Date: Sat, 28 Oct 2006 13:12:07 -0700 (PDT)
From: Will Shakespear <playbuddy123@yahoo.com>
Subject: Sissy Brother- 15

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 - 15

Thankfully there wasn't any school the day after the Halloween
party so Trevor and I slept in and caught up on our sleep. Mom
and Dad left for work early and didn't even bother trying to get
us up. I was in that twilight between sleep and being awake when
I heard water running in the bathroom and the sound of Trev
brushing his teeth. I rolled over and hid my head under a pillow
hoping to shut out the daylight that was creeping into my room.



I was almost back to sleep when the bed moved and I opened one
eye just enough to see Trev pulling the covers up to his chin as
he climbed in with me. "What?" I yawned. When we were little Trev
often got into bed with me, but he hadn't done that for years. He
turned onto his side to face me and we stared at each other from
only inches apart. Trev was smiling a sweet smile when he said,
"Thanks Jeremy". I was a little puzzled, "What for?" I mumbled.
"Thanks for being friends with Devon." he gave me a little kiss.
I yawned. "So did you get laid?" I asked as I stretched and
pulled the covers up to my nose to stay warm. "No! Devon made
love to me." Trev said as he snuggled closer. It was then that I
noticed something strange. "Shit!" I said as I woke up to the
fact that Trevor was wearing the baby doll nightie that he had
forced me to buy for him. Trevor giggled. "Nice isn't it" He
grinned. I turned away from him to face the wall, a little
disgusted, "Little Sissy Fag! I yawned and closed my eyes and
tried to get back to sleep.




A few minutes went by but Trevor didn't get out of my bed. I felt
his breath on the back of my neck as he cuddled closer. I could
also feel the warmth of his warm body as he squeezed close. I had
almost drifted back to sleep when Trevor's hand slid down my ass
and wiggled between my legs. He played with my ball sac from
behind. My boxers began to tent. I moved one leg a little to give
him some room and he reached further and stroked my cock through
the front of my shorts. "Feels nice bro" I whispered as I let
Trev have his way with me. I turned over and faced my brother and
we both smiled as he groped me again, only this time from the
front. He leaned and kissed me. "Are you trying to take advantage
of me?" I teased. "Maybe" he said with a sly grin. My eyes
twinkled, "You know you always use me!" I teased back. We both
giggled knowing it was the other way around. By this time my dick
was totally hard. I felt for his cock underneath the silky
nightie. He too was hard. "So what do you want?" I whispered as
Trevor gently stroked my cock through the slot in my underpants.
"This!" he said and gave my dick a little squeeze. "Think you can
handle it?" I whispered. "I've had bigger!" he grinned, "You
Slut!" I laughed and Trev giggled back.



Without saying another word Trev rolled over onto his side and
faced away from me. He scooted his butt against my crotch. I
pulled my boxers down over my ass and my dick popped out and
immediately settled between my brother's warm butt cheeks. "We
need some lube." I advised. Trev pushed his hind end back against
my dick. "It's ok" He whispered. I put an arm around my brother
and pulled him closer. My cock moved deeper into the cleft of his
ass. The tip of my dick touched something wet. "You greased your
hole?" I whispered and Trev giggled. "I learned in scouts to
always be prepared!" I giggled. "Well, here it comes then" I
warned and eased my hips forward. The tip of my cock seemed to
melt into his butt. The tip of my penis entered his rear end
easily and slid deep into his rectum. We both moaned it felt so
good. "God, I love cock" he grunted as he wiggled his butt and
urged me to go deeper. "Your ass is so sweet" I grunted as I
thrust further into my brother's butt and planted my pubes
against his cheeks.



Something unusual was happening between us. A kind of gentleness
and unhurried love making was starting. I began a slow, lazy in
and out fuck that lacked urgency and lacked my usual disregard
for my brother's feelings. Most times, I simply needed a hole and
didn't care what he felt about it. This time I wanted to cuddle
close to the little brother that always looked up to me and
always wanted me to play. "You really wanted this? Didn't you?" I
whispered as I lovingly penetrated Trevor's ass again and again.
"Yeah" He moaned and bent a little squeezing his butt back
against my crotch. "Nail it" he pleaded asking for more of my
cock in his ass. I thought of really pounding the little fucker.
I knew I could fuck him so hard his teeth would chatter, but
instead I made thrusts that were long, slow, and deep. I worked
one arm under Trev and the other over him and hugged him close.
"Fuck me!" He whined, he wiggled his ass, "Jeremy, never stop
fucking me!" He was giving himself to me totally. "Jesus, fuck me
deeper." He grunted as I thrust again and again into my little
brother's butt.



His hand went to his own cock and he began to jerk. "Shoot it
Trev!" I urged him, and I tried to coordinate my thrusting in his
ass with his jerking. We moved faster, our breathing increased,
and finally after many minutes of enjoyable fucking we neared
orgasm. Trev moaned, "Oh God, Oh God" as his dick spewed. Squirt
after squirt his cum shot out. I came at the same time. My cock
pumped his butt full of hot cream and I moaned it felt so fucking
good. My dick twitched as it shot and afterwards I heard
squishing as my cock slammed into his wet and slippery hole. I
crammed my dick up my brother's butt two or three more times as I
spurt the last of my cum, and then rested. Neither of us spoke
again. We wiggled and bumped a little trying for a couple more
minutes of bliss, but we didn't say anything. Finally my cock
shriveled and slipped out of Trevor's ass. After a few minutes
more of silence Trev spoke up. "Well, I guess we finally found
something your good at!" Trev giggled and wiggled his butt back
against my crotch. "Hey! I'm good at football!" I complained and
he rolled over and gave me a quick kiss. "I make a better wide
receiver than you do!" He laughed and looking at his sweet ass
and tight hole I had to agree. I laughed as well.


I felt around for my boxers which had slipped down to my knees as
we fucked. I pulled them off and wiped the slime off my dick,
tossing them in Trev's face. "Clean the cum out of your ass
smarty pants!" I said and crawled over him to head for the
shower. A few minutes later Trev opened the shower door and
walked in. We had a nice time of touching, laughing, washing, and
playing soapy games with one another. We finished, grabbed
towels, dried off and headed to our rooms. A few minutes later I
came back naked my balls swinging. "Forgot to put my things in
the laundry" I said as Trev was pulling on his jeans. "Can I wear
a pair of your boxers?" Trev nodded and motioned toward his
dresser. I opened the drawer and saw two neat piles of underwear;
boxers and tighty whities. Just peeking out from the bottom of
one pile was the outline of a pack of cigarettes.
Trev had his back to me. I lifted the stack of boy's briefs and
uncovered a pack of Virginia Slims. I grunted to myself, "The
little fairy even buys girly cigs". I grabbed a pair of boxers,
covered up the cigarettes and closed the drawer. As I headed bare
ass toward my room I looked over my shoulder. "Don't let mom see
those smokes" I warned as I paused by the door. "She'll ground
your little sissy ass until Devon is so old he won't be able to
get it up!" Trev's face grew pink. "Don't worry, I won't tell" I
smiled as I pulled the boxers up over my butt. "Besides" I
thought," If anyone ever finds what I got stashed we'll both be
in deep shit!"


It was a few days later that my life took another turn. Gym class
had just ended and we were in the locker room when Josh, the new
kid in school, opened the locker two doors down from mine. I
really didn't know too much about him, but I had heard he was
pretty smart, got good grades, and his mom was in fashion design
or something. His dad was an executive in the aerospace industry.
Josh looked my way as he got a towel from the basket at the end
of the aisle. "Hey" he said and flashed me a killer smile. "Sup?"
I smiled back. He held out his hand, "I'm Josh" He said and I
grinned as I shook his hand. "Jeremy" I said in return.

"Play any sports?" I asked as I pulled off my shoes. "Yeah" he
said as he began to undress. "I lift weights, swim, and play
baseball." Then he pulled his shirt over his head and revealed
the most perfect set of abs I have ever seen. "Shit!" I said,
without thinking and then blushed. "Sorry!" I turned my head
away. I stammered a second "You look great, you must really work
out!" Josh laughed. "Yeah, I spend a lot of time in the gym". We
finished stripping down, and headed for the showers. Josh was a
few steps ahead of me so I had a chance to check him out from
behind. He looked to be about 6'1" tall, lean, well defined
muscles and the perfect proportion of muscle to fat. He looked
like he could run 15 miles and never break a sweat. "God, I wish
I looked that good" I mumbled to myself.

We showered and I casually snuck a quick glance at his front. His
firm stomach had a treasure trail of hair leading to a nice
looking dick. It was about average, nothing huge but he had a
nice patch of hair down there and his cock looked very
substantial. "Nice package!" I thought as he finished his shower
and walked away.

The second gym class we had together, Josh settled in right next
to me. "You mind?" he asked as he opened the locker right next to
mine. "Naah, its ok" I said trying not to stare. When we were
both naked and ready for the shower, Josh leaned over and
whispered. "I hear you like to fuck sissyboy ass." I almost shit.
My heart pounded. "What?" I said, as I tried to play dumb.
"Wonder where the fuck he heard that?" I thought to myself. Josh
stood up, "Michael lives door to me." He said and flashed his
trademark grin. I shook my head, "Little Shit!" I cursed. "It's
cool" Josh said. He turned half way toward the showers flashing
me his dick and part of his firm full ass. "Maybe you'd like to
try a real man sometime!" He winked and turned toward the
showers.


I couldn't take my eyes off his tight athletic ass and rock hard
body. "Damn" I said to myself trying to keep my dick from getting
hard. "Not here, not now" I chanted trying to keep my cock
relaxed. I wrapped a towel around my middle just in case I lost
the battle and headed toward the end where I knew the cold
showers would be.


As fate would have it Josh had a change in his class schedule
which meant that he now had the same lunch period as me. I kept
telling myself that I wasn't interested. I mean fucking Michael
or Trev is different. It's practically like fucking a girl. "Shit
they wear panties, have long hair, and everything." Josh on the
other hand is a total jock. There's nothing sissy about him. "I
don't know," I whispered to myself as my eyes stayed glued to
Josh's jeans as he walked out of the lunch room. "He has a
fucking sweet ass though!" I took a bite of my apple and swirled
it around in my mouth, "Something to think about!" I mused,
"Something to think about!"



Michael dropped his back pack on the table next to me and sat
down. I quickly looked around the room to see if any of my
friends were watching. "I don't eat lunch with freshman!" I said
as he tossed me a smile. Michael's grin changed and he clearly
looked hurt. I felt like an asshole. Most days I ate lunch with
Jennifer but today she had student government. "Okay" I finally
said. "Just today". Michael grinned and then started rambling on
about his classes, some algebra crap and a lot of shit I really
didn't give a damn about. My mind went back to Josh and as I
thought about his ass my dick reacted. I could feel my jeans
becoming tight and I gave a quick glance around and put my hand
down there and shifted my underwear so my cock wasn't twisted.
"Fuck, I'm horny" I thought as Michael continued babbling on
about some cousin of his that was going to come for a visit. I
couldn't take any more. "Shut the fuck up!" I whispered, and
Michael stopped in midsentence. "I'm horny! You want to suck some
cock sissy boy?" I said quickly looking around.

Michael got wide eyed. "What? Here, in school?" He whispered. I
gave my dick a squeeze. "Check it out" I said glancing down.
Michael looked at my crotch, and swallowed a piece of his
sandwich. I saw a bulge start in his pants. "You know you want
it!" I teased and raised my eye brows. Michael wet his lips with
his tongue. "I have a key to the sound booth in the auditorium."
He whispered. "I'm on stage crew". I grinned, "Good boy! Ten
minutes!" and I stood and walked away.

Fifteen minutes later we both slipped into the control booth and
Michael locked the door. The auditorium was dark and no one was
going to be around for a couple of hours. I went to the sound
board and looked out the glass window then down at the stage.
"Nice" I said. I turned around and sat my ass on the board. I
unbuttoned and pulled my zip down. "Okay Michael" I said as I
pulled my cock out. Michael's face lit up as he went to his
knees in front of me. "Fuck I need this" I groaned as I gave my
dick a stroke. "Open up" I ordered and Michael eagerly complied.
"Oh yeah!" I groaned as the little sissy started by licking my
knob. I grunted a little as I took his face in my hands and aimed
my penis and slipped it passed is lips and began to fuck his hot
little mouth.


Michael played with my nuts and stroked my cock as he worked his
tongue back and forth. He pulled me in and out of his mouth,
sucked, tongued my piss slit, and deep throated my dick like he
had been doing it since birth. "God you're a good little
cocksucker" I moaned as I thrust my hips forcing my dick deeper
into his throat. He opened his mouth wide and I stood up. I held
his head and began to fuck his face like it was a cunt. He
dropped his hands down and unzipped his pants and pulled out his
dick. He began to jack himself as I pumped my penis between his
lips. "Getting close" I grunted as I felt the tingle in my groin.
He slurped at my dick and put a hand on my cock as he took over
control. I felt Michael's hair, looked at his angel face sucking
my dick and thought of Josh and my dick shoved a mile up his
tight ass.


I was at the edge. "Swallow it!" I grunted as I felt my balls
pull up tight and shoot my load into Michael's mouth. He sucked
at my dick like a baby bottle. He pulled my cock with one hand
while he masturbated himself with the other. Three strong jets of
sperm shot out of my dick and the kid hungrily swallowed each
one. Just as he managed my last shot his cock erupted and his
spunk shot onto the floor. He pulled my dick from his mouth and
gasped for air. He burped, grinned and stroked my dick and wiped
it on his cheek. He painted his face with the remaining juice
still on the tip of my dick. Two more tugs and his cock was spent
too.

As I recovered I took my penis in my own hand and rubbed it
against Michael's lips. "Clean it off honey" I whispered and
Michael grinned and sucked me clean. I tucked my wet dick back in
my pants as Michael stood and put himself back together. I put my
hand on the Michael's cheek and then softly moved it to the back
of his neck. "You make a pretty good girlfriend" I said tenderly
and then gave him a quick little kiss on the lips. "I think I'll
have lunch with freshman more often" I smiled, and Michael
giggled.

I want to thank Taylor and Steve for suggestions for this
chapter. Readers ideas are always welcome. I hoped you enjoyed
it. Write me. Playbuddy123@yahoo.com