Date: Thu, 23 Nov 2006 12:44:03 -0800 (PST)
From: Will Shakespear <playbuddy123@yahoo.com>
Subject: Sissy Brother- 19

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 - 19

Devon dropped me off at Michael's house and it was only a moment
later that Michael's mom let me in. "Hi Jeremy" she said with a
smile and motioned me toward Michael's room. "Michael's expecting
you I think" she nodded toward the other end of the house. "Um,
thanks" I mumbled not wanting to make eye contact with her. I
mean how can you look a mom in the face knowing that you just
ordered her son to strip naked, and wait ass up for you to fuck
him?


I entered Michael's room and found him face down on his bed
wearing a pair of pink girl's panties, They were pulled down to a
spot just under his round butt cheeks. I closed and locked the
door. I smiled as I saw the kid's ass jerk as he heard the sound
of the door latch. I stepped closer loosening my belt and pulling
down my zipper. I pulled the zipper down slowly hoping Michael
could hear the teeth scratch as my pants opened. Michael never
looked back at me, he kept his head buried under a pillow
submissive and obedient. I loved that. I kicked off my shoes,
dropped my pants and underwear and walked up to his bed in white
socks and T shirt.


As I sat down on the bed Michael whimpered a little. I figured
the tension of waiting bare ass naked for me and the boner he had
firmly pressed against his mattress caused the little puppy dog
whine. Without speaking to him, I gently ran my hand up the back
of his right leg and stopped at his ass. His butt cheeked
quivered. My cock firmed up and stood hard. Placing my other hand
on his left cheek I opened his buttocks and saw his pink pucker
tightly closed and wet with lube. I ran my finger up and down the
inside of his crack and he moaned with the feeling. I put my
finger against Michael's anus and press in a little. Then slowly
I shoved it passed the tightly clenched ring and went deep.


Michael's voice was throaty with passion. "Oh God" he moaned and
raised his butt up to take more of my finger inside. "Like that?"
I asked as I twisted my finger in a circle and fucked in and out
a few times. I loved the soft warm feel of his rear end. "Your
ass is mine Michel" I said as I pushed my finger as deep as I
could go into his rectum and rubbed his prostate. He wiggled,
groaned, and clearly enjoyed my finger deep in his secret place.
I pulled my finger out and after giving my cock a stroke, I
climbed on top of Michael. With one knee on either side of his
legs I put my hands on his waist. "Give me your ass baby" I
whispered and pulled his waist upward. Michael raised his butt up
a little. "Good girl!" I smiled as he decided to get on all
fours. I tugged his panties down a little further and nestled the
head of my cock into his crack. I teased his hole with my cock.


I moved my hips forward and applied pressure to Michael's ass
with my dick. The young soccer dude was still tight back there
and I had to work to get inside. "Damn" I puffed as I strained
and finally got the mushroom head of my dick passed his sphincter
and into his boy hole. I slid my cock forward and Michael moaned
with each inch that I put up his butt. "F u c k" Michael
whispered drawing the word out as I penetrated his ass and filled
his bowels with my cock. I pushed in until my pubes were tight
against his cheeks. Looking down at the long haired sissy stuck
on the end of my cock I was as horny as I could ever get.

I slowly began to ride his sissy ass fucking in and out with a
steady pace. I glanced around the room at Michael's soccer
trophies, his kid's stuff from middle school, and all the things
a boy keeps in his room. My dick got harder. "Love fucking
freshman pussy" I grunted as I slammed in a little harder and
heard my nuts slap up against his ass. "Fuck me!" Michael started
to chant as I picked up speed and pounded him again and again.
"Oh God fuck me!" He moaned as my hips thrust forward burying my
cock deep into his butt. I pulled back a little only to thrust in
again. "Fuck you're tight" I grunted as I slammed my dick left
and right to try and widen his hole. Michael's moaning had a
reached a constant whine. I loved the feel of his hot ass hole as
it grabbed my cock.


The submissive little bitch was taking every inch of my dick up
his ass and pleading for more. I pounded his rear end with all
the energy I had. I pulled my cock all the way out and saw a
faint brown stain mixed with the lube. "I'm fucking the shit out
of you Michael" I grunted as I slammed in again.


The sex was great, but it couldn't last, "Gonna cream" I grunted
as I felt the usual tingle in my balls. "Gonna fill your hole
with cum" I groaned and then slammed my cock in and stayed deep.
"Cumming!" I finally grunted as my dick jerked and shot after
shot of sperm flooded into Michael's bottom. I tried to get
deeper as my dick squirted a hot load into the kid's butt. He
groaned and I could feel his hole get tighter. "Uh, Uh, Uh," He
grunted as he had his own orgasm. Without touching himself, the
ass fucking I had been giving him was enough to put him over the
edge and his dick squirted. There was cum all over his bed. We
both grunted as we tried to squeeze the last few drops of sperm
from our dicks and then I pulled out and flopped down on the bed.
Michael collapsed onto his tummy and his heavy breathing told me
he had enjoyed a very good cum.


The room was quiet for several seconds and I climbed over Michael
and gave him a playful slap on his bare ass. "Nice fuck Michael"
I giggled. He turned to look at me, "Thanks" he whispered and he
closed his eyes in a dreamy kind of way. I dressed and headed
downstairs. As I reached the front door Michael's mom called to
me from the living room. "Leaving so soon?" She asked. "Um, yes
Ma'am" I mumbled reaching for the handle. "Michael and I were
working on a project. Actually we were just working really hard
on it and we both finished." Michael's mom grinned. "Well thanks
for coming over and helping Michael" she said turning back to her
magazine. I grinned and opened the door. "My pleasure Ma'am". I
said and smiled as I started my walk home.


The next few days were the usual high school stuff. We had the
usual boring classes, boring homework, and boring family crap to
attend to. Just after supper one night Trevor got permission from
our folks to go to the mall with Devon. I was totally bored and
begged both Devon and Trev to let me come along for the ride and
then they could go be alone or whatever. I bought a sweat shirt
at Old Navy and was walking past the food court when I saw four
guys laughing and having a good time. I started to turn away when
one of them called to me. "Jeremy?" I turned, and Josh stood up
and waved me over.

As I got to the group Josh introduced me to the guys I didn't
know. It took only a couple of minutes to realize these were all
baseball players from last year's team. "Give me a minute guys?"
Josh said as he stood and pulled me away and we sat down at
another table. "Good to see you man!" Josh grinned. "Um, ya me
too" I stumbled, not quite knowing what to say. "Coach Spencer
introduced me to those guys" Josh said nodding in the direction
of the others. They were still laughing and carrying on. "I'm
trying to meet people" Josh offered. "Yeah, I suppose being new
at school, it takes a while" I said nervously.


Josh leaned a little closer. "So, are you thinking about my
offer?" He grinned and gave me a little wink. "Um, well I don't
know" I stammered. I mean it isn't every day that one of the best
looking guys in the whole damn school offers you his ass. Josh
lowered his voice. "Look at them over there" he nodded in the
direction of the other ball players. "They're talking about
pussy, and maybe getting a hand job once and a while" He giggled.
"You fuck ass! I'm giving you a chance to experience something
better than pussy and better than your little sissy brother." I
was surprised at the last statement. "How do you know about me
and my brother?" I whispered leaning in close and glancing at the
other guys. I needed to make sure they weren't listening in.
"Michael lives right next door remember? We talk and well, let's
just say you're not the only one that fucks sissies."


Josh was quiet for a second. "So? You ready for a real man?" he
asked. I looked at the guy in front of me. Perfect blue eyes,
solid chest, chiseled and rock hard abs. He was the kind of guy
that got hired for those fitness machine commercials. My dick
stiffened and I had to move it to one side in my jeans." I
finally made up my mind. "Yeah, I'm ready" I said. Josh grinned.
"Excellent! When?" He whispered.


The fact we were making a date to fuck and we were only a few
feet from the rest of these high school guys made me horny as
hell. "Um" my mind raced, "Friday is my birthday. Dad said I can
get out of school a little early to take my driver's test. We'll
probably have cake and stuff with the family that night. Maybe I
can get them to give me the car Saturday afternoon."


Josh smiled. "Perfect. My Mom and Dad have a once a month
romantic getaway at some Inn upstate. I think they spend all
three days fucking!" Josh giggled. "My brother Brad will be with
his girlfriend. We can meet at my place." I smiled and my cock
was now rock hard. "Okay, after lunch Saturday. I'll call you."
Josh smiled and winked. "It's a date." As we stood I had my back
to the other guys and Josh was facing me. He reached his hand out
and cupped my balls and dick and gave them a gentle squeeze.
Grinning he said, "Keep this hard for me!" and he walked back to
his friends. I covered my crotch with my shopping bag and looked
around hoping no one had seen that. The food court was nearly
deserted. No problem. "Shit!" I said to myself. "What did I just
do?" My dick was so hard it hurt. "Jesus H, Fucking Christ!" I
whispered. A few minutes later I was in the back seat of Devon's
car heading home.

It was about midnight and I was half asleep when Trevor walked
into my room and climbed into bed with me. "What?" I mumbled as
he scooted up close and hugged me. He was naked on top but wore
some baggy sleep pants on the bottom. "Hey" He whispered and
hugged me tight. "I missed my big brother." He said and held me.
I was on my back wearing only my boxers. Trevor laid his head on
my chest and I stroked his hair. We were quiet for a while. "This
is nice" I yawned and turned toward him. "We should do this more
often" He offered and leaned up and gave me a little kiss on the
lips. I felt his hand rest on my crotch and he idly played with
my dick and balls. "Better stop that" I said quietly looking down
at him. "Why?" he grinned looking up. "You're going to make me
horny, and I don't feel like jerking." I said.


Trev continued messing with my cock and balls. "That's okay" He
whispered. "I can help with that." I smiled and then giggled.
"Fucking little sissy" I laughed. "But not my ass" he said
getting a touch more serious. "I'm kinda sore back there." Now I
laughed, "Devon been pounding you pretty hard?" I grinned. Trev
giggled, "Ya, a little" he said. "Tell you what" I offered. "We
can do each other, let's sixty nine!"  Trevor knew I didn't suck
cock very often. "You'd do that?" He smiled. "Ya, for my baby
brother." I smiled and kissed him.


In a few moments Trevor was on all fours over me with his mouth
wrapped around my cock. I pulled his sleep pants down over his
soft butt and his cock dropped down over my face. I licked his
balls and pulled his cock toward my mouth. The angles weren't
exactly the best and it was a challenge to get his cock in my
mouth. It was easier for me to lick his balls and put my tongue
near his hole. "Mmm" Trev groaned as I licked. He had my cock
halfway down his throat and I was raising my ass up to meet his
hungry mouth. This wasn't a hot, cock pounding teen suck fest.
This was a late night gentle game of mutual sucking and pleasure.
I licked my finger and with a lot of spit on it slowly wiggled
into Trev's rear. I remembered that he sore back there so I just
left my finger deep in his butt and didn't move it. I used my
other hand to jerk his cock as I licked his nuts.


I came first shooting my load into Trev's mouth. He sucked and
drank my stuff down swallowing every drop. I jerked his gently as
a moment later he grunted and squirted his load onto my chest. We
finished cumming and then he rolled off me. "Nice load" Trev
whispered as he licked his lips. "You too" I said as I ran a
finger through the pool of sperm on the belly. "Thanks bro" I
whispered as I leaned over and gave Trev a deep kiss. "I think I
can get to sleep now" Trev giggled and kissed me quickly on the
cheek. I looked as he stood and pulled his sleep pants back up
over his firm little freshman ass. "Cute" I thought to myself.
"Very cute!"


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