The Society

byBarno©

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living in a room above a tailor and sewing shop in the center of a quaint old town surrounded by mansions. I worked for a catering company on the weekends as a second job to help make ends meet. It was a Saturday night right in the middle of the rather busy social season in this upscale town. I was working at a catering company hauling racks of glasses from the catering truck to a massive bar set up behind a rather large mansion.

It was a summer party at one of the ridiculously wealthy estates. It was getting crowded when I first noticed her. There were about a hundred and fifty well dressed people on the expansive back lawn and while there were more than a few gorgeous young women dressed in tight fitting summer dresses this one woman stuck out. I figured that she was in her late forties, but it would be easy to miscalculate that number into a woman in her late thirties considering how attractive she was. She was wearing a dress that may have been inappropriate for a woman her age but looked fine on her. It was both backless and sleeveless. In fact all there was to the top was a sort of tight halter that covered a pair of large but very firm breasts and a sort of dress shirt collar that wrapped around her neck. The dress length was to about mid thigh which was just fine with her legs. I watched the dishwater blonde move about the party as I worked for the bartenders. It took an hour but I figured it out. The dress was just fine. It was the body that didn't match the woman's age. She was the most gorgeous woman I had ever seen.

There were a few times that she was close enough while ordering a lemon flavored tonic water or just standing by the bar and talking that I could see how smooth her skin was, the total lack of wrinkles on her face, the full lips, big dark eyes and then there were the legs. She was a tall woman and the legs seemed to take up most of her. They had a muscularity that told me she did more than just walk her dog for exercise.

I had been staring at her all night. There were plenty of other girls closer to my age that were drop dead gorgeous roaming about the party but there was something about this mature beauty that was driving me crazy.

At one point I ran into someone I knew. Jill was a tall light brown haired girl I had gone to high school with. She was a couple of years older than me and had been extremely popular and had dated a popular athlete. Suffice it to say that I wasn't really a part of her life until now. I noticed her walking up to me from across the lawn. I averted my eyes and pretended to work on putting the dirty glasses into racks so that she wouldn't think that I was staring at her. It wasn't easy. She was wearing a classic black dress and black high heel pumps and she looked better than she did in high school.

"Hey are you Dennis Heyquist from Millsdale?" She asked from the other side of the bar.

"Ugh yeah. Jill? Is that you?" I did my best to pretend I wasn't sure it was her. Still she was different. I was used to seeing Jill in jeans and little or no make up, a natural beauty. Standing there with her hair up wearing the tight fitting wrap around dress she was so much more mature and sexy.

"Yeah it's me! It's so nice to see you!" She shouted over the cries for vodkas on the rocks.

"Hey yeah it's sure nice to see you. How'd you land here amongst the rich and famous?" I smiled so that she knew that I was kidding her but I couldn't help wondering how she had ended up at this party.

"I work for Jodi Mapleton as her assistant. This is her party." Jill gave me one of her ten thousand watt smiles.

I was shocked to be getting such a warm greeting from Jill. We may have said hello three times in four years of high school. One of the bartenders gave me a look and was about to tell me to get back to work but when he saw the quality of the girl I was talking too he gave me a break.

"You're busy now. Maybe we can talk later." Jill concluded as the party and the drinking had hit a peak.

"That'll be real nice." I watched Jill walk away. She was 5'-8" with a lithe athletic body and long toned legs. Just by agreeing to talk to her after the party I was playing way above my pay grade.

I went back to work. I jogged out to the van for the last two racks of wine glasses. If we were lucky they along with the ones being washed in the house would be enough for the rest of the party. While I was making my way back to the bar I noticed the commotion happening right in front of my station. The gorgeous blonde had squared off in what looked like a verbal confrontation with a younger blonde haired woman I hadn't noticed before. The new guest was about Jill's height but with a much more athletic build, her arms and legs were sculpted with muscle but not overly so.

The young blonde was animated and angry to the point of being out of control. Meanwhile the woman I had begun such an infatuation with was smiling and fielding every verbal jab or accusation with the deft agility of a matador waving her cape at a charging bull. She was calm, confidant and obviously winning the argument which from what I could tell was about the younger blonde who was named Serena accusing the older darker haired blonde of stealing something from her. It was starting to gather attention from the other partygoers until two men stepped between them.

After all the excitement done high society style the five hour cocktail party went quickly. It always went that way at a catering job, keep your head down working and time flies. Before I knew it wealthy people were filing out and Mercedes, Land Rovers and Porsches were pulling away. The daylight was fading and the people were probably off to dinners at any of the high end restaurants located in this wealthy town.

I was cleaning up at the bar when she came right up to me. I looked up and nearly melted. The two bartenders were standing away from the bar so there was no one to save me from her, her devastating beauty and as I would find out her ability to persuade and ultimately dominate another person.

"I was wondering if I could get a chardonnay?" Her voice was deep and very crisp.

"Oh yes. Sure. We're technically not supposed to be serving anymore but that's okay." I answered nervously.

"Well I appreciate the favor. Actually I have become quite fond of the vineyard you are serving but I wanted to wait until you were pouring to order my first of the evening." The dishwater blonde's red lips parted exposing a perfect set of brilliantly white teeth.

"Really? How come?" I asked with a baffled expression. I couldn't figure why anyone would care who poured them a glass of wine.

I turned and reached for the bottle resting in the ice and a clean glass. I was nervous. The mature woman was still flawless up close and very intimidating. She was gorgeous. I could feel her looking at me with my back turned and the goose bumps began crawling up my back.

"I'm a sucker for a cute boy with bright blue eyes." She was smiling like some sort of predator when I returned with her glass of wine.

"Thanks." I replied.

"Nice smooth skin too, very pretty." She took the glass from me. The well built woman seemed to purposely wrap her fingers around mine. The sensation sent shivers right through me.

"Thanks again." I wanted to say something about being called pretty but this woman could have spit on me and I would have taken it.

"My name is Catherine Creeler. It's a pleasure to meet you." The tall blonde reached out her hand and when I took it she gripped mine hard.

"I'm Dennis Heyquist. It's very nice to meet you Ms. Creeler." I replied getting more comfortable in her presence.

"Well you can call me Catherine. I'd get very tired calling you Mr. Heyquist, so . . ." Catherine Creeler was smiling broadly at me with the same predatory look.

"That's fine with me." I chuckled nervously.

"Dennis I was wondering if this was your only job? Maybe you'd be interested in making some extra money?" She inquired.

"I'd be very interested in making extra money. I'm working so that maybe I can take some classes at the community college." I admitted.

"Well I have some yard work that needs to be done at my home. I was hoping to get someone over this week." Catherine told me.

"I can be over tomorrow at nine." I told her anxious to have a job and with such an interesting and sexy woman.

"That's excellent. I like a go getter." She exulted.

With that Catherine turned and walked back over to the small group of people that remained. I couldn't help admiring her legs. They were long and toned with muscle and the high heels she was wearing just made those muscles bulge in all the right places. In short her calves were magnificent and the way her upper thighs and ass pressed against her dress I knew they were just as beautiful.

Just when I thought I'd never be able to take my eyes off of Ms. Creeler Jill walked up to the now cleaned up bar area. Like Catherine Creeler she had no problem filling out the very revealing dress that she was wearing.

"Hey how's it going?" She asked with a smile.

"Tired." I replied wiping sweat from my forehead.

"Yeah it's gotta be tough work hauling those glasses around in this heat. I'm glad that I ran into you though." Jill smiled at me.

"So what are you doing here?" I finally got to satisfy my curiosity.

"Well like I said, I work for Ms. Mapleton so she likes to have me here at these parties to help greet the guests some of them are clients." Jill was sufficiently vague but I didn't care she looked beautiful and I was transfixed.

"This is definitely a nice place to work." I was impressed but not surprised that someone with Jill's personality and looks had ended up in this type of situation.

"Yeah. I live here now too." Jill's eyes gave me a quick once over.

"Not a bad deal." I added with a smile.

"It works for me." Jill laughed. "Hey we should go out for drinks sometime."

"Sure I'm up for that. How about Sunday? That is as long as you don't mind hanging with a struggling caterer." I joked trying to cover up the unbelievable luck of having snagged a date with Jill Wiggler.

Just then Ms. Mapleton came up to the bar. She was also a very sexy mature woman who looked to be in her early forties. She was wearing a red satin dress that highlighted a set of perfect tits. She had stylish dark auburn hair and blue eyes that seemed to blaze back at me. Like most women at this party she was quite fuckable.

"So Jill this is your friend." Ms. Mapleton gushed as she stepped up beside her assistant.

"Yes Jodi Mapleton this is Dennis Heyquist. We went to high school together." Jill's demeanor stiffened a bit when she introduced me to her boss.

"Hi Ms. Mapleton. It's nice to meet you." I shook the pretty woman's hand.

"Well first things first please call me Jodi. Secondly Jill was right. You're very sweet. Jill you'll have to ask your friend over for a swim this weekend." Jodi's eyes roamed over my body just as Jill's had and Catherine's before her. It was something I wasn't used too.

"How about it?" Jill asked me.

"It'll have to be Sunday." I replied barely able to contain myself.

"Sunday it is. Nice to meet you Denny." Jodi gave me a big smile and walked away.

"See ya Sunday sweetie." Jill leaned over the bar, gave me a kiss and the followed Jodi back towards the mansion.

As soon as I got home I jumped into bed and masturbated. I couldn't help it. All I could think of was fucking Jill and when I made a mental picture of her riding my fat cock I got as hard as I had ever been. I couldn't wait until Sunday. I figured I'd work for Catherine on Saturday make some cash so that I could take out Jill on Sunday after watching her bounce around all day in her bikini.

I rode my bike over to Catherine Creeler's home in a tee shirt, jeans and work boots. After all I was expecting to be in the bushes most of the day. The directions she had given me put her home about five miles from my apartment, actually just down the road from the Mapleton estate. When I turned the corner to her street I figured I was reminded how far I really was from this neighborhood, a million miles. The Creeler residence was in a row of estates located on a long private road. Each estate was on multiple acre plots of land, many with barns, stables and horses. I checked in with the security guard at the top of the road and then pedaled down to the number Catherine had given me. It was a large federal with pillars in the front of the home. The property was enormous with a large front yard that was so big that it was hard to see the home from the street behind a row of trees. In fact the house was so set back I felt as if I had ridden as far down the long driveway as I had the distance from my apartment.

I should have turned around right there. It just didn't make sense that a woman in this sort of position would need me to do yard work on this sort of estate. I wasn't sure what Catherine Creeler had in store for me but I was certain that just cutting the lawn took a team of men quite a while to get done. Despite a rising apprehension I couldn't resist the chance to get another look at Ms. Creeler. What if she was wearing another short dress or skirt? I rode up to the huge home and leaned my bike up against one of the pillars. I thought about trying to hide it a little better then figured what the hell for? I stepped up to the door and pushed the bell. I could hear the chimes ring loud and clear behind the door. I waited for a minute and almost rang the bell again but stopped. It had been loud enough to wake the dead so I knew that if someone was home they'd answer the door, besides I didn't want to seem anxious. There was no other way to put it, Catherine Creeler intimidated me.

Suddenly the large heavy door opened and standing there was a tall well built blonde haired woman. I thought it may have been Halloween. She was wearing a French maid outfit and a pair of black high heel pumps. I had never travelled in these circles but I was pretty sure that none of the normal multimillionaires in this neighborhood had a woman who looked like this, dressed this way answering their door.

"Hi I'm here to see Ms. Creeler?" I said in a shaky voice.

"Of course, you must be Dennis." The broad shouldered woman replied with a smile and a voice that seemed too feminine for a woman of her build. "Why don't you follow me?"

I watched her spin on the shiny shoes and walk through an enormous foyer. Her bare tan legs were wrapped with muscle yet long and sculpted like those of a female athlete. Her uniform was backless and I got a great view of the muscles rippling around her shoulder blades as she moved. It was obvious that she must have gone to the same gym as her boss. And when she turned and smiled as we walked through the living room to the back of the house. I could see that she was just as beautiful and as sexy as Catherine Creeler.

I followed the blonde Amazon to a room that overlooked a large stone patio that was part of a expansive pool area and then a massive back lawn that swept down to the ocean below. To one side was a barn and stable set off from the mansion. Standing by one of the huge windows that stretched from just above the floor to the ceiling that opened up the house to the beautiful scene was Catherine Creeler. She was looking out the window drinking a glass of orange juice. She was wearing a peach colored dress that clung to her tall body in all the right places and went down to just above her knees. The shiny black high heel pumps matched the thick black belt that wrapped around the dress at her waist and accentuated the long toned legs.

"Why hello Denny! I'm so glad that you were able to come." The dishwater blonde held out her hand and I shook it.

"Oh sure like I said, I'd love to get some steady work." I replied with hopes of doubling my catering company wage dancing in my head.

"You've met my assistant Corinna. Corinna we'll be downstairs." Catherine told her.

I smiled at Corinna and she smiled back at me as she took the juice glass from her boss. Then I followed the click of Catherine Creeler's heels as they made their way across the marble floor to a staircase off to the side of the huge room. I couldn't help but keep my eyes glued to her legs. I was trying to decide whether it was the lady of the house or her maid who had the nicer ass and legs when I looked up and saw Catherine pausing at the top of the stairs smiling at me. I had been busted checking out my new boss' legs. I was a bit horrified but when our own eyes met Catherine's smile simply widened and then she continued down the stairs to the basement. I thought about it and figured that the statuesque woman must have been used to the ogling by now.

"We have five main rooms on the lower level. One is a workout room here on the right with two servant rooms behind it, at this end the door leads out to our patio and pool area and here at the other end of the hall is a doorway to a lounge area, this other room here on the left you'll see soon enough." Catherine pointed to each room as we walked.

The gym was as big as a commercial facility. Meanwhile the mysterious room opposite the gym was locked up and cordoned off with a heavy door. The lounge room was at the end of the long hallway. Catherine opened the door and we stood at the entrance of the room which was dark even after she turned on the lights. There was a large bar with stools off to the side and a number of couches facing a large screen.

Catherine led me into the lounge. She walked up to the front of the room. I followed her up and looked over the large screen in front of us. I got a weird vision of Catherine and her guests settled in here watching a movie while Corinna served them popcorn.

"Why don't you come up here with me Denny? I want to watch you take off your clothes." The blonde said as she reached down and undid her belt.

"What?" I gasped. Sure I wanted to fuck the mature sex bomb but did she actually want to screw a skinny nobody like myself? I mean first Jill Wiggler making passes at me and now this? It was too good to be true. I had no idea how right that thought was.

"Come on now Denny, I've got a 60 acre estate here. You really didn't think I was going to hire you to rake the leaves did you?" She chuckled as she slid out of her dress exposing a black lace bra, panties and garter belt that attached to sheer stockings.

"What do you want me to do?" I asked in an incredible display of naivete.

"Well for starters I'd like to have you on your knees licking my pussy." She was so much taller than me in her stiletto heels that she had to lean down when she stepped up and kissed me. "Do you think you could do that for me?"

"Oh God yes!" I gushed as I fumbled out of my clothes and watched her take a seat on a front row couch spreading her long legs wide.

"Ah yes I see that I was correct at the party. You are quite well endowed and uncut too. What a lovely surprise." She pointed at my exposed semi erect penis.

"How did you know something like that?" I had a cock that was a little over eight inches long and pretty thick and I was curious how this horny slut would know this from only a chance meeting at a party.

"Let's say that after a number of years I've become quite the connoisseur of bulges and yours was quite exquisite last night." The dishwater blonde laughed heartily. "Now get on your knees and show momma what you can do with your tongue."

I followed her order to a tee. I scrambled down to my knees, placed my hands on her thighs and leaned in and gently began licking at the pouting lips of Catherine Creeler's genitals. I moved up and down on each lip. I felt her quiver above me so I did it again. I ran my hands along her thighs. I couldn't believe how hard with muscle they felt. She was in incredible shape. I kept licking and soon I was tasting the oozing lubricant. It quickly went from a drool to a pumping gush of warm, thick fluid and I felt the muscles in her legs flex as her pelvis began lifting off the couch.

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