Date: Sun, 1 Jun 2008 16:46:08 -0700
From: A Scribe <wordspenned@gmail.com>
Subject: Chess Coach

The usual disclaimer applies. Please choose to read something else if it is
illegal to read this story where you happen to be living or if you are
offended by the thought of an older man having sex with a young teenager.
All characters and events are a figment of my imagination and never took
place in the third dimensional reality of this existence. Comments and
politely worded constructive criticism is most welcome. A favorable
response might result in more about the coach's adventures being revealed.
Write to wordspenned@gmail.com.

Chess Coach

There was no longer any need to deny my attraction to the hard slender
forms of the teenage boys that surrounded me during my work day. I thought
if I placed myself in a situation of temptation and resisted I would find
freedom. The experiment fell through when I fell into temptation. Let me
explain how it came to pass that I ended up on my knees staring at three
slender, naked, fully aroused bodies of the school chess team while the
team captain fucked my ass.

Before accepting my new post I worked as a science teacher in a
middle-class, nondescript public school in Colorado Springs. Seeking a
quiet little position where I could work through these new feelings arising
within me. Unfortunately the gods seemed determined to tease me mercilessly
from day one. They brought into my class a fourteen year old who
immediately became the center of my jack off fantasies. Fortunately I
managed to keep my feelings too myself long enough to one day observe him
fucking a cheerleader in the shower.

She was bent over. Bracing herself in the corner as he pounded her from
behind. There I stood watching his tight ass clench and unclench as he
fucked her. I never bothered to clean up the mess I made on the floor
before I walked away. In that moment I realized it was not so much about
fucking him or them as it was about being fucked by them. At least until I
grew to realize that sometimes it was useful to use the one to get the
other.

I went through the motions of life for a week or two until I came across an
online ad for a chess coach at an exclusive boarding school for boys. A
move away from Colorado Springs might help me get a little spark back into
my life. The position was for a chess coach. That was all I would be
doing. More money, board and lodging plus the energy of teenage boys it was
a no-brainer. My credentials as a chess coach were even better than my
teaching qualifications. I had won numerous school titles plus been a state
champion before my sexuality caused me a little too much emotional upheaval
to continue with chess.

A month later I was face-to-face with the school's top four chess players.
They had lost the first two matches and were in need of a confidence
boost. Their first workout with me was in the weight room. A pretty young
personal coach put us all through our paces. Since I worked out daily this
was not a great challenge for me. When we were done she left with the
promise of having our workout routines completed in two days. Looking at
the exhausted chess team I thought it might be two weeks before they
recovered.

The next day I played each of them twice. Despite being fatigued by their
workout the previous day they showed some solid fundamental skills. They
started to complain about meeting Sunday afternoon with the personal
trainer until I reached into a drawer and pulled out a thirteen inch
leather paddle. There is always one idealistic youth who foolishly believes
he is protected by school regulations against corporal punishment. I merely
handed the paddle to the team captain without saying a word and stepped
outside. A few minutes later I heard the first of fifteen blows fall. When
the last blow landed I walked off to my room and jerked off to the image of
me applying the paddle to my chess team one day.

The workout were tough but in my opinion fair. There were regular checks to
monitor progress. I told them there would be no signs of a lack of progress
at any time. Along with the weights there were yoga routines. We all went
through our routines once to get a feel of the different poses.  Susan
would guide each of the guys through their routine in the weight room on
Monday. How wonderful it was to be in a school with money to spare. Parents
of the chess team had told me they would finance any extra expenses I felt
were needed. They had suggested Susan who was a personal trainer for two of
the families.

Our first official chess practice session took place on Tuesday. A day that
would result in me enjoying receiving the entire team's cum in my ass later
in the year. Like most things sexual it began with an innocent incentive
program.

"Before we get to the examples I have for you to work through," I began "I
want to say that I am aware you guys will work harder this year than most
of the others in your classes. This is why I am going to allow you guys to
choose a reward that you will receive if you win your league. Jason, as
captain, you will let me know the team's decision in two days. The team
must be unanimous in their choice. I want it in writing and signed by all
team members."

"Sir, we don't really need two days. We can sign the paper now if you
want." Jason answered.

"Really, how did you know I was going to make this offer?"

"We didn't but we have all pretty much expressed the same wish since you
started here last week. I think it safe to say I can guess what they others
would like as their reward." The grins on their face ought to have warned
me to set a few stipulations. I didn't and they took full advantage.

"What is it you guys would like as a reward?"

"Your ass!" Jason said without hesitation.

"What?"

"You said if we all agreed it would be our reward. We all want to fuck you
and will do so in the order that we play our games. Me, then Tim, then John
and Simon."

"Do you guys mess around with each other?"

"No, we only jack off."

"What do I get if you guys don't win?" I asked while trying to figure a way
out of this mess.

"You get to fuck us in the same order."

"You are all certain you want to go ahead with this as your reward?"
Everybody nodded and smiled.

"I will agree on one condition. Since I have never had anybody fuck my ass
you guys must promise not to let anybody fuck your ass until after league
play has ended. I am assuming you have never been fucked before."

 This was duly noted in the terms of our reward contract, which Jason would
keep locked in his safety deposit box. The guys then surprised me by saying
they wanted a weekly incentive package.

"I'm pretty certain you guys have thought this through and have another
offer to make." I sighed.

"Whoever wins his game will be rewarded by you sucking his cock. Whoever
loses will have to suck your cock. In the event that everybody on the team
wins you will suck us all twice."

Since they had my agreement to let them fuck me in writing I could see no
reason, nor did I really want to decline their offer. What I didn't want
was to appear a pushover.

"I agree if you guys agree to two things. Winners can decide if they want
to be sucked by me or if they want to suck me. I can decide to be sucked by
the loser of a game or to suck him. The other matter is off-the-board
discipline. Failing to keep your grades up; being sent to detention or any
other bad behavior will earn you a paddling in addition to your other
punishment. I get to decide every detail of your paddling."

There were quite a few grumblings about the paddling until I pointed out
that none of them had been in trouble at all for the past three years. I
also pointed out that like the other reward system we had introduced if
they played their part they would have nothing to worry about. Jason was
the first to realize I was not going to budge.

"As long as there is nothing sexual as part of the paddling I'm ok." He
agreed.

"Nothing non-consensual and you have the freedom to ask for or decline any
suggestions. There can be no fucking until the end of the league anyway."

This seemed to satisfy them and everything was duly noted. After an hour we
finally got started on the chess. The guys worked hard that afternoon. We
had two weeks to prepare for the next match and as the days passed I grew
more and more nervous. I had never messed around with any other guys and
was as nervous as a virgin bride on her wedding night. Winning the match
meant I would have to suck at least three cocks. Then I reminded myself
that the guys had never been sucked before so even if I did a below par
performance it will still be incredible for them.

Since they had initiated the sexual aspect into our relationship I felt a
little more secure that they were not going to spill the beans. I visited a
few websites and discovered they all pretty much suggested a similar cock
sucking technique. They also agreed that anything I did was going to make
my partner feel great. Keep the teeth out of the way and all would be fine.

Jason won his game pretty quickly thanks to an error by his opponent that
caused him to resign a dozen moves into the game. Tim and Simon had to
fight hard for their victories. I think the added incentive our team had to
win proved decisive in these two games. John managed a draw, which
according to the decision of the guys meant we both got to decide what we
wanted from each other. I was pretty certain that he would not want to be
the only guy who did not get his sweet cock sucked. Heck, neither did I
want to be that guy so it seemed the ideal result.

On the drive home I set out the schedule for Saturday. Fortunately Jason
was an early riser so he would be getting his blowjob before breakfast was
served. By spacing our encounters a couple of hours apart, with the winners
going first, everybody would be taken care of on Saturday. How quickly
things change, I thought. In one day five guys would have their cocks
sucked by another guy for the very first time. Two of those guys would be
giving their first blowjobs as well. Now that the time for action had
arrived I found myself eager to get started. Resigned to my fate I began to
feel a strange sense of calmness.

Jason let himself into my room promptly at seven the next morning. I
watched him as he stood at the foot of my bed and stripped. We never said a
word the entire time. He was so beautiful and so aroused. I simply lay
beneath the covers as he crawled up over me. His hard four inch cock
traveled straight up to my mouth. He never paused for a moment as he got to
my open mouth. Jason kept approaching me until he was buried to the hilt
inside my mouth and my hands were grasping his smooth ass. He gasped in
disappointment when I released his cock to lick my fingers.

"Trust me," I whispered as I slid a finger down to the entrance of his
ass. "Press down for me." He hesitated and I slapped his but sharply with
my other hand. The unexpected assault caused him to impale himself on my
finger. Never mind Jason, I was in heaven. Sucking cock and probing a
virgin ass with my finger. I nearly came right then.

"Oh fuck! Oh yes, here it comes!" Jason cried out and began fucking my face
faster. Taking advantage of his impending orgasm I buried another finger in
his ass. A quick stroke over his prostate brought him over the edge. He fed
me my first load of sweet boy cream. I savored every drop. We cuddled for a
bit under the covers before we had to shower and dress for breakfast. He
left ahead of me and told me he was certain I would be his favorite coach
ever. I wondered how much of that was as a chess coach and how much was
going to be as a sexual coach. Only time would tell and I was happy to
simply savor this wonderful, new experience.

Tim seemed a little nervous so I suggested we share a drink or two before
getting down to his reward. I believed him when he said he had never had
any hard liquor before so I poured him a gentle rum and coke. After the
second he offered no resistance as I reached over to unbutton his
shorts. Soon I was gazing at his slender, naked body as he sprawled on the
couch with a close up of his cock right in front of me. My breath was
causing it to twitch as I complimented him on how good he looked.

I really wanted to try eating his ass but since Jason had not received this
treatment I did not think it would be fair to offer it to any of the other
guys. I contented myself with the knowledge that I was the first to taste
his cock and probe his ass.

Although we started with Tim sitting on the couch it was not long before I
found myself with the back of my head resting against the couch while Tim
fucked my face like there was no tomorrow. He was at the perfect height
where he could stand in front of me and fuck me. I did not know how much of
his moaning was sex related or drink related. I soon dropped this question
as it became pretty evident he was going to feed me his load.

"Drink it, bitch!" he commanded and emptied himself in a series of powerful
blasts. "Don't waste a drop!" I had not intention of wasting a drop. Being
bossed by a fourteen year old was a huge turn on for me but it was best he
didn't know it.

When I had finished cleaning him I told him if he ever called me his bitch
without my permission I would whip his ass like it had never been whipped
before. To ensure he got the message I gave his ass three hard slaps. He
quickly apologized and after a few lingering kisses we parted on friendly
terms.

Simon had been outside kicking a soccer ball around with his schoolmates
and had come straight to my room. Knowing that I could use a second shower
I did not object too much. He told me he would not arrive for his reward
all sweaty again unless asked. There was no hiding my state of arousal
after my sucking of his two teammates. I simply stripped and stepped into
the shower. Then I watched him finish undressing and kissed him the moment
he joined me in the shower.

After a few minutes of deep kissing I began to kiss my way down to my
prize. I wasted no time toying with his nipples but left a trail of kisses
directly down the center of his body. One of the memories that remain at
the forefront of my mind is the immense enjoyment I derived from fondling
two solid handfuls of ass with a mouthful of cock.  How ironic that I went
from never having tasted cock to sampling the delights of four sweet teens
in one day.

Jason was special because he was my first and so very cute but sex in a
shower remains one of my all-time favorite past times. The warmth of the
water on my back and running down over my naked body as I worked so
diligently on Simon's cock felt so good. He gasped with delight. His
slender hips bucked as new jolts of pleasure spread throughout his body. I
held him firmly in place as his orgasm approach. I sucked harder. I probed
the inside of his ass for that sweet spot. The moment my finger touched it
he exploded.

We soaped each other. We dried each other. We kissed each other good bye
just inside the door to my room. Jason left saying he thought John was a
lucky guy as he was going to be the first to suck my cock. Seems there is
nothing like having your cock sucked to help you overcome shyness.

That evening, after dinner, John and I met to enjoy each other as
dessert. He surprised me by asking me if I was going to ask him to suck me
or was I planning on asking him to let me suck him a second time. I told
him that, like himself, I did not want to be the only guy who never got his
cock sucked this lovely day. Besides, I joked, my mouth was starting to
feel a little worn out. John then told me he would like to blow me before I
sucked him.

I immediately started stripping before he changed his mind. My cock had
never been in such a lengthy state of arousal before. The prospect of
dumping what promised to be quite a load of cum down his virgin throat
almost set me off before he touched me. I picked him up in my arms and
carried him through to my secluded reading area. I kissed his sweet lips
several times before setting him down in from of the bay windows. The
curtains filtered the sunlight and bathed everything in a soft golden
light. I sat down on the bench seat with my legs spread apart. John did not
hesitate to take his place. He did not hesitate to take me into his mouth.

Oh god! There really is no way to describe the pleasure of that first
moment when his lips made contact with my burning flesh. The electric jolt
that ran through me must have been felt by the gods themselves. Sitting
there being pleasured by a fourteen year old who was sucking his first cock
was as good a definition of heaven as I have ever been able to come up with
in my entire life.

I clenched my teeth hard or else my cries would have been heard throughout
the entire school. The orgasm felt as if it would tear me apart from the
inside out. I did crack my head a couple of times on the window as my hips
thrust upwards. When I had finished emptying myself inside of him I slumped
motionless for a minute or two. John had managed to swallow most of my
cum. A little bit trickled from the corner of his mouth. I watched as he
scooped it up with a finger. He offered it to me but I told him I wanted to
taste him. The mischievous smile should have warned me. Before I realized
his intention his cum coated finger was buried up my ass.

We both burst out laughing. I was still laughing when I told him I would
have to spank him for being so naughty.

"Didn't you enjoy it?" he asked.

"Yes, as much as I will enjoy spanking you." I replied.

I had planned on spanking him the next day but he got up from the floor and
laid himself across my knees. I gave him a half dozen playful swats before
the urge to swallow my fourth load of cum took over. His ass would be there
on other days. Instinctively I knew John had a true submissive streak
within him. Perhaps it is because it is so similar to mine that I was able
to recognize it.

Lifting him from my lap I had him stand on the seat. I ran my tongue all
the way from his heavy balls up the underside of his erection. Pulling it
away from his body I let my tongue work its way down the top to the crisp
hair. Then I retraced my path back down to his balls. On the third pass a
squirming John was begging me to take him in my mouth. I thought of
extracting a favor but he had earned his cock sucking with the draw so I
let the head of his cock enter me this time around.

Fortunately John was able to hold onto a cross beam that ran above the
bench seat as he squirmed in my grasp. I was really squeezing his ass
cheeks firmly. I loved the way they clenched and unclenched as I worked him
over. Lost in the play of his ass in my hands his orgasm took me by
surprise.  I was not too surprised to waste any of his cum. Every delicious
drop was savored. I gently lowered him to the seat where he sprawled while
trying to get his breath back. When he felt he had enough strength to stand
I sent him off to the shower.

"Aren't you going to shower?" John asked.

"Yes, after you."

"After me?"

"Yes, after or this," I said pointing to my throbbing cock, "will be buried
up your ass. We promised to keep our virginities until after the chess
league ended. Remember?"

"So you want me or is it any cute ass?"

"Don't you think that if it was any cute ass I wanted I would have simply
paid some kid on the street? There has to be more for me. We may have only
worked together for a few weeks but the four of you are becoming quite
special. That is why we will keep our end of the bargain."

"You're right. I'm sorry for doubting." John said and grinned at me. "That
is worthy of a spanking."

"You don't have to be rude to get a spanking." I told him. "Just ask
nicely."

"Maybe I will."

John headed off to the shower and I jerked off. He noticed the change and
asked if I thought of him when I came. I told him he was naked, soaped up
and bent over in the shower with my cock exploding in his ass when it
exploded in my hand. He smiled, kissed me quickly and walked away.

By now you will have put two and two together and realized we won the
league. Between the first sucking and my first fucking there were numerous
occasions when those same four cocks unloaded in my mouth. There were
spankings for misbehavior but not as many as I had hoped. John made up for
it by asking for some on the side. Although I never got sucked by the guys
after their spanking they did allow me to fuck their ass cracks. I also got
to taste my own cum as I licked them clean.

Jason was giving me everything he had and then some as he claimed my
virginity. All four of them were unanimous in their decision to fuck me one
after the other. I was destined to go to sleep with four loads of cum in my
ass. How tough my life had become since agreeing to be a chess coach for
Addington Boys Preparatory School.

Oh if only the parents could see how their four little angels were behaving
now. Instead they had asked me to chaperone the chess team on an all
expenses paid week at a luxury lakeside cabin. The boys had put forward the
suggestion to their folks after informing me they simply wanted to extend
their reward by a week. After all, they said, it would be cruel to give
them only a single taste of the pleasure to be found in fucking their
coach. They told me if I behaved myself I might find myself rewarded with a
surprise gift. Since it would be odd to turn down an extra week of paid
vacation time I really had no choice. You couldn't possibly think I
accepted because I found the idea of a week long fucking by four horny
teens attractive, could you?