The Babysitter Diary

I started having a fetish for our baby-sitter when she was young, much younger than her current age of twenty-three years. She has been the only baby-sitter of my three boys for the last eight years. Her mother is a colleague and her father is my best friend. She is currently a graduate student at the college where I have taught for the last twenty two years. I have literally known her for her entire life. I’ve watched her grow from infant to toddler to child to girl to young woman to mature young lady.

Her name is Rebecca.

When we first moved to this small west coast community, my wife and I were newly married and had just begun thinking about starting our own family. I began to play golf as an activity to replace the football I played in college and I was truly a novice. Though I was big and strong and could hit the ball a long way, I was never quite sure where it was headed. Chance allowed me to meet Rebecca’s father on the first tee one afternoon, and he could sense my newness to the game. Within a few minutes he was giving me helpful hints and we became fast friends. Even though he was a decade older than me, we hit it off pretty well. We shared a mutual interest in fine cigars, fine single malt scotch, and fine women. I found out quickly that his wife was an associate professor in my own department at the small university in town. She was quite a looker, even though she had two small children. Her hair was long and brown, straight and fine. She had magnificent carriage, erect and proper, which caused her smallish breasts to jut enticingly. She was quick to smile and after just half of a glass of wine, she would reveal her bawdy sense of humor. She and my own wife, who could have been her sister in looks and temperament, became fast friends and fellow shopaholics. We were the first baby-sitters for their two small kids. We would even take Justin and Rebecca home with us for the weekend, just to give our friends a reprieve and allow us to practice parenting. We became almost like family, brother and sister to Tom and Janet, aunt and uncle to Justin and Rebecca.

When our own boys started to arrive, half a decade later, Rebecca was six years old. By the time she was old enough to baby-sit, there were three boys, ages nine, seven and two. It was understood that Rebecca would baby-sit, it was as natural as rainwater.

The very first time Rebecca babysat, it was up to me to take her home. My wife and I had driven into the next town for dinner and a movie. The red wine in combination with the flickering screen had given her a headache, spoiling my amorous plans for the evening. I waited in the driveway for Rebecca to come out of our house for the ride home. I was shocked when I saw her silhouette in the headlights. She had blossomed.

We rode to her house in silence, though I did notice that she kept her hands on her thighs, fingers pointed inward, thumbs bent backward, somewhat awkwardly. I didn’t have a lustful thought about her, just a wistful thought about how young and beautiful she was becoming. Wondering and jealous, knowing that her next five or so years would be filled with discovery, joy, heartbreak, and if she was lucky, love and passion.

From that night on, Rebecca was our regular baby-sitter. The routine seldom varied, unless for some reason I needed to stay in and my wife taxied her home. Any knowledge of Rebecca’s budding romantic life came to us through her parents. We found out about her boyfriends through them. We found out when they became ex-boyfriends too. We still did a great many things together as an extended family. Rebecca was an avid golfer, much like her father. She even played in a few club tournaments with me when her father was unavailable. We spent a great deal of time in the same cart together. As many of her generation does, she wears clothing that mimics the pop stars attire. She can be athletic and sexy at the same time. Even in golf shorts and polo shirt, it’s hard not to notice her long, tan, athletic legs and her small yet well shaped breasts. She has her mother’s long hair and regal bearing. It was on the golf course, when Rebecca was eighteen that I first caught a glimpse of something I look back and realize changed the course of our relationship forever.

She was squatting down, trying to read a putt, her concentration was on the line it would take and I was standing behind her.

“I think it’s going to break a cup to the left,” she stated. I disagreed.

“It’s either dead on or half a cup to the right. This green runs that way.” I pointed down to the water on the right side of the green. To double check my read of the green, I walked around the cup to look at her putt from the other side. My eyes traveled from the cup to her ball and I noticed, for the first time, that Rebecca wasn’t wearing shorts that day. Instead she was wearing an athletic skirt. As she squatted down to read her putt, she was revealing that she was wearing purple panties too. Not only that, she was demonstrating that she had not yet learned about the wonders of tending the garden that grew between her legs or the miracle of the bikini wax. I was smitten with lust.

Smitten my ass, I wanted to fuck her brains out. But she was my best friends daughter, a girl I knew all her life, and I was looking at her like a hungry man looks at a well-cooked steak. She looked so tender, so juicy, and so damned edible. I was losing concentration. My cock stirred in my own shorts and I realized that I was beginning to stare. So did Rebecca. She just smiled and stood up slowly.

“I think you’re are right, David. It does break to the right.” She lined up her putt and stroked it smoothly to the back of the hole. When she bent down to pick it up out of the cup, I stood up quickly and adjusted my hard-on so that it would track to one side. I tried to keep my back to her until I could be sure it was waning. And I thought I had gotten away with it. For the rest of the day, the routine was the same. First I would look over her shoulder to read the putt then I would hurry around to the other side of the hole and get a good eyeful of her purple covered snatch and watch her make putt after putt. My own game suffered, I shot eight over my handicap. Rebecca shot six under hers and as a team that was good enough for first place in our flight. We won over thirty-three hundred dollars and as was customary, we bought the drinks at the 19th Hole. Rebecca was too young to drink, but that didn’t stop her. I realized quickly that she was like a lot of her peers, used to drinking beer. We sat in the golf cart, under the shade tree, accepting congratulations from the other golfers and the ribbing I deserved for letting a high school senior GIRL carry me to a victory during the day. At some point during the partying, Rebecca decided that it would be appropriate of her to sit across the front of my golf cart. She placed a couple towels on the bar frame and sat there, legs together straight across the dashboard of the cart. Once, reaching for her beer from the cup holder, her left knee flexed upward and when she regained her balance, she kept it there. That sweet, tender, purple covered pussy was now only a few feet from my face and in perfect view. She put her legs together whenever someone walked around the cart on the driver’s side, but she kept her knee up when only I could see what she was doing.

“Save my seat,” she commanded. “I have to go to the bathroom.” She hopped off of her perch and disappeared into the clubhouse. The passenger seat was taken by her father, who had just arrived.

“I see you two did well,” he said proudly, examining the scoreboards on the side of the outdoor patio behind the course’s club house.

“Yes, YOUR DAUGHTER did play well. I wasn’t much help.” I reached into my pocket and pulled out sixteen one hundred dollar bills. “This is her half of the prize money.” We both knew that if Rebecca accepted money from the tournament, it would jeopardize her amateur status. We also both knew how expensive it was to keep a tournament player in the proper equipment. Tom didn’t argue, he just accepted the money and slipped it into his pocket.

“DADDY!” Rebecca grabbed her father around the neck. “You should have been there. David would read the putts and I would knock them in. It was great. I was on fire!” Tom smiled broadly at his only daughter’s success. It made him proud. “I think he would make an excellent caddie!” Even I laughed at that joke at my expense. I really hadn’t been much more than a caddie that day anyway.

“Have you been drinking Rebecca?” Tom asked his daughter.

“Yes daddy. It’s a victory party.”

“You be careful.”

“I will, David won’t let me drink too much and get wild. Will you David?”

Get wild, I thought. Hell YES I would! “No, I wouldn’t think of it. In fact, it’s probably time you switched to water or iced tea anyway.” Rebecca pretended to pout, but she nodded. And then I saw a wink.

Tom stood up. “Don’t be too late celebrating. You have to mow the lawn tomorrow.”

“I know daddy, I know. I won’t sleep in. Not too late anyway.” Rebecca teased her dad, but they booth knew that she would get the grass cut as soon as she got up in the morning. She worked hard and her parents doted on her. Tom got up to leave, extending his hand and congratulations to me and giving his daughter a hug good-bye.

Rebecca took her seat back on the front of the golf cart and reached into the cooler for another Corona and lime. When she sat down, my eyes natural traveled to that purple cotton covered pussy that had filled my mind almost all day. I was shocked to realize that it was no longer clad in purple. Rebecca saw my shock and grinned mischievously.

“I was so hot, I needed to cool off. I feel a nice breeze already.” She opened her legs slightly to let me see into the pink flower that was her womanhood.

“So you noticed me looking, did you?” I asked.

“Noticed? Noticed what? That drool, that leer, that big salami in your shorts? I would have had to be Helen Keller not to notice.” I looked down at my erection straining at my golf shorts.

“Yeah I know. I need to pee too, and I can’t stand up.” I laughed at my own candor. Rebecca seemed to relish in my suffering.

“You know what, I think I left my putter cover on the bench at number 8. Can you run us out there so I can look?” I checked in the cooler, there were another five Coronas, just enough for the trip.

“Sure,” I answered. “It’s probably not safe for you to ride up there though, why don’t you sit down here?” I patted the passenger side of the bench seat.

“I think I’ll be fine here.”

“Suit yourself,” I warned her, and hit the foot pedal to make the electric cart go. Though she was rocked by the sudden movement, she didn’t lose her perch. Her legs did fly apart in her effort to maintain her balance, and I was there to get a good look. We careened across the golf course, which had been closed for the tournament. The green of hole number eight was as far from the clubhouse as you could get and still be on the course. The cart path carried us behind the giant berms that surrounded the back of the green. These berms were easily large enough to hide a caravan of golf carts. It was cool and shady where I stopped the cart in the same place as I had hours before when we played the hole.

“Is this where you dropped it?”

“Dropped what?”

“Your putter cover.”

“My putter cover? Look behind you silly, it’s on my putter.”

I turned my head and looked. The black leather and wool cover was securely wrapping the head of her White-Hot Two-Ball Putter. I looked back at her, somewhat perplexed.

“Stand up,” she directed. I did as she asked, adjusting my diminished hard-on as I rose. “Don’t you still have to pee?” I nodded before realizing how much I did have to pee. “Me too!” she admitted.

We both walked to the edge of the course and relieved ourselves. I was blatant about watching her pee. My God she was sexy.

“I didn’t bring anything to wipe with. Do you have any Kleenex?”

“No, but I am sure I can help you freshen that daisy. Would you like me to do that?” I asked as I finished watering the wild grasses at the edge of the course.

Instead of replying, she walked over and moved my hand off of my cock. She shook the last couple of drops off, but didn’t do anything about putting it away. It stirred in her hand, growing until her fingers no longer could circle it. I looked down. Both of her hands wouldn’t cover my swollen cock.

I picked her up and carried her to the front of the golf cart, seating her on the dashboard, facing forward. I pushed the entire cart off the cart path so I could kneel in the soft grass instead of on the hard sidewalk. I dropped my head between her thighs and placed her legs on my shoulders. I looked into her face, she was biting her lower lip. In those soulful brown eyes I could see both fear and lust, which I am certain was reflected in mine. I leaned forward, gently blowing on her slit. She shuddered in reply. I blow a little harder and moved in closer. I could smell her sex, her salt, her sweat. The combination made my head swim. I had been married more than twenty years and I was more than that many years older than she was. I was in decent shape then, able to stave off the middle age paunch that afflicted my generation, but my face had ruddy, crossed by lines, my hair had salt in the pepper. I stopped and looked up, checking for a sign that I had gone too far.

“Are you just going to blow me? Or are you going to eat me?” Those lusty words from this regal young lady were all the encouragement I would ever need. My tongue went wild, dipping, diving, flicking, exploring, tasting, dividing. I could feel Rebecca’s hips buck. She locked her ankles behind my head, thrusting it deeper into her wet pussy. She came quickly and often. Her golf spikes began to dig into my back. I pried her legs apart and pulled both her shoes and socks off.

Her feet were hot and sweaty and I immediately went to work on cleaning them with my tongue, driving her crazy. I had never put a woman’s feet near my mouth before, but this was an afternoon of firsts. I lapped between her toes, across the arch, around the heel, bathing her entire foot with my tongue. She climaxed again, just from having her toes sucked. She was hanging from the frame supports that held the roof up.