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The Ultimate Baby Sitting Job

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Famous Story
At sixteen, I was the only person in a secluded neighborhood that was old enough to babysit. My parents, being in the Jaycees allowed me access to a load of parent’s that were in need of an older kid to sit with them on Friday and Saturday nights, a little job I had begun at the age of thirteen.

Being a club that prides itself doing charity work, in the older days (the 70’s) it was an association that, for the most part, attracted a slightly higher income individual. Mostly these people had the time to give and also understood the need for charitable work in the community. They provided turkeys at Thanksgiving, toys at Christmas, and so on throughout the year.

Obviously predominately a men’s’ association, they were not chauvinistic and had a similar branch called the Jaycettes. This club was an extension of the men’s’ club and mostly were the wives of the gentlemen in the men’s club.

As my parents had belonged to this club for many years, I knew as an early adolescent most of the members as well as the wives. So you might say, as I got older, and went through puberty, I became a good source for mowing yards, helping with handy work when the husbands were away on business or JC events. And then, obviously, babysitting. Otherwise, there would be little need for this story.

At sixteen, I played a lot of sports within our small town. My parents had hopes that I may be good enough in one sport, or another to obtain assistance in the form of a scholarship to college, therefore; I was not required to have a job. I did however yearn for a little more money than my allowance provided. A weekly allowance back then, not a large sum today, was twenty dollars a week and a tank of gas.

To earn this, I only had to be a sweet, and lovable teen that I had become and do a few chores around the house. I took out the trash, mowed the yard, and was responsible for cleaning my bedroom, the latter being irrelevant to me as I did not allow anyone in my room at that age.

We were lucky enough to live in a small thirteen home community at the time, and probably even today, would be considered an influential community. The homes were quite large; the moms rarely worked if ever, they were “stay at home” moms. Coincidently two of the women, excluding my mother (step-mother), were also Jaycettes.

My step-mom was the oldest at time, at the ripe age of 30. My dad had remarried a much younger woman, by ten years, for his second wife. The other ladies were twenty-six and twenty-eight. Not much different, and not close to a motherly age with regards to my age. They were all hot, both blondes and one brunette, my mother. My mother was hot as hell, but at the time I did not feel right looking at her that way. But when she sat out by our pool in her bikini, it was very hard not to notice the five-ten frame with legs to the heavens and stacked with a rack that was incredible. But, enough about her.

The neighbors, both of which lived across the street from each other, both being blondes were very different in size and shape. Sherry was five-seven, maybe one-thirty, and a great set of 36D’s. Marcia, on the other hand, was five-foot at best, probably a hundred pounds and sported a dainty 32B at best. But, they were some perky babies that had the hardest nipple that would protrude all day long on a ninety-degree day.

All of the ladies’ in the neighborhood would share their pools on different days with the other moms to allow the kids to swim while they drank and played cards. One day here, one day there.

I rarely attended these “get-togethers,” I more preferred to spend time with my girlfriend, who lived down the street. Besides, with her mom at the pool with the other ladies and dad away on business or at the office, it left a lot of play time for a couple of teens.

**To the story**

As close as the houses were when I would babysit, the parents would arrive home generally late, offering to take me home. But I rejected the offers when possible and would walk home. This way I could make a late night stop by my girlfriends, and she would try to get out of the house and meet me from time to time weather permitting as her parents slept. We did not have cell phones, email, and texting back then. We roughed it, the old sneak and hope.

It was one winter night early in December where the story became a memory.

I was sitting with Marcia’s twin seven-year-old girls, and also Sherry’s three girls, age four, five and seven. All of the kids knew me and loved playing “dress up Chris”, don’t judge, you do what you have to make money, normally I was the queen because I was older.

Marcia and Sherry were going out with the other ladies and for whatever reason, my mom had decided not to attend. Marcia had told her my mom that it would be late and suggested to her, “why not let Chris sleep over if he likes, and I will drive him home in the morning.”

My mother obviously did not have a problem with that suggestion as she told me as I was leaving the house, “If Marcia gets home too late, just sleep over and come home in the morning. The weather looks like it could be nasty tonight.”

I said, “Ok, but I can walk home if she is unable to drive, it was no big deal. I’ve done it so many times before.”

She replied, “That’s fine. You decide what you want to do, but I think she made a nice gesture.”

Now, as a young man, or at least I thought of myself as one at sixteen, I had fantasized about both Marcia and Sherry. I had even spent the night at Sherry’s house once, about a year earlier. She came home late, her three girls were asleep, and she just asked me, “Chris do you mind staying tonight, I don’t think your parents will mind, I just don’t want to be alone.”

Sherry and her husband Mike had been going through a difficult time as he had taken a traveling job and was away three weeks at a time every other month. The job must have paid well; Sherry had a new car, and they had just put in the pool that summer. So, things were good but she was lonely.

I said, “Ok, I guess that would be ok, but I did not have anything to sleep in.” I had already begun sleeping in the nude at home by then, but there was no way I was doing this at someone else’s house.

Sherry said, “No problem, undress to your underwear, and I will do the same, that way you will not feel so weird. I am sure you have seen your mom in underwear, and it is no different than seeing me in a bathing suit.” So, Sherry just began taking off her dress, then her pantyhose, and stood there in her bra and panties. Then she said, “See, no big deal, now get undressed and climb in here where it is warm.”

WOW, was my only thought. I had been with naked girls plenty of times, but not close to a half-naked woman. And though the bra and panties were like a bathing suit, I had not been in a bed with a woman wearing that. It was odd, and I asked her to turn the light out, to hide my embarrassment as I jumped in the bed.

Sherry rolled over to hug me and thank me, and all I could do was try to stay away from her and hide the “adult” sized hard-on she had caused. I think she sensed it, and we just rolled over and went to sleep. You can imagine the hard on did not totally go away all night, so as soon as I awoke, I went straight in the bathroom a jerked the pony till I shot on the wall.

Back to the topic at hand, sorry.

The evening passed uneventfully; it had begun to rain, and the wind was whipping something fierce. I put the girls down at eight read, them a book, and they went to la-la land.

I don’t like to say I was a snoop at that age, but I did have a fetish. Lingerie. I loved women’s panties; the Sears catalog became my friend at a young age. I would fantasize about taking the panties off of the models just to sniff the crotch.

I had always loved that V in a woman’s stature. I loved looking at a great ass, and loved women’s breasts, but I loved all of the aromas a woman, or I should say, a girl has. I had lost my virginity at a young age, and I suppose I had many dates because girls obviously talk. I was one of the few guys my age that licked pussy; I do not know if I was good, but sixteen year old girls did not have a clue either. However; it must have felt good.

**Sorry, brain fart.**

Marcia and Sherry arrived back around one-thirty that am morning. As they came in the back-door from the garage, obviously a bit high, they were a little loud. I met them there in the kitchen and “shushed them.” They laughed, and Marcia said, “We are going to have one more drink before bed-time, why don’t you join us.”

I had not had many alcoholic beverages at my age, but I said, “Why not. What are we having?”

They both spoke up at the same time and said. “Vodka-Tonic.!”

Marcia said, “Chris, grab a lime from the fridge, and show us some expert bartending skills.”

I was not sure which was vodka or scotch except by the label, I did my best to figure it out as I pretended to know what I was doing.

They must have enjoyed them, I thought the drink was nasty, and it burned. Marcia looked at me in a few minutes as they were talking and said, “Drink up Chris, and then fix us one more.”

I did as instructed, and the ladies’ went through them fast. Sherry looked at Marcia and said, “Can I just leave the girls here for the night and come by in the morning to get them?”

Marcia said, “Of course, but, it is raining outside, Chris can grab an umbrella and walk you across the street if you want, right Chris?”

I just nodded, and Sherry said, “Thank you.”

I walked Sherry home, just across the street, snuggled tight against me arm in arm as the wind whipped, and the rain came down hard. We go to the door, and she turned and looked at me, then she asked, “No kiss goodnight?”

I kissed her on the cheek, and as I drew back, she grabbed my face and shoved her tongue down my throat. WOW, what a kiss, a woman kiss, an adult kiss, this was no thank you for sitting my kids kiss, this was deep and hard. Not to mention, my cock was too.

As I drew back from the kiss, Sherry simply looked at me and said, “Goodnight sweet boy, have fun tonight.”

She opened the door, stepped inside, and closed it behind her. Leaving me to wonder what the fuck she had meant by that.

I walked back across the street; the rain now had blown my clothes wet from the hips down, and I walked into the house and Marcia was standing there in the kitchen, looking quite hot, asked me, “Chris, did you go into my bedroom tonight?”

I stammered a bit, just looking at her, trying to come up with what I should say.

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She simply looked at me again and asked, “One more time, I am not going to be mad, but did you go into my bedroom and do anything tonight?”

All I could do was be honest, she was either going to make me walk home or worse, tell my parents. She knew what I had done; I was sure of it. So I could not lie about it.

I said, “Yes ma’am, I am sorry.”

She said, “And explain to me what you were doing please and follow me.” I followed, and we entered her bedroom. She said, “Show me what you were doing in my drawers, as there does not seem to be anything missing, but they are not as I left them when I went out tonight.”

I said, “I know, I did not get to put things back in correctly before you were coming in the back door. When you came in the house, I was running to the kitchen from your bedroom, hoping to get a chance to fix the drawers while Sherry was waking her kids.” Again I said, “I am sorry.”

Marcia said, “Quit with the apologies, and tell me what you were doing.”

I reached into a drawer, and pulled out a couple of pairs of her lacy panties, and I just began sniffing the crotch. Rubbing them all around my face, and putting them in my mouth.

Marcia just stared at me, and I am sure she could see the fear in my eyes as I dropped my head down. She looked at me hard, then asked me, “Which is your favorite?”

I held up a black pair that, other than having a crotch cover, would have hidden little if anything from view. She took them from my hands and said, “Sit” and pointed to the bed and walked off into her closet; I began to sweat, I was not sure what the fuck was happening, but I knew it could not be good. But all I could think to myself was, “please, please, do not call my parents.”

In about two minutes, Marcia walked out of the closet, my head was down looking at the carpet, and she said, “Look up here kid.”

I looked up, and she was standing there in the panties I had picked out as well a black lace bra and high heels. She said, “Is this what you wanted to see?” I simply nodded and mouthed the word yes as I was too stunned to speak.

“So, now what are you going to do with me?” she asked, walking over to me, putting her hands on my face softly and looking down into my eyes. I couldn’t speak, and she just bent forward and laid a soft kiss on my lips. No tongue, just a soft lingering kiss. Then she said, “Chris, you better be good tonight, I have never fooled around on Mike (yes same name as Sherry’s husband), but you have made a lot of the ladies, including me have thoughts for a while as you have grown up. So lets’ make this good for both of us.”

Then she kissed me again, and slipped her tongue into my mouth ever so softly, at the same time she took my hand and brought it to her small firm breasts, and moaned.

I began tweaking the hard nipple in my hand with two fingers and slowly slid a hand up her inner thigh. As she began kissing me harder, and her breathing began to quicken, I touched the warmest and wettest spot between a females legs I had ever experienced. I just had to slide my finger inside the leg hole just to get a feel of the dampness and those pubes that were visible through the lace. God she was wet.

Marcia took a step back and let out a sigh. As she did that she began to take her bra off, and then slid her panties down, never taking her eyes off of mine. When she stood straight up, in only some high heels, I saw for the first time a WOMAN, and damn what a woman. Her soft blonde pubes were unlike those I had seen in Playboy; she had trimmed them into a nice straight path, and her vulva was a beautiful soft mound, her inner labia almost unseen. It was simply the most beautiful pussy I had ever seen. My mouth was watering.

I jumped up and began yanking my shirt off, and Marcia said, “Whoa cowboy, this is going to be a long rodeo, take it easy I want to unwrap my candy slowly,” She came over and kissed me, and as I began to touch her again, she said, “Slow and soft, ok? We don’t have to catch a train.”

I did exactly that, slow and soft touches, almost like air, except I could feel everything about her and all of the heat from all of the parts. We kissed, and touched as she undressed me, then she dropped down and took my pants and briefs down in one motion. There were no words, no warning, she simply stuffed as much of my cock in her mouth as possible in one swallow.

Now, I never have claimed to be huge, but seeing this woman take almost all of my teenage seven down her throat had me over the top, and I yelled, “Marcia, I am sorry, I am going to cum if you do not stop.”

She slid her other hand under my balls and gave them a squeeze. That was it; I blew a cannon shot off. If my cum had been a bullet, half her head might have been lost. And I just kept cumming as she did not want to stop until she had drank it all.

Marcia stood up and said, “Mmmmm, now it is your turn.”

I wasted no time in laying her back on the bed, and slowly, softly, as she had instructed, working my lips and tongue to that one place every man thinks is heaven. The closer I came, the more I could see the soft pink color of her pussy and the juices oozing slowly. The aroma was incredible, and I almost shot straight up and took her whole cunt in my mouth. But no, I worked slow, to slowly I suppose as she grabbed my ears and said, “Fuck, lick my pussy now, and suck on my clit. You know what that is, right?”

Well, I did not need to be told twice. I went straight in, and I am sure within a minute she was sure I knew what a clit was. I clamped my lips around that little button, and just sucked it in. Twirling my tongue around it, making it wet with my saliva, I wanted this bitch to come all over my face. I could not get enough of her sweet nectar.

Her orgasm could have rocked a boat out of water, as wave after intense wave hit her. Maybe I had never brought a girl to orgasm, or maybe women had bigger orgasms, but I was not sure if she would pass out or not.

She pushed my head away after finally beginning to subside a bit from her orgasm, her breathing shallow and hard; she looked at me and said. “Boy, if you fuck half as good as you eat pussy, I may never let you go home. Give me a minute to recover, Jesus. I have not had an orgasm like that with a man ever, not even my husband.”

We lay there for a short time, cuddling and kissing when she felt my cock and realized it was as stiff as it had been when we had started. She just stroked me and said, “You are not quite as big as Mike, but that is a good thing, because we have so many places I think this will fit!”

I was not sure what she meant and looked at her oddly, when she realized I was curious to what she meant, and she said, “You are going to fuck every hole I have. I hope you love my ass, I want you to lick it like you did my pussy. Now, shove that cock in my pussy and lets’ have some fun!”

I got on my knees, opened her legs wide and slipped my cock into that beautiful tight pussy. As Marcia began to moan, I was afraid once again I was going to cum all too soon. But I slowed the pace, taking strokes that pulled almost out, then slammed hard back in. This seemed to work great as my mushroomed head was obviously touching a place that sent her screaming.

Marcia just opened her eyes and said, “Keep doing what you are, but don’t you dare move from that fucking position. You are hitting my G-spot head on, oh god, just keep doing it.”

Just then I experienced an orgasm from Marcia that at first scared me, then intrigued me. She came so hard that she squirted out around my cock, and the pressure forced my cock out of her hot canal. She was screaming and moaning, and as I put it back into her cunt, it felt like an oven the heat was so intense. I smashed through her orgasm, pounding away as hard and fast as I could. Marcia just looked at me and asked, “Are you about to cum; I want to feel you fill my cunt up with your cum!”

It did not take long. Marcia’s eyes looked like an animal in heat as another orgasm rocked her body. I shoved as hard and deep as I could into that tight pussy and think I hit the back of her cervix. As I did, I once again unloaded another, what seemed like, pint of man jizz.

At this point, nothing in the world mattered to me except to get another hard on, and soon.

As we lay there, totally exhausted again trying to calm our heart rates and breathing, she looked at me and said, “I do not know if I have another orgasm left in me.”

I looked at her and responded, “What about that sweet ass?”

Marcia smiled and let out a little chuckle and said, “Boy, aren’t you greedy. Do you think you can get it back up?”

Looking at her, I just said, “I am sixteen, what do you think. Besides, to fuck that great ass, I would tape a popsicle stick to my dick to get it up if I had to.” She just laughed, rolled over and kissed me sweetly.

Slowly she kissed down my hairless young athletic body, past my six pack of abs, and took hold of my cock and licked the head. I looked down at her, and damn she was hot. I said, “Spin that ass around here, I want to taste it.”

She spun into a sixty-nine, lowered her ass down to my face and I began to lick from her clit to that perfect rosebud. This must have been having a great affect as her blowjob was becoming more intense. As I spread those small firm ass cheeks apart and stuck my tongue into that asshole for the first time I felt my cock hit the back of her throat and heard her gag.

She fought right past it though and soon I was feeling her tonsils dancing around my cockhead. I never realized though how sweet an ass could tastes. I couldn’t get enough, but knew if I did not pull away from that incredible mouth, I would never be able to fuck that gorgeous ass.

I pushed her off of me and said, “Get on your knees.”

She did and I just spread those cheeks again and began to sink my cock into that ass. WOW, I did not realize something could be that tight and feel so good at the same time. She looked back over her shoulder, eyes rolling in her head, and said, “Oh baby, yes, fuck my ass good. Cum one more time for me deep in my tight ass.” And, although too soon for me, as I wanted this to last, I let go of one last load. Not much to it, but it felt good, and hurt at the same time.

We just rolled over, laid back breathing hard. Marcia turned on her side and said, “You are definitely going to be babysitting more. And I have a feeling you will be getting a lot more babysitting jobs in the neighborhood as well.”

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Written by NIGHTOWL6261A
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