Date: Tue, 14 Oct 2008 09:41:46 +0000
From: john doe <criedfornoone@hotmail.com>
Subject: Babysitting James (gay/young-friends)

Warning the following story contains graphic depictions of
sex of a homosexual nature if that sort of thing offends you
read no further. Also there is small amount of coercion
present in this story, while I don't condone coercive sex in
real life, there is nothing wrong with fantasizing about it.

I wrote this story two years ago and never posted it. I
think this is the first story I ever finished. Feedback is
appreciated at criedfornoone (at) hotmail (dot) com


My name is James, I'm17 years old and I'm going into the
12th grade next year. I have brown hair blue eyes and a
medium build. Most girls think I'm something of a hunk. Too
bad I don't like girls. I'm really attracted to boys,
especially ones who are 12-14, though older and younger ones
turn me on too. So you can imagine how happy I was when I
found out my moms friend was going to be out of town with
her new boy friend for a whole week and needed me to watch
her 13-year-old son. Taylor was beautiful he had shoulder
length blond hair blue eyes and a very feminine face; he was
often mistaken for a girl. His mannerisms were somewhat
effeminate too but not overtly so. I was sure he was gay but
he is what we call a passer, most people wouldn't notice
just from talking to him.

The first day I came over on Friday evening at 6 o'clock
when I knocked on the door Taylor answered smiling, god it
melted my heart, it was going to be hard to keep my hands
off him this week I was glad I had the for-sight to jerk off
a few hours before I came so I wouldn't get too excited
around him.

"Hey kiddo," I said.

"Hi James"

"Where's your mom at?" I asked.

"She's inside"

He led me in to their two-story house; his mother was in the
kitchen with her boyfriend Chris getting her bags together.
After giving me instructions on sleeping arrangements and
showing me the guest bedroom she told me the rules for
Taylor, like in bed by 10, no watching "late night" cable
movies that sort of thing. She bid Taylor good bye and gave
him a kiss on the cheek.

"I'll be back in a week, be a good boy for James or you will
get it from Chris when I get back, I love you"

Taylor and I watched as she left and then I turned to Taylor
and said.

"Well, do you want to show me your room?"

"Sure"

I followed him upstairs, my eyes glued to his wiggling ass,
god he was sexy. I felt my self start to get an erection. He
is about 5' 4" and 115 pounds, very slim. I'm 5'11 and 190.
His room was typical of a young adolescent he had a computer
in his room, poster of various rock bands like System of a
Down and Tool.

"Hey I like System" I told him

"Really?"

"Yeah, I have been listening to them since their first album
came out when I was 13."

We talked about that for a while, and then we played Halo 2
on XBOX. At 9:30 I told him it was almost time for him to go
to bed. Reluctantly he agreed and told me he was going to
take his nightly shower. "Okay," I said and made myself busy
by organizing my cloths and such in my temporary room. 20
minutes later he came out of the shower and I got a glimpse
of him with the towel around his waist. I couldn't help but
wonder what he was doing in there and why he took so long.
At around 10 I came in after knocking, he was wearing boxers
and a t-shirt. I got an immediate erection.

"Okay bedtime"

"All right, good night James"

At 10:20 I got up to use the bathroom and noticed a faint
glow coming from underneath Taylor's door. My curiosity
peaked, I leaned close to the door but could hear nothing. I
knew he must be at the computer and my heart began to pound
when I thought he might be looking at porn online and
jerking off. I knew the right thing to do would be to knock
first but I also knew that I want to see him in that
position more then anything in the world right then. Open
here I flung the door and there was Taylor with his hand
wrapped around his hard little cock sticking through his
boxers shirtless.

"Shit" he said. Trying to cover himself he immediately
turned off his computer screen. Even in the darkness I could
see him turn bright red.

"What are you doing, you're supposed to be asleep?"

"I was just err checking my email is all" he said shakily. I
could see his penis was still hard and trying to break
through his thin boxers.

"Your mom told me specifically that you were to be in bed by
10 and not to let you look at pornography."

"I wasn't I swear"

"Really? Lets see," I reached over and turned the computer
screen on, slowly the image brightened it was of two guys
one around 20 with a medium build getting a blow job from a
skinny teenage guy. I couldn't believe my luck, my heart
raced even faster and then I noticed the look of horror and
shame on tailors face. I wanted to tell him that it was all
right to be attracted to men and that there was nothing
wrong with masturbating but I couldn't find the words. Then
I noticed Taylor was crying.

"Hey you don't have to cry"

"Please" he said sobbing "Don't tell my mom about this, she
doesn't know"

"Well I think I have to, she told me to tell her if you did
anything you weren't supposed to do and she mentioned porn
as one of those things." My heart was torn I wanted to tell
him it was okay and I wouldn't say anything but the other
part of me wanted to use this as leverage to see if I could
get in his pants. Then I thought, I can't stand to see him
this upset, I'll just tell him I won't say anything.

"No, you don't understand Chris will hit me"

"Hit you? Do you mean like a spanking?"

"Well he has before but if he found out I was looking at
guys he might punch me." He said still sobbing

"I wont tell them you were looking at guys if that's what
your scarred of, but I think I'd better say something" I
said lying through my teeth, I couldn't bear to do that
honestly

"What if you punished me?"

I almost came in my pants at the implication he was making

"What you mean if I spanked you?"

"Yeah" he looked up at me hopefully

I should say no, and tell him to forget it I thought

"Okay I wont say anything if you let me spank you" did I
sound too excited? "Come over here" I sat down on the bed.

"Now take off those boxers"

"You want me to be naked?"

"You want me to spank you right? If I'm going to do it has
to be your bare ass"

He didn't say anything and looked at his feet while he
slowly slid down his boxers. He looked very embarrassed.
There before me was the most beautiful boy cock I had ever
seen, he still had a semi, it was about three inches long
and an inch wide with a very light dusting of blond pubes
above the base. He was completely hairless everywhere else.
As I looked at it I noticed it was growing, he tried to
cover himself. The sexual tension was obvious even to him

"What now" he asked not looking up


"Lie across my lap"

He bent over and laid his bare skin across me, I was wearing
track shorts and nothing else, I knew he could fell my
erection pressing against him. I looked at his perfectly
smooth ass and I wondered how I could be so lucky, I rubbed
it for second then I began to spank him. Not too hard but he
could defiantly fell it and his ass was red after the 20th
whack. I noticed now that both our cocks where very hard I
could fell his pressing against my leg
I closed my legs together tight around his cock and I began
spanking him again
I leant close to his ear as I was smoking him and whispered
hoarsely "you like this don't you?" He only moaned in
response and began humping my leg. After the 30 more whacks
I stopped and began caressing his smooth ass"

"Spread your legs" I told him

He said nothing but spread them. I saw his tight little hole
there before me, all mine. I licked a finger and stuck it
in, he jerked but still said nothing then I began to spank
him again. He started humping my leg more feverishly and
after a minute or so I felt him tense up and his cock pulse
as he erupted against my leg. I took my fingers out of his
ass and stood him up. We looked in each other's eyes and I
kissed him on the lips. On your knees and suck me I told
him. He did as he was told and put my cock in his mouth. I
could tell this was his first time. I started humping his
face and then pulled out, "Bend over the bed," I said.

He stood up and I bent him over. His cock was already back
at its full 4-inch length. I grabbed the jar of Vaseline he
was using to pleasure himself and smeared some on my cock. I
then got behind him and placed my 7-inch dick at the
entrance of his sweet cherry. I pushed gently forward, he
moaned. I stopped once the head was in then started pushing
the rest of the way in. he was very tight and I knew he was
in pain but he wanted it as much as I did. I pushed in inch
by inch until my pubes were against his ass. I waited about
30 seconds and then I started to fuck him in and out. I went
slowly at first but picked up the pace, I knew I wouldn't
last long fucking his little virgin ass. He moaned softly as
I plowed him, a look of pain and pleasure on his sweet
little face.

I kissed him on the neck and on the ear I was fucking him
hard now giving him every inch of my thick meat, he moaned
softly each time I pushed in. I grabbed his hands and pulled
them above his head as I fucked the boy. I could feel the
cum bubbling in my balls. I grabbed his hips and started
pounding faster and faster as I felt my orgasm coming. "Shit
your ass is hot, I'm going to cum inside you James" I said
and then I felt him start to tremble as his second orgasm
overtook him, his ass squeezed down on my cock as he came on
the bed and himself, that was all it took I shoved hard into
him and his trembling ass milked my cock for the next 30
seconds as I deposited the biggest load of my life deep in
his tight boy hole. I collapsed against him and kissed his
cheek

"That was wonderful," I said
then I kissed him on the cheek. We cuddled up together on
the bed end I pressed his smooth little body against mine. I
rubbed his stomach and whispered in his ear "your so
beautiful." And we drifted slowly to sleep.

We continued on for the next week and I fucked him up down
and sideways. I fucked him on the bed, I fucked him on the
stairs, I fucked him in the shower. By the time his mom got
home James was starting to get sore. Luckily that wasn't the
last time I babysat for James. But the first time was
certainly the most memorable.