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.
