People Watching

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.

I was pretty sure she was game but I had to make sure she wasn't bluffing. Taking my hand off her waste, I took her right hand and gradually moved it down to my crotch so she was holding my cock.

I did not have to wait long for her reaction. She smiled and started stroking my cock through my pants.

"Ummm, you must like my idea, your cock is already hard! Do you want to fuck my pussy with that hard cock from behind?" she asked.

I must have had a surprised look on my face as she grinned and said, "See, I don't mind dirty talk, and nakedness and stuff. Plus I saw you checking me out when we left the bar. Now, want to share that fantasy?"

"OK," I said. "I've always wanted to play strip poker with some special rules."

"And those rules are......?" she asked, as she took another sip of her wine, but not letting go of my cock.

"Winner gets to decide what loser takes off. Winner gets to decide who takes it off. Winner can kiss any part of the losers body that is not covered by clothing or can have the loser kiss them on any part of their body not covered by clothing. Every round ends with a kiss to keep things friendly. First one with no clothes has to be a slave to the winner for 30 minutes, nothing kinky but no balking. Still interested?" I looked into her eyes while waiting for an answer.

"Sure, it will be fun to have you as my slave for 30 minutes, Harry. But we have no cards."

"You refill the drinks and I'll get things set up," I said.

We sat across from each other at the small desk. It was decided we would play hi-low with one draw each hand with numbers written on slips of paper.

Victoria was staring at my crotch and said, "Not yet." She proceeded to cross her legs, purposely opening them to show me her white panties and then pulled the hem of her skirt up until two thirds of her legs were showing.

"Now I'm ready. Hope you aren't too distracted," she said with a sly grin.

"Oh I'm definitely distracted but in a very good way," I said. "Ladies first....go ahead and draw."

Victoria pulled a slip of paper from the envelope and showed it to me. It said "4".

"Your turn," she said.

I reached into the envelope and my slip of paper read "6". I showed it to her.

"Looks like you win the first round," she said with a smile. "What do I take off?"

I looked at Victoria and said, "I want to take it off and I think I'll start with your skirt. Stand up for me and turn around."

"Yes sir," she said in a very playful tone. She stood up, turned around and held her hands clasped in front of her. Her skirt dropped to its normal length, falling just above the knee.

I reached up, undid the button and zipper and gently pulled the skirt down until she was able to step out of it.

Victoria started to turn around and sit but I stopped her. "Wait," I said, "I still get to kiss you wherever I want."

Sounding a little confused, she looked over her shoulder and said, "OK, go ahead."

Placing her skirt folded on the bed, I ran my hands up the back of her thighs and gently raised the bottom of her blouse to waste high. She shivered a bit with the path my hands were taking then stood quietly waiting to find out where I would kiss her.

Victoria had white boy shorts on that did a fabulous job of highlighting the roundness of her ass. After taking in the picture for a moment, I planted a nice wet kiss on the inside of both thighs, just under her pussy.

"I think that was two kisses," she said, sitting down. "But I will forgive you this time. Now do we still kiss before the next round?"

"Absolutely." With that we leaned in to each other and gave each other a light French kiss.

"We need to improve on that next round," Victoria said. ""Your turn to go now."

While I selected my slip from the envelope Victoria continued, "For a guy who likes dirty talk, you are pretty mellow."

"I've been holding back so I didn't offend you but I can change that," I said. Then holding up my slip I showed her and "8".

Victoria reached in for her slip and pulled out a "2". "Shit! Ok, what goes now?"

I smiled at her and stared at her legs again.

"I think it is time I found out how you like to shave your pussy. Stand up facing me so I can remove your panties," I said.

Victoria stood up with her arms crossed on her chest. Again I ran my hands up her legs from the knee to her waistline.

Shivering she said, "That's cheating you know."

"Getting a little excited are you?" I asked.

"Just wait til I get my turn!" she said in a competitive but joking tone of voice.

I placed my fingers in the waistband of her panties and started pulling them down. When they were half way down I told her to hold her blouse up so I could see better. She pulled her blouse up to her waste line and held it there for me.

I continued to pull her panties down, revealing a lush bush of hair, reaching from hip to hip and moist around her pussy. As I had her step out of them, I was careful not to get them caught on her heals. Once in my hands, I held the crotch up to my nose to get a gentle whiff of her pussy scent. She just watched with a grin on her face.

"Have a seat and spread your legs wide," I told her.

Victoria sat but only slowly parted her legs, knowing my eyes were ready to take in the full view of her exposed and wet pussy.

Once spread, I got on my knees in front of her and gave her pussy a lick from the bottom to top, with a short kiss on her clit before returning to my chair.

"Again I think you cheated. That was more of a lick than kiss," she said.

"Complaining?"

"Not a bit. In fact, you'll be licking my pussy a lot more when I win this game."

"Oh, I'll be licking you all right," I said, "just before I roll you over and give your pussy a good fucking."

Victoria moaned at that comment and reached forward to provide her side of the end of the round kiss. This time it was deep and wet French kiss that lasted a full 15 seconds.

Sitting back in her chair, Victoria crossed her legs and straightened her blouse so as to provide as much coverage as possible to her present nakedness.

"A little self conscious about being naked?" I asked.

"Not at all, Harry. Just don't want you to be distracted and blame me when you lose the game," she said smiling.

"Well I think I want to be distracted, it won't bother me at all. I think you should open those legs back up so I can look at what I have won so far whenever I want."

Partially miffed yet partially excited, Victoria spread her legs, knowing just when to stop so that I could get my view but she was not widely on display.

The next slips of card were pulled with Victoria getting a "10" and me a "3".

"Ok, Harry, stand up and drop those pants. You do it and I'll watch."

And watch she did. Her eyes started on my crotch and never left them the entire time. Once I returned to my seat she got on her knees in front of me, with her hands on my thighs.

"Spread real wide so I can...." As her voice trailed off, Victoria reached down with her tongue and licked the inside of both of my thighs, then licked my cock all along its length through my underwear, kissing the head.

"Kiss?" she said and gave me our end of round French kiss before returning to her chair, only this time with her legs spread as before.

"Keep you legs spread, too," she said staring at my crotch. "I'm going to get a good look at your cock real soon when I win this next hand."

We both broke our gaze long enough to pick our next slips. Victoria pulled a "6", I pulled a "7".

"Guess it's the blouse, huh?" she said.

I nodded and she started to undo the buttons. Glancing back at me she confirmed I wanted her to complete he process alone. Once done she was sitting clad in only her white lace bra, with her dark brown nipples now clearly visible.

"Ready to be shocked?" I asked.

"Sure," she said with a challenging look.

"I want you to stand up, turn around, and bend over the chair so I can kiss you."

With a grin, Victoria figured I was going to give her pussy a lick again only from another angle. She bent over but not far enough for my needs.

"Farther, so that your back is almost flat."

Victoria did as I requested. I got on my knees behind her, placed one had on each buttock and pulled her ass cheeks apart exposing her little rosebud. Before she figured it out, I began tonguing her asshole.

"Oh!" she said. I couldn't tell if she was surprised, disgusted or enjoying it. Nonetheless, I gave her asshole five good licks, mostly in circles before I stopped and backed away.

"I didn't expect that."

"Haven't you ever had that done to you before?"

"Yes, but I didn't think you were the kind of guy willing to do that."

Sensing that ass play was OK, I wanted to see how much Victoria was game for.

"Are you willing to do that to me? I might be asking you to when I win the game......"

Victoria looked at me smugly and said, "I might ....but you haven't won yet."

"Do you like being fucked in the ass? Or is your ass a virgin?" I was curious what she would tell me and how far she would go with this topic.

"That's for me to know and you to find out. Besides, it might be you getting fucked in the ass later...."

I was curious about that comment but left it alone for now.

She again sat down with her legs crossed and with a waive of my hand I indicated she should sit with her legs spread so I could look at her pussy whenever I wanted. Before adjusting herself she stood up and began walking to the bathroom.

"I need to put a towel under me or I'm going to make a mess on this chair." Another moment I was hoping for came to pass---watching this lovely woman with the full ass walking away from me in her heels and then coming back as well, breasts bouncing and pussy in full view. Just what the voyeur in me needed. I'm not sure my dick could've gotten any harder and she knew that by looking.

Victoria spread the towel over the chair and sat back down, this time with legs spread. With only her bra left, I stated the obvious.

"Looks like I need just one more win and you're mine for the next half hour!"

"It's not over yet," she said pulling a "9" out of the envelope, much higher than my "2". "Stand up and come over here."

Victoria spread her legs wide inviting me to stand in the middle of them, very close to her. So close my crotch was in her face.

"Now, don't say a word while I get rid of your underwear, OK?" With that, she used her right hand to give me a smack on my ass as a way to emphasize the command.

With hands at my side I just looked down and watched. Victoria looked up at me briefly, grinned then stared directly at my cock as she slowly lowered by underwear.

As she pulled my underwear all the way down in back, she placed one hand on each cheek of my ass and began squeezing. She continued this on and off while placing her teeth on the front of my underwear and continuing to pull them off.

At this point my cock was so hard she could not get the front of underwear off without using her hands. Pulling my underwear out she released my cock out into the open and watched the underwear fall to the floor.

"Remember....don't move...." She repeated.

With my cock level with her face, she returned her right hand to my ass check and began squeezing again. With her left hand, she gently took hold of my cock and moved it to the side. Once my cock was out of the way, she gently placed her mouth around my hairy balls and started sucking them.

While the warmth of her mouth around my balls was incredible to say the least, she also did this massaging motion with her tongue at the same time that just about made me go through the roof.

She further compounded the pleasure by now gently and slowly stroking my cock with her left hand, up and down, and periodically just on the head. The pre-cum was starting to ooze out.

"This is wonderful but you need to stop," I said, "or this game is about to be over."

Releasing my balls Victoria just stared at my cock and said. "I guess I'll just have to wait to continue this when I win the next round. Now give me a kiss."