Babysitting for the Winstons

Babysitting for Winstons

By ShamBaLa

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This is a work of fiction.

Any resemblance to actual locations or persons living or dead is purely coincidental.

All characters are 18 or older.

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I hated babysitting. My folks would volunteer me occasionally to sit for their friends if they came up dry on a night they wanted to themselves. I hadn't been a sitter for a couple years. High school graduation was less than two months away and I had other things to do on a Friday evening.

Were I grew up in the 60's the school year ended in mid-June. I could never figure how the school system determined your kindergarten placement age. My birthday was in early May, so I turned 17 a month or more before most of my friends which meant I got to drive before them as well. Senior year I was 18 for the last seven weeks of school and my thoughts were on college, a girlfriend and planning a summer trip to Europe. Definitely not a babysitting gig.

"Sweetheart, we really need a favor from you," my mother implored. "The Winston's can't get a babysitter for tonight and they asked us to go to an important event with them in the city. Would you be a dear and babysit for their daughter?"

"Mom, I was kinda supposed to meet up with Diane at a party over at John's place, it..."

"I know, I'm sure she'll understand a family emergency. I'll even talk to her if you like. Look Kate is eleven, it besides they'll pay very well for being last minute and you need more money for the Europe trip," Mom finished.

"Geeze where are you guys going?"

"Steve, you know Mr. Winston is using this reception to make some bigger contacts that can help his business," Mom had that pleading look just before it becomes an order. "It's important to him and it might mean new contacts for your father as well."

The Winston's were fairly recent friends of my parents. They were way wealthier than we were, probably twenty-five years younger and owned some kind of company that supplied components to big electronic companies. I didn't remember they had a daughter.

After making the awkward call to Diane I changed into jeans and a grey pocket t-shirt and headed to the Winston's. There place was gorgeous. It must have been 5,000 square feet with a three car garage, a pool and a sauna in a detached bath house.

I had met them briefly when they were over for the dinner parties my parents hosted every few months. If I passed them on the street, I wouldn't recognize then, that's how fleeting the encounter was.

I rolled up in my third hand Toyota and parked next to a low slung white amazing looking sports car with a yellow emblem and black horse. A Ferrari. I stood at the door ready to push the door bell. Next to the door was a wood sign proclaiming "The Winstons Live." Hanging under it were three pineapples also cut from wood and nicely painted. The two on either side were upside down. I thought it odd at the time. Just as I reached for the door bell Steve opened the door. He had an expensive haircut a tailored tux.

"Man am I glad to see you. You pulled my chestnuts out of the fire. I mean that. If things work out, you have a guaranteed summer job when you go to college; you ARE going to college, right?" It was all one run on sentence.

"Oh, yes, I'm going to the engineering schools at..."

Victoria appeared from a dark hallway to the left. Ready for a fancy evening, her dress showed off her smoking hot body. The hem of the dress was a series of V shaped sections about eight inches high. The general line was like a min skirt in the front but flowed to mid calf in the rear. At the same time Kate raced in from the living room on the right.

"Kate honey this is Brad, he is the son of one of our very good friends." Victoria tried to continue.

"Where's Carol or Stephanie? I love it when they sit for me - even though I'm not a baby," Kate sneered and gave me an evil eye.

"Look, be on your best behavior for Brad. He's a nice guy and will make an amazing ice cream sundae for you later," Victoria said as she bent down to hug her daughter and kiss her good bye. Although she didn't have to bend very far. Kate, and whatever she was, 10 or 11 was nearly as tall as Victoria and entering the awkward tweenage years.

It was in this moment I caught a glimpse down the deeply cut neck line of her black evening dress. I don't understand fabric, but this was black with lots of deep folds, but there was a light sheen over it of deep blue material that sparkled as she moved. The fabric gathered to a point at her shoulders.

And when she turned to get the matching half jacket I realized it was a halter dress and her back was bare nearly to the top of her buttocks. It was a stunning sight. I tried to regain some focus and listen to the final instructions for bed time, ice cream and the pool.

"Ohm it's a hot night. Let Kate swim for an hour or so. Then ice cream, then bed," Victoria empathized that word as she turned toward her daughter.

"Oh sure, I'm sure we'll get along just fine, " I said trying to sound responsible.

Steve reappeared through the front door and looked at me then his wife. He didn't say a word.

"OK, I'm on the way," Victoria said as she moved to the open door. Steve looked at me and rolled his eyes then blew his daughter a kiss.

_______________________

Kate's bedroom was up stairs and her parents master suite was on the first floor with big windows opening onto the patio by the pool. I think it was called a California layout.

Kate had blown down the stairs, dropped her towel and dove into the pool. I took a seat in a chair and took in the night sky and the very cool indirect lighting in the plantings.

"Why don't you come in?" Kate asked.

"I don't have a suit. I didn't think I would be swimming tonight. Sorry."

The hours before bed time passed uneventfully. A little TV, time for a swim. I threw plastic rings into the deep end which Kate gleefully dove in to retrieve. Over and over. Then a collaborative effort to make a banana split sundae for each of us.

Kate headed up stairs get ready for bed and be more or less on her own.

"No, you don't have to read me a bed time story, but Mom lets me read a little before I fall asleep."

"Ok, but I'll look in on you in forty minutes or so and turn your light off, OK?"

"Cool."

Half-hour later her light was already off and I settled in for the rest of the evening. The house was amazing in my limited experience with upscale homes. Off the living room and one step down was a den of sorts. A pool table with red felt dominated the room. Big over stuffed leather chairs were arranged in a conversation area. A beautiful wood and chrome bar filled one end of the space.

I spent some time looking at all the bottles and was tempted to practice being an adult and fix a drink but thought better of it. I looked at all the glasses. Some short tumbler looking things on a shelf. And what took to be martini glasses hanging from an overhead rack. I took one down and in my 19 year old, permanently horny mind, decided that the shape was just like Victoria's breasts. I had a momentary fantasy of pressing the glass against her naked breast and watching the nipple squished into the bottom of the glass.

Off the den was a half bath and I needed to use it. It was as upscale as the rest of the house. While I was relieving myself I noticed a stack of magazines next to the toilet. Right on top was a Playboy. After I zipped up I started flipping through the stack. They were all Playboys and a sprinkling of Penthouse. Holy shit, I was in heaven. Provocative women all over!

I sat on the lid of the commode admiring the Playboy and Penthouse pictures and had a hard on straining against my jeans. Then I discovered the letters section of Penthouse. I was hooked. The vivid descriptions and detail in the letters clearly influenced reading and writing erotic stories later.

It was like an overdose on drugs and I had to stop before I came in my underwear. I committed images to memory so I could jerk off to them later.

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I lost track of time and quickly put the pile back trying to remember which issue was on top. I did think it was a little weird that the magazines were out in the open, especially with a ten year old daughter around. I guessed that as an adult you can do with you want, but any sex magazines or pictures I had accumulated were carefully hidden away.

Time past. It was pushing 11 and I had the local news on the TV for lack of anything else to do. I should have bought a book. I heard the garage door open and the door from the garage to the laundry room open so I got up and crossed to the kitchen to greet the Winston's. Steven came in first. His jacket over his arm. His tie undone and hanging around his neck.

"Hey, Brad, everything OK?"

Victoria appeared out of the darkness of the laundry room into the light of the kitchen. She was a stunning woman. Her half jacket was casually slung over her shoulder, her hair was slightly out of place and she was smiling ear to ear.

She reached over and shutoff the bright overhead lights and moved a dimmer switch for lights over the kitchen island bring them up to one third.

"That's sooo much better," she cooed. "Everything OK with Kate?"

"Absolutely. She was real easy. Went to bed on time, read some but when I check on her a little later she was zoned out." I wanted to keep talking only so it would be an excuse to keep looking at Victoria.

While I spoke, she tossed her jacket on a chair then steadied herself on the island and leaned over to pull off her high heels. What a view! The fine halter dress hung open and I could see right down at her gorgeous tits. While she fussed with the strap on her shoes, she looked up at me and grinned. I was busted. So embarrassed.

Steven made for a cabinet next to the dining room and was making a drink. Victoria winked at me and very quietly said, "Like what you see?"

I must have turned bright red. Steven returned with his drink; put an arm around his wife as he passed toward the kitchen refrigerator.

"Vickie, glass of white? And you Brad also?"

"That's a nice offer, but I should really get going."

"Nonsense. We let your folks know not to wait up, that we would probably have some late snacks and get to know you a bit, so, white wine OK?"

I nodded acceptance and couldn't help watching Victoria pull off the second shoe. From my position I could face Steven and see over his shoulder to watch Victoria saunter down the hall into the master bedroom. God what beautiful sight. Her legs. Her ass moved and the fabric moved just right. I was instantly jealous. "Holy shit," I thought. "Steven gets to fuck that every night, wow."

Embarrassment stuck again. I was so lost in the moment I didn't noticed that Steven had turned around and was standing right next to me, a glass of wine in one hard, his drink in another. He had actually nudged my arm to offer the wine and I didn't feel it.

"She

is

stunning, isn't she?" His head was tilted slightly admiring the view just as I was.

"Oh, geeze, I didn't,. I mean, I shouldn't, I'm..." stammering isn't a strong enough description.

"Hey Brad," Steven offered me the wine, "it's fine. You're a healthy young guy and she is a beautiful woman, you should look."

He offered his glass in a toast and we clinked them lightly. "Besides, you made my evening. I love it when men admire my wide. Come on, sit."

We crossed to a different living room. One with more casual couches and chairs with two giant sliding doors that looked out on the pool.

"In fact," Steven continued the thought. "I have great fun watching other guys wherever we go. Tonight for example. I needed to make nice with some business people and new contacts. Vicky was on her own. I could watch her surreptitiously across the room flirting and being chatted up by other men. It's a turn on," he took a gulp of his drink.

This was a new wrinkle in my sexual education. "Really, you're not jealous? Her flirting with other men?"

"God no. I encourage it. She's my secret weapon. She loves the attention, loves that it makes me hot for her. It disarms people I need to make deals with. She makes them happy, relaxed. When the timing is right, I can slide in and get their attention." Steven beamed. "She excuses herself and leaves me to work. But I can always see their eyes watch her walk away," he made a light laugh at that.

I took another sip of my wine trying to digest what Steven was saying.

"You look a little shocked. You have so much to learn about relationships and what makes some people, men or women, tick. What turns them on, what kind of fetish or kink their into."

"You mean like bondage or a foot fetish," I offered trying to sound worldly.

"So you have some frame of reference then. Yea, well, mine is watching other guys watch my wife and get a hard on for her. When we vacation I make sure she has short skirts, halter tops, silk blouses for evening and skimpy bathing suits," another gulp of his drink.

"When we get to the resort pool we set up at the opposite end from the diving board. That way she has the maximum exposure time walking to the far end, mounting the board, taking her time and executing her dive. She swam in college you know?"

"While she's walking I'm checking out the men. Young, old, doesn't matter. They turn their heads. Men with their wives are almost comical. They try so hard not to be obvious. Sometimes the wife catches him and might swat his arm with magazine. Poor bustards. And her move when she gets out of the pool? It's an art form. She grabs the hand rails of the ladder, pulls her up slow enough that men, and the women, can see the water sheet off her tanned skin. Her bikini top just low enough that at least the top of her nipples, or more, are showing. Then she stops at the top of the ladder and carefully adjusts the fit of the top and bottom and heads back to the diving board. God, what a show."

Steven got up to make another drink. It was difficult to ignore the tent in his suit pants. With his description he had given himself an erection. Without reason I got up and my perpetual semi-hard on was twitching. Steven met me half way. He had retrieved the wine bottle from the refrigerator and topped off my glass.

"We even play games with this. She'll get dressed like a high class call girl or a custom suited business woman and go to a bar in a real nice hotel. Either I'll pretend to be a stranger and pick her up. Or, the best?" Another gulp of the drink. "I'll take a seat with a view of her at the bar and see how many guys buy her drinks and try to pick her up. Turns me on so much."

"I'm really shocked. I don't think I could do that. I'd want a wife or girlfriend all to myself." This required a larger gulp of wine. Stephen leaned over and refilled the glass with a smirk. "It's not for every couple, but it spices things up."

"And she's OK with this? Sounds dangerous."

"It took a little time. Started slow with permission - encouragement to flirt. She started to like the attention even the danger I guess. Every time we had an encounter or an evening at a party or guys in a hotel asking her to dance, after each one we had the most amazing sex. She was horny as shit and I was so fucking turned on. It's like two animals. Hoofa."

I didn't know what to think, but as long as he was willing to talk, I started a question. "When she's at a bar and some guy gets real instant and you're watching, what..."

"Depends. We have signals. Our whole mutual fetish thing is approaching an art form. The best is when she wants to go farther. If she really enjoys the company of some guy there's a signal for that. When she gets home, she tells me all the details while we fuck our brains out!"

At that my last gulp of wine almost came out my nose. "Wait, she goes and sleeps with another guy?"

"Well, there's no sleeping but she gets what she needs, the guy gets his pipes cleaned and when she gets home, I get what I need."

"And just what is it you need dear?" Victoria arrived in the room from the hall like a soft breeze. As she passed in from of me I took in the shape of her fine ass barely covered by a tight, white and very small bikini bottom. It was barely two triangles of fabric tied on each hip. She plunked herself down on the couch net to Steven, kissed him on the cheek. "Anything I can help with?" Her voice was sexy and loaded with innuendo. Then she looked over at me and winked.

I wanted to make eye contact but she was wearing a very sheer cotton long sleeve shirt. Unbuttoned and no bra.

"Brad was interested in how we play games in a bar or at a party like tonight sometimes."

Victoria took a sip from Stevens drink, "Ough, Scotch. Be a dear and bring me a glass of white."

Stephen departed for the kitchen and Victoria leaned over, unashamedly leaving her small breasts totally exposed as her shirt flowed open.

In a low voice, "I fucking love it. I love the attention. I love the power I have over these guys Steven has to deal with. At a pool, he tell you about my pool moves? To feel all those eyes on me. Being mentally undressed. Knowing that tonight six guys, four of them married, will be jacking off thinking about fucking me? I'm getting wet thinking about it."

By this time Stephen has returned with her wine and heard most of what she said. "See what I mean. People have kinks, fetishes. Some people like to get tied up. Some people have a thing of feet or teasing their partner into submission. Are we shocking you?"

"And Stephen has other kinks too, but this one? Didn't take me long to warm up to it. Hey, let's go swimming!" Victoria turned, opened the sliding door and headed for the pool. Along the way she shed her shirt dropping it on a chair.

"Come on, I got plenty of swim wear." Stephen led me down the hall to the master suite. We could see Victoria in the pool. Stephen pulled off his shirt and undershirt quickly. Both of them were in their early thirties. She was fabulous and he was fit. Not chiseled or like a body builder but just a nice body and handsome good looks. To get a girl like Victoria I had a long way to go.

He reached into a drawer and tossed three suits on the bed. A very large bed. I had no idea they made beds that big. Now I was getting hard again thinking about what they do in this bed. Or, hell what he was thinking when his wife was out on a date fucking some other guy. I couldn't figure that one.

I looked over to see Stephen pull up a very tight pair of trunks. The kind like Olympic swimmers wear. He had a generous size cock that appeared to be semi excited. I picked up the suits he offered including a similar tight one but opted for very conventional, baggy boxer style trunks. I was beginning to think what came next was going to be awkward. It was almost midnight.

"You're a good looking guy Brad," Stephen said as he walked past me and out the bed room sliding door to the pool. "I think you will enjoy watching Vickie's breast stroke," he leered.

Not missing a beat I replied, "I think you will enjoy me watching."

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The lighting and the shadows in and around the pool were perfect. Romantic, erotic and adventurous at the same time. Victoria was doing a high quality back stroke the length of the pool with no top. With each arm extension, one breast then the other rose out of the water just for a moment. The sight of the water flowing over the perfect shape of her breasts was mesmerizing. Stephen and I settled in sitting on the edge of the pool by the shallow end watching as she made another lap and stopped in from of us.