Chapter 2

Special thanks to Phil Gorman 2015 for his expertise in editing and proofing.

Story intro: Andy continues his quest to become a versatile caddy. His sexual learning curve expands with more adventures with his sister, Jayden, and others. It is shaping up to be a memorable summer for a fifteen year old.

This summer promises opportunities for better earnings and learning experiences. Two things really have changed my life: first, my fourteen-year-old sister, who has become my best friend in the world; and second, my meeting of a very beautiful woman, Heather Nielson, who is a very talented golfer.

The opportunity to become a caddy was the catalyst. Mr. Cross, one of my summer lawn work clients, introduced me to Mr. Frost, the golf pro at the local club. He took a chance on me and allowed me to caddy for Ms. Nielson. Actually, for me, it was being in the right place at the right time because the caddy that had been hired quit and left Mr. Frost in a bind. Over the two-day event, Heather Nielson managed to win the tourney. Later, in her hotel room, at the end of the second day, she introduced me to the incredible world of sex. Something, I hope, I can perfect with the willing participation of Jayden, my fourteen-year-old sister. Jayden and I dabbled with touchy feely, the night before my learning experience with Heather.

A bit about myself: my name is Andy Davis. At fifteen, I am tall for my age. I am five foot eleven, weighing 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. I have always considered my sister as a pain in the ass; but, after our evening exploring her young willing body, my view rapidly changed. I am looking forward to teaching her all of the things Heather has taught me.

One of the fantastic things to come out my first caddying experience with Heather Nielson is the fact she asked me to caddy for her this coming weekend at Campton. It will require staying over for three nights. Heather asked, and received, my mom and dad's permission to have me accompany her as her caddy. It promises to be a very exciting weekend!

Thinking about what could happen next weekend, over and above caddying for Heather, keeps my mind busy as I complete my lawn chores for my many clients. Another change that has become very evident, I am now aware there are many very attractive women in my group of clients. After my experience with Heather, I look at women differently. Surprisingly, as I look at them, many are looking right back at me. This is something that never entered my mind in years past. I am regularly dressed in cut-off jeans and a muscle shirt. When it is really warm, I lose the shirt and go bare-chested as my dark tan attests. My activity in sports, and my summer jobs, keeps me fit and my body is muscled in the right places. One client, Mrs. Serpa, is particularly interesting. Every time I mow the lawn, she is sunning herself in the skimpiest of bikinis. She always asks me to join her for a cold soft drink after the job is done. Today, she sat across from me with her legs spread. The tiny bit of cloth covering her pussy is molded to her. She has larger love lips than Jayden. This "woman" thing is all new to me. I certainly want to do more of what I did with Heather. What do I do next as far as Mrs. Serpa is concerned?

Nothing happens today; but, when she pays me, she manages to bump into me three times; once with her hip and twice with her large boobs. She sure is tempting! The Serpa's have a very large lawn and they are one of my highest paying clients, not to mention the tips they always give me. I don't want to jeopardize it but I would love to get to know Tara Serpa a lot better. She always smells so good.

My nights are all Jayden as we attempt everything that Heather taught me. She enjoys everything we have tried so far and we will be able to attempt actually having sex tonight. Mom and dad have a meeting to attend, leaving us to ourselves for at least four hours. For the last three nights, Jayden has come to enjoy sucking my five inches till it creams. The little nymph has developed a taste for cum. In return, I spend ample time between her thighs licking and tonguing her tasty peach and her tight rosebud. It is a perfect relationship.

Arriving home, Jayden is in the study waiting for me. She is dressed in tight, white shorts that are glued to her bottom and pussy and a blue tube top with her hard nipples protruding sexily. Smiling, when she sees me, she moves close to me and draws her hand over my hardening shaft.

"Are we still going to try tonight?"

"I want to, do you?"

"Of course! I talked to Brigitte and she told me the first time a girl does it she breaks her cherry and it will bleed a bit. Do you know what she is talking about?"

"Not really. The guys talk about things like that all of the time; but, honestly, none of us actually know what we are talking about. Losing your cherry has something to do with having sex for the first time."

"Do you have your cherry?"

"No, I have had sex."

"Really? With who?"

"Sorry, can't tell you. It isn't something a guy is supposed to babble about; but, I can tell you, it really feels good being inside a woman."

"A woman? I thought you did it with a girl?"

"Same thing."

"I can't wait. You better go and talk to mom; she has been holding dinner for you."

In the kitchen, mom is cleaning up the dishes. She has her hair in curlers. Jayden gets her looks from mom. Mom has her shirt tied around her waist, showing a large portion of bare skin. She is good shape and a lot of my friends tell me they would like to do her. It is all talk, as I think I am the only one with any experience so far.

"Hi mom! When are you and dad leaving?"

"Well, I have to finish my hair and get dressed. Your dad is likely ready now. You know him."

She is laughing. Mom is never ready when dad is. Dad is a fussbudget, always prancing around the living room, ready and waiting for mom. One of these days, he is going to have a bird.

"I have your dinner in the microwave: just hit 'on' and it will be warm. You can clean up your dishes when you are finished."

"Ok mom. I don't want dad to have an attack because of me. Go and get ready."

Watching mom leave the room reminds me of following Heather around the golf course. I never thought of my mom as a sexy person before, but watching her bottom now makes my five inches sit up and take notice. Her bottom reminds me of Heather's. For two days, last weekend, that was what I did all day; follow her bottom from one shot to the other. All the new sexual awakening is a result of my new experience with Heather. We had full-blown sex, twice on the weekend; then, today, looking at Mrs. Serpa, and now mom's soft curvy bum, reminds me of what Heather has taught me to appreciate.

Finishing dinner, I clean the kitchen. Jayden comes in twice, each time with fewer clothes on. She has showered and is in her robe. Each time she opens it and gives me a look at her mouth-watering, young body. All she is wearing is a very sexy pair of yellow panties. For some reason, looking at her partially nude is a real sexual high for me.

In the living room dad is pacing, as usual, waiting for mom.

"Your mother will be the death of me yet. She accepts these invitations and times from our friends, only to spend hours getting ready, and we are always the last ones to arrive at any function we attend. It isn't fair."

"Dad, mom will never change, you know that?"

"Yes, I do. I think she takes great pleasure in making me squirm."

Dad is laughing when he says that.

"You have a good time. Jayden and I will be fine."

"I notice you and your sister aren't fighting and tattling on each other. What happened? Did you two grow up?"

"Something, like that, I guess; I have too much on my mind with my lawn jobs and caddying. I am exhausted when I get home."

"It is nice, anyway, regardless of the reason. Now I can concentrate on your mother's tardiness."

Heading upstairs and into the bathroom, I quickly strip and get into the shower. This time, when I feel a draft, I know Jayden has come into the room. She opens the shower curtain, standing there naked.

"Do you need any help?"

"Jayden, you are taking a big chance! What if mom comes up?"

"You know that will never happen! Can I help?"

Having Jayden handle me has become one of my daily pleasures. She takes so much enjoyment in caressing my shaft and really enjoys making me cum.

"Okay, but you can't make me cum. I need to be really hard to put it in you."

"That's not fair! You know how much I like sucking you and swallowing your cream. Brigitte didn't believe I did it!"

"You told Brigitte you are sucking my cock?"

"Of course, we don't have any secrets. She is my best friend and now she is jealous and wants to try it too."

"With who?"

"You, dummy. Don't you like Brigitte?"

Brigitte is also fourteen, a bit taller than Jayden and is very attractive. She has a chocolate complexion and is developing faster than Jayden. Her long legs and shapely bottom have gotten my attention more than once. She actually has boobs and wears a bra. I would love to see her lovely lips sucking my cock. She must be something to see naked. Accepting her in my group of sexual friends is a no brainer!

"I didn't know you told her everything. I think it would be great if she could come over some evening. Sure, she can suck me!"

"I will tell her you said so. When?"

"It will have to be sometime next week, because I am going to be in Campton all weekend. I leave tomorrow night with Ms. Nielson."

"Oh, Andy, I was hoping we could play more with each other, especially if you can do me tonight."

"We will be doing things every night I am home, Jayden; that, I promise."

"Did you hear the door slam? Dad must have pushed Mom out the door."

We both go to the window and watch as the car moves out of the driveway, heading down the street. Jayden wraps her arms around my neck and kisses me. Her soft hand is caressing my cock. My hands cup her soft ass cheeks my, finger finding her tight rosebud. Jayden feels so good against me, bare skin to bare skin. Breaking our kiss, my lips move to her nipples sucking one, and then the other, getting her usual reaction of moaning and pulling my face into her flat chest.

"Andy, come on, let's go to my room. I can't wait to feel you pushing into me. Don't laugh, but I have been looking at my pussy in the mirror wondering if you will fit. I really hope you can."

Following Jayden's naked body to her room reminds me of how things have changed in the last two weeks. Before, when I was following her, I was usually in a full-out run trying to get my hands on her to wring her neck for something she had done to piss me off. Today, it's to enjoy her company and her body. My cock is hard and extended, bobbing up and down as I follow her tight bum.

"What do I do, Andy?"

Jayden is on the bed, on her back, with her legs extended. She looks like a dream come true! The curves of her body are so much more defined and appealing. She seems content with the effect she is having on me. Slowly she brings her knees up and then spreads her legs. Her peach slowly opens, beckoning me to show my appreciation for my young sister. Between her legs, my mouth finds her pussy; attaching to it, like a vacuum, I suck and lick her love juices. As usual, her hands are on the back of my head pulling me deep into heaven.

"Andy, I love it when you do that to me. It makes me feel so good."

Once her body has trembled and stiffened three times, I raise my face and look at her; slowly, her eyes open, she smiles and then laughs.

"Your face is all wet, Andy. I really must be wet. I have been thinking about this all day."

Slowly positioning my body over her, my cock standing rigid from my body, I am ready to fuck my sister for the first time. Jayden looks so serene and so beautiful. Raising her arms she grasps my neck, pulling me down and whispering.

"Do it, Andy. I want to feel you in me now!"

The mushroom head of my cock is exposed, the foreskin pulled back. Once it is against Jayden's pussy, we keep in eye contact. Her eyes are now bright and alert as the pressure against her virgin pussy increases. Slowly, the head disappears into her warm moist opening. Jayden is breathing in gasps from the excitement at this point. When I hit a blockage, my mind registers that "this is my sister's cherry." Several times, I push against it and then pull back. Jayden winces but doesn't say anything. She is trying to help by raising her hips against the onslaught of my cock.

"What does it feel like?"

"Like something is stretching, it stings a bit. How long does this part take?"

"I don't know; you are my first cherry."

The strength Jayden displays surprises me as she pulls my face to her lips and kisses me deeply.

"I love you, bro. I can't believe we are doing this."

"I am glad we are."

Then it happens as I try to arrange myself above her. Jayden moves her arms in such a way that she puts me off balance; the full weight of my body, centering on my cock shaft, pushes downwards. Like a flash, the full length of my cock is buried in my sister. The shock on her face is priceless. Her mouth is open but no sounds are coming out.

"That hurt."

"I lost my balance, Jayden. I am sorry."

"Don't be, bro, I feel so different; kind of full."

Again, we are kissing as the realization sinks into both of us that my cock is buried deep in Jayden. The heat on my shaft is nothing I have experienced before, even with Heather. It is so much different from fucking Heather. Jayden's pussy seems to be grasping me, squeezing. What a sensation! With my knees, I spread Jayden's legs to their extreme and slowly start pumping in and out of her tight pussy. Jayden still has her arms around my neck in a bear hug, not giving an inch. My strokes are very short and the feelings I am experiencing are unbelievable. Cumming, for me, is a certainty; but, will it be for Jayden?

"What do you feel, sis?"

"I feel good. It doesn't hurt any more. It feels so different. Does it feel good for you?"

"Jayden, this is the greatest! We should have been doing this for years, instead of fighting. I am going to cum, can you?"

"I don't know, Andy; everything feels so good, so different. I can feel every move you make."

My option of holding off cumming is coming to an end. The urge to ejaculate is so strong. With Heather, she seemed to cum and cum; with Jayden, being her first time, I have no idea if she will cum or not. Then it happens. Gush after gush leaves me, flowing deep into my sister. When I relax, lying on Jayden, she squeezes me tightly.

"Andy, that feels so good. I could sense every squirt you made. It feels so hot in me. I love you."

"I never thought I would ever say this to you, Jayden, but I love you so much. I hope we are this close all of our lives. Today is the best day of my life, so far!"

The balance of the evening we talked and then we fucked again. I managed to fuck her three times before we part. After mom and dad came home, I waited for an hour for them to fall asleep and then returned to Jayden's room. We slept in each other's arms that night. At breakfast, mom told us about how she and dad had a good time that evening, in spite of her making dad wait. She told us that the fact that we weren't fighting allowed her and dad to enjoy themselves, not having to worry about us killing each other. Jayden and I just looked at each other.

Our conversation was about my trip.

"Andy, this is an opportunity to show the world that you have been brought up to respect others. Please act like a gentleman, at all times. Help Ms. Neilson as much as you are able. I am proud of you."

"I will do my best, mom. I have to pack and then do my lawn jobs for today and tomorrow. Ms. Neilson called and said she will be here at six-thirty. The drive takes about an hour. She wants to be there early enough to unpack and get a good night's sleep. It is very important tournament for this part of the state."

While upstairs packing, Jayden comes into the room. She is quickly in my arms. Still dressed in her robe, her body feels so soft and willing. My sexual urge becomes apparent to Jayden and me. Lowering my zipper, she fondles my length.

"I am going to miss this tonight. I can't believe we did it. I loved it! I can't wait to tell Brigitte. I know she will be jealous. Do you want to do it to her?"

Just the thought of seeing Brigitte's naked, chocolate body gets me hard; fucking her will be a privilege. Jayden drops her robe and is on her knees. Her mouth swallows my shaft. My reaction is automatic as my hips start mouth fucking.

"Andy, can you put it in me again? I won't feel you inside of me till Monday. That is a long time."

"What about Mom?"

"Please, Andy, I want to feel you in me again."

My lower head takes over for common senses. With Jayden on her back on my bed, I mount her. After three times last night, my cock easily slips into her stretched pussy. Hell, it feels so good! The best thing that happens is when Jayden actually stiffens and cums; the first time with my cock in her. She looks surprised.

"Andy, you made me cum. Wow, does that feel good! I wish you weren't going tonight."

"Me too."

The balance of the day is a whirlwind of activity. It takes some doing but all of the lawn jobs are completed by four. I smell like an old armpit. One memorable moment today was with Janice Morgan, the oldest daughter of Ralph Morgan, when she offered me a cold soft drink after completing their lawn. Since it was my last job for the day, I accepted. In the kitchen, she shocks me by actually looking at me in a very sexual manner causing my cock to get hard and tenting my shorts. Embarrassed, she only smiles at me, actually comes close, and rubs me. She is a senior in high school and a captain of the cheerleading team. I have seen her in her pool in a bathing suit many times. I am totally confused.

"One of these times, we will have to do something about that, Andy. That is quite the pistol you are packing!"

Fortunately, my hardon disappears by the time I get home. Mom has a sandwich ready for me. She screws up her face when she gets a whiff of me.

"Get upstairs and shower. Bring your clothes down and I will wash them. You really stink."

By six I have showered, eaten and did the last of my packing. Jayden comes into my room just as I am about to go downstairs.

"Think of me, Andy. I will be thinking of you tonight. Here is something of mine for you. I wish you weren't going."

Jayden hands me a pair of her panties. I know they are one of her favorites. Before giving them to me, she rubs them on my nose. It is a scent I have grown to love.

"Don't forget what they cover."

"I won't."

"Brigitte is really jealous that I have had sex before she did. She wants to come over and watch."

"Tell her maybe next week, if mom and dad go out. But tell her she has to get undressed if she is going to watch."

"Okay."

At six-twenty five, Heather pulls into our driveway. Even after having Jayden this morning, my cock swells at the sight of Heather. She is wearing powder blue golfing shorts and a white blouse with three buttons undone. Mom is talking to her, as the trunk seems to open all by itself. After dropping my suitcase in the trunk, the lid seems to have a mind of its own and slowly closes. Looking up, I watch Jayden coming down the walk. Then I realize she is walking different. Her feet seem to be spread, like a duck, as she approaches. It must be because of our fucking. Hell, I hope mom doesn't notice and question her!

After the goodbyes, and a kiss from mom, Heather backs out of the driveway. Jayden looks at me and then blows me a kiss mouthing 'I love you.' I blow her a kiss back, which is noticed by Heather.

"You and your sister are close?"

"Yes, we are. She is my best friend."

"Andy, I've missed you. You took me back to a time when my life was so good."

"Heather, it was good for me too. I never knew anything could feel like that."

"Are you ready for this weekend?"

Heather reaches over and pats my crotch. My cock has been at attention since we left. From this angle, the view of Heathers breasts, down her open blouse, is more inspiration then I will ever need. She surprises me by lowering my zipper.

"Get it out for me, Andy, please. I want to feel it."

For the balance of the trip, Heather has my cock in her hand squeezing softly and occasionally pumping. A couple of times my hand is at her pussy, when we are stopped. Her panties are damp and my fingers smell good when I bring to my nose. Heather smiles as she was watching me.

"Andy, we will have to sleep in the same room. The hotels are overbooked, due to the tournament. I hope you don't mind."

"Don't mind at all."

"I didn't think you would mind. A few of my girlfriends are doing the same thing with their caddies. And no, I don't know if they are doing things as well."

Arriving at the hotel, we find total confusion. It seems like every golfer has arrived at the same time. Once parked, it takes nearly an hour to check in due to the horde of people. Finally, we get to our room and find that our twin bedroom turns out to be a single queen sized bed. Sleeping with Heather for three nights will be very interesting, as well as educational. She promises to show me other things we can do.

Everything that I learn will be perfected with Jayden. However, that will have to wait till next week. Confusion reigns everywhere in the hotel. Trying to secure a luggage cart is impossible. It takes me three trips to carry up Heather's luggage. She must have brought her complete wardrobe and her rock collection. Struggling through the door with the last load, she rushes to help me.

"I am sorry, Andy. I never expected it would be this bad. I bring the same amount of luggage to all my tournaments."

Heather has showered. The view of her lush body takes away all the pain of hauling her luggage. Smiling, she approaches me, pulls me into her arms and kisses me; her scent, a mixture of shampoo and body wash, has me tingling all over. My tent is at the right height and is pushing into her pussy.

"Andy, why don't you shower before we go looking for some place to eat; after seeing all the people downstairs, I imagine every restaurant in the hotel will be full. I hope it is not like this every day."

The bathroom is relatively large, considering the room has only one bed. Heather's panties are draped over the side of the tub. She has to have left them there on purpose. Bringing them to my nose gives me a scent that really gives me a gut busting hardon. After my shower, I brush my teeth and comb my hair. Opening the door, to make sure no one else has come into the room, I walk to Heather. My cock bobs up and down. Heather licks her lips and lies back on the bed with her robe open, giving me a view of heaven and her lush titties. In her arms, we hug with my hands roaming over all of her body. Her pussy is bare and smooth, just the tuft of hair above her large clitoris. Her clit is extended, waiting for attention. Between her legs, my mouth quickly finds its goal. Sucking Heather's clit is like sucking the end of my little finger; it is so large! Tremor after tremor runs through her body as she experiences multiple climaxes. My fingers explore her pussy; I get really confident and finger her asshole. Heather surprises me by pushing against my finger. Applying pressure, it is quickly engulfed, deep in her anal opening. I can feel it contract every time she climaxes.

"Andy, it has been a long time since someone did that to me. I am going to show you how much I enjoy what you are doing later. Come up beside me."

Leaving her clit and sopping wet pussy, I move up the bed. Kissing, we move so our bodies so that contacts are at a maximum. Heather slides her hand down my stomach and grasps my tool.

"Oh, Andy, I am glad we met last week; if we hadn't, I would never have the opportunity to enjoy this."

She gives my cock a squeeze. Breaking our kiss, she moves down and swallows me. She has taken my full cock in her mouth. I can feel her throat working on my shaft. It feels so good. Will Jayden be able to swallow all of me? I hope so! Then, without realizing it, I start cumming, string after string pumps into Heather's throat. It isn't what I wanted to do. I wanted to fuck her again.

When my cock slips out of her mouth, it leaves a small gob of cum on her lip. Her long tongue finds it and she flicks it into her mouth and swallows. Leaning over we kiss, sharing the taste of cum.

"I am sorry, Heather."

"Don't be. You taste refreshing! You know, girls like sucking guys as much as guys like tasting girls; besides, you taste good! Does your sister do this for you?"

"What do you mean?"

"I mean, you told me your sister is your best friend. When she looks at you, she telegraphs that she is in love with her big brother. Am I right?"

"Yes, we do each other. You won't tell anyone, will you?"

"Of course not; but, I am jealous of all the time she can spend with you. I wish I could take you home with me!"

"Unfortunately, we have to get dressed and have something to eat. When we are done, we can return and go to bed early."

There is a large smirk on her face when she says that. She enjoys sex as much as I do! My cock is already reacting; I can feel it trying to grow again. Remembering all of the times I masturbated, had I known Heather, and been kind to Jayden, maybe I could have been doing this for a long time instead of flushing it down the toilet.

Once we have left the room, it seems to take forever to ride the elevator to the lobby. It's still a zoo, as the late arrivals are streaming in. A bellhop tells me about a small family restaurant, that is off the beaten path, that has good food and the odds are in our favor that it isn't full. Giving Heather the directions, we leave in search of it. The directions are exact. There is plenty of parking in the lot; a good sign that it isn't going to be crowded.

Heather turns every male's head in the restaurant. Her sheer, see through blouse doesn't hide much. The blouse is a pale rose and her lacy uplift bra a bit darker. The effect has all eyes on her. There are many questioning looks as I pull out Heather's chair to assist her. Her makeup is flawless, her eyes have a sparkle of mischief, and I am her escort. After the meal, we enjoy a tasty dessert.

"I think your dessert was much better than this one, Andy."

My tool has totally recovered from our earlier bout in bed. I am looking forward to what lays ahead when we return to the hotel. During dinner, Heather's foot kept rubbing me. Twice she managed to rub my hardon, nearly causing an accident. The first time my mouth was full and it took me by surprise.

"I am ready to leave, Andy. Are you?"

"I am finished. Thank you for dinner."

"Here is my credit card. You pay the bill like I am your date. Let's give all these people something to talk about when they go home tonight."

All eyes are on Heather as she sways her way to the cashier's desk. She waits patiently as I pay. She makes a point of thanking me for dinner and saying she is looking forward to the evening with me. It is a bit embarrassing for me, but I go through the charade with her. Taking her arm, I lead her from the restaurant with all eyes drilling into our back.

"That was nice, Andy. You are an excellent host. Now, let's get back to the hotel. I am tired and tomorrow, is a big day."

The hotel situation hasn't improved. It is fortunate that we checked in early. From the conversations in the lobby, it appears the hotel overbooked and the late arrivals are in dire straits. Once on our floor, and in our room, the click of the door locking relieves the pressure for both of us. Heather goes to the bathroom. Undressed, I watch television waiting for Heather to reappear. The door opening causes me to look. Heather is wearing a full-length sheer negligee. The soft rosy color sets off her make-up and lip-gloss. Her beautiful body is on full display. She seems to float towards me.

"Heather that is a very sexy gown you are wearing."

"Thanks, Andy. I haven't been able to put on a show like this for years. I love wearing clothes like these when someone can appreciate them."

She whirls around and the gown flows upward. The effect is mesmerizing. Her scent fills the room. When she leans over to kiss me, her breasts hang down from her body. Grabbing my hand, she pulls me towards the bed. Looking at me, eye to eye, she pulls a tie and the gown floats down her body to the floor. Once in bed, and the light dim, she is in my arms cuddling and kissing. Our bodies are like one. Rolling onto her back, she pulls me with her.

"Just fuck me, Andy. I want to feel you in me and then we have to get some sleep. Thank you for being here with me."