I rushed through the streets and dodged traffic as I made my way from the bus to my work. I was running late because my Prius was out of gas and has been for a few days now. I'll get paid soon, but it's the bus for me until that happens. With my credit cards maxed out, I have to sneak onto the bus and pretend to tap my Ventra card.
At least my boss is cool. I had been working at Montegue in Chicago for almost a year. At 23 years old, it was the longest time I've been at the same job and I was quite proud of that fact. I was a waitress at the bistro and I usually worked the night shift. The bistro never closes as it's the one place in the hotel that will make you a burger or breakfast at any hour of the day.
I liked my job, and the night shift suited me perfectly. I would usually start around 8pm and work until morning, around 5 or 6 am. The night shift was mostly quiet, but you could count on a few interesting characters rolling in as the night progressed. Just last week a woman walked in dressed from head to toe in black latex. Followed close behind was a man that clearly was in some kind of BDSM relationship with the woman. He was fit looking and wore all kinds of straps, buckles and chains. It was strange to see, but we didn't have many customers that evening so only a few heads turned. The bistro is expansive with dim lighting and lots of nooks and crannies for patrons to have some degree of privacy.
We would often get working girls coming in after finishing up with their clients. My favourite customers were couples meeting for the first time. It was usually sexual in nature and you could feel the energy between them as they would sit and whisper to each other. I often wondered what kind of freaky sex they would end up having later on in the hotel. I pictured myself in a situation like that, meeting someone for the first time, discussing the sexy details of what we would do together. The tips were always generous too. There's something about late night rendezvous that make people feel more charitable than during the daylight hours.
This is how I met Penny. I'll never forget the first time I saw her; she was so beautiful and it was effortless. She came in one evening around 3:30 am and took a seat at the bar. She was incredibly sexy, but she had the look that she wasn't even trying. She wore almost no makeup at all, or not that I could tell. I guessed she was somewhere in her mid 30's, but she looked so youthful and had glowing skin. She was wearing leggings and a very tight sports bra that struggled to contain her ample breasts. Her long dirty blonde hair was cinched in a tight ponytail. Her hips were on the larger side and a perfectly round bum, but she had a tiny waist. I couldn't help but wonder if she was all natural. She looked quite tired - understandable considering the time.
"Can I get a sparkling water please?" she said.
"Absolutely," I said. "How's your evening going so far?"
"Just fine, thanks. Oooh, look at you. You're a pretty little thing!" she said.
I blushed deeply. I don't take compliments well at all, and I never know what to say. "Oh, sorry. I really don't think so. Oh my... goodness," I stammered.
"Don't be shy honey. You really are beautiful," she leaned in offering her hand. "I'm Penny," she said. "What's your name?"
"I'm Jessie. Jessie Walton," I said, taking her soft hand in greeting.
"Hi Jessie Walton!" she said. "It's very nice to meet you. Shame you got stuck with the night shift. Someone like you, you should be out on the town having fun with your boyfriend!"
"Ha ha, oh, I don't have a boyfriend," I said nervously. "Besides, I like working evenings. It makes it easier to save money if I'm working instead of spending!"
"Great theory honey, I know exactly what you mean. In fact, I'm working now too."
"Oh, what do you do?" I asked with genuine curiosity. She didn't look like someone doing any kind of work.
"Well I guess you're not so shy after all with a question like that!" said Penny.
"Oh my goodness, I'm so sorry! That was so rude. It's really none of my business. I'm so sorry Miss Penny."
"Jessie, relax babe. You might be just what I'm looking for actually! Tell me about yourself!"
