Jason is Discovered Ch. 1

Jason wandered around the house, he quietly moved into the dining area, looking around quickly, he then made his way silently along the corridor and into the kitchen. Jason was familiar with this routine; he did it most days when he got home from college. He then walked out into the garden, glancing around. He made his way back inside and made his way upstairs keeping an eye out as he did. Upstairs, he poked his head into each room in turn before making his way to the room at the end of the hall. He opened the door and closed it behind him.

Jason's room wasn't particularly big but it was tidy which was unusual for an eighteen-year-old boy. The walls were painted white, although you wouldn't have known it by looking, every wall was adorned with posters, ranging from a huge poster of Kylie Minogue looking sexy in a bikini to another huge poster of Oasis who frankly looked wasted. Jason wasn't looking at those posters now; he had other things on his mind as he quickly removed his clothes. He undid his tie and pulled off his blazer, undid his shirt and pulled that off too. He removed his socks and pulled his trousers off folding them all into a neat pile on the bed. He stood still for a couple of seconds wearing just his shorts just listening. He then opened his bedroom door and silently made his way back up the corridor and to the first door on his right. He silently twisted it and let himself in.

Jason's mother's room was very pink, the wallpaper was pink flowers, the duvet was pink flowers, the curtains were pink and even the carpet was a light pink colour. Jason made his way over to the far side of the bed and carefully and quietly opened the top draw of her dresser. He reached in and pulled out a pair of black stockings. They were the ones that had a thick band of lace at the top. Jason placed them carefully on the bed. He then closed that draw and opened the one underneath. He reached in and pulled out a pair of black lace thong panties. He then pulled out a matching black bra. Jason placed them all carefully on the side of the bed and went to the wardrobe. He pulled out a short black stretchy skirt and a white silk blouse. Jason then picked up all of the clothes, turning behind him to make sure that there were no signs that he had been there and made his way back out of his mother's bedroom and into his own.

Jason, took his time sliding the black stockings on his legs, he didn't have much hair on his body at all so his legs looked quite feminine in the nylons. He then removed his shorts and replaced them with the black lace panties they fitted him well; he liked the feel of the material nestling in his butt crack. Jason then stood up and stepped into the skirt, pulling it up around his waist. Jason then picked up the bra and looked at it, he put it on his lap as he lent down under his bed and pulled out a large shoebox. He opened the box. Inside were some six-inch platform heels, a white bridal garter belt, a blonde shoulder length wig, some red lipstick and two fake breasts. He picked out the silicone breasts and placed them in the bra before expertly attaching around his back and over his shoulders.

Jason gave his breast a squeeze to get them into the desired position and then picked up the blouse. He slipped it on, the black bra was clearly visible through the sheer material but because of the material his breasts actually passed as real. Jason admired how he looked for a minute before turning his attention back to the shoebox. He picked out the garter and slipped it on over his leg. He then picked out the shoes and slipped them onto his feet, then the blonde wig, which he checked in the mirror; lastly he applied the lipstick. Jason sat on the side of his bed looking more like a woman than a boy. His cock was hard in his mother's panties and he started to rub it through the silky material. Jason lay back on his bed and rubbed harder as he ran his fingers over his breasts. Jason slipped his hand inside the panties and started to pump his cock back and forth as he was about to cum his bedroom door swung open.

Jason jumped a mile, "shit" he said looking at his mother stood in the doorway, just as he sprayed a stream of cum all over her panties and stockings.

"I knew it," she shouted. Jason was too stunned to move, or speak or do anything. He just sat still, cum seeping out of his cock over his hand that was still tightly clasped.

"My new panties," she said looking at him, "you dirty disgusting little boy, take them off immediately and clean yourself up," she yelled going red in the face. "Christ" she shouted as she slammed the door shut behind her.

Jason just sat for a minute before releasing his cock. His cum hung from his hands down onto the stockings and the panties he was wearing. He finally stood up; a little shaky he made his way to the bathroom. It was a good job it was right next to his room. He took the wig off and washed the cum from his hands. He then used tissue paper to wipe it from his mothers clothing. He had always been so careful before not to cum on her panties, her knew that they could stain and he could be found out. Jason looked down at a big white mark on her black lace panties and swallowed hard. He started to remove her clothes, wiping them off as best he could before dropping them into a pile. Once he was naked he washed his face. Jason opened the bathroom door with the clothes in his arms and turned to go back to his room.

"No you don't" said a voice. Jason looked up to see his mother stood at the end of the hallway. "You come with me young man," she said in an angry tone. Even though Jason was naked he walked slowly after her trying to use the clothes he was carrying to cover himself. She walked down the stairs followed by Jason.

Jason couldn't help admiring his mothers, firm butt as she stepped down the stairs. Considering she was nearly forty her body was immaculate. She had shoulder length naturally blonde hair, full firm pouting lips, very firm breasts that looked as if they could stand up straight all by themselves and she had that butt. Jason dreamt about that butt and as he watched it swaying from side to side in front of him he felt his cock start to twitch. They walked out into the kitchen where Jason's mother directed him to put all of her clothes except her panties and stockings in the washing machine. She then gave Jason a packet of soap and told him to wash those items by hand in the sink. Jason started the water, still trying to hide his embarrassment. His mother left the room and went into the lounge area. Jason got to work, he was very meticulous in his work, he washed the stockings and the panties making sure that he had every stain removed.

Once he had finished he walked into the lounge with his hands covering his now deflated cock. Jason looked at his mother a little suspiciously, she was looking through a magazine and when she looked up she had a wry smile on her face. "I always wanted a little girl, but when I had you there were complications and that was it for me, no more children. No little girl to dress up in taffeta and lace, no little girl to put her hair in bunches, no little girl to dress up," she said looking directly at Jason. "But as I had a little boy, I was grateful none the less, thought he would grow into a strong young man, a credit to the family, but what did I get instead?" she said pointing at Jason. "This, a weedy little boy with no muscle in his body whatsoever and the charm of a damp rug, a credit to no one, not even himself."

Jason stood there quite astonished at what she was saying.

"A boy who likes to dress up as a girl, frankly wants to be a girl!" she spat at him. "You damn sissy, I actually knew you did this, you may have been careful but I could tell when my panties had been worn or when my stockings had been slightly misshapen by you slightly longer legs. I have a surprise for you sissy, and she should be here within the hour."

Jason stood there naked and shaking, he didn't say a word.

"For Christ's sake sit down," Jason's mother barked at him.

Jason sat in the chair opposite her keeping his hands on his lap. They sat there and waited for about half an hour before a car pulled up outside and Jason's mother went to see who it was. "She's here," she said looking into Jason's eyes as she rounded him and went to the front door.

Jason was too scared to move or speak or do anything.

Jason heard his mother chatting to another woman in the corridor and tried to listen for a clue as to who it might be. After a minute or so his mother walked into the lounge and stood in front of Jason.

"Here he is, the big sissy," she said pointing at Jason.

A gorgeous woman appeared through the door. She was about twenty five years old, with long blonde hair, tied back into a French platt, she had large full tits that looked as if they were going to spill out of her top at any moment and a very slim body. She was wearing a white doctor's coat with what looked like black tights and high heels. Jason just looked up at her, he then felt acutely embarrassed about being seen naked and about being called a sissy by his mother.

The woman looked Jason up and down, "yes I think we can do something her."

"Good" said Jason's mother.

"What is her name?" the woman asked.

Jason's Mother replied, "I don't know never thought of a name for her before."

"May I suggest using the same initial, so maybe, Jill or Julie or Jenny?" replied the woman.

"Good idea, I like Jenny, call her Jenny" Jason's mother said looking down at Jason.

The woman stood in front of Jason, "stand up Jenny" she said in a strict tone. Jason who didn't really know what was going on stood up. "Good girl," she said as she stroked his slightly longer than usual hair. Jason felt turned on by this but didn't want to react. "Come with me," the woman said as she turned and walked out of the room, she started to make her way upstairs. Jason looked at his mother still covering himself with his hands.

"Well go on, do as she said," his mother said in an annoyed tone.

Jason quickly scampered after the woman and made his way upstairs. The woman had picked up a large black doctor's case and had that in her hand as ascended the staircase. She made her way to the bathroom, before holding the door open for Jason and then closing it and locking it behind both of them.

"My name is Mistress Rebecca, you will call me Mistress or Mistress Rebecca," she said in a very stern voice, "do you understand?"

"Yes" replied Jason looking at her.

She raised her hand and slapped him hard across the face. Jason clutched his cheek in pain. Realising his mistake, he rectified it by replying, "sorry Mistress," before bowing his face back in his hands.

"That's better," she said as she unbuttoned her coat. She let it fall off, Jason looked up to see she was wearing a leather thong and a leather bra, her tights were in fact hold up thigh high stockings. Jason felt intimated by her immediately.

"Stand up straight now Jenny and let me have a good look at you" she said as she snapped on a pair of surgical gloves she had retrieved from her case. "Come on arms by your side, head up, don't slouch, be a pretty little girl for me" she said as she started to touch his legs, inspecting them closely, "mmm not much hair, that's good."

Jason felt strange as this woman inspected him closely. He stood there quietly as she ran her hands all over his legs then inspected his butt, even pushing her little finger slightly. She closely inspected his penis, pulling back the foreskin, so that she could have a good look. Jason felt completely violated, here was this woman touching him in such a cold medical way. She checked his testicles she checked his chest, his back, his ears, his mouth, his eyes and finally his hair. Once she had finished she snapped the gloves off and tapped him playfully on the head, saying, "good girl" before turning back to her case.

Mistress Rebecca fished in the case and brought out what looked like a large electric shaver. She plugged it into the razor socket and turned it on. Jason watched the top of it as a small loop of electricity surged around it. "I need to you stay quite still for this, if you move it could hurt a lot more, do you understand," she said adjusting one of the knobs on the shaver.

"Yes Mistress," replied Jason as he gritting his teeth and closed his eyes.

Mistress Rebecca, brought the shaver down to his leg, she ran it over his legs. It didn't hurt so much as gave him an uncomfortable sensation of pins-and-needles. He opened his eyes and looked down, as Mistress Rebecca passed the shaver over his hairs they seemed to burn away. Mistress Rebecca worked the shaver all over Jason's body, being very careful around his pubic area. She shaved his chest and his underarms before doing his face.

"There you won't need to worry about shaving again!" she said packing the shaver away.

Jason ran his hand over his chin, it felt completely bare, no hair whatsoever. "Ok now we need to dress you in something a bit more suitable," she said looking in her case. She brought out a pair of white frilly French knickers. "Step into these" she said as she knelt down. Jason obliged and stepped into the leg holes. Mistress Rebecca pulled them up for him. The knickers had a special padded section at the front that enclosed Jason's cock, hiding it from view. Mistress Rebecca pushed her hand down the front of his knickers and arranged him so that they fit properly. Jason enjoyed the feeling of her warm hand positioning his flaccid cock into the correct position and felt it twitch slightly when she grasped it.

"You are a horny little slut, aren't you little girl?" she said as she removed her hand.

"Yes Mistress, sorry Mistress," he said as he bowed his head, his cock getting harder.

"Next thing," Mistress Rebecca said as she went back to her case again, she pulled out a matching white bra. Then she brought out two silicone breasts not dissimilar to the ones that Jason already owned. She passed them to Jason and he expertly fastened the bra. These silicone breasts were bigger than his ones; they gave him a much more defined cleavage. Mistress Rebecca then unzipped another part of her case and pulled out a dress, it was light pink in colour with lace around the bottom and the arm holes and neck. It had a big bow that was tied around the waist. Mistress Rebecca hung it up on the door before pulling some more things from her case. She un-wrapped a package and pulled out some white thigh-high stockings that she handed to Jason. He immediately started to scrunch them up so he could slide his legs in more easily. He pulled them up to his thigh; they had a three-inch lace top to them that looked stunning. He then put on the other stocking. Mistress Rebecca then handed him a suspender belt; it was also black with six suspenders hanging down. Jason turned holding it around his waist as Mistress Rebecca fastened it for him. Jason then set about adjusting the straps and fastening them to the top of his stockings. Once he was done he checked his clothes to make sure they were neat and tidy and then turned to face Mistress Rebecca once again.

She looked at him and smiled, "you are going to make a fine little girl," she said as she reached up for the dress that she had hung on the door earlier. She removed it from the hanger before gesturing for Jason to raise his arms over his head and angle towards her. She slid the dress down onto his arms and head until it rested on his shoulders. She then knelt and began arranging the underside of the dress, making sure that it fell correctly, straightening out the lace and tying the bow around Jason's waist. Mistress Rebecca stood back and took a look before slightly adjusting Jason's left sleeve, "perfect" she said before turning back to her case. Jason sat on the side of the bath, the feel of the lace at the bottom of his dress rubbing on his stockings felt wonderful, as did the feel of his French knickers pressing softly against his hard cock. Mistress Rebecca turned back around; she was holding a pair of white, high-heeled sandals, with five-inch heels and two large straps over the toes. She put them on the floor; Jason slid his feet into them and stood up. They felt comfortable, more comfortable than his shoes and he liked them. He walked a little around the bathroom. Jason could hear some banging going on from next door but didn't thin k much of it.

"Sit down on the floor slut," Mistress Rebecca commanded fishing out a small box from her case.

"Yes Mistress" Jason replied as he carefully sat down.

Mistress Rebecca then brought out a hairbrush and some hair products. Jason's hair was fairly long for a boy, coming down to just above his chin. Mistress knelt over him her warm pussy radiating through her leather thong resting on his leg as she worked. She brushed his hair down and around and made it into something of a bob. She used mousse and hairspray to style it and used a small pair of scissors to give it a slight trim. Once she had finished his hair looked very feminine, it was a lot more bouncy and now curled up underneath coming to his ears. "Once it grows longer it will be easier to manage," Mistress Rebecca said as she put the brush and sprays away. She then picked up the small box and flipped the lid. Jason looked in to see a makeup box full of powders and creams and lipsticks. "Stay perfectly still now," she said as she took a small sponge and started to apply something to Jason's face. It felt strange to Jason but he quite liked the attention that he was getting. She applied something to his cheeks, something to his eyes, something to his lips and finally red polish to his finger nails before she stopped, snapped the make-up box shut and smiled at Jason.

"You look beautiful Jenny," she said in a soft girlie voice before getting back to her feet and packing her things back into the case. Jason sat there not sure what to do. Once Mistress Rebecca had finished she told Jason to stand up and go and take a look at himself in his mothers full-length mirror. He opened the door and made his way to her room. He looked into the mirror and was amazed. In front of him, looking back was a fifteen or sixteen year old girl, dressed up for a party. His mouth was hanging open in amazement as he ran his now painted fingertips all over his 'new' body.

"You turned into a beautiful little girl haven't you Jenny?" asked Mistress Rebecca as she stood behind Jason.

"Yes Mistress" replied Jason still staring at his reflection.

"I think you should go and show your mother now don't you?" Mistress said softly.

Jason looked up at her and went red, he felt embarrassed that a strange woman had done this to him and now he was going to show his mother. The shame in his face showed as he slowly stepped along the landing in his pretty white heels. He made his way carefully down the stairs followed by Mistress Rebecca. Jason listened as two pairs of heels clipped their way down on the wooden stairs; one set sounding careful and slow while the other set sounded fierce and impatient. Jason finally got to the bottom and paused outside the door to the lounge, Mistress Rebecca, gave him the once over and smiled before pushing the door open and then pushing Jason after it.

If Jason felt embarrassed before it was nothing to what he felt now. Sat on the sofa in front of him was his mother and his father. His mother grinned as Jason flushed with colour. His father looked equally embarrassed. For a long while no one said anything. Jason just stood still his eyes facing the carpet while his mother and father both stared at him.

"Well give us a twirl!" his mother snapped in a sarcastic tone.

Jason looked up a bit and began to very slowly turn around.

"Very nice," said his mother looking up at Mistress Rebecca who had taken a seat to the left of the room.