by Daring Diane
Copyright © 2016 Daring Diane
It was near the end of sophomore year in high school. Terry sat down at the lunch table next to Marcy. Soon, Lily and Susan joined them. They chatted about classes and the latest gossip. The boys from their class were envious. They all wanted to spend time with Marcy, Lily and Susan. Terry did not look that out of place at the table. But, there seemed to be some disagreement lately.
You see, Terry was a boy. He had longer hair and unlike most of the boys, he took good care of his hair. His mom required him to take good care of his hair or she would get his hair cut. Terry was one of the brighter students in the class and he had been friends with the girls since they were in first or second grade. They all lived within a block of each other and they had been playmates throughout the years.
As school became more difficult, Terry was clearly one of the smarter kids in the class. He and the girls started studying together. The girls knew that Terry was helping their grades and they were all old friends. And, as many girls pushed the boys away Marcy, Lilly and Susan discussed Terry. They decided that Terry was their friend and they saw no reason to push him away.
Thus developed a strange exception to the separation of the genders attitude in the class. Terry was the only boy who had a friendly non-sexual, non-dating relationship with girls in the class. Some of the boys were envious. Others assumed Terry was strange. But the girls made it clear that anyone badmouthing or picking on Terry was persona non grata. They held sway with many other girls in the class.
Terry had few male friends. He spent much of his free time reading and studying. Since most of his conversations were with the girls, Terry found that he was pretty much up to date on a variety of topics most of the boys knew nothing about. He knew a lot about hair care, skin care, and which traits and personal characteristics the girls liked about boys. He knew about fashion and style and the girls had come to rely on him for advice on matching certain outfits and how to avoid some bad looks. Hanging out with the girls, Terry found he expressed himself much like the girls did. Terry was animated when talking and he used his hands and his body when telling stories or discussing things.
Terry tried to incorporate some of this knowledge in his own personal presentation. In addition to taking care of his hair, Terry had adopted a nightly ritual of skin care. While he had little body hair, Terry had a razor that he used to eliminate any hair on his legs that tried to grow. He liked the smooth legs he and the other girls had. He brushed his hair nightly before bed.
At Christmas over their freshman year, Susan gave everyone the same present. Marcy and Lily loved their present. Terry was unsure. Susan had bought them all three pair of matching panties. Susan said this would allow them all to have a secret way to match that no one would know about. The panties were simple cotton spandex hipsters with no lace. Just three brightly colored pair of panties.
Terry stared at the underwear. Susan told Terry the panties were made of the same material as his own regular underwear and that this could be their little secret. No one would ever tell. When they were going to have a matching day they would plan it ahead of time.
Terry’s mom thought it was a strange gift. But she agreed, that Terry had other underwear with no fly that was essentially the same. She told Terry to do whatever he wanted. He should not feel bullied and she was sure the girls would understand if he did not want to wear the panties.
Terry took his gift to his room and decided to try the underwear on. Terry was amazed by how comfortable he found the panties. They stretched and fit him like a glove. The spandex tended to compress his male appendage. But, he found it surprisingly comfortable. He decided to keep them on for the rest of the evening. Terry had taken to sleeping in long oversized t-shirts. That night, Terry slept in his new panties and he fell asleep with a secret smile on his face.
The day after Christmas, Terry donned the royal blue panties Susan had asked everyone to wear. He loved the feel and he slipped his jeans on. Terry and the girls had decided to go to the mall to see a movie. At the multiplex they got drinks and popcorn before moving to their theater. The group sat down with Marcy on the left, then Terry, Susan and Lily. There were not people near them. Susan asked Lily if she was wearing he blue gift. Lily nodded and thanked Susan telling her she really like her gift. Susan said, “What about you Marcy?” Marcy said she agreed with Lily. She thought it was really a cool idea for them to have a kind of secret pact between them.
At that point, all eyes came to rest on Terry. Terry felt cornered and he began to blush. In the lower light, his blushing was less noticeable. The girls could not tell how to interpret his looking at the floor.
Marcy bumped his shoulder, whispered in his ear and asked whether he thought the blue ones were tighter than the others. In his tense state he didn’t realize his mistake until he said, “No.” with a questioning look on his face.
Suddenly, all the girls dove on him in a group hug. Terry wanted to cry because he was embarrassed. But, the girls were laughing and started tickling him. Soon they were shushed by some theater employee. With the tension released, they knew their little group was still holding together. And they all had a secret. As the movie began, they all had big smiles on their faces and they held hands.
Over the next few months, Lily and then Marcy each added their own contribution to the secret panty club. Marcy’s contribution in February were red panties with hearts on them. Terry’s mom thought it was cute but maybe a little girly. Terry was embarrassed by the hearts and he wondered if the girls were trying to push him out of his comfort zone. Terry and the girls would coordinate their underwear a couple of days a week and especially if they were going somewhere together. No one but his mother ever saw his underwear so Terry became more comfortable with his new treasures.
In March, Terry told his mother he wanted to make his own contribution to the panty club. He asked her to help him. Terry and his mom went to the mall and Terry was very embarrassed when they entered the lingerie section of the store. Of course, he had been there with his mother before. But today he knew he was there to buy something for himself and his friends.
Terry had told his mom that he wanted to get something in a Kelly green for St. Patrick’s Day. Terry was astounded by the number of choices and options. They found a bunch of different styles and designs for his holiday panties. Once they started looking at the choices in green, Terry all but forgot everyone around him. He and his mother sorted through several choices before deciding on some hipsters with a white base and really realistic green shamrocks in different sizes printed all over. As he and his mother gathered up the four pair he needed for his panty club contribution, he spied a simple green pair of panties. He picked them up and sort of pushed them to the side. He fingered several other pair before sliding a baby blue pair to the same place.
Terry’s mom had stepped to the side and was pretending to be interested in something else. She asked over her shoulder if Terry was ready to check out. Terry seemed enthralled. His mother had to ask the question a second time. Terry seemed unsure how to answer. Terry’s mom stepped up next to him and said, let’s get checked out. As Terry turned he kept staring at his little pile until his mom reached down and scooped up his extra two pair of panties. No words were spoken, but Terry looked like he was going to cry.
Terry’s mom was excited to buy him something he really wanted. They checked out and she handed the bag to Terry to carry out of the store. Terry held his mother’s hand and they strutted out of the mall.
The girls exploded in glee when Terry presented his contribution to the panty club. Terry was more excited because he had worn his new baby blue panties that his mother had bought for him. It was his little secret. The girls knew Terry was a full-fledged member of the panty club and over time, each of them would periodically make a new donation to the club. It got to the point where the group wore their club panties on 3 or 4 days a week.
With his mom, Terry acquired some simple white panties that were very similar to men’s white briefs with no fly. Of course, they were a little tighter. But Terry virtually gave up on men’s underwear.
During afternoon study sessions the group would take breaks. By sophomore year, during some of these breaks, the girls started discussing different ways to enhance their looks. They often practiced on each other. This included testing different makeup and plucking stray hairs from their partner’s eyebrows. Terry had been reluctant at first. But, he allowed the girls to clean up his eyebrows which they insisted was something many men did. When the girls wanted to try different techniques for makeup, Terry offered his opinion. Then the girls tried different things on him once in a while so he wasn’t left out. Terry enjoyed these sessions because he felt like he belonged to the group.
To tell the truth, Terry was fascinated by how much the girls were able to change a person's appearance with careful application of makeup. He was intrigued that with changes in makeup, a person could totally change their looks.
Terry and the girls all had hair that was longer than shoulder length. Terry had let his hair grow and he was able to do a lot of different things with his hair. Unluckily, he could only experiment at home or with the girls during their time together. He had to be careful at school. He didn’t want to be picked on or ostracized. Terry kept his hair in a simple ponytail most of the time.
Terry’s fascination fueled his curiosity and he often found himself participating in their sessions of makeup experimentation, as well as their hair styling sessions and Terry found he enjoyed himself. Secretly, Terry often thought about these sessions with the girls when he was home at night. He tried not to let the girls know how much he really enjoyed their study breaks.
The girls were fascinated with the boys in their classes. But most interaction was in the form of groups of people hanging out with other groups. Sometimes people would pair off within the group. Yet, none of them were committed to any individuals. Terry sometimes went with the groups and there were always extra people around. Terry had not found a person he wanted to date. But, he wanted to be part of the group. The group would go to movies or local activities as well as school sports and after school activities. Marcy’s older brother Brad would often accompany the group when they went out. Terry liked talking to Brad. Brad always seemed to enjoy talking to Terry and the girls. He had a really good relationship with his sister.
The parents, including Terry’s parents, kept a close eye on the kids and their relationships. They were fascinated by the close friendship the kids had developed, but they were wary of a potential intimate relationship developing. As long as they were all just friends, the parents were happy to allow them to work together and spend their time as a group.
The four kids constantly moved from house to house and all the parents had become good friends. Terry’s parents were a little worried about his adoption of certain feminine habits. But they constantly talked to him and they were comfortable that Terry was happy and reasonably well adjusted. Terry’s mom was proud that he took care of his appearance. Terry’s dad was worried that he did not seem to be the bull in a china shop that many of his classmates had evolved into as they entered puberty. But, Terry’s happiness and his close friends made them comfortable that he was a good kid.
Terry and the girls were all about the same size physically. The girls had all developed breasts and were actually a little taller than Terry. But, Terry’s parents were not tall and in the end they would probably all be about the same height. Since the kids were all pretty skinny and with their long hair, they all looked like little clones. They had individual characteristics, with slightly different hair colors, and the girls obviously had breasts. They could even wear each other’s clothes.
For years, the kids would have sleep overs and they would take turns staying at everyone’s house. Marcy’s mom always baked fresh cookies when they slept over. Lily’s mom and dad always had a huge breakfast including waffles. Terry’s parents had a theater room in their house and the kids would watch movies and play video games while his parents provided fresh popcorn and pizza. Susan’s parents were laid back and let the kids raid the snacks and provided enough oversight to ensure there was nothing bad happening.
Terry’s mom was taken aback when he returned from one of their overnights freshman year and sheepishly asked if she had some nail polish remover. Terry’s mom sat with her son and while she helped him clean up his bright red toes, Terry regaled her with stories of the fun they all had the night before. She was surprised he let the girls polish his toe nails. She was more surprised to find that having spent a long time on their technique, the group decided that Terry was the best at doing their toes.
Terry seemed quite proud that the girls thought he was the best. Terry’s mom asked questions and delved into their relationships to determine if he felt out of place. Terry explained that they were all just friends and while these activities may not be what most of the boys in his class were doing, he was having innocent fun with his close friends. He begged his mother not to blow things out of proportion. He said, it wasn’t like nail polish was going to do something to him.
Terry’s mom suggested that if he was going to experiment with nail polish, he might consider clear polish since no one would notice it. His nails would look nice but it would not be as obvious as some bright color on a boy. Terry thought that was a great idea.
In the warmer weather, when the kids were dressed casually, they all often wore shorts and t-shirts with sandals or tennis shoes with shorty socks. The girls now wore a bra under their shirts or they would wear a camisole or tank top with a built-in bra. Terry had taken to wearing a tank style t-shirt with a racer-back under most of his shirts. Even when he wore a tank top, he usually paired it with another tank top.
People who did not know them often assumed they were just four girls out for the day.
A couple of the mothers had enrolled their girls in dance classes when they were younger. However, none of them really stuck with it. Terry had been fascinated with the Olympics and during seventh grade he convinced his mom to enroll him in a local class that taught gymnastics. Terry was not good enough to ever compete in the Olympics. But he enjoyed the classes and eventually he convinced the girls to join him. The classes were made up predominantly of girls but there were other boys in the classes. The kids had taken up walking and running during their freshman year. They participated in local charity walks and they always went as a team.
During their first two years in high school, Marcy had periodically brought up the idea of trying out for the cheerleading squad. Her mother had been a cheerleader and she thought it might be fun. During their early high school, the group believed that it was not worth it since the squad was mostly seniors and juniors.
However, in the early summer between sophomore and junior year, the girls began to more seriously consider trying out for the cheerleading squad. Terry encouraged his friends telling them that with their gymnastic experience and the constant running they all did that they would be shoo-ins for the squad.
The girls decided to consider trying out and Marcy’s mom got examples of the cheers the school wanted them to demonstrate to try out for the cheerleading squad. The girls and Terry decided to try and spend a few hours every other day practicing the different cheers and tumbles. They would practice in one of their back yards. Terry watched the first day and offered advice. After an hour of Terry’s healthy criticism, the girls demanded Terry demonstrate their failures.
Terry worked through several aspects of the routine and showed them what he perceived as errors in their transitions. He showed them how he thought the existing squad did different cheers. The girls were surprised with Terry’s observations and his demonstration. Terry became the teacher helping them all to understand the routines and perfect their performances. The parents at whoever’s home they were practicing would stare out the window as Terry helped the group perfect their routines. Terry was clearly in his element.
The school had tryouts for football and cheerleading before the fall semester started. Marcy’s mom scheduled them to try out for the squad and arranged to drive everyone over on the day of tryouts. Two days before the tryouts, Marcy’s mom went by Terry’s house and talked to his mom. All of the parents agreed that Terry was really good at the cheerleading routines and Marcy’s mom wanted Terry to try out for the cheerleading squad with the girls. Marcy’s mom explained that there were lots of schools with boy cheerleaders and she thought it would be fun for all four of them to have something else they could succeed at.
Terry’s mom talked to him about trying out for the cheerleading squad. Terry didn’t know that boys could be cheerleaders. Terry’s mom pointed out that several presidents of the US had been cheerleaders. Terry found himself getting excited about trying out for the cheerleaders and called Marcy and the girls to get their opinions. The girls let him know they thought he was the best at the routines and they joked that they were worried he would make the squad and they might not.
The group gathered at Marcy’s house that night and they decided that they should all dress in similar outfits for the tryouts. It would be sort of like they were their own little squad. They agreed to wear black bike shorts and they all wore the same school t-shirt. The girls wore black sports bras under their shirts and Terry wore a black racer back tank top with a styling that looked similar to the sports bras the girls were wearing. Marcy’s mom had them all wear their hair in a ponytail to keep their hair under control.
Marcy’s mom watched several other groups of girls trying out for the cheerleading squad and it was clear before Terry and his group began that they were going to outshine most all of the new applicants. Terry and the girls performed their routines flawlessly and did it in sync with each other. The coach and the senior girls were clearly astounded. Marcy’s brother Brad and a few of his fellow football players who had been working out nearby stopped to stare at the tryouts.
At the end of the tryouts, the coach said they would meet and contact everyone to let them know who was accepted for the squad. Marcy’s mom was overly confident that their performance was the highlight of the morning. Brad ran over and congratulated Terry and the girls on their performance before returning to practice. Marcy’s mom took them all out to lunch to celebrate.
Marcy’s mom called all the other parents to let them know how well the tryouts had gone. She was not surprised to get a call from the cheerleading coach telling her Marcy had made the team. She quickly confirmed that all four had made the squad.
Terry and the girls were all at Lily’s house and Lily’s mom reported excitement and yelling when they found out they had all made the squad. Terry had not been sure he wanted to make the squad. But, he was overwhelmed with happiness and accomplishment when he found out he had made the squad. Lily’s mom reported that Terry seemed more excited than the girls if that was even possible.
About a week later, Marcy’s mom took Terry and the girls to school to pick up their new cheerleading uniforms. The girls couldn’t wait to get back to Marcy's house to try on their new outfits. Everyone ran up to Marcy’s room. Terry could not wait to see what his uniform looked like. He paused as Marcy ripped the bag off her uniform and tossed everything on the bed.
Everyone paused and watched to see what was there. Marcy grabbed a sheet of paper and read it as she checked things out. There were the gold Cheerleading panties and a short pleated skirt in the school’s blue. When the pleats opened up there was a gold stipe inside the pleats. The top was a white sleeveless top with the school mascot on the front. Marcy’s name was on the front of the top just above her left breast. There was a gold sports bra along with two pom poms in blue and gold and a scrunchie for long hair.
Marcy read the sheet out loud. “Cheerleaders must wear a sports bra supplied by the school as part of the uniform. There are no exceptions. In previous years, squad members wore revealing clothing and this rule was adopted to maintain consistency and decency.”
Lily and Susan dove into their uniform bags. Marcy’s mom guided Terry across the hall to the bathroom so he could change in privacy. However, she helped Terry open up his uniform before he closed the door. Terry did not understand. He had the exact same uniform as Marcy including the sports bra. There was a note from the coach that said, “Terry did not provide a bra size. I assume Terry does not wear a bra but since it is required, I provided one with an A cup in Terry’s chest size.”
Terry looked at Marcy’s mom. Marcy’s mom chuckled. She looked at Terry and he had a really concerned look on his face. She said, “Terry, the coach ignored the form and didn’t realize you are a boy.”
Terry was upset but saw some of the humor. Marcy's mom got a conspiratorial look on her face.
“Terry, you should put it on and surprise the girls. You guys can go out in the back yard and practice your cheers. We’ll get this worked out with the coach tomorrow. Let’s have some fun.”
Terry was reluctant. But it did sound like fun. And, the uniform had his name above the left breast.
Terry closed the door and pulled off his clothes. He pulled the sports bra over his head and slipped on the cheer panties. He donned the top and admired his name. He pulled on the skirt and everything fit perfectly. Terry really liked his outfit. He looked in the mirror and could hardly take his eyes off himself.
Terry heard the girls calling him. They wanted to go out in the back yard and get some pictures in their new uniforms. Terry told them he would be down in a few minutes.
The girls were waiting in the back yard practicing cheers. Marcy’s mom was waiting in the hall. When Terry opened the door, she was floored. He looked great. Even without breasts, Terry looked all girl and he was going to be a heartbreaker. She quickly combed his hair and pulled the cheerleader scrunchie onto his ponytail.
When Terry walked out into the back yard with his pomp oms, the girls stopped dead. Their eyes went wide. Lily screamed, “Terry, you look great.” All the girls ran over and there was a group hug.
Marcy’s mom took several pictures. The group practiced their cheers and tumbled around in the yard. Marcy’s mom videotaped some of it while taking pictures.
Soon the group needed a break. Marcy’s mom invited everyone in for a snack. Terry had forgotten about his clothing. Marcy and Susan were helping Marcy’s mom prepare a snack. Terry and Lily were in the family room. Lily excused herself to use the facilities.
Terry was looking at a magazine when Brad appeared from upstairs. Brad sat down next to Terry.
“Hey, Terry I was watching you guys doing your cheers from upstairs. You really look great in your new uniform.”
Terry was suddenly aware he was wearing a skirt and sitting next to a boy from school. He started to get up. Brad pulled him back down onto the couch.
Terry looked up at Brad. Brad said, “Terry, you are like a flower and I have been waiting for you to bloom. You’re beautiful you know.”
Terry didn’t know what to say. He just stared at Brad.
Brad said, “Terry, since you are now the prettiest cheerleader at our school, I was wondering …”
Terry cut him off but asked in a quiet voice, “Did you say I was the prettiest cheerleader at the school?”
Brad smiled. “Well in my opinion and that of any sane person you are.”
Terry was speechless again.
Brad continued, “As I was saying, do you think you might go out with me sometime?”
Terry was confused again, “On a date?”
Brad smiled broader, “Of course, on a date. I’m sick of us just hanging with the group. I want to spend some time with just you and me.”
Terry asked, “Did you say I was beautiful?”
Brad nodded, “I did. Beautiful and the prettiest.”
Terry sputtered, “But, but …”
Brad had slipped one of his hands behind Terry’s head.
Brad said, “Terry I always knew you were beautiful. I have trouble thinking of anyone else. I dream about you. Most importantly, I have yearned to do this.”
And with that, Brad supported Terry's head, leaned over and kissed Terry on the lips.”
Terry’s mind was on overload. But all Terry could think about was how soft Brad’s lips were and how Terry hoped this kiss would last forever.
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