I set my alarm for 6:00 a.m., but my sister was in waking me up fifteen minutes earlier. “I’m going to let you wear my old sweats, from now on they’re yours. You need to get up and get going.” She reminded me of Sarai’s invite to run with her in the morning. The practice after a meet was usually light. Today, doing it when many others wouldn’t be around was preferred.

I saw Mandi and another from the girls’ team set out running, leaving Sarai waiting alone. We did warmups as Sarai suggested; they took longer and were more elaborate than I usually did. “Now smile Caryn and as we run please talk with me. It makes the practice go faster.” We were in danger of catching up to the other girls when Sarai veered off running a different route. Despite a longer incline near the seventh hole, it went fast. Nearing the end of the run she stopped. “That was a very good run the day after a meet and I feel great.”

I joked, “It’s probably the high from running a record pace yesterday.”

She blurted out, “That’s bull, I should be stiff and sore; I think it was from our running together… You ran a good pace yesterday, aren’t you usually sore and stiff today?”

It was true, it usually took a second day to get back up to speed. She said, “Go home, shower, and I’ll see you in school.”

I was dumbfounded, ‘no reminder of what I was to wear or that I was hers for the next two weeks.’ I did go home and showered again and ran through the routine that I did last night. The strapped skirt and blouse looked good except for them being on me.

Once at school, I was called to the office and the principal challenged the way I was dressed, saying that it was a distraction to other students and an embarrassment to the School. I don’t do well to being lambasted as he did, and I refused to go home and change as he demanded. Even if I did so, he had not ruled out more punishment.

This was anticipated by my mother. She had written a note to the school and given her phone number if it was not worked out. I didn’t get to see the note, nor hear all of Principal Collins’s conversation with my mother.

I felt like I was on a short leash doing something I didn’t like. The next days included the expected teasing, but from the third class that day it wasn’t all that bad. Third period Ashley passed me a folded up note and when I asked who I was to pass it to? She said it was for me.

I unfolded the note and put it in a textbook we were studying from. The part that spoke to me was, “You’ve been the subject of such notes, now you’re on our side. Enjoy it !” You’ve shown courage in the hard part. We girls are not only happy Sarai won, but that you did not go whimpering off as most boys would. We’re here for you as well.”

I knew who Ashley was, but she was another well-liked senior. I was impressed that she thought enough to compliment and encourage me. I put it away in my fanny pack as a keepsake.

By the next morning, Two boys seriously ask what I was getting to do. It reduced part of the sarcasm and helped me to relax. “I’m sorry you can’t know how neat this is, but you wouldn’t understand.”

I ventured into Katie’s room to talk to her without my parents listening in. “Katie can I talk to you, and you not laugh or tell mom and dad?”

Katie closed down the programs on her computer and turned to me. “Is this what has caused you to be quiet since we’ve been home? Did something bad happen”

I hadn’t realized I had been, “I guess, but it isn’t bad. Crazy maybe.” Katie and Ashley are friends though not close. “I got a note passed to me like I was one of the girls; it was from Ashley Nolan. And it got me to thinking that maybe I should get into this experience and have some fun with it.” Katie smiles and sits up, “So?”

“I was thinking, maybe I could buy a girl’s running skirt with shorts and maybe even wear it for the cross-country meet this Saturday. What do you think?”

She says, “I think it goes with what’s happening and your bold in-your-face attitude. I would suggest you ask your coach beforehand, so you don’t get suspended from the team… If you’re running with Sarai in the morning; I could give you a ride someplace to find and buy a running skirt and outfit.”

Katie was almost too agreeable and it caused me to wonder. I asked, “I have grandma’s gift money, I wonder if Mom would agree it would be okay to use it for that?”

Katie said, “Grandma’s a free spirit, she might actually agree to it quicker than Mom and Dad.”

I said, “Concerning the Coach, I was thinking of telling him instead of asking. If he doesn’t like the idea, he can override my decision and tell me so.”

I called my friend Brad and shared the idea with him. He laughed his head off, but like my Sis, he said it was me.

I finished a report and set it to print off, and then went to talk with my parents.

“Mom and Dad can I have your attention, I have something I want to share with you.” Dad was watching the news, but he turned off the TV, and Mom put down her book. “Before Saturday’s cross-county meet I was thinking of buying a girl’s running skirt and wearing it for the meet.”

Dad laughs, “That’s my boy, he loses a bet and the next thing you know, he wants to be an all-American girl.” He turns to Mom.

Mom says, “That’s funny, but it’s you. What did Coach Higgins say?”

“I’ll find out tomorrow. …I expect he’ll say I still need to wear the guys’ team shirt if not the shorts as well. Katie’s willing to take me after school to find something. I’m planning on using Grandma’s gift money.”

Mom says, “If you don’t pull this off in good Gary style, it could backfire and make you look… Well, well it wouldn’t be favorable. Plus you and your sister should look for a casual dress and a skirt outfit if this continues.”

Katie had come down behind me, “Caryn also needs more panties and another bra. I’m not giving up any more of my stuff. Or we can get me some clothes and I’ll give up some more of mine to her.”

Mom says, “I think there’s a good chance Coach Higgins is going to throw a bucket of cold water on your idea. We know Principal Collins won’t like it but he’ll probably back down if you get your Coach to agree to it before the principal knows.”

Katie says, “Mom, now we know where Gary gets his mischievous spirit from.”

Mom says, “Maybe, but I’m really for girl empowerment. Whoever got Caryn thinking this way, I’m behind her. It is Sarai isn’t it?”

Katie says, “Guess again Mom, this was Ashley Nolan.”

I did not yet understand how women could continue talking about something they already decided.

The next morning after my running with Sarai; having told Sarai about getting a running skirt for Saturday’s meet. I was soon back home to shower and get ready for today. I began to get nervous and was having second thoughts. I wasn’t even sure about following through on the bet.

Having showered and eaten, I put on the skater dress. It was pretty and looked nice in how it sat on me. But wearing a dress and especially one with the hem above my knees and the way it kissed my legs. Well, things were unsettling.

Today, Katie let me drive the car to school. She was amused as she sat and watched my skirted legs as we rode to school. “You know brother that you have nice-looking legs. One can better see the muscle tone when you’re wearing a skirt as opposed to slacks.”

I laughed as I knew she was trying to get a reaction out of me. Then I thought, ‘I better set my attitude or the guys are going to eat me up with their teasing. We met Ashley as we crossed the school parking lot. She said, “You look tough in that dress. I hope your head is on tight or the other boys will get to you.”

Ashley heard my heels click on the pavement, “That’s better, you sound like a girl with an attitude.” Walking next to me she squeezed my hand then she said, “I’m going this way but if you need me, I’ll be there for you.” With that, she headed off.

Katie and I both saw her boyfriend waiting for her. Katie says, “I hope you got the message; she a friend not a girlfriend.” It was no secret that the quarterback was her boyfriend.

After I got to my locker, I had another problem. Things shifted and fell out of it onto the hall floor. Bending as carefully as I could and with my bare legs pointing toward the lockers, I began picking things up. I sorted what I needed for morning classes and what needed to go back into the locker.

Brad came by and threw away somethings I should have discarded before. He gave me a hand as I stood up. He joked, “You did that fairly well for someone new to being a girl.” Joking some more, he says, “You might want to check your lipstick before you get to class.”

My lipstick was light and looked much like my regular lips. Sarai came from the senior section. Before she talked to me, she asked Brad, “Has he been telling you how she’s been running in practice. She’s staying relaxed and I think it will show in her running time come Saturday.”

Brad said, “Will she remember she’s running as a boy and which gate to go through?” All three of us found it funny, but I barely laughed. “Did she share the idea of getting a running skirt?”

That reminded Sarai and me that I better talk to Coach Luke Higgins. Like I had said, I informed Coach Luke Higgins that I planned to run wearing a running skirt. He looked at me, shook his head, and nodded. “Okay, but you better get the bright blue one like Brenda Leih. And if you wear it, you better not be joking around or showing yourself.”

I said, thanks, and assured him I wouldn’t. It would be tomorrow when I would tell the Principal after I had the skirt. I wasn’t broadcasting what I planned, partly in case I backed out.

It was my first day of feminine studies and I found it informative. Ms. Jacobi asked at the end of the class what I thought of it? I said, “It seems to me that it is mostly a matter of perspective. It gives a way of thinking that I… I don’t think many guys think of it. I can’t say, I would think of it if I wasn’t having this experience.”

Ms. Jacobi said, “You know, you can stay in this class after the homecoming weekend is over?”

“That’s an interesting idea, but will I get credit for a full semester?” She assured me it would be worked out. Since it was a junior/senior class; I wasn’t surprised Sarai soon heard how I did. It wasn’t much, but the big thing to me as I didn’t embarrass myself.

I sat with Brenda and Layla from the cross-country team for lunch. It continued to amuse me how things have changed in just three days. Layla asked me, “What boy do you think would be good to date?”

I was pretty sure she meant me, but I wasn’t going there. I said, “I think Tanner would be a neat guy for you.”

She quickly said, “I meant for you, Caryn; plus Tanner’s no one special.”

I said, “As a guy, I think he’s as attractive as most, he’s a good guy and would treat you well. Myself, I have a date for Homecoming.”

Brenda turned the lunch discussion to what we were going to wear for homecoming. She suggested I needed to talk with Sarai and coordinate our dresses, hair, and makeup.”

I was in the school library when Sarai also came in. “Hi Caryn, I was wondering if we could talk about Homecoming. It’s more complicated with you being a girl.” We didn’t get anything decided more than we needed to get together; maybe after the meet.

Once again, getting into the conversation got more complicated. Brenda shows us what she hoped to get and asks my opinion even about her bra. She saw my expression and says she was just trying to involve me, treating me as a girlfriend.

“Brenda, I dress this way because I lost the bet. I’m not expecting to get into the girl thing. I do appreciate being able to eat with you.”

She says, “Well you’re listening in to our conversation. It gets kind of personal, so it’s like you’re one of us… You’re going to be one of us going to Homecoming. Did you know someone nominated you to be one of the junior princess candidates?”

“WHAT!”

Layla says, “Relax, some of the girls did it as a compliment to how you’re behaving. You run with Sarai, wear some girl clothes, and have become a friend to more of us. Honestly tell me you aren’t happy to be with Sarai?”

I take a deep breath, count to five slowly in my head, and looking at their faces I remember they’re friends not the enemy. “Sorry. Thanks for letting me into your world.”

Getting up with the blue skirt of the dress, I am conscious of being in girl mode. I see a classmate Stuart watching me and the girls. His eyes had been on my legs. I said, “Eat your heart out Stu. And no, you can’t date me.”

I was called to the office and was read the riot act for not telling Principal Collins about my plan to run in a skirt. It wasn’t like I was to be the only one, but I was the only boy. Since I held my cool and that Coach Higgins had already given his approval; I was okay. Collins had tried to scare me enough to change my mind.

I found Katie at the end of school and given the choice of going home to freshen up or to go shopping directly. ‘I hadn’t realized shopping was an event in itself that some girls including my sister would change and freshen up for.’

We went to a sporting goods store where I was less likely to be seen by my classmates. While we were in the car, Katie did have me freshen my makeup and lipstick. She even put a light coating of a smokey eyeshadow above my eyes. I smiled once I looked into the mirror as it did takeaway more of the boy look.

A man tried to help us, but Katie would have none of that. Monica became our saleswoman and she knew the colors for the Madden Raiders and even the running skirt that the girls used. Katie discretely shared who I was, and Monica was amused that the size 10 skirt was too big for me. Once I came out to show Katie; Monica made sure that I could bend and be in all the running and stretching positions I would need.

Monica gave Caryn a first-time customer discount. I also got some running socks and at Katie’s insistence a sport’s bra. Katie even snuck in a pair of girl pajamas from my favorite team. While I needed to buy the running skirt, our parents sent along with Katie money for the rest.

On the way home I got a message from Sarai. “Congratulations on the ‘princess’ nomination. You and your sister are invited to my house for a pasta dinner it’s a pre-meet gathering of the girls.”

The pasta dinner wasn’t until seven so we did make it home to change. I changed to another of Katie’s outfits and she helped me change my hair to a ponytail and encouraged me to wear my sports bra. That we did it all in thirty minutes surprised me.

I didn’t expect the other girls to notice I was wearing a bra, but they were pleased to see that I did. The girls were happy and amused that I planned to wear a running skirt during the meet. Sarai and Layla also remarked that I looked much more relaxed than earlier in the week.

Where the guys traditionally pigged out on spaghetti, while the girls had a variety of plates of pasta and sauces. They ate more than usual, there was conversation as they sat around a large table. Mrs. Duvall complimented me for being part of the conversation.

She did ask me to meet with her and Sarai before I left for home. I waited until Katie indicated it was time to go home. Sarai with her mother took me to her room. “I want to ask if it would be okay if you wore this for me during tomorrow’s meet?” It was a small delicate cross and chain. I turned around and she put it on me. She said, “I asked God to bless you in the race tomorrow.”

Before we left the room, Katie had come in and seen the cross necklace. “You’ve had a good week since Monday. I think that something delicate is fitting.” The others had left the room before Sarai kissed me. “I want you to know, I truly do care about you.” I had to pause and wipe a tear and let my eyes clear before we left.

Saturday I woke bright and early. While our meet wasn’t until 10:00 a.m., we had over an hour’s bus ride to get there. I arrived at the bus wearing my regular traveling sweats. My skirted shorts would not be observed until we were there and getting ready to run.

Several did observe that I was wearing one of Sarai’s necklaces. I was also questioned by Chuck Avery and others if I had been training properly? I simply stated the practices were good and the proof would be in my running. Chuck retorted, “I hope the runners behind you don’t cause you to freeze up again. And above all things don’t run through the wrong finish line...”

To be continued...