Kyle was your average 10 year old. He was a little small for his age standing at 4ft 2. He was relatively skinny but participated in many sports so he was in good shape. He had short dark hair. He had lots of friends. He was well mannered and always sought to do the right thing. His parents were extremely proud of him. They lived in the Chicago suburbs where both his parents lead very successful careers so they were pretty well off. Everything seemed to be perfect in their life yet, Kyle still felt something missing in his life.
Around Christmas time, Kyle's mom received news that her mom wasn't doing so well and needed to go see her. She didn't want Kyle to have to see his dying grandmother though because he hardly knew her and it was going to be a lot of sitting around. Kyle's dad suggested he go stay with his aunt and cousin who lived on the way there. Kyle's mom thought this was a great deal and shouldn't be a problem since it was only going to be for a weekend. Kyle's dad called up his sister Anne to see if it would be all right. Anne thought this would be a great idea since Kyle and Hailey hardly saw each other and it would be a great opportunity for them to bond. Kyle was excited to get to see his cousin. He usually only got to see her maybe once a year.
They left Friday afternoon. It took them two hours to get to Anne and Hailey's house. They lived in the country a few miles out of a small town. It was a 2 story farm house well maintained. When they arrived, Anne came outside to meet him. Kyle came out of the car toting a small bag he had filled with a change of clothes and some toiletries. Anne came up to Kyle and gave him a big hug "Hows my favorite nephew"
"Pretty good aunt, thank you for having me this weekend" Kyle replied as Anne took his bag. Kyle's parents talked with Anne for a bit and then said good bye to Kyle and were on their way. Anne lead Kyle inside to go greet Hailey.
It was just Anne and Hailey who lived there. Anne had divorced her husband after she caught him cheating on her and had received a way better deal in the settlement. Hailey's dad had moved away and sent them money every month. Anne worked as an interior design consultant to keep her busy and she made very good money which allowed her and Hailey to live very well, especially in the country.
When they entered, Hailey came up as excited as could be. Hailey was 13 and stood a good 5in taller than Kyle, she was skinny and she had long dark hair and showed the first signs of puberty. She didn't have many friends since she lived in the country and so got very lonely. Kyle was just as excited to see his cousin it had been almost a year since they had last seen each other. Hailey took Kyle's bag and put in her room where he would stay for the weekend since she had an extra bed for friends and since the guest room was still being re-done.
After she came back down, she suggested they go outside and play in the snow. It had snowed just recently and there was about a ft. of snow on the ground. Kyle thought this would be great. He never got to play in the snow back at his house because it all got plowed away. They got on their snow gear and headed out. Hailey knew a great hill to go sledding on. They got some sleds out and began the walk over to the hill. It was a couple of miles away which gave them plenty of time to catch up. When they reached the hill both of them were excited. Kyle had never been sledding on so big of a hill and Hailey didn't come out here very often because she didn't have friends over that often. They sledded for a long time having the time of their lives. They did goofy tricks like try to sled backwards and ride on the same sled to get it to go faster. About an hour into their fun, Kyle noticed he had to pee pretty bad. He realized he had not gone since he had left the house. He just ignored it though because he was having so much fun. It began to get dark and it took a little bit to get back so they were finally forced to leave both thinking they would return the next day to do the same thing. As they began to walk back, Kyle's urge to pee got worse. He had to go really bad and it was two miles back to the house. Hailey noticed Kyle dancing in place and knew exactly what was bothering him. She thought for a moment and then began to smile. She thought up of a way to make this weekend much more interesting. She finally asked Kyle what was wrong even though she knew the answer. Kyle replied "I really have to go pee, I am thinking I might just go behind a tree if that's o.k.".
Hailey quickly bluffed "You can't, you could get hypothermia or something, you wouldn't want to get frost bite there" gesturing down to his area
Kyle conceded not wanting to succumb to the fate Hailey had mentioned and said "Lets just hurry then, I really have to go" They continued walking Hailey brimming with excitement about her plan and Kyle partially skipping trying to hold it in. As they got closer to the house, Hailey began to drag her feet a bit forcing them to walk slower. Eventually the house came into view. Hailey trotted up by Kyle again. As they came inside Hailey rushed into the bathroom. The other two were being remodeled at the time and neither Hailey nor Anne saw this as a problem since it was normally just the two of them. This made Kyle extremely frustrated. Hailey went to the bathroom but took her time not wanting Kyle to make. Kyle began to bang on the door as he became extremely desperate. Anne heard this and walked down to see what the matter was. Kyle cried out "I'm not going to make it, hurry up"
Hailey knew it was time, she slowly washed her hands, and then opened the door. Kyle was bent over trying to hold it in. As he tried to walk in, he had to walk forward spreading his crotch. This was too much for his bladder and the flood gates opened. pee flooded into his boxers quickly soaking them and then flooded into his sweat pants. Hailey looked on with delight. She could see Kyle's crotch get dark and the pee crawl down both of his legs. A little puddle even accumulated on the floor. Kyle was so embarrassed. He had not had an accident like this since he was four. Anne walked in just as Kyle was finishing up. She walked up to Kyle and gave him a hug as he started crying. "It's alright, accidents happen. I didn't foresee the one bathroom as being an issue. This is my fault, I will help you get cleaned up while Hailey goes and gets your bag"
Hailey went upstairs, but she wasn't going to go get his bag, she took his bag and hid it in a little area in her closet where the dry wall was coming away behind a few of her dresses. She came back down stairs and reported that the bag wasn't there. Anne had worked fast. She had gotten Kyle's wet clothes off and had him wrap a towel around his waste and had cleaned the little puddle on the floor. Anne replied "That's strange, I could of sworn I brought it inside. Kyle was extremely confused as well because he remembered giving it to his aunt. No matter, I'm sure Hailey can let you borrow some of her clothes while yours are in the wash. Kyle panicked again, he didn't want to wear his cousins clothes, what if his friends some how found out. He would never live it down. He tried to reason with his aunt "Can I just wait for my clothes to finish in the wash". Anne replied "Nonsense, you can't go around with just a towel wrapped around your waste, and it's going to take a while. I had just started a load so I won't be able to get to yours for a while. I'm sure Hailey has some clothes that will fit you"
Hailey nodded and took Kyle's hand and lead him upstairs "Sure, I have some stuff that will fit you". Hailey was brimming with happiness, her plan was working perfectly. She was going to get to sissify her cousin. This was going to be so much fun. Hailey took Kyle into her room. Hailey had the bigger of the two bedrooms since Anne was out of the dating scene and Hailey was the only one who usually had company over. Hailey had the same room decorations since she was little. She had pink and white walls with a cute fairy border. She had various girly pictures and posters around her room like a picture of the Disney Princesses and unicorns. She had two beds in her room, one for her and one in case of guests. They were pretty much the same but had different comforters. One had princesses on it and the other had fairies and unicorns on it. She had a dresser and a table with a mirror to do her make-up. In one corner she had a changing cover with a wall mirror. Hailey sat Kyle down on one of the beds and began looking for the perfect outfit for Kyle to wear. Meanwhile, Kyle was very nervous, he knew the kind of clothes his cousin wore, She wore the real girly girl clothes. She rarely wore jeans except when she went outside to play. She wore lots of skirts, and dresses. She even still had some dress up dresses she liked to play with. Hailey got out a pair of panties. She wanted to embarrass Kyle as much as possible. She got out a pair of panties that were all pink and were made of a lacy material. It was even ruffled in the back. Kyle practically crawled out of his skin when he saw them. He pleaded with his cousin "Hailey please, this is embarrassing enough as it is, can you please find a pair of less girly underwear". Hailey saw Kyle was about to cry again and she didn't want to completely traumatize him so she conceded. She found a pair of panties that were white and pink along the waistband. It had a picture of a couple fairies playing on the front. This wasn't much of an improvement for Kyle but it was better. He was still reluctant to take them and Hailey saw this. "It's alright, there not going to bite, do I need to help you put them on" causing Kyle's face to blush beet red. He hesitantly took them and went behind the changing cover. He dropped his towel and slowly stepped in to them. As he pulled them up. He felt very strange. These panties felt really good. They were softer than his boxers and they fit around his junk better(Kyle didn't have the largest of packages). When he stepped out, Hailey started to giggle, When Kyle asked why she pointed down to his area. He looked and noticed he had become aroused by the soft material around his junk. Kyle became even more embarrassed. Hailey just said "I think someone enjoys his panties". From this reaction she worked even harder to find a really girly outfit for Kyle to wear. She finally found the perfect one. It was a light blue dress she had worn a couple of years to a wedding Kyle was also at. It fell right below the knees and it poofed out a bit at the waist. He recognized it and said "please, don't you have like a pair of jeans or something I could wear." Hailey replied "Sorry I don't wear many pairs of jeans and the pairs I do have are all too big for you, Besides, you will look really cute in it. She helped Kyle into it, and tightened everything up for him. The dress was made of very soft fabric and it felt very nice. when Hailey finished, she let Kyle admire himself in front of a mirror, He was astonished, he looked pretty but not only that, he felt more complete like the clothes were meant for him. Hailey saw that look and was happy. They definitely weren't going sledding tomorrow.
After Kyle got done admiring himself in the mirror, Hailey took him down to show Anne. When they came down stairs, Anne was preparing dinner, when she turned around, she stifled a laugh. Kyle blushed deep red after he saw this. Hailey piped up though "It's alright mom, he likes the clothing". Anne was amazed Kyle didn't protest to this comment meaning she was telling the truth. "That's great sweetie, you two can have more things to do."
After dinner, Hailey took Kyle back up to her room. After they entered, they sat down on the floor. Hailey was the first to talk "Now that your dressing like a girl, you can't go around called Kyle, that's just weird, we need to get you a girly name"
Kyle said "How about Kylie" there were a couple of girls at his school that had that name
Hailey said "That's perfect Kylie"
The rest of the evening, Hailey coached Kylie on how to be a girl. She taught her how to walk, talk and act like a lady. Kylie had so much fun she didn't even realize it was really late until Anne came up stairs to tell them they needed to go to bed. Hailey asked if Kylie could stay in Hailey's guest bed and Anne said that was fine as long as Kyle was ok with it. Kylie replied I want to. Hailey also told her mom how it wasn't Kyle, it was Kylie. Anne smiled, "Ooh is it, looks like you two have been bonding quite a bit up here."
Hailey and Kylie held hands next to each other and said "That's right, were like BFFs now"
Anne was very happy for Hailey, she had never had any real close friends. Most of her friends were temporary. Though it was a bit strange, she thought as long as both of them are happy with it, It can't be a bad thing"
Anne told them good night and went to her room. Hailey and Kylie were both getting tired so they decided it was time for bed. Hailey helped Kylie out of her dress. She went into her closet and brought out a couple of nighties. One of them was pink and the other was aqua. Hailey gave the pink one to Kylie and helped her put it over her head. Hailey then went into her closet, and was in their for a couple of minutes. When she came out she was wearing the aqua nightie. When Hailey bent down to pick up the clothes on the floor, Kylie was surprised. Hailey's nightie had crept up revealing a pull-up. Hailey saw Kylie's look and then understood immediately. "I sort of have a weak bladder, and I wet the bed occasionally, there actually pretty comfortable"
Kylie didn't see anything wrong with that, and was actually sort of jealous. She was curious at what it would feel like. She worked up the nerves and asked "Can I wear one as well?"
Hailey grinned with delight, of course you can, your in for a treat tonight" Hailey went into the closet and came back with a pull up in hand. She handed it to Kylie. She examined it for a second. It felt padded, and soft. It was mainly white except for the waistband and seams which were pink. It had the Disney princesses on it with the flowers that disappeared when it became wet. Kylie took her panties off and handed them to Hailey who put then in the hamper. Kylie then opened the pull up, stepped inside it, and pulled it up. It was a little loose at first because Kylie was a little bigger than Hailey but Hailey showed her how to tighten it up so it wouldn't leak. Kylie walked around with it for a second and it felt nice. It wasn't very padded because it was meant to be discreet but it did give her a sort of a waddle. They went down stairs and brushed their teeth and came back up stairs. Hailey gave Kylie the bed with the Disney princesses on it and Hailey took the one with the fairies on it. They said good night to each other and then Hailey turned off the lights.
Because her clothes were so soft and comfortable, Kylie fell asleep almost immediately. In her dream, Kylie dreamed she was an actual girl. she had long flowing hairs, a beautiful body, and a stunning face. She was a real princess. Hailey was in the dream too as her best friend. They wore pretty dresses and played girly games. It was one of Kylie's greatest dreams. At one point, her mind went to the thought of the pull-up she was wearing. She dreamed she wearing the blue dress she had worn that day. They were playing in Hailey's room when she felt the urge to pee come upon her. She asked Hailey if she could go, but Hailey woldn't let her because she was doing her nails. Kylie became more and more desperate until she was bursting. Finally Hailey finished, but when Kylie got up to rush to the bathroom, she almost let some out, she was forced to hold her crotch and bend over so she wouldn't leak. Hailey saw what Kylie was about to do and came up behind her and tickled her until Kylie lost it. Pee soaked through her panties and the front of her dress. It made a big wet spot on the front of her dress and it began to grow and grow until it reached the bottom of the dress and started to drip on the floor. When she finished, Kylie looked down, and inspected the damage. The front of her dress was completely soaked, and it was still dripping some on the floor. She lifted it up and saw that her panties were completely soaked as well. There was a little puddle on the floor. At this point Kylie woke up, it was early in the morning. Hailey was still sleeping. She rolled over and instantly felt something wrong. Her crotch felt really bloated. She opened the covers and looked down. Her pull-up was bloated and the flowers on the front had disappeared. Kylie couldn't believe it, she had actually wet herself. She hadn't wet the bed since she was 5. She rolled around a bit taking in the feeling. It felt pretty good. Her mind went back to her dream and she knew what she was going to do today.
She layed in bed for a bit longer until Hailey woke up, When they got up, Kylie admitted to Hailey that she had wet her nightie during the night. Hailey was overjoyed by this. Oh you are alright, that is what they are there for. I'm really glad now you wanted to try them on now. Hailey helped Kylie change out of his pull-up. They took turns taking showers. Hailey made sure Kylie used her really girly shampoos and soaps. When Kylie finished and dried off, she came back into the bed and already had a set of clothes for Kylie to wear. She had the same lacey pair of panties that she had tried to get Kylie to wear the previous day but this time, Kylie took them eagerly and put them on. The fabric felt amazing and big smile went across both girls faces. Next came a light pink skirt and a matching shirt. It made her look very cute. After Hailey had cleaned and changed they went downstairs for breakfast. Anne had made pancakes. She asked "How are my ladies doing this morning" both girls said they were great. They ate for abit. After they finished, Hailey took Kylie downstairs. Since Hailey was an only child, her mom had spoiled her. The basement was a girls dream. In one corner was a ton of barbie dolls and a doll house. In another corner was a mirror and desk set up to do nails and makeup. In another area was a couple racks filled with dress up clothes and, lastly there was an open area and a tv. Kylie was in heaven. Hailey lead her to the dress-up area, and asked Kylie to take off her skirt and shirt. She then got down a princess dress that looked like Snow White's. Kylie did as she was told. and Hailey helped her put the outfit on. It fit perfectly because it was one of Hailey's older ones. Kylie admired herself in the mirror and did a little curtsy. Next Hailey took her over to the make up area. She must have had a lot of practice because she made Kylie's face look amazing. Next Hailey painted Kylie's nails a blue that matched her dress. Hailey was halfway through when Kylie felt the urge to pee. She remembered her dream and got excited. She decided not to say anything. As they finished her finger nails, Hailey decided to paint her toe nails too. Hailey was getting a little desperate but didn't want Hailey to find out. It seemed like an eternity for Hailey to finish her toes. By the time, Hailey finished, Kylie was practically bursting. After Hailey finished, She told Kylie to wait a couple minutes for the nails to dry. Kylie started dancing in her seat, she got up so she wouldn't ruin the seat and released her bladder. Pee flooded into panties and quickly soaked through them and started soaking through the dress. Streams flooded down until they reached the bottom where they dripped on to the wood floor. Kylie was really embarrassed but also felt really nice in a naughty sort of way
When Hailey looked back and saw what happened, she began to giggle, "Oh looks like this princess had a wetsie". Hailey ran up stairs and told her mom who came downstairs. Kylie was really embarrassed and looked like he was about to cry. Hailey took him upstairs and got him out of his wet clothes while Anne cleaned up the floor. Hailey was helping Kylie out of her clothes, when Anne came in to help. Hailey went to get a clean pair of panties when Anne told her to stop, instead she went into the closet and grabbed a pull-up. "Kylie, this is the second accident you have had, and Hailey told me you wet the bed last night, It doesn't bother me that you are having these accidents, I think it is kind of cute, but I don't want to have to keep cleaning the floor and clothes". Kylie was overjoyed, She told Anne she understood and said she would try to be more careful even though that wouldn't happen. Kylie stepped into the pull-up and Hailey gave her the clothes she was wearing earlier in the morning. They went back downstairs and watched a movie, they decided to watch "Beauty and the Beast". Half way through Anne came down with some news "Kylie, your parents just called, they said they need to stay longer than they expected so you are going to stay with us for another week" Both girls were overjoyed. This meant they got spend Christmas together.
Over the next couple of days, Kylie got used to her life. She and Hailey had so much fun playing with dolls and dressing up. Kylie used her pull-up at least once a day and wet the bed every night. Hailey was getting a bit jealous of her mom babying Kylie. So one day while they were playing with dolls and dressed up in princess dresses, Hailey came up with a plan. She was wearing a Cinderella dress. She finally couldn't take it anymore and began wetting herself. She was on her knees so it was pretty obvious from the back that she wet herself. Both girls grinned and went to go tell Anne. She didn't mind at all "Looks like both my ladies, like wearing pull-ups" They all had a good laugh and Kylie and Hailey went and to go change Hailey. Both girls were having so much fun they didn't realize it was Christmas eve until Anne mentioned it. Both girls went to bed excited for the next day.
The next day both girls woke up and ran downstairs. The floor surrounding the tree was littered with presents. There were lots for both girls. Apparently Kylie's parents had given Anne money to buy gifts for Kylie. Anne walked down shortly and they began to open their presents. Kylie was so excited to see what she got. She opened her first one, it was a really cute dress. Besides this gift, she got a couple of barbie dolls and plenty of clothes to dress them with, Some dress up clothes, and a lot of cute clothes to wear out. Both girls got everything they wanted. After they finished, they took all the gifts upstairs to play with. Both girls could not have been happier. They both had become such good friends and Kylie had discovered his true self. Anne had told Kylie's parents about his transformation, and they didn't seem to mind it too much. They thought it was kind of cute and Kylie's mom had secretly always wanted to have a girl. Before they knew it, the week was up and Kylie had to leave. When Kylie's parents first saw their "daughter" they were a bit surprised but they had been told ahead of time so they had already prepared and were happy to embrace their transformed child. Kylie and Hailey were very sad to have to say good bye. Both Anne and Kylie's parents saw this and decided they couldn't separate this friendship. There was an open house down the road a bit. Kylie's parents decided they could easily make the move down there. Kylie's parents had plenty of money and were sure they could find jobs there. When they told Kylie and Hailey they were really happy. They had to leave each other, but it would only be for a bit. They could be best friends still. As they left, they both looked and anticipated all the fun they could have living so close together, and fun is what they had, and they lived happily ever after