Date: Mon, 15 Aug 2005 02:47:45 EDT
From: JstaFlyOnTheWall@aol.com
Subject: HOW LUCKY CAN YOU GET? Chapter 2

DISCLAIMER: The events and characters depicted in this story are purely
fictional. Any resemblence to real people or places is a coincidence and
should just be forgotten about...  no harm is intended to anyone! This
story containes situations of a sexual nature between cross-generational
males. If this is offensive to you, you probably shouldn't be at this site!
If it is illegal for you to read this in your locale, you probably need to
stop reading at this moment.

AUTHOR'S NOTE: Before I get started on chapter two, I would like to thank
all of you for the emails! How could I not continue my story after all that
encouragement! Thank you!! (Special note to Ryan... I had already started
this chapter when I got your email. I think you will not only like what you
read, you just might be VERY surprised!) Keep those emails coming! This
story may never end!  -Geoff


HOW LUCKY CAN YOU GET?
by Geoffrey Chassen
Copyright 2005. ALL RIGHTS RESERVED.


Chapter Two: Gabriel's New Life


Two days ago I was sitting in my room after soccer practice "Googling" my
way through the internet. Papa was still working and Monica, my little
sister, was at her friend's house. I loved having these times all to
myself. It was the only time I could go to all those "secret" sites... the
sites that made my stomach do flip-flops and gave my cock a mind of its
own. These were the websites where boys like me could be themselves. Look
at other boys... or men!

I'm sixteen years old and a sophomore at Central High School. I'm a great
student and all the guys like hanging out with me and it seems like I'm
always surrounded by girls. My friend Danny tells me that the girls just
hang around hoping that someday one of them will end up in bed with me. I
don't see it though... maybe 'cause I'm just not looking in that direction!

I typed "gay male stories" into my search bar and started looking around. I
found this site called "Nifty" and soon found some of the hottest stories I
had ever seen! I found some stories that had chapters and chapters, picked
one and started reading. I was amazed! I found that all these feelings I
had been having for the last year or two weren't so strange! While the head
on my shoulders felt this enormous wave of relief, the head on my cock was
fighting for release.

I was reading stories about boys my age (or younger) and older men who
loved them. It was so hot! My fantasy was coming true. It was so natural
and beautiful, tears were coming to my eyes. As if that wasn't enough, I
was learning a whole lot about what to do, how to do it and where to do it
so that it felt good. It didn't take long for me to jump up, lock the door
to my room (just in case Monica came home early)and peeled off my clothes.

I think I have a pretty good body. I go to the workout room after school or
after soccer practice every day of the week...have been for over a year
now. When I started getting a six-pack, it only made me want to work harder
and look better. I stood in front of the mirror and admired the results of
my work. If only I could find a man... a REAL man... who would like it
enough to do all those things I'd been reading about! With that thought, my
hard cock jumped and pre-cum dripped out onto the floor.

I went back to the computer and read some more. One of the stories talked
about sticking a finger in the boy's butt and finding his "button." I
wondered if I had one of those. Well, there was only one way to find out! I
scooted down in my chair and spread my legs. I started rubbing my little
hole. WOW! I couldn't believe the feelings that shot through my body! I
then started to push my finger in but had to stop. It kinda hurt so I
pulled it back out and went back to that awesome feeling I got from rubbing
the outside.

As I was reading, I got an idea. I took some of that pre-cum that was
flowing out of my cock and covered my finger. I went back to rubbing and
almost shot a load right then and there! All I could think about was a hot
man doing that to me! Maybe with his tongue like I was reading now. I tried
pushing my finger in again. This time it went in a lot easier and before
long i was exploring deep inside myself. I had to find that button! Where
was it? Maybe I don't have.... AHHHHHHHHHGH.... FUCK! My cock started
jerking and shooting cum all of my face, my hair, my neck... Damn! I didn't
know you could shoot without stroking your cock! One thing I DID know... I
had a button! I kept rubbing it and my cock kept shooting.

After things relaxed a little, I cleaned up and still in some kind of daze,
I hopped into the shower. The hot water was pouring over me and just closed
my eyes. Imagining a hot man was in the shower with me, I was rubbing my
hand through my hair... imagining my fantasy lover's hands. I rubbed my
hard pecs and rubbed my fingers over my hard nipples... imagining my HIS
fingers. My still hard cock was throbbing again as I soaped it up and
imagined his mouth giving me my first blow job. I leaned against the wall
and imagined him moving behind me, holding me, kissing me, telling me that
he loved me as he pushed his powerful cock into my cherry ass. I was slowly
stroking my cock and pushed two fingers into my hole. I couldn't believe
how good it felt! I guess it means that when the time comes, I'm going to
be a bottom! In about twenty seconds, I was cumming all over the shower
wall, moaning and telling my imaginary lover that I loved his cock inside
me.

"Gabe! I'm home!"

Shit! Monica was back from her friends house. "I'll be down in a second
baby girl! I'm taking a shower," I yelled to her in as normal a voice I
could muster up. I finished my shower, stepped out and dried off and looked
at my body in the mirror. I looked different.  My cheeks were
burning... like they were glowing. I'd looked at my body a lot of times,
but this time all I saw was a man... not a boy... a man who was ready to
discover and take on a whole new life!

"Gabe! Papa's on the phone! He wants to talk to you!"

Shit again! I didn't even hear it ring. Monica finally had snapped me out
of my new dream world, so I dried off and got dressed in my favorite jeans
and a t-shirt. When I got downstairs, I grabbed the phone from the
table. Turns out Papa was running late on a job and needed me to make sure
we had dinner and did our homework. He would be home in couple of hours.

Monica decided we were going to have hamburgers and cheesy-mac! She wanted
to make the cheesy-mac herself while I made up the hamburger patties and
put them in the skillet. She loved the idea of cooking but Papa would only
let her use the microwave for now. This is why we seem to have cheesy-mac
three or four times a week.

Monica set the kitchen table while I made a salad. I had to have SOMETHING
healthy! When everything was done, we sat down and had dinner. Monica
decided that these were the best hamburgers in the whole world and I just
smiled at her. I truly loved my little sister. Ever since Mommy died, I've
been the one to take care of her.

I started thinking back to three years ago. It was so hard on the whole
family when Mommy died. It happened so fast. One day she came home from the
doctor all crying and everything. She and Papa talked for a while and then
they called for me and baby sister to come in. Papa was crying too. I knew
something terrible was happening since none of us had ever seen that
before. They told us that Mommy's doctor found cancer in her breast. Papa
and Mommy just sat there, softly crying while they told us that it was
bad... real bad. Mommy wasn't going to with us for long.

Every day after that talk, Mommy would ask me to help her cook dinner. She
taught me how make food taste good. She taught me how to wash clothes and
iron them. She showed me what to do to clean the house.

In just a few weeks, Mommy had to stay in the living room. She was too
tired to get up. The docter sent a Hospice nurse to come by and take care
of her two or three times a day. My job was to keep Monica as happy as
possible and make sure everyone got a good hot meal. Mommy was so nice to
me when I would try to cook her favorite food. She would try to eat as much
as she could, but after a while it was too hard for her to eat. She always
told me how good the food tasted... how good it smelled. She always made me
so happy! Until that one night. That sad night when I heard Papa from the
bedroom. He just cry out, "Noooooo!"

It would just be the three of us after that. For two weeks it was like I
became in charge of the house. I took care of Papa and Monica, remembering
all the things Mommy had taught me. I would hear her tell me how proud she
was of me when I would finish cooking dinner, or doing the laundry or
cleaning the house. It's funny, after three years I still hear her voice in
the back of my mind. It doesn't make me sad though, it makes me proud that
I can still make her happy with me.

A couple of weeks after the funeral, Papa called me into the living room
after he had tucked Monica into bed. "Gabriel, you have been such a good
boy to me and your baby sister. I'm so proud of you. You made the last
couple of months so much easier on all of us, including Mommy."

For the first time since Mommy told us she was sick, I felt like I didn't
have to be strong. For the first time in weeks, I started to cry in front
of Papa. He just held me and cried with me. It felt so good to let all of
that stuff go. After a few minutes, Papa dried his eyes. "Gabriel, I need
to get back to taking care of my family. I'll still need your help with
Monica, but I can't let you become a substitute for Mommy."

I just looked up at him while he explained that my Aunt Lucia was going to
come over a few times a week and cook dinner for us and that she would also
help with the laundry and cleaning. He wanted me to start learning how to
do the kind of things he did... a "man's" work. I couldn't believe it! I
was going to start helping Papa with his gardening business! Papa was so
happy that I was excited. But I made sure he knew that I loved doing the
things that Mommy taught me as well, and that I still wanted to that
too. Papa just beamed. It was the first time I had seen him smile in such a
long time. That was the moment I knew we were going to be alright.

Monica finished her supper with a "Thanks for supper Gabe! Did you like my
cheesy-mac?"

"Well baby sister, it was... cheesylicious!"

"Gabe, you're such a dork!" I laughed as she came over to my chair and gave
me hug. We picked up our dishes and loaded up the dishwasher. I sent her
off to her room to do her homework and I went to mine to finish mine.

When I got to my room, I sat down at my desk and moved the mouse on my
computer. The story that changed my life was still on the screen. I read
some more and the more I read, the more I just knew that it was time for me
to find a man to be my lover. I had no idea how it was going to happen, or
when, but the stories I had been reading all afternoon sure gave me enough
confidence and ideas of HOW it was going to happen!

Before I turned off my computer, I got an instant message from Danny.

DANMAN17: hey bro! how's it hangin?  ANGELG: danny! all's good here!
DANMAN17: did u finish reading your english?  ANGELG: dude, u must be
psycho! i mean psychic! i was just grabbing the book. besides, i have til
monday. no school tomorrow! gotta luv teacher workdays!  DANMAN17: hell
yeah!  DANMAN17: hey, mom's letting me have the car tommorow nite.  ANGELG:
awesome!  DANMAN17: she said u can cum over for supper and then we can go
to the mall. hang out with eric and jon. maybe see a movie?  ANGELG: hold a
sec... let me ask papa. brb

I ran downstairs and asked Papa if I could hang out with Danny for supper
and go to the mall. He was cool with it since Aunt Lucia was fixing dinner
tomorrow. "But I want you home at 10:30!"

"Papa! It's Friday! We don't have a soccer match on Saturday! Couldn't I
stay longer?"

After some short but intensive negotiations, I got the curfew changed to
11:30. "Thanks Papa! You're the best!" After a hug and kiss on the cheek, I
raced back upstairs to my computer.

ANGELG: dude! it's a date!  DANMAN17: u sick puppy! it's hanging out, not a
date! lol ANGELG: lol DANMAN17: hey I gotta finish reading this play so I
can answer more questions about it than u on monday!  ANGELG: u wish!
everyone know i'm the smartest. and the girls think i'm the hottest! lol
DANMAN17: yeah right. i've already had five of the girls in our class. how
many have u had?  ANGELG: i'll get laid when i'm good and ready. enjoy the
glory while u can dude! cause once he get's started, nothing's gonna stop
the gabe!  DANMAN17: whatever dude!  DANMAN17: hey, i gotta run. getting
late.  ANGELG: no prob. cya tomorrow!  DANMAN17: ttyl ANGELG: later dude!

I signed off, powered down and plopped down on my bed with "Pygmalian." I
loved reading plays. I could picture them in my mind as I read and this one
was one of the best yet. Of course there's this older dude teaching a young
girl all about life. That's what I wanted... a hot older man to teach me
all about life, love and of course, sex! I just hoped I would find
him... soon!

It was about 9:00 the next morning when I woke up to Aunt Lucia coming into
the house. "Buenos dias mi bambinos! Lucia esta aqui!" I threw on my
bathrobe to cover up my morning wood and went downstairs. After some hugs,
kisses and a little breakfast, we all went our seperate ways and Aunt Lucia
started in on some housework. About ten minutes later Papa called and said
he needed me to go over to the Jacobson house and touch up the lawn. Damn!
He forgot I had plans! Papa knew I wasn't happy about going over to there
but he promised me the entire fifty bucks and said I could just take some
clean clothes over there. I could clean up and change in the pool house if
it was okay with Mr. Jacobson. I agreed, put some clothes in my backpack,
hopped on my bike and headed over to the Jacobson's. I'd helped Papa with
that job many times so I knew what I needed to do. At least it was on the
way to Danny's house.

About 20 minutes later, I was parking my bike outside the Jacobson's and
rang the doorbell. Some guy I had never seen before answered the door. I
wanted to make Papa proud of me so put on the best professional air a
sixteen year old boy could muster. The dude was definitely cute... even
kinda hot. But just kept staring at me and smiling! I watched his eyes move
down my body and I was starting to spring some major wood and I couldn't
let him see that!

"Um, Mr. Jacobson? Hello! Mr. Jacobson?"

Thank God he snapped out of his trance before he could see my boner! I
would have died. But he was way cool. He said I could clean up and change
at the house when I finished. I handed him my backpack and when he touched
my hand I thought my body would explode! He was staring at my hand and I
was just looking into the most beautiful, warm eyes I had ever seen. It
seemed like five minutes went by before I heard him say, "Um, hello?
Gabriel?"

"Oh, I'm sorry Mr. Jacobson," I replied, snapping out of my daydream. "I
was just thinking about... um... my plans for the night!" Damn! I almost
told him I was thinking about looking into those eyes while he fucked me! I
gotta be careful! I can't mess up things with one of Papa's most loyal
customers!

He told me to call him Andrew and all I could come up with was "nice name!"
God, Monica is right! I'm such a dork. I just smiled and went out back
where I knew they kept an extra lawn mower. I had to get out of there
before I made a total ass of myself!

While I was walking to the back, I looked over the lawn and saw that Papa
cut it straight to the property line the last time. That meant I had to do
diagonal cuts this time. Shit! That's twice as much work! I couldn't even
think about doing it the wrong way. Papa was real anal about changing the
direction of the cuts each time so the grass would grow thicker. Well,
that's what made him so good and why people like the Jacobson's paid him a
lot of money to do the job right.

Actually, I was kinda glad to be cutting on the diagonal this time. It
meant I got to face the house more times and each time I did that I could
see Andrew sitting in the kitchen reading the paper and drinking his
coffee. I had started at the back of the property and the closer I got to
the kitchen window, the hotter he was looking! I started thinking about
those stories on the internet. Between the stories and the hot man in the
kitchen, It wasn't long before my underwear was wrapped around 7" of hard
virgin cock! Was it him? Is Andrew the man I've been dreaming about?

It wasn't long before the heat was getting to me and I took off my
t-shirt. I tucked it in the back of my shorts and worked my way closer to
the house. Once, I caught his eye and waved to him with some dorky grin on
my face. He looked out and waved back, not with a dorky grin... but with
the sexiest smile I had ever seen! Andrew was making me hotter than the
heat from the sun. I grabbed my t-shirt and wiped the sweat from my
face. He was still staring and smiling! That was when I decided to take
everything I had learned from the internet and see if he really WAS my
dream man! I slowed down a bit and started wiping the rest of my body,
showing off my muscles as sexily as a kid could do! I hope he didn't think
I was an ass or anything!

Andrew kept looking at me. He was smiling even bigger now so I decided to
go for it. I pulled out the waistband of my shorts and stuck my t-shirt
down over my hard cock. I don't know what he thought of that, but I had to
adjust myself. Hell, my cock was bent the wrong way and was starting to
hurt. All of a sudden, he stood up, grabbed something and started coming
out to the back yard. Fuck! I blew it! He was going to throw me off his
property for perving in his backyard!

I snapped out of my fantasy real fast and put on my most grown-up and
professional manners.

"Hi Mr. Jaco... I mean Andrew! Man, it's hot today!" I couldn't think of
anything else to say, I was so scared! Then I noticed that he had grabbed
some beers! Way cool! Danny and I have grabbed some of his dad's beer a few
times and got drunk. I liked beer!

He offered me one but I was still in my professional mode so I asked for a
glass of water instead. But I made sure he knew I would have some beer when
I finished. He seemed to like that idea even more than I did! He turned
around and walked back to the patio doors. My cock was throbbing with
excitement. As soon as he had turned his back to me, I figured it was safe
to reach down into my shorts and gave my lonely friend a few strokes. "Hey
bud," I said to my meat, "I think today's the day! You're finally gonna get
sucked if I'm thinking what you're thinking!" Suddenly I felt like a dork
again. Do normal people talk to their cocks? Geez!

I went back to the gardening shed and got the blower out. When I was
getting back to the house, Andrew was coming out with a glass of
water. Holy crap! He had a huge boner and there was a big wet spot on the
front of his pants! I hope he didn't see me looking down there. Well, not
yet anyways!

Damn, that water sure tasted good! While I was gulping it down, my mind
flashed back to some of the hot pics I had seen on the internet a few
nights ago. Without even thinking I pulled the cup away from my lips, threw
my head back and poured the water down my face and chest. Fuck!! That was
some COLD water! It made my nipples stick out a mile. When I had emptied
the cup, Andrew was just staring at my cock. Thank God the cold water had
tamed it a bit. Andrew didn't seem to mind though. That spot on his pants
seemed to be a little bigger than it was a few minutes ago! Yes! It was
working!

Andrew offered to help me with the yardwork by handling the blower and
cleaning up the clippings. I tried (in my most professional way of course)
to turn him down, but he insisted. So I fired up the mower again and worked
my way to the front of the house. Papa would have just shit bricks if he
had seen how fast I was moving. Hell, I didn't want to waste any time! I
was gonna have my first sex in just a few minutes! I just knew it! When
Andrew made his way out to the front, I was almost done. I didn't even look
at him. I was in a hurry!

After putting up the mower, I raced back to the front. Andrew had just
finished his part so we went inside. He was really nice with complimenting
me on my work. He even said it looked better than when Papa did it! I was
so proud! He made me promise I not to tell Papa he said that. All I could
say was something stupid like, "Hey, what happens here, what's said
here... stays here. I'm not telling Papa a thing!" Super dork!

We went back into the house with the air conditioning that felt like
heaven. We decided to cool off first with the beer when he asked me if I
was old enough to drink it. Wow! Did he think I was old enough? Did he
think I was 21? I couldn't lie to him, I was a terrible liar anyway and
never got away with it. So I told him I was sixteen but I still drank beer
all the time. Okay, so I lied a little! I was leaning up against the
kitchen counter when I thought about what I had just said. All I could do
was smile at him and he finally gave in. So we just sat down at the kitchen
table and we started just shooting the breeze. He was real easy to talk to!
We talked about my family a bit and I told him about Mommy dying and all. I
was getting a little down though. Not from talking about Mommy, but I just
had a feeling that he didn't want to have sex with me anymore. I guess he's
not into boys. Oh well, I'll just do what I've always done and stroke off
in the shower. He'd never know about it. Hell, he'd never know
anything... and neither would I!

Just as I was starting to get totally depressed, he asked me what I wanted
to do for my shower. He gave me choice, but one of those choices was the
master shower. Hell, it had all these showerheads in it... all over! I'd
never heard of anything like that!

"Multiple shower heads? One isn't enough?" Damn, if Andrew didn't think I
was a dork yet, he sure did now! All I could do was come up with this
stupid dork laugh and grin. But I chose the big shower.

We finally made our way into the master bedroom and I almost shit in my
shorts! It was like a palace! Just the bedroom was almost the same size as
our entire downstairs! As soon as we got into the bathroom, he showed me
where everything was, but I started to panic. I had no idea how to turn the
different showerheads on. What if I flooded the bathroom? He offered to get
things ready for me. As soon as he turned around and leaned into the
shower, I saw his ass... what a hot ass! Everything went into slow motion
for me right then. All at the same time, I started thinking about those
stories, all the pictures and video clips, my cock sprang up harder than it
had ever been. Just as I had stepped out of my clothes I heard my fantasy
man ask me how hot I wanted it. In a voice I had never heard come out of me
before, like it had come from deep inside me... from someplace that I had
never know existed, I answered him with, "As hot as we can make it!"

Before I could think or say anything else, I moved toward him... toward my
dream. I pushed him up against the shower wall with all of his clothes
still on him and gave Andrew my first kiss. I had to feel it! I reached
down and felt the biggest, most amazing cock. It felt just like the ones I
had seen on the internet! It was at least an inch bigger than mine, maybe
more! It was thick and throbbing.

He tried to stop me by talking about him going to jail if we were ever
found out. I just told him I knew he wanted it as much as I did. And
besides... I was was making the first move here. I had been seducing him
all morning! I had to think fast and act even faster before he could talk
himself out of it. So I did what any sixteen year old boy with a mission
could do... I grabbed the waistbands of his pants and underwear and pulled
them now. Before I knew it, I had a cock... a MAN'S cock in my mouth!

It was amazing! Andrew was moaning so I knew I was doing it right! But all
of a sudden, I couldn't remember anything from the stories! I was
panicking. Tears started to roll out of my eyes. It took everything I had
to stay under the water so he couldn't see me crying. The next thing I
knew, his strong arms were pulling me up to him.

"Nooooo!" I cried out. My lips were trembling.

He pulled me into a kiss again but I couldn't stop shaking. The next thing
I knew he pulled me away from him. "What's wrong baby? Why is my angel
crying?"

"Andrew," I said while trying to muffle my sobs, "I don't know what to
do. I've never done anything like this before! I know more than anything
that this is what I want to do. I'm just lost!"

"Wh-wh-what?" Andrew just looked into my eyes. "You're a virgin?"

"Totally. Please don't hate me? Please teach me! Please let it be like the
play!" I couldn't stop sobbing as I spoke.

"The play? What play?" Andrew looked confused.

"Pygmalian. I want you to be like the professor and teach me
everything. Show me how to make love. Show me how to live!" I totally broke
down in his arms.

With the water pouring over us from all over the place, Andrew pulled me
into his arms. "Are you sure this is what you want Gabriel? Have you really
thought about this?"

"It's all I've thought about for months." I felt so safe in his arms. My
crying had nearly stopped and I just spoke into his chest. "I knew I wanted
my first time to be with a man who was older than me. Someone who knew what
to do. Someone who really cared! I just never thought I would actually find
my dream coming true so soon!"

"Really? I'm making your dream come true?"

"No Andrew... you ARE my dream come true!"

With that he pulled off his shirt and stepped out of his soaked pants that
were bunched around his ankles. For the first time in my young life, I felt
a man's hot, naked body pressed up against mine. I felt a man's hands
running through my hair. I felt a man's fingers playing with my hard
nipples. I felt a man's cock rubbing up against mine. He kissed me with
more passion that I had ever dreamed about. Just as he squeezed lightly on
my nipple, everything came to a boiling point. With all the excitement of
the morning... the teasing, the seducing, tasting my first cock... I felt
my body tense up like it had never had before. As if it had a mind of its
own, my cock just exploded. I could feel ropes of cum hit my neck. I felt
it on Andrews amazing chest. I had covered my dream man with my cum. I was
now in my dream of all dreams... and I never wanted to wake up.


***************

Well, there's the second chapter! I hope it wasn't too long. I wanted to
get some background information on Gabriel taken care of. If you'd like
another chapter, drop me a note at JstaFlyOnTheWall@aol.com. Thanks for
reading AND the amazing feedback!

Geoff