Date: Sun, 26 Nov 2006 06:01:15 -0800 (PST)
From: Will Shakespear <playbuddy123@yahoo.com>
Subject: Sissy Brother-20 Revised

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 - 20

I felt like I had been waiting forever for my sixteenth birthday.
Dad had been patient as he helped me practice my driving, but I
was more than ready to get rid of a parent in the seat next to
me. Friday finally arrived and as promised Dad wrote a note that
got me out of school two hours early. That gave me enough time to
get to the DMV and make my appointment for my driver's license
test.


The first part was an eye exam. No problem, I aced it! The second
part was the written exam. The sixty questions are all on a
computer. You can get up to six wrong and still pass. I only got
four wrong so I breezed through that part as well. The behind the
wheel test was the last part and I managed to get a pretty cool
guy that understood I was nervous. He took a couple points off
for parallel parking but gave me a passing grade for the rest.
Dad paid the $90.00 in fees. Yeah, I know they suck, but for a
first time driver I guess its ok. They took the stupid ID photo
and I was done.


Dad congratulated me and let me drive the Lexus home. I knew it
wouldn't happen very often. He already told me to plan on driving
Mom's Camry. As I guessed, we had supper at home and my
grandparents came over for coffee, cake and ice cream. I scored a
couple of hundred bucks in my birthday cards and some decent
clothes. As I fell asleep that night, I thought "Pretty nice
Birthday!" I felt good all over. I propped my new license up on
the bedside table where I could see it, turned out the light and
was asleep almost at once.


Saturday I slept in late. Trevor finally knocked on the door and
woke me up. "Jeremy! I need a ride to Devon's house." He called
out and I woke up at once. "Shit!" I giggled. "I get to drive!" I
jumped out of bed and pulled some jeans over my boxers and
grabbed one of the new shirts grandma had given me. I tucked my
license into my back pocket and grabbed a jacket. Mom could
easily have taken Trevor over to Devon's house but she knew I
would be eager to drive. "Do you mind honey?" she asked as she
held out the keys to her car. "Um, no that's ok" I said trying to
play cool. "Thanks dear" she smiled and we were headed out.


I delivered Trev and then stopped at the store. Mom asked me to
get a few groceries and if it meant I got the car keys it was
fine with me. I got back home about 12:30 I guess. "There are
sandwich things from the deli" Mom hollered as I dropped the keys
on the dining table and headed to the kitchen. I put the
groceries away and made myself a ham sandwich with lettuce and
tomato. Looking at the clock my cock twitched a little as I
remembered my date with Josh.

"Um, Mom?" I said, as I walked into the living room eating the
sandwich and carrying a soda. "Could I borrow the car this
afternoon? I want to meet a friend. I'll be back by supper." I
half asked and half begged. Mom flashed a knowing smile. "Sure
honey!" she said. "But remember, one ticket for bad driving and
you'll see a lot of the inside of your room!" I mumbled, my mouth
full of food, "Thanks Mom, you're the greatest!" and gave her
quick sloppy kiss on the cheek.

I finished my lunch and went to my room to get ready. "What do
you wear when you're going to meet someone to fuck?" I giggled to
myself. I felt the urge in my belly, went to the bathroom,
dropped my drawers and sat on the can. I took a pretty good dump,
cleaned up and flushed. I stripped and took a quick shower. I
paid attention to my dick, balls, and ass. "Earn your clean scout
merit badge" I chuckled as I soaped my cock several times and
washed deep in my crack. I towel dried and then combed my hair. I
used my sports stick deodorant under my arms and threw a little
after shave on my face. "Ok" I shrugged and headed to my room.


As I stood naked looking into my closet I just couldn't decide
what to wear. My stomach felt fluttery and nervous. "Shit! This
is worse than my first date with Jennifer" I mumbled. My eyes
fell on a cool white shirt that I sometimes wore to church. It
had long sleeves and was styled to show off my lean build. I took
a pair of black dress pants off the hook and put those on as
well. I grabbed dress shoes and dark socks, a black belt, and
finally I put on my middle school football ring. I liked the look
of the gold against my hand. "Ready or not!" I shrugged as I made
sure my hair was perfect.


The drive over to Josh's house wasn't long. I was getting more
nervous by the minute and I felt like I had to pee. I parked in
front and taking a deep breath started up the steps. Before I
could knock the door flew open and Josh welcomed me in. "Hey
Jeremy!" He grinned. "I thought maybe you'd change your mind." I
managed a weak smile. "Ah, no it's cool" I mumbled as I looked
around.


I was standing in the entry way of a fucking mansion; well at
least I thought so. As I looked stunned Josh explained. "Well you
know my Dad is a surgeon" Josh said as I stared at the big living
room with baby grand piano, fireplace, and marble topped tables.
"Mom is an attorney. She does corporate stuff for a big chemical
company." I thought, "Shit! Josh is cute, smart, and fucking
rich! How lucky is that?" He continued his little speech, "Its
all a little embarrassing" He mumbled as I finally got my wits
back. "No, it's cool" I said. Josh showed me around the house.
There was a huge kitchen, dining room, and a sun room with lots
of windows and plants. There also was a home theater room with a
plasma screen and surround sound. "Four chairs?" I asked looking
at the theater room. "Yeah, it's me, Mom and Dad and my older
brother. He goes to community college. But he's trying for
Princeton in the fall." I nodded, "Why the fuck not?" I giggled.


We stood quietly for a second. "You look great!" Josh whispered.
I blushed. "Want to see my room?" He asked. "Sure!" I said
feeling my stomach turn again with butterflies. We went up the
stairs and came to a door with a cute gold plated door knocker.
It said, "Joshua" on it. Josh groaned as he saw me checking it
out. "I thought that was really cool when I was 10" Josh said and
his face turned pink. He was so cute when he said that. Inside
was a perfect bedroom, something right out of Martha Stewart.
"Don't you ever make a mess?" I blurted out and then wished I
hadn't said it. Josh giggled. "Yeah, it's usually a real pit in
here" he laughed. "But I knew I was going to have company. So I
worked most of last night and this morning to clean things up."
We both laughed.



Josh put an arm around me and moved me toward the bed. It was a
king size four poster with a massive quilted comforter. He jumped
on and patted the comforter lightly. "Come here" He grinned. I
was so nervous that I really did have to pee now. "Um sure." I
mumbled a little, but "can I use your bathroom first?"


I was embarrassed to ask, but I knew it would be worse if I wet
myself. "Oh sure." Josh said and nodded to a connecting door. I
went inside, unzipped my slacks and pulled my dick out. I was
relieved as I felt the piss leave my bladder and splash into the
designer toilet bowl. As I finished, I shook my dick dry. "Nice!"
Josh whispered and I turned to see him leaning against the
bathroom door staring hungrily at my cock.


My dick shrunk a little in my hand. He walked over and gave me a
hug. He kissed the back of my ear. "Damn, I've wanted that thing
of yours for weeks" He whispered and pushed his crotch against
me. We kissed. I felt his tongue dance in my mouth and he
playfully teased my tongue as we both moaned a little. My dick
started to get harder. Josh kissed me for a bit longer and then
went down to his knees and unbuttoned my pants, and tugged them
down a little. He grinned up at me then took me into his mouth.


"Oh God that's nice" I moaned as I held Josh's head in my hands
and he deep throated my cock. I thrust my hips forward gently and
fucked his face slowly. Josh pawed my ass cheeks and ran his
fingers up and down my crack. "So nice," I moaned as I felt my
dick slide down his warm throat. He pulled his mouth off and
stood up. He grinned and kissed me. "Your pee tastes nice" he
giggled and turned toward his room. I laughed, "That's nasty" I
said, and followed him in.


As I stood in the center of his room, Josh did a slow strip tease
pulling off his shirt, pants, shoes and socks and finally his
boxers. Walking slowly over to his stereo he pushed a button and
soft music began to play. He made sure to show me his ass and
bent over just a little and giggled. In a daze I took off my own
clothes and let them drop to the floor. My super hard cock was
flying out from my belly.


Josh's body is fucking perfect. I can't even describe how perfect
he is. Think of the most incredible picture you have ever scene
of a Greek athlete, young, strong, hung, with a magnificent ass.
That would be Josh. I crawled on the bed and Josh pulled the
comforter back so we could crawl inside toasty and warm. Josh ran
his fingers through my hair. We looked at each other for several
minutes. Then he smiled, "Ready to fuck?" He asked staring me
straight in the eyes. "Yeah!" I whispered, the words sticking in
my dry throat. Josh nodded toward the bedside table. "Top drawer"
he whispered. I rolled over and opened the drawer and quickly saw
the tube of KY. "Get me ready!" Josh said as he turned over and
rested on his tummy.


I squirted some lube onto my fingers and crawled nearer to Josh.
I lay on my side and whispered into his ear as I let my hand make
its way toward his butt. "You ready?" I asked as I spread his
butt cheeks with a couple of fingers and put the greasy ones to
his hole. "Yeah, do it!" He said and grunted a little as the tip
of my finger entered his ass. I slid my finger in deep and
twisted it around greasing every part of his tunnel. Then I put a
second finger alongside the first and both sunk deep into his
rectum. "Fuck yes!" Josh moaned in obvious delight.

I played with his ass for several minutes opening his rear end
and making it ready for my cock. "Now" Josh pleaded and I turned
back to the drawer and lubed up my dick. I crawled over Josh's
back and he raised his ass up without a word from me. I centered
my rock hard dick on his hole.

I pushed forward and my prick popped into his ass easily. I let
my weight settle on his back and my cock sank slowly into his
butt. "Fuck that's nice" I moaned as Josh squeezed my dick with
his ass lips. "Do it!" Josh commanded with a throaty sound filled
with horny passion. I raised myself up a little on my hands like
I was doing a push up. I pulled my cock out and then slammed back
into his hole hard and deep. "Yeah, that's it!" Josh grunted as
he wiggled around on my dick pushing his ass back to take every
thrust. I slammed into him for several minutes that way and then
he grunted, "Wait!"


I pulled out and he rolled over to face me and spread his legs
wide pulling them back to near his ears. "Now!" He grunted and I
crawled over him, lowered my cock and took him like a girl
missionary style. He wrapped his powerful legs around my waist
and pulled his ass up onto my cock. We fucked for ten more
minutes and then he wanted another position. We stood in the
doorway to his room and I got behind him as he held on to the
door frame. I thrust my dick up his ass and he grunted with
delight. "That's it! That's it!" He moaned as I fucked him again
and again.


I was covered in sweat and so was Josh. I pulled out and he
crawled up on the bed doggie style. I got behind him and thrust
back into his hole with my cock. I knew I was about to cum. I
planted my feet on the bed in a squat, and I slammed my dick into
Josh's rear end like we were playing leap frog. "Fuck! Fuck!
Fuck!" Josh grunted as I reamed his hole with all the energy that
I had. He wasn't a timid little sissy boy. This guy craved cock
like a man. His powerful body sucked at my dick with power and
enthusiasm. I felt his ass grip my cock tightly as he tried to
milk me dry. As he squeezed his ass muscles he grunted and moaned
in pleasure. "Gonna Cum!" I grunted as I pounded him hard and he
moaned in delight. "Do it!" Josh whined as he tried to open his
legs wider to give me more of his ass.


I felt the sperm boiling in my nuts and finally the orgasm I had
been working on for half an hour happened. I ground my cock deep
into Josh's bowels and felt the relief of squirt after squirt of
cock juice shooting into his fanny. "Oh God" I moaned as my knees
weakened and I had trouble staying squatted over Josh. My dick
squirted four hard spurts and then I trembled and sagged down
behind the kid. I couldn't keep my dick in his ass any longer and
pulled out flopping onto my back on the bed. Josh fell forward
onto his stomach. "Shit that was nice" Josh finally managed to
say as we caught our breath. "Fucking Awesome!" I whispered,
totally shagged out. We were quiet for a few minutes. Josh
giggled, "So was I the best ass you've ever had?"


I thought for a second, "Not quite" I said raising up on an elbow
to look at Josh. "Taking my brother Trevor's cherry was the
best." I giggled. "But other than that, yeah you win hands down!"
We both laughed. We talked for maybe half an hour cuddled under
the comforter enjoying the afternoon.


Suddenly it occurred to me, "Did you cum?" I asked, embarrassed
to have not thought about that sooner. "No" Josh smiled. "I've
been saving it." I laughed, "Saving it? For what?" Josh turned to
look at me with those deep blue penetrating eyes. "Your ass!" He
smiled. My eyes got wide as saucers, "Oh no" I said moving a
little bit away. "I don't think so!" I was frightened but also a
little excited at the idea. I was also feeling confused with
several conflicting emotions.

Josh leaned close to me and kissed me softly. "Think about it!"
He whispered as he touched my chest and kissed me again. "It
would be the perfect end to a perfect afternoon." We kissed some
more and my cock thickened a little as Josh stroked me. My mind
was in a whirl. I just had the second best sex of my life with an
incredible guy. I knew I was straight and would always want
girls. But, it also felt great being with guys. "Maybe" I
thought, "I'm one of those guys that plays for both teams, Bi."


As I was thinking about all that, Josh continued to kiss me,
stroke my dick, and played with my crack. I was going to protest
but his fingers touching my hole felt nice. When I didn't resist,
Josh stopped kissing me and looked at me again. "I'd never hurt
you" He whispered as he slowly jerked my dick. "But you're pretty
big" I whispered, embarrassed I had even said that much. "I
promise I won't hurt you!" Josh said and kissed me gently again.
I closed my eyes. Part of me wanted to feel what it was like to
get fucked. Part of me however, was still enough of a jock to
know that we didn't do gay stuff. Without another word Josh
gently pushed me over to my side facing away from him. He crawled
over me and I could see his hand reach into the drawer get the
lube. I knew I could stop him; all I had to do was say, "No!" But
I let him go on. Josh crawled behind me and kissed my neck and
ears as he used his lubed fingers to play in my crack.


"Here it comes" Josh whispered as he eased a finger through my
tight pucker and into my rectum. I grunted. "You ok?" He asked as
he held his finger steady but firmly deep in my butt. "Yeah" I
whispered concentrating on the feelings he was creating inside
me. Josh spent maybe half an hour with me on my side. His finger
was in my ass the whole time. He kissed me and slowly fingered me
until my cock was hard again. "You're ready Josh finally
whispered in my ear as he thrust two fingers into my guts.


"Last chance." I thought as Josh reached over me again for the
lube. I heard a squishing sound as he wrapped a greasy hand
around his dick and lubed it from top to bottom. He kicked the
cover off the bed. Lying down on his back he looked at me and
rubbed my shoulder. "You on top" he suggested. "It's easier!" I
gave it one final thought, and then turning looked at the
gorgeous jock lying on his back with his dick standing straight
up. I leaned down and kissed Josh gently. "Stop if I say so!" I
warned. Josh nodded and smiled sweetly.


I straddled Josh's crotch and reaching behind me tucked his hard
cock into my crack. Kneeling, I slowly sat down and felt the head
of Josh's dick push at my hole. "Oh God" I whimpered as I felt
the pain of my tight hole being stretched too far. "Easy" Josh
reassured me and touched my tummy and played with my nips. I rose
up and sat down several times but not quite getting his thick
mushroom head inside. Then, feeling we were close Josh thrust up
and his dick popped inside. "Shit!" I cried out as a sudden pain
shot through my ass. "God that hurts!" I whimpered, "Take it out!
Take the fucker out!" I pleaded. Josh tried to calm me. "Its ok"
he said as he tried to soothe me. "It'll get better" He promised.

We both stayed in the same position. I resisted the urge to pull
off, thinking his big cock head would feel worse coming back out.
A few minutes passed and I was got a little more used to the feel
of his pole in my ass. I warily started to move up and down a
little. The feeling got better as my ass loosened up and Josh's
cock rode more easily into and out of my butt. "That's it" Josh
whispered as I sat on his cock with my eyes closed feeling so
many things at once. He slowly started fucking me and I began to
feel the incredible tingling that a cock makes inside a tight
ass.

We fucked for a few minutes. Then, by accident Josh's cock fell
out of me. He gently rolled me over onto my side and getting
behind me fitted his cock to my hole again. With me lying in a
near fetal position, Josh settled in behind me and entered my
rear end slowly and deeply. My eyes were moist from the earlier
pain of losing my cherry. Now I felt tears rolling down my cheeks
for another reason. "Don't ever stop" I whispered as I felt Josh
fuck me lovingly and in a most gentle way. I had never felt so
loved in my life. I felt Josh's crotch against my butt and his
strong chest against my back. It was perfect. I don't know how
virgins feel on their wedding night, but this had to be pretty
close.

My ass was so tight and Josh had waited so long his nuts were
ready to spill after almost the first thrust. He had been in my
ass maybe ten minutes and simply couldn't hold back any longer.
"Here it comes Jeremy!" Josh whispered as he thrust hard just a
couple of times more and got his cock as deep as he could in my
ass. I felt a stream of juice shoot into my rear, followed by
another and another. Each squirt was hot, sexy, and intimate all
at the same time. Like taking an enema, I felt embarrassed at
what was happening in my rear end but also somehow excited. "Oh
shit, yes!" Josh grunted as he reached orgasm and shot his load.
I felt my butt fill up with cream. Josh stayed up my ass for as
long as he could but soon his dick softened and he slipped out.


Finally, Josh rolled onto his back and I did the same. My hole
was sore and I felt it leak cum onto his sheets. "Thanks Jeremy!"
Josh whispered as he leaned over and we kissed softly. "My ass is
going to be sore for a week and I'll be shitting your cum days."
I giggled. "Sorry!" Josh said with concern on his face. "No, it's
OK" I smiled and ran my fingers through his hair. "This will be
the birthday I'll never forget." We stayed like that cuddled and
naked for a long time. Then Josh leaned close and playing with my
hair whispered in my ear. "Ever thought of letting your hair grow
longer? Like Trevor's?" I thought for a second. "Not really, but
yeah that might be nice." Josh kissed me gently again, "Cool,
that's my girl!" he said.


I made it back home on time. Surprisingly I didn't say much at
supper and was ready for bed early. Josh called and we talked on
the phone for almost an hour. I played with my cock all the time
we chatted. About midnight Trev walked into my room and climbed
into bed with me. "You were pretty quiet tonight!" He said as he
cuddled close to me. "Yeah, I guess so." I mumbled.

"Sup?" Trev asked as he laid a hand on my chest. "I'm not in the
mood for sex tonight Trev!" I said, assuming he was trying to get
me to play. "Not that!" He said a little hurt. "I want to know
what's going on?" I debated about whether or not I should say
anything to my little brother. But as I've told you before, we
don't have many secrets. "I met this guy from school." I said
softly. Trev leaned closer, "And?" I struggled with what to say.
"We kind of hooked up!" I said. Trev was quiet. My heart skipped
a beat. "You can't tell Mom and Dad" I said quickly.


Trev wiggled is fingers on my chest. "That's your stuff" he
finally said as I took a breath. I realized I had stopped
breathing until he answered. "He's really, really nice Trev" I
said gently as I pulled Trev closer. "As nice as Devon is to me?"
Trev asked. "Even nicer!" I grinned. It was quiet again. Trev
giggled, "I wonder what Mom and Dad are going to say when they
find out they have two sissies in the family?"


"I'm fucking going to kill you!" I laughed and started to tickle
my little brother like we did as kids. "Stop, stop" he giggled.
"I'm going to pee!" I stopped and gave Trev a soft kiss on the
lips. "Is it ok with you if I have a boy friend and a
girlfriend?"


Trev thought for a second. Yeah, as long as the girlfriend is
me!" We both laughed and growing quiet, we kissed again. then I
made gentle love to my little brother in a way we had never done
before. "Thanks Jeremy" Trev whispered as he was falling asleep
with the feel of my warm cum in his ass. I pulled him closer and
wrapped him in my arms. "You're welcome, you little sissy" I
said, as I closed my eyes as well.




This is the last chapter in this story. If you enjoyed it, please
write to me at Playbuddy123@yahoo.com


I may have a sequel that will appear in the High School section
of Nifty. The working title is Sissy Brother Goes to Soccer Camp.
It will be a short series with Trevor and Michael. Thanks for
reading.