How I Became a Cheerleader

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DMaster_14
DMaster_14
1,060 Followers

Mom served me light dinner and sent us all to bed. I stayed up for a while, finishing my homework but was exhausted before eleven and I crashed. The next day I was better when I got to school. My nervousness was gone and I was able to face the day without a panic attack. Candy was waiting for me at my locker when I got there and immediately demanded to know what my aunt said. I pulled the signed form from my bag and showed it to her. Candy snatched it from me with a whoop of delight.

"This is great. Grab you stuff and we can go to the gym now and practice. I want you to be ready for tomorrow after school."

"Tryouts are tomorrow," I exclaimed in terror. "I won't be ready by then." I felt like crying. This was going way too fast for me.

"Don't worry, I will help you. You will kill them." Candy told me leading me to the gym. I was already wearing a short loose skirt and tennis shoes, so we jumped right in with the routines. Candy did each one slowly, showing me what I had to do, then she made me slowly do it with her. I was a quick study and was able to keep from falling flat on my face, but when she speeded up I lost my balance and landed on my butt. My legs were spread and you could see my panties, the white ones with the lace around the leg and waist. I sat there stunned for a second until the wolf whistle snapped me back to where I was. Trent and the rest of the team were on the other side of the gym and were staring at my crotch. My knees snapped together just as I heard a real whistle.

"All right you apes get going or I will run your asses till they fall off." The speaker was the football coach. He was an ape alright, more than six feet tall and from my position twice as broad. He had black hair and blue eyes. The scowl on his face looked like it could sour powered cream and the football team disappeared in a heartbeat. He crossed the gym quickly and extended his hand to help me up.

"Are you alright Miss...?"

"Holcombe, Janie Holcombe, Coach...?"

"Whithers, Jim Whithers. Pleased to meet you Miss Holcombe," he said pulling me to my feet effortlessly. "I hope those Neanderthals that call themselves my team did not upset you."

"No, just a little embarrassed. This is not the way I planned on meeting you or the team, with my skirt up around my waist."

"No trouble, Candy is a good teacher, but she does tend to go a little too quick." He said smiling. He turned and looked at Candy, "you teaching her the routines?"


"Yes Coach, her aunt signed the form so I thought she could get a leg up on the competition." Candy replied cheerfully.

"Good, if what I saw today is any indication she will be after your job next year."

"Janie is already a senior Coach." Candy said as I blushed down to my toes.

"Well, at least we will get one year of you gracing our sidelines." If anything, my blush deepened. "If I can help in any way, just you let me know. Okay Janie."

"Thank you Coach Whithers. I will." I replied letting go of his hand as I realized that I was still holding on to it.

"Actually Coach, could you talk to the guys and tell them to back off a little." Candy said, "Trent has been drooling over Janie since he saw her in the parking lot yesterday. You see she just had a bad breakup and is still a little gun shy."

"No problem." He said confidently. "I will talk to him privately. By the way I know a Karen Holcombe, works as an aerobics instructor at the health club, any relation?"

"Yes, she is my aunt." I replied. "My parents are away for the next two years abroad on a business contract. Aunt Karen said I could stay with her to finish school this year and then go on to college."

"Good to know, my ex took classes from your aunt. She said she was good people. I have seen her at the club. Nice lady does a wonderful class. I would be glad to help out anyone related to Karen."

"Thanks Coach." Candy said, "We really need to get to class."

We left the gym, at the door I looked back and saw him still standing there, he winked at me as I left and I blushed again. By the end of the day word had spread around the school. I swear, whoever thinks nothing can travel faster than light has never been in a high school when new gossip has been released. Before lunch the word came down that I was a look but don't touch type. Trent dialed his charm way back and I found him to be nice enough when he was not hitting on me.

Candy and I spent another two hours in the gym working on the routines, this time with the rest of the squad. Their coach saw me and nodded as I tried to keep up. I took it as encouragement and tried even harder. By the end of practice I was able to stay with the team during the routine. Coach even told me to take the top of the pyramid, being the smallest and lightest. I thought there would be complaints but after we finished the girls said that it was great that I was on top. Jennifer, the girl I might be replacing weighed a lot more than I did and the team had a lot less trouble supporting me. Coach even suggested that I might do some of the flying that the team did. As light as I was, I would get good height when they threw me.

The rest of the girls headed for the locker room, but I grabbed my stuff and headed for the door. I told them I had to get home to start dinner before Aunt Karen got home. They shrugged and headed to the locker room. I was just about to the door when Coach Withers called me over. I headed to his office door, looking over my shoulder, I saw Candy glance at me and shrug. He waved me in told me to take a seat and closed the door.

"I just wanted to tell you that I spoke to Trent and the rest of the guys this morning. I told them that you just lost your parents, but did not go into details and told them not ask you. So if they offer sympathy you know why."

"Thanks Coach." I said smiling slightly.

"How do you like our school?" He asked.

"A lot different than my last school," I said.

"Yes, Crawford is an okay school, but we've got them beat."

I froze at this. How did he know the name of my last school?

"I know who you are Jamie." He said softly. My eyes widened at this and I must have looked like a deer caught in a set of headlights. "I was there last year meeting with the football coach when you were in the pool working out. I was shocked that you were I boy. I thought that anyone so fine and petite would have to be a girl. I mentioned your form to the Coach Stevens and he said that it was too bad you were so small or he would have had you on the team."

I remembered the conversation that I had with Stevens. He had told me the very same thing. I had the form, the drive and the endurance to be a great swimmer, but not the size. The rest of the guys beat me regularly only because of their longer reach. Still he let me work out with them and used me as an example whenever one of the team had a problem. That had only made my life harder, they did not pick on me as much as everyone else, but I could feel their disgust that I was singled out by their coach as an example of what to do.

Before I could do more than start to tear up he said, "It is okay, I am not going to rat you out." It did not help, I started to hyperventilate. Coming around his desk, Coach Withers pushed my neck down until my head was down between my knees. His large hands rubbed my back and spoke soothingly to me, calming me down. After a few minutes, my breathing was back to normal and he let me up.

"I wanted you to know that you have someone here you can talk to." He said sitting down again. "If you want, you can shower in here after practice. I heard what you told the rest of the girls and think that that will work. You just have to get cleaned up and out before the rest of the girls. If they see your car, you are sunk."

"Thanks Coach." I said; still not know what to do.

"When we are in here, call me Jim." He said with a warm smile. "Do you want me to call you Jamie or Janie?"

"Janie, it is the only name I have used for the last three months and it might get confusing."

"Okay Janie, why don't you take a shower and get on home, I will just finish some paperwork."

I nodded meekly and went to the back of his office where the shower was. I quickly stripped and was just about too hop in when I looked over my shoulder and saw Jim staring at me. At first I was embarrassed, but after a second, I dropped my hands and let him have a good look. I could not believe how hot it was making me.

"If I didn't know that you were a boy, I would never believe it." He said.

Leaving the shower running, I walked over to him, as sultry as I could, working my hips like I had seen some of the girls in the halls, when they knew the boys were watching. "Why not," I asked.

"Because you are so sexy, I want to do terrible things to you, even though you are a student."

"What things," I asked coyly, standing right in front of him.

"Things a teacher should not do to a student."

"Like what, suck my tits," I said as I shoved my chest into his face.

"Exactly," he tried to say, but the mouthful of nipple I gave made it come out muffled.

His arms went around my waist and pulled me closer to him as he chewed on my nipple. I had never had anyone touch me sexually and the sensations were unbelievable. I felt a tingle that went from my nipple right down to my toes. I threw back my head and hissed as he shifted to the other nipple. I brought my leg up and rubbed the stiffness in his shorts. My hands were entwined in his hair holding him close to me.

Jim laved and licked my chest while my thigh rubbed his cock. His moans of pleasure rumbled through my chest and made me even hornier. Finally I pulled away and knelt between his spread legs and pulled his shorts down. Jim lifted up from the chair to help me, but then settled back down.

I had never seen an erect penis from this angle. It was majestic. I had never seen anything so wonderful in my life. I gripped it, or tried to; my hand would not go all the way around it. I started to jack him off and heard his moan of pleasure as my small hand stroked him. A glistening drop of pre-cum was leaking from the slit in the head and without thinking, my tongue snaked out and captured it. Jim groaned in approval as my tongue lapped up his juice. The taste was inspiring and I wanted more, I slipped my mouth over the head and started to suck. I could not get more than the head and first inch in my mouth. I was too small and had no experience but I still sucked and licked what I could get at. I reached down and felt his balls. They were large and full of cum. I wanted it all. I sucked harder on his cock, imagining his cum shooting down my throat and my hand started to jerk him off in time with my sucking. I don't know how but I came up with the rhythm naturally. I felt his balls tighten and sucked as hard as I could only to have him pull my off his cock. I looked up at him pleadingly.

"That was the best head job I have ever had." He said panting, "But I want more than that from you."

He picked me up and laid me on my back on his desk. Reaching into his desk he pulled out a tube of some kind of ointment and squeezed a big dollop on the head of his cock. A few strokes and he was fully lubed. Some more ointment on his fingers and she started to massage my butt. I laid back on his desk and let him do what he wanted. By this time I was so horny, he could have driven a truck up my ass and I would have begged for more. I felt his fingers slid inside of me and pushed back against him.

"Eager little one ain't you." He said smiling down at me, adding a third finger up my ass.

"Yes Coach," I panted at him, "please fuck me, fuck me now."

"As you wish," he said, pulling his fingers out of my ass. I felt empty until I felt the head of his cock push against my asshole. I changed my mind, I did not want a truck up there, his cock was too big as it was. He pressed slowly and steadily on my ass and just when I was about to holler uncle, I felt him break through the ring of my ass and slid inside me. I breathed a sigh of relief as I felt him slip into me. It was the most wonderful feeling that I have every felt. Jim stopped for a moment to let me get used to him, but I was too impatient and I pushed down to him.

I felt him push into me until I could feel his pubic hair on me ass. I moaned in delight and he pulled me upright. I wrapped my arms around his neck and he stood up straight, taking me off the desk entirely. I hung around his neck as he stepped back from the desk and started to walk around his office. Every step he took drove him deeper into my ass. I moaned in delight and told him to fuck me harder. Jim pushed me up against the wall and slammed into me. I grunted in delight and wrapped my legs around his waist, pulling him deeper.

"Harder, fuck me harder." I demanded of him.

Jim fucked me against the wall for more than ten minutes, he pounded me deep, and I had never felt anything so wonderful in my life. I felt my body shudder several times in what I can only believe were orgasms, cum was running down my body and onto his legs. I had been a virgin until this point and I was losing my cherry to a man.

Jim finally turned from the wall and sat down in the chair. My legs were draped over the side and he told me to fuck myself on his cock. I planted both feet on the floor and started to ride him. I bounced up and down on the balls of my feet. The feeling of his cock sliding in and out of my channel was delirious. His hands gripped my waist and he pulled me up and down faster. I let him do what he wanted with me and focused on tightening and relaxing my pussy as he fucked me. Finally as I was starting to get sore I felt his cock start to throb even harder and his strokes were getting more frenzied.

"I'm gonna cum." He grunted at me.

"Yes, come in me, fill me up, fill my ass." I screamed as I came again.

"No, it is your pussy, I am gonna fill you pussy." He gasped.

"Yes, fill my pussy with your seed." I begged breathlessly.

Jim growled and I felt his cock spit out a burning liquid up my ass. It scalded me and I loved it. I shuddered and collapsed on his chest, panting for breath. Jim pulled me down tighter to his groin and kept on shooting into me. I felt every twitch and spasm from his cock.

We sat together for several minutes, until we caught our breaths. I could feel his cock still twitching inside me every so often and I tightened my hole around him. I kissed him softly and he returned my kiss and hugged me tight. I felt his cock softening inside me and I pushed it out be reflex, much sooner than I really wanted to.

"Come on, we need a shower, before we ruin the upholstery." Jim said, picking me up and standing up. I wrapped my legs around his waist and buried my face in his neck. Jim deposited me on the toilet and stepped into the still running shower. I relaxed my ass and felt his cum pour out of me. I finished as he got out of the shower and stepped in after him.

The water was hot and relaxing, I had not realized that I was so wound up. The practice, the shock and sex with Coach Withers hand tighter than a drum. I could still feel my asshole gaping open from the wonderful fuck I had just had. I paused, no my pussy was gaping open. I loved the feel of it. I soaked in the spray for a while until Jim poked his head in said it was getting late and we had to go.

I got out and dried off. Jim was dressed in his sweats again and he stood watching me dress with lust in his eyes. I wiggled my ass at him and he growled with lust, but we did not have time to do any more. I quickly found myself walking out of the school with Jim, his car was parked not far from mine and he walked me to mine in the empty lot. As he opened the door for me he said.

"That was the best time I have had in a long time. I would love to do it again."

"Any time Coach," I whispered shyly.

"I will take you up on that, by the way, tomorrow bring the solvent for the glue. I want to see the real you. Be careful walking, you are a little bow legged." And he was gone, leaving me standing there in shock.

I got home and Mom and Susan were already there. They took one look at the way I was walking and started to giggle.

"You look like you had fun." Susan said smiling.

"Hard work out," I mumbled and headed for the stairs.

"With who, the team or someone special," Mom quipped.

During dinner they both saw the way I was having trouble sitting and started laughing again. I threw my napkin at them. Mom then proceeded to have a long talk with me during dinner about a woman's body and the pleasure it could give and receive.

After dinner, she told me to shower again and remove my pussy. I did as she said and she showed me a new one that she had ordered. This one had a channel that went up into my body, so that I could actually fuck someone with my pussy as well as my ass. It also had a drainage hole to allow me to pee with it on. I told her that I would wait until the weekend to try it out. I did not want to have a problem at school with the channel, two days of practice at home sounded like a good idea and Mom agreed. She even showed me that this model had a hymen, replaceable, so that I could lose my virginity more than once if I wished.

The next morning, I was up and dressed and ready to go on time. I felt wonderful. The sex with Jim had really brought a glow to my skin and a new energy to my step. Mom and Susan both noted the change and giggled at me. I just blushed and went on about my day. When I got to school, I saw that there was a notice on the board with the new list of cheerleaders. Shaking with fear I read it slowly and saw my name. I had made the cut. I turned and saw Candy standing back by our lockers and saw the smile on her face. This was going to be a great year. At least that is what I thought then. If I had known what was going to happen that afternoon, I would have gone home right that minute.

DMaster_14
DMaster_14
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24 Comments
ColonelinguistColonelinguist9 months ago

Well! That sure was hot as hell. I imagine I’ll be spending the next several days reading all of your 16 chapters! I had sent your works to my ‘to do’ file a while back. It had looked interesting to me but shit,…and I saw that it had taken you more than six years to complete it DMaster.

Truth is I’ve fantasized about what it might be like to get with a petite t-girl like your Janie, in a similar way I just vicariously experienced with her and ‘The Coach’ only moments ago. I fact, I think I’ll re-examine that part once more before I take a nice, very long…hot shower! I just wonder what it must be like to live inside your head for a day! I see it’s been a minute since you last posted on here. I just hope you’re still at it D; you got serious skills!

AnonymousAnonymousabout 1 year ago

It was going along great until you turned him gay and had him fuck the coach. What a stupid cliche and it ruined the entire story.

louis_adjanilouis_adjanialmost 2 years ago

Great story! Definitely one of my favorites :)

SuzieCrossSuzieCrossalmost 2 years ago

What a great story I enjoyed it very much, and hope to read more adventures in the future.

Rwa4768Rwa4768over 4 years ago
Very good

I enjoyed your story and hope to see more chapters soon.

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