Date: Mon, 29 Aug 2011 07:26:06 -0400
From: Sam Sheppard <samsheppard2011@gmail.com>
Subject: A Ride in the Rain 7

Warning, this story contains explicate content involving sexual activity
between a man and underage boys.

The characters and events of the story are fictional and are not based on
any real person(s) alive or dead.  The author of this story believes that
such events should not take place, but acknowledges that many adults will
enjoy reading them.  As always comments are welcome.

A Ride in the Rain 7

October was almost over, in fact, it was the day before Halloween.  School
had been going well for both boys; they had made some new friends and had
been invited to a Halloween party tomorrow night at their friend Trent's
home.  It was a costume party, with a bit of a twist.  Trent was gay, as
was the entire crowd that would be at the party.  It turned out that there
was a group of kids at the boys' school who had formed a Gay-Straight
Alliance Club and it was this club that was holding the party.  The twist
was that the kids had to come dressed as their favourite historical figure,
real or fictional.  Enoch and Dylan had decided to go as Achilles and
Patroclus.  To make matters worse, they weren't planning to wear any
underwear under their togas.  We'd run around trying to find Greek armour
and had finally located it, complete with helmets, at an out of the way
costume place in the north end of the city.  The boys had a ball, trying on
the costumes, when we got home, and I had called Darlene to come up and see
this.  We were killing ourselves laughing at the antics of our two "Greek
heroes", especially when they were playing Age of Empires while wearing the
armour.  We had dinner and they not only wore their armour (no helmets
allowed at the table) but insisted that Achilles and Patroclus never had
forks and so they were going to eat with their knives and hands only.  It
was a hilarious sight watching these two trying to eat lasagne with no
forks.

After dinner, I insisted that they take off the costumes, so they didn't
get wrecked.  As they were getting changed, the phone rang.  It was Trent's
mom and dad (Peggy and Allan).  Allan had been called out of town for the
next few days and his mom was concerned about trying to handle all the kids
alone.  They were wondering if I'd be willing to be a chaperone at the
party.  I said it would be my pleasure and made arrangements to be there a
half hour early to help get everything set up.  I asked what Trent was
going as and Peggy said he was going as Julius Caesar.  After swearing me
to secrecy she whispered that he refused to wear any underwear and she was
not happy.  I started laughing and explained that Enoch and Dylan weren't
planning on wearing any as well, at which she started chuckling too.  We
said goodbye and I hung up and then told Darlene and the boys that I was
going to be at the party as a chaperone since Trent's dad couldn't be
there.  They all thought that was a great idea.  I made arrangements with
the boys to be ready when I got home from work tomorrow and then Darlene
and Dylan went home.

Enoch had become a very happy, easy going young man over the last two
months.  He'd gotten rid of the Emo look and had cut his hair much shorter.
I thought it made him look even sexier and, more importantly to him, Dylan
loved it.

The next day, I drove home from work, went in and changed into some casual
clothes and then the boys, wearing their armour, and I piled into my car
and drove over to Trent's house in Mount Royal.  We were met by Trent's
mom, Peggy, and taken through to the kitchen, where I met Trent and his
younger brother Troy.  Trent was a cute 15 year old, who looked very much
like his mother, with blonde (short) hair and hazel eyes.  He had a cute
snub nose.  He smiled when he was introduced to me and he had absolutely
perfect white teeth with full lips.  His upper body was concealed by the
toga, but his arms, which were bare, were well defined and when he shook my
hand he had a nice firm grip.  Because of the toga, I could only see the
lower half of his strong, well defined thighs and calves.  I later learned
that Trent was a high level figure skater, with hopes of making the
National team and competing at the Olympics.  Troy was a 12 year old
miniature of Trent and was very excited at being able to stay for the "big
kids'" party.  Trent and the boys drifted off and Troy hung around with
Peggy and me in the kitchen.  He was very helpful, putting out food and
getting things set up for the party.  The kids started to arrive and went
off into the large living room where the furniture had been moved out from
the centre so they could have room to dance if they chose.  The costumes
were quite imaginative.  A pair of girls were dressed like Amazons, there
was a boy was dressed like Robin Hood (in skin tight green leggings, with
an obvious bulge where his jock was and a short tunic), there was a pair of
boys dressed like Bert and Ernie from Sesame Street and quite few more
variations on historical figures.  Troy reappeared and came downstairs
dressed as Cupid, in tight white leggings that showed off his incredibly
tight little bum and his pubescent package under his jock.  I had to keep
very busy to avoid staring at all the teen boy flesh present.  As the night
progressed, the kids ate and drank (pop and juice) and every so often a
pair would drift off to a corner of the room and make out.  And every so
often, one of these pairs would disappear into another part of the house.
I spoke to Peggy about it and she said she wasn't concerned, as it happened
at all the parties the kids attended, but that we should probably check to
make sure everyone was all right every so often.  I was a little surprised,
but what the heck, I thought, it's not like anyone's going to get pregnant.

As the evening wore on, I decided to check in the bedrooms and make sure
nothing serious was going on.  I went upstairs and went to the first closed
bedroom door I found.  I couldn't hear anything, so I opened the door and
found no one in it.  I listened at the next door and thought I heard some
heavy breathing, so this time I opened it slowly and found the "Amazons" in
a sixty-nine with each other on the bed.  I carefully closed it, so as not
to disturb them and moved on to the next closed door.  I again opened it
slowly and discovered a young dark haired boy, of around 13, fucking
another boy, also around 13, from behind.  They were both moaning loudly
enough that I hadn't disturbed them.  I watched for a short while (I
couldn't help it) with the result that my cock was hard in seconds.  I
closed the door without disturbing them and turned around to go down the
hall, running right into Troy, who'd quietly come up behind me.  I asked
him if he'd seen anything and he said no, but that he'd seen his brother
fooling around with one of his friends and knew what was happening.  The
other bedroom door was open, so I decided to head back to the living room
and see how things were going.  Troy followed right along with me,
chattering away about all sorts of things.  When we got downstairs, it
seemed that there were still some kids missing, including Enoch and Dylan,
and I wondered where they could be.  I must have said it aloud, as Troy
indicated he had an idea where some of the kids might have gone.  I asked
him to show me and he took me by the hand and pulled me down the stairs to
the basement, which was fully developed and had 3 more bedrooms, a bathroom
and a family room.  We found two couples, including my boys, in the family
room making out quite heavily, both pairs with their hands in their
partner's crotches.  I checked into the first bedroom and found another
pair of girls going at it and another pair of boys sucking in the second
bedroom.  The third bedroom wasn't in use and, fortunately, neither was the
bathroom.

Troy grabbed my hand again and dragged me out to the back yard, where there
was a large wooden shed.  It had been built by their dad as a playhouse for
the boys when they were younger and now was being used for storage.  I
opened the door and found it was empty.  As I was ready to leave, Troy
looked at me and said, "Wow, you're hard, aren't you?"  I looked down and
sure enough, I was hard and it was very visible in my khakis.

"Yeah," I said, "it happens sometimes."

"Me too," he said, "I've seen Trent's and one of his friend's dicks when
they were hard, but I've never seen one your size.  Can I see yours?"

"I don't think that'd be such a good idea," I said.  Unfortunately, it
wasn't going down and with the thought of possibly fooling around with this
amazing 12 year old kid, it was getting harder.

"I promise I won't tell anyone.  No one'll find out.  I just want to see
it.  Can I?  Please?" he pleaded.

"Look Troy, I'd love nothing more than to let you see and play with my cock
and to play with yours, but it could get me in a world of problems."

"I swear I won't tell anyone."  And as he said that, he pulled down the
leggings and jock he was wearing, allowing his preteen cock to spring up.
As usual, my little head did the thinking for my big head and we moved
farther into the shed and closed the door.  There was enough moonlight
coming in the window that we could see fairly well, so I stood there and
undid my belt and pants and pulled down the front of them.  He stood
staring at my rock hard dick and then suddenly reached out and grasped it
in his little hand.  The feeling was overwhelming and I let out a low moan
as he started slowly jacking me.  I dropped my pants and underwear and
allowed this little Cupid to start stroking me in earnest.  I reached out
and took hold of his penis, which looked to be about 4 – 4.5 inches and
was circumcised and began stroking him.  He had a small wispy patch of
golden hair in a little tuft at the base of his cock and a small scrotum
with a pair of testicles the size of large olives.  Troy suddenly sank down
to his knees and slid his lips over the head of my cock.  I thought about
pulling him off, but it was only a momentary one.  The feeling of this 12
year boy sucking my cock and the danger of it was overwhelming.  Troy
started bobbing his head back and forth, sliding his lips along my hard
shaft and I reached down and held his head, gripping his hair as he fucked
me with his mouth.  He reached up and started playing with my balls and I
could feel myself getting close to cumming.  I stopped him, pulled him up
to standing and knelt down in front of him.  I kissed the tip of his penis,
causing him to gasp and then slid my lips down the entire length of his
hard little spike and began sucking his cock.

"Oh wow, that feels so good. Oh, yeah," he moaned.  I looked up as I sucked
him and he had his eyes closed and his head thrown back.  I slid my lips
off his cock and down his shaft to his little balls in their wrinkled,
hairless sac and licked and sucked each one, as I continued to stroke his
hard little shaft.  I lifted them out of the way and slid my tongue along
the underside of his scrotum and along his perineum, making him moan
louder.  I took the chance and slid my finger up between his ass cheeks and
wiggled it against his little hole, gently probing to see if he'd relax
enough to let my finger in.  He immediately tightened up, but after a short
while, I could feel his clenched pucker start to soften and I continued to
push gently, until with a loud gasp from Troy, my finger slid in to the
first knuckle.

"OH MY GOD," he cried out.  "What are you doing?"

"I hope I'm making you feel good," I said.  "Do you want me to stop?  I
won't do anything you don't want me to."

"Oh god, no!  Don't stop!  I've never felt anything like that.  It's
awesome," he replied excitedly.  I continued to apply pressure on his hole
and wormed my finger deeper into Troy's ass.  Once my finger was completely
in him, I slowly slid it back until just the tip was in him and then pushed
it back as deep as I could, beginning to fuck him with my finger.  As I
did, I went back to sucking his little cock, enjoying the feel of his hard,
fleshy tube sliding over my lips.  I tried to time my sucking with the pace
at which I was fucking his ass with my finger, holding onto his cheek with
the same hand and guiding him back and forth.  I placed the tip of my ring
finger against his hole and on the next push, inserted that as well,
causing Troy to shove his hips forward, driving his cock deep into my
mouth.

"Awww Fucck," he cried, "Oh shit that's good."

"Troy, if you think that feels good, I'd love to try something that I think
will feel even better.  It may hurt at first, but it'll feel sooo much
better quickly.  Are you willing to try it?"

"I think so, but what is it you're going to do?" he replied.

"Remember what we saw those boys doing in the bedroom?" I asked.

"Yeah, they were fucking... Is that what you want to do?  You want to fuck
me?" he asked wide-eyed.

"Troy, I would love to fuck you, but only if you want me to and you're
ready to let me.  If you're not, that's fine, you don't have to.  OK?"

"It looked like they were enjoying it, but I'm afraid it'll hurt," he said.

"I'll take it really slow and if it hurts too much, I'll stop.  How's
that?"  I asked.

"Well...OK, I guess.  You promise you'll stop if I say so."

"Absolutely.  You say the word and I stop."

"OK.  What do I have to do?" he asked.

"You don't have to do a thing.  Just turn around and lean forward against
the wall."

I positioned him with his legs spread and his arms resting on the wall.
Once I had him in position, I got a chance to really look at his behind.
It was like two small whitish globes with the cutest dimples at the sides.
His cheeks were just the right size for me to wrap my hand around each,
which I did immediately.  I knelt down and leaned in and kissed first one
cheek and then the other, then spread them and kissed and licked at his
tight little puckered opening, Troy writhing around as I did.  I slid two
fingers in again as I jacked myself to make sure I was hard enough to enter
him without causing much pain.  When I was ready, I stepped up behind him
and told him I was going to try putting my cock in him and to try to relax
and not tense up.  As I put the tip of my cock against his hole, I could
feel his cheeks and opening tighten so I waited until he relaxed on his own
and then pushed.  There was some resistance and then the tip of the head of
my cock slid in, opening his hold slightly.  I maintained the pressure but
didn't push and he slowly relaxed more, allowing the head to slide past his
sphincter.  I was suddenly in Troy's ass, his tight ring clamped down
behind the head of my cock.

"OH FUCK," he moaned, "that hurt, but it's getting better, now."  He looked
back at me and there were tears in his eyes and a smile on his face.

"Why didn't you tell me to stop?" I asked him.

"Because I didn't want you to.  I've seen Trent and one of his boyfriends
do it and I asked Trent to do it with me, but he won't.  And I was too
embarrassed to ask one of his friends.  So I've wanted someone to fuck me,
but couldn't find anyone."

"Well, I'm glad I'm your first," I said.

I began applying more pressure and felt my cock slide slowly into the
depths of this little boy's rectum.  I held onto his hips as I pushed and
guided as I probed deeper.

"OOWW, OOWW, stop, stop!" he cried and I stopped pushing immediately.

"Do you want me to pull out?" I asked.

"No, it just hurt for a minute.  Just let me get used to it, OK?"

I stayed put until Troy said the pain was gone and then I gently began
pushing my cock deeper into him until I was finally completely buried in
this 12 year olds ass.  His cheeks were pressed up against my pubic hair
and my balls were against the backs of his thighs.  I looked down and the
sight of this young boy impaled on my dick was amazing.  His head was
hanging forward, his golden hair lit by the moonlight, his silky smooth
back arched and leading down to the round fullness of his tight, white ass
cheeks, wrapped around my cock and contrasting with my dark pubic hair.
It's a sight burned into my memory.  I began gently and slowly withdrawing,
his incredibly hot, tight, silky channel gripping my cock as I pulled back,
until just the head was lodged inside him and then pushed my way back into
him until he was totally impaled on my shaft.  I repeated this over and
over, gradually speeding up until I had a nice smooth rhythm going.  As I
did, I reached around his hip and grabbed hold of his hard little penis and
began jacking him as I fucked his ass.

"Oh yeah, Oh yeah, Unnh, Unhip, Oh fuck Troy, you're so fucking tight.  Oh
yeah, baby, oh fuck, oh yeah, oh yeah, oh yeah," I moaned as I fucked this
kid's ass for all I was worth.  Troy was moaning as well and starting to
push back against me as I pushed into him.  My pubic mound made slapping
noises against his tight ass cheeks as we fucked.  The heat and friction of
his hole was too much for me and I was suddenly ready to cum.

"OH FUCK TROY, I'm gonna cum," I grunted. "OH FUCK YEAH, OH, OH, OH, OH,
OHFFFUUUUUUCKK here it comes...unnh, unnh, unnh, unnh, unnh," I cried as
wave after wave of my cum launched into him.  "Ooohhh,
oohhhhfuuucckkk...ooohh shiitt...ooohhh yeeaahhh...ooohhhh holy shit that
was...awesome."

As I blasted into him, Troy's cock began twitching and I could feel the
tube along the underside become engorged.  I increased the pressure of my
hand and the speed and he began spewing his thin cum over my hand and onto
the floor of the shed.  When he was finished cumming, I lifted my hand to
my lips and licked my hand clean.

"Oh fuck Sam," said Troy.  "I've never felt ANYTHING like that.  It was so
intense and I could feel you shooting into me.  It felt so warm."

I slowly pulled out of him and used a rag I found to wipe off my cock and
his ass and then we got dressed.  We'd been gone for more than 15 minutes
and I was concerned that Peggy would be wondering what had happened, but
when we returned she didn't seem to notice a thing.  Before we got in the
house I suggested to Troy that he might want to go the bathroom and sit on
the toilet so none of my cum leaked out and stained his costume.  He smiled
and headed straight to the can.

I headed into the living room to check on everyone and it seemed that most
of the kids had returned, some looking a little worse for wear.  As
midnight approached, we dimmed the lights and turned up the music and some
of the kids were brave enough to dance.  By 1:30 parents began showing up
to pick up kids and by 2:00 the party was done.  I spent the next half an
hour helping Peggy clean up and then it was time to get the boys home.  I
said goodbye to Peggy and Trent, thanked them for inviting Enoch and Dylan,
and was getting ready to leave when suddenly Troy ran over and gave me a
big hug.  I looked at Peggy and she smiled.

"You must have made quite an impression on him," she said, "He only does
that with people he really likes."

"He's a great kid," I said as I ruffled his hair.  "I'm glad Trent let him
stay for the party."  We said our final goodbyes and got into the car.  On
the way home, Enoch suggested that Dylan stay over since it was so late and
I agreed.  When we got home, both boys gave me a goodnight hug, Enoch
kissed me goodnight and we all went to bed.

The next few days were as boringly normal as they could get and then it was
November 3rd, Dylan's birthday.  We all went out for dinner at Chop to
celebrate as we'd planned and then went back to my place for cake and
presents.  Since it was Sunday and the boys had school tomorrow, Dylan had
arranged to stay at our place.  By 11:00 everyone was showing signs of
exhaustion, so Darlene went down to her place and Enoch and Dylan headed
off to their bedroom (it had become "their" bedroom by mutual consent).  As
I was sitting on the couch reading, Enoch came out in his boxers (shit,
this kid looked sexy wearing nothing but boxers) and said Dylan wanted to
know if he could get one of my backrubs.  I said that since it was his
birthday I'd be happy to give him one as a present.  Enoch went back to the
bedroom and I followed in a minute.  Dylan was lying on his stomach on the
bed, naked.  Standing there, I again admired his tight smooth ass.  I sat
down beside him and began rubbing his calf.  I slowly worked my way up his
leg, along his thigh and onto his ass, where I spent some time massaging
each tight cheek.  I then moved up to his back and shoulders and then back
down to his butt.  When I'd finished I had him turn over.  His hard penis
stood proud of his growing bush, but I ignored it for now, concentrating on
finishing the massage.  I worked the muscles of his legs, especially the
insides of his thighs, causing his cock to twitch and then moved on to his
stomach and up to his chest.  Once I was done with his upper body, I moved
down to his abdomen again, concentrating on the area around his cock.
Dylan was moaning and thrashing at this point, so I wrapped my hand around
his throbbing member and began stroking him.  It only took about 5 or 6
strokes before he started cumming, his hot teen cum jetting out of his cock
and landing on his chest and abdomen and then running down over my hand and
pooling in his pubes.  I kept stroking him until he went soft and then got
a warm washcloth and cleaned up his chest, abdomen and cock.  I kissed the
boys goodnight and left.

Enoch and Dylan are now 25.  Both graduated from the University of Calgary,
Enoch from the Faculty of Law and Dylan from the Faculty of Education.
Enoch's working for a large firm downtown and has become successful in the
short time he's been practicing and Dylan's teaching at the same junior
high school they went to.  I retired from the firm last year and spend most
of my time in the Greek Islands, where the water's warm, the weather's hot
and so are the Greek boys.  Enoch and Dylan have moved into what used to be
my bedroom in the condo and when I come back, I stay in what was their
bedroom.  Looking back over the years, I can't believe how much my life
changed, for the better, just because I took a chance and gave a poor stuck
kid a ride in the rain.