tagFirst TimeThe Baby-Sitter Diaries

The Baby-Sitter Diaries

byOregonDavid©

I started having a fetish for the 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 currently attends the college where I have taught for the last twenty two years, and I have literally known her her entire life. I watched her grow from infant to toddler to child to girl to young woman to mature young lady.

Her name is Rebecca.

When I 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 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. I met 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 baby-sat, 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 to all 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. At that moment, I was smitten with lust.

Smitten my ass, I wanted to fuck her brains out. 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, 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 your 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 lay 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 over 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. Too late." Rebecca teased her dad, but they booth knew that she would get the lawn mowed 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-pantied 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 mischieviously.

"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 on hole number eight was as far from the clubhouse as you could get and still be on the course. The cart path wound 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 hardon 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 couldn't cover my large 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 up, 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 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?" Such lusty words from this regal young lady was all the encouragement I would ever need. My tongue went wild, dipping, diving, flicking, exploring, tasting, delving. 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 sock off.

Her feet were hot and sweaty and I immediately went to work on cleaning them with my tongue, driving her crazy. 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. Her long hair was whipping back and forth behind her head. Finally she relaxed her grip enough to slide down and rest her upper torso on the golf seat.

"My God that's fantastic! Where did you ever learn to do that? I'll bet Patty really likes it when you do that." Mentioning my wife killed my buzz slightly.

"No, she really doesn't. She is not as free spirited as you. She likes it dark, missionary, and occasionally."

"Oh, poor David! She doesn't know what she's missing. I've never done any of this before, but I am sure that any woman would love it."

"Do you mean to tell me that you are a virgin?"

"Yes, are you shocked?"

"Hell yes! There aren't many eighteen year olds in this town that are still virgin."

"I know. I might be the only one."

"You've had so many boyfriends. How did you manage it?"

"Because the right man had never come along."

"Well I envy the man that finally gets to have you." She giggled.

"I don't think you need to worry about that." She struggled upright, using my head to get all the way up. "Stand up." Again I did what I was told. She dropped to her knees. She reached out, caressing both of my thighs with her small hands. She let her fingertips reach under the fabric of my shorts, feeling the curly hair around my groin.

"You are wearing too many clothes." She reached up and unbuttoned my shorts, dropping them to the ground. Since college I haven't worn boxers or briefs, content to be a freeballer. My erection sprang out at her, striking her in the cheek. She quickly turned her head and engulfed the first three inches in her mouth. Both of her hands grabbed the shaft, leaving an inch of my cock skin exposed. She pulled her mouth away. "Are all cocks this big?" I shook my head no. She just grinned, opened her mouth wide, and stuffed as much as she could into the opening. Soon she was sliding it in and out of her hungry mouth. What wouldn't fit, she was aggressively jacking. Sometimes it hurt, she was clearly inexperienced, but she was enthusiastic and that more than made up for it. Within minutes I could feel my heavy ballsack beginning to tighten.

"Be careful, I am about to cum." Her eyes showed only love and her mouth opened even farther as she tried to stuff the entire shaft down her throat. That was too much. I came into my baby-sitter's mouth and pulled her head even farther down onto my cock, bathing her throat with my copious semen. She coughed and sputtered, but I didn't let up, driving it further into her throat and pushing spurt after spurt of rope-like cum directly down into her stomach. I made one last thrust and I could feel her nose against my belly as the last vestiges of my orgasm faded. I could feel her gagging, I could sense her tears. I had gone too far, forced her into too much. I released her head so she could remove my cock from her throat. She pulled back only far enough to get a deep breath through her nose and then she dove forward again, putting my re-hardening cock deep into her throat again. I could feel her swallowing, her throat milking the last drops of cum from my balls. I was spent. I forcibly removed my cock from her mouth.

"Noooo! Let me suck it some more. That was awesome. I want to suck it again!" She begged me to face fuck her again.

"No, I have something else in mind." I pulled her up, reached down and removed her shirt, revealing a purple lace bra that barely covered her firm breasts. I massaged them both, feeling the hardness of the nipple underneath. I knelt and took them each in turn in my mouth before reaching between them to release the front clasp. I removed her bra and then her skirt and she stood before me, her last moments of innocence were mine to use as I saw fit. I scooped her up and laid her gently on the grass. I removed my own shirt and pressed my gray curly chest hairs against her tan and smooth breasts. I positioned my hips between hers, my cock was eager and knew exactly where to go. I stopped at the opening to her virginity.

"This is your last chance. From now on, you won't be a virgin. Do you want me to go on?" I summoned the last of my restraint, though I knew with a thrust I could take her and I was concerned I might anyway.

"Shut up and fuck me, you old tease!"

"OLD? OLD? I'll show you OLD!" And with that my cockhead ripped apart her maidenhead. I stopped when I saw the tears. Suddenly I was ashamed of myself.

"No, no, no! Don't stop. Please, please, please, I have waited so long for this day, for you to take me. Don't stop. I'll get used to it. Please David, please. You must fuck me." That was all the encouragement I needed. I thrust further, an inch at a time, pausing for her to adjust. When I was five inches in, I pulled out. I thrust in six inches and pulled out. I thrust in seven inches and pulled out. I thrust the entire length of my thick shaft into her tight virgin hole. Her head was rocked back, she was biting her lower lip so hard, I was afraid she'd draw blood. She was holding her breath. When I felt her hips relax I started my tempo, slow and easy. She started to move with me, then a little faster, urging me on.

"Fuck me David, fuck me. Fuck me David, fuck me. Fuck me David, fuck me." I did as I was bid. I knew I couldn't last long at this pace, her pussy was too tight, her body was too hard, her passion was too great for me to deny.

"I need to pull out, I am not wearing a condom," I warned her.

"I....am....on......the.... .pill.....don't.....stop....... fucKING.....MEEEEEEEE!" she cried between thrusts, ending in her third climax. I was right behind her, pouring my seed directly onto her cervix. I kept thrusting, my cock kept trying to empty into her, even after I had been drained of cum. Her orgasm continued, subsiding only when I couldn't thrust any more. We parted with a soft, wet plop.

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