Teenage Rebellion

As a young boy, Jeremy had always been fascinated by the way his mother styled her hair. She had long, flowing locks that she would straighten and curl to perfection, often spending hours in front of the mirror to get the perfect look. Jeremy always envied her hair and makeup and wished he could do the same, a feeling he made sure to keep bottled up.
But as he entered high school, Jeremy found himself increasingly drawn to embrace his desires. He began to experiment with different hairstyles and looks, much to the dismay of his mother. She preferred that he keep his hair short and neat, believing that it was more appropriate for a young man.

Despite her protests, Jeremy was determined to grow his hair out and try the styles he desired from childhood. He loved the way this his hair felt along his neck, and eventually draping over his shoulders.

One person who particularly appreciated Jeremy's long hair was his girlfriend, Emily who had encouraged him to grow it out. She loved playing with his hair when he would come over after school, often straightening it and tying it into a high ponytail before making out with him. She loved the time she spent straightening his hair, not only did it give them time to talk and catch up, but it also secretly turned her on.

The process of straightening Jeremy's hair was a time-consuming one, but Emily didn't mind. She usually started by wetting and detangling his hair, taking care to remove any knots or tangles. She then applied some heat protectant cream in his hair slowly brushing it through. Finally, after drying his hair, she divided it into small sections, using clips to keep each section separate.

Next, Emily took out her flat iron and straightened Jeremy's hair, starting at the root and working her way down to the ends. She took her time, making sure to straighten each section evenly and carefully.

As she worked, Emily would often chat with Jeremy about her day, or share stories and jokes to keep him entertained. Jeremy loved spending this time with her, and always looked forward to her styling sessions.

Once Emily had straightened all of Jeremy's hair, she would carefully brush through it to remove any remaining tangles or knots. She would then gather his hair into a high ponytail, securing it with a hair elastic.

Jeremy loved the way his hair looked after Emily had finished styling it. It was rare that any of his friends would see him like that but on the few occasions that they did, he got great feedback. He was grateful to have such a supportive and loving girlfriend, who unknowingly helped him fulfill his secret fantasies.

Despite his mother's initial reluctance, she started to appreciate his hair too. When he would come home in the evening, his hair looked cute styled in a sleek high ponytail.

One day, after doing his hair and making out with him, Emily suggested that Jeremy try wearing makeup to enhance his features. He showed a bit of hesitation, but on the inside, he was thrilled. Emily helped him choose the right shades and taught him how to apply the makeup, and he was amazed by the transformation.

That night he went home wearing the makeup and his mother remarked that he looked nice. Although she preferred her son to look like a man, she had come to realize that he was coming into his own and let him embrace his personality, hoping this would just be a phase.

But it wasn’t a phase, Jeremy continued to try on make-up and explored more feminine hairstyles, coming home some days with is hair in a French braid or tight ringlet curls. One day, after braiding his hair in twin pigtails, Emily added in a pink barrette and told him to try on a baby blue dress. He did as he was told and was in awe when he looked in the mirror. He looked like a teenage girl. Emily couldn’t control herself. She threw herself on top of him and started to make out with him. She took her clothes off and decided today would be the day she finally did it. After a monumental awakening for both of them, Emily and Jeremy cuddled on the bed.

Emily told Jeremy that she is bi and would prefer him to be his girlfriend. After that session, he wanted nothing more than to be with her. They decided that the name Jenna seemed more fitting. As Jenna walked back home still wearing the dress with her hair in braids, she decided that she would come out to her mother. Dinner that night was a difficult conversation as her mother realized this was not simply a teenage rebellion.