I'm convinced that people watching is one of life's greatest and simplest pleasures. There is as much entertainment in seeing a variety of human behavior walking past as there is in the fashion displayed in a variety of human shapes and sizes.
The day had been long and I was enjoying a light dinner at an open café in the hotel. Dining alone on business trips was not unusual and sometimes the peace and quiet of the meal helped wind down the day. Plus, one always had to be careful about extending dinner invitations to anyone associated with the company you were calling on to prevent the appearance of impropriety.
The scenery tonight was a mix of late day tourist and early evening diners. The casual dress of the day for many was soon to be replaced with a change of dress to the more formal. This was more obvious with the older set than youth. While the ladies of my generation (of the 50's and 60's) had casual blouses and walking slacks, the youth had on black jeans and t-shirts with a variety of body jewelry mixed in. While the tightness of the youthful shape is always appealing to the eyes, the maturing that comes with the older models often makes for a more desirable experience.
"Can I get you anything else?" My waitress was an attractive brunette that was probably in her mid-30's. Despite coming across strangers all day long, she did have a warmth to her that made the meal more enjoyable.
"No, it was very good and I just need the check now, please." While she was organizing the folder with my bill in it, I asked her, "By the way, would you happen to know of a bar here in the hotel that is open like this?"
"Are you looking for a particular type of bar or just someplace where you can people watch" she asked.
"Mainly people watch. Quieter is better but I doubt if I will be there long enough for that to matter," I said.
"There is a lounge called 'Sunset' just around the corner. Should be just what you are looking for.
I thanked her and checked out her ass as she walked off. It had a nice shape and sway, considering you really can't tell much in restaurant skirts. At my age, women who are polite and interesting don't have to have the perfect body any more. The intellectual and conversational thing becomes just as important.
"Sunset" was busy for only 7 pm so I grabbed the last seat at the bar, facing the courtyard.
"Is this seat taken? I asked. The man on the left just gestured for me to help myself and the woman on the right responded, "It's yours for the taking."
After my bourbon and water came, I took a quick sip and heard the woman say, "Long day?"
Somewhat surprised to have a woman open up a conversation in a bar with me, I replied, "Well yes, does it show?"
"Not too badly. Just thought you might be like me and be grabbing that unwind cocktail before calling it a day."
Over the next half hour I learned her name was Victoria, she was from Chicago, in her mid-forties and had only been in LA for the past two days, going home the day after tomorrow. For her this was a long trip and she was ready to go home.
"So you like to people watch, do you Harry?" she asked. "What do you find most interesting or should that be obvious to me?"
"What do you mean obvious?" I said.
She dropped her voice slightly so as not to be heard beyond the two of us. In doing so her blouse opened to the point where I was now paying attention to her figure as well as holding a conversation. The swell of her breasts was apparent as was her white lace bra.
"I figured all men just checked out boobs and butts. The hotter the figure, the more they drooled."
"That was certainly true when I was younger," I said. "But now I focus less on the figure and more on how adventurous I think the person is. You know, the person they only let out when in private surroundings."
"Hmmmm," she said. "So you look at a passerby and do a little fantasizing at the same time it sounds like."
"Now that you put it that way, that's pretty much it," I said. I noticed Victoria now looking at me directly into my eyes and smiling. She was an attractive woman, blue eyes, full face, shoulder length brown hair, all of which was highlighted by the typical dark suit of a mid-west business person.
"So, pick out someone walking by and tell me what kind of fantasy you are thinking of," she said.
"I couldn't do that here in public, I'd get arrested." I turned my gaze back to the passersby to see if she would be offended, neutral or more interested.
"Would you tell me if we were in a more private place?" she asked.
"I don't know. Sometimes the details are graphic. I wouldn't want to offend you."
"Believe me I have heard it all, it would be hard to offend me. I know a place where we can continue this conversation if you'd like to join me?
"Lead the way," I said.
We both downed the last sip of our drink. Victoria slipped out of her chair and started walking through the bar out to the main lobby with me following. She had the figure of a middle aged woman but with a tight waist line and generous ass. My first thought was how it would feel to fuck her doggy style, holding on to that skinny waist while bouncing my groin off those generous ass cheeks, then shooting my cum all over them.
Busted! Victoria looked over her shoulder to see if I was following her and caught me checking out her ass. She just grinned and kept walking.
Into the elevator we went with several others, not a word said. She looked at me with a quizzical look and then put her hand on the button panel. Realizing she wanted the number of my floor, I told her "12 please". We got off on the 12th floor and she followed me to my door. As I opened the door, I gestured for her to enter, ladies first.
"Is this a private enough place to finish that conversation?" she asked setting her purse down on the bed..
"I think so," I said.
"Do you mind if I get rid of this?" she asked. Victoria took off the jacket to her business suit and hung it up. Meanwhile, I found a light jazz station on the clock radio just to take the edge off the room.
"Make yourself comfortable," I said and proceeded to make us each a drink from the room's mini bar.
She started to kick off her dress shoes but I stopped her. "Could you do me a favor and leave those on? I asked.
With a knowing smile she said, "If you like. But I do need to get rid of these pantyhose. I'll be right back." With that she stepped into the bathroom.
In the meantime I hung my coat over one of the chairs in the room and kicked off my shoes. There was hard liquor in the bar but I chose to pour us each a glass of white wine.
Victoria came out of the restroom. I watched her breasts bounce gently under her blouse as she came to me, got her glass of wine and held it up. Looking me in the eyes she said, "Cheers!" We each took a sip of wine and continued to inspect each other.
Victoria raised her right hand and started rubbing it over my chest, as if checking out the contour of my muscles. In return, I placed my left hand on her waist, rubbing her lower back and encouraging her to come closer.
"I have an idea," she said.
"What's that?"
"Rather than talking about fantasies with strangers, why don't we act out our own? Since you have so many fantasies, I'm sure you have one you have always wanted to act on but never had the opportunity. This might just be the time."
I looked at Victoria and replied, "Are you sure? It would probably involve games and nakedness and lots of dirty talk, etc. Might be more than you want to tackle...." While I was really hoping she would be interested, I was also cautious that she didn't start something she couldn't finish.
"Oooooh, I think I can handle it," she said looking into my eyes.
