A Cheerleader and a Musician Pt 2

After talking to this musician, and him asking me on a date, and requesting I wear my cheerleading uniform, I was in two minds. Happy, I mean, what girl doesn't dream of being asked out by her famous crush? Also scared.

Scared because I knew the hotel management would not be happy for an employee to date a famous guest and bring that kind of attention to the hotel. He would absolutely be recognised. What if some reporter or paparazzi put us in a gossip column, especially with me wearing a dumb cheerleader uniform? I can just imagine walking into work after that. I'd be fired. Plus, I did not want that kind of attention.

Scared too because of the whole cheerleader thing. I thought how stupid I would feel. I was already really unsteady around him. I thought I might do something else insane and had asked if he was absolutely certain he wanted to spend dinner with me.

He said not to worry about being seen, we could have dinner in his room, and if I really didn't want to wear the uniform, that was OK. He didn't want to push me into it and he still wanted to have dinner with me.

I should also mention that I suddenly realized how long I had spent talking to him. Not only had I broken everything, and he had no breakfast, but I was supposed to be helping with the big event. He told me to sit and he called down to room service to say he had dropped the tray and I was so helpful clearing it all up and could I be sent back up with another tray. Things like this were another reason I grew to adore him more. He was such a kind person.

When I returned and knocked, the door opened, but he didn't appear. I called out to him and then a hand waving a white pillowcase waved from the doorway. I told him not to worry, I had a cart this time so I wouldn't be throwing a tray at him. He peeked around the corner, grinned, and waved me in.

He had a very large penthouse room, which had a dining table. I set it, pulled the chair out for him, and gave him my best polished table service. We agreed on 8pm for dinner.

When my shift ended, I went straight to my grandmother's house, where I stored boxes of things that I didn't need and wouldn't fit in my apartment. It took awhile, but I finally located the uniform. It was all there, pom-poms, saddle shoes and all. And it still fit! Yay! I took it all back home and and spruced it up.

Now, I knew that wanting to date a cheerleader meant there was a good chance he'd want to see an actual routine. I thought I better practice something because standing there with all his gorgeousness watching me, I knew I would never be able to come up with anything on the fly. So, I practiced. I thought I didn't look too bad and I was still able to do the jumps; and after some stretching, a split too.

I got all dressed up and covered myself in a buttoned up long coat. I decided I should bring another outfit to change into. I wasn't sure if he'd actually want to sit there with me dressed like that for the entire date, so better be prepared. Also, I was afraid if I spilled something again, I better have a back up.

When I arrived, I took the back staircase up from the garage to avoid being seen. Unfortunately, I terrified myself standing at his door afraid to knock. I kept thinking about everything that could go wrong, and did I look totally stupid? Was everything buttoned? Did I have lipstick on my teeth? I terrified myself. I started fumbling in my purse for a mirror to see if I did indeed have lipstick on my teeth when the door suddenly opened.

"Hey Cheerleader! I thought I heard someone out here. Why didn't you knock?" he said and he gave me a big smile. He couldn't see the uniform yet, but he told me I looked amazing and said he loved my hair. I wore it up at work because it was so long, and it often surprised people who only saw me at work how long it was. I had it in high pigtails tied with ribbons. He reached up and pulled one through his hand.

He asked me to wait right there for "two ticks." He came back handing me a huge bouquet of roses, kissed me on the cheek, held out his arm, and walked me to the table. All I could think was 'Oh my god he kissed me!!' Oh my god he gave me roses!! Oh my god it's him!! If I get through this date, I knew it would be a miracle.

When I took my coat off, he actually did gasp. I remember how impressed he was with me in this outfit. Looks like he really wasn't joking when he said he wanted a date with a cheerleader. It seemed so funny to me because here is this mega famous musician and he's really impressed with... me? I felt like such a nobody. Just a nobody morning maid who happened to be a cheerleader once upon a time in my very ordinary life.

My life might have been ordinary, but it was about to become extraordinary.

Feb 21

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  • I think it's lovely that you happened on a situation where you were infatuated with a known musician, and he was able to live out a fantasy of his cheerleader date. How fun! I think women don't appreciate how boys feel about girls cheerleading. The uniforms accentuate the body and just look flirty and fun. I dated a cheerleader in high school and I always had trouble taking my eyes off her when she was dressed. She knew that the pleated wool uniform had immense power and she wasn't afraid to use it on me either.

    I hope you'll share more of your story.

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