textfiles/sex/EROTICA/C/costumed.txt
2021-04-15 13:31:59 -05:00

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COSTUMED CAPERS
Part 1 of 5
The full length mirror reflected the image of a young
girl dressed in a frilly pink party dress with white lace
trimming the bodice. Smooth bare shoulders were caressed by
the long strawberry blond hair and firm breasts pressed into
the fragile fabric. A white satin ribbon circled the waist
below the darts of the dress just above the flare of the
somewhat short skirt held outward by six layers of crinoline
petticoats. The legs were smooth, pale, long and slender and
the feet were small and adorned by little white lace ankle
socks and black patent leather shoes with one inch heals. The
face was beautiful with bright blue eyes and a slender nose
and perfect teeth. The hair cascaded over the thin shoulders
from just behind the white ribbon which held it back from the
face where the pouting lips were coated with a pink lipstick
matching the dress. Jimmy could stand it no longer and
gently reached under the skirt and slowly inserted his
trembling fingers under the waistband of the smooth nylon
panties. As his fingers traveled downward they passed over
hairless skin as smooth as a baby's and finally traced over
his rapidly growing cock! He stroked his small member and
smooth balls as he looked at the lovely vision in the mirror
and dreamed of someone else's fingers manipulating the center
of his sex. "Aghaa..., Aghaa!" He cried as each touch of the
small hand sent shockwaves throughout his body, his hips moved
in synchronization with his hand and at last his body con-
vulsed. "Oh, oh, god!" he groaned as his juice soiled the
inside of the wonderful panties and covered his hand.
The sixteen year old collapsed on the floor in front of
the mirror with exhaustion from this powerful climax and was
sprawled out with his hand still in his panties when he fell
asleep. The sound of keys in a lock and voices echoed in the
large room under the stage as Jimmy awoke in a daze. The
click of heels on the hard cement floor approaching drove his
mind to a state of full alert and a realization of where he
was and how he was dressed. "Oh shit!" he breathed to himself
as he scrambled from the floor and looked for a place to hide;
there was a cubby-hole behind the massive wardrobes and he
quickly forced his body into it and out of sight, just as the
door opened.
"Somebody left the light on again," said one of the
voices as what sounded like three or four of the costume
committee entered the room. "Yeah, I'm sure glad it was us
who found it and not Miss Hall," answered another, "She gets
mad when we don't put things away or leave the lights on."
The girls moved about the room, putting things away and re-
arranging some of the costumes for about 45 minutes, while
Jimmy listened from his hideout and tried not to breath, less
he make a sound. "Hey, Suzie put some boy's costumes in here
again, damn it, when will she ever learn that they go in the
other room!" "Well she's only a dumb freshman; just gather
them up and take them over to the other room and I'll clean
them tomorrow," came a reply. "Well, that's all we have to do
in here," said a voice, "Let's lockup and get to class before
we're late again." Following, mumbled assents from the
others, the footsteps headed towards the other end of the room
and the only door in or out of the storage space. The lights
were turned off and Jimmy heard the door close with a bang as
the lock mechanism set.
"God! that was close," he said to himself as he once
again allowed himself to take a breath. The room was as dark
as a cave with the only light being provided by a small exit
sign above the door at the far end. Slowly Jimmy worked his
way out of his hiding place, carefully listening for any sound
that the girls might be coming back and slowly felt his way
towards the door. The petticoats rustled as he moved and his
heels clicked on the cement floor as he inched his was through
the many racks of clothing between him and the door. When he
finally reached it, it took several attempts before he found
the light switch and when the lights came on they almost
blinded him. "I've got to get out of here!" he said to
himself, "That was too fucking close!" Immediately, he walked
back to the other end of the room where he had left his
clothes, unzipping the dress as he walked. As his eyes
scanned the area, he suddenly stopped dead in his tracks. "Oh
shit!" he exclaimed as he realized his clothes were missing.
"They took MY CLOTHES," he said, remembering the discussion of
the "boy's costume" the girls had removed. Jimmy was is
shock, his pants had contained his keys both for school and
home, as well as his car, and his billfold containing his
school ID and driver's license. "What if they find my
billfold?" he thought and before he could answer his own
question, "They locked them up in the other room, How am I
going to get home? What am I going to WEAR? How will I get
in the house? They've got my keys!" The rapid fire realiza-
tion of his situation was more than he could take and as his
body shook with fear, tears began running down his trembling
cheeks as his body shuttered.
Jimmy sat for quite a while before he decided that his
only option was to wear SOMETHING from the costume room and
make his way home (almost 5 miles) on foot. He would then
have to figure out a way to get into the house, change
clothes, get his extra car keys, return and get his car;
hopefully before his parents got home. Looking around the
room, 90% of the clothing was clearly unsuitable, either due
to size or type. Much of the costume clothing fell into the
categories of "period" or was to depict medieval, oriental,
1950's or other "non-street" clothing. As he quickly went
through rack after rack of clothing, not one pair of pants of
any type could be found, only dresses, skirts, blouses, gowns
and "special" costumes. It quickly became apparent that he
would have to leave the school dressed as a girl! Shortly
thereafter, he found a school uniform which appeared to be
from the private school about 2 miles down the road from his
public high school. It consisted of a white long sleeve
cotton blouse with lace collar and cuffs and a green and black
plaid jumper style skirt. Jimmy had seen many girls from the
private school wearing this outfit and knew what accessories
he needed. Digging through storage drawers he soon found a
pair of white pantyhose, a black purse and a pair of black
patent leather "mary-jane" style flats. Stripping, he tried
on the blouse and immediately took it back off when he
discovered his nipples were visible through the thin cotton
fabric, then searched some more drawers until he found a bra
with small cups and a white camisole with matching half-slip.
Jimmy had trouble hooking the bra behind him so he hooked
it in front then turned it around and put his arms through the
shoulder straps as he pulled it up his body. To his surprise,
the padded bra actually made it look as though he had breasts!
Next came the camisole and slip followed by the pantyhose.
Jimmy struggled for at least 20 minutes trying to get the
pantyhose on and pulled so that the crotch was were it was
supposed to be. Again he tried the white blouse and this time
only the lines of normal girl's underclothing was visible
through the fabric. Next came the jumper and last the shoes
which felt very light compared to the weight of his normal
boy's shoes.
This time when he looked in the mirror, Jimmy saw a
beautiful young school girl and other than a few touch-ups of
makeup, knew that he could pass in public as a girl if he was
careful and avoided people he knew. With the long wig and
girl's clothes, he looked more like his older sister than
himself and thought he just might be able to get out of this
alright. Retying the ribbon in his hair to form a ponytail,
Jimmy then searched the cosmetic drawers until he found a
light red lipstick to replace the pink and some rouge which he
lightly applied to his cheeks to give them a soft rosy glow.
He also found a couple of nail files which he dropped in the
purse along with a handkerchief and the cosmetics he had used,
thinking they might be useful in breaking into his parents
house. Moving to the door, he pressed his ear against it
listening for any indication of someone in the hallway
outside, hearing none, he took a deep breath, opened the door,
turned off the light, and after closing the door dashed up the
stairs and out the fire escape door behind the stage. He was
now outside, with no way to go back or change his mind. He
had to make it home!
Fortunately for him the emergency exit door let him out
on a side of the building with no windows, and he immediately
crossed the open grass to the area of the maintenance build-
ing. Looking over the window ledge into the office of the
maintenance building he could see that it was 1:30 p.m. so he
had plenty of time to make it home and back before his parents
got home at 6:00. Staying below the windows, he moved along
the building and then darted behind the parked school buses,
crossing through some evergreens along the edge of the parking
lot and onto the right-of-way for the railroad tracks which
passed behind the school and headed towards the housing
development where he lived. Jimmy moved quickly along the
tracks staying on the far side of the railroad grade so that
he would not be visible from the school. Soon he was at a
point where he could no longer see the school building and
slowed his pace as he continued to walk towards home, still 4
miles ahead.
The tracks curved away from the road on which his school
was located and before long he entered a section where it was
wooded on both sides of the tracks. Jimmy almost skipped as
he passed through this area, elated at his good luck in
escaping the school undetected. He was so happy, he didn't
notice his surroundings until suddenly a boy appeared on the
tracks ahead of him only 20 feet away. Jimmy stopped and
noticed the boy was standing astride the center of the tracks
with hands on hips, feet wide and a big grin on his face.
From his dress, Jimmy knew he was a student at the private
school and suddenly he began to feel very uneasy about the
smirking grin and penetrating look the boy was giving him. He
turned to run, but immediately stopped again, because as he
wheeled around he was confronted by three more boys behind
him! All four boys were bigger than he was and he was
surrounded.
"Well, well, what DO we have here," said one of the boys.
"Must be a new girl," observed another, "I've never seen her
before...kind of cute though!" "Cute my ass, SHE's GORGEOUS!"
said a third who was the biggest of the lot, standing about 6-
5 and huge, well over 225 pounds. "Hi... Hi guys," Jimmy
studdered, "I, I see you skipped out of school too." Jimmy
offered with a grin, hoping humor might get him out of this
situation. "What's your name?" came the question from behind
him, from the original boy who looked to be about 5-10 and
slim built. "Ji.., Jenny," Jimmy replied as sweat suddenly
formed on his forehead and his mouth became very dry. "Jenny,
uh, pretty name for a pretty girl, I'd say, by the way, my
name's Bob," said the giant. "That's Joe, and he's Eddie, and
the guy behind you is Tom," Bob said as he smiled down at
Jimmy. "We couldn't take any more, so we decided to take the
afternoon off," Bob offered, "How about you?" "I... I felt
sick," Jimmy said as his mind raced trying to think of
something the boys would buy as a plausible excuse, "so... so
they let me go home to ... to rest," he finished. The boys
were now tightly surrounding him and there was no possible
escape without their consent Jimmy realized, so he hoped he
could still talk his way out without them finding out he was
a boy. Because IF they found out, he knew he was DEAD MEAT!
Suddenly Tom's hand was on Jimmy's shoulder from behind and
Jimmy froze in panic. The boys made small talk giving each
other sideways glances and smirks which Jimmy recognized as
pure SEX signals concerning their trapped quarry. Meanwhile,
Tom's hand was stroking Jimmy's shoulder and upper arm while
Jimmy noted that Joe and Eddie had moved to either side of him
and Joe was pressing his crotch against the back of Jimmy's
left hand. Joe was now towering in front of the frail 5-5 boy
and looking down with a grin said, "Well now Jenny, we think
we like you, but we would sure like you a lot more if you
might help us out a little."
"What... What do you mean?" Jimmy stammered, knowing
exactly what they had in mind, but hoping he was wrong. "You
know, little cutie," Bob said as he traced Jimmy's jaw line
with his fingertip, "we got to get a little sex every now and
then or us boys go crazy." "But... But, I'm sick," cried
Jimmy hoping they still might let him go, "I... I'm having my
period and I've, I've got real bad cramps," he offered,
praying they would buy it. To his shock, Jimmy felt Tom's
hand on his ass, massaging the cheeks like he was kneading
dough or something and made mental note to make sure they
stayed on the back side! Without warning, Joe bent forward
and kissed Jimmy on the lips forcing his tongue deep into
Jimmy's mouth as he held him by the shoulders. "What I have
in mind," said Joe after breaking off the kiss, "won't be
affected by you period baby." "But, I've got the flu or
something too," cried Jimmy hoping to avoid any more kisses or
god forbid other oral activities. "I don't want to make you
guys sick." "Well how about a hand-job?" Eddie suggested and
before Jimmy could reply, Jimmy heard the sound of four
zippers opening in unison. Tom was now pressing tightly
against Jimmy's back and he could feel the press of a hard
cock right in the crack of his ass, while the boy moved it up
and down against the fabric of his jumper. "Ok, Ok but give
me some room, and, and no touching me while I do it, UNDER-
STOOD!" taking an assertive approach in hopes that would
prevent discovery since they were going to get relief. "OK,
You got it baby, Oh yeah" were the replies and immediately Joe
and Tom backed up to give her room.
Eddie and Bob were now on his left and right and Jimmy
took a deep breath before looking down towards the hard-ons he
knew were at his sides since he could feel them against the
backs of his hands. While looking at Bob, he moved his right
hand to encircle Eddie's cock and found it to be relatively
small but very hard and twitching with anticipation. He
slowly pulled Eddie's manhood gripping tightly then reached
underneath and rolled the boy's balls between his fingers,
which drew a loud moan from the boy. Meanwhile he looked down
at Bob's member and was amazed at the size of it; IT WAS HUGE!
Like it's owner, it was above average in size, a good 10 or 11
inches long and 2 1/2 - 3 inches in diameter. Jimmy had never
seen a cock this big and was now eager to explore it and the
giant balls hanging below it. While he stroked Eddie, he
gently poked and prodded Bob's groin, marveling at the smooth,
silky skin and firmness of the huge dick in his hand. Bob
just smiled and murmured encouragement. Soon Jimmy was
working both cocks, stroking back and forth with all his
strength. After about 15 strokes, Eddie came hard, spraying
cum all or Jimmy's skirt. He was quickly replaced by Tom who
forced his eager cock into Jimmy's hand and started thrusting
his hips back and forth through the warm hand. Bob also
thrust at Jimmy's hand, but his strokes were long and slow,
savoring every stroke. Bob finally came and Jimmy could not
believe the amount of cum sprayed from the giant cock.
Immediately, Joe's average sized cock filled his left hand and
like Tom he quickly pumped back and forth, too far gone to
wait very long for a climax. Ten strokes later both boys came
and Jimmy's skirt was now covered with white sticky cum. The
boys were all smiles, and to his surprise, none objected when
he said he really had to get home and lay down, due to the
cramps he was suffering. All four gave him light kisses on
the cheek and either pats on the ass or shoulder as they let
the beautiful new girl go on her way.
COSTUMED CAPERS
Part 2 of 5
When he was a good mile further down the tracks, Jimmy
stopped and sat in the grass. "God! that was close," he said
to himself and suddenly his body started shaking with the
built up tension and realization of what could have happened
back there. After a while he finally got his body back under
control and after taking several slow, deep breaths, got back
up and continued towards home. The balance of this trip was
uneventful until he reached near the house and passed several
neighborhood women out for a walk who knew him. Neither,
however recognized him in his school girl persona, but both
turned and visually followed him down the block, so he had to
circle around the corner before returning to his house through
the alley.
Approaching his parent's house from the back, he careful-
ly checked each window, looking for one left unlocked. He
didn't even try the doors, knowing them to be steel security
doors with double cylinder dead-bolt locks. After checking
his own room, the kitchen, dining room, and bathroom he was
getting worried, all were closed and locked. The only room
left on the "protected" side of the house was his older
sister's bedroom. "Thank God!" he thought, as he saw the
window lock was turned in the unlocked position, but the
window was about 7 feet from the ground. Getting one of the
trash cans from the side of the house and turning it upside
down, Jimmy reached the window and removed the screen, the
after opening the window climbed into Kathleen's room. His
skirt caught on the window ledge as he passed through the
opening and he heard a tearing sound as the buttons on the
left side of the jumper tore loose. Jimmy leaned back against
the wall once inside and sat for a couple of minutes as he
finally let the tension of the ordeal of going home dressed as
a girl pass from his mind and body. When he felt up to it
he got up and immediately stripped off the girl's clothing
right there in his sister's room, balled it up and walking
nude through the house went to his own room where he again
dressed in his own clothing. Looking at the ball of clothing
on his bed, he decided he would need to hide it until he could
get it back to it's place in the costume room and then put it
in the bottom of his cedar chest. Retrieving his spare keys,
Jimmy locked his sister's window, replaced the screen and
returned to school on foot. As he walked back, Jimmy avoided
the woods along the railroad tracks, not wanting to take the
chance of running into the boys again and them recognizing him
as the "girl" who jacked them off earlier. He got back to the
school just as classes were ending for the day and the parking
lot was full of students leaving for home.
Since his school keys were on the same ring as his car
keys he knew he would have to get someone else's in order to
get into the boy's costume room and retrieve his clothing,
including this billfold and keys. The stage area was empty so
he went to Miss Hall's office the theater instructor. (knock,
knock) "Uh...Miss Hall, could I bother you a minute?" said the
boy to the pretty young teacher. Miss hall was just out of
college, only 24 years old and a tall woman with long brown
hair and a body which Jimmy frequently included in his sex
dreams. "Oh, Hi Jimmy, here kind of late aren't you?"
"Well... yes, you see I was, was fixing some sound wiring,
down, down on the stage and had to go through the boy's
costume room, and, and, accidently let the door close behind
me, and, and, locked my keys in the storage room. Could,
could I borrow your key, so, so I can get mine out?" the boy
said almost trembling with fear that she might either refuse
him or insist on accompanying him to the room. "Locked
yourself out, did you... well I guess we all make a mistake
every once and a while." said the pretty woman as she gave him
a grin, "Sure Jimmy, here you go, but please make it fast, I
have to leave as soon as possible." "I'll run down and back,
shouldn't take anytime at all," he eagerly replied as he took
the key from her hand and bolted for the door.
True to his word, Jimmy ran to the costume room and after
inside quickly searched for his clothes. The clothes were in
the laundry bin, "Good!" he thought, he wasn't worried about
the clothes, just the wallet and keys. But when he checked
the pockets of the pants, EVERY POCKET WAS EMPTY! "OH NO!" he
cried, leaving the door unlocked he returned Miss Hall's key
to her then again went to the costume room and searched every
drawer, bin and cabinet in the room searching for his belong-
ings. Finally, he came to the realization that one or more of
the girls must have checked the pants and found his wallet,
money and keys, But Who? Even more important, how was he
going to explain all his clothes and belongings being in the
other storage room. Maybe he could say he was wearing a work-
type jumpsuit, because he didn't want to get his own clothes
dirty and had accidently locked himself out of the room?
Maybe, ... With nothing more he could do, Jimmy locked the
room and went home.
The next day, Jimmy returned to the boy's costume room to
make a second search, having left the door closed but un-
locked. He searched every nook and cranny in the room but to
no avail. As he was getting ready to leave, he heard voices
coming down the hallway, it sounded like the girls from the
previous day. As he was frozen by the door trying to make up
his mind as to what to do, suddenly it opened and he was face
to face with Jane, the chairperson of the costume committee.
"Well, well, if it isn't Jimmy," she said "Looking for
something are we?"
"No, no just finishing up fixing the sound wiring that I
started yesterday," Jimmy quickly replied.
"So you are the one who left the lights on."
"I didn't know I had, but maybe I did."
"Did you loose something else?"
"Not that I know of."
Jane had advance toward Jimmy throughout this conversa-
tion and he had unconsciously backed further into the room.
Three girls now stood between him and the door. Jane was a
senior and VERY big in comparison to Jimmy, standing almost 5-
10 and EVERYTHING about her was proportional to that towering
height. The other two girls were Samantha (Sam) and Susan the
freshman, who the girls had blamed for leaving the boy's
clothing in the girls costume room. Sam and Suzie were about
the same size as Jimmy one being 5-5 and the other 5-6 and
about equaled his 120 pound weight.
"I don't think that's why your here at all." Jane
observed as she stood toe-to-toe with him and looked down at
him. "I think your looking for THIS!" and she held his
billfold directly in front of his eyes.
"Or maybe THESE!" said Sam and dangled his keys about a
foot away.
Jimmy had continued backing as the girls closed in on him
and was now standing with his back to one of the wardrobe
cabinets surrounded by the three girls. Jane threw the wallet
to Susan and extended her arms placing the hands on the
cabinet so that Jimmy was now trapped between them.
"Your a liar Jimmy," she calmly said, "We know you were
down here yesterday and that you left ALL of your clothing in
the girls costume room, because we found it there and the
proof is your keys and billfold."
"We even blamed Susan for putting the clothing in the
wrong room!" said Sam, "Until we found evidence of the owner."
"Now maybe you'd like to try explaining WHY we found your
clothing in the other room Jimmy?" said the amazon towering
over him.
"I, I took them off and put on a jumpsuit, so, so I
wouldn't get them dirty while I worked," he stammered.
Jane glared down at him, "You know, I just MIGHT buy that
Jimmy, except for one little thing. YOUR UNDERWEAR! I just
don't see why you would take THEM off if you were wearing a
jumpsuit."
Jimmy was now trembling and knew they had him. There was
no way he could explain taking off his underwear and leaving
it in the other room and they knew it. "I... I..."
"I think you were doing something ELSE down here Jimmy,
and I think you better tell us right now or we'll just have to
take our evidence to Miss Hall and let you explain it to her!"
Jane said in a stern voice.
Jimmy stuttered and stammered but couldn't get his mind
to come out with the real reason, he turned beet red and was
now noticeably shaking in front of the girls.
"You know what I think Jimmy, I think you were down here
either jacking-off or wearing girls costumes or both!"
"No! No, I... I..." he tried to reply.
"Well girls I guess we'll just have to tell Miss Hall
about this little pervert," said Jane.
"Uh, Uh... PLEASE DON'T," Jimmy stammered, "I'll do
whatever you want!" he offered.
"But JIMMY! Why should we believe you, you've already
lied to us twice and STILL haven't told us the TRUTH!"
"I... I..." Jimmy tried to reply.
"Jane, Jimmy seems to be having trouble verbalizing what
he did, maybe we should have him SHOW us." Samantha suggested.
This brought smiles to the faces of all three girls,
without a further word, Jane grabbed Jimmy's arms and pulled
him towards the door, where Suzie was waiting with the door
open and then forced him into the other costume room. One
inside, the door was closed and locked using the double keyed
core and Jimmy was now trapped with NO escape possible without
a key.
"I... I CAN"T!" cried Jimmy, who now had tears flowing
down both cheeks and was shaking with fear. Susan was
standing with her back leaning on the door and a wide smile on
her face; Jane and Sam flanked him to either side and also
were grinning.
"Oh but you CAN!" said Jane, "And you WILL! Or we will
just take this little party right up to Miss Hall's Office."
"NOW STRIP YOU LITTLE PERVERT! OR WE'LL DO IT FOR YOU."
Jimmy knew his only choice was to plead to Miss Hall and
hope he wasn't expelled, then live with the shame OR do what
the girls wanted. "Will you promise not to tell anyone?"
Jimmy asked in a whisper.
"We're not promising ANYTHING," replied Jane, "but if you
give us a good little show, we just MIGHT not tell."
Jimmy figured this was about the best he was going to
get, so he quickly stripped off his shirt and kicked off his
shoes, then scanned the smiling faces of the girls who had now
seated themselves for a show. Again turning red, he unbuckled
his belt and dropped his pants leaving him in only his
underwear and socks. Taking a deep breath, he removed his
socks and then turned his back to the girls and removed the
underwear. He now stood completely naked in front of three
girls his own age whom he had wanted to screw.
"Very GOOD," said Jane, "Now do EXACTLY what you did
yesterday, and If you don't, we'll be able to tell by your
body language. And if we see you are not doing it, we'll just
have to spank you then take you to Miss Hall!"
Jimmy dug out all the clothing he had worn the previous
day and proceeded to dress himself as before. The girls
watched in silence as he put on a pair of white nylon panties
and a camisole, then the little ankle socks, patent leather
shoes, crinoline petticoats, and the frilly pink party dress.
He then sat at a makeup table and applied foundation to his
face, followed by mascara, a light rouge to his cheeks and the
pink lipstick to his lips. Silently, Jimmy then dug out
another wig, since the one he had been wearing yesterday was
at his house, and arranged the long blonde hair about his
shoulders. The girls watched in amazement at the transfor-
mation taking place before them. The sixteen year old boy
quickly became a VERY pretty 12-13 year old girl dressed for
a party. When Jimmy was done, he rose and without looking at
the girls (which would surely cause him to lose his nerve)
proceeded to the full length mirror and again looked at the
lovely creature staring back from the glass. Jimmy blocked
everything except this vision from his mind and was soon again
reaching under the skirt and again stroking his cock, totally
oblivious to the fact that three girls were watching him.
This time when he came however, it was to the cheers and
applause of the girls who hooted and giggled and laughed in
their joy. Jimmy collapsed to a sitting position on the floor
in exhaustion and relief from the sexual tension. He had DONE
it, now maybe they would let him go.
When he opened his eyes, Jimmy saw the girls now sur-
rounded him and were closely looking at his makeup and attire.
All were smiling and soon, six hands were roaming over him
checking the texture of the clothing and how well it fit him.
One hand however, was moving upward from his right knee along
the inside of his thigh, stroking the smooth flesh, Jimmy
wanted to object, but the hand felt so good, he couldn't bring
himself to speak. He hand moved under the skirt and worked
it's way along his thigh until it found it's way into his
panties and gently worked on his cock. The hand moved down
and the fingers rolled his balls between them then returned to
his cock and continued stroking until he was again hard.
Jimmy had closed his eyes when he felt the hand, knowing he
could not stop them anyway, but not knowing WHO's hand it was.
The hand continued and he could hear the crinoline petticoats
being moved out of the way and felt the cool air brush across
his now fully exposed crotch. He laid back and let the hands
do as they would to his body. In his excited state, it didn't
take long before Jimmy again climaxed, his cum spurting up and
soaking the hand working his cock.
"Open your mouth," said Jane in a raspy whisper, and when
he did, fingers soaked with his cum were inserted. "Lick them
clean." was all she said, and Jimmy complied, marveling at the
taste of his own juice. Without a word being said, the girls
got up and left the room, leaving Jimmy still dressed as a
girl on the floor, with his panties down around his knees and
his cock now very limp. Jimmy was too exhausted from two
climaxes to do much, so he just laid there on the floor for a
while and recovered. "What will happen now?" he asked
himself, but could think of no answers. Jimmy got up after
awhile and dressed in his own clothing, but to his distress,
his wallet had not been returned to him, Jimmy left and went
home in a daze.
The following day, Jimmy found a note in his mailbox at
school, "Report to the costume room at 3:00 today!" signed
Jane. The girls apparently were not done with him yet.
At 2:45 Jimmy was walking down the hall towards the
costume rooms and could hear voices coming from that direc-
tion. When he opened the door, he stopped and froze. Inside
the room were twelve girls, all of the costume committee and
all of the makeup committee, along with a couple of others he
didn't recognize.
"Come in Jimmy," said Jane and gave him a big smile.
Jimmy was still frozen in place and when he realized that
he was probably going to be forced to do another show, only
this time in front of a dozen girls his own age, he started
trembling with fear and tears welled up in his eyes. Suzie
and Sam grabbed hold of his arms and quickly pulled him into
the room, placing him in the center, in front of Jane.
"Jimmy, you gave us such a GOOD show yesterday, we
invited the rest of the girls on the stage crew down to see
you perform. What we want you to do is EXACTLY the same thing
you did yesterday and the day before, nothing more and nothing
less."
"Jane, PLEASE, please don't make me do this, I... I can't
do that in front of all these girls." Jimmy pleaded.
"Oh but you CAN and you WILL, NOW STRIP you little sissy
wimp! DO IT OR WE'LL DO IT FOR YOU!"
COSTUMED CAPERS
Part 3 of 5
When Jimmy hesitated, Jane got mad and grabbed his shirt,
tearing in open and down away from his body. Then while two of
the girls held him, she removed his belt and taking a large
pair of scissors cut his pants off leaving him with only he
shoes, socks, and underpants. Jimmy was now crying and was
shoved to the floor, the cold concrete giving him goosebumps.
He struggled against the girls but was far outmatched. Even
in his terror state, all of the physical contact was getting
him excited, and his penis was rapidly growing. When they had
him down, someone removed his shoes and socks and then Jane
took her shears and cut his underwear from the waist downward
along his hip bones, then jerked the garment from his body
like she was removing a baby's diaper, leaving him down
totally nude in front of 12 smiling girls with his little
hard-on pointed towards the sky. "Ohs and Ahs," accompanied
the sight of his 5 inch cock, which excited the girls and who
were already at a fevered pitch.
"Oh isn't it cute," said one. "But it's a little small,"
said another. Giggles and laughter filled the room as the
girls teased Jimmy about his little cock and having been
stripped by girls his own age. At this point Jane grabbed
hold of Jimmy's cock and told the girls to let him up, and
after he was again standing pulled him by his member to a
steamer trunk nearby.
"Jimmy, you have been a VERY bad boy and will have to be
punished," she said as the trembling boy stood before her with
his cock still firmly clenched in her hand. "Lay across my
lap, you will have to be spanked!" Three girls quickly
positioned Jimmy face down across Jane's lap, her skirt had
ridden upwards and his cock now hung between her legs. Jane
reached underneath and guided his cock, then clamped down with
her thighs pinning him in place, while her left arm encircled
his waist. All the while, the girls were continuing to tease
Jimmy about his situation and laughing at his predicament.
"You should have done what you were told!" said Jane as
her right hand descended on his butt and a loud smack echoed
through the room. The flesh of his right cheek erupted in
pain, but before he even yell, (crack) another landed on the
left cheek.
"Ah, ah, please Jane, I... I'm sorry, I... I'll do what
you want," Jimmy cried with tears flowing down his face which
was bright red from the humiliation.
(Crack! Crack! Crack! Crack!)
"Damn right you will, you little sissy wimp pussy, you
will do EVERYTHING I tell you, WHEN I tell you to do it, or
this will just be a minor introduction to PAIN!"
Jane continued to wail away on Jimmy's behind while the
girls continued to tease him about being stripped and spanked
by girls. His cock was rubbing against Jane's nylon covered
thighs and with each spank, his cock was driven downward
encased by the smooth material. Jimmy was just about to
climax when Jane decided that his now bright red ass was
sufficient for the moment and shoved him from her lap onto the
floor at her feet. Landing on his back, Jimmy's cock was
standing straight up and twitching from it's excited state.
This brought even more laughter and teasing from the girls who
then pulled him to his feet so they could inspect his cherry
red buns. His cock bobbed and weaved as he moved and the
girls got a big kick out of watching it and continued to
giggle and laugh at it. Jimmy was completely humiliated and
was red from his hairline down from shame, his ass cheeks were
on fire from the spanking but he just stood still as the girls
poked and prodded the burning flesh, tears streaming down his
face and his dick standing at attention wanting relief.
At this point the girls from the makeup committee who had
been conferring during the spanking approached Jane with their
suggestions. Linda, a pretty redheaded Senior and chairperson
walked over to Jimmy and looked him over closely to confirm
their observations.
"Jane, before you have Jimmy put on the REAL show, the
members of my committee have noted that he is not yet ready
for the costume committee's part of the production. We note
that this GIRL has hair growing on her legs, arms, underarms
and groin which are not consistent with the character to be
portrayed in the show. We therefore propose that our commit-
tee, PROPERLY prepare this actress for her part prior to
costuming." All of this was delivered in a voice which
sounded very professional and objective and Jane immediately
agreed with their plans. "Have at him girls!" was the reply.
Jimmy was immediately pulled into the adjacent girls
dressing room and placed in a shower and told to wash himself
from head to toe. All twelve girls watched as he showered,
but just as he finished, two stepped into the stall with him
and turned off the water. His entire body below the neck was
coated with shaving cream and the girls went to work with
razors, methodically removing every hair below his neckline.
When they were done, they told him to again shower and then
patted his how hairless body dry with big fluffy towels. His
body was then dusted with sweet smelling powder by two more
girls and he was told to bend over and a girl held his cheeks
apart while another using a razor made sure that no hair
remained around his puckered little hole or the base of his
balls. A soothing cream was massaged into his still burning
ass which brought whimpers and groans from Jimmy. Throughout
this procedure, Jimmy's cock remained at attention but no
relief was in sight.
Jimmy was then lead to the other side of the room where
there was a line of makeup tables, and seated in one (Ginger-
ly), Linda then turned him to look at her and studied his
face. After a minute or two she took a comb and scissors and
started working on his hair, trimming here and there. Then
applied styling gel to his hair and then blow dried it while
working the hair with a round spiky looking brush. Satisfied
with the results, she tilted his head back and started
plucking hairs from his eyebrows. This startled Jimmy and the
girl saw the reason for the fear. "Relax Jimmy, I'm just
cleaning them up a little, I won't make you look like a
faggot." Jimmy relaxed and she continued to work. Next Linda
directed one of the girls to bring her some ice and had a tool
of some kind in her hand. Before Jimmy realized what was
happening, he felt a sharp prick in his left ear, then his
right.
Janet, another senior, took over at this point and
applied a coat of foundation to his face, feathering it out to
his hair line and base of his neck. Next came mascara, rouge,
lipstick, lip gloss, eyeliner and eyeshadow. The other girls
watched Janet work and gave squeals of glee when she was done,
approving of her work. Jimmy was turned around to face the
mirror and did a double take at the pretty young girl looking
back with gold stud pierced earrings and a modified "boy cut"
hair style. His cock which had half deflated during the
cosmetic procedures immediately came back to full attention,
although it was hidden by the barber's drape they had placed
over him while working. "Excellent, EXCELLENT!" exclaimed
Jane who then resumed control of Jimmy.
"Ok Sam, Your turn now," said Jane as she turned Jimmy to
face her and stood him on his feet facing the girls. Sam came
forward and using a gauze pad wiped Jimmy's chest then stepped
behind him and a minute latter came back into view and
immediately pressed something against the left side of his
chest and held it there for about 30 seconds. When she
removed her hand a woman's breast was visible on his chest and
looked to be made of rubber or something, immediately she
performed the same procedure on the right side and Jimmy now
sported a matched pair of breasts suitable for a girl of 17 or
so. There were no straps or anything and the breasts moved as
he breathed and were obviously weighted to match the real
thing. She must have attached them with some kind of glue or
something he thought to himself.
"Well how do you like them?" asked Samantha.
"I, I...," Jimmy's mind went blank as he looked down at
the tits, then slowly his hands moved upwards until each
cupped a breast. The texture felt real and when he moved they
swayed like the real thing. "I think Jimmy likes his new
tits!" exclaimed Suzie, this brought howling laughter from all
the girls. Jimmy was then moved in front of a full length
mirror and to his astonishment and delight the vision reflect-
ed showed a pretty short haired girl; the only thing spoiling
the vision was the hard cock sticking out from the crotch.
One of the girls approached Jimmy from behind and placed
a black lace garter belt around his waist, hooking it from
behind. Next he was assisted in putting on a pair of stock-
ings which were attached to the garter belt and a pair of
black strap type shoes with 5" spiked heels. Jimmy had great
difficulty steadying himself on the high shoes and was
steadied by one of the girls until he got his balance. When
he looked in the mirror, Jimmy noted that the black lace
perfectly framed his crotch and made his cock even more
noticeable than before. Jimmy was told to stand a minute and
felt a wet washcloth pressed against the left cheek of his
butt. When it was removed, Jimmy was turned sideways and
shown that he now had a "tatoo" on his ass in the form of a
pair of bright red lips. "It will wear off in a couple of
weeks," said the girl, "then we can try something else."
A flirty little black "cross-back" swing dress was placed
over his head and pulled down into place. The dress had a
deep scooped neckline in front which showed skin down to his
breasts, the shoulders and back were bare to the waist, the
material slanting down the sides like a halter top. Two thin
straps formed an "x" pattern on his back holding the dress in
place. The skirt flared at the waist into a full skirt which
ended at mid-thigh. Looking at himself in the mirror, Jimmy
almost came on the spot, the sexy dress made him beautiful!
Jimmy turned back and forth watching himself in the mirror,
the girls congratulated themselves on his appearance and Jane
motioned for them to seat themselves around the room.
"Well ladies, what shall be call our little Sissy-boy?
asked Jane, "Obviously, we can't call her Jimmy, because
that's a BOY's name and she is to pretty to be called by a
BOY's name."
"How about Jill?"
"No, Lisa..."
"No, Tammi..."
"Jenny," whispered Jimmy.
"Fantastic! Jenny it is," ruled Jane.
"Well now, 'Jenny' it's time for our show," Jane directed
and moved to seat herself among the other girls.
Jimmy's cock had been hard now for over two hours and
regardless of his embarrassment, he NEEDED to get some relief.
Facing the girls, he lifted the hem of his skirt and proceeded
to stroke his straining cock with his right hand while he
massaged his balls with his left. It only took about 10
strokes before cum was dripping from his cock, then immediate-
ly it started shooting in jets, arching out towards the girls,
some of it landing on one of them's leg. "Shit!" said the
girl, "He got it on me." Jimmy was in a daze when Jane forced
him down on his knees and ordered him to lick it off the girl,
he complied without even thinking, to the cheers of the
assembled girls. When done, Jane ordered him to stand and
bend over and hold on to a high stool in the center of the
room.
"Sam go get that special prop will you?"
"Sure Jane, be right back."
"Jenny, we have a SPECIAL treat for you, since you are
now a girl, you must learn about sex and we are going to teach
you."
Almost immediately Samantha returned with a box and Jimmy
watched as Jane removed her skirt, her powerful legs were
wonderful and he especially liked her flowered bikini panties.
Jane reached into the box and pulled out a fake cock about 8
inches long with straps attached to it. He watched in
amazement as she connected the dildo to her body then stood in
front of him. "SUCK MY COCK JENNY" was the order as he looked
at the thing from eye level. "You can't be a REAL girl
if you can't suck cock," Jane whispered as she rubbed the
device across his face and mouth by moving her hips. Two
girls grabbed him by the shoulders so it was clear that they
intended him to do this. Jimmy gave the thing a tentative
lick then opened his mouth and Jane slowly inserted the cock
until he gagged, then backed out and entered again, repeating
this procedure penetrating a little deeper with each stroke.
While Jane thrust at his mouth, Sam instructed him on relaxing
his throat and use of his tongue, telling him to swirl it
around the head and to suck as it was pulled back.
"Boy's love that suction around the head," she said and
"if you can deep throat, they'll buy you anything you want!"
Jane just kept stroking in and out murmuring, "Yes baby,
suck my hard cock, that's it, suck it hard, good girl, suck me
hard Jenny."
All the other girls gathered around and critiqued his
technique until they all felt he was doing it right.
"Now Jenny," murmured Jane, who's eyes were kind of
glazed, "I'm going to take my little Jenny's cherry." Jimmy
was bent over further, his forearms resting on the stool and
as Jane moved behind him and lifted his skirt. A cream was
worked around his little asshole and soon he felt a finger
pressing against the tight little opening. It massaged the
hole and soon was working it's way inside.
"Ah, Ah, NO! NO!" Jimmy cried as the pain moved from this
bottom to his brain. "Please No!" he pleaded but the hand
just kept working.
"Relax Jenny and this won't hurt, but if you fight it, it
will hurt like a son-of-a-bitch." he was told.
Jimmy relaxed all he could and soon the finger was moving
freely in and out of his ass, it was soon joined by another
and another until three fingers were probing his backside.
When the fingers were withdrawn, Jimmy sighed and relaxed,
until suddenly he felt the giant dildo pressing against his
little muscle. It had been well lubricated and the fingers
had loosened him enough that the head went inside without much
resistance. But as Jane pressed forward, she met resistance
and stopped periodically until she could feel slight movement
indicating relaxation of his internal muscles. Soon the dildo
was buried to the hilt and she pulled it back until just the
head remained inside Jimmy. Then grabbed his hips and in one
forceful stroke buried it again until her thighs slapped
against his. The base of the dildo was rubbing against Jane's
clitoris and every time she slammed into Jimmy it sent
electric shocks through her, so without any further encourage-
ment, Jane pounded the strap-on dildo into the boy's ass
without mercy. After about 10 minutes, Jane climaxed and fell
on top of the boy with the dildo still buried inside him. All
the girls cheered and clapped hooting and laughing at the show
now concluded. When Jane recovered, she withdrew the monster
from Jimmy and used a washcloth to clean his bottom. Then
planted a kiss on the right cheek of his butt to match the one
on the left, only this one was in pink lipstick.
"Well it's time to go girls," Sam suggested and they then
lined up before Jimmy, and each gave him a hug and a kiss,
thanking him for the 'show' and telling him they looked
forward to many more in the future. They left the room and
only Jane, Suzie, Samantha and Jimmy remained.
Jimmy was lost mentally, he didn't know what to do or say
and for a while the girls ignored him as they cleaned up the
room. When they were done, Jane gave him a deep kiss, a hug
and a firm pat on the ass. Sam and Suzie each gave him a hug
and a kiss on the cheek. All three headed for the door and as
they exited, Jane laid his keys on the floor but held up his
wallet and said, "I think I'll hold onto this a little
longer." she then turned and walked out closing the door
behind her. Standing alone in the middle of the dressing
room, still dressed as a girl he was still in a daze and sat
on a chair trying to collect himself. The cold metal chair
immediately reminded him that he was wearing a short skirt and
that he had no panties on as the metal contacted is skin. He
quickly got up, folded the skirt under him and again sat on
the chair. Jimmy's whole body shook as he realized what he
had just done in front of 12 girls: been stripped, spanked,
shaved, made-up, masturbated, sucked a fake cock, then been
butt-fucked by a girl with that same cock. As the scenes
flashed through his mind, he realized that someone had been
TAKING PICTURES through every stage. "Oh SHIT!" he thought,
"what am I going to do now?"
COSTUMED CAPERS
Part 4 of 5
On unsteady feet, he moved over to the door and almost
fell when he bent over to pick up the keys. Immediately, he
noticed that some were missing, THE ONLY KEYS ON THE RING WERE
FOR HIS HOUSE AND THE LIGHT/SOUND BOOTH! His car keys and the
keys for the costume rooms were missing. Jimmy looked around
the room and quickly found that the only clothing in the room
was what he was wearing, no towels, nothing made of cloth was
visible, only a small black purse on the counter and he knew
there was nothing in the light/sound booth because he had
cleaned it up himself. "God!" he thought, "I'm going to have
to walk home again, but dressed like this!" Jimmy looked at
the clock on the wall and was shocked to see that it was 5:15
p.m. "I better get going," he thought "before the janitor
comes down here." Jimmy picked up the purse and placed his
keys in it since he had no pockets and as they fell in noticed
that the purse contained cosmetics, a brush, a comb and a
package of condoms; no money and no ID's.
Resigned to his fate, Jimmy left the room and slowly
walked down the hall trying to get used to the 5" heels. He
had no experience at walking on this toes and knew it was
going to be a LONG walk home. Jimmy again escaped through the
fire exit on the back of the building only this time, walked
around to the front and through the parking lot which was
empty except for his car and one other. Jimmy tried the doors
on his car in hopes that MAYBE he had left one unlocked, but
no dice, locked up tight. Putting the thin strap for the
purse over his right shoulder, Jimmy started walking, the cool
evening air brushed across his bare shoulders and back and
occasionally caused his skirt to blow and lift. "Can't have
that!" he thought as he shoved the skirt down to cover his
still naked bottom. Jimmy walked towards home and as he
approached the private school, could hear the voices of boys
playing basketball over near the building. When they saw him,
he immediately heard whistles and cat calls for the pretty
girl passing the school. Jimmy ignored them and straightening
his shoulders, walked firmly on by, but noticed that his hips
had picked up a definite swing in response to the height of
the shoes.
About halfway home, Jimmy heard a car slowly approaching
from the rear, almost pacing him, when he looked over his
shoulder at the car, what he saw almost caused him to fall.
It was Jane, driving HIS car and it was full of the girls from
the stage crews. One had a video camera and was filming him
walking down the street, while two others were taking pictures
with still cameras. They pulled up along side and the one
with the video camera yelled "Hi Jenny," which Jimmy tried to
ignore. "Show us your panties!" which caused Jimmy to freeze
and tightly hold the skirt down. This caused all of the girls
to laugh and the car pulled ahead, then sped off in the
direction of his house. Jimmy continued walking, his feet
were now killing him, and finally reached the end of his
street. Along the way, he passed several people who knew him,
but none seemed to recognize the pretty girl as little Jimmy,
this increased his confidence and it was only as he approached
his house that panic again started setting in. His car was
parked in the alley behind the house (the keys laying on the
seat) but his parent's car was not in the driveway. His
sister's car however, was in the garage.
Carefully, Jimmy worked his way around the house looking
through the windows to see who, if anyone, was home. The
light was on in Kathleen's room and the living room but the
rest of the house was dark. From the sounds, Jimmy thought
that his sister was either taking a bath or shower, as he
could hear water running in her bathroom. Jimmy worked his
way back to the back door and as quietly as possible, inserted
his key and opened the door. The kitchen was dark and when he
closed the door, it was even darker. As he felt his way along
the countertop, he banged into a chair and lost his balance on
the spiked heels and fell to the floor.
"Is that you Jimmy?" called his sister.
"Yea Sis, just bumped into a chair."
Jimmy was scrambling, trying to get up, but kept loosing
his footing on the slickly waxed kitchen floor. Suddenly, the
lights came on and his sister was standing in the door,
wearing a robe and slippers, rubbing a towel on her wet hair.
"What the..."
"Uh, Sis, uh..."
"What the HELL is THIS!" said his astonished older
sister.
Jimmy was sprawled on the floor and as he rolled onto his
side to attempt to get up on his knees, the skirt flopped to
reveal his bare backside and the red "lips" tattoo flashed at
Kathleen.
"Jimmy, Jimmy, what is all this?"
"I..., I..., we have to talk Kathy."
"I should say so," she replied and seeing the trouble he
was having, took hold of his arm and helped him stand, then
lead him to the carpeted hallway where he could get better
footing.
"Where's Mom and Dad?" Jimmy whispered.
"Their gone for the weekend, we're alone for the week-
end," she responded and Jimmy gave a great sigh of relief.
"Now what's IS THIS?"
Jimmy dropped to a sitting position with his back against
the wall and his knees drawn in tightly and started to cry,
his body trembling and shaking as he released the tension from
his mind and body.
Kathleen knelt beside her brother and gathered his head
into her hands and pressed it against her chest, while she
stoked her fingers through his hair, on the back of his neck
and over his bare shoulders. Kathy smelled clean and lightly
scented and even though racked by his release, his body
responded to the feel of her warm breasts now pressing against
his face where her robe had parted. Kathy looked down and
again saw that Jimmy was wearing nothing under the dress and
that his cock was as hard as it was clearly visible.
"You Know, Young LADIES should either wear underwear or
keep their skirts pulled down," Kathy chided.
Jimmy immediately realized she was referring to him and
dropped his legs onto the floor, pulling his skirt down to
cover his exposed crotch.
"I'm not sure what this is all about", Kathy offered,
"but it does explain the button I found at the foot of my bed
last night. That button didn't match anything I own, so it
must be from something of yours." Kathy could feel something
pressing back at her from her brother's chest and pulled the
cross straps down over his shoulders which dropped the
neckline of the dress to the point where she could see his
rubber tits. "You sure look REAL," she murmured and reached
into his dress to feel one of the breasts; "FEEL REAL too, but
how are they attached, your not wearing a bra?"
"They're..., they're attached with some kind of glue,"
came the whispered reply, "Suzie, uh, put them on me."
"Jimmy, I'm trying to be patient, waiting for you to
explain, but I just don't understand, are you GAY or WHAT?"
"NO! I'm not THAT!" he cried, "I, I just like to wear
girls clothes."
"So, you must be one of those Transvestites."
"I, I guess so," he replied in a dejected voice. "But I
got caught, by, by the girls on the costume committee, and,
and they did this to me." he whimpered and began trembling
again.
"Well it looks to me like they did a good job! You could
go anywhere and no one would NOT think you were a girl, unless
you gave yourself away. If you hadn't spoken to me, I
wouldn't even have recognized you. Now get up and let's go in
the living room."
Jimmy arose with difficulty (trying to keep his skirt
down below his crotch) and walked ahead of his sister into the
living room. Kathy noticed the sway in his hips as he walked
and the great legs and smooth back displayed by the dress.
"God! I wish My legs looked that good," she thought to
herself.
Jimmy sat on a chair and Kathy sat on the sofa directly
across from him and chuckled as Jimmy fussed with the skirt,
trying to keep it pulled as far down as possible. But since
it was so short, it kept riding up his thighs every time he
breathed.
"Now tell be the WHOLE story," his sister directed.
Jimmy told her how he had on occasion he had sneaked down
to the girls costume room and dressed in various outfits then
masturbated in front of a mirror and that two days ago the
girls had come in while he was dressed and he had to hide, but
that they found his clothes and took them out of the room.
How he had dressed in the school uniform and made his way home
(leaving out the encounter with the boys) and had climbed into
the house through her window, changed and went back for his
wallet and keys. But that they were missing when he got into
the boy's costume room. How Jane had left him a note saying
to meet her Suzie and Samantha and that they had made him
dress for them and give them a show. That, today he had
spanked and been made-up by both the girls on the costume
committee and make-up committee and been made to give a show
for 12 girls. Then left attired as he was, to make his own
way home. Jimmy conveniently left out the parts about the
dildo and only told of jacking-off in front of the cheering
girls. Throughout the dialogue, Kathy watched her brother and
could see his excitement at various parts as well as his fear
at others, his body language differed considerably from his
voice at various parts and his short skirt was showing a
definite bulge which did not belong on a girl.
"So you are called 'Jenny' when dressed-up? Well Jenny,
where did you say the clothes you wore yesterday are? In your
room? Go get them, I want to see what you wore.
Jimmy retrieved the ball of clothing and handed them over
to his sister. Kathy immediately recognized the dried cum
stains on the skirt, the only question in her mind was the
quantity. There was entirely too much even for the recupera-
tive powers of a young man.
"Jenny, you didn't tell me everything and I don't think
you hated this as much as you are putting on. In fact, I
think you liked the WHOLE thing, otherwise, that silly little
cock of your's wouldn't be making a tent out of your skirt."
Jimmy immediately placed his hands over the bulge in his
skirt, trying to hide it while his mind kept telling it to
deflate. His penis however, seemed to have a mind of it's
own. "Sis, I, I hated it." he whimpered.
"Now maybe you'd like to explain all this cum all over
your skirt, there is way too much for it to all be yours, so
fess up!"
Jimmy filled in the part about having been stopped by the
boys along the railroad tracks and having had to jack them off
in order to escape. Kathy noted that his cock was standing
straight out even stiffer than before if possible.
"No, Jenny LIKES to be dressed, and LIKES to put on shows
for girls, NO DOUBT ABOUT IT! I think I'll call Jane and get
the WHOLE story, cause I think Jenny didn't tell me every-
thing." Kathy, immediately went to the telephone and called
Jane who she knew from school, them being in several classes
together. Jane not only confirmed what Jimmy/Jenny had told
but said there was more and that she had photographic proof.
Kathy invited Jane to come over as well as any of the other
girls and to stay the night if they wanted, since her parents
were out of town. Jane readily agreed and said she would call
the others and might even bring a surprise!
Meanwhile, Jimmy had gone to his room and removed the
dress and was trying to remove the breasts, but the glue was
too strong and it felt like he was ripping his chest off; but
the breasts hadn't released at all. Just then, Kathy stood in
the doorway and observed her brother now attired only in the
garter belt and hose, trying to pull the left tit from his
body. She immediately walked over behind him and with all the
force she could muster, smacked his butt with her hand.
(Crack!)
"Ouch!" cried Jimmy.
"Jenny you LIED to me!" she yelled as her hand descended
again (crack!), "You didn't tell me everything!" (crack!) "I
don't tolerate liars!" (Crack!) "You little bitch, you are
going to be punished for this!" (Crack! Crack! Crack!) "Now
bend over!"
Kathy grabbed one of Jimmy's belts and folding it over
gave his ass about twenty swats until it was covered with
bright red marks. Jimmy was crying and when she stopped fell
to the floor blubbering, his whole body quaking as he cried.
Kathy left the room and when she returned, she was carrying a
black halter dress with chiffon skirt which she laid on the
bed.
"Put that dress on, then fix your face and come back to
the living room, and BE QUICK ABOUT IT, or you will get more
of the same."
Jimmy got to his feet and picked up the dress, pulled it
up his legs and over his hips. The cotton/lycra band around
the waist fit tightly and when he tied the halter in place, he
saw that it had a split in front right down between the
breasts, with a back even lower than then one he had been
wearing before. The skirt was shorter and came only 1/3 down
his thighs just below the top of his stockings, showing even
more leg than before. The chiffon rustled when he moved and
stood out making his hip look wider and his waist smaller. He
looked in the mirror and noted that this dress was the sexiest
he had ever seen, even better that the swing dress. Jimmy
repaired his makeup using his sister's makeup table and mirror
then went to the living room as directed.
When he stepped around the corner, he froze, there sat
Jane, Samantha, Susan, Debbie and Linda, in addition to his
sister.
"Come on in Jenny," said Kathy, "You already know all
these girls. They came over for the night and want to see
your new dress." "Isn't she cute girls?"
"Lovely, I really like the was that dress shows so much
skin." said Jane, "Really sexy."
"Go out in the middle and take a couple of turns for the
girls," ordered Kathy, "I want them to see the whole thing."
Jimmy did as directed and the girls giggled when as he
turned, the skirt lifted showing his bright red ass cheeks and
that he was still wearing no panties.
"Jenny, the girls must be thirsty, go get them some soft
drinks and bring them here and serve them."
"Yes Kathy," he replied and immediately went to the
kitchen and poured iced drinks for the girls.
"You know Jane, I should thank you girls, I always wanted
a servant, and it looks like now I HAVE one."
"We aim to please," said Jane, "As long as we can still
play with her every now and then."
"But of course! After all, you found her."
Jimmy returned at this point and served the girls their
drinks, as he stood by each girl, she would run her hand up
his thighs and either fondle his soft penis and balls or pat
his ass while taking the drink in the other hand. Jimmy's
cock started to swell from the handling, and by the time he
had completed the circuit, was hard and standing straight out.
Kathy directed Jenny to stand at the end of the couch while
Jane inserted a video tape into the player. Then to his
horror, the ENTIRE escapade of the afternoon was shown on the
TV while he stood before the girls. When the dildo scenes
came on the screen, Kathy hit the hold button on the remote
and the image of Jimmy with a cock in his mouth was frozen on
the screen.
"Look at the EYES girls, and the EFFORT, I think little
Jenny LOVES sucking cock!" observed Kathy.
"If you think she likes that," Jane replied, "Wait until
you see how much she loves taking it up the ass!"
"Your kidding!" exclaimed Kathy, "Did she let you do
THAT?"
"Yes and loved every minute of it, here I'll show you."
Jane grabbed the remote and fast forwarded to the butt
fuck and Kathy couldn't believe the look of pleasure on her
brother's face, while Jane plowed his backside.
"Well girls, I think it is our duty to keep little
Jenny's pussy happy from here on out,"said Kathy.
"Absolutely," replied Jane and murmurs of agreement came
from the others. "In fact, that surprise I mentioned on the
telephone should be here any time now."
COSTUMED CAPERS
Part 5 of 5
The girls continued watching the film and just after the
scene of Jimmy walking down the street with his skirt swing-
ing, the doorbell rang. "I'll get it," said Jane. When she
returned, she was accompanied by a tall young man, who she
introduced as her older brother Ron, who attended State
College and was home for the weekend. Jimmy was introduced to
Ron as 'Jenny' "the little sissy I told you about."
"Ron, would you be willing to do what I talked to you
about?" asked Jane.
"Sure, why not!" he replied as he smiled at the six
girls.
"Ron is a bisexual," Jane explained to the others, "and
has agreed to break Jenny in right with the REAL thing." "He
has also agreed to let us watch!"
Jimmy/Jenny was placed on his knees in the center of the
room, while Ron removed his pants and moved in front of the
trembling boy. Jane, standing behind Ron, pulled his under-
wear down, and many "Oohs and Aha's" of appreciation were
heard from the girls when his 9" tool came into view already
erect.
Kathy had been standing beside Jenny and now bent over
and whispered in his ear, "Go for it Jenny, You know you want
too."
Jimmy reached out with his hand and gently grasped the
formidable cock, then leaned forward and gave it a tentative
lick with his tongue. Deciding it tasted good, he opened his
mouth wide and put as much of it inside as he could, swirling
his tongue around the shaft and it penetrated his mouth.
"Aha, God, that feels good," moaned Ron as the girls
cheered Jenny on. Jimmy got a tempo going, moving in and out,
never letting the cock completely escape his mouth as his hand
worked the big balls suspended below it. "Yes, Yes," Ron
cried and took hold of Jenny's head as his hips pumped his
member into the warm cavity.
Just as Ron was about to cum, Jane pulled Jenny back from
her brother. "Get up Jenny and bend over, on hands and knees,
so Ron can fuck that little pussy-ass of yours."
Ron quickly got behind, Jenny and flipped her skirt up
onto her back, then put on a condom and spread the K-Y jelly
he had been handed, on, around and into the tight little hole
before him. Jenny's asshole opened immediately in response to
his gentle probing, and soon Jimmy could feel the head of
Ron's cock pressing at his opening while the man held him with
a hand on his waist. Ron inserted the head, then grabbed
Jimmy's waist with his other hand and pulled the boy back
while he pressed inward with his manhood.
The girls cheered and clapped and as Ron established
motion with his hips, clapped in time with the thrusts,
yelling, "Go, Go, Go" with each stroke. Jimmy, was now
thrusting backwards with each thrust forward by the cock and
was moaning as the big cock worked on his prostate gland from
the inside. It wasn't too long before Ron froze in mid-stroke
and Jimmy felt the cock jerking in his rectum. This trig-
gered, Jimmy and he shot his load onto the carpet below him,
even though no one had even touched his little penis.
Ron gave it about 5 more thrusts, shooting with each
stroke, then fell back on his heels as Susan, Jane and Linda
fondled and kissed him. The condom was removed from his now
soft cock and one of the girls washed him and also Jimmy's
ass. Jimmy just laid on the floor trying to recover his
strength. He had never, cum so hard in his life and was
exhausted.
Ron was redressed and led to the door by his sister and
all of the girls gave him a kiss in thanks for his efforts.
"Anytime girls." was all he said as he went out the door and
waived to them.
Kathy, then turned to the girls and said, "I don't know
about you girls, but I think it is about time Jenny learn to
eat pussy and mine will be the first!"
"Yes!" was the reply in unison and everyone returned to
give Jimmy the first of the lessons to follow. In the living
room, Jimmy was placed on his knees in front of a large chair
and watched in wonder as his sister removed her skirt and
panties before his eyes, then proceeded to instruct him on the
proper way to make a woman happy with his mouth. This was
just the first of MANY such lessons to follow.