My Summer Job
Copyright© 2015 by Jack Spratt
Erotica Sex Story: Chapter 1 - Andy is chomping at the bit as spring arrives. The new golfing season is close and the thoughts of his many interesting experiences from last season has him excited and wanting more as he looks forward to caddying. He also will be continuing his lawn care for the summer. He meets one of his teachers, and three of her friends on the course, and ends up caddying for one of them Aliyah. Close friendships develop. Andy's relationship with his sister continues.
If stories involving adults and adolescences make you uncomfortable, delete this story NOW. There are numerous very good authors on S.O.L. that will satisfy your literary desires.
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This story is a work of fiction. Names, characters, places, and incidents either are products of the author's imagination or are used fictitiously. Any resemblance to actual events, locales or persons, living or dead, is entirely coincidental.
Special thanks to Phil Gorman 2015 for his expertise in editing and proofing.
With the school year nearly over, I will be joining the hundreds of other students in Abbotsville attempting to land a summer job. Over the last few years, there have been way too many seekers with too few opportunities. My wants far outweigh my ability to pay for them. My family is not affluent, as some. Mom and dad work hard providing my sister and me with a good home. In the past, my lawn mowing and odd jobs kept me satisfied but this year I am hoping to get something more tangible and better paying; it is difficult when you are only fifteen.
My name is Andy Davis. At five foot eleven, and one hundred and forty-six pounds, I stand out in my class. Dad is a big man and it seems I am his mirror image. As soon as the snow leaves the ground, a visit to all my prior customers for lawn and odd jobs has me in position to make some money during the summer. My first job is in April, cleaning flowerbeds for Mr. Cross. He and his wife pride themselves on how well their home and yard look and are always in competition for the most appealing home. It is Mr. Cross who gave me a lead on a job that would give me a chance to earn good money being a caddy.
"Tell you what, Andy; I will put in a good word for you with the golf pro. He is in charge of caddies. There will be a tournament nearly every weekend during the season. I have no doubt, if you prove yourself, that you can earn a tidy sum during the summer. During the week you can still do your lawn work and then caddy on the weekends."
"Thank you, Mr. Cross! If I get the job, I promise not to let you down!"
"You're a good worker, Andy. I know you will do the best you can at everything you attempt. I will give you a call when I line up the interview for you."
Over the next three weeks, every time I return home from school, my question to mom is the same: Is there is a call from Mr. Cross? And every time the answer is the same: No. Of course, my thoughts are that he couldn't get me an interview or he just plain forgot. At this point in time, my lawn jobs keep me busy after school; most of my old customers give me the opportunity to do work for them this season. Actually, I only lost one because they are moving, but I picked up two new jobs.
Each evening after my shower, it is time to finish my homework. We have a small room off the living room that we call a study. This is where my sister, Jayden, and I do our homework. Jayden is fourteen and a real pain in the ass. As much of an agitation that she is, and this is something I would never admit to her, she is very cute! Several of my friends have made what you might call disparaging remarks about what they would like to do to her. Since discovering the joys of masturbating and understanding a bit of what boys and girls do, Jayden has been my inspiration for many of my daydreams when jacking off. Even for a sister, she is a very attractive girl. Mom insists both of us keep clean: we are groomed to look presentable at all times.
Jayden has beautiful long blonde hair that she keeps shiny by brushing it all of the time. Her big blue eyes are always shining mischievously. Jayden, like mom, has very full lips. Sometimes she uses mom's lipstick and eye makeup: it makes her look older and really sexy. She doesn't have big titties, but her nipples always seem to be hard and usually very noticeable, judging by the points in her t-shirts. A couple of times, when going to the bathroom, just as she is getting out of the tub I got a wonderful view, even though she quickly attempts to cover up. She has tiny nipples and all I get to see is the top of her pussy. It is puffy and looks something like a peach. Memories of it keep me producing lots of cum. Masturbating has become a daily ritual for me.
Arriving home one evening, mom hands me a note from Mr. Cross that says to call him tonight.
"Mr. Cross, it is Andy. You called."
"Yes, I did. I bet you thought I forgot about you. The golf pro has been tied up arranging times for a number of tournaments for the season, but I have arranged for him to talk to you this Saturday morning at eight. Can you make it?"
"Certainly! Where do I find him?"
"In the Pro Shop, just beside the club house. Have you been to Greenway Golf Club before?"
"It isn't hard to find. When you go through the main gate, just follow the main road to the club house; look to your right and you will see the Pro Shop."
"Thank you, Mr. Cross, I will be there."
At supper, mom and dad ask questions that I can't answer about caddying. Later, after completing my homework, I slowly climb the stairs to the bathroom. My mind is on Saturday morning when a slight noise gets my attention. Jayden is just finishing her bath. The hall is dark and I can't help but notice the bathroom door is slightly ajar. To me, it is an invitation to have a peek. Jayden is standing, facing the mirror, slowly drying her upper body. Her silhouette gives me a view of her chest from the side. Jayden is starting to show signs of getting breasts, a nice surprise for me. Her nipples are small, but they do stick out from her body. She seems to take her time softly rubbing each one as she continues to dry off. What has me really gaping is the time she takes drying her pussy. She brings the towel between her legs and slowly pulls it back and forth over her pussy slit. Her eyes are closed and she is humming softly. Finished, she drops the towel and her hand covers her love lips. She is fingering herself. My sister is masturbating! Boing! My cock is pushing against my pants as I am watching her. Quickly releasing it from its confines has me pumping it. When Jayden starts pushing her hips forward, against her finger, it really has me excited! Finally, she grabs the counter and gasps softly just as my cock is spouting out its hot cum in my hand. Quickly heading for my bedroom, I clean my mess with wads of tissue. Finally, the door to Jayden's bedroom closes. The bathroom is mine.
Locking the door, and then undressing, I locate Jayden's towel and sniff it, hoping to smell what a girl's pussy smells like. It just smells clean. However, there is a gold mine in the clothes hamper. Jayden's cotton panties are on top, the ones with the picture of Winnie the Poo all over them. They feel so soft. The crotch seems stained with her pee marks with a bit of crusty white stuff on the inside. Rubbing it, I bring my fingers to my nose. It smells like pee mixed with something else. Wow! My cock just seems to rise up, sticking out from my body. It has never got that hard so fast after jacking off before! Putting her panties to my nose, as I pump, really has me enjoying the feeling and the smell. Cum shoots into the toilet bowl giving me a good feeling again. Carefully putting Jayden's panties back, I shower. I remind myself to try smelling them again tomorrow night to see if it has the same effect on my five inches.
My sexual experience with girls, up to this point in my life, has been nil. I haven't been out on a real date or kissed any girls yet. All of us guys talk like we are real studs but it is just that: all talk. There isn't one of us that have had anything to do with a girl in regards to sex; mind you, every one of us certainly would like for it to be otherwise. Some of the girls in my class are very sexy looking with their tight clothes and makeup. I want to ask one of them out for a date, but I keep losing my nerve.
Finally, it is Saturday morning and I am up at six thirty; at this time on Saturday morning, no one else is moving. Prior to showering, my morning woody requires attention. It feels good to cum with the help of my sister's panties at my nose. This has become a nightly and morning ritual. Had I known the effect my sister's soiled panties would have on my cock, it is something that definitely would have been part of my life much earlier! After showering, I dress in an open shirt and dress slacks, hoping to make a good impression on the Golf Pro. It will take about fifteen minutes to get to the course by bike. Fortunately, the traffic is light at this time in the morning, which is good as this is my first visit to the course. There are many very expensive cars in the parking lot with people pulling golf carts and moving about. There must be a tournament this weekend. There are a number of guys and girls talking to the golfers, they must be caddies. The Pro Shop is easy to find. A large sign states JACK FROST CLUB PRO on the door. Entering the shop finds a number of people milling about purchasing items. There is a glass door with JACK FROST lettered on it. Knocking I await an answer.
"Mr. Frost, I am Andy Davis, Mr. Cross told me to ask for you."
"Come in and have a seat. Andy. I will be with you as soon as I am through."
He holds the phone up pointing. Looking about the office, the shelves are full of golf trophies; most with Jack Frost's name on them. There are many pictures lining the walls showing people holding trophies and smiling. I have watched some golf on television but have never golfed. It is something that I could never afford. Even a set of clubs in the second hand store is expensive. The fees for one round of golf would take all the money I earn in a week from my lawn business. Finally, Mr. Frost hangs up the phone.
"Sorry about that, Andy. So, you want to try your hand at caddying?"
"Yes sir. Mr. Cross thinks I can do it. He told me a bit about it."
"I have known Mark Cross since high school; he is a good judge of character. We have had some others come through here that actually humiliated the club. If I give you a chance, you will have to promise you will stay for the full tournament, if you start. I have had a few leave me holding the bag after three holes. I am too old to caddy and, besides, it is very embarrassing for the club. You can appreciate that, can't you?"
"Mr. Frost if you give me a chance, I can assure you that you will not be sorry. Mr. Cross told me it would be a chance to earn fair money."
"Yes, the fees are not bad, plus you will see some pretty good golf. Actually, the biggest part of your income will be tips from the golfers you caddy for. I have heard of caddies being paid up to fifty dollars for a round where the golfer did well, but that doesn't happen too often."
Mr. Frost informs me that the pay is twenty dollars for a round of eighteen holes. Not all golfers take caddies so it is to my advantage to learn all I can about what I am supposed to do. Mr. Frost hands me a Caddie's Guide, then the phone rings. He waves me to sit as he takes the call.
Leafing through the booklet gives me a vast knowledge of what I don't know about golf. The best caddies are familiar with the course they caddy and can offer some information to the golfer, if they ask. I know nothing about golf and even less about the course. There is a sinking feeling in my stomach after feeling so buoyant about the prospects of a better income this summer. Who will hire a caddy that hasn't a clue about the game? Then, a voice is calling me through my mental haze of disappointment.
"Andy ... Andy back to earth."
With a sheepish grin, I acknowledge his call.
"What are your plans for today?"
"Going home and knocking on some doors for more lawn work."
"I have an opening for a caddy; one of the new ones I hired for the tournament has decided that this isn't for him; so, I am in need of someone to cover for him. I have told the client you do not have any experience and she told me not to worry, as long as you are strong enough to carry her clubs. I told her that isn't a problem."
"I would like to try, Mr. Frost. Could you call my mom and tell her I am working?"
"You can do it yourself, in a minute."
He is back to the phone.
"Miss Nielson, I have a caddy for you. Like I told you, he hasn't got any experience; but, he has the intelligence and desire to learn."
"Good, he will see you in the parking lot."
"Andy you will be caddying for Ms. Heather Nielson. All I can tell you about her is she is a divorcee, a very good golfer and seems to be able to attend most tournaments in the area. She is in the parking lot now, waiting for the caddy that never showed. She is wearing a white blouse and red golfing shorts. She has short blonde hair and, you will notice, very blue eyes. You should be able to find her very quickly. Besides being very attractive, she always plays golf to win and she has won several tournaments on many courses. She can teach you a lot!"
After a quick telephone call to my mom, and then parking my bike behind the Pro Shop, I quickly run to the parking lot. Mr. Cross is right; Miss Nielson does stand out in a crowd. What he didn't tell me is she looks like a fashion model! When she sees me coming, her face lights up giving me a smile that makes me blush. Her long legs are smooth and well-tanned. Her clothing is tailored for her body and accents her obvious beauty.
"You must be Andy. I hate to rush you, but I tee off in five minutes. Just follow me with my bag."
Following Miss Nielson is not hard. Her shorts seem molded to her buttocks and the motion is very exhilarating. Looking at her bottom, my five inches stirs. This has never happened before. Following in her wake, her perfume engulfs me. It has the same reaction on me as Jayden's panties. Finally, we get to the tee and it is her turn. Noticing another caddy, standing at the edge of the tee area, I stand beside him. Heather selects a club and takes her shot. Returning the club to me, we all walk down the fairway.
With Miss Nielson golfing last, I watch how the other caddies handle themselves and how they have the next club ready for their golfer. When the golfer approaches the caddy, they usually call out a number. Then, I realize all of the clubs have numbers; Miss Nielson's have small numbered covers on some of them. As she walks towards me smiling, she calls a number; quickly removing the cover, I hand her the requested club.
"You are a quick learner, Andy."
Two things happen when she leans over to accept the club: the vision down her blouse gives me a view of two very well formed, full breasts cupped in a lacy red bra, the view has me blushing when she notices me looking; and my cock bongs into a hardon.
As the game progresses, my education continues. Watching the others, I learn the names of each club in the bag. When Heather asks for a specific club, I am ready for her. Of course, every time she leans over my eyes find her two luscious breasts. The scoring of the game has me confused. That is something I will have to read about tonight. When the game is finally over, it appears that Miss Nielson is the winner in this foursome with a score of four under par, whatever that means. She is very excited.
"Andy, you did very well for the first time out. Will you be here tomorrow?"
"Yes, the second round is Sunday and I will need a caddy again. Are you interested?"
"Of course! What time would you like me to meet you?"
"You can meet me at the hotel across the street, Room 231; say, about seven-thirty. I will buy you breakfast."
"I will be there, Miss Nielson. Thank you so much!"
"Good, please call me Heather. I will pay you for everything tomorrow, if that is okay with you?"
After helping her put the clubs in the trunk, she leaves me and is in a discussion with a group of other golfers. Riding back home, my thoughts are on her breasts and I wonder how they would look if Heather were naked. I bet she has big nipples! Then, another big question hits my thoughts: do Heather's panties match her red lacy bra? Riding a bike with a hardon isn't the best situation.
Mom questions me about how the day went. She is happy for me that I proved myself and is very impressed about Miss Nielson requesting me for tomorrow. She and dad are getting ready to visit a friend, down the street, for an evening out. Even Jayden seems interested. She is dressed in her bathrobe, as she just has showered. She is sitting across from me. In her excitement, she doesn't notice that her robe has opened, giving me a view up to her crotch. It is an impressive view! After looking down Heather's blouse all day, my sexual urges are at their peak! When Jayden notices where my eyes are focused, she surprises me by not telling mom. Usually she takes great joy in getting me in trouble and I try to return the favor. She smiles at me and slowly covers her legs. Her long, blonde hair is pulled back into a ponytail. We are so close that I can smell her shampoo and bath soap; it reminds me of Heather's perfume. Asking mom if we can continue the conversation later, I head for the bathroom.
Quickly undressing, once the door is shut, I caress my shaft, thinking of Heather's beautiful titties. Then, the view of Jayden's legs snaps into my thoughts, which makes me wonder just how Jayden would look lying on my bed with her legs spread. The images that are on the net, have given me ample input for my imagination. In the shower, enjoying the refreshing water, I feel a draft, like someone opened the door.
"Andy, I have to go pee and mom is using the bathroom downstairs."
My hair is covered with lather and suds are running down my face so my eyes are closed.
"Well, go ahead and pee and then get out of here."
Why couldn't this have happened when I could see? Visions of Jayden, peeing fill my mind, as her stream hits the water in the bowl. My imagination is at its peak wanting to see her doing her job. Assuming she has left, after hearing the flush and getting hit with a blast of hot water, I continue my shower. The sudsy lather on my cock makes it easy to jack off, giving me a much needed feeling of relief. Then, I hear a sound. Unbeknownst to me, Jayden did not leave the bathroom. The shower curtain is just open enough so she could see everything, including cum shooting out of my cock.
"Jayden, what are you doing?"
"Watching you! Do you do that all of the time?"
I have pulled on the curtain, closing off her view; however, it's a bit like locking the barn door after the animals have all been stolen. What was a very nice hardon is now just a shriveled stub; not only because I came already, but also the fact that my sister watched everything. Thank goodness she couldn't read my mind because, as the cum gushed out of my cock, my mind was on her legs and the wonders between them.
"Rub your thing and make it spit again. That was really cool!"
"You should have left after you peed. I thought I was doing you a favor."
"You did. Can you do that again?"
"You had better go; if mom or dad catches you in here there will be hell to pay!"
"You don't need to worry about them. Mom has dad in knots; he has been ready to go for over an hour, but mom is still in the downstairs bathroom. When she comes out, he will have her out the door before she can think of something else. So, can you do it again?"
"Maybe, but you have to do something for me."
"You have to show me yours so I can get hard again."
Instead of leaving in disgust, Jayden looks at me with a funny expression on her face. She is still dressed in her bathrobe so she is likely naked underneath. My small snake isn't doing anything except hiding. Since Jayden doesn't make a move, I rinse the soap off my body and grab a towel. Jayden watches every movement. No point in trying to hide it now as she has seen everything as it is. Drying my hair has my limp cock moving up and down. Jayden's eyes are wide and shining, as she never takes her eyes off me. Finally dry, I tie the towel around my waist and go to my room. Both of our bedrooms are upstairs. Mom and dad have a very large one downstairs. Walking down the hall, Jayden follows me. When I try to close my door, she pushes on it and comes into my room.
"What are you doing here?"
"I am still thinking about what you asked me. Would looking at me naked help?"
"You are very pretty and when a guy sees a pretty woman it gets him excited."
Shit! Why did I say that? That is my cock doing my thinking for me. Again, Jayden doesn't leave or yell; she just looks at me. When I drop my towel, her eyes are quickly riveted onto my cock, which is starting to grow in spite of my request to see between Jayden's legs. Then she surprises me by dropping her robe, sitting in a chair and spreading her legs. She is beautiful! The strain of her spreading causes her soft, puffy lips to open, giving me a view of a very pink moist opening. So, this is what I have been missing! I don't know why but instantly my cock gets hard. The movement of my shaft does not go unnoticed.
"Wow, Andy! I did that?"
"You are the first girl I have seen between her legs. I don't know what it is but I feel excited just looking at you. Can I get a better look?"
"Sure, if you want, but I want to look at you too."
On my knees, with my face about three inches from her beauty, I can feel her sexual heat and sure as hell can smell her pussy juice. It reminds me of the smell of her panties. Shit! Of course that is what her panties touch all day so, of course, they will smell like her pussy and a slight odor of pee.
"Can I touch you, Jayden?"
I might as well go for broke. Either she will or she won't let me, but the desire for more is very strong.
"Maybe, but I have to see you first."
On my back in bed, my cock sticks straight up. Jayden is now beside me inspecting.
"You can touch it if you like but be gentle. It is very tender."
Her small, warm hand reaches out and touches the shaft; then, she pulls back quickly. Grabbing her hand, I wrap it around the shaft. Then guide her in a pumping motion.
Does this feel good?
"It won't break; just be gentle."
She watches my foreskin cover then uncover the bulbous head with each stroke. It is a light purple, as all of the blood in my body must be there by now! Jayden's hands are so soft and warm. This is something I could enjoy all night, even if she is my sister.
"Okay, you can touch me now."
Crawling up beside me, she sits with her ankles crossed, spreading her pussy to the max. Nothing prepared me for the soft moistness. Her heat spreads to my fingers as I probe. In two knuckles deep, Jayden sucks in her breath and falls back on to the pillow with her legs spread wide. Moving between her legs, on my stomach, my face is again within smelling distance of her very wet opening. Her scent is like a siren of old, beckoning me to immerse myself into her essence. When my lips touch Jayden's love lips, her eyes open with a flash.
"Andy, what are you doing? Why are you kissing my pee-pee?"
"Did you like it?"
"It feels different."
Really not knowing what to do, my tongue and my lips continue their learning experience. One thing I quickly learn is that every time my tongue touches a bump on the top of Jayden's pussy she takes in a deep breath. It is small, but I am able to actually suck on it. The sound that emits from Jayden has me thinking she is hurt.
"Did I hurt you Jayden? I didn't mean too."
"No, it doesn't hurt, it feels good. Keep doing it."
Her opening is so tight that my tongue can't enter very far. Jayden brings her knees up and lifts her cunny to my mouth. It seems the more I lick the more juice seeps out. It has a funny taste. Finally leaving her panting, I can't help but notice Jayden's small tight bum hole.
"Jayden, roll over on your stomach."
Jayden's bum cheeks are like two small melons. They are well defined and so soft. Spreading her cheeks gives me a wonderful view of her small tight rosebud. This morning I would have never thought that looking at my sister's asshole would be so sexy. When I run my finger over it her body twitches.
"What are you doing, Andy?"
"Examining your pretty bum hole; it looks so sexy."
"My bum hole is sexy?"
"Jayden, this is my first experience looking this close between a girl's legs. Everything looks so soft and sexy. Look at my cock; it is as hard as can be."
From all the reading and listening I have done, I realize that, somehow, my cock is supposed to go into Jayden's pussy. One of the guys had a video of a guy and a girl fucking. Remembering watching the guy's cock slide in and out of the girl's pussy still gets me hard but can Jayden take my cock inside her? My tongue couldn't get into her when I tried and my cock is longer than my tongue. Jayden seems fascinated looking at my fully erect cock.
"Can you make it squirt again?"
After seeing Jayden close up the urge to masturbate is so strong; actually, if it were possible, I would love to try to put it in Jayden's pussy. Grasping my shaft, stroking, Jayden settles in to watch.
"Why don't you do it for me?"
"Wrap your hand around it, squeeze softly, and pump it up and down. Then you can feel it pump and squirt really close-up."
Jayden was never one to refuse a challenge. With me on my back, she grasps my shaft and starts to pump. Now this feels really good! If I had known how it feels to have Jayden stroke me, we could have been doing this for a couple of years. Jayden's body showed development very early with well-toned legs, bum and hips that I saw; often running after her to kill her for something she did to bug me.
The desire to cum is building up rapidly. Jayden is leaning over the head of my cock, really enthralled by the movements of my foreskin. Not being able to hold off, cum shoots straight up coating Jayden's mouth and nose. When the first blast hit her, she opens her mouth to gasp; wrong move, as the second string finds the opening and hits her in the back of the throat. Now she is gagging and chocking.
"Andy, that stuff won't hurt me, will it?"
"No, Jayden, I read that some girls like the taste of it."
"It doesn't taste too bad; kind of salty."
"Guys at school told me that some girls suck a guy's cock till it shots then they eat the stuff. I don't know if it is true."
"So, no other girl has done this for you?"
"No, you are the first and boy did it feel good!"
Then she really surprises me by leaning over and licking the glob of cum still clinging to the top of my cock. Flicking her warm tongue over the head nearly has me cum again. Wow, this feels good! Jayden engulfs the head in her mouth, looks at me with her big blue eyes shining and starts to suck. This must be what heaven is like.
Jayden gets up and turns out the light. Instead of leaving, she lays down beside me with her face at my cock. She pulls at me to lie on my side facing her. I watch as she adjusts a pillow and then she opens her mouth engulfing my cock and starts sucking.
When the alarm goes off the next morning, I am shocked to find Jayden still in bed with me. She is now curled up in my arms, body-to-body; spoon fashion. Fortunately, mom and dad never checked on us or we would be in deep shit! Gently waking her, she smiles and leans over and kisses me. Shocking myself, I kiss her back and my hands run all over her body and end up between her legs. She is so wet.
"Jayden, I have to caddy this morning. It was fun last night. I hope you want to do it again."
"Oh yes, big bro, it is fun; besides, you don't taste too bad."
Thirty-five minutes later, at Heather's hotel room, I knock softly on door number 231. It is seven-thirty one.
"Come in, Andy, I am nearly ready."
Letting myself in, I survey the room. The bed has been obviously used as the outline of Heather's head is still in the pillow. My imagination is now working overtime. With what Heather exposed to me yesterday, my boner starts to grow.
"I won't be long, Andy."
Looking up, Heather surprises me as she is only dressed in a lacy blue demi bra, exposing a lot of bare skin. The matching panties are molded to her body. She has beautiful, flawless skin that seems to glow. Her tummy is flat with a deep indentation for her belly button. Looking lower, I am sure that those are long, dark brown hairs escaping her panties. Heat runs through my body as my blush rushes through me.
"Oh, that is cute, Andy. You are blushing! Haven't you seen a woman before?"
She disappears into the bathroom before I need to answer. The vision of her lush body is vivid in my mind. With her looks, and her sexy body, she must have a boyfriend. Wondering what it would be like in bed with Heather, I softly rub the protrusion in my pants.
To make matters worse, Heather's other bra and panties are in a pile on the chair beside her bed. The bra is red, like the one she exposed me to numerous times yesterday. The panties are very lacy and look very skimpy. Dare I touch them? Moving closer, my ears are straining to hear any indication that Heather is returning to the bedroom. Water is running in the bathroom so she could be brushing her teeth. Quickly moving to the chair, my hand touches the softness of her lingerie. Her panties feel so sexy. They are so small that closing my fist would hide them in my hand. Putting them back, I notice three, tight, brown curly hairs attached to my palm. Are they Heather's pussy hairs? Quickly gathering them, I put them in my wallet. All my body is twitching now. Then the door opens. Heather is completely dressed in a snappy golf outfit.
"Ready for breakfast?"
Stammering yes, we leave the room and head for the restaurant. After the meal, she leads me to her car and we drive to the course.
"I will drive you back to the hotel so you can pick up your bike."
Heather smells so good. In the confines of the car, her perfume is overpowering. She is wearing a very loose golf shirt, similar to that of yesterday. She keeps looking at me, smiling. Her full lips are coated with a very soft pink lip-gloss. She has perfectly straight and very white teeth. It is nearly impossible not to stare at her beauty. I was never so glad to see the driveway to the golf course.
Heather has a very good day. She wins again. In her enthusiasm at the eighteenth hole, she grabs me and gives me a kiss and a hug. Her solid breasts push against my chest and my cock reacts. Her lips are so soft and moist. I am sure that her tongue touched my lips. The rest of the foursome, and the other caddies, are laughing at my embarrassment. As we walk back to the clubhouse, I will my erection to go down so as not to embarrass me any further. She stops in front of me. We nearly have a collision, as I have been mesmerized watching her bum cheeks sway back and forth.
"Andy, you are my good luck charm. A new caddy, willing to learn, changed my luck. This is the first tournament I have won in nearly four months."
Again, I am in her arms being kissed. Embarrassed, and blushing, I gather up her golf bag and we continue walking to the clubhouse. She is rehashing her last putt with another golfer. It is easy to tell Heather is proud of her win. At the car, she leans over to slip off her golf shoes, giving me a wonderful view of her breasts hanging down from her body, just being held in place by her skimpy bra. Her soft, white globs look so striking! What would it be like to actually touch and kiss them? Unfortunately, she catches me staring. She smiles and says nothing.
"Andy, I want you to be at my side when they present the trophy for this tourney. You were an important part of my win."
"But I didn't do anything to help; I really don't know anything about golf."
"You were my inspiration. I don't know what it was; but, whatever it was; it made a world of difference!"
It took nearly two hours for the presentations and all of the stupid speeches by so many people. It seems like the only person that didn't speak was the young guy sweeping the leaves from the walkways. Finally, Heather signals me that we are leaving. There is a rumbling in my stomach. The only thing I had since breakfast was a donut and a bottle of water.
"Andy, I bet you are famished. I know I am. Let me buy you dinner."
"No, I better go home; you have been good to me and likely have other people you want to be with."
"Actually, you will be doing me a favor, as I would be eating alone. Too many guys hit on me. I will give you a ride home after dinner. We can put your bike in the trunk."
Looking at her, even dressed in her golf outfit that she has worn all day, Heather is a remarkable looking woman. If I were an older guy, she certainly would get my attention. Just looking at her now has my cock stirring. Thinking about last night with Jayden has my cock tenting my slacks. Jayden is waiting for me to come home. Heather notices and smiles. I ask.
"Don't you have a husband?"
"I did, but I got rid of the bum three years ago; once burned twice shy. The only thing good about it is the alimony he is paying every month. It allows me to enjoy golf all year."
"I will have to call home and tell my parents."
"That is fine; you can call from my hotel room. I would like to change and freshen up anyway."
Securing her clubs and bag in the trunk, we head for the hotel. Heather's voice is so soft, so sexy. My woody appreciates her attention and will not go down. Heather notices me squirming, trying to get my cock in a position so it doesn't embarrass me.
"You're going to be a good caddy, Andy. You pick up things very quickly. You watch and learn. That is a very good trait."
"Thank you, Miss Nielson."
"Call me Heather. We have been so close for the last two days; it feels like we are family."
Looking at Heather's luscious lip-gloss coated lips makes me want to see a lot more of this part of my new family. I still can't believe she doesn't have a boyfriend or a husband. After parking, I follow her beautiful body to her room. She shows me the telephone, excuses herself, and goes into the bathroom. The sound of the shower has my imagination working overtime.
"Mom, Miss Nielson won the tournament today. To celebrate, she wants to take me out for dinner. She said she will drive me home afterwards."
"Yes, she sounds like a very good golfer. Enjoy your meal!"
"Thanks, mom, I will likely be home before eleven."
The shower stops. My stiff cock is really tenting. This could be embarrassing. The door to the bathroom opens and Heather walks into the room with a towel wrapped around her body. Her hair is piled on the top of her head with some strands dangling down the side of her face. She looks like a fashion model.
"I will only be a few more minutes, Andy. Sit down and watch some television."
Television is the furthest thing from my mind. I can't get enough of Heather's body. She can see I am staring at her. When she leans over her suitcase, the towel rises giving me the shocking view of her bare bum. All daylong I have looked at her backside, as I followed her on the course, wondering. Now it is in front of me naked! My imagination has me actually seeing part of her pussy. The dim light in the room is playing tricks with my sight. Then Heather catches me staring.
"You like what you see?"
At a loss for words, my mouth opens but no sounds come out. Slowly, Heather walks towards me and the towel slides down her breasts to the floor. She stops in front of me. Her pussy is at eye level. Unlike Jayden's her love lips are heavy and very puffy. She has a small tuft of hair, just above her slit, shaped like a heart. Her inner labia are protruding, looking like a thick, soft, pink blossom. Heather has a very large button on the top of her pussy, about the size of my thumb. She is close enough that the scent of body soap and her sex fills my nostrils. What am I to do?
"You can touch me, Andy, I won't break. I have watched you all day looking at me. You're not a bad looking hunk of a man yourself, in spite of your age."
Without warning, she grasps the back of my head and pulls my face into her delicious pussy. Her seeping love juice covers my face; automatically, my tongue licks. Heather's taste is more defined then Jayden's. Pulling her labia with my lips causes Heather to moan with pleasure. Moving upwards, I grasp her clit and suck. This nearly causes her to lose her balance.
Grabbing my ears, she gently guides me to the large king sized bed. Still standing, she guides my mouth to one of her large, rosy nipples. As I suck, her hands unbuckle my belt and then slip into my shorts, grasping my engorged cock.
"That is a nice woman pleaser you have, Andy. Have you been with a girl yet?"
"Not really, have you tried?"
"Just a bit."
"So, you are still a virgin?"
"Would you like to remedy that?"
How does a fifteen year old answer that? Prior to yesterday, all my sexual experience was my imagination and my hand. Jayden certainly helped with my education last night. Now, with my head bouncing up and down, Heather moves me to a sitting position and then removes all my clothing. She seems to be impressed by my hard cock. In the shower at school, I am not the longest; but, I am the thickest. Heather's hand feels exhilarating as she caresses me.
"We are going to put this to good use; then, we will go and have dinner. I plan on having dessert first. You are my dessert, Andy."
Heather, on her back, looks at me and then spreads her legs wide, giving me a view of the wonders of a mature woman. Her love lips glisten with moisture. Crawling on the bed between Heather's legs, I can't help but admire how stunning her mature pussy looks. Will Jayden's develop to look like Heather's? The scent of her sex fills my nostrils. The next natural course is to bury my face. Heather is more than just wet when I force my tongue between her labia: a small stream slowly seeps out. Quickly lapping the excess, my mouth finds her clitoris once more. Sucking it like a nipple, Heather quickly starts moaning and gently lifts her hips, pushing against my face. Her hands are on the back of my head, pulling me deep. Her body stiffens and then she shudders, producing a very large exhaust of her breath.
"As I said, Andy, you are a quick learner. For a boy who hasn't had any experience with sex, you certainly rang my bell. I will have to thank the club pro for introducing us. You know, you are the first man I have had between my legs for over two years."
She called me a man! Heather has both arms up beckoning me to climb on top of her. From everything the guys talked about at school, this is when I get to fuck Heather's wet pussy. Her soft breasts feel good under my chest. Heather startles me when she grasps my cock, moving her body to guide me. The sensation of my shaft being encompassed by her moist cunt is indescribable! My immediate thought is, 'Can I do this with Jayden?'
"That feels good, Andy. It has been a while since I have had anyone make love to me."
She sees the bewildered look in my eyes, smiles, and then says.
"Oh, I have had many volunteers but they looked at me as a trophy, not as a woman to love. If I had succumbed to anyone of those wolves, I would have been the talk of the golf club. That is something I don't need. It took a while to get their wives to accept me as a player and not as a divorcée on the make."
While she is explaining, my body, automatically, is pumping in and out of her soft, moist cunt. The feeling is amazing! Heather wraps her arms around my body and pulls me deep into her; then, she looks at me and kisses me. It is my first passionate kiss: long and tantalizing. A tingling sensation focuses in my cock. It feels like when I masturbate but even better. Heather is now meeting my thrusts with her hips. We are really pounding each other.
"Heather, Heather, it feels like I need to cum."
"It is okay, Andy, let it go. I am happy to take your cherry. Next time you will have to try and satisfy me."
All I heard is "next time" and then strings of cum seemed to fly out of my cock and deep into Heather. She intertwines her legs in mine and pulls me deep when I start to erupt. As the wonderful sensation passes through my body, it is replaced by the feeling of total exhaustion. My full weight is on Heather. She is now humming, as she gently strokes her fingers through my hair.
"You were good, Andy. With practice you will be even better."
We must have laid in each other arms for nearly an hour. Today is what memories are made of! Finally, we get up and Heather hauls me to the bathroom and we have a shower together. Washing her pussy, I was mesmerized at the volume of cum that seeped out of her. What is even more fascinating is the fact it was my thick cum.
By the time we get to the restaurant, my appetite is ravenous! During the meal, Heather rubs my legs many times with her feet. She must have slipped off her sandals. She brings her foot between my legs, massaging my now engorged cock.
"Well, Andy, it feels like we should go back to the hotel. Are you up to it?"
Once undressed, lying in bed with Heather, I try to recall all the things I have read about sex. One subject comes to mind: foreplay. Several articles stressed that women enjoy foreplay as much as or more than actual fucking. After several kisses, my mouth finds Heather's earlobes. My mind is questioning this tactic but it is one of the suggestions concerning foreplay. I can't fathom why chewing a girls earlobes is considered sexy. However, the way Heather reacts confirms the article is correct! Her body twists and turns as she softly moans. Her hands are all over my back, softly caressing me. Three times her body shudders, as if she is experiencing a climax. I must be doing something right.
There are a number of things I would like to try but it won't be tonight. Heather grabs me and puts my cock at the opening of her cunt. Nature takes over. Recalling that it takes woman longer to cum, I do my best to hold off. As the urge to cum becomes nearly unbearable, I stop and wait for the feeling to subside. This happens three times before Heather stiffens and raises her hips to me. She has surprising strength and nearly bucks me off her body when she does cum. Finally, the need to cum overcomes me and I flood Heather. We are both breathing heavily, exhausted.
"Andy, I can't believe what just happened! It has been years since anyone has been able to bring me to a vaginal climax. Thank you!"
She kisses me and gives me her tongue. It tastes like the dinner mints we had. Shortly after that, we have our second shower together. Once dressed, she pays me for the caddying, including a very sizable tip that I try to refuse.
"No, Andy, you earned it. I don't mean in bed, although you were very good there. By the way, I golf at Campton next week; do you want to be my caddy? It is a three day affair; so, we would have to stay overnight Thursday, Friday and Saturday."
Campton is a town fifty miles from Abbotsville. It sounds great but mom and dad may have something to say about it.
"I would like to, but I have to ask my parents."
"Maybe, when I drop you off, I can speak to them. Do you think that would help?"
"Would you? I really would like to go!"
After lifting my bike into the trunk, we have to get some rope to tie it securely. It is nearly nine when we arrive at my home. All the outside lights are on and, as soon as we pull into the driveway, mom and dad open the door. When Heather gets out of the car they walk towards her with Jayden following. Jayden looks at me with a smile that tells me she is glad to see me.
"Mom and dad, this is Heather Nielson, the lady I caddied for this weekend. She wants me to caddy for her next weekend in Campton for three days. I told her she would have to ask you."
"Yes, I would like Andy to caddy for me. We got along well together and I won the tournament. I would appreciate it if you would allow Andy to caddy for me next weekend too. We would have to stay over for three nights. I will pay all of the costs."
My dad is ogling Heather. He has always had a wondering eye and mom keeps reminding him that every female is off limits. He always laughs and says he is just looking. It has been a game they have been playing for years.
"I can't see why not. Is it okay with you, Harold?"
"Of course! It's time Andy gets to see a bit of the world; besides, Campton isn't Alaska."
"Then it is settled. Andy, I will call you Wednesday at seven to give you the details. Good night all; it has been a pleasure meeting you."
Once my bike is out of the trunk, we all watch and wave goodbye as Heather disappears down the street. When I tell dad the amount of money I made he is impressed.
"I am proud of you, Andy. I want you to put a portion of your caddying money aside for your collage fund. It isn't that far off, you know."
Jayden and I follow mom and dad into the house. Jayden is wearing her housecoat. When she gives me a particularly hard jab in the ribs, I look at her ready to whack her. However, all she wanted was to get my attention. She is holding her robe open giving me a look at her naked body and her luscious peach; immediate hardon! She has no idea of what I have planned for her. My experience between Heather's legs will be a guide for Jayden's education.
In the kitchen, mom and dad had many questions about golf and what a caddy actually does. They were sitting on one side of the table and Jayden and I were facing them. During the conversation, Jayden didn't say a thing but her hands were rubbing my very stiff cock. Once, when she squeezed it, I caught my breath.
"Andy, what is wrong? Don't you feel good?"
"I am all right, mom. I guess I am just tired. It has been a long, hot day."
"Would you like something to eat?"
"No thanks, mom, we had a very good meal at the restaurant."
"Maybe you should go to bed; we can talk more about this tomorrow."
Jayden is off like a shot upstairs. In my room, I strip and slip into bed on my back. My cock is pointing to the sky. Thinking about this evening, I can't believe it has been deep in Heather twice and both times I shot my cum. Jayden looks in, questioningly; I pat my bed and she slips into the room, closing the door. Her housecoat drops to the floor. Crawling into my bed, she grasps my now very hard cock.
"Andy, I have been waiting for you to come home. All I thought about is what we did last night and I want to do it again. I talked to Brigitte today and she told me that guys actually push their cock into girls. Have you ever done that?"
Brigitte is Jayden's best friend and a tease. She takes great pleasure in making me as uncomfortable as possible. She and Jayden often have sleepovers and she takes great pains to make sure I get a good look at her semi-naked body as often as possible. She has small titties and a great ass. She has a chocolate complexion as her mom is black and her dad is white.
"Yes, Jayden, I have."
"I can't tell."
"Does it feel good?"
"Yes it does, and it is fun doing it."
"Do you think I can do it too?"
Jayden sits up, spreads her legs reaches down, and spreads her lips exposing a tight opening. Looking at her, I look at my cock, hoping it will fit in my sister. Jayden seems to want to be done as much as I want to do her.
"What do I do, Andy? I want to try it."
"Well you lie on your back, spread your legs and then spread your pussy like you are doing. I will stick my cock in your pussy. It supposed to go right in."
In all my vast experience talking about sex, the guys had mentioned the term 'cherry' but the actual physical membrane was very fuzzy in explanation. It other words, I don't know anything about it! After all, my only experience is with Heather and that all just happened today.
This is the start of a very interesting part of my sex life. First Jayden, then Heather, and the thought of three days with Heather next weekend promises to be very, very interesting, but that is another story. Besides, Jayden is waiting!
This story is a work of fiction. Names, characters, places, and incidents either are products of the author's imagination or are used fictitiously. Any resemblance to actual events, locales or persons, living or dead, is entirely coincidental.