Crystal's StorySite


My Life as a Drillteamer

by Tracy


In the fall of my sophomore year in high school, my girlfriend Laurie & I decided to go out on Halloween as each other. She wore jeans, suede boots, a flannel shirt of mine, and a corduroy blazer that I wore all the time. I wore her drill-team outfit.

Laurie & I had been going out since the summer. It was a bit of an odd match; I was a bit of a freak, and hung out mostly with the stoners, while Laurie was very straight-laced. Her friends were mostly cheerleaders and drill-teamers. I had long hair, almost to my shoulders, and she & I had joked about dressing alike before. At 5'8" I was only about an inch taller than her, and I was slender with thin, androgynous features. She knew how turned on I was by the idea of looking like a girl, and she was determined that for one night I was going to be, or at least look like, a full-fledged drill-teamer.

The drill-team marched with pompoms at halftime of football and basketball games. There were about 40 girls on the squad, and they dressed in long-sleeved unitards with short, fringed skirts, white socks, and Keds. Our school teams were the Warriors, and the drill team was known as the "Cheerokees," so to complete the Indian look they wore headbands and feathers. On game days, at school, the Cheerokees wore orange circle skirts with button-down shirts, along with their headbands and the usual white sneakers and white socks. Since I couldn't fit into Laurie's marching outfit, she said I could wear her circle skirt. We were going to a Halloween party at my friend Robert's house, and she told me to come over a couple of hours early to her house so we'd have plenty of time to get ready.

When I got to Laurie's house that night she said to come back to her room. This was normally off-limits, but her parents were out of town and I was sleeping over that night. When I got back to her room I saw that she'd laid out my outfit for the night: her skirt, which she'd expanded with some elastic sewn in at the back, where it buttoned; a pair of orange panties; a white button-down shirt and a brand-new pair of Keds, both in my size. She'd also made a headband for me that matched the ones the Cherokees wore. There was even a bra in my size, with a couple of foam "falsies."

She had me strip, and I started putting on the skirt and the matching panties. "Not so fast," she said. She handed me a new pair of pantyhose and said "You've got to wear these too." She helped me pull up the hose without tearing them, and showed me how to fasten the bra, then slipped in the foam padding. Once I had my lingerie on, she sat me down in front of her dressing table and proceeded to put my hair up in medium-sized hot rollers. I'd never had my hair set before. It was odd to feel the hot, heavy rollers being pinned up in my hair. When she finished setting my hair she let me have a look in the mirror. I couldn't believe how different I looked already. Then she made me up: first foundation to hide my beard shadow, then mascara, then eye-shadow, then blush, then lipstick and eye-liner. It took a long time. I appreciated how much time Laurie spent to look beautiful every day. The pantyhose felt tight around my groin, and I could feel the lace of the bra against my chest. By this time I had a huge hard-on, but she pushed me away, saying "Later."

Then I put on her skirt and the white shirt. You could see the straps of the bra clearly under the shirt. After about 15 minutes she took my hair down. I loved the way the soft warm curls fell around my face as she removed the rollers. She had me turn my head upside down, and fluffed out my curls. Then she put my headband on, using the tail of a comb to layer my hair over it so just the front of it showed, on my forehead. Finally, she slipped a feather upright in the back, and put a single bobby pin in the side to hold my hair back. She stepped back, had me stand up, and said "Twirl."

"What?" I said, laughing.

"You heard me. Twirl, come on."

I twirled around on one sneaker toe. The circle skirt flared out around me and then re-settled. My curls bounced against my cheeks and neck. I was out of breath, excited and nervous at the same time.

"You look so cute," said Laurie. She pushed me in front of the full-length mirror on her bathroom door. Standing there was a rather tall girl in a spotless drillteam outfit, with her hair in big bouncy curls. I'm not sure I would have recognized myself. I mumbled: "Jesus. I can't go out like this."

"Oh yes you can," she laughed. She handed me my own letter jacket, which she always wore when she was in her Cheerokee outfit, and put on my old corduroy jacket. I have to say that with her tousled blond hair falling over her eyes, my big flannel shirt tucked into jeans, and her suede boots, she looked mighty sexy herself. She had on just a little bit of makeup – Laurie never left the house without makeup.

We were the hit of the party. There were probably 100 people there, including most of the cheerleaders and many of the Cheerokees. They flocked around us as soon as we arrived, complimenting both of us and exclaiming how cute I looked, what nice legs I had, how great my curls were, and so on. After a few minutes Carol, one of Laurie's best friends who was one of the co-captains of the Cheerokees, exclaimed: "You should try out, Brian!"

That was how it started. Every one of the girls agreed: I'd make a great Cheerokee, why didn't I try out? In fact, someone said, there'd been guys on the squad before: two years ago two guys had tried out and made it. With the girls egging me on, I said "Sure, why not?"

We got pretty drunk at the party and then went home to Laurie's. I started to take off my sneakers and skirt but she stopped me: "Wait! Can you leave them on for a while, please?"

So we lay down on her bed, on top of the covers. She took the bobby pin out of my hair, took out my feather and slipped my headband back so it held my hair away from my face. I don't think I'd ever been so excited in my life.

"You enjoyed it, didn't you?" she asked.

"What, the party?"

"You know what I mean. Being a Cheerokee, and having everyone tell you how cute you look."

"Well, yeah, I guess I did." I leaned over to kiss her, but she pushed me away.

"Hold on a minute. I want to ask you something." She was suddenly kind of serious. I leaned back and waited. "Would you really try out?"

I'd been wondering the same thing all evening. "I dunno," I said. "Maybe. What would you think?"

She had her eyes down, half-closed. She looked up at me and I thought she'd never looked so beautiful. "I'd love it," she said, softly.

"Really? Why?"

"Just think about all the time we'd get to spend together. I think you make a really pretty Cheerokee. And I know it would make you happy. You should do whatever makes you happy."

I considered that for a while. "Wouldn't you be embarrassed?"

"Who is there to be embarrassed in front of?" she said quickly. I realized that she'd been thinking about this, too. "My friends would love it. And your friends don't like me anyway."

"Sure they do."

"No they don't. They think I'm a priss and a goody-two-shoes."

"Well, I guess if I tried out I'd be a priss too."

"That's right," she said laughing. She sat up, pushed me over, and straddled me, holding my hands down on the bed. "It's really hard work, you know. You'd have to be serious about it. And you'd have to get used to wearing the outfits, and doing your hair, and everything."

"Do you really think they'd let a guy on the squad?"

"Sure. I don't think they can stop you, if you make it. We've got guy cheerleaders, for god's sake. I'll check with Mrs. Mahan." Mrs. Mahan was the faculty sponsor. "Anyway, Carol is the co-captain and I know she wants you to try out."

I couldn't believe it. She was quite serious. I lay there wondering if I really had the guts. I didn't think so. But I wanted to please Laurie. And I really liked wearing the Cheerokee outfit. "Let me think about it."

"Okay, but don't think too long. You've got to join the Pep Squad if you're going to try out." I hadn't thought about this: the Pep Squad was made up of freshmen and sophomores, mostly girls, but a few boys usually joined. They wore shorts and sweaters, and sat in the stands and cheered along with the cheerleaders. Only members of the Pep Squad could try out for cheerleader or Cheerokees. The few guys who joined the Pep Squad were usually going on to try out to be cheerleaders. They were considered queer, and squirrely, but they got a lot of support from the girls on the squad. Was I really going to be one of them? I knew I'd have to make a decision soon.

"You're going to make such a great Cheerokee," Laurie said, as she rolled over on top of me and reached under my skirt. I could feel her pulling my panties off and tugging the hem of my pantyhose down. That night, for the first time, I made love in my drillteam outfit. It would not be the last.


The next Monday, I must have had a dozen girls – all cheerleaders or Cheerokees -- come up to me at school and say "You looked so cute on Saturday night. Are you really going to try out?" The same number of guys looked at me like I'd grown breasts, which I had for one night. Laurie kept bugging me to sign up for the Pep Squad. I had to join before the homecoming game, which was two weeks away. After that they closed the squad for the year. Mrs. Mahan kept the sign-up sheet in her room. Finally, Laurie talked me into it. "Just try it, okay?" she implored. "If you really hate it you can always quit."

The next day, at the end of 6th period, she came with me to Mrs. Mahan's room. Mrs. Mahan was a young history teacher, very popular, whose classes always had a high percentage of cheerleaders and Cheerokees in them. She smiled at me when I came in.

"I hear you make a very lovely Cheerokee, Brian," she said slyly.

I didn't say anything at first. Laurie elbowed me in the ribs. "Uh -- I…I'd like to sign up for the Pep Squad, please." My mouth was so dry I had trouble talking.

"Great," she said. "We need more boys. Here you go." She pulled the sign-up sheet out of her drawer. "Next meeting's tomorrow. Can you get an outfit by Friday?"

"Yes ma'am," said Laurie firmly. "He'll have it."

"Okay, then. Anything else?"

Suddenly I had a blast of courage. "Well, yes."

There was a silence. Eyebrows raised, Mrs. Mahan waited.

"We want to know what the rules are about guys trying out for the Cheerokees," Laurie blurted out. I felt like I'd just leaped off a cliff.

The teacher smiled. "Well, you know we had two boys on the squad two years ago. Brave fellows. They wore these kind of hotpants and performed separate routines from the girls."

"Yes ma'am."

"Nobody really liked that arrangement. But we can't forbid boys from trying out, or being on the squad, if they make it. The rules say anyone on the Pep Squad can try out – it doesn't specify girls. So we just added a rule that everyone who makes it wears the same outfits, does the same routines, everything. That means circle skirts, headbands, hair ribbons -- the works. I doubt any boys will be brave enough to try out, now. But they're certainly welcome. Does that answer your question?"

"Y-yes ma'am," I stammered. We turned to go.

"And Brian?" Mrs. Mahan said. I turned around. "Good luck on the Pep Squad."


The next two days were a blur. I had to go to the Pep Squad meeting, get my Mom's signature on the approval form for the Squad {my parents, thank God, were divorced, and I saw my Dad every other weekend}, and get my outfit together. The shorts were more like a pair of orange culottes. The sweater was just a white V-neck with an orange W, for West High, sewed on. My mother sewed on the letter Thursday night. She was amused by my sudden burst of school spirit, but she didn't say too much. She asked me how I was going to wear my hair on Friday. I hadn't really thought about it; usually I just pulled it back in a ponytail. That night Laurie called to see I was ready. There was an early pep assembly on Friday and I knew she was busy getting ready. "So, come by here early and I'll do your hair, okay?"

"Umm, what do you mean?"

"I'm going to roll it, silly."

I gulped. This was getting out of hand quickly. The next morning I woke up early and put on my Pep Squad outfit. I felt very girlish, but at least I knew that there would be other guys dressed the same way at school. I pulled on my Nike tennis shoes and ran out the door before I could chicken out. When I got to Laurie's house her mother greeted me at the door. "Well, don't you look cute!" she said. "You can go on back." Laurie was just taking the rollers out of her hair. She pointed to my feet and said "Gotta change those." I'd forgotten about my new girls' Keds, from Halloween. They were waiting by Laurie's bed. Reluctantly, I changed into them. Then, once the rollers were hot again, she said "Have a seat."

"Look, Laurie –" I began.

"Don't worry. I'm not going to curl it like I did last time. But you're a spirit-club member now; you've got to look nice." So I let her put my hair up in jumbo rollers. While we waited, with me in rollers, Laurie finished doing her hair and put on her headband, layering it under her hair. She looked great. I couldn't believe we were both going to school in our spirit outfits: her in her circle skirt and me in my Pep Squad uniform. She took my hair down and brushed it out, curling it under at the ends and putting it behind my ears. I had to admit it looked very cute. I was a little jealous that Laurie got to wear the Cheerokee headband & I didn't.

That day at school was not as bad as I'd imagined. Some of my guy friends gave me a lot of grief, and whistled at me and stuff, but the girls – who hadn't known I'd joined the Pep Squad – were excited, coming up to congratulate me and tell me how nice I looked. I started to feel like I was a member of a group – one I'd wanted to belong to for a long time, without knowing it. That afternoon Laurie & I were hanging out at lunch. The weather had gotten hot and she'd put her hair up in a high ponytail. "Aren't you hot?" she asked. In my sweater, as a matter of fact, I was. "Here," she said, rummaging in her purse. She pulled out a barrette. "Turn around."

In a flash she'd pinned my hair up against the back of my head. I started to take it out, but for some reason I stopped. After all, I was already wearing a Pep Squad uniform. What difference did it make? And, oddly, I was right: no one said anything about my new hair-do the rest of school.

The game was loads of fun. All the Pep Squad members rode to the stadium on the bus with the cheerleaders and Cheerokees, so Laurie & I got to sit together. I'd been in my outfit all day and was beginning to feel comfortable in it. We sang songs and did cheers all the way to the stadium. After school Laurie had taken the barrette out of my hair and given it a quick touch-up with the hot rollers, so it was big and freshly curled under at the ends. Like all the Cheerokees, Laurie had her pompoms with her and had changed into her marching outfit. We had matching Keds on and our hair looked almost identical, except Laurie had on the coveted headband and feather that only cheerleaders and Cheerokees got to wear. Before we got off the bus I gave her a big kiss and said "Good luck!"

Sitting in the stands with the Pep Squad was a completely new experience, like I'd never been to a football game before. The Cheerokees sat in a group next to us. I could see Laurie, and for the first time I felt envious. Like many of the girls around me, I had a real desire to be on the drill team, We were supposed to do all the hand motions along with each cheer the cheerleaders did, and when the Warriors scored, of course, we went bananas. When the Cheerokees got up to go down to the field for their halftime performance, Laurie waved at me and I held up both hands with my fingers crossed. They performed beautifully, of course. The climax of each performance was a can-can line where they all linked arms and did high kicks. The pompom moves were very complex, and I found myself following along, wondering if I could ever learn those moves. Was drill-team really just a girl thing?

After the Cheerokees came off the field we were allowed to leave our seats for part of the third quarter. Laurie came bouncing up, carrying her pompoms, out of breath, her cheeks flushed. "Did you see that?!" she cried. "I almost fell on my butt in the first crossover!"

I hugged her and assured her she did fine. We were excited and talking in high voices, and I found myself slipping into the high-pitched, singsong speech the cheerleaders & Cheerokees used. I was as excited as Laurie. We bought cokes and took them to a secluded, grassy area alongside the stands. She laid her pompoms down and soon we fell into a hot embrace. My hands moved all over her uniform, sliding up her skirt and fondling her breasts. She kissed me more fiercely than usual, her tongue probing my mouth. In minutes we were almost having sex. "Whoa," Laurie said, pushing me back. "This is like 5 demerits if we get caught making out in uniform." Twenty demerits, I knew, and you were off the team. Just being late back to our places in the stands was two demerits. I helped her straighten her headband and feather, and she brushed off my sweater and shorts. Holding hands, we went back to our places.

After the game we went to the pizza parlor where the cheerleaders, drill-teamers and football players traditionally gathered. We were all still in uniform. It felt strange to be there with a gaggle of girls, many of whom had boyfriends on the football team, waiting for the athletes to arrive. Suddenly I felt humiliated -- I'd played football myself up until 9th grade, after all, now here I was sitting in a Pep Squad outfit with a bunch of girls. Sensing I was uncomfortable, Laurie put her hand on my knee. "You okay?"


"Come on."

She took me out back, to the restaurant's patio. It was just the two of us. We sat for a while in silence, just holding hands. I felt like tearing off the letter sweater and ripping off my girls' sneakers. Laurie watched my face intently. "Kinda strange, huh?" she said finally.

"Why do you want me to do this?" I said. I was almost crying. "Why do you want to be with me? Maybe you'd be happier being with a girl."

"I want you to be happy," she insisted. Then she put her head on one hand. "But you're right. I do like being with you when you're dressed like a girl. It makes you softer."

"Not everywhere," I said, smiling.

"I'll say!" she laughed, touching my crotch. "I guess I do like having a girlfriend."

"A girlfriend with a penis," I said. We were almost kissing.

"Exactly," she said. She gave me a warm kiss, then stared into my eyes. "Look," she said. "Let's just go slow. We're not making any big commitments here. You just take it day by day. If you want to quit, I'll understand."

"Okay," I said, taking a deep breath.

She licked my ear and spoke into it. "But you still have to dress up for me," she whispered.


I didn't quit, after all. After that first game I got caught up in being on the Pep Squad – going to meetings, painting banners, cheering at the games, riding on the Cheerokee bus, hanging out with the girls. In the following weeks people got kind of tired of ridiculing me and gradually gave it up – some of my former guy "friends" just stopped talking to me, but they were outnumbered by the new friends I had on the squad. It was like I'd passed through a humiliation plateau; once I decided 'Screw it, I'm going to do what I enjoy,' I quit caring what a lot of other people thought and I found a lot of support from people who really cared about me. By the time the new year had started I'd started to feel comfortable in my Pep Squad outfit. I still didn't know if I was really going to try out. Especially close were Laurie's best friends, Carol and Ashley, who was a cheerleader. The four of us would hang out together on Friday afternoons, before games, and carpool to school together. They let me know they didn't care if I dressed like a girl; they thought it took a lot of self-confidence to be on the Pep Squad and they admired me and treated me like I was one of them.

I remember one Saturday that spring, we were all hanging out together at Laurie's house. Her parents had a pool and we often spent Saturdays over there, lounging and swimming and reading magazines. There was a big party that night and the girls were talking about what they were going to wear. I had on one of Laurie's Cheerokee t-shirts, a speedo swimsuit, and Keds with no socks. Carol arrived with her hair up in Velcro rollers – in a ponytail on top of her head, actually, and the ponytail sectioned off into 4 curlers. Laurie went inside and brought out her Velcro rollers and pretty soon both she and Ashley had their hair up in them also. Then Laurie brought the roller bag over to where I was lying on a lounge chair. "Sit up," she ordered.

When I did, she started sectioning off my hair. The next thing I knew she had a roller and was winding it into my hair.

"Hey!" I said. No one had seen me in rollers before besides Laurie and her mom. "What are you doing?"

"Oh don't be such a baby," Laurie said. "I'm just putting a few rollers in your hair."

"You know you love it, Brian," teased Carol.

"Oh c'mon," added Ashley. "We're all in curlers, it won't kill you."

Laurie finished winding the Velcro roller {they were the large-sized red ones} and slipped in a clip. In a few minutes she'd put all my hair up, just like hers. So the four of us spent the rest of that afternoon in curlers, by the pool. At one point Laurie quietly lured me into the bathhouse, where we had a quickie & then slipped out, trying not to giggle. It was pretty obvious what was going on. Then Carol spoke up.

"So Brian, are you going to try out, or not?"

There was silence. Laurie & I hadn't really talked about it since that night after the football game, and though I'd joined the Pep Squad so I could try out, I'd purposely put off deciding.

"Clinic starts in 3 weeks," said Ashley, flipping the pages of her magazine. Clinic was the two-week pre-tryout period where everyone trying out for cheerleader and Cheerokees had to practice together and learn the routines for tryouts. "You need to sign up if you're trying out."

"We could start practicing here….?" Laurie said. I could tell she was worried about pressuring me.

Suddenly the idea of practicing with these girls – my best friends – seemed too good to pass up. As Laurie had said, I could always drop out later. "Sure," I said. "When do we start?"

We started that day, in our t-shirts and swimsuits and sneakers, with our hair up in rollers. Laurie ran inside to grab her pompoms. While Ashley, the cheerleader, watched, calling out encouragement, Laurie and Carol started going over the basic steps with me and showing me some simple pompom moves. Learning to march was like learning to walk all over again: They made me bounce on my toes and swing my hips, keeping my arm motions big and obvious. Above all, they said, you have to smile. We worked for almost an hour. It was surprisingly tiring. But by the end of the day I could march almost like a Cheerokee and I'd started to understand how to handle the pompoms.

Carol and Ashley left to go home, and Laurie & I went inside to change for the party. Since her parents, as they often did on Saturdays, had gone out of town, I made margaritas for us. I'd brought some clothes to wear to the party – just a button-down and a pair of jeans. My hair had been up in rollers for more than four hours. Laurie was eyeing me with a strange smile. "I know that look," I said. "What are you up to?"

"I've got a present for you." From her closet she pulled out a shoebox. Inside were a new pair of Dr. Scholl's sandals, in my size, with blue straps. Laurie had two pair herself, and she knew I'd been wanting to try them for a long time. I slipped them on. They looked great with my jeans.

"Thank you," I said. "They're swell."

"I want to try something a little different tonight," Laurie said, with a sly wink. While I dressed, being careful not to mess up my curlers, she took her hair down and put on her makeup. She left the makeup out on her dressing table and sat me down. Slowly, she made me up; not as completely as she had at Halloween, but just with subtle mascara, a bit of eyeshadow, and lipstick. It was not easy to tell I had on makeup at all. Then she took the rollers out of my hair. It fell in soft waves to my shoulders. She pulled out one of her suede headbands – not her Cheerokee headband, but the kind that sits on top of your head and holds your hair back – and slipped it on my head. Normally I would have protested – this wasn't Halloween, and I didn't think I was prepared to start wearing girls' hair accessories – but something about the way she looked at me held me up. I turned and looked in the mirror. I wouldn't say music swelled in the background or anything, but I looked quite striking: a guy, clearly, but a very pretty, androgynous guy with long, dark eyelashes, red lips, and a blue suede headband in his hair.

"Like it?" Laurie asked, as if asking about a painting she'd just finished.

"I don't know what to say," I said, honestly. We finished our drinks and headed out to the party. I don't remember much of anything about that party; a few guys laughed at me, I guess, and the girls complimented me, asking if I'd curled my hair, and if I was wearing makeup. I do remember that Laurie & I had a great time and that at midnight we were lying in her bed, naked, just after making love.

She rolled over and put her head on one hand, looking down at me. "I was so proud of you tonight," she said.

"How come?"

"Because you didn't care what other people thought. You wore what you wanted to, and did your hair the way you wanted – "

"You wanted," I interrupted with a laugh.

"—and you looked great, and you didn't worry about anybody else's opinion. That takes a lot of self-confidence."

"It's funny: I wouldn't have done any of this – joined the Pep Squad, curled my hair, worn makeup – without you. But I feel like I'm really just doing stuff that…like I'm becoming more…"


"Exactly. It's like every time I do something new – like today, when you rolled my hair with Carol and Ashley there – I think no, I can't do that, it's too queer. Then I just sort of dive in, and do it, and it seems natural, almost."

"I know. I was looking at you tonight, with your headband and makeup on, and you didn't look strange or funny at all. It was just you, and I was so in love with you."

We were quiet for a while. The moonlight fell in pools on the white bed linens. Laurie was stroking my hair, which was still wavy from the rollers.

"So, are you going to do it?"

"Try out?"


"I don't know. Probably. At least I'll go to clinic, I guess."

"That's right. If you don't like it, you don't have to try out."


"We've got a lot of work to do to get ready."




"I love you."




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