Alex - teen boy to baby girl

5)school on holidays

Alex woke up feeling the familiar dampness between his legs. He sighed and peeled back the blankets to assess the damage. As he feared, his pull-up was wet, and he groaned in frustration. He dragged himself out of bed and trudged to the bathroom to get cleaned up.
After he finished, he headed down to the kitchen for breakfast. His mom complimented him on his nightdress, which was a rare occurrence that made Alex feel good about himself. Elly, his younger sister, called him "baby sis," which was a common taunt from her that he had learned to ignore. However, Alex's mom and aunt paid no attention to Elly's teasing, brushing it off as just little sister behavior.
As they ate breakfast, Alex's mom and aunt discussed the possibility of getting him thicker protection, as his pull-ups had almost leaked twice now. Alex's face went red with embarrassment at the thought of being put into diapers.
After breakfast, Alex's mom helped him change into his clothes for the day. They were girly but smart, which made Alex feel awkward, but he didn't say anything.
When they arrived at the "school building" that Alex's mom had mentioned earlier, Alex was surprised to see it was a real school building. It was summer, but the halls were bustling with activity. Alex's mom led him to a classroom where they were met by a teacher who split the students into two groups based on age and potty training level.
Alex was relieved to find that he was put into Group 2 with his sister Elly. However, he noticed that some of the kids in Group 1 looked much older than he expected. The policy was that any child who was not fully potty trained had to be put into Group 1, regardless of their age.
As they settled into their classrooms, a girl named Emily caught Alex's eye. She smiled at him and he blushed, feeling a strange sense of attraction. He noticed her painted nails and complimented her on them, to which she smiled and thanked him.
Throughout the day, they had sports and art activities, access to the library, and a game area. It was like a daycare, but with a more structured curriculum. Alex found himself getting into the games and even becoming a champion at one of them.

Alex was beaming with pride as he walked back to his seat, clutching the trophy he had just won for being the champion of the game. However, as he sat down, he felt a sudden warmth spreading between his legs, and his heart sank. His pull-up had leaked, leaving a visible wet patch on his skirt. He tried to cover it up with his hands, but the damage was done.
As the day went on, Alex was put into Group 2 with his cousin Lisa and her friend Ella. It was the group for kids who weren't potty trained, and Alex felt a sense of embarrassment as he was forced to wear a diaper. They spent the day finger painting and playing with dolls, which Alex found dull. He tried to play with the boys instead of the girls, but they rejected him.
After a while, one of Lisa's friends invited Alex to a princess-themed birthday party, and he jumped at the chance. When it was time to leave, Alex's mom picked him up and took him to his aunt's house. He tried to join in the games with his sister Elly and cousin Jess, but they left him behind, forcing him to play a kid-friendly game on the PlayStation with Lisa.
For dinner, they had pasta, and Alex found himself struggling to eat with the bib and sippy cup that his aunt insisted he use. His sister teased him, but he was too embarrassed to protest.
As the night went on, Alex stayed in his diaper, using it for its intended purpose. He thought about asking to be let out, but didn't bother. Eventually, he was changed into a fresh diaper and put into a nightdress. He watched TV programs with Lisa until bedtime, where he said a quiet hi to Emma when she took Lisa's bedtime bottle out and replaced it with a pacifier. He noticed there was a teddy on the bed for him, which he placed at the bottom. It was an earlier bedtime than the girls, but he was too tired to care.