Winston's Take Me Clubbing
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This is a work of fiction.
Any resemblance to actual locations or persons living or dead is purely coincidental.
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A continuation of
Babysitting for the Winston's
. In this installment our character returns to help them out again. Just not for babysitting. Being six months older and a college student, he has built on previous experience, expanded his sexual horizons and is ready for what our couple has to offer.
Not to give away details, but if bi-sexual or gay sex is troubling
you may want to move on. Or excessive drinking. And if the disco scene is a turn off?
Well, fair warning.
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Recap
As I explained in the first story, 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. Previously I was cooped reluctantly to watch the Winston's then 11 year old daughter. Only when the Winstons arrived home, I found myself in a wet dream come true. Seems the Winstons were swingers. It was the mid- 70s and key parties were a thing in certain circles. Playboy, Ms. and Cosmopolitan magazines, among others, were promoting a new sexual awareness. The zipless fuck was a topic of conversation among like minded adults. "Looking For Mr. Goodbar" was about to be published. Many Hippies were exploring the notion of free love and what evolved into friends with benefits. In the first story I spotted their name on a sign by the front door with three pineapples hanging under it. The middle one was upside down. Took me a while to catch on to that one.
After high school and before going to college in September, my folks and I had a deal. I could travel through Europe on a EurRail Pass for as long as my money lasted. My money. They would buy the plane ticket, but expenses were on me. To raise the necessary cash I washed cars, painted houses, sealed driveways and cut grass. The babysitting gig with the Winston's was supposed to be a onetime thing. When I opened my pay envelope at home, it was VERY generous.
The Europe trip was great and yielded several encounters that added to my sexual education and may be the subject of future stories.
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Another Encounter
Christmas break 1975 arrived
in the third week of December. I would be off for a bit over two weeks. My girlfriend, Diane, and I were still a thing, but going to schools three states away had cooled things. She started dating. I visited her twice in the first semester, but things were beginning to fade between us. We spent New Year's at a party, fucked our brains out, but it wasn't the same. College has a way of ruining long distance romances.
My folks were thrilled to have their only son home for the holidays and I took the opportunity to party with the old "Hush Hush Club" guys a few times. We drank, smoked, fornicated freely and swapped sexual exploit stories. Some of which were true. I hope a couple of the guys write for Literotica.
One Friday I was getting ready to hit it with the guys. There was a club not far away with killer music. Truthfully, I really couldn't appreciate the music or the dance style. But the disco era was in full swing and it was the place to be and to see women in slinky, braless disco dresses and guys with silk shirts open to show hairy ripped chests and tight pants that showed off fine glutes. I could appreciate both. I could from an early age. So to fit in, I had to learn some moves.
My Mother appeared at my bedroom door. "You look very nice; you didn't say you were going out tonight."
The month in Europe on my own and being at college for a semester had quickly developed a sense of independence. It didn't occur to me that I need to share my daily plans with my parents.
"Sweetheart, we really need a favor from you," my mother implored. Here we go again. This is how the first story opened.
"The Winston's can't get a babysitter for tonight and they asked us if you could cover Kate for them. Would you be a dear and babysit for their daughter?"
"Babysit? Mom, isn't Kate like 12 or 13. She can't take care of herself for three or four hours?"
"The Winstons have done a good job with Kate, but they said they would be quite late. Actually they didn't want to use their regular sitter. She's only 15 and they would prefer not to have her stay till one or two in the morning."
Two things went through my head, and my pants. First was a fond and vivid memory of the first time I covered for them. Seconded, they paid very well and I always needed cash.
I made a quick call to one of the guys explaining I couldn't join them tonight. Since I had regaled them with a detailed description of my first time with them, he understood completely and wished me luck. It was more like; "You lucky fucking dog. When you goanna share your good fortune with us?"
Obviously I agreed. I took a look in the mirror and decided the nylon, fake silk, blousy burgundy disco party shirt wouldn't work and changed into a long sleeve gray Henley. The black trousers were nothing special so they stayed.
My third hand Toyota got me across town to the rich section where the Winston's had an amazing home. A sunken formal living room. Another casual living room in the back with a view of the pool. The master bed room suite with a sliding door that also opened to the pool. The pool played a critical role in our first encounter.
Under the name sign on the porch there were still three pineapples. One in the middle was upside down. Wait. Wasn't it the other way before? That one was a head scratcher for several years.
I didn't even hit the door bell when Stephen opened the door and greeted me with a big hug like a long lost friend.
"Let me look at you Brad! You look
great
. College and what, six months has done wonders for you. Come on in."