Cheerleader- Boy for the Cheer

by Daring Diane

  Sally followed behind Lee and pulled the ones he liked. When she had gathered four, she said, “Come over here for a minute.”

  Sally led the way over to the dressing rooms. Stopping, Lee was right behind her. There were few other people in the store and no one in the dressing rooms. Sally opened the door and pushed Lee towards the dressing room. As he realized what she was doing she forced the four tops into his arms. The door was closing as she said loudly, “Try those on honey and I’ll get a couple of more. Set aside the ones you like and you can show me.” Lee realized as he heard her voice that she was walking away.

  Standing alone in the dressing room, Lee did nothing for a few moments. Not feeling like he had a lot of alternatives, Lee pulled his t-shirt off and pulled on the first top. After trying on all the tops, he heard his mother say, “Which ones do you like?”

  Lee put on a long sleeve black satin blouse. The collar was thin and long sleeves had extended cuffs. The fitted shirt looked and felt perfect. Lee had never owned a shirt quite like it.

  A second periwinkle top made of a light weight material and a simple open neckline had short sleeves and the sleeves were ruffles off the shoulder.

  Sally loved both tops. She stepped behind Lee and picked up the black blouse and the t-shirt he arrived in. “Lee, come on up front with me.”

  At the checkout counter, she spoke to the girl while pointing at Lee, “Lee is going to wear this top out. I’d like to pay for it and this lovely black blouse.” So saying, she handed the black blouse to the girl and asked Lee to stand closer so that the tags could be removed from his top. Lee was still in a bit of a fog as he moved up to the counter and had the tags cut off.

  After she paid, Sally led the way out into the mall. “You’re right Lee, that top is perfect. And with your light blue camisole the periwinkle is perfect. Now, I think we are ready for some serious shopping.”

  The two of them headed to that haven of femininity, Victoria’s Secret. As they headed in, Lee slowed down. He was scared to death. “Come along honey. There is nothing to be afraid of.” Sally was pulling Lee’s hand and led him into the store.

  Lee felt like a child in a candy shop. He loved the new underwear he had been wearing and he was standing in heaven.

  Sally took Lee to an area of tables covered in every variety of panties imaginable. Sally and a cute young saleswoman proceeded to explain all the different types of panties and discussed the different materials. The saleswoman highlighted some of their most popular sets which included panties, bras, and camisoles.

  Suzy, the salesgirl, asked what kinds of panties Lee liked. Lee said he wasn’t sure. So she asked if there were some he did not like. Lee explained that while they were cute, he was not ready for thongs. He did not feel like the cheeky panties with lace on the butt were what he was looking for. He also begged off on high waist panties.

  Lee finally decided he preferred their hip hugger style and a few of the bikini styles. Sally watched as different styles and colors were reviewed and tossed in different piles. Lee seemed to be having more fun with each passing moment. His smile and enjoyment filled her heart. After a suitable amount of time, Sally suggested that they look at matching accessories.

  Suzy asked Lee what size bra she wore. Not wearing a bra, Lee had no idea what to say. Sally jumped in, “Suzy, I’ve had trouble convincing Lee to wear a bra. Lee is embarrassed because there is nothing for the bra to hold. Do any of the matching sets come with training bras or maybe a padded a-cup?”

  Lee was now staring at his mother. “Mom, I don’t need a bra.”

  Sally jumped in, “See what I mean.”

  A smiling Suzy said, “Be right back.”

  Returning, Suzy explained, “Lee, your body is exactly what all the Victoria Secret Angels have. You are slim and slightly developed. All of our camisoles and slightly padded camisoles will look perfect on you. Also, we have all kinds of bras. I have several here. Let’s get you into a dressing room.”

  Lee wasn’t sure why they were looking at bras or even the camisoles. But moments later he found himself in a dressing room where his mother was helping him off with his top. His camisole followed. Suzy was standing behind him to protect his modesty she said.

  Lee was standing topless in a dressing room with a bra hanging from his shoulders while some young girl was fastening the clips and adjusting the straps on a periwinkle bra which looked like it was made to match his new top. The bra grabbed whatever flesh was in his chest area and captured it behind mildly padded cups giving the impression of budding breasts. Scared to death, Lee suddenly felt a bit light-headed as he realized he loved the bra. It was wonderful. Moments later, Suzy pulled a soft camisole with thin straps over his shoulders. Unbelievably, it was better than wonderful.

  Lee was smiling at the mirror and turning back and forth. Just as he was getting comfortable Suzy pulled his camisole off. She was undoing the bra and slipping it off. A different style bra was being slipped up his arms. This ritual continued as Suzy slipped one bra after another onto Lee.

  After reviewing many of the different styles and matching options, Suzy left to let Lee get redressed. She did suggest that at Lee’s age, maybe she should wear the periwinkle bra with her top since they matched so well. Sally agreed and helped Lee add his new bra before getting dressed.

  As they re-entered the store, Sally headed for the pajama area. Lee found himself overwhelmed again. Sally pointed out some satin pajamas and another pair of a super soft material. After Lee identified the patterns he liked, Sally added them to their pile. At first Lee had thought this was all a fun shopping exercise where they could go home and talk about it for a long time to come. However, when his mother dropped a pile of panties, bras, camisoles and pajamas on the counter, Lee realized his mother intended to actually purchase these items. The total was overwhelming. Lee hoped that after they talked, his mom could return lots of the items. It was too much money for his personal fun.

  Lee and Sally walked out into the mall carrying their VS bags and a bag from the first store. Lee looked at all the bags and looked at his mother.

  Sally looked back with a huge smile and said, “Isn’t shopping fun? I think it is time to get serious. Didn’t you say something about needing some new jeans?”

  Sally’s expectation regarding jeans was apparently different than Lee’s. Because the store they entered next had lots of jeans. They just had nothing for boys. Sally directed Lee to a display of skinny jeans. She showed him the high-waisted styles, mid-waist and low rider jeans. There were skinny jeans and loose jeans. Lee knew he would have to try the pants on to know if they fit.

  Soon, he was again ensconced in a dressing room. Shoes off, he pulled on several pair of jeans. His mother came in to help. The skinny jeans needed a little help to get all the way up. Lee decided he liked the low rider jeans in a skinny style and a mid-waist style of a looser fit in the legs. His mother sent in a couple of casual blouses of very soft materials. Lee loved them. Leaving the store, Lee wondered where their next adventure lay. Already laden with bags, Lee was taken aback when his mother turned into a shoe store.

  A while later, they left with a cute pair of black flats which might have been hard to distinguish from some men’s loafers. The heel and tapering design were giveaways but many people might not take time to notice. The more thrilling thing was a pair of boots which rose above the calf. The heel was low and the design was not overtly feminine. However, there were few men’s boots designed like these boots.

  Stopping in a mall jewelry shop, Sally was looking at jewelry. She asked for Lee’s opinion on several items. Lee told her what he liked and assumed foolishly that the items were for his mom. As the sales clerk asked Lee to sit in a chair, he did so without thinking. His mom placed several bags in his lap. This kept Lee occupied trying to hold the bags. His mother and the clerk were standing near him and his mother pulled his hair behind his ears. She took a couple of barrettes and placed them over his ears to hold the hair. Lee wondered w
hat was next when his ear was pinched and there was a pop. Less than 30 seconds later it happened on the other side. Looking up, Lee saw his face. His hair was held with silver barrettes or clips of some kind and there were little balls in his ears on both sides.

  His ears were pierced. As he looked at her and was getting ready to explode his mom beat him to it, “Lee, now you can wear your cheer squad earrings with your pendant.”

  That caused Lee to think about what she said. She said he could wear his cheer earrings.

  The clerk interrupted his thoughts, “You are on the cheer squad. I loved cheering when I was in school. I didn’t go to school in this area. I just moved here.”

  Lee needed to get away from this clerk. He stood up. His mom paid and bought a few other earring sets in gold balls and some hoops. As she paid, she said, “I have lots of earrings I don’t wear anymore. Now that your ears are pierced, you can borrow them.”

  Lee walked in a kind of trance as his mother kept talking. They made their way out to the car and put everything in the back. They stopped at a restaurant to grab some dinner.

  Guiding them into the dining area, the hostess remarked, “I have a lovely table for you and your daughter.” Lee said nothing as he tried to process all the days’ purchases. He stared at the menu and still had no idea what restaurant they were in. Sally finally got him out of his subconscious and pointed at the menu. Lee picked something and they were able to order.

  Sally started talking to see if Lee was listening. Finally, she said, “Lee, I really enjoyed shopping with you today. I think you will love your new pajamas. They looked really comfortable. Don’t you think so?”

  The question triggered something that brought Lee out of his thoughts. “I’m sorry. What did you ask?”

  “I asked if you thought your new pajamas would be comfortable. I also said I had a good time shopping with you today.”

  Lee thought about that, “I’m a little out of sorts. But, I have to admit, I had a great time. I’m just trying to figure out why you bought all those clothes. When will I wear them?”

  “Well, let’s see. I would think jeans would be something high school students might wear to school. I guess the ruffles on this top might be a little much for you and school. But maybe nice for around the house. There is no reason you can’t wear a black button shirt to school or out on the weekends. The same can be said of the other tops we bought with the jeans. I doubt any of your friends would realize the store where they were purchased. If anyone is in your bedroom examining your pajamas, we probably have bigger problems. Boys and girls both wear earrings and I suspect your new shoes are indistinguishable from what others are wearing. I guess that leaves underwear. You wear similar underwear today. Now, you just have a bigger selection. You wear camisoles today, now you have more. The only remaining thing is your new bras. I love your new bras by the way.”

  Sally paused to see what Lee had to say about her review of things.

  “I love the new things. I won’t deny it. But, when will I wear all those bras?”

  “Honey, when you are in certain situations, a young lady needs to wear a bra to maintain their modesty.”

  Lee pondered that for a moment, “Mom, what makes you think I will be in those situations?”

  “Honey, you may have already been in those situations. You are hanging out with a bunch of girls and you may find yourself in situations where a boy is not welcome or allowed. If that is the case, you may need to alter your image a little. Also, I think you did a nice job on the underarms. But, I hate to tell you this. You are going to need to shave your legs from the top all the way down to your ankles. You are going to wear shorts to the competition and you have to have clean shaven legs for that. It is a requirement. You should just accept it and start adding it to your daily grooming.”

  “I thought we were talking about bras. Which I might add is not something I thought I would ever be talking about. And now we are having me shave my whole body. I don’t really have a problem shaving my legs. I think it will look better and the girls talk about how nice it is to have their legs freshly shaved. One of the older girls had laser hair removal on her legs so she doesn’t need to shave. Everyone thought that was really neat.”

  Sally smiled, “Great. I guess we are back to talking about your new bras. It’s a really special moment for a mother when she buys her daughter her first bra. I want to thank you for allowing me to have that moment.”

  “Mom, I’m not your daughter.”

  Giggling, Sally whispered, “You had everyone in the mall fooled and everyone in this restaurant is certainly fooled. Lee, you got fitted for a bra by a professional today. She did not see my son there. She saw my daughter and she made sure my daughter was wearing a bra when she left. I love you. But today, you are my little girl. And, I am enjoying it.”

  Lee thought about her words carefully. “Mom, I don’t want to be a girl. I want to be a boy. I want to date girls. I want to get married and have babies with my wife.”

  Sally almost had tears in her eyes, “I am so proud of you. In many ways you are the perfect child. While I know the cheerleading and now the competition squad were not in your original plans, your father and I could not be prouder of how you have dealt with things. You like soft underwear. Over half the population likes soft underwear. Maybe sometimes, in secret, you like a little feminine touch. Or you want to wear something that others might think is wrong. I wanted to make sure that my child, who I Iove dearly, had the little things to keep him happy. I will always treasure the memories of today. I hope you will also. You can wear most of the things we bought today and no one will be the wiser. And, if that makes you happy or gives you a secret thrill, I wanted you to know that is alright. If you want anything or if you want to talk to me about anything at all, I want you to know I will always be there for you.”

  Both of them had tears now. As Sally dabbed her face the waitress came by and said, “Aw, a mother-daughter crying moment. I miss those bonding moments with my mother. Honey, you are the spitting image of your mother. You two are so cute. I just want to join in on the tears. But, I have to get back to work.” And with that she walked away.

  Lee cried a little harder.

  Sally looked at him hard. “Lee, Darby, your father and I are all going to be at every baseball game as you demonstrate to everyone at your school that you are all boy. You can wear these clothes anytime you want or just look at them late at night. I am not crazy and I don’t actually think you are a girl. Before that, you need to show these girls how to succeed as a competition team and you have to be a member of the team and have your mind totally focused on that and nothing else. Now, my dear, your father is out this evening. Why don’t we head home and put your new clothes away?”

  Darby thought Lee would be back earlier in the afternoon. She was in the kitchen when she noticed Lee and his mom park and remove things from the car. It looked like Lee’s mom had dragged him around some mall all afternoon. They were laden down with bags. She was pretty sure she saw some Victoria Secret bags. Most of the boys wouldn’t want to be with their moms when they went lingerie shopping. Lee was a really good son.

  The other thing that caught her eye was that Lee had his hair loose. While he wore it that way sometimes in the summer, it was unusual during the school year. As usual, he looked cute. There was something else odd. She just couldn’t tell from her kitchen.

  Lee and his mom took their bags upstairs. Lee’s panty drawer was filling fast with an array of colors and patterns. Lee was trying to segment things by style but it just wasn’t working. He decided to move camisoles and the bras to their own drawer and he moved regular outerwear t-shirts to the closet shelf. They hung up his tops to the side in the closet and folded the jeans and added them to his pile of jeans. Shoes were on the floor of the closet next to his other shoes.

  Lee was looking at his closet trying to decide if it was obvious that there were girls’ clothes in there when there was a knock at the back door and they coul
d hear the door open. “Lee, I saw you were back. Do you want to watch a movie?” Darby yelled. The two of them often just walked in to the other’s house.

  Lee suddenly realized he was wearing a top with ruffled sleeves. “Mom?” He pled.

  “Darby, Lee will be right down.” Sally answered back.

  Sally pulled the top over Lee’s head and grabbed a black t-shirt for the state university. Lee pulled the t-shirt on, thanked his mother and ran downstairs.

  Darby smiled seeing Lee, “You guys were gone longer than you expected. Did you go shopping?”

  Sally came in behind Lee, “Hi Darby. Lee and I hit the mall and I dragged him from store to store. Then we grabbed dinner since his dad is tied up tonight.”

  Darby was looking at Sally, “I saw you had a bag or two from Victoria’s Secret. Did you introduce Lee to the secret world of women’s lingerie? Or did he hang out in the mall?”

  Lee stood up for himself, “I did not hang out in the mall. We went in and took a good look around. Mom found some cute things while we were there.” He stated it as proudly as he could.

  Darby smirked, “Lee, most boys don’t refer to their mother’s underclothing as cute. You might want to rethink the characterization.”

  Back on his heels, “That’s not what I meant. I meant there were a lot of cute things in the store.”

  They were friends who loved to kid each other. But she had Lee now. There was no letting up, “Really, tell me more. I think their panties are cute. What do you think?” She was coming fast and not giving him a lot of time to think.

  “I thought they had a lot of cute panties. Well and other stuff too.”

  “Like what?” Darby pressed.

  “The matching bras and camisoles are cute and there were a lot of different styles.” He tried to explain.

  Sally was enjoying this banter. Lee was so embarrassed, he had no idea he was digging himself in deeper.