Kyle’s ordeal
By wargamerdude.
(from the author, this is my first sad attempt at writing a story and posting it for public critisim. I hope that I get enough feedback to help me write future chapters. I know this one is short but I didnt know how long or short each chapter should be. )

Trish had never thought that shopping for lingerie could be so interesting, but it was. November was almost finished and she took a break from Christmas shopping. She was shopping for herself now. Walking though the aisles of different style bras at Victoria’s Secret had sparked a wicked idea in her head. She never wore very sexy styles of lingerie but looking at the bright pink padded cups and purple, blue, imported silk and elaborately embroidered styles of lace or beads had sparked a new idea. She would never wear such things herself. She hardly ever brought her sixteen-year-old daughter lingerie. Dianna bought her own stuff now. But, the bastard Kyle could. The thirteen-year-old brat would do anything she told him too, or else. She would love to see how the stupid brat looked wearing women’s lingerie and she would dearly adore the shocked look on his face as he opened his gifts for Christmas and saw lacy lingerie instead of athletic stuff he liked. He needed taken down a notch anyway.

She picked out a few especially lacy pair of bras, a purple bustier and matching bikini panties. To top off the humiliation, she picked out a few pairs of stockings that looked like they should fit his legs. She couldn’t wait to see the look on his pretty face. She paid for the stuff and then drove home. Dianna would be out with her boyfriend and kyle would be hanging with his friend so she would be alone for at least a few hours. She went to her bedroom and hid the sacks in the back of her closet. Then she booted up her computer. She started up Photoshop and opened one of Kyle’s best pictures. How he looked so much like a girl already shocked her. A few times when they went out to lunch together, someone would mistake kyle for a girl. When the waiter called him, ‘ma’am’ the latest girl mistake, he got very angry and the waiter quickly apologized. She just giggled because she thought it was very funny. She gave the waiter an extra ‘ten’ for a tip over it. It was her after all, that forced him to get his hair styled in curls.

Then she chose some lingerie that was on a disk and pasted it over his body. A pink bra and matching panties over the appropriate areas and blushed his cheeks. She shaved some of his eyebrows in the picture and was shocked by the final result. She saved the picture and printed it. After that picture was printed, she called up another pose and doctored it properly. She made four pictures in different poses and angels. She was pleased with the final result. She decided to call one of her friends to show them too. Trish knew that her friend would know how to proceed. Rachael was a mistress herself. She had various kinky tastes and had dressed her own boy up at times. Trish knew she could trust Rachael.

The other woman told her she would be free tonight to talk. So she made the proper arrangements. She told Dianna to stay in tonight and keep watch over Kyle. The two never got along and Kyle always got the shaft but that wasn’t her problem. Kyle was an ass. Dianna always ended the fight and Kyle would start crying over it. The problem was that Kyle didn’t like her calling him Kelly. He needed to get over it. There was nothing wrong with being Kelly. Kelly was a pretty name.

Trish was at Rachael’s front door by the time the sun was starting to sit. The air was starting to get a cold chill as the wind whipped at her face. Rachael opened the door and quickly let her in. Rachael was a tall woman at around six foot. She was very athletic and her body showed it. Her arms were muscular and her thighs were toned and very powerful. Her shoulders almost looked like a mans. If it wasn’t for her face and her hair style, one might mistake her for a man but that would insult her. She enjoyed overcoming men. For reasons she couldn’t understand, many men felt very degraded if they were overpowered and physically defeated by a woman. Men were even humiliated if a highly trained female boxer defeated him. Men were simply idiots.

She sat down across from her and her leather skirt hugged her shape tightly. She clearly looked sexy and vicious at the same time. She asked, “Hello trish, what can I do for you tonight?”

“We have known eachother for a long time and I need some help from you. “

Rachael was studying trish. As if she was trying to figure out what this was all about. Her mouth moved slightly and she said, “Yes, trish. I figured. I ask again, what can I do for you girl, let me know and I will see what I can do.”

Trish reached into her purse and pulled out the pictures she printed. She handed them over to Rachael, “perhaps this will help you. Tell me what you think. “ She took them from Trish and looked at them for a few minutes. She giggled from time to time.

“OH Trish this is perfect. I love that purple bra and panty set you had him in. Oh and that nightie and stockings. Those are perfect for him. “

“He never actually wore them Rachael,” she quickly corrected Rachael. “I used Photoshop but I bought the lingerie. I want your help to get him to wear them, and I want you to help me train him to accept his new position and status, as Kelly. “

Rachael smiled at her, “Yes indeed. I will help you. What, may I ask, brought this new side of you that you would harm your son in this way? What made you turn against him? Has he done something?”

“Kyle has done a lot to displease me. One of them was being born as a boy after the event. The event is too painful that I wish never to discuss it. He just pisses me off to no end and I want to change the asshole to someone whom I can adore and love. Will you teach me how to train him? To be a sissy maid for his older sister?”

Rachael corrected her, “You mean adopted sister, don’t you? I know how close the girl is to your heart and you treat her better than your son.”

Trish spoke harshly, “I chose Dianna. I had no choice with Kyle. I was raped. “

“Yes I know. I’m sorry for what your brother did. I can understand your feelings and I will help you so Kyle is never a danger to women like his actual father was. “ After that was out of the way, Rachael continued, “But this project will be very long and intensive. Before he is comfortable or even accepting, we need to move slow. Before we dress him up in those elaborate sexy bras, we should start him on training bras. He needs to be trained in womanhood before he is moved to adulthood. Do you understand, Trish?”

She nodded, “Yes I understand. Can we still give them to him as a gift?”

“Yes, “ she said. “That will be his first introduction to womanhood. How far do you want to take this, “

for a few seconds, her eyes closed and she said nothing. Then she said, “I want him to go all the way. After he is comfortable as a woman then we can start introducing him to hormone treatment. Or at least when he knows how to pass as a girl then we can proceed to making his body shape as a girl. I need to learn when and how we can get some testosterone blockers. “

She smiled, “That’s easy. One of my best friends is a licensed doctor. She can prescribe anything. But she can easily loose her license. So we need to be sure he is subdued enough not to rat us out when he gets the option and he will get it sooner or later. I know how to make it happen. “

“Great,” Trish said. “Lets go shopping then.”

Both of the women hopped in Rachael’s car and drove to the mall. She had gone to many stores and got a lot of lingerie for a young teenager. She also picked out some dresses and skirts for him too. The last thing they got was a black French maids miniskirt. She thought it would look very good on Kyle. After hours of shopping, they went back to Rachael’s place and she watched Rachael order a pair of breast forms online. Trish prepared to head home. Before she could get in the car, Rachael took Trish in her arms and looked carefully into trashes face, “ are you sure you want to go though with this, Kyle is your son so are you sure?”

“Yes,” Trish said, “I am very sure. Now I have to be going home. “

after she made it home, Kyle made it home. Dianna was already home. Trish was standing near the stairs and said, “Kyle, I have something that I want to talk to you about. “

his uncertain face showed everything. He knew his mother didn’t love him. He struggled all his life for affection from his mother only to never get any. He didn’t know what was wrong with him but he needed to find out. All he wanted was his mothers love. “Okay, mom. I will be up in a few minutes. “ He walked up the stairs. His mom was sitting on the bed waiting for him. “Kyle sit down, we have to talk.