Story Details

Babysitting and reaping the benefits

oddjob6235 on Virgin Stories

We moved down to central florida after my mom had remarried.It was really cool growing up down south and coming from indiana,i didnt miss the winters.Anyways after step dad got a promotion we moved to a much larger home and a bigger community.The first time i seen valeria,she was outside watering her yard in a tube top with cut off jeans,being 15 at the time i was having a hard time keeping my erection down.She ran over to us with those huge breasts just jumping up and down,and i looked over and seen stepdad staring as much as i was. They made small talk and told all about each other and she invited us to come over sometime to jump in the pool and have dinner wit her and her kids.

a few weeks passed and summer was just kicking in and i was looking for small odd jobs around the neighborhood so i could have money to go to beach and what not.Well i knocked on the valeria's door and she answered it with nothing but her bikini on and i got so close to those lovely breasts that i could see she was swimming and being cold and all those nipples where sticking out about 2 inches.Ive seen pictures in magazines on what a woman looked like,but never thought i would see it in person.I glanced down at her bottoms as i was asking her if she had any jobs around here i could do to make some cash.I could make out the lips poking through her bikini.I couldnt understand how a vagina could poke out that far,ive only seen one other vagina in real life and that was with my cousins playng doctor.

She said she had quite a few things i could do for her around the house since she was recently divorced and had her hands full with a little girl  and a baby. valeria told me to come in as she wanted to change real quick and asked if i was thirsty and to grab whatever i wanted out of the fridge. I walked into the kitchen and saw her daughter playing nintendo,so i said hi to her and the lil girl told me her name was heather and asked if i was her new neighbors and would i play with her in the pool.I laughed and said sure if your mommy lets me.Course valeria was standing right behind me and blurted out."he is more then welcome to come over anytime you want to baby" with that said and done she lead me outside and showed me some palm trees and shrubs that needed much trimming away from the pool. I told her no problem,i use to do this all the time in indiana. So i ran back home and grabbed my saw and wheelbarrow and told mom what i was doing. Mom followed me over to talk more to val,to assure her that i was a good worker and doesnt mind getting his hands dirty. I could of swore val had this evil look on her face when mom said that.

I'm about 2 hrs into cutting down this huge palm tree when val comes out and tells me the kids are asleep and would i like something to drink.With it being almost 100 degrees,i was soaked from head to toe and had my shirt off and getting really tan fast. Val and me made small talk and i learned alot from her in just a short amount of time.I didnt think much of the talk,but now that i look back she was seeing just how mature i was in my mind let alone the body.Val also made the comment about how well built i was for just my age,and kinda flushed on that comment.I mean here is this beautiful woman flirting with me and i was dumb struck. I went back to work and val laid out in the sun.I was trying so hard to focus on getting this job done,when i catch a glimpe of something.Val was laying on her stomach and i was just at the right position to look straight at her pussy and ass. I must of been staring for a few minutes,when she started to roll over to see why i got so quiet. I hurried back to work as if nothing was going on,and could feel her staring at my back boring a hole in it.I quickly gathered up the trimmings and yelled out to her that i was done.just at that moment she rolled over without her top done,and i got the full view of those huge breasts.I have never seen areolas that big before,and we both stopped in time and it took her forever to try to cover up. I wanted to keep up with her thinking i was mature and didnt say anything and pretended to blow it off. She gathered her top and quickly put it back on.With money in her hand she said she was thankful and sorry for the "peep show"that she was so use to running in the backyard half naked anyways and needed to keep in mind that she has new neighbors. I'm thinking Oh yea ive hit the lottery on this one big time.

Later that night i couldnt wait to get to bed and jerk off to the images that where burned in my head,imaging myself fucking that pussy and ass.afterwards i opened the window to get some of the florida air in my room when i noticed that my room window looked almost directly into her room and that she had the blinds all the way open.So i sat there for abit to see if i could catch a view of val and sure enogh in she comes with a full robe on.Oh yea,im gonna get a show tonight.She drops her robe and for the first time i see a naked woman in plain view.With the woods behind us i figured nobody sees me or her and this is a real good time to get really close to the view.I jump out of my window and quietly run over to the small bush line that runs between our houses.and get so close i swear she is gonna see me,but she doesnt.Val grabs some lotion and starts to rub it onto those huge tits of hers and all over her body.I see she is also somewhat shaven in the pubic region and she is running her hands up and down the front of herself and onto her pussy.She closes her eyes and she moves her hand back to her lips and starts jerking them up and down there,oh wow,shes masturbating.so to join the fun i pull my already hard cock out and join her in secretcy.She is really getting into it and i can hear her moaning louder and louder as her hands move faster and faster. I cum all over the bushes as she lets out this small whimper and her entire body shivers.I pull up my shorts and run back to my bedroom window. I cant believe i just witness the one thing boys my age will never see,i am truly blessed.

A week or so goes by and i still imagine val and that night hoping to get another view of her playing with herself but no such luck.One night We are all sitting eating dinner and val calls and wonders if i would babysit for her tonight as her other babysitter could not make it.I said sure,and she also asked my mom if i could go ahead and spend the night,just in case she does make it back to late.Val told her she was having a huge bridal party for one of her friends and it would be pobably an all nighter.Mom had no problem with it and with her next door,she could come over in case there was a problem with the baby.But mom knew i could handle it.ive done numerous babysitting jobs for the cousins as well as a few babies. 

So i packed a few books and some vhs movies and headed over.Val answered the door wearing these tight ass jeans that looked like they were spray painted on and i could make out every detail of those perky lips.Her top was a halter top that barely held her breast in and no bra which made the nipples stick out in the cool night air as she opened the door.Val gave me all the emergency numbers of where she would be and told me the baby is asleep and her daughter was getting ready for bed.So i had this huge house to myself.About two hours in i wondered into her room to see if i could make out anyone in the location that i jerked off to her,nope.You would have to put your face to the glass in order to see even the slightest out this window and was glad.Plan on doing more of that when it comes my way.I did alittle noseing and found her special drawer that had just about every dldo and lube you could think of.I grabbed one off the top and smelled it.Yep this is her favorite,i can still smell some of her juices on here,very aromic.uh oh that got me hard,need to head to the bathroom and jerk one off. After reliving myself i popped in a movie and slowly drited off to sleep. Around 4am i hear giggling at the front door and i jump up to see who it is,val is standing there drunk as a skunk trying to get her keys in the door and falls right on top of me.I get my first grope of those enormous tits,oh god were they soft. She was all over the house bumping into things and trying to get somewhere and going nowhere.Val asked for my help to the bedroom and i did. She went straight into the bathroom and i could hear her puking and gagging,i ran in to help out as much as i could but it was too late.She passed out their on the floor and puke ws everywhere,i could of left her but i couldnt.So i did the best i could with cleaning her up and trying to get her up off the floor without slipping.I scooped her up and was suprised on how light she was.I threw her on her bed and went back to cleaning up the mess hoping to make some brownie points with her.I hear her calling my name and i tell her shes alright and that i'll clean this up for her,not to worry.I think at this point she didnt care because the next thing out of her mouth was she needed help out of her clothes.So i jumped right up and nearly tripped over the clean bucket to cause more of a mess. I looked in and she had her top halfway up her head and her breast where in full view.I walked over to help her and kinda snickered at the view.Val laid back down and tried to get her pants off,but couldnt,so grabbed the hip area and proceeded to pull those tight jeans all the way down to her feet and realized she wasnt wearing panties and her pussy was right in my face.I could see and smell that odor i smelled on her dildo and sniffed it all in. I could see she was looking at me and asked me if i have ever been with a woman before.Still staring at what was in front of me,i said no ma'am.Val said well why dont you move closer to it and try a taste.I moved just as her last words left her mouth and had my lips wrapped around her entire pussy sucking in all her juices.I could feel her tense up as i slid my tongue inside her.She tells me to take my finger and work it into her pussy and i did.she was so wet and tight,i never imagined it would be like this,it was like eating a juicy apple and would not stop.her juices flowed down my finger an wrist.She tells me exactly where to go with my finger and my tongue and she grabs the back of my head forcing my mouth harder onto her clit.Val is bucking and screaming,im so afraid my parents are gonna think i'm killing this woman,but wouldnt step dad be so proud. As she is finishing off her orgasm i i look up at her and she tells me to get undressed.I do it as quickly and as fumbling idiot could do.Val asks me how i want to fuck her,i tell her to bend over,and she gets on all fours on the bed.Her ass is way up in the air and her pussy is flowing with my saliva on it.I move closer to her and position my dick at the opening and watch as it slids in oh so slowly.The warmth of her canal envelops my cock and i can feel her heartbeat though her walls.I slid my cock in all the way and she scream louder this time.I stop, thinking something is wrong and she tells me i am filling her up.Which i take as a good thing.I move my hips as the animal instincts and the numerous pornos have taught me.I dont want to cum to quickly and take my time and tease her with me pulling out of her and slamming it back in.This really gets her going and she is yelling at me to fuck her harder and harder.So i let it all go and pump as fast as i can and i can feel it building up inside me.I tell her im gonna cum and Val tells me to cum inside her pussy,i oblige and fill her cavity with my spunk all inside her coating her walls with all that i have.I must of cum for 5 minutes inside her and slowly pulled my cock out as she layed face down into the bed.I moved toward her,wanting to see if she was alright and she had passed out.So i got dressed,slid the cover over her an glancing one more time at that beautiful naked body and kissed her ever so lightly on the forehead whispering in her ear "Good night,val" I could see a small crack of a smile on her face as i walked out of the room.

The next morning,or actually afternoon,i woke up with a whole new look on life and it showed on my face as i entered the kitchen for something to drink.Mom and stepdad was in the kitchen smiling at me.dad said i looked like i was rode hard and put away wet.Mom looked at me and said she heard me come in real late and wondered how the kids did."they did great,no problems" about that time the phone rings, i answer it and its val.she sounds very giddy and wants me to come over so she can pay me for last night. I hang up the phone and tell the parents im running next door to get money.Dad makes a comment about yea i bet she wants to pay you,is that in cash or ass? I hear a slap as mom does to dads arm and he laughs.i blow it off and say yea right,whatever.But little do they now.

So i head over and knock on the door and val answers with the kids playing in the backyard,she looks somehwhat haggerd and throws me a smile.She invites me in and i walk right into the kitchen expecting a lecture on what happen last night.On the counter i see about 400 dollars,and figure shes paying bills.she brushes past me and tells me" theirs your money for last night" I was shocked,i said for what? Val turns and says "for taking such good care of me last night and for giving me the best time i have had in years"I must of turned 8 shades of red when she said that and she could tell i was embarressed by it and leaned in to give me a kiss right on the lips.She whispers in my ear"i want another crack at the huge cock of yours and i want to be sober when it happens. I was happy to oblige her and told her so,anytime day or night.

That is how i lost my virginity to an older and experienced woman.She showed me alot more things as the years passed on as well as my first threesome.Stick around for that story.

Until then

Oddjob

16 Comments

anna69aa

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bjcortland

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Just needs a little more editing. Spellcheck and other grammatical errors. It got a little hard to read after Val got home and it became one long paragraph. You need to break it up so it's easier to read. Keep writing, though. You certainly have talen

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