Date: Mon, 23 Oct 2006 19:04:58 -0700 (PDT)
From: Will Shakespear <playbuddy123@yahoo.com>
Subject: Sissy Brother- 13

Disclaimer: This is a work of FICTION. Any similarity
between my characters and real people, places, or
events is merely a coincidence. This story contains
descriptions of imagined sexual activity between
teenage boys. If you are not 18 years old or if it is
illegal where you live to read material of this kind,
please stop here. If this story might offend you
please go to another site. Please do not copy,
distribute or reproduce this material for anyone or
any site, without the author's explicit permission.
Everyone please enjoy and feel free to send comments
and story ideas to playbuddy123@yahoo.com.

                 Sissy Brother - 13

My last class ended and I was standing in the hall by
the Biology classroom when Trevor and Michael walked
by. "Hey squirt" I said as a couple of cheerleaders
giggled nearby and waved at me. "Hey" Trev answered
and walked up. "I'm riding home with Devon." I rolled
my eyes, "Don't say it!" he warned and I took the
hint. "Okay, Okay" I muttered. Michael flashed me a
smile. "Hey Jeremy" He offered with a puppy dog look.
"Sup?" I asked, not really caring what he might
answer. "You going to the Halloween party at the
community center?" Michael asked after a minute of
silence. "Maybe, I don't really know yet" I said
glancing down the hall at the ass of a fine looking
senior girl. "We gotta go" Trevor said as he pulled
Michael's arm and started to walk away. "See ya"
Michael said turning to look back at me as they
walked down the hall.


Devon picked Trev up at the front door of the school
and took off for the YMCA. "Got your suit?" Trev
asked as Devon turned left onto Maple. "Yeah" he said
and flashed my brother a grin. "This was a great
idea!" Trev smiled back, "I haven't been swimming
since school started." Devon turned right onto
Jackson Avenue. "Me either, once football started
there hasn't been time." Soon they pulled into the
lot. Fifteen minutes later they were walking out of
the locker room. "Nice butt" Devon teased staring at
Trev wearing his small red Speedo. Trev giggled,
"Nice bulge" he teased back glancing at the front of
Devon's suit. They both laughed.

There was a water volleyball game going on so the
guys joined in with that. As you might guess, Devon
excelled. Trev didn't do too badly either, his
slender body and longer legs worked to some
advantage. They played for more than an hour and then
goofed around. At 6:30 the pool closed for general
swimming and the guys got out and showered. "What?"
Devon said as Trev checked him out in the shower.
"Just looking" Trev giggled and wiggled his rear end
as he left the shower heading to the lockers. Devon
grabbed a towel and twisted it. "Don't you dare!"
Trev warned, and Devon grinned and snapped it across
his ass. "Fuck!" Trev squealed as he ran around the
lockers trying to protect his butt from another
attack. An old man and his kid looked at the two and
Devon backed off. Trev and Devon giggled as they
dried off and got dressed. Devon dropped Trev at our
front door and Trevor leaned in quickly and gave him
a soft kiss on the lips. "Thanks" he said and ran to
the door. He waved as Devon pulled away.

We had supper with the folks and talked about school,
sports, and plans for after football season. Neither
of us
talked about dating, there are some things mom's and
dad's don't need to know. I was in my room when I
heard Trev squeal. Jennifer had brought over the
package she had bought for me as part my pay off to
my brother. I had left the box on his bed. My door
flew open and Trev ran in and wrapped his arms around
my neck. "Just what I wanted" he grinned and gave me
a kiss on the cheek. "Whatever!" I
grunted, unsure how any guy could get so worked up
over a girl's nightie. Trevor ruffled my hair.
"Thanks bro" he giggled and headed back to his room.


The Halloween party at the community center was a
pretty big thing in our town. The school didn't put
on a Halloween dance, so the town arranged an all
night deal at the town gym. There would be swimming,
volleyball, basketball, food, and everyone would stay
there until morning. Devon had called and said that
he and Trevor were going to be there and wondered if
I would. "Don't know" I had answered. Jennifer was
going out of town with her folks so I would have to
go alone. Trev was eating corn flakes one morning
when I asked, "Is Michael going to that thing at the
community center?" Trev looked up, "Halloween party?"
he mumbled. ""Yeah" I said trying to look
uninterested." I guess" he mumbled as he reached for
some more milk. "Maybe I'll see you guys there" I
said as I put bread in the toaster.

The night of the party I dressed up in leather pants,
leather jacket, and a helmet with some other stuff
that made me look like a biker. Trev dressed up like
Jack Sparrow, though I have to admit he looked like a
pretty gay pirate. Devon picked us up and he was
dressed as a pirate as well, only he really looked
the part. I spent the next hour or so wandering
around the building seeing friends and generally
having a pretty good time. "Hey" a voice called and I
turned to see Michael dressed in a little white
sailor uniform. "Ha!" I started to laugh. He looked
too ridiculous to not laugh. Michael's face fell from
a smile to one of hurt. Then he got teary eyed. "You
don't have to laugh" he whispered and a tear fell
down his cheek. "Sorry" I finally said as my laughing
binge came to an end. "You look fine" I offered.
Michael still stared at the floor. "In fact, I was
kind of looking for you" I said as I looked around to
make sure no one was watching us. "You were?" Michael
brightened up. "Yeah" I said. "Cool" Michael grinned.

We spent the next hour talking, walking around the
building, eating, and sometimes playing one of the
games. I got a couple of looks from friends of mine
and I just ignored them. One guy said something about
me spending time with a freshman and I just gave him
the finger. "You said you were looking for me"
Michael said as we sat in a corner of the bleachers
watching some guys play basketball. "Yeah" I said
without turning to look at him. "Why?" he whispered.
"Don't know for sure" I said starting to feel less
than comfortable. "I was hoping you'd be here"
Michael offered and I turned to look at him for the
first time.

I thought for a moment. "Look, I'm straight and I
have a girlfriend" I started to explain, "but you
have an ass to die to for" I grinned and laughed.
"All I am to you is a fuck?" Michael asked. "Pretty
much." I said as I leaned back and rested against the
bleacher, my dick and nuts visible in the tight
leather jeans. It was quiet for a couple minutes.
"That's cool!" Michael grinned. I turned to look at
him. "What?" I said. Michael whispered, "I'd like a
boy friend" he said looking a round to make sure no
one could hear. But I'll settle for a fuck buddy" he
smiled. I took a long look at the slim freshman with
shoulder length hair, cute rear end, and all too
willing smile. "Cool" I said and gave my crotch a
squeeze. Michael giggled. "So what are we doing
sitting here?" He asked. "Fuck if I know" I giggled
and nodded toward the door.


The fact that I was not yet sixteen and didn't have
my license was becoming a pain in the ass. It was
only two months away, but it might as well be two
years. "Where can we go?" I asked Michael as we
headed to the door. Both of us were eager to be
someplace where we had some privacy. He pulled his
cell phone from his pocket, "David? It's me Michael"
he said as we reached the front of the building. "I
need a ride" he explained nodding and holding up a
hand to keep me quiet. "Twenty minutes?" he asked and
then nodded. "Okay" and hung up. I seemed to remember
Michael had an older brother. "Is that your brother?"
I asked. "Yeah, he dropped me off here, "He goes to
Hamilton Academy". He said. It was the private
college prep school across town.


Before long we were at Michael's house headed for the
basement family room. "My parents are upstairs
watching TV he whispered" and put a finger to his
lips to remind me to be quiet. The room was filled
with soft leather couches facing a gas fireplace and
TV entertainment system. He clicked a switch and the
fireplace lit up and he turned the lights low. I sat
on the couch and he instantly got on his knees in
front of me feeling the bulge in my pants. "Time to
let the guys out" he giggled as he lightly brushed my
balls. I pulled on my belt as Michael undid the
button and pulled down my zip.

The freshman smiled as he reached into the tight
pants and felt for my cock. "Nice" he whispered as he
pulled my dick out and gave it a gentle stroke. I
felt his soft hair and gently urged his head down as
I lifted my hips up. "Suck it" I moaned as Michael
took my cock into his warm mouth and played with my
nuts. His tongue swirled around the head of my dick
and teased my piss hole. He clearly had done this
many times before. I looked down at the long hair
sissy on his knees in front of me and my prick
jerked. I rubbed his back a little as he deep
throated my 7.5 inches and didn't gag or complain. He
worked his tongue around my dick and stroked me.
"Sweet" I moaned as I raised my butt off the cushion
and fucked his face.

I knew I was getting close. "Almost there" I warned
and Michael pulled off. He grinned and got up quickly
and ran to the small powder room at the base of the
stairs. He came back grinning and waving a jar of
hand cream. He handed me the jar and then stood
inches from my face as he undid the bottoms of the
sailor suit. I laid the jar on the couch and helped
slide his britches down. The soft material pulled
down easily feeing his cock and baring his butt. He
smiled, turned, and bent slightly putting his ass in
front of my face. I felt his perfectly round buns.
"Yes" he moaned as I felt his ass cheeks and ran a
finger up and down his crack.
I opened the jar of hand cream and lubed my middle
finger. I teased his pucker and then slowly inserted
it into his rectum. I twisted my hand around so my
palm was facing up and drove my finger as deep as I
could into his butt. He grunted, "Fuck" as I found
his prostate and massaged it. "Oh God" he moaned
again and wiggled his ass on my hand. "Finger my
hole" he pleaded as he bent over further almost
touching his toes.


A few minutes went by and I pulled my finger out and
watched his hole slowly close tight once again. I
scooped some cream out of the jar and lubed my rock
hard dick. "Turn around" I commanded. Michael turned
to look at me sitting there with a stiff pole. I
motioned and he smiled. Michael squatted over my
cock. My ass on the edge of the couch, he grabbed my
shoulders and sat down impaling himself on my teen
dick. I felt my knob at his anus and then felt it
slip past the tight ring and go deep up his butt.


"Fuck" I moaned as I lay back against the sofa and
let Michael screw himself on my penis again and
again. I thrust up to meet his downward jabs and we
both were soon moaning. About ten minutes went by and
Michael whimpered, "my legs." I figured he had gotten
a cramp. I grabbed his waist and he climbed off. I
stood and pointed a finger toward the couch and
Michael lay face down and ass up. He buried his face
in a cushion and I lay on his back. I thrust my cock
between his cheeks and deep into his butt. "Oh yeah"
he moaned as I pounded his rear end again and again.
The sound of my balls slapping his ass cheeks filled
the otherwise quite room. I looked at his long hair,
slim build, and couldn't help but think I was fucking
a girl up the ass. That idea really made my horny.


My fucking got wilder and I pounded that kid's ass as
hard as I could. "Jeremy!" he grunted and by the
sound of his voice knew something had happened.
"Damn" I grunted as I felt something warm and soft
just at the end of my downward thrusts. I had pounded
his ass so hard he needed to shit. "Fucker!" I moaned
and that put me over the edge. "Here it comes
Michael" I grunted and slammed my dick home. I spread
my legs and rose up a bit as I fucked the kid as deep
as I could. I pulled him to his knees, face down ass
up. I got on my feet and slammed his hole over and
over again.

"Fucking cunt!" I grunted as I finally shot my load.
My nuts let loose and I flooded Michael's rear end
with sperm. "Oh God" he moaned as he felt my cock
spurt. He reached under himself and stroked his own
cock with a purpose. "Shit, shit' He grunted and I
felt his ass hole contract and try to bite my dick
off. I grunted and slammed him again. "Fucking queer"
I groaned as I fucked his hole again and again. I
squirted my juice up his ass and filled his butt with
cum.

Exhausted I pulled my cock out and sat on the end of the couch.
Michael still lay face down, his breathing was fast and labored.
The top of his little sailor suit was bunched up under his arm
pits and his ass was a mess. Slowly he recovered and went to the
bath and brought back a warm wet wash cloth to clean my dick and
wipe his ass. A few minutes later he came back, lay on his back,
resting his head in my lap, he looked up at me. "Pretty wild" he
whispered. "Yeah, pretty wild! I agreed. We stayed like that for
maybe fifteen minutes just looking at the fire, our dicks hanging
out.


Michael crawled up and sat in my lap facing me. He hugged me and
we kissed. "Do you always fuck that hard?" He giggled looking
into my eyes. "Only sailors" I laughed. He grinned and laughed
too.

A quick thought crossed my mind as I stood and started to pull up
my pants. "Wonder what Trevor is up to?" I wondered as I looked
at Michael bending over to pull up his pants. "More to the point,
what's Devon up to?" I smiled and gave Michael a firm smack on
his butt. "Hey!" He complained. You're ass is mine sissy!" I said
sternly. Michael thought for a second. "Anytime." He grinned.


Write me with your comments and ideas. Playbuddy
123@yahoo.com