Author's Note:
This began as an idea from another author's story which my wife LOVED. She bought an erotic audio book, and said she masturbated while listening to it several times when I wasn't around.
Years before that book was commercially published in a more polished version, in 2006 the Literotica author, Selena_Kitt published her five-part series here starting with
"Babysitting the Baumgartners".
So, I highly recommend reading that series and supporting that author.
I appreciated that story's voyeuristic approach to a 19-year-old girl learning about sex during a vacation. So, some of the descriptive scenes in this story greatly parallel the babysitting one, but with a young male main character and a very different backstory.
*****
Prologue
It's funny how life sometimes takes a strange turn.
She was on her hands and knees when I grasped my stiff pecker and knelt behind her. I looked down at her ass and leaned back just a little to see her wet peach, her own fingers spreading herself open and waiting. Sliding the head up and down between the wet lips, I felt for the opening and pressed forward into her.
I closed my eyes relishing the new feeling of entering this warm, wet tunnel, her most private skin massaging the bare skin of my shaft. I took my time as I slowly slid easily in and out with the first few thrusts. It felt like nothing I'd ever experienced before. Her pussy felt so nice without a condom, this being a first for me, ... that is, the first time not using a condom. This cunt felt so good, I hoped to never have to use a condom again. And knowing her, I'd probably never need another one!
I thought about how much Jenny has learned about sex. She said she's looking forward to learning new tricks before we get married. But I'm confident she'll be a quick study.
... Focusing my attention on this new feeling of being bareback, with this pussy bucking back against me, her ass now pounding insistently against my hips, I opened my eyes. I grasped her hips holding her steady for a moment as he knelt in position in front of her, lifted her chin and thrust into her mouth, pushing her back onto me. I smiled at him as we spit roasted her together for the first time.
He was my best friend.
Intro
Dad was 18 years old when he graduated high school and he and mom married. He then enlisted in the Army as his first full-time job. When his Army unit deployed to a warzone, mom moved back home to live with her parents for about a year. After dad returned home to our small town at the end of his deployment, he and mom moved into an apartment, and I was born when they were about 22 years old.
When I was growing up, dad had a close friend, Doc Robinson, who was also our small town's only doctor. They met when dad was in the Army, and "Doc" was serving as a reservist in an Army hospital unit during his own deployment.
For as long as I can remember, Doctor Robinson and his first wife were always at our house for dinners, birthday parties, and holidays. His wife was "Aunt Carol" to me, even though we weren't related. As the only medical doctor in our small town, everyone knew him and referred to him as "Doctor Robinson." I learned later that Doc's wife couldn't have kids, so they grew up childless, which sort of explained why mom and dad were always inviting them to share our family times. They were a part of our family. And spending so much time at our house, I always knew him as "Doc."
I was about ten years old when Aunt Carol died in a car accident. Shortly after the funeral, mom encouraged me to start spending more time at Doc's house, hanging out with him in his garage and helping him when he was working on his old cars.
Restoring classic old cars was a hobby to Doc. He always had three of them in different stages of restoration. Some were waiting for parts which were hard to find. Others needed work on the drive train or engine, and he was always out there tinkering on them. So, when I was ten, I started by learning which tools to hand him, then eventually learning to rebuild engines, restoring a car body with Bondo or replacing a body part, and everything there was to know about cars.
It was three years after his wife died when Doc found another girlfriend, first meeting her at a medical conference, and they married a year later. Miss Richards was about ten years younger than Doc. And when she became Misses Robinson, I shortened it to "Miz R." She was a buxom blonde, with a narrow waist and tight butt, and she looked like a cheerleader.
Miz R was always nice to me, and she even said how much she appreciated that I kept her husband company in the garage. She would keep junk food in their house for me, even though Doc disapproved. She told me she felt better knowing I was out there with him when he was crawling under a car or hoisting an engine up and out to rebuild it. So, her stocking up on junk food which my parents wouldn't buy was her way of rewarding me. "He deserves to live a little, Doc, so get over it!" And she even spent some 'girl time' with my girlfriend, Jenny, when I started dating. If Doc needed my help in the garage and Jenny wanted to spend the day with me, Miz R would offer to take Jenny out to get their nails done and they'd go shopping together.
With the amount of time I spent helping Doc work on cars in the evenings and weekends, he became my best friend. He was almost like a second father to me, since my dad worked midnight shift in the factory and couldn't spend as much time with me. When I started dating, Doc was the one who first told me about "the facts of life." He even loaned me a car whenever I needed to use one for my dates with Jenny.
When I was ready for my Senior Prom and about to head out to pick up Jenny, I planned to use my mom's family van. Doc and Miz R came over to our house to see me off, and he just tossed me the keys to a car, saying "Just don't drive too fast." I picked up my date and dropped Jenny off at the door to my Senior Prom, opening the car door for her to get out of a perfectly restored '69 Corvette Stingray!
By the time I was 19 years old, I wasn't a virgin. My girlfriend, Jenny and I had a few experiences fumbling around in the back seat of a car or van in the dark. But she was deathly afraid of getting pregnant, so we only did it a few times, with her always worrying that a condom might break. With her reluctance to have sex, Doc suggested I might ask her for oral, but she wasn't having anything to do with that. So, my sexual experiences were limited to hand jobs and the rare condom-covered sex, ... when Jenny felt reckless enough.
Doc and I were so close that he even suggested I might go with them sometime when he and his wife traveled to their vacation home in Florida. My parents just wouldn't allow it while I was still in school. Every time I mentioned it to mom, I was told "You can't miss school for a week in the fall or winter, and we want you home for the holidays."
But in the fall after my high school graduation, Doc again invited me to go with them on a week-long vacation to the Florida Keys, staying with them at their beach house. He said it's not much of a party place, being somewhat isolated, but it does have a rather private beach. It would be a week of just relaxing to enjoy the warm weather.
Getting away from the northern mid-west cool autumn weather would allow me to work on my tan. And being out of school and almost 19-years old, I could make my own decisions, so I said 'Yes!' Miz R seemed a little surprised at first when I told her I was going. But she quickly warmed up to the idea and even gave me an odd smile which looked like she would really enjoy me coming along this year.
When Doc invited me this time to go with them, Jenny was still 18 years old, and finishing her last year in high school, so she couldn't go with us. But I decided it was my one final chance at a getaway before Jenny and I would go off to college together after she graduated. I packed my bags and was finally heading off to the land of sunshine and warmer weather!
Vacation
After arriving at the house rather late the first evening, Miz R ordered her favorite seafood dinner delivered from a nearby restaurant. We settled in with a nice dinner at the condo, then I explored the layout of the house.
It was a two-story house, with the usual kitchen separate from the living room and dining room combo area. Upstairs had three bedrooms, with two of them sharing the hall bath, and I unpacked to stay in one of those bedrooms. The master bedroom across from mine had its own private bathroom and a balcony overlooking the beach. The condo shared a relatively secluded beach with a few adjacent properties, which seemed unoccupied.
I wanted to spend most of my time here trying to soak up some sun. Back home, after September in the northern mid-west states, there are very few opportunities for the weather to allow me to lay outside in the sun. So, I wanted to return from this vacation with a deep brown tan which might last through the winter.
The first morning, I went downstairs to the kitchen where Miz R had breakfast ready. But for some reason, the smell of bacon just wasn't very appetizing. I felt my stomach getting queasy at the thought of food, so I politely declined to eat anything, saying my stomach wasn't feeling up to it. I just wanted to go outside to get an early start on my tan.