tagGroup SexThe Cheerleading Squad

The Cheerleading Squad


Moving to a new town is never easy, especially when you're 18. My name is Jason, and a quarter of the way into my senior year, and my dad gets a new job a thousand miles away. I hollered, whined, and complained as much as I could, but to no avail. My mom insisted that I stop making a fuss. She said this would be hard on all of us and that dad had no choice. If he didn't take this job we would lose the house since we there was no way we could pay for it for all we invested into it. She said that seeing us upset would just make it harder for him than it already was. I listened to reason and supported my dad as much as possible. He would be making more money at this new job, and moving to the east coast could be fun. I wasn't having much luck out here anyway. I had only a few friends and I never had a girlfriend. I spoke to a girl I was interested in once, but it never went further than that.

The first day at my new school, I was in the main office reading my new schedule. I hadn't looked into after school sports yet so I asked the counselor.

"Are there any spots on the football team? I played last year and I would like to try again," I said.

"Well Jason, the regular season is about to end and there were a lot of applicants this year, but I'll see what I can do. If the team wins this week, they will go out of state for the all star games. By then there are a lot of player changes. If there are no more spots for players, I'll try to get you a spot aiding the team some way," the counselor said.

"Fine," I said and left. Great, instead of being a football stud, I was probably going to be a water filler or a ticket collector. I started my classes the same day. I spoke to a few guys and they seemed pretty cool, but I still felt like an outsider. I spent most of the week by myself, trying to fit in but never actually doing so. I observed the football team on game day, and sure enough they won by a landslide. They were going two states down for the playoff games between the top schools on the east coast. I met a couple guys on the team and they were really excited. I asked them if there was any chance of a spot opening up on the team.

"No way," one jock said. "We're a pretty tight group, so we don't break away easily. Don't worry though, we always need people to come with us on our road games. Thanks for coming to the game." We shook hands and he left. The following school day the counselor informed me of an opening.

"We have an opening," she said. "It's for a water cooler filler-"

"Great," I interrupted. "So I'll be with the team the whole way, right?"

"Let me finish Jason. It's not with the football team. It's with the cheerleader squad."

"What?" I almost screamed.

"On road games they don't have these done automatically. They need someone there to do it so I picked you. You just moved here so I wanted to give you this opportunity to help the football team. The only thing about it is that you won't travel with the team or be there for their practice. You'll leave when everyone else does."

I thought hard about it but ultimately accepted. It was the closest I would get to being with the team. I was kind of afraid about being associated with the cheerleading squad. Not a good group for a man to be in. I saw them during the last regular game. What a peppy squad though. Really cute girls too. I was really attracted to the one on the end, a hot brunette named Holly. This could be my chance to get to know her, I thought. But girls really went after the players, not the water filler.

Two days later the team left on a bus for their next game. They got a whole week off from school to play this game. If they won, they would get another week off for their next game. The school informed me that my bus would leave Friday morning and arrive that night. I would have the weekend off at a hotel until the game on Monday morning.

I got up really early Friday morning to pack up and prepare for the trip. I turned on the shower and got undressed. I noticed my mother's cosmetics on the counter. One bottle was labeled Hair Removal Cream. I observed the patch of pubic hair surrounding my cock, and thought about it. Just for simple curiosity, I rubbed it over my genitals. I let it sit there about ten minutes like the bottle said so, then I washed it off. The hair just fell right out. I rubbed it all off and washed up. I got out of the shower and observed myself in the mirror. I looked almost like a different person. It made me look so much younger, almost prepubescent. Except for the length, which was much more defined with no hair. I got dressed and felt a noticeable difference. I felt cleaner, almost refreshed. Feeling better about my decision, I packed up and my dad dropped me off at the school.

"Call us when you get there," he said as I got out the car.

"I will dad," I yelled back and headed to the side of the building. The bus was already there, the driver outside of it. Some of the cheerleaders were to the side of it talking to each other. I walked to the driver.

"Hope I'm not too early," I said.

"No, everyone else should be here soon. We'll leave as soon as they do," she said.

One of the cheerleaders came up to me. "Hi, I'm Carmen. Thanks for doing this for us," she said. She was real pretty, with sexy blue eyes and long dark hair. I couldn't see much else since she was bundled up in her team jacket.

"You're welcome. I'm Jason. When is everyone else getting here?" I asked.

"Soon. Come over and meet the other girls." We walked to the others and I introduced myself. They were all really nice and made me feel less shy about the situation. We all talked a little and I felt really comfortable. Soon the rest of the girls arrived and the 20 cheerleader team was complete.

"Okay girls, let's get going," Carmen said. They all piled onto the bus.

"Wait," I said. I grabbed the arm of one of them, her name Stephanie. "What about the rest?" I asked.

"This is it," she said.

"I mean the rest of the support group for the cheerleaders," I said.

"You're the only one. Did you think we needed more than one person? Come on, let's go," she said. She grabbed my hand and lead me onto the bus. Just me and the entire cheerleading squad. Wow, I thought. The bus was luxury almost. The driver was separated by a divider, so she wouldn't know what was happening behind her. There were seats towards the front, a small dining area in the middle and a few cots set up towards the rear for anyone who wanted to sleep. There was even a bathroom here! We took off towards our destination, almost 18 hours away. I stowed my suitcase above the seats and sat down as the girls put away their stuff. I was feeling awkward again, but they took care of that. Emily, a beautiful brunette, sat right next to me with a book in her hand.

"So Jason, how did you get this gig?" she asked.

"I tried to get on the football team, but I was too late for that, so they gave me this instead," I said.

Megan was loading the food into the refrigerator. She called out to me.

"Hey Jason, you want something to drink?"

"Sure, a soda would be fine," I told her. She opened a can and brought it to me. She leaned over the chair in front of us. I took the can.

"Tell me, how was your old town?" she asked while leaning forward towards me and Emily.

"A really small town, but everyone was close. I probably knew everyone in the neighborhood," I said.

"I bet it's kind of hard to leave a place like that at 18," Megan said.

"Yeah," I replied, "But I'm getting used to it. I figure if I try to get out as much as I can, it'll help. That's why I tried to get on the team."

Holly walked by and kneeled beside me. "Trust me," she said, "We don't want you to be some water filler here. As far as I'm concerned, you're part of the team. I'd like you to judge our cheers if possible, and I would like your input for new moves too." She patted me on the back and walked by. Emily actually snuggled next to me.

"Do you want to read this book with?" she asked.

"Sure," I replied. I wasn't going to be doing anything else for a while. She leaned forward and unzipped her jacket and took it off. She was wearing a white tank top that showed off her assets nicely. She leaned back against me and started reading.

About five hours later we pulled into a small restaurant for lunch. We all ordered as much as we could since the school was paying for the meals. During the meal, we all laughed and joked with each other. It was a great time and I truly enjoyed the time I was having. These girls were really great and did everything they could to help me fit in. After I finished I got up and went to the bathroom. When I came out of the restroom I saw Holly outside next to the bus. She looked really cute in her tank top and cutoff shorts. I walked outside and joined her.

"Hey, why are you out her alone?" I asked.

"Oh I just finished first so I came out for some air," she said. "Are you having fun on this trip?" she asked.

"Definitely. I thought it would be weird being part of the cheerleading team, but I'm loving it so far. Thank you for being so nice to me." I said that last part with a smile.

"You're welcome," she replied with her own sweet smile. We stood there for a moment and were about to draw closer until everyone else came outside. We all loaded into the bus and took off. A couple hours down the road Sally and me were watching the lake out the window as the bus rolled along the bridge. She pointed to a small boat with a couple of fisherman.

"I used to go fishing all the time as a little girl," she said. "My Dad would take me to this lake when I was little and we would compete to see who could get the biggest catch. We still go at least once a year. He really loves going with me. I love it too."

"So who usually wins?" I asked, really interested in what she had to say.

"Me, of course, though I let him have his days," she said laughing. I told her about my dad hosting his company barbecue and including my old football team in the event. We were soon lost in conversation about family and friends. While talking, I noticed just how pretty she was. Long blonde hair and a shape to die for. It was all topped off by her beautiful green eyes and her sexy smile. In fact, all the girls by now had removed their jackets and were wearing clothes kind enough to let me view their sexy bodies. My God they were hot and I felt really close to them also. I was certainly glad I did this trip.

Many hours later we finally reached our destination. We were in a different hotel then the players. The whole sex issue obviously. Apparently we were many miles from their hotel. The girls were divided up, two to a room. I was given my own all the way on the other side of the hotel. It was a large building, which was kind of strange considering it was a small town. There were only a couple of cars in the lot too. I bet we were the only ones here. It was almost midnight when we arrived so I went straight to my room, utterly exhausted. We didn't sleep at all on the bus because we all had so much fun. I dropped my suitcase on the floor and quickly undressed. I crashed on the bed and was asleep almost instantly.

I woke up the next morning in the same position as when I fell asleep. What time is it, I thought. I looked around and finally found the clock. Only 7 AM. I was still sleepy, but I was hungry even more. I got up and opened my suitcase. I packed only three different sets of clothes for this trip. A few casual shirts and three jeans. With it being the end of September I knew I needed to dress warm as the fall would bring some pretty chilly weather. I got dressed and slid on my shoes. I walked outside and instantly regretted my clothing choice. It was blazing hot outside! The sun was as bright as it could be and sweat was already forming on my forehead. I saw a thermostat beside the window and saw it was over 100 degrees. I didn't know east coast weather could be so different. Too bad I didn't bring any shorts, I thought. I walked downstairs and around the corner towards the lobby. I heard laughing and voices that sounded like the cheerleaders somewhere nearby. It was from the pool. It was surrounded by a high gate at the end of the hotel. I walked towards the entrance and walked through the gate.

I stood there stunned. All twenty cheerleaders were in or around the pool wearing colorful, revealing bikinis. Some were swimming around, while others were sunbathing on lounge chairs or sitting at the tables under the umbrellas.

"Hey Jason, I didn't think you would be up this early," said Ashley, the pretty redhead on the lounge chair.

"Oh, I was getting something to eat and I heard you girls out here," I explained. God, they were so hot, I thought. I tried hard not to stare, because I respected them so much, but they made it so hard. Holly was in the pool when she called me.

"You must be burning up Jason. Why don't you join us?" she said while treading water from the middle of the pool.

"I would, but I didn't bring a swimsuit," I told her. She looked disappointed.

"Well, that shouldn't have to stop you. Why don't you get undressed and jump in?" she offered.

"I r-really don't think that's a good idea," I stammered while backing away. I so wanted to join her. She was almost beckoning me. I didn't truly realize how attractive she was until now. Her nice tan skin, full double D breast, and the long dark hair made one incredibly hot package. Her blue eyes seemed to draw me towards her. She beckoned some more.

"Come on Jason. We're all adults here. None of you girls mind, do you?" she asked the rest.

"No, not at all," Nicole said.

"Go ahead, we don't mind Jason," said Stephanie.

I decided to go for it. This would be my one chance with them. Hopefully this wasn't some dirty prank and they wouldn't run off with my clothes or something. I took my shirt off while the rest seemed to go back to what they were doing, but I'm pretty sure they were watching me from the corner of their eyes. Holly was sure watching me, no doubt. I kicked off my shoes, unzipped my pants and slid them off. Now was the moment. Thoroughly glad I did not have an erection, I dropped my boxers. My penis dangled between my legs and there was a moment of silence. Then Courtney spoke up.

"Well, I thought we all were adults here," she said while laughing, obviously a remark about my hairlessness.

My instincts took over and my hands covered my dick. Holly spoke next.

"Don't listen to her Jason, I think it's sexy," she said with a smile. "Come on in."

I slowly moved my hands and walked towards the pool, then hesitated for a moment. This was my first sexual encounter with a woman, and I was nervous. Then she broke the ice.

"Would you feel more comfortable if I got naked?" she asked.

Before I could reply, she reached behind and untied her top and revealed her beautiful breasts to me. Oh man, they were awesome. Her huge globes sat on her chest firm and proud and didn't droop one bit. Her tiny nipples were as erect as could be. She went under the water for a few seconds then came back up with her bottoms in her hand. She slingshot them towards me and they bounced off my chest.

"Join me," she said and used her curling finger to draw me in. I went to the edge and jumped in before I could get an erection, but mainly to see what she had below the belt.

The water was cold, and I'm sure it had an effect on me, but I didn't care. She turned around and swam away. Her perfect ass sailed across the top of the water. I tried to keep up with her but she was too good a swimmer. I didn't let up and tried to catch her. I could only imagine what would happen if I did. But alas, she was too graceful in her form and she stayed well ahead of me. After thirty minutes of chasing, I was spent. I leaned my back against the side and rested on the wall. She teased me from the other side.

"Can't keep up with me can you?" she said.

"Don't worry, I know you can't go forever," I teased. Carmen called out to me from her lounge chair.

"Hey Jason, come get some of the juice. You look exhausted," she said. I got out of the pool and walked to the table next to her. I poured a glass and drank it down. While I had the glass to my lips it came back to me that I was naked. Chasing Holly around the pool totally made me forget. None on the other girls seemed to mind though. They all were doing their own things still. Carmen stood up from her lounge chair.

"Well, since we're not being modest here," she said while blatantly staring at my penis. She untied her top and pulled it off. She untied the strings to her bottom and they fell to the ground. She turned to me and held her arms in the air as if to say "What do you think?"

"There, now I'm a little comfortable," I said nervously. I tried not to stare at her so I wouldn't get an erection. I was very hard to do. Her breasts were not as big as Holly's, but still more than a handful. She also shaved her pussy, so it was even harder not to stare at her pink lips below.

"Don't want to get tan lines, you know what I mean?" she said. "Do you want to read this book with me while I tan?" she asked.

"I guess so," I said. I was really nervous but I wanted to stay out here even if nothing was going to happen. I guess I enjoyed the hidden eroticism of the situation. I sat on the chair next to hers, then she moved hers closer. Carmen laid down on her back and moved so she was perpendicular to the chair. She rested her head on my thigh. My penis was inches from her hair. She brought the book up to her face and started reading. I tried to concentrate on what she was reading, but it didn't work. Just the fact that a naked woman was leaning against me, her head next to my penis, was more than I could handle. Her golden skin seemed to glow in the bright sunlight. Her huge breasts gleamed in under the sun and my cock started to rise. I tried to hide it but there was simply no way. She wasn't even done with the first page and my cock was at full attention.She moved her head a little and nudged against my dick. She noticed my hard on and sat up.

"Jesus Jason, she said we were all adults here. But the moment I get naked you get a woody. Can't you handle the sight of a naked woman? What are you, 12?" she said kind of harshly.

"I'm s-s-sorry," I stammered. God, that was lame. Jennifer piped in from the table beside us.

"What a woody it is though. Look at the size of that thing!" she exclaimed. I was really embarrassed and even ashamed, so I wanted to get out of there. Then Carmen did something that changed everything.

"Well, since I gave it to you, I should help you get rid of it," she said. Carmen stood over me and straddled my lap. Her tits were inches from my face. She grabbed my pole and I jumped a little. She slowly lowered her pussy onto my dick until I was buried inside her. Her pussy was so tight! She slowly rocked back and forth to get the rhythm going. I tried to hold out but the situation was too much. My dick spurted my cum deep inside her. Carmen seemed surprised at my sudden eruption.

"Wow, how about next time you let me cum too?" she snapped and got off of me. I felt even more embarrassed than I did before. She was about to leave until Jennifer spoke up.

"Look Carmen, He's not getting soft," she said. My dick was still hard as ever. "Maybe I could give it a try."

Jennifer sat down next to me. She looked so sexy in her teeny bikini. Her titties were a little bit smaller, but she was just as hot. She grabbed my cock and smiled at me so sweetly.

"Let me know how I'm doing, OK?" she said and took my dick in her mouth. I clenched the sides of the lounge chair as hard as I could. The wonderful sensation overwhelmed me. The feeling of her lips moving down my shaft and her tongue dragging across the crown made me moan out loud. So this is what a blowjob felt like! When the tip hit the back of her throat, it sent a new feeling jolting through my body and it caused my hips to twitch a little. Jennifer felt it and giggled with my cock in her mouth. That sent another sensation through my dick and I moaned again with pleasure.

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bygoldemerald© 10 comments/ 166234 views/ 96 favorites

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