Date: Tue, 03 Nov 2020 16:01:55 +0000
From: mariopedra <mariopedra@protonmail.com>
Subject: Enjoying teaching Jay Part one

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I always enjoyed attending Boat shows and joining the crowds gathering
around to watch some of the demonstrations. I was in my early thirties at
the time, fit and active and a keen sailor. I had mousy colored short
brown hair, hazel eyes, a good suntan mainly due to much time working
from home where I had a swimming pool on the patio of my old two story
house from which I was able to work from home with my profession in
software development. So I was working for myself.

I enjoyed a few male friends whom I used to invite round to stay and play
games, of which more later.

On the particular day I now remember so well, a crowd had gathered in
front of a new race yacht with foils that was being demonstrated by a
blonde headed young God of the sailing world who was due to set off soon
to round the world searching to break the record time that had stood for
several years.
We were all captivated by him, and packed tightly as we looked up as the
young man on deck explained the workings of his brainchild.

I realized suddenly, and with pleasure, that right next to me had come a
young boy. Longish blonde slightly curly hair, and as he craned up to see
and hear more, his head came almost to my shoulder level. He seemed to
have no objection to my rubbing my hip gently against him so eventually I
got bold and sneaked my hand around to gently brush the front of the thin
blue slacks he was wearing. Still no objections from him as i got bolder,
until finally I could actually feel his cock starting to harden, as so
many young boys will be unable to stop themselves with only the slightest
encouragement!

I looked down at this beautiful boy, who turned his head to look up at me
and I noticed for the first time his wide shining blue eyes. I gave him a
wink to which he responded with a dazzling grin showing  pearly white
teeth, before he shuffled up even closer to me which was fairly
difficult, but went unnoticed in the crowd. then, as I continued my
surreptitious fondling of his now obvious excitement we both stared up at
the young man giving the demo so that no one would notice what was going
on between us!

Finally the demo finished and the crowd started to disperse, and
reluctantly I moved away, but not before looking back to appraise this
simply stunning young lad who I estimated to be about twelve or maybe
thirteen years old. Reluctantly I continued to move away but to my
delight this boy followed, until i was able to find a quiet spot to stop
while he came up to me. I spoke in a whisper as I looked down on his
upturned excited face.
"Boy, if you want a bit of fun follow me outside to my car and we can go
to my house. I have a swimming pool as well as other things that you
might find fun!"
What i did not tell him was that my house was all of twenty minutes away,
and furthermore, which i was beginning to hope might just be of interest
to him, had a secret room much enjoyed by me and my friends for games
that I just wondered if he could maybe be persuaded to join in!!

Once settled in the car and driving away he told me that his name was
Jason, but his friends called him Jay. For my part I told him, mine was
Mario, but for the moment Sir would be appropriate and he seemed okay
with this. As I drove on I let my hand stray to his lap again, and he
shuffled himself in his seat to make it easier for me! He was superbly
and excitedly erect in his light weight slacks and I felt it the right
moment for my next move!
"Do you ever go sailing Jay because obviously you were interested in that
young man's boat?"
"Oh Sir, I would love to learn but I do not have a boat. Do you sail
Sir?"
"I sail a lot in my own small cruising boat, and off and on teach people
the art. What about me teaching you Jay, would you like that?" I waited
for his answer which took only a moment.
"Wow, could I come with you in your boat and learn. How long would it
take Sir?" His large blue eyes stared up at me as his cock pulsed in my
hand!

I went for broke here. "Well Jay, i could give you a beginners course
which would take a week or so, and it would be best if you came to stay a
few nights on the boat and a few at my house for the navigation and
technical skills. Would your parents allow you to do that?"
"I only live with my Mum Sir, and I am sure she would agree. Dad left us
a long time ago and Mum is busy all day at her hotel job so would
probably be quite relieved to be without me for a spell. Sir, when can I
come and how much would it cost?"
"Never mind the cost Jay, I will arrange something with your Mum if she
agrees, and I will be very pleased to have you with me for a week!" as I
said this I gently squeezed his rampant little organ. He was so excited
and apparently so willing!

I decided there and then to press on. My car was a modern saloon with
tinted windows so nice and secure from prying eyes. I knew a good small
pull in and came to rest in it with no other people about. He looked over
at me, again grinning that cheeky smile.
"Take off your shirt Jay, now obey me and look sharp, I will need to
drive on in a moment." He obeyed at once, peeling out of his thin shirt
to reveal his fabulous smooth tanned  young torso!
"Now sit forward Jay, and put your hands behind your back."  As he obeyed
I reached into the glove pocket for my favorite pair of handcuffs I kept
for such occasions.
"Sir, what are you going to do to me?" Then as I started to fix the cuffs
in place on his slender tanned smooth wrists, so obediently and willingly
held ready for me, he asked me, boldly and with no hint of shyness.
"Sir, do you like tying up boys? Are you going to tie me up when we get
to your house?"
But from the grin on his face and the reaction of his young cock I could
tell I had picked a winner and that he wanted to continue. Having secured
his wrists behind him I sat him back, now shirtless and with his hands
secured behind him, but still grinning in that cheeky way at me!
"I get the feeling Jay that you would quite like me to tie you up. Tie
you up properly I mean, maybe naked, before maybe a bit of punishment for
having such naughty thoughts!"
Again that wonderful innocent grin.  "Wow sir, that sounds like fun!"

"Tell me Jay, when are you expected home. I need to know for my planning
with you!"  He looked at me, so cute and desirable and I had sudden
visions of him naked and tied spread and struggling, even maybe  on the
big wooden cross in my dungeon!  But certainly I would at least get him
wearing the brief red shiny speedo that I kept for any boy that I could
seduce to my house.
"I have to be back by six pm Sir or i will be in trouble!" This made me
realize that no one had seen us go, and the boy was only too willing to
play along,

Jay listened as I explained my plans while at this moment my hand was
inside his slacks and feeling his rigid smooth hairless boy cock. It
turned out he he was wearing no underwear!
Arriving at my property I operated the remote on the security gate and
drove over to the garage, then again operating my remote to drive in as
it opened up. Jay looked over at me. "Wow sir, that is real cool." I
ruffled his unruly curly blonde curls.
"I will help you out of the car boy, as at the moment I want to keep your
hands shackled behind you!" Then opening the passenger door I helped him
out getting a thrill of things to come as I felt the silky smoothness of
his bare warm torso and looking down could see the tent of his young cock
still straining in the folds of his thin slacks!
I guided him with my hand behind his head to the doorway through to the
house and he willingly came with me.

I took him to the kitchen realizing that the way to get the boy to settle
was a good lunch, as it was already 2pm and this obviously met with
approval as I tossed two thick beef burgers into a pan, and buttered up a
couple of rolls. I sat Jay on a stool while I cooked and watched him as
he pulled gently at his shackled wrists making his soft body contours
ripple and move in a delightful way.
"Sir, how am I going to eat with my hands like this?" he asked in a
slightly querulous voice. God how I loved a young boy's treble voice as I
came behind him, putting my arms around his slender form and hugging him.
I put my hand again on his obvious erection and he squirmed in pleasure!
"Sir, that feels great. honestly Sir, it is the first time a man has ever
touched me like that!" So I lifted him off the stool and undid his old
fashioned belt buckle, easing his slacks over his rigid boyhood to let
them drop, leaving him delectably naked and exposed! Now I could confirm
that he was uncircumcised and wonderfully aroused with his springy tight
cock standing proud and vertical as only young boys can be!
He wolfed down the beef burger which I held up before him for each bite,
and I followed this with a can of light lager to get him relaxed,  then I
fondled his sexy young hairless smooth body, concentrating on his erect
cock which he made every effort to push forward into my hand, encouraging
me to do more!

"Sir, what time do you think you can get me home because any time after
6pm will get Mum worried!" He waited for my answer as I continued my
fondling.
"Oh I have a plan boy and you must tell me what you think. I am going to
come back and meet your Mum now, and suggest that I pick you up tomorrow
about 10am with some spare clothes for a week long sailing course with
me.
The Boy's reply was a delight and a shock! It was immediately obvious
that he was excited at the prospect of spending a week with me and maybe
of course getting to go sailing. Then, as i took him in my arms and
kissed his forehead he squeaked a reply.
"Wow Sir, what are you going to do with me for a whole week? then again
he asked, Sir, will you be tying me up!?" He wriggled in my arms and
turned his head to look at me. "Will you Sir, will you tie me up and
maybe punish me if i make any mistakes. Will it be like those old films
and be me tied up and, well maybe even whipped?" During all this his
young cock was getting painfully tight so I gave him a few light strokes
with my hand until his whole body went rigid in my arms as he had his
delightful dry orgasm!
Now he went limp in my arms and I carried him to a comfy old chair and
held him on my lap, his naked and tight little bubble butt resting
directly on my own aroused member, which as yet was still within my thin
trousers!

Within a few minutes he was getting hard again as I held him. Oh the joys
of boyhood!  I caressed him as I discussed my plans from here on. Firstly
I had to unshackle his arms and get him dressed so we could go and meet
his Mum and charm her into the suggestion that her boy would benefit and
be safe in my care for a week or so.
I drove us over to meet her at around his 6pm deadline and she seemed to
take to me and be keen on the idea. I explained that I would supply a
life jacket for the sailing sections of the course and that Jay should
come with a spare change of casual clothes, swimming gear, and that he
would ring her each night to report on his welfare and progress. I also
mentioned that if he showed enough promise i would be happy to have him
until the end of his school holidays, and again she seemed happy with
that. I wondered if it had gone through her mind that I might be keen to
have her rather beautiful boy to stay for other reasons, but she happily
agreed anyway!
It was arranged that I would pick up Jay at 9am tomorrow for the first
day in my boat which was moored just up the coast at a small marina. I
returned home elated and planning how soon to get my friends over to join
in with the initiation of this tender young boy into the ways of our
little club, our exclusive bdsm club!

When I got home I went immediately to the dungeon to check on what I
would need for the boy's initiation. No problem with the main props.  The
wooden cross lay propped just above horizontal, ready and waiting for me
and my friends each week when it was our turn to be crucified. Merely
looking at that T cross with the leather cuffs on it's beams and the
pulleys ready for hoisting it upright, the adjustable cuffs to hold the
ankles, made me harden in my pants as I thought of my times struggling on
that cross during our sessions. God it would be unbelievable to have a
willing young boy to take part! To be crucified for our pleasure while we
watched, and indeed for his own eventual pleasure after acceptance of the
obvious pain, when he was finally allowed to come to his well earned
orgasm. I made a note in my mind to show the boy the dungeon as soon as
he got to the house after sailing, to make sure that my vibes were not
fooling me. But remembering his cute wriggling form, naked in my arms
with his hands cuffed behind him earlier in the day, I was sure that I
was on a winner!

I next checked the assortment of genital and penis rings I had collected
for our use. I decided that he was too young for a full three ring
harness and I did not have a set small enough anyway. It would simply be
too difficult to get it to stay in place on his relatively small ball
sack and penis. However the steel ring I chose that would close around
the base of the genitals was fun and infinitely adjustable. Made of two
semi circles of polished steel, 7mm wide, hollow and smoothly curved they
were hinged together at the base while at the top one side slid into the
other to go as tight as required before a small built in locking system
secured them!  I would keep the special key that would unlock them if
required so the boy had no way, other than me, of freeing himself.
My boy would wear this ring for all the time he was with me, his genitals
held tightly and slightly forward, so keeping him even more aware than
usual of his boyhood and his total reliance on pleasing me! The most
embarrassing for him would be was if I made him wear a small speedo on a
populated beach when it greatly enhanced his boy bulge and would attract
the stares of several like minded men!

Finally I put aside a set of 4 cuffs in soft brown leather, and a
matching 3cm slave collar with rings at the sides and front, before
sorting out a selection of butt plugs. Everything from training size, a
very slender shape in black latex rubber that I had saved from my own
boyhood, and which ended in a tapered flanged top for the muscles to grip
and secure. Then a selection of sizes, all the way up to a the full sized
male phallus. I wondered if these would appeal to Jay, because I had to
admit to myself they had never done much for me.
For me, give me a whip, or the cross for a real turn on, with an ultimate
orgasm to finish, but, that was just the way it happened for me,  so each
to his own as they say, and I would be guided to an extent by what young
Jay seemed keen on!
I remembered when I first handcuffed him he had asked if I liked tying up
boys. I had not really replied but I could see that he was certainly very
switched on by the thought!

I prepared a bed for him alongside mine with a rope from each corner post
to secure him spread eagled for the night. I would be able to watch over
him, lust on him, and plan for the arrival of my friends. Two of them
were only too keen to come down to stay for a day or two.
Dan had asked immediately, "How old did you say Mario?" When I confirmed
12yrs he gave a suitable lustful gasp of surprise.
"You try and stop me mate, I am getting hard already at the mere
thought!" Johan's reaction was similar and knowing them both so well I
looked forward to our sessions together.
I would have to make sure that we did not exceed the boy's limits, or put
marks on him that lasted beyond his time with me, because I knew just how
switched on we might get at the sight of this willing youngster
struggling to ride the pain for his ultimate  orgasm!

Morning came and fully aroused after a night of dreaming I showered and
dressed for my planned day afloat. I chose a white leather thong as
underwear, a pair of light weight grey chinos, navy blue teeshirt, and my
old and worn soft leather sailing shoes. The day was hot and sunny as
usual in the south of this country, so no sweater was necessary and I
kept waterproof gear on the boat in all sizes anyway.

After a good breakfast i drove over to his Mum's little apartment
arriving just before 9am. I was greeted by young Jay full of boyish
enthusiasm, wearing, delightfully for me, a pair of thin white cotton
athletic shorts and matching white vest top, bare brown legs with an old
pair of white trainers. He was clutching a small zipped bag of spare
clothes as instructed. His Mum came out to say goodbye and gave him a
hug, while my cock gently grew at the sight of the boy!
"Be good and do as you are told," she admonished him as he climbed into
the passenger seat and buckled up.
His Mum then pulled me to one side for a quick word.
"Mario, he can be a bit wild at times and you have my permission to deal
with him as you see fit!  He really misses his Dad's firm hand and
discipline so no need to let him get away with any disobedience! Oh,
little did she know!

With those final words we were away to the marina to get aboard my boat
for the day. I explained all the workings of my small cruiser which was
my pride and joy. She was fully equipped for four people to spend time
aboard, and I planned to fit a full day's sailing in with Jay, gently
probing him to find out his thoughts and what he would accept later at
the house, at least willingly!
Once clear of the marina he peeled off his vest and looking straight at
me, before grinning and saying.
"Do you like what you see Sir? Do you want to see more!?"
"Carry on boy, no one will see us here!" I muttered as the young lad
peeled off his shorts to reveal what looked like a home made bikini
consisting of two triangles of thin white material that looked like two
white hankies that he had tied on each hip. It was distended in a
gorgeous way by his erection! He stood there grinning, his big blue eyes
watching to see what I would do.

" I think from what I see it will be best if after an hour of tuition we
return to my house for some technical training, and if you continue to
show off that young body of yours, it will probably lead to a punishment
session! How does that sound boy?"
"Exciting Sir, let's get on with the teaching and go back to your place!"
"Just put your shorts back on for now otherwise I will not be able to
concentrate," I leant over to him and took his rigidly boyish member
throbbing into my hand through the thin fabric of his makeshift bikini.
"You boy, are in for a shock or two when we get to my house, and already
you have in fact earned some punishment!" I felt a whole series of urgent
twitches from his cock, before I let him go and he pulled his shorts back
up.

I parked the car on arrival home, and led him in to the main area.
Unlocked the door disguised as a bookcase, and ushered him forward onto
the steps leading down to the dungeon.
"I want you to see what I have here and where I meet my friends boy!" I
flicked on the lights as he looked around in awe and amazement.
Then without any order from me and after a quick look around he walked
boldly over to the cross, peeled off his shirt and slacks, and wearing
only the same makeshift bikini as earlier, he carefully lowered himself
down on his back to the smooth upright of the cross, then spread his arms
along the cross beam!
"Tie me Sir, please show me how you will punish me Sir, please!

If anyone thinks this story of a very willing boy should continue, please
send some encouragement and feedback along with any ideas you may have
for his future! This is what makes it worth writing. Hopefully you
enjoyed some of it anyway, Mario