The Cougar's New Toy

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.

Within an hour, I was laying on my beach towel just off the deck of the house with no one else in sight. The traditional swim trunks I wore hid everything from my waist almost to my knees, so I tried pulling up the leg portion to expose more of that skin. I was laying on my stomach, reading a sci-fi novel sometime later when Misses Robinson came out. Hearing the sliding doors open, I looked up and just stared in amazement.

Miz R stepped out of the house wearing a black micro-bikini, with small triangles of material not even two inches wide barely covering her nipples and sex! None of the girls in our small town at the community swimming pool wore anything like that. And Jenny, as shy as she was, would only wear a one-piece bathing suit. I guessed that Doc might have chosen this place for their vacation getaways for the relative privacy, expecting that his new wife might dress like this.

Walking toward me across the forty feet of sand from the deck, Miz R stopped beside me. She dropped her large bag and took the large blanket from under her arm, spreading it out on the sand beside my towel. Then she kicked off her sandals as she stepped onto it. When she turned her back to me and bent at the waist to dig into her beach bag, that bikini thong left her bottom almost completely exposed. I couldn't resist looking at her ass for a moment, with that small triangle of material covering her puffy lips between her thighs and pulled tight enough to show the cleft between those lips. Then I tried not to stare by looking down and focusing on my book. She was Doc's wife, regardless of how exciting it looked, and she's old enough to be my mother!

"Are you feeling any better, Victor?" she asked when she straightened and turned toward me.

"My stomach's a little better," I replied, putting my book down since she seemed to want to talk.

Turning over onto my back, I could see her as she laid down to my right just a few feet away. She laid on the blanket on her left side facing me and I closed my eyes. Squinting in the bright sun, I could steal glances of her out of the corner of my eyes without staring.

"You know, Victor," Miz R began, turning to look at me, propping herself up on her left elbow and resting her head on her hand, "Doc has always wanted you to come along with us on these vacations."

"He's mentioned it to me every year," I said, "But mom wouldn't let me miss school."

"I look forward to this time away every year," Miz R casually pointed out. "This is my happy time away from being a proper doctor's wife in a small town."

I glanced quickly at her, seeing her smile, focusing on her face so as to not stare at the rest of her. Seeing her with that small bikini, I couldn't help but compare her to the other girls I knew back home. I knew Doc was close to fifty years old, and Miz R was closer to mom's age, around forty. But she didn't look like any mom I knew. She was stunning!

"This is like a graduation present," I said, continuing the conversation, "getting to work on my tan so late in the season." Sitting up, I tried distracting myself from the beauty beside me by picking up a bottle of tanning oil. Pouring some into the palm of my left hand, I set the bottle down and pulled the legs of the swim trunks up to start working it into my thighs and over my abs. I picked up the bottle of oil again, poured more into my right hand and dared turn toward her, asking "Would you like some?"

"Okay," she said, sitting up and taking the bottle from me. She squeezed some into her palm and rubbed it over her shoulders and arms.

I pulled my trunks waistband down a little, looking at the tan line still visible from the small speedo suit I used over the summer. In the privacy of our backyard at home, I preferred to get the most out of the summer sun by wearing a much smaller suit like the ones worn by competitive swimmers. I would have liked the waist and legs of these trunks to be even closer to my legacy tan. But I left that small speedo back home, not wanting to embarrass Doc or Miz R. Now seeing her and the way she was dressed, I wished I had brought it with me and I pulled and rolled the legs of the trunks up as much as I could.

"That looks a little silly," Misses Robinson said.

When I turned to look at her, she had already untied the top string from around the back of her neck to let the small bikini triangles dangle onto her stomach! She was wrapping her hands around those bare mounds, covering her full breasts with the shiny oil.

I couldn't help but stare at this gorgeous blonde's boobs as she worked them! I was mesmerized watching her hands lift and caress those mounds, making them gleam in the sunlight, with those brown nipples sticking out. I really appreciate my girlfriend, Jenny's boobs, which are just as big as Miz R's. Now to see Miz R's chest fully exposed, gleaming from the oil in the sunlight, ... and without those thin straps holding them up and without small patches covering her nipples, WOW!

"Just take them off," Miz R said, snapping me out of my trance.

"What?" I asked in surprise, looking up to her eyes when she turned to me.

She pointed with a casual wave of her hand at my bunched-up swimming trunks. "Those swimming trunks look silly that way. Just take them off so you won't have tan lines. I won't mind."

She reached her hands behind her to untie the bikini string across her back. Pulling her arms and shoulders back in that way thrust her bare chest out, as if teasing me. She dropped the bikini top to her right side and picked up the bottle of oil to start working some over her belly. Her abdomen was soft and a little rounded but still rather toned. Her right hand worked some oil down further to the remaining small triangle, slipping under that small patch of cloth. She worked her hands under the strings of her bikini bottom, and she continued rubbing her legs, hips, and into the creases at her thighs.

When all of her skin glistened with the oil in the bright sun, she looked over at me not moving and let out and exasperated sigh. "No one can see, Victor," she said dismissively, making me feel a little naïve and prudish. "It's just us out here on this beach. And I don't mind."

She hooked her thumbs under the string of her bikini bottom, leaned back to lift her hips as she slipped that last lonely triangle of modesty down her legs and off. Holding it out for me to see, she said "There. You won't be alone," and she dropped it beside her with the top. Laying on her back on the blanket, she looked over at me when she turned her head. "Well?" she asked, expecting me to follow her example.

"What about Doc?" I asked, glancing back at the house.

"He's watching the game on TV," and she shifted her legs. Spreading her feet and knees apart, opening her thighs, she turned her head to look at the sky and closed her eyes.

Staring at the naked body just a few feet away, I couldn't see any hair on the front of her mons, and I wondered how she was so bare. I expected some pubic hair on her fuller body. Hers was more mature than my girlfriend's, more rounded and softer. But Miz R would put most younger girls to shame with her figure.

"Don't be shy," she said, with her eyes closed. "I promise not to watch," and I was now feeling self-conscious. If she did see me, would she be impressed at my manhood or would she laugh at it?

Still hesitating, I looked around the beach. She was right, there was no one else within sight. I pulled the waistband of my trunks out a little again to look at my summer speedo tan lines further down.

Glancing over at her, Miz R's breasts were tilted to her sides as she lay on her back. Seeing those gorgeous globes, I was very nervous, knowing I wouldn't be able to suppress the evidence of my arousal. But I wanted a tan without half my legs remaining white. And with Miz R so casually stripping in front of me, ... I felt a little childish being reluctant.

Lying down, I inhaled sharply with a new determination as I arched my back raising my hips to slip the trunks off, trying to turn away from her so she wouldn't see my stiffening member. Turning my head to my left, I focused my attention on the sand off that side of my towel, calming and managing to at least slow the process until the shaft was just long but not standing at full attention.

Seeing the pale skin at my groin, I reach for the bottle of sunscreen and squeezed some into one hand, rubbing my hands together. Then I laid back and applied it to my member, taking care to cover all of the skin which was exposed to the sun for the first time. Paying such close attention to the details of protecting this sensitive area from sunburn briefly distracted me from Miz R's display.

It felt strange to be outside naked in full daylight, and I couldn't remember ever doing this outside.

The untanned skin at my hips was little more than a one-inch band of white on each side, stretching further down as it widened across my front, with my thick dark pubic hair amassed above and around my genitals. My member was still long and thick from the arousal but fortunately holding steady without rising further. And my nut sack hung heavily between my thighs, with the hot Florida sun making them droop further down trying to cool the contents.

Trying desperately to ignore the excitingly bare body beside me, I laid back and closed my eyes. The waves on the shore provided a distraction, with their rhythmic sound hitting the sand soon taking over and helping me relax a little. But when Miz R started quietly humming, it was as if she were calling to me, reminding me that she was there. Just the thought of those bare tits so close ... my member remained long and thick, but thankfully it wasn't standing straight up.

After about ten minutes lying in the same position, I reached to my groin and adjusted myself, lifting it to lay the fleshy shaft across my left hip. Then I treated myself to another glance at Miz R. The oil and sweat on her already tanned skin seemed to make those mounds glow, and I just wanted to turn over and stare into those gleaming headlights. But I adjusted my butt on the towel, rotating a little to lean to my left as my member twitched. After shifting my position, I brushed my feet together to try knocking some of the sand off of them.

Miz R turned her head to look at me as she raised a hand to block the sun from her eyes. "This blanket is longer than your beach towel. I'll move over so you can join me here and you can stop kicking sand around."