-drunk. Typically it was just a one night thing. Though there were times that it escalated to something more. It never came close to being a relationship, though. More like fuck buddies or friends-with-benefits.
I should have known that Diya would be different.
I noticed her in the hotel bar on Monday evening. I'd arrived in town that morning and spent the day at a client's office. She wasn't one of the familiar faces. I was certain I'd never seen her on an elevator or walking through the airport. It would have been impossible to forget her. She was gorgeous.
Diya was Indian, but spoke with a British accent. She had big, beautiful brown eyes, pouty lips, and long black hair. Her body was fit and curvy. She looked like someone who belonged on a runway. Not sitting in a hotel bar with a laptop and a glass of wine.
That first night I sat at the end of the bar. She was alone at the nearest booth. I watched a steady stream of men in suits or khakis walk over and attempt to start a conversation. She politely brushed all of them away. I wasn't surprised. She didn't look like the type of woman who could ever be picked up in a bar. Especially not by middle-aged men in golf shirts or cocky young consultants in pinstripes.
I didn't even attempt an approach. I sat quietly at the bar eating dinner and then nursing a few drinks while I tapped away on my own keyboard. Diya left alone around eleven. I stayed until midnight. I spent the last half-hour making a half-assed pass at an older blond in a beige pant suit who came in and took the stool by me. She looked to be in her early forties—about 10 years older than me. I'd found over the years that women around forty were most often the ones looking to have a little fun. Either that, or the women right out of college.
The woman—Claudia—was willing to flirt. But it was obvious that it wasn't going anywhere that night, so I packed up and headed to my room alone. Before I left, she promised she'd be in the bar again the next night.
The next two nights were similar to the first. I had dinner at drinks sitting at the bar. I'd see Diya working alone at a booth and politely turning anyway anyone approached. And Claudia would eventually come in, sit next to me, and flirt for a few hours without it actually going anywhere. Either she just wanted a little male attention or she was holding out until Thursday—her last night in town. I'd seen that behavior in the past. Someone who wanted to make sure it was just a one night thing. I assumed we would sleep together and I was happy about it. Claudia was a little plain, but still attractive and interesting. I didn't bother trying to meet someone else. If it didn' t lead to sex, I was still glad just to have some company in the bar.
On Thursday I got out of the office just after five. I went straight to the bar. Though we'd not made any plans, my hope was that Claudia would show up early, too, and she'd be up for slipping out early. The week had been busy and stressful. I was dying to blow off some steam. I wanted something more than a half hour romp after too many drinks.
The bar was mostly empty at that hour. Surprisingly, Diya was already set up in the same corner booth. She looked up and flashed me a smile as I walked in. I nodded in her direction. It was the same casual greeting I exchanged in hotels and airports all over the country with people I would never actually talk to. I was surprised she even recognized me. I thought perhaps she was just being polite since we were the only ones in the bar.
I sat down at my stool and ordered a drink. I was seated or only a couple of minutes when Diya came over and stood next to me. She signaled the bartender for a drink.
Up close, she was even more stunning. Her dark hair was parted in the center and hung down to frame her face. She wore a black skirt and blazer with stockings and heels. Her blouse was square-necked and low-cut with black lace trim. It was a deep red silk that looked good against her brown skin and showed off the swell of her bosom. It was covered in a gold pattern with big gold buttons.
"A pretty woman smiles at you and you don't come over to say hello?" she said to me in her British accent.
I was surprised. At first I couldn't believe she was speaking to me. Much less comprehend what she'd said.
"I'm sorry," I said. "I didn't realize it was an invitation."
"You've been sitting here all week glancing over at me," she said. "And you haven't said a thing to me. What else would it be?"
"Well, every time I glanced over you were sending someone away," I responded. "I took that as a sign."
She laughed. It was beautiful, deep sexy laugh.
"Old men and overgrown frat boys," she said. "That's the only guys who've approached me. Not exactly my thing. I can do better, don't you think?"
I nodded my head.
"Definitely," I said. I couldn't get over how attractive she was. I've always done fine with the ladies, but she felt out of my league.
"You can too," she said.
I gave her a puzzled look.
"Don't play coy," she said. "I've noticed your companion this week. I think you can do better than an older woman who wants to have a fling with a younger man but can't follow through on her desire."
I blushed. I felt embarrassed that she'd noticed me and Claudia.
"You're very blunt," I said. "I suppose you've heard that before."
"I'm a female consultant in my late twenties. Almost everyone in this industry is older and male. I've been called a lot of things. Most of them not as pleasant as blunt," she responded. "That one is almost a compliment. I am blunt. Is there anything wrong with that?"
"No," I responded. I thought about how passive Claudia had been all week. "Blunt is refreshing."
"Good," she said. "I'm sick of the food here. It's awful. And I hate going to nice restaurants alone. Do you want to go somewhere with me? There's a great steakhouse that's not far from here. I'm Diya, by the way. I guess we actually haven't met."
I introduced myself.
"So? Are we going?" she asked.
I had a decision to make. I wasn't completely sure where an evening with Claudia would lead, but I felt confident we'd end up in bed. It seemed much less likely to happen with Diya. In all likelihood we'd have a nice meal, some conversation, maybe a few drinks, and it wouldn't go much further. Still, there was a small chance something might happen with her. And even if it didn't, I'd probably enjoy the evening. I finished the rest of my drink. Diya chugged her wine. Then we got our things and left. If it went badly, maybe I could still catch Claudia later in the bar.
Dinner was great. The food was excelling and things just clicked between me and Diya. The conversation was interesting and funny at first. There was an undeniable chemistry between the two of us. It was unlike any experience I'd had on the road. Eventually, it turned flirtatious. She'd punctuate what she was saying by reaching out to touch my arm or hand. I couldn't stop staring at her and admiring her beauty. And I'd catch her staring back at me with those big brown eyes.
We left the restaurant hand in hand. We were slightly tipsy, but we'd only split a single bottle of wine and were far from drunk.
"What next?" she asked. "How should two young, beautiful people spend the evening in the Windy City?"
"I don't know," I responded. "I've spent a lot of time here for work, but I haven't really gone out looking for entertainment at night. I could look on my phone and try to find a bar or a club?"
"Yes," she responded with a slow head nod. "That could be fun. But I'm just not sure of something." she said.
"Not sure of what?" I asked. I was worried that she didn't feel comfortable going off alone and getting drunk with me.
"I'm not sure it will leave us enough time," she said.
I gave her a puzzled look.
"To fuck," she said with a smile.
She pressed her hot body against me. Her large breasts crushed against my chest. She was tall for a woman, and with her heels on it was easy for her to turn her lips up to meet mine.
We kissed for the first time. It was slow and wonderful. I wrapped my arm around the small of her back and pulled her tight. My lips parted and our tongues met. I was instantly hard.
I stepped to the curb and quickly hailed a cab. We'd walked to the restaurant, but it had taken over 20 minutes. Neither of us wanted to waste that much time getting back.
We were like two horny teenagers in the backseat. Neither of us paid attention to the cab driver. It didn't matter if he was glancing back. We didn't care.
Diya leaned into me, lifting her ass off the seat. We kissed. I ran my hand up her stockings and under her black wool skirt. I realized she was wearing garters. I went higher and cupped her ass. She was also wearing a thong. She looked at me and winked.
"Were you planning on this tonight?" I asked.
She shrugged.
"More like hoping," she said. "I get bored on the road. It's nice to find some company. But I don't usually find someone to pique my interest."
We kissed again. I kept my right hand on her ass. My left went to her breast. I rubbed it through her camisole and gave it a squeeze. A lusty moan slipped through her lips.
She reached for my cock. I was still rock hard. She rubbed and teased me through my slacks. We kept kissing one another. I glanced up and saw the driver watching us in the rear view mirror. But I still didn't care.
Diya unzipped my trousers and slipped inside. She wrapped her hand around my thick boner.
"Oh my," she said with arched eyebrows. "You get better and better."
She started jacking me off. I leaned back and let her pump my dick. I looked in the mirror and saw we still had an audience. I closed my eyes to block him out. I felt like I could blow at any second.
The driver pulled up to the hotel.
