Date: Sat, 18 Nov 2006 11:54:07 -0800 (PST)
From: Will Shakespear <playbuddy123@yahoo.com>
Subject: Sissy Brother -18

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 - 18

The day after the party at Michael's house I woke up early in a
very good mood. I had dreamed of our Friday night activities and
that left a big smile on my face. I stretched my arms and legs
under the warm blanket and rolled over to my side pulling my
knees close to my chest. My right hand drifted down between my
legs and I gently played with my dick. I kept my eyes closed not
quite ready to get up. My belly churned a little and squeezing
some stomach muscles I cut a loud fart. I yawned and reluctantly
decided it was time to get moving.


I walked into the bathroom and Trevor was sitting on the can
reading a soccer magazine. The air smelled bad. "Damn, that's
nasty!" I said wrinkling up my nose and turning my head away. I
looked back and Trevor shot me a finger and continued his
reading. I thought about brushing my teeth but that would mean
standing closer to Trev. I decided against that and instead
turned on the water in the shower. When it was warm I dropped my
boxers to the floor and stepped in.


The soft warm spray felt good on my back and the feel of the soap
on my skin was nice. I flexed my bicep and watched it bulge. "Not
bad!" I thought to myself and admired my body. My arms and legs
were strong and had a light covering of hair; my chest was smooth
with a treasure trail leading to a nice patch of pubes around my
dick and balls. I felt the smooth globes of my ass as I soaped my
crack. I let my fingers travel up and down the groove. I
remembered how good it felt to have Michael's tongue back there
and my finger lingered.


I put some more soap on my hand and leaned against the shower
wall. I bent over a little and put a soapy finger against my
hole. I felt around my pucker and got a sweet tingling sensation
as I touched the tight ring. I pushed a little and let the tip of
my finger slip into my butt. My dick twitched and I felt myself
getting hard. I wiggled my finger a little more and found I
enjoyed the feeling of something going in instead of just coming
out.


I heard the toilet flush and suddenly the cold water stopped and
the shower turned scalding hot. "Shit!" I yelled. "God Damn it
Trevor!" Jumping back from the hot water, I heard the lid slam
down on the toilet. "Sorry!" Trev said and quickly left the bath.
The water returned to normal and I finished my shower. As I dried
myself with a towel, I stood in front of the medicine cabinet. I
couldn't help but think of the jar of Vaseline sitting on the
shelf just behind the door. I knew mom used it when she put the
enema hose in our butts. My cock got hard thinking of my hole
again. I opened the cabinet and lifted the jar. I looked to see
of Trev was watching, but his door was closed. I quickly searched
the room for something I could play with. I looked in several
places but couldn't seem to find anything that would seem to
work. Then, I saw our toothbrushes hanging on the wall. I stared
at the slender handle and imagined it sliding into my rear end. I
grabbed one and headed to my room.

I closed and locked my door dropping the towel wrapped around my
waist. I popped the top off the jar of Vaseline and greased the
smooth end of the toothbrush. I got on my knees on my bed,
putting my head down and raising my ass up. I took a deep breath
and put the thing to my hole. In one slow thrust I eased it up my
butt like a rectal thermometer. "Oh God!" I moaned as I felt the
cool plastic slide into my rear. I pulled the handle out slowly
and pushed it back in again fucking myself. My cock was hard as a
rock and I started to drip. "So good!" I moaned as I used the
handle like a dildo slowly teasing my ass. I dropped onto my
tummy and pulled a soft blanket over my bare butt. The weight of
the blanket pushed the toothbrush deeper into my tunnel, and it
probed a new spot. I grabbed my cock and started jerking. I
learned that if I wiggled my butt back and forth the plastic
invader twisted and turned and made my whole rear end throb. I
loved the feeling.


I masturbated with a frenzy. The shaft in my butt shifted back
and forth and made my prostate tingle. "Oh shit!" I groaned
softly as my nuts tightened up. I raised my butt and the blanket
tugged at the brush a little more. My dick swelled and suddenly
my cock convulsed, sperm shooting from my dick. Spurt after
spurt, a string of jism shot out. I pulled at my dick and felt my
cum squirt again and again. I grunted a couple of more times as
the warm juice made a mess on my bed, my cock, and my hand. I
finally relaxed and the wet spot on my bed grew cold. I reached
around and gently eased the toothbrush out of my ass. I felt a
little empty when it was gone. "Fucking incredible!" I thought as
I rested. My pucker opened and closed on its own as it adjusted.
Exhausted, I got up, took the towel from the floor and wiped the
cum from my stomach. I dried my cock and took a swipe at the spot
on the bed. I pulled on some warm dry boxers and then my jeans.
"Huh" I thought, "So that's what the little sissy likes so much!"
I gave a quick look toward Trevor's room and finished dressing.


I was out for most of the day and when I got back toward evening
Trevor was in his room. I plopped down in front of the TV and the
door bell rang. "I'll get it!" I heard Trev yell from upstairs
and he ran down and quickly pulled the door open. I saw him grin
as Devon stepped inside. Trevor gave him a quick hug and turned
to look at me. "Devon and I are going to play some video games"
Trev said as he nodded his head toward the stairs. Devon waved at
me and blushed.


As they headed upstairs I thought to myself, "they might be going
to play some games, but I bet it isn't gonna be with a play
station." I absent mindedly looked at the TV for a few more
minutes but couldn't focus. "Fuck this!" I finally grunted and
headed to my room. When I got inside I was kind of drawn to our
connecting bath in the hope that Trevor left the door open and I
could see something. "Shit!" I mumbled, the door was closed and
locked. One of the skills I've learned after almost sixteen years
in the same house and the same room is how to wiggle a card down
between the door frame and the door to get the bathroom door
unlocked.


It took me five minutes but then I had the door open a crack. I
pulled the bath rug over to the door and then lay on my stomach
and peeked inside. Dev and Trevor were standing near the middle
of the room hugging and kissing so intently they hadn't heard a
sound.

I saw Devon pawing at Trev's ass and Trev was grinding his cock
against the front of Devon's jeans. "God I love you" Devon
whispered as he broke the kiss and held my brother close. Trevor
blushed and rested his head on Devon's chest while Devon took one
butt cheek in each hand and pulled Trevor closer.


Trev smiled and rubbed Devon's back. "Where's my girl?" Devon
said softly as he ran his hand through Trevor's hair. Trev
giggled, "Want me to dress up?" He smiled as he looked deeply
into his boy friend's eyes. "Yeah" Devon grinned and gave Trev a
playful spank with one hand. Devon sat down on Trevor's bed while
Trev dug around in his closet. A few minutes later Trev was
sitting at his desk bare assed pulling on a pair of silk panties.
Next he wiggled into a matching bra, and then put a girl's gold
necklace around his neck. As I watched, my brother slowly became
a girl. He walked over to his dresser and after rooting around in
his underwear drawer he found a small gold tube of pink lip
gloss. He stared in the mirror and added this to his look. The
eye shadow and liner weren't far behind. My dick throbbed as my
brother turned into a gorgeous teen beauty. Devon stared with a
huge smile on his face as his boyfriend transformed himself into
a little sissy. "That's more like it" Devon whispered as he
adjusted his cock in his pants.


Moments later Trev was crawling onto the bed. Devon kissed him
and Devon lay back. Trev felt his boyfriend's chest, stroked his
jeans, and cupped Devon's nuts with his hand. Devon grinned as my
sissy little brother worked him over. Trev tugged at Devon's
shirt and within a minute had it off soon followed by his shoes
and socks. With a grin Trevor unbuttoned Devon's pants. Devon
eagerly raised his butt off the bed just long enough so Trev
could pull them down. All that was left was Devon's boxers.
Instead of taking them off however, Trev fished around the piss
hole and pulled out Devon's dick. With a grin Trev turned around
straddled Devon's legs and stuffed his boy friend's cock into his
mouth.


Devon reached up to Trevor's panty covered rear and stroked the
silky underwear. He played with Trev's ass while my brother knelt
over him sucking his dick. I could hear the sound of Trev's mouth
as he slurped and licked at Devon's meat. The whole scene was
making me hornier than I can describe. This went on for maybe ten
minutes and then Devon grunted, "Close Trev". Trev pulled his
mouth off the team quarterback's penis and crawled off Devon's
chest. Going to his drawer again, he pulled out a tube of lube
and grinning slicked up his fingers and reached behind his back.
I could see his fingers slide under the panties and lube his
hole. A moment later he was greasing Devon's shaft. "How do you
want it" Devon whispered while stroking Trev's long hair. Trev
smiled and gave Devon a kiss then squatted over him, one leg on
either side of his chest. "Me on top" Trev giggled. Trevor raised
himself up and pulled his panties down. Without another word he
gently sat down on Devon's cock and grunted as his butt cheeks
opened and his ass hole opened to take inch after inch of his boy
friend's dick. As Devon penetrated his anus and slipped into his
rear end both boys groaned in delight.


Devon thrust his hips upward just as Trev sat down and the last
two inches slammed home. "Fuck that's nice!" Trevor grunted in
happiness as he leaned forward a little hoping to kiss Devon as
he got his ass reamed. Devon grabbed Trev's ass and started
thrusting upwards. Trev rode Devon's cock and his hair flopped
left and right in a swirl. The look of my brother wearing make
up, a bra, and getting butt fucked like a girl was too much. I
reached inside my pants and grabbed my penis. I was so hard I
knew it wouldn't take long for me to cream. There wasn't room for
my hand, so I quickly pulled my pants down over my ass just far
enough to let my dick out.


I lay on the bathroom rug and stroked as Devon and Trevor fucked.
My eyes focused on the spot where Devon's penis entered my
brother's ass. Trev's hole seemed to be wrapped around Devon like
a glove and there was a slurping sound as Devon's dick filled my
brother's rear, pulled out and filled it again. Devon grunted,
"My turn" and let his cock slip out of Trev's ass. He rolled over
and got to his feet. Trev stood and Devon bent him over. Trev
held on to the edge of the bed as Devon pulled his boxers off and
then took him from behind. In one thrust Devon's cock was back
home again up my brother's butt. "Oh fuck yes!" Trev moaned as
Devon must have gone deeper. Since Devon was now in control he
became more aggressive in his thrusts. "I love pussy" Devon
grunted as his hips thrust forward and he hammered Trev's rear
end again and again. Trev's hair flipped from side to side like a
rag doll on the hands of the strong teen football player.


Devon pounded Trev's ass for another five minutes while Trev
jerked his own cock and whimpered. Finally they were both going
to shoot their loads. "Here it comes" Devon groaned as he ground
his dick from side to side and plowed Trev's butt without mercy.
"Do it" Trev panted as he neared his own orgasm. I jerked my cock
faster eyes glued to the hot show in front of me. Devon grunted
and thrust deep one last time. He stood up and Trev was raised up
to his tip toes as Devon impaled him on his cock. "Oh God" Devon
wailed as his hips flexed and he began to pump his cream into my
brother's rear.


Trevor grunted and as he felt the warm injection flood his rectum
and he convulsed, his prick spitting juice. A rope of sperm shot
from Trev's dick, spattered his bed and messed his hand. My own
cock shot at the same time and I clenched my ass cheeks as I shot
my load into the rug. All I could hear was the sound of heavy
breathing, most of it was mine, as my dick softened and we all
came down from our high.


I watched as Devon gently withdrew his cock from my brother's ass
and Trev turned around and they kissed deeply, their dicks
squishing together. Trev whimpered, "That was the best!" and he
gave Devon a warm embrace. "Awesome!" Devon whispered and they
kissed again. "Want a shower?" Trev asked as he played with one
of Devon's nipples. "Sure, sounds like fun" Devon grinned.


Suddenly realizing I was bare ass and cummy on the bathroom rug I
jumped up and quickly tucked myself together. There wasn't time
to clean up so I just threw an old towel from the rack on to the
wet spot on the rug and stood on it for a second. Then I quickly
left the room.


Back in my room with the door safely closed I thought about what
I had just seen. I felt a little guilty about spying on my
brother but it was so fucking hot to watch my best friend take
Trev up the ass. As I heard the shower running, my dick tingled and
started to get hard again. I felt my cock swell and knew that jerking
off wasn't going to do it. I looked around my room in frustration. My
cell sat on my desk. I walked over and picked it up. I punched the
programmed button I had labeled for Michael.


The phone rang. Michael answered, "Hello?" He asked as he picked
up. "Michael, this is Jeremy" I said with the authority of an
upper classman to a freshman. "Yeah?" Michael said. I grinned,
"I'm fucking horny and I need some ass!" I said, not quite sure
what Michael might think. "Tell your mom I'm coming over and when
I get there she should let me in and send me right up to your
room." I could hear Michael's breathing speed up. "Ok" he
whispered. "I want you face down on your bed with your panties
around your knees and your butt waiting to be fucked." It was
quiet for a second and then Michael finally spoke, "Yes sir" he
whispered. I grinned to myself, "Good boy! I'll be right over, oh
and make sure your hole is greased" I said and hung up the phone.


I walked back into our connecting bath and knocked on the door to
Trevor's room. They had finished their shower and were probably
getting dressed. "Devon?" I yelled toward Trevor's room. "Yeah!"
he called back. "Can you give me a ride? I need to see Michael!"
I said. Devon responded a moment later. "Sure Trev and I are just
finishing our game."


I grinned and tried to keep from laughing. "Yeah right" I
thought. "OK" I said turning from the door, "But hurry up,
Michael is waiting for me!" I grinned and stroked my cock.


Like this chapter? Write me at playbuddy123@yahoo.com