Date: Sun, 30 Dec 2007 10:22:25 -0800 (PST)
From: R Ranger <bn2rumpranger (at) yahoo (dot) com>
Subject: Latchkey Kid Turns a Profit

Warning! If you are not of legal age to read stories that contain erotic
subject matter or you are offended by erotic subject matter contained
herein do not read any further. All rights to this story are reserved and
retained by the author. This story is a work of fiction protected under
applicable copyright laws and may not be reproduced without the express
written permission of the author.

Comments and critics on the story are welcome and may be directed to
E-mail: bn2rumpranger "at" yahoo "dot" com   Subject line: Latchkey
Kid Turns a Profit

                          Latchkey Kid Turns a Profit

                               By Randall Rumper


"Oh Yeah! Fuck me Jimmy," I growled as I rode Jimmy Connor's hard hot
cock that was buried deep inside me.

Five other boys from sixteen to twenty sat around the room watching Jimmy
fuck me in the ass as they waited their turn. Before I began fucking
Jimmy there had been an oral orgy among all of us on the big hotel room
bed. My sister and Jimmy's older brother moved around the room directing
the action and video taping the event from two different view points.
They weren't making pornography to sell to the open public; however, the
video tapes would be edited, and for a fee each of the participants would
receive a copy. After the oral orgy concluded all six had drawn randomly
to determine the order in which the boys would take turns fucking me.

To my delight Jimmy won the draw. I promptly mounted my best friend and
been impaled on his throbbing hard member for the past few minutes
awaiting the stroke of midnight -- the ball was about to fall in Time
Square. As we all awaited the New Year tradition I rode Jimmy's hard
cock like a professional cowboy, riding a bucking bronco at a rodeo.
Rodeo riders want to stay on their animal as long as possible to win. The
same is true for me riding a hard dick. I want to make the fuck last and
didn't want the boy beneath me to climax prematurely. Early on I had
developed a technique whereby I could control matters, delaying my
partner's premature ejaculation as well as mine.

I just hated it when a guy would cum as soon as he was inside me, or
before. I preferred the man on top position whether I was the fucker or
fuckee. The position gave me greater control of the situation; besides, I
could watch the facial expression on my partners face. Jimmy smiled up at
me from his position lying on his back on the big bed, begging me to ride
his rigid rod harder and faster while the others cheered and coaxed us
towards climax.

Jimmy's brother and my sister jockeyed for position trying to capture
all the intimate details of the action with there hand held video
cameras. If I had my way and worked Jimmy just right I wasn't about to
let him cum too quickly. I slowed and began riding him in at a more
leisurely fashion once again. As the countdown to midnight neared I
raised my buttock up slowly to a point where the base of Jimmy's
cockhead was resting inside against the inner ring of my anus. As the
Waterford Crystal Ball began its slow descent I would ease down Jimmy's
six inch steel pole at the same rate mimicking the ball dropping until my
bare buttock came to rest on Jimmy's furry pubic bone.

Once the midnight ceremony was concluded I would begin to rise and fall
on Jimmy's hard shaft increasing speed until he exploded into the condom
he was wearing, filling it with his spunk. After I was done doing Jimmy I
would take on the other hand picked young studs again and again for the
next few hours, ringing in the New Year. If Jimmy could hold off and not
ejaculate prematurely he would be my first fuck for 2006.

The five guys lounging on the king bed waiting their turn to fuck me were
self-proclaimed straight boys who were curious. They were young men who
led straight lifestyles dating girls, but were curious about same sex
sexual unions. All were students who were also athletes. They were
positively gorgeous looking male specimens. The two older guys were
alumni of our high school who were home on winter break from college. The
other three were current students at least juniors at our school. Jimmy,
Tommy and my sister had brought us all together in the hotel room for my
first of what would become an annual New Year's Eve fuck fest; a fuck
fest that would earn me well over six hundred dollars cash money, and
signal the beginning of my new career as a male prostitute.


                          Chapter 2: Earning Big Bucks


The New Year's Eve party 2006 was the beginning for me as a he-whore
earning money for my services. I was a fourteen year old high school
freshman in 2004 when I first realized my yearning for sex with other
boys, and started my apprenticeship towards becoming a male whore. During
those novice months prior to the New Year's Eve party I hadn't charged
for my services; however, I had come to recognize there was a niche for
my new vocation as I was becoming a much sought after male escort. After
New Year's Eve party I'd be a bona fide male whore. I had become
addicted to anal sex since that first time Jimmy took my cherry as a high
school freshman.

From that first time forward I was filled with an uncontrolled lust to be
fucked anytime anyplace. I didn't need the money, but I decided that I
wouldn't let my body be taken for nothing. When I first started engaging
in sex with other boys I was primarily into anal sex for the pure
pleasure of it. I soon discovered that the kids I fucked could well
afford a fee for my service. No, I was not a cheap slut by any means and
didn't fuck just anyone -- I had my rules of engagement.

There was one hard and fast rule: no contact with potential clients by
way of the Internet. I didn't get it on with just anyone. Second rule:
no older men. I considered anyone over twenty-five to be too old for me.
The third rule: clients had to be attractive and healthy in great shape
physically with a good-looking cock. I didn't engage in sex with ugly or
sickly guys who had fugly looking cocks. I didn't care for really hairy
guys either. When it came to clients I was a self-proclaimed cock
connoisseur.

No, I didn't fuck every guy who propositioned me, nor would I engage in
sex for less than one hundred dollars per session. Some men I charged
more, depending upon the time and the set up. Rule four: I wanted to look
my clients over before committing to any type sexual encounter, and
wanted a total confidentiality agreement. Jimmy and couple of my high
school friends were favorites who I did without charge in return for
sexual favors. Yes, I was what one might call a finicky fucker -- a cock
snob.

Over that first year of high school I developed from a naive freshman
into a full fledged male slut. I was pretty much a straightforward stud
who enjoyed fucking and sucking; no perverted shit for me, and no S&M. I
didn't let guys urinate or defecate on me or in me. I practiced clean
and safe sex. I'd quickly learned all the intricacies of anal
intercourse during that first year with the help of my sister and
friends; moreover, I very much enjoyed the sensual pleasures of getting
fucked. So, I decided to capitalize on my talent and the joy thereof.

I didn't let every guy that came along cornhole me. I was choosy about
who fucked me, especially when it came to size. I wasn't into pain when
it came to sex; therefore, I didn't care to take on guys that were
hugely hung. Those guys hung like a horse or mule. Although I preferred
to bottom, that is I was the one to get fucked, I would fuck the right
guy if there was interest. I broke into the business of engaging in male
to male sex accidentally when I started my freshman year in high school
after my move to the East Bay with the help of my sister and best friend.

My family which included my older sister moved to our new home in the
East Bay during the summer of 2004. My mother had taken a position with
University of California, Berkeley while my dad took a new position at a
teaching hospital in San Francisco. Prior to moving to Contra Costa
County my sister and I had led very sheltered lives. We had both been
smothered socially by the home schooling experience, but had excelled
academically since we began school. Our education grade point was well
above average, but our social lives had been pretty much stunted by our
parents control until we moved. Once we moved my sister and I began
attending the local high school where our social lives began to blossom
and flourish.

Our parents figured that because the area was very upscale there would be
little if no chance that we would be exposed to drugs and gangs, so we
were allowed to enroll at the local high school. Because of the closeness
in our ages Janie and I both started high school at the same time. Most
of the students at our high school were children of affluence. Their
parents held professional positions in San Francisco and surrounding
areas. Many were attorneys, bankers and doctors, while others worked in
computer related fields.

With the move to the East Bay my sister and I found our parents gone by
early morning everyday throughout the week to catch the BART to work and
many times they were late returning home. Both were totally wrapped up in
their new jobs which left Janie and me much time to develop outside
activities, including sexual exploration. That investigation included
canvassing the Internet. We accidentally stumbled across websites devoted
to pornography and sex during our leisure after school. We were what
society had dubbed as "Latchkey Kids."

Because my sister and I were born prematurely, there was only ten months
difference in ages between Janie and me; therefore, due to our ages and
the way our birthdays fell we both began high school the same year. To
look at us there was no chance mistaking that the two of us were brother
and sister. Growing up we had never been shy around each other.

Mother bathed us together until we were about six years of age, so we had
seen each other naked many times growing up. Growing up so close we
confided in each other about everything, especially our feelings as we
entered puberty and developed sexually. We had watched each other develop
physically from puberty into adolescence. On occasion we had masturbated
together during and after deep philosophical discussions about sex, but I
never touched her. We never had sex with each other.

I remember the first time I caught Janie masturbating. A few weeks after
we started at our new school we were in my room after school discussing
something we had read on a website called Jackinworld. As we conversed
about the subject I noticed one of Janie's hands buried inside her
cutoffs and the other up inside her blouse. Her hands were moving and she
was moaning softly. I asked her what she was doing and she replied that
she was sexually stimulating herself, playing with her happy maker. She
told me that she could get herself off simply by stimulating her clit. I
was curious, so I asked her about her clitoris and to show it to me as
I'd yet to be with a girl.

Janie stripped off her clothes as she explained about her love button.
She told me that the pleasure nub was a small elongated erectile organ
located at the anterior area of the vulva, homologous with the penis. The
most sensitive part of a woman's pussy. With her clothes off she spread
out on the loveseat across from me, splaying her legs wide displaying the
engorged little pink bud at the top of her pussy.

As she traced her fingers around the labia I moved closer to get a better
view of what she was doing. Later as I discussed sex with other young men
they had no idea what the clitoris was or where it was located. They
didn't know that when they gave a woman head that was the part of the
pussy that got the attention. A man's tongue or finger tip had to flick
the little nub perfectly in order to bring a female recipient to climax.

I soon discovered that most guys didn't know how to give head to another
guy or girls when they first began to evolve sexually. I would teach them
that the glans, frenulum and area of the circumcision scare were the most
sensitive for a guy's cock, and the clit was the area for female
stimulation. I also taught them that the area between the scrotal sac and
anus was a sensitive area, as well as the asshole itself. Nipples were
another area of sensitivity for some guys, not all. Many of my new found
sex partners were thankful for my instructions educating them as to the
areas of the human body's erogenous zones. I had discovered that there
were at least ten zones that would stimulate pleasure in both men and
women. Janie helped educate me in the female erogenous zones and I
schooled her on the male areas.


               Chapter 3: My Sister and I Learned from Each Other


Janie was a very desirous little vixen. I watched as my sister wet her
fingers and then traced them around her pink pussy lips. She rubbed and
flicked the swollen little red bud with one hand while the other played
with her erect nipple: two very sensitive areas of a women's body. As I
watched her manipulate her clit and nipple the more she moaned with
pleasure; meanwhile, I observed glistening fluid oozing from her pussy. I
asked what the substance was, whereby she replied that it was a natural
female lubricant, somewhat like my precum. She worked one finger inside
her vagina touching her "G" spot while she continued flicking her clit.
This technique brought louder moans and groans of pleasure from her;
eventually she began crying out, wailing -- ready to climax in a powerful
orgasm. Of course, my cock had grown hard by then and needed to breathe
watching the erotic show.

Janie noticed from the bulge in my cargos that my cock was in need of
attention, so she told me not to be shy to go ahead and whip it out. I
unleashed the beast and began flogging it. As I flogged my fully engorged
fuck stick Jamie looked upon my trouser snake with fascination. She
complimented me on its size and beauty. She was especially intrigued by
the beauty of my glans. She told me that I was bigger and had a better
looking cockhead than the few boys that she had seen boned up.

As I sat there on the floor beating my meat my ego had just been
bolstered. I looked upon my cock with newfound respect. Janie pulled her
finger from her pussy, holding it out for me to get a whiff. She told me
to lick her finger. I did; it didn't smell or taste that bad. About that
time I shot a load of spooge as she exploded in a body shaking wild
orgasm. We came down from our sexual highs and then she asked me if I'd
scored with a girl since we started school. I told her no, that I was
curious about sex with guys and what I really wanted was to have sex with
a guy. Of course, I reinforced quickly that I wasn't gay, I was just
curious.

My older sister smiled at me and said she might be able to help me out
with my curiosity. She told me that she'd been hanging out with a junior
named Tommy Connor. She said that Tommy had told her that his younger
brother who was a freshman might be bisexual, and that he was looking for
a male partner with whom to experiment. She asked me why I wanted to do
it with a guy. I told her that I'd seen guys on the Internet engaging in
sex oral and anal sex. I said that watching guys suck each other or take
it up the butt had definitely peaked my curiosity. I told her that I'd
been finger fucking myself for a while and that it felt totally awesome.
She asked me if I'd done anything with a guy yet. To which I replied no.

I asked my sister if she had fucked or sucked Tommy yet to which she
replied no, but she said that she wanted to do him soon. She told me that
she had masturbated him on couple of occasions, but that was it. I was
curious, so I questioned her about how big he was to which she replied
about seven maybe eight inches and fat. I was curious whether size played
a part in her decision no to perform oral sex on Tommy. She said that the
only thing that put her off about giving Tommy a blowjob was that he
wasn't circumcised.

Janie told me that she had discussed oral sex and uncut guys with her
girlfriends at school and discovered that most of them preferred not to
perform oral sex on the uncircumcised guys. She said it had to do with
the aroma and cleanliness of uncut guys. Janie also said that her and her
girl friends found cut guy's cocks much more pleasing to look at than
uncut guys, especially in the flaccid state. She told me that the girls
had unflattering nicknames for guys that were uncircumcised.

One of the things I'd discovered on the Internet was that circumcision
was a very controversial subject. Some guys were adamant about retaining
their foreskin, while others were upset that their parents didn't have
them cut at birth. I was convinced that circumcision would be a heated
debate that could probably go on for centuries to come. Janie warned me
again to be extremely careful. To make sure my partners were health and
clean, but most of all wear a condom if and when I engaged in anal sex
with a guy. She also suggested that I go online to research the subject.
I told her I'd found a couple of different websites that explained in
great detail the ins and outs of anal sex.

The websites I'd reviewed gave detailed descriptions about how to
prepare prior to engaging in anal sex. The websites described different
positions and techniques as well as preparatory procedures. I told Janie
that I'd read about anilingus and rim jobs online and wanted to try that
too. Once again, she warned me to be very careful and use a condom when
engaging in any type anal sex. Before we broke off our conversation that
day Janie told me that she'd mention to Tommy that I may want to hook up
with his younger brother to experiment sexually.


                            Chapter 4: Meeting Jimmy


A few days later Tommy's younger brother Jimmy contacted me after
wrestling practice wanting to know more about getting together. We met a
couple of more times after wrestling, feeling each other out. He came
over to my house where we browsed the Internet looking for information
about gay male sex before we made a date. Jimmy said when we got together
that I wasn't to tell anyone. I agreed and asked that he not tell anyone
either. Two weeks before my date with Jimmy, Janie presented me with a
phallic replica butt plug she'd bought on line. The little plug was
about four inches long by four inches in girth with a nice looking cock
head on it. She also had gotten me a box of condoms and some Astroglide
lubricant. During the next few days I began experimenting with the
phallic butt plug.

I used it trying to loosen my asshole up so I'd be ready the first time
Jimmy entered me. I would lube up my ass and the anal toy before
inserting it. I would place the plug in my ass of a night and then leave
it in place until the next morning. Inserting the butt plug was a painful
experience the first few times; however, after about a half dozen times I
had gotten used to it. The plug was just the right length to rub against
my prostate. I would twist and turn in bed, bringing great pleasure to me
throughout the night. I learned how to expand and contract my sphincter
pushing out like I was getting ready for a bowel movement to make entry
easier.

As I lubricated the toy and prepared to insert it I spread my butt cheeks
opening my asshole for inspection. I used one of Janie's hand held
mirror to watch my bottom as I squirted the Astroglide into my anal
opening. Then I would place the head of the toy at the entrance, tensing
up my sphincter muscle and then loosening it. As I performed the exercise
I would insert more of the phallic toy into the hole watching my asshole
gobble up the intruding cockhead sucking it past both rings into my anal
cavity. There was a flare at the base so as to not let the device go all
the way inside me.

With each exercise the entry process became more bearable, but still
there was a certain amount of pain associated with it. A week after the
first phallic present Janie gifted me with a dildo that was equipped with
a suction cup at the base: a five inch by five inch model. When I took my
shower I would attach the suction cup to the shower surround and then I
would begin fucking it with my soapy asshole while I showered. What an
incredibly awesome feeling.

Finally, the day arrived for the big date where Jimmy and I planned to
spend the weekend together holed up at his house. After school on Friday
we rode home with his older brother. Once we got to the Connor home Jimmy
showed me around. The first order of business was to stow my backpack in
his room and then eat dinner with Jimmy and his family before his mom and
dad left for Lake Tahoe.

Friday 2004 was New Year's Eve, so Jimmy's parents were heading off to
Lake Tahoe for a weekend of fun. Tommy was going skiing and snow boarding
with his friends for the weekend, so by ten that night Jimmy and I were
alone to begin our weekend of fun, a night of sex. For us the weekend
would be a cram course in sex. We went to his bedroom where we got naked
and sat cross legged across from each other on his big bed to discuss
things.

I told Jimmy that the first thing we should do was go take a shower. I
assured my friend that showering was an integral part of foreplay; it was
also to cleanse our bodies, especially our asses internally and
externally. Once we got to the bathroom and into the shower I guided the
neophyte through all prep that I wanted us to do before we got down to
having sex. In the shower I prepared Jimmy for our first sexual union.

As I stood behind Jimmy with my semi erect cock resting at his ass crack
I explained to him about my expectations for the night. I told him that I
planned to perform anilingus on him as while I played with his erect
nipples. I thought the boy was going to ejaculate before we got out of
the shower. I learned my first lesson in the shower: don't play with
Jimmy's nipples unless I wanted a sticky mess to cleanup. I also told
Jimmy that if he didn't want to reciprocate that was fine with me, but I
did want him to fuck me at least once, maybe more before our date was
over.

Once out of the shower and back in the bedroom we began touching each
other tenderly, stroking each other's bodies in a sensual manner,
tantalizing our hard cocks. Jimmy, like his older brother wasn't
circumcised, but he had a great looking cock that appeared to be about
six inches long and maybe about four and half to five inches thick, mine
was a little bigger.

Jimmy was quite taken by my uncircumcised cock, especially the glans. As
he played with me he asked if I would let him suck my cock. I agreed.
Jimmy got between my legs where he prepared to take my cock orally. I
found that due to his lack of experience I had to guide him for as few
minutes, but then he had the process down pat. I found out over the years
that guys have a natural ability, instinct if you will, for sucking cock.
After few minutes he asked me if I wanted to suck him. I told him that I
was more interested in having him cornhole me rather than sucking his
dick.

I told Jimmy that I wanted to give him a rim job before he fucked me. He
had no idea what I was talking about, but after a brief explanation he
was all for it. He lay back on his big bed while I put a pillow under his
buttock before getting between his legs. I ordered him to grab his legs,
pulling them back against his chest. Once his legs were pulled back I
asked that he reach down and spread his buttock apart. His crotch area
still smelled fresh of Irish Spring body wash and his hairless ass crack
had not a blemish. I handed Jimmy the hand held mirror so he could get a
good look at his open pink asshole. I held his ass cheeks apart so he
might get a better look. I blew my warm breath softly on his pink pucker.

Jimmy shuddered sucking in a breath. His asshole closed down at the same
time. He exclaimed that watching his asshole was totally awesome. I asked
him if he had ever finger fuck himself. To which he relied no. I told him
to watch me as I began tonguing his asshole. He wailed loudly as my
tongue touched his pink sphincter as his body convulsed and trembled.
After a few minutes I came up for air and Jimmy told me that he had never
experienced anything like that in his life. I told him there was more to
come, but I need for him to fill my ass with his dick. As I repositioned
on the bed Jimmy told me that I had one of the most beautiful looking
cockhead he'd ever seen.

My young sex partner inflated my ego telling me that my glans was a thing
of beauty. From what I'd read on line Jimmy was endowed with a pretty
average size male penis and was among roughly a third of the male
population in the United States that wasn't circumcised. Before I
prepared to get fuck Jimmy wanted to suck my cock again. After a short
while of him nibbling on my knob I suggested we stop and get ready for
him to cornhole me. I started pulling items from my backpack displaying
them on the bed.

I pulled the box of condoms and bottle of Astroglide from my backpack
that Janie had gotten for me. Jimmy remarked that I'd come well
prepared. He listened in amazement as I choreographed the details about
our first sexual encounter was to go. I also showed Jimmy my two dildos
and explained how and what I used them for. He was surprised as he'd
never seen a dildo before. He told me that I knew a whole lot more about
sex than he did and wanted to know how I knew so much. I explained that
Janie and I browsed the Internet regularly. He told me that jacking off
and a few sixty-nine sessions with his best buds was as far as he'd
gone, but he said that he was ready to try new stuff. He was curious and
definitely wanted to experience fucking me.