This is a work of fiction. Any character portrayed living or dead is purely coincidental.
Jack was an Asian boy that had very feminine features. He was about 5ft, dark hair, 16 and also wore his sister's clothes. Jack was always in his sister's closet her make-up and perfume. Jack has a friend that he secretly has a crush on. His name is Matt. Matt had blonde hair, American, 5ft 7in, and 16, single mom and no siblings. He was an average kid. Both were into anime, and regular cartoons, magna, and videogames. They became fast friends when they both entered 9th grade. Jack never told Matt about his cross dressing or his female name is Yumi. Something he and his sister talked about.
The Monday started like any other day for Jack. He got up, dressed and greeted his loving family. His mom was a secretary at a local computer firm and dad was a lawyer. "Morning everybody." He said. His parents looked at him. "Ready for school?" His mom asked. "Yes." Jack said as he ate a bowl of cereal, and then grabbed his book bag. He walked outside to see Matt ready to meet him. "Matt, why didn't you knock on the door?" "I just got here" he replied. The boys began their walk to school. They talked about the anime that was on television last night.
Both boys were bored for most of the morning. It was when the boys entered health class after lunch did Jack's get happy. The teacher Mr. Peacock told his students. "I want every boy to partner with a girl." Everybody ended up with a partner except Matt and Jack. "This assignment is that you are going to be parents. In two weeks I want a 3 page report about being a parent and how it affects your mental health. " The teacher handed each group a doll. When he got to Jack and Matt he handed each of them one. After class the teacher spoke to both boys. "Look I know you boys didn't get partnered with a girl. So I'm going to give you a choice be partners together or do this separate." "Jack quickly spoke. "I'm willing to be his partner." Matt was taken back a bit. The teacher agreed to them being partners and took the other doll back.
After school Jack spoke "Look I'm sorry about jumping like that in health class." Matt looked at his friend as they kept walking. "I have a secret Matt, and I think us as partners will make you understand." "Why don't you tell me your secret now?" "Matt I don't want to talk about this right now." How about I come over tonight and try and explain this to you." Matt agreed and then took the doll home with him. When Jack walked into his house no one was home. He went upstairs to his sister's closet and found a denim skirt, white blouse, pink nylons and white flats. He put the clothes on and then the make-up. He smiled to himself. He wondered what Matt would think of him dressed up like a girl. Jack's mother called the house. "Honey we're at the restaurant waiting for you." "I'll be there as soon as I can." Jack quickly changed back into his school clothes threw his sister's clothes into his back pack washed his face grabbed his back pack and flew to the restaurant. When he sat down and placed his order he told his family about how is day was. He also told them that he and Matt are partners in a school project for mental health. The rest of the meal was quiet. After dinner Jack told his family he was going to go straight to Matt's house. Jack and his sister then excused themselves from the table. Jack grabbed his back pack and headed for the bathroom. His sister followed.
Jack walked into the women's bathroom and changed into his sister's clothes. His sister who followed behind him then did his make-up and did his hair. "Well Yumi good luck with Matt." Yumi smiled at her sister. "Thanks." 5 minutes later Yumi was out the restaurant with her back pack. About a half hour passed and Yumi finally made it to Matt's house. Yumi knocked on Matt's door. Matt answered quickly surprised to see a beautiful girl at the door. "What can I do for you?" The Yumi giggled and trying to sound very feminine. "Aren't you going to invite me in?" Matt asked the girl to come in. For a moment both were silent. "My name is Yumi; Matt." "Do I know you?" "Matt you know me better as Jack, your friend." Matt was shocked by his friend's transformation.
"Is this a joke?" Yumi answered questions only Jack would know. "Matt is your mom home?" "She's at work." Yumi unzipped Mat's pants pulled them and his undies down then and watched as his cock shot up. Yumi then knelt down and began to start sucking on Matt's cock. Matt put his hands on Yumi's head. Yumi kept bobbing her head back and forth, gagging on Matt's cock. "Suck my cock good baby." After a few more sucks Matt exploded. Yumi swallowed all the cum Matt shot out. Yumi then stood up. And removed her dress slid her panties down exposing her cock. Matt knelt down and began to suck Yumi. Yumi moaned with pleasure. "Oh keep going." Yumi said.
After a few more sucks Yumi exploded in Matt's mouth. Matt swallowed every drop. He then went got up grabbed her by the waist and kissed her on the mouth. "Where did you learn to do that?" Yumi asked. Matt gave a smile. "Before you came over I found a porn video where two guys blew each other." "It really got me excited." "Where and how did you learn to suck cock?" Yumi blushed. "My sister showed me a video on her laptop showing a cross dresser blowing some guy." Matt still looked interested. "My sister also has a dildo in her dresser and I would practice sucking on that." Matt grabbed his friends hand, they walked into the kitchen Matt then bent Yumi over the kitchen counter.
"I'm sorry for what I'm about to do. But I want to do this." Yumi didn't say anything. Matt grabbed her hips and began plowing her ass. Yumi screamed for a minute as Matt's cock entered her ass. He began to thrust as Yumi began to moan. "Oh Please don't stop, I Love this." Matt kept thrusting his cock deeper into Yumi's ass. After a few more thrust, he exploded in Yumi's ass. Matt smiled. Yumi turned around and they kissed some more. Yumi then removed her blouse revealing her nipples. She jumped on the counter. Matt then began to suck on her nipples. He licked and kissed them then began to suck each one. Yumi was moaning again with pleasure. She was moaning so much she grabbed herself.
Yumi jacked off and shot a thick load on Matt. Matt and Yumi smiled. They both looked at the clock and realized it was getting late. Matt told Yumi he could spend the night at his house. Yumi agreed. Jack called his parents and told them that he was sleeping over. He would be up early enough to come home and be ready for school the next morning. Jack's parents agreed. Jack hung up. Matt grabbed Yumi's pink nylon legs and began to massage them. He moved down and removed her shoes. Then worked his way back up. "Jack/Yumi I love you." "I love you too Matt." They kissed some more on the way to Matt's bedroom. "I know how to start our paper." Matt said. Yumi looked at him.
"My beautiful girlfriend Yumi came over for a school project, we fucked, and out came baby." Yumi laughed. After the assignment which they got a B on. Jack who still dressed as Yumi and Matt became a couple. They went to their proms together and even talked about going to the same college. Jack's parents found out about him being Yumi and while not happy they still loved their son. And Jack's sister still takes him clothes shopping.