Newsgroups: alt.sex.stories
COSTUMED CAPERS
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 realization 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 building. 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.
From: adietrech@aol.com (A Dietrech) Newsgroups: alt.sex.stories Subject: Story: Costumed Capers 2/4 TG femdom Date: 10 Dec 1994 01:55:34 -0500
"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, UNDERSTOOD!" 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.
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 carefully 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 surrounded 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!"
From: adietrech@aol.com (A Dietrech) Newsgroups: alt.sex.stories Subject: Story: Costumed Capers 3/4 TG femdom Date: 10 Dec 1994 01:55:41 -0500
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
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.
From: adietrech@aol.com (A Dietrech) Newsgroups: alt.sex.stories Subject: Story: Costumed Capers 4/4 TG femdom Date: 10 Dec 1994 01:55:08 -0500
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."
The girls continued watching the film and just after the scene of Jimmy walking down the street with his skirt swinging, 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 underwear 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 triggered, 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.