Simon's Ride Part 3
by Karl 

copyright 2002 by Karl, all rights reserved

* * * * *
This story is intended for ADULTS ONLY.  It contains explicit 
depictions of sexual activity involving minors. If you are not
of  a legal age in your locality to view such material or if
such  material does not appeal to you, do not read further,
and do not  save this story.
* * * * *


For three weeks Lucy insisted that Simon meet her and
her group of girls at the school.  On each occasion he
was stripped and kept naked most of the day and ended
up having a long hard caning by the girls before being
sent home. He was also massaged  several times and
although he would have liked to have resisted he
couldn't and  now looked forward to the girls holding
his young long cock and feeling their fingers
squeezing his cock until he reached ejaculation ,
which was not at the moment very much , but improving
weekly and one of the girls pointed out.   Being sent
home with a red striped bottom was not part of the
pleasures the girls enjoyed . By now they had all
gained some experience in applying the cane to the
boys bare buttocks and even the youngest could lash
his unprotected cheeks with some good effect. 

Lucy , as usual trying to think of something
interesting to do called the boy over to her after one
long Saturday at school . He had just been bathed and
dried and was now only grizzling from his latest taste
of the bamboo stick. 

Next Saturday you  are going over to Clare's house,
you'll go on your bike and when you get there Clare
will give you directions to your next  place . 

Why am I going over there ` he asked and got a smack
on his bare legs for his answer.

Just do as you are told Simon, next Saturday you are
gong to have a ride round the town , you'll like that
 she chuckled and laughed at the nude schoolboy in
front of her.  Just remember that if you make a mess
of it then you'll get a real bad punishment.

Why should I make a mess of it he looked puzzled.
The girls looked on and giggled .
Next week you are going on a ride round the town ,
each girl will give you the directions to the next one
and so on, you'll like it  Lucy grinned  at him as
she ran her hand down his long cock  Now get yourself
home and make sure you do as you are told

During the week  Simon had time to think about
Saturday and what Lucy had in store for him, it would
not be that pleasant if what had already happened to
him was anything to go by.  As usual by Wednesday the
marks on his bottom had nearly gone, the pain
inflicted by the thin cane was intense but the marks
were short lived.  On Friday at school he met Susan
who gave him a package.
You have to wear this when you go over to Clare's
tomorrow, Lucy said so and she walked off . He didn't
get a chance to have a look at it until he got home .
He opened the package and out fell  a  red girls
summer dress with short sleeves and made to hang from
the shoulder. He was amazed at first and then worried,
how could he possibly cycle across the city to Clare
wearing this . When he turned it round there was a
note pinned to the front . Simon - wear this to go to
Clare and do not wear anything else except trainers. .
He was now feeling very worried.  He undressed and
slipped the dress on over his head , it hung down
halfway up his thighs  with nothing to secure it round
his waist.  He looked in the mirror and could see 
that the dress was his size although remarkably short 
 it just covered his bottom , that meant that when he
sat on the saddle the dress would just cover the top
of the saddle and his legs.  The thought of going out
in a girls dress in broad daylight was not  one he
fancied. 

On Saturday as soon as his aunt had gone to work he
changed into his dress and went out into the garage
where he opened the door and  from the inside and got
out his bike and sat on it and found that he would be
just covered if he was careful. He wondered how
careful he could be  and would anyone recognise him .
Taking a deep breath he pushed off and cycled out of
the garage onto the road and off towards Clare's house. 
The effort of cycling and the  wind  blew the dress
back up his legs and nearly exposed his bare bottom on
the saddle.  He made every effort to avoid stopping
any where because he would have to put one foot down
and that would expose his bare legs right up to his
bottom. Luckily he managed to get to Clare's without
incident and he even  felt a bit of a thrill cycling
about in nothing but a girls dress. 

He knocked at the door and Clare opened it followed by
two smaller girls he did not recognise. 
Oh you got here then , come in  you've got to go to
Susan's she pulled the boy in and shut the door the
stood and looked at him which embarrassed him a bit. 
But Clare I was told to come here 
I know but that was only the start Lucy has made up a
game and you have to go round the town visiting the
girls wearing different things and at the end of it we
shall all be waiting for you  and you know what Lucy
is going to do don't you she grinned at him
What is she going to do Clare asked one of the girls

Tell her Simon, these are my sisters
But I don't know what she is gong to do really she
didn't say he looked worried
Oh come on Simon what does Lucy give you every time
before you go home 
Oh you mean that he reddened
Take that dress off Simon and tell the girls what
Lucy does 
What now , what about these two he indicated the
girls about 8 and nine years old who were looking at
him closely wearing a short girls dress. 
Oh come on Simon take it off I wouldn't have thought
that you would have minded by now being nude in front
of the girls . Take it off  she  stepped forward and
caught hold of the hem  Lift your arms up  and as he
did so she pulled the dress off leaving him naked in
front of the girls  his long cock dangling down .
Coo look at that  said the younger girl and pointed
to his uncovered cock Wow  was he going around with
out knickers on Clare asked the other girl
Look at his thing she put out her hand and touched
the boys bare cock . then she caught hold of it in her
fingers It feels funny Clare
let me let me cried the younger one and she pushed
the first girl away to get at the boys now slowly
stiffening cock  gripping it in her fingers and
squeezing it tightly Coo Clare  look at this  Simons
cock got hard and stiff in front of the girls as they
played with it  and this amused them very much Tell
them what Lucy does Simon
The naked boy with the youngest girl holding his hard
cock  tried to get her to leave go but she held on in
spite of his efforts She gives me that cane  he
muttered
What does that mean Clare asked the girl holding his
cock so tightly
You know that Beth replied Clare She punishes him
by caning him , Oh come on you know what that means
Oh right on his bottom 
The nude youngster nodded
Coo Id like to see that when does Lucy give him the
cane Clare asked the other sister
Tonight I think after Simon has completed his little
ride round the town Clare laughed  and rubbed her
hands over his bare backside  Beth either rub his
cock or leave it alone I've got to get him dressed for
his next trip
What do you mean Clare asked the girl still holding
the boys hard cock
Here Ill show you The ten year old reached round
the bare  boy from behind and took hold of his
erection and then griping it tightly she pumped her
hand up and down for a minute and Simon rapidly
reached a climax with a little ejaculation. Beth
watching was not that impressed Can we watch Lucy
cane him tonight Clare, please she appealed to her
older sister
Well Ill see what I can do , now he has to get off 
and she left the room returning with a cotton skirt and
short blouse that would leave the boy s midriff bare.
She wrapped the skirt round his waist and made him put
on the blouse which she did up though it only covered
the top of his chest. It was a typical summers day
outfit for a young girl, but it only just fitted the
boy the skirt only just covered his bare bottom and
his long dangling cock. 
Now you have to go to Susan here is her address c
Clare handed the boy a piece of paper . But Clare
that is right over in the shopping district, I cant
go through there is this can I he wailed  
Oh yes you can and you'd better get started or there
will be penalties to pay  she pushed the boy to the
door and watched while he got on his bike and cycled
off his skirt only  just covering his modesty .  He
spent the rest of the afternoon cycling from place to
another wearing the smallest girls dresses or skirts
that they could expect to get away with ending up
wearing a large T-shirt, obviously a girls with its
front covered in flowers, but not long enough to cover
his bottom completely and in this he arrived at Lucy's
house where all the other girls were already waiting
for him. As he got off his bicycle he spotted Clare's
two sisters and then several other girls appeared
whom he did not know  and who turned out to be sisters
of the original gang . They all trooped off to a hall
at the back of Clare's house  where he and some eight
or nine  girls met up. He was embarrassed and flushed
red and Lucy called him over to her in a loud voice so
that everyone looked round at him crossing the room in
his T-shirt and little else.  The girls all around
Lucy's age though some were younger gathered round the
pair of them and their main topic of conversation was
the near naked schoolboy in their midst.
Is this the boy you were talking about Lucy. He
pretty good looking isn't he and hasn't he got anything
on under that T-shirt  she grinned and the girls
laughed and giggled 
Can we see Lucy asked another voice and there was an
immediate interest in this question,. Several other
girls voiced their opinion and with their giggles and
laughter Lucy caught hold of Simon and pulled him in
front of her

Simon is sort of doing a penance - I read about it 
and if you are doing a penance you have to go round
doing things you don't like and working and such
things and getting punished as well and that is what
Simon is doing , isn't it Simon cos you have been
pretty naughty but we wont tell anyone will we if you
do as you're told she smiled at the boy who stood in
front of her. He was a bit stunned by so many girls
round him and he couldn't keep from feeling some sort
of excitement at the thought of what they might do to
him. 

Several girls asked Lucy questions and they talked
about Simon and how he had been roving round the
neighbourhood in the nude, which made him blush , and
several said that was really naughty which sort of
added to Simons discomfort.

Now Simon is going to get his punishment after doing
his penance riding round the town wearing girls
clothes the girls giggled and laughed at this 

What sort of punishment Lucy, what do you do to him
asked one of them

Tell them Simon, tell the girls what happens next 
she pulled the boy round to face the girls his T-shirt
riding up his thighs nearly exposing his long cock and
bare bottom.

Do I have to Lucy, you are not going to do it here
are you in front of all of them, please Lucy you
never said that Simon was getting a bit worried now 
Tell the girls what happens now and tell them now,
not in fifteen minutes, another headmistresses
saying. The boy dithered and Lucy told him to lift his
arms up which he did although slowly and then she
quickly pulled up his T-shirt and pulled it off
leaving him naked in front of the group of girls which
caused some really loud laughter and gasps followed by
lots of giggles and comments about his long stiffening
cock . Lucy caught hold of his hands to keep them out
of the way so that the girls could have a good look at
his cock and bare behind as well if they wanted to .
The embarrassed boy blushed deeply as he stood there
nude . Lucy nudged him and he told the girls what was
coming next 

Im going to be caned on my bare bottom because I
went round the streets without any thing on and Lucy
caught me he stopped and the girls talked loudly
about the idea of seeing a nude schoolboy get the cane
in front of them.  

 Lucy guided the boy into the middle of the hall and 
told him to bend over and hold his legs so that his
bare bottom was in a good position for the caning. 
Lucy picked up the long thin cane and the girls were
impressed at how slim and flexible it was as she
swished it about and there were plenty of comments
about feeling that across your behind.   With the
girls well placed to see the whole proceeding Lucy 
stepped up to the bending naked schoolboy with his
tight small round cheeks nicely presented for the
bamboo cane to be administered with good effect. Lucy
raised it up and with all her strength she whipped it
across his bare cheeks with a loud crack that startled
the girls and many flinched as the cane cut across the
boys  bare bottom.  The impact of the thin bamboo on
the unprotected bare buttocks of the bending boy  sent
a wave of oohs and ahs through the girls watching and 
many had to bite their lips  as they witnessed that
first stroke which echoed round the room .   Simons
groan and his obvious struggle to keep still added to
their  strain and as the thin red line widened to a
fiery weal they could feel the pain themselves.
However one or two giggled and laughed and that broke
the atmosphere and before Lucy had delivered the second
stroke of the malacca they were chatting and
commenting loudly  about the naked schoolboy being
caned while they watched.  The second cut of the cane
caught the boy across the very middle of his rounded
cheeks which he  was presenting   to Lucy for  her to 
administer his punishment.  He gasped loudly as he
felt the cane bite into his exposed bare bottom and
his tears started to fall onto the floor . The sound
of him crying helped the girls enjoy their themselves 
it made the whole thing more realistic, which for
Simon it certainly was.  

Lucy was a very determined young lady and although she
had never had the chance before she had dreamed of
having a boy she could order about and here  she had
one who would do almost anything she wanted . She
gripped the cane tightly and smiled to herself as she
thrashed the boy across his bare buttocks. The crimson
lines that magically changed to burning weals and
caused the boy  such  scorching pain  were well
deserved as far as she was concerned. He had been
disobedient and got caught so he deserved everything
he got. 

She whipped the cane across his round red striped bare
bottom for the fourth time  making him squeal and
stamp his feet , but he held on to his position hoping
that nothing more would be added to his punishment. 
Lucy could see that the top of his bottom and the
middle were well striped but the lower part was more
difficult to get at so she stopped caning him and told
him to stand up , pointing out that she was not
finished  with him. The girls were now very interested
 and crowded round the naked schoolboy trying to rub
his searing ,smarting behind while he dripped tears
down his face.  His long cock was stiff and hard and
the girls who had not seen him before  quite amazed at
the hardness of it and how they could hold it in their
fingers and feel it throb and  pulse as it as rubbed
up and down until he pushed his hips forward as he
reached his climax. 

The younger girls were very interested in his long
cock and they stood in front of him playing with it
and pulling his foreskin back to expose the top. It
was an opportunity not to be missed the older girls
were more interested in his striped smarting bare
bottom and rubbed their hands over it feeling the long
throbbing weals that were raised over the surface of
his cheeks. 

Lucy got the girls to fetch a table over to the middle
of the room and then the naked schoolboy was made to
lie face down across it. Two girls holding his wrists
and pulling him tightly over it so that his bare under
bottom was exposed to Lucy's cane . Stretched out as
he was he could hardly move as his toes only just
reached the ground. Lucy took up a good position on
his left side and raised the long thin bamboo cane for
the rest of the punishment. Whoosh ,she whipped it
through the air  and cracked it across his unprotected
bare under bottom with a loud snap followed by his cry
 as he felt the bamboo bite into his nude cheeks.  He
struggled and squirmed in the girls grasp as Lucy
raised the cane for the next application of the
malacca to his sore bare behind.  His cries increased 
and his wriggling and dancing about made the girls
laugh . The red stripes were covering his lower bottom
 where he could feel the sting of the bamboo more
effectively.  Lucy caned him twice more each stroke of
the cane applied to his under bottom which made him
squeal and squirm as he lay over the table in the
girls grasp. His tears stained the top of the table
and he shook with  the intense pain of the cane being
applied to his naked buttocks.  To make up the ten
strokes that Lucy intended to give him she shifted her
position and completed his punishment with two hard
cracks of the cane across the tops of his bare legs 
which made him scream out loud at the unexpected
target she had chosen.  

Now the girls let him up his buttocks nicely striped
with deep red weals that seared into his stinging
bottom.  The nude schoolboy stood there in front of
the girls crying loudly and trying to rub his sore 
smarting behind but found it too tender to touch  for
the moment. The younger girls were busy however
playing with his stiff cock jutting out between his
legs and he could not stop them rubbing him until he
reached another climax for their amusement.

The naked boy was now made to stand in a bath of cold
water and be washed all over by two of the girls
wearing long rubber aprons and using scrubbing brushes
which hurt so much when they scrubbed his sore bottom
and used them on his cock and testicles. One of them
held his cock in her hand and the other one scrubbed
between his legs  making him jump about and wriggle in
 as they held on to him. The rest of the girls watched
with grins and smiles as the nude schoolboy was
scrubbed all over and then he had to lay over one
girls lap while she dried and powdered him.  

By this time most of the girls had to go back home and
Simon was eventually left with just Lucy. 
Lucy how am I going to get home from here I havened
got any clothes the boy was worried what she might
say but he needed to know
I've got just he things for you Simon I want you to
wear them home and come over to me tomorrow wearing
them as well.
What are they , Lucy Simon was wary of the girl as
looked at him with his heavily striped bare bottom
carefully rubbing it with both hands.
But first of all I want to try out a couple of
gadgets my brother got from his magazine
Does he buy them Lucy
No, he gets them as free gifts but he doesn't use
them so I thought that we might . Now this one she
held up a shiny metal gadget that had small teeth
round a circle at one end and long handles, like a
pair of very miniature sugar tongs  Goes on your cock
and this one  she held up a hard rubber model of a
boys erect penis  Goes up your bum she laughed 
Right I want you to lay on your back on the table so
that I can get the clip fitted first

But Lucy I don't want that put on my willy, please
Lucy 
Oh stop moaning Simon you'll probably like it any way
its not for you to decide, now get up on the table and
pull you foreskin back so that I can see the top of
your cock 
The nude youngster got up on the table and lay on his
back holding his long cock up and slipping the
foreskin right back so that the girl could see the top
of his cock, she picked up the clip and depressed the
handles and the toothed ring opened so that she could
slide it over the top of the boys cock and releasing
the handles it closed the teeth biting into the
underside of his cock. Ouch, ooh , ouch Lucy it hurts
 
Stop complaining Simon cos you are going to wear it
for a bit. Now pull your foreskin back over the clip ,
go on , get on with it she smacked his bare legs and
watched as the boy eased his foreskin back over the
top of the clip leaving the long handles protruding to
which was fitted a rubber line. 
It hurts Lucy, it really does he complained 
Stop moaning Simon , now get off the table and bend
over so that you bottom is towards me, I want to see
if this rubber cock will go up your bum all right.
she picked up the rubber model and watched as the boy
got off the table and bent over to show her his
heavily striped bare behind.  She went over to the
desk and came back with a small jar of Vaseline and a
pair of rubber gloves which she put on 
Right now Simon put your hands behind you and spread
your cheeks apart so that I can see you little hole
she rubbed some vaseline onto the fingers of one hand
and then as the boy bent over and spread his cheeks
apart she inserted her finger up into his bottom
slipping it right inside him then pulling it out she
picked up the rubber model and smeared it with
vaseline and  then pushed it firmly right up into the
boy where is slipped into place until the flange on the
top stopped it going any further.

Right up you get Simon she ordered the boy and he
stood up tears in his eyes but his long cock stiff and
hard sticking out firmly in front of him. Lucy caught 
hold of it Wow its hard today , how come Simon she
asked the naked boy .I don't know Lucy do I have to
have these things on  he was tearful and although
he could feel the bite of the teeth on his cock and
the cold rubber inserted right into his behind he also
had a sort of excitement that made his cock throb and
pulse as the girls felt it. 

She reached down and picked up the rubber line that
connected to the clip and pulled it for fun making the
 boy jump and then follow her round the room as she
towed him behind her . Right now Simon after I take
this clip off and the other one out of you backside 
you are going home in something  special  which you
have to wear over to the school next week, and
remember Simon next week you will have to put these
gadgets on in front of the other girls  before going
on a tour with them on . You'll like that  she
grinned at the bare boy . Yes Lucy he answered  and
watched as she pulled the cock out of his behind and
then undid the  clip and took it off giving him some
relief from the bite of the teeth.  Then she handed
him a dark blue girls rubber lined mackintosh and a
pair of rubber knickers . Put these on and wear them
home and wear them next week  . He took the clothes
and pulled the rubber knickers  they fitted him very
snugly  with elastic round the waist and legs then he
slipped on the mackintosh and did up the buttons . The
mackintosh came down to his knees the best cover he
had all day. Finally rubber boots complete the
outfit and he got on his bicycle and rode off. 

He spent the whole week in agony trying to decide
whether or not to go  and in the end he had to go,
there did not seem to be much choice so pulling on the
rubber knickers and then the mackintosh and boots  he
cycled up to the school where the Lucy was already
waiting for him and soon the rest of the girls came
in altogether some nine girls , most of them had been
before but here were two newcomers who were giggling a
great deal as they girls slipped the boys mackintosh
off and then after commenting on his blue rubber
knickers pulled them down  leaving the boy naked to
be handled by the girls who soon had his long cock
sticking up and gently squeezed his testicles before
Lucy got them ready for the new toys to be shown. 
Tell the girls what we have and how they work Simon
Do I have to Lucy  though he knew he had to and was
simply delaying the event. Lucy gave him the two
gadgets and he showed them to the girls This one is a
cock clip and it fits over the top of my cock , it
hurts a lot though and this one is a model of boys
cock and it goes up my bum he blushed and shuffled
his feet. 
Right Simon  tell the girls what to do and get them
to fit the clip first Simon gave the clip to one of
the girls and lay down on the table his cock now loose
and floppy 
Open the clip by pressing on the prongs  The girls did
this and they could clearly see the teeth  which
caused some comments Now pull my foreskin down so
that you can see the top of my cock the boy directed
Susan who holding his cock in one hand slid his
foreskin right down with the other 
Now slip the clip over the top of my cock and gently
release the prongs so that the clip grips my cock
tightly he ooh and ahed as the girls pulled his
foreskin back and the clip was pushed over the head of
his cock and the spring released to bite into his cock
just below the head  Now pull my foreskin back up 
over the clip one of the girls did this until his
foreskin covered the clip
Coo doesn't that hurt you Simon
Yes it does but Lucy wants me to wear it and now you
have to put on rubber gloves and get the Vaseline. Now
one of you hold me cheeks apart and one of you put
some vaseline round my hole and slip your finger right
up inside then grease the model rubber cock and
insert it right up, that's it push it right up , Ok?

The naked schoolboy now got off the table and stood in
the midst of the girls his bottom plug in and his cock
clip on. Are you going to punish him today Lucy asked
one of the girls
Oh of course we are cos little boy s need to be
punished regularly don't they Simon she looked at the
boy  who blushed and looked down 
I suppose so  he muttered.
Have you ben good all the week Simon teased Susan
Well mostly I have tried , I havened done anything
wrong really I havened the boy was only to aware of
the consequences
Lucy caught hold of the rubber band that connected to
his cock clip and pulled it gently so that the boy  had
to follow she pulled him into the middle of the hall 
he followed with a pained expression on his face  It
hurts Lucy, please don't pull it so hard.  he was
watched eagerly by the other girls  the two new ones
whispering with each other as they looked at the nude
youngster. 
What do we give naughty boys Simon asked Lucy
grinning Tell us what a really naughty boy should get
 she tugged on his line
Well I expect he should get the cane , I suppose  he
stopped and looked at the girls who were giggling and
grinning at him
Ah the cane Simon and how many strokes of the cane
should a really naughty boy get then she was teasing
the  bare boy


  
SR3_Simons_Ride_3