Date: Sun, 22 Jun 2014 19:12:33 -0400
From: Eamonn Bowers <eamonnbowers@gmail.com>
Subject: Goodnight, Rupert

	We had just spent our first Saturday of Summer Vacation at the
Theme Park. We spent the whole day there, almost getting on all the rides;
some of them twice. We even won one of those huge stuffed animals that were
bigger than Rupert and as tall as me. My parents were tired half-way
through the day, but we stayed at the park to keep Rupert happy. He's 11,
and I'm 16. It wasn't until the park closed that he realized the fun was
over and it was time to head home. Once we got settled in the car, Rupert
was already nodding off. My mom was in the passenger seat, fast asleep
within two minutes. Dad turned on the radio to help him stay awake. With
all the things we packed and the prizes we won that day, there wasn't much
room left in the backseat, so Rupert had to sit on my lap.

	I will say that I've always known I was gay, but I wasn't ready to
come out yet. I know my parents would still love me, but I just wasn't
ready for all the drama yet. I was pretty masculine, with my brown buzzcut,
and a soccer player's body. My voice is also quite masculine as well. I
don't think too many people would guess that I'm gay. I will say that I'm
quite sensitive and I'm a very nice guy. And I only play one sport. But
that's all I can think of in terms of what's gay about me, other than
having quite a few female friends.

	My brother kept sliding off my lap. We were both wearing our soccer
shorts and it was very slippery. I was holding him with his head resting on
my left shoulder and his legs on my right side. Kind of like an overgrown
baby. He wasn't very big for his age. To me, he still looked the same as he
did when he was 8, but he must have started going through puberty by now. I
stared at him as the street lamps illuminated his face every few
seconds. He had the palest skin, and the reddest hair of anyone I know,
with a patch of freckles on his nose and shoulders. His lips were so cute
and if his eyes were open, I'd be staring at his round blue eyes, the same
ones I have. I was starting to get hard. I glanced over at my mom who was
still sleeping, and then I tried to reach my crotch so I could adjust it in
a way that Rupert couldn't feel it. I wasn't trying to be perverted, but I
couldn't help it. Thankfully, I adjusted myself and we were home not before
long.

	After we emptied out the car and put everything away, my Dad
carried sleeping Rupert to the couch. It was 11pm and my parents were
deciding if they had enough energy to go to their friends' party that
night. I went upstairs to take a shower. I spent about 20 minutes washing
my body, making sure I was completely clean and shaved in all the right
spots. I liked to be completely smooth down there and I shaved whatever
little hair I had on my behind. After checking myself out in the mirror for
a bit and brushing my teeth, I went back downstairs to see what was going
on. My parents were at the door. My Dad was ready to go and my Mom was
fixing her makeup in the mirror.

"We'll be home pretty late. It depends how fun the party is", my Mom said,
laughing. "Make sure Rupert goes to his bed , but please don't have him up
all night if he wakes up."

I told her it would all be taken care of, and they left in a cab when it
came. I went into the living room and sat down next to my brother and
turned on the T.V. I put on some late night talk show and laughed at a
couple things every now and then. It must have woken up Rupert because I
heard him laugh too. I looked over to see his adorable smile. I asked him
what his favourite part of the day was.

"Playing the games", he said. "Where's all the prizes?", he asked.

"In your room", I told him. "Mom said you shouldn't stay up too late, so
maybe you should go take a bath and get your jammies on".

He did a big stretch and made his way upstairs. I heard the water running
and could hear that he wasn't running a bath, but he was taking a shower. I
flipped through the channels and couldn't find anything good to watch, and
was growing bored. I went up to my room where I kept all my movies and put
one on my T.V. I went back downstairs to get a snack for the movie. When I
got back to my bedroom, I heard Rupert getting out of the shower. He walked
past my room with the towel over his shoulders, shivering.

"Wanna watch a movie with me?", I shouted.

"Okay!", he yelled back. A few moments later he ran into my room wearing
his white and blue cotton pyjamas. I was in a fresh pair of soccer shorts
and my 'Ireland' t-shirt. He jumped up onto my bed and shuffled up against
the headboard next to me. I started the movie, and he rested his back up
against my torso, using me as a backrest. I kissed the top of his head,
which was still wet. I put my arms around him and rested my hands on his
belly. His pyjamas were damp from his wet body.

"You didn't dry off very well", I said, laughing at him.  "Oh well", he
said.

	I was getting hard again, just like I was earlier in the car. This
time, I guess I was being perverted, because I didn't try to hide it. I was
getting kind of horny having him sit like that. I was getting curious to
see if he would say anything. And he did. He tilted his head back and
smiled at me. He sat up and whispered into my ear "You have a boner!"

Suddenly embarrassed, I said "No I don't !" He sat up beside me and hit my
crotch with his hand. It made my penis wag up and down inside my shorts.

"Yes, you do", he said laughing. I gave up and admitted having a boner and
tried to take the focus off of me by telling him he had boner too, but he
wasn't actually hard.

"What! No I don't", and before I could stop him, he shoved down his pyjama
pants and underwear and showed me his soft penis to prove he didn't have a
boner. The way he did that was so startling, but at the same time, so
innocent. I could tell he was just playing around, with no sexual
motive. But I couldn't help but look at his little penis with lust. I
started quickly thinking of ways to prolong this. I had never seen him
naked before, and I had always been curious to see his privates and compare
them to mine. He looked to be about 3.5 inches and his little balls were
pretty tight against his body. His sac was so smooth, with only a couple
blonde hairs. He was intact just like me, and I wondered if he had a tight
foreskin like I did. His penis was clinging to his scrotum from being
squished in his tight boy briefs. My dick was rock hard, stretching out the
silky fabric of my boxers and shorts.

Before it got awkward, I said "Wow, that's pretty big for your age". I
wanted to say something a brother should say in a situation like that. I
didn't want him to know I was sexually attracted to him. He smiled and
asked "Can you pull down your pants and show me yours?" The way he asked so
sheepishly was enough to make me want to grab him and rip all of his
clothes off right there.

"Okay". I lifted my butt of the bed, and took my shorts and boxers all the
way off. I was hoping he would do the same if I did it first, but instead
he let go of the waist of his pants and the elastic snapped back, covering
up his penis. He knelt over just a little bit to get a good look at mine.
I'm about 7 inches hard, with a smooth tight ball sac, and a very tight
foreskin that is very red when I get hard. I can't pull the skin back and
it gives me so much pleasure having the sensitive head so tightly covered
by my foreskin. It's part of the reason I get erections so easily. Rupert
didn't say anything this time. I think he was actually a bit nervous
compared to how he was when he showed me his.

"It's okay, buddy" I said. I swung it around to see if he would laugh. And
he did. He told me it looked like his but way bigger. It was true.

"Well let me see you hard then", I said as nonchalantly as I could. He sat
back and put his legs in the air. He struggled a bit, so I got up on my
knees and helped him out by yanking them off and throwing them behind
me. There he was, laying before me with only his pyjama shirt on. My dick
was pointing straight up at this point. I quickly wiped my precum away with
his pants so that I didn't scare him. He looked up at me and let his legs
dangle outwardly, giving me full access to his penis. He seemed a bit
nervous, but still smiled. I don't think he realized, but his hole was in
view as well. I didn't say anything but I did enjoy the sight of it. His
whole body was blushing, the way your cheeks do when your shy or
embarrassed. His scrotum had a tinge of pink, as well as the tip of his
foreskin and his nipples were red and hard. I could see he had goosebumps.

"Alright, let's see it hard then", I said feeling so perverted. He slowly
reached down and played with his little dick. All he did was move it around
in his hand, kind of the same movement as strumming a guitar. So
innocent. Sometimes I forgot he was 11, his mannerisms are so
childish. Slowly I saw his penis was starting to get a bit plumper and his
foreskin wasn't as loose. It was getting hard. I reached down and caressed
his scrotum ever so gently to see if that would help him get a boner
faster. It was the softest feeling ever. I stopped as he looked up at me,
when a wave of guilt came over me. He was finally completely erect. The
penis was completely parallel to his body as it was so small it couldn't
weigh itself down. His balls were so tight and small, they almost weren't
even there. His penis was probably 4 icnhes long and the width of the base
of my pinky finger. He was mindlessly playing with it; picking it up and
making it point to the ceiling and letting it go, making a light slapping
sound on his pubic area. Every time he made the tip face me, I caught a
glimpse of his head under his tight foreskin. I could tell he had phimosis
as well. The skin was so snug on his head that you could only see a the
tiniest bright red dot on the tip of his stark white boy dick. He had a
hint of pink and blue veins crawling up his shaft if you looked really
close. I wanted him like this forever. I cuddled up beside him and put my
arm oh his belly. He still played with his boner glanced over at mine every
now and then.

"What are you thinking?" I asked him.

"Can I touch yours?", he asked me. I nodded at him and sat up again. I told
him to sit up on his knees like I was and he reached out and gently put his
hand around my hard dick. His touch made it pulse and it gave him kind of a
scare. He laughed a bit and tried to make his penis bob the way I did. I
took my shirt off to show him the rest of my body. I was pretty pale too,
but with no freckles. I had a soft look to me, all my features were
innocent and boyish, but I did have nice abs and a developed chest. I was
quite thin, but not too skinny. His hand cupped my testicles and I could
tell he was probably the most intrigued by the weight of a more developed
ball sac. He didn't say anything, just caressed me and was innocently
curious about his big brother's body. As his hand slid over my hard pink
nipples, I shivered. He was turning me on so much, I had to take this a bit
further. I reached down and fondled his little package before lifting his
shirt over his head and tossing it on the floor. His frame was so delicate
and childish. Everything on him was so undeveloped, like a little boy. His
chest was flat and his belly was so smooth. The smell of his freshly bathed
body was another thing that was driving me crazy. His colouring was
perfect. He was my pink ginger boy. I knew I was in love with him now. And
I could tell he loved me. He trusted me so much that he felt comfortable
showing me all of his most private parts. I caressed him and traced my
fingers so gently over his body that he too shivered and leaned in for a
hug. My dick pressed against his tummy, and I cupped his bum in my one
hand. After enjoying that moment for what seemed like forever, I laid back
against the headboard and invited him to come sit between my legs and rest
his head on my chest. We began watching the movie again, not caring that
we've missed the beginning. I stared down at his crotch which was still
super hard. His foreskin looked really red from being stretched out by his
erection. I wanted to make my baby brother cum.

	I made a bold move and lifted Rupert so that he was sitting up a
bit more, but still leaning his head on my shoulder. I reached down in
front of us and grasped his scrotum between my thumb and fingers. I rubbed
him there to see if I could feel his balls inside of him. They were so tiny
that it made me wonder if mine were ever that small. I don't remember. I
used my index finger and my thumb to hold his little pecker. The stiffness
of his penis was actually impressive and I knew he could shoot pretty
easily in this state. I kissed him on the cheek and said in a nervous but
lustful voice "Can I make you cum?"

He didn't say anything, but scooted in even closer with his legs spread. I
took that as a reluctant 'yes". I took hold of him. I braced him with my
left hand on his torso and my right hand on his stiffy. I held him as close
as possible and I adjusted my penis so that it poked up beneath his
testicles. The hardness of my cock put a lot of pressure on his sensitive
balls and he let out a yelp of pleasure.

I started gently tugging on his foreskin to get him even more aroused. When
the tip became so red that it looked like it might, burst, I then began to
stroke his little shaft between my fingers. He moaned again. I started
humping him through his legs, making my dick rub up against his sac. He was
in pure heaven, making noises I've never heard him make before. He gulped
and grunted quietly as I wanked him. I kissed him on his neck and could
feel heat radiating from his chest as I held him in place. The parts of his
body that blushed had now become so red, it looked like he was might have a
rash, but I knew it was pure arousal. I moved my left hand from his chest,
down to his little pouch and pressed his nuts even more into his body out
of curiousity. He yelped again. I aksed if that hurt and he said no.

"Please play with me", he begged in a whimpering voice. I was still humping
him, making his body writh. I granted his request and continued to roughly
play with his boy balls. I tried fishing them out from within him, but was
unsuccessful. As soon as I got a hold of a ball, I would almost get it into
his sac where it belonged, but it would pop out of my grasp and hide back
inside him. I sped up my tossing action on his winky and I knew it would
cause him to squirt his load if I kept going. I sniffed and kissed at his
neck and whispered nice things into his ear to get him going. He reached
down and took hold of my hooded dick. "Such a good boy, Rupert". "I love
touching you, Buddy", I would say as I got closer to finishing him off.

"I love you, Tommy", he managed to say in a very obviously lustful manner.

"I love you too, Rupert". I tightened my grip on his little prick, which
was completely bulging and swollen by now. I thrust my hips so violently
that he was basically bouncing in the air, so I held him in place again
with my left hand. My dick was rubbing up against his crotch so much that I
was on the verge of cumming. I needed to see him spray. I used all that was
in me to pump his as fast as I could and get this boy to unload. Rupert
began to heave, trying to catch his breathe and verbally notified me that
he was about to ejaculate. He let out one more loud yelp. I could feel his
balls stirring against my penis. I stared down at his cock, still tugging
away. His body went limp before he came and his semen jetted out of his
little pee hole at a million miles per hour. One squirt after the other. He
laid there and grunted with each squirt. He nuzzled me and stretched his
legs in the air as his orgasm came to a close. His dick let out a couple
more little spurts before he took a deep breathe in and sighed.

	It wasn't over yet. I quickly flipped the cummy boy on the bed and
straddled him. Our scrotums gently but firmly pressed against each other's
and i held his still-hard cock in between my finger. I tugged away at my
raging boner and told Rupert I was gonna blast my load all over his
tummy. I lifted up his legs to get another look at that pink hole. He was a
bit confused, but I was too horny to care.  I bent down and gave his ass a
quick sniff and a little lick. I then rubbed his hole for a minute to get a
good feel just to send me over the edge. I put his legs back down, leaned
over him with our balls touching once again. I kissed Rupert all over and
ended up on his lips, making out with him. I looked down at our boners and
couldn't get enough of the site. His tiny little dicklet rubbing against my
big brother dick was too much.  I roared "Rupert, I'm gonna explode!" He
looked really excited to see what was about to happen. He stared right at
the opening of my foreskin. I tugged it back as far as possible to show him
how it comes out of the piss slit, but it wouldn't pull back far
enough. The head was the darkest shade of red I've ever seen before. I
humped his scrotum as hard as I could and let my cum blast out of me. It
made a loud splashing sound as it hit his chin and his chest. I probably
squirted about 10 jets of cum all over my baby brother, the last few spills
landed on his penis and balls. I took his little boner in my mouth as well
as his balls. I gave it one good suck as if to kiss it goodbye. I laid back
down and picked Rupert up to lay on top of me. It was the first good view
of his blushing bum. The cutest one I'd ever seen. I traced my fingers
along his back and his behind, and kissed his short ginger hair. We laid
like that for what seemed like all night.

He fell asleep in this position. I gently carried him to his bed and
dressed him back up in his jammies after wiping him clean with a damp
cloth. He opened his eyes and said in a very soft voice "That was my
favourite part of the day".

"Goodnight, Rupert".