Scarlett's Challenge

I parked in the bus area and walked into the school. It was West Springfield High School which oddly had the exact same architectural layout as my old high school across town and so I knew exactly where the library was located. I realized as I walked in that I was perhaps a bit underdressed for a trip to the high school. I was wearing a some heeled boots I wear when I want to look a little bit taller, my favorite pleated tartan mini-skirt, a pink tank top which was too short to cover my bellybutton ring and too light to completely block out my black bra. I had my hair back in a ponytail and I brought a dolly into the school with me. I noticed some of the office women looking at me disapprovingly while I walked past and I couldn't help but smile to myself. I hadn't intended to dress overly sexy that day but I had wanted to be comfortable. Hey, I am comfortable in weird stuff I guess.

Finally I had made my way to the library and I walked in and set my dolly next to the door. There were a handful of faculty members and students wondering around, looking at books. I walked up to the check-out desk and looked around. No one was there, so I rang the little bell. Almost immediately a girl came out from the little office behind the desk. She was gorgeous and she was smiling. I was immediately smitten.

"Hey," she said, "Can I help you?" she was about 5'5 tall and probably weighed around 100lbs. She had long red hair tied in long pig tails, her eyes were green and her face was innocent and beautiful. She looked like a movie star, the kind who would play the part of most popular girl in school. Squeaky clean and sweet. She had large, C-cup breasts and as she walked up to the desk I noticed her muscular legs. I could tell she was an athlete. Suddenly I thought to myself that "I hope she is a cheerleader," and then I remembered why. I laughed to myself and the girl raised her eyebrows at me. It was so sexy. I had to get myself under control here.

"Sorry, yeah I am Scarlett Byrne. I called yesterday. I am here to pick up any of your extra books," I said and she started nodding.

"Oh yeah," she said, "Mrs. Corliss said that you would be dropping by; there are three boxes over there by the door." She pointed towards the door where my dolly was located. I had walked right past them.

"Thanks sweetheart. I didn't think that you were the librarian," I said to her in an offhand way. I had to be the cool one here. She laughed a little bit.

"No, absolutely not. This is my class instead of study hall. I am a librarian aide," she explained to me as she played with one of her pigtails.

"Oh that's no fun. At least if it were study hall you could hang out with friends or at the very least do your homework," I said. Struggling to find some reason to stay and talk to her without being creepy. Luckily, she seemed to be in the mood to talk.

"I know!" she said, "I didn't even sign up for this. I wanted to have gym in seventh period so that I could just go right from here into practice. But they stuck me here instead."

"Oh," I said, circling like shark now, "You are on a team?"

"Yeah," she said, and then suddenly smiling slyly and blushing a bit, "Actually, this is my senior year and I am actually the head cheerleader." Jackpot.

"Oh my God!" I said, "That is so great! Congratulations."

"Thanks," she said, blushing now and staring at her feet. She was so demure and cute. I was finding myself not just wanting to try this for the challenge, but now I seriously wanted to go for it. I moved in for the kill.

"You know, I was a cheerleader too. I was never head cheerleader of course," I explained, "but I was a flyer. It helps to be tiny I guess." This was the truth of course. In setting up the challenge, I had promised Kegan that I would only lie to the girls I was going a little bit. That would help the challenge to maintain a certain degree of difficulty.

"That's so cool," she said. She was playing with her hair and looking at me. I couldn't be sure, but I was pretty sure she was returning my little compliments, "You definitely have the build for a cheerleader."

"Oh that was like 7 years ago," I said, now it was my turn to blush.

"No I am serious. You look like you could go right back out there and do it," she said.

"Hey, when is your next home game?" I asked her as I started to walk over towards my dolly. Just as I had hoped, she started following me towards the door.

"Actually, we have a game here tomorrow," she explained.

"You mind if I drop by and check you out," I said and paused for a moment, letting that sit for a moment, "I haven't even been to a high school game since senior night."

"Oh sure!" she said. I was a little surprised by how easy it had been to get her excited, but I wasn't going to complain. I loaded the books up onto the dolly and strapped them in. She helped me as well as she could and we made a little more chit-chat.

"Well thanks..." I hadn't gotten her name.

"Cindi," she said, "Cindi Fuller."

"Alright Cindi Fuller, I'll see you tomorrow night," I said. She waved to me once as I left. I rushed the books back to the truck and packed them in. I could hardly concentrate on anything else for the rest of the day. Somehow I managed to get to one last school before the offices closed at 5 and then I went back and unloaded the boxes at the store. By the time I got home I had decided not to talk to Kegan about my experience. I didn't want to jinx anything and besides, I really didn't want to fail and then have to deal with Kegan gloating and making fun of me for striking out. I decided that if by some miracle I was able to seal this deal that I would be able to tell her afterwards.

The next day I woke up and cruised around to other schools and picked up boxes of books but my head was elsewhere. I just kept picturing cute Cindi standing behind the desk in the library and it would give me chills. The days passed so incredibly slowly and I wondered to myself whether Cindi was as excited as I was about the evening. I was pretty sure she wasn't. But then, she didn't know the plan yet.

Finally, 6:00 o'clock rolled around and I made my way over to West Springfield. The game was supposed to start at 6:35 and I wanted to make sure I could get a spot near the lower part of the bleachers. I got there twenty minutes before the game started, bought some nachos, and then went over to find a seat. The team, apparently, was terrible that year and only about seventy people had showed up to see the game. The cheerleaders weren't out yet so I grabbed good seat down in the first row of bleachers. I had forgotten how much I hated football games.

The night air was getting a bit chilly and I put my jacket on to stay warm. I was wearing a pair of flats, a pair of tight jeans, a white t-shirt (with my favorite black bra underneath) and a jacket. It was still a bit cold. But finally, at long last the cheerleaders came running out onto the track in front of the bleachers. I saw Cindi right away. She was obviously the most beautiful girl on the entire squad. She looked gorgeous in her uniform. The shirt was very tight and let her entire arms hang out and just a little bit of her stomach. It was red and white. Her skirt was very short and pleated red and white. Her breasts bounced suggestively when she ran and she had the most gorgeous smile on her face. I couldn't tell for sure but I was pretty positive that she saw me.

She and her squad did their routine perfectly and I was truly impressed. They had lots of aerial work and they were all quite limber and skilled at the various splits and acrobatic maneuvers. It was almost sad when the game started and she was reduced to chanting at the tiny crowd to get excited. I tried to be lead in the cheers but it was a little embarrassing because so few people were into it. The game was over long before half-time and it was absolute murder to sit around and wait for it to end while West Springfield gave up touchdown after touchdown. I was impressed by Cindi's stamina. No matter how bad the game got, she just kept cheering.

Finally, the game was over and I had a chance to make my move. I wasn't really sure what it going to be, but I had to make a move. I walked down from the bleachers and started to head over towards the chain-link fence that separated spectator area from the track. However, before I got there, I noticed that Cindi was talking to one of the boys on the football team. He had jogged off the field and removed his helmet. I am not much in the ranking of boys, but he appeared to be quite handsome and I figured it was her boyfriend. I started to feel a little ridiculous now. Like I had come here just to be a creepy older woman and now she was going to run off with her boyfriend and I would go home and have to explain to Kegan where I had been.

However, just as I was preparing to slink away, I heard her voice begin to raise and then the boy yelled something back at her and then abruptly turned around and walked away. Cindi threw her megaphone across the track and then sat down with her back against the chain-link fence. It was the perfect opportunity.

"Hey Cindi. You looked great out there," I said, pretending I hadn't seen everything. Cindi was startled a bit and then she wiped some tears out of her eyes, smiled and turned to look at me.

"Oh hey," she said, and I was afraid that she had forgotten my name, "Scarlett! I am so glad you came." Her voice was a bit hoarse from crying and I felt a little bit bad.

"Yeah it was really good. Your squad is really good, even if the team is kinda rough. Hey is something wrong?" I asked.

"Nothing," she said.

"Oh I am sorry. I really didn't mean to pry or anything," I said and took a step backwards. She stood up quickly and put her hands out.

"Oh no! It's not like that. I am sorry. Well it's my boyfriend. We were supposed to go out tonight but now he says he is going to his buddy's cabin and I know that he is not going to just go there with a bunch of guys. There are going to be girls there. He's cheated on me before and I just know that he is going to do it again." she explained and then almost started to cry again before catching herself.

"That's terrible," I said and put my hand on her shoulder.

"I just...I just really needed him tonight," she said and I started to feel uncomfortable. I moved my hand from her shoulder, "Look up in the stands," she said and I did as I was told. There was pretty much no one there, "Do you see my mother?"

"I..." I started, but realized that she didn't really want me to say anything.

"No. No you don't. That's because every goddamn game she promises me that she is going to take one Friday off from going to the bar and she is going to come see me cheer. But, as usual she lies every time and now there isn't anyone who wants to be with me tonight," and with that she started to cry again. Now I put my arm around her and gave her a hug over the chain-link fence while she got herself together.

"You okay?" I asked, not really knowing what to say.

"Thank you so much for coming Scarlett," she said, suddenly turning and looking at my eyes, "You know there is no one in my life who ever comes through for me on anything and you promised to come here and then you did. I don't know why you want to be my friend but I am really glad that you do," she said. I felt guilty for a moment and then ignored it. My motives might not have been 100% pure but at the very least I was helping her now that I was here.

"Oh it was my pleasure. I have a bit of a deadbeat mother as well. Not to mention some really unimpressive relationships," I said, "Come on, let me take you out to get something to eat."

She didn't have a car so we took mine. I had bought it several years before and it was a bit of a beater but she didn't seem to mind. She was telling me all kinds of gossip from high school about people who I didn't know and places I had only heard of. She was very sweet and I decided it was better to just let her talk and get in a good mood. I was wearing jeans and she was wearing a cheerleader's uniform and so we decided it was probably better to just go to a casual dining place. We found one of those big chains stores like Applebee's or Ruby Tuesday's or one of those places. They are all pretty much the same anyway. They seated us and we ordered our food and relaxed. Cindi was in a better mood now and we were able to talk about more cheerful subjects.

I asked her about school and where she was thinking of applying to college and she asked me what I did for a living and where I lived. Soon I felt like we had known each other for years. I could tell that she had been serious when she said that she appreciated me coming to her game. She even seemed to look up to me when I told her about my job and about my mom kicking me out. She didn't bat an eye when I told her I was a lesbian (I wanted that seed to germinate, so I said it sort of early). I felt like she looked at me as one might look at a successful older sister or cousin. It felt nice.

"So what's this boyfriend's problem?" I asked. I had to touch this subject if I want to go any farther so I decided to put it in a way that invited bitching rather than crying. She obliged.

"I don't know. He is just kind of a dick sometimes. Can I be honest?" she asked.

"Absolutely," I said.

"I think that he is frustrated with me. I mean I give him hand jobs every once in a while and we make out a lot but I think he wants to have sex and I told him I don't want to get pregnant in high school because I want to go to college and I don't want to be like my mom. So he tells me I should give him a blowjob, but I think that that whole concept is kind of gross," she said in what seemed to be one breath. As though she had been considering this a long time and then took the first opportunity to blurt it out.

"Well I definitely say don't give in. If you have a dream and you think that having sex with him could destroy it, I say you have to stick to what's good for you," I said and I was speaking the truth, "but, with that said, I can understand why he wants you Cindi. You are beautiful. But you are a woman. You shouldn't be messing around with boys anyway," I said. She blushed and thanked me. Our food arrived and we ate quickly and quietly.

"When did you lose your virginity?" she asked me as we finished and I blushed.

"Well I was 18 I guess. I had sex with one guy in my life and that was it. His name was Scott. He is actually engaged to one of my friends right now, which is kind of weird. I didn't enjoy it and I had already known I was a lesbian. I was just fighting it. You know?" I stirred my coke with my straw. She was looking at me intently. Suddenly, she leaned across the table and gave me a quick, sweet kiss on the lips. I was shocked as she sat back down, smiling at me.

"What was that for?" I asked.

"Just... thank you," she said and then looked at me with a seductive look in her eye. I didn't need to see anymore. I knew what she was trying to tell me. I immediately paid the bill and we jogged back out to my car, holding hands and giggling.

I knew that we couldn't go back to my place or Kegan would see and I didn't want to explain Kegan to Cindi or Cindi to Kegan. I drove us quickly over to the Holiday Inn. Cindi was talking nervously about school and about cheerleading and I had to feign interest. I had only one thing on my mind.

I told her to wait in the car while I ran in and rented a room. I got the key and we parked the car and made our way to the room on the third floor. She was really giggling now as I opened the door. She flopped herself down on the bed, we had gotten a king sized room. I closed the door behind us and stood with my back to it.

"So..." I said and she looked up at me.

"Yeah..." she said to me. I knew that it was up to me to make a move because she had never done anything like this before. I lay down next to her on the bed and we both rolled over so that we were leaning next to one another, looking into each other's eyes. She was beautiful. I closed my eyes and kissed her. Not the little peck from the restaurant, but a real kiss. Our lips locked and my arms went around her body. My tongue entered her mouth and tasted her tongue. She moaned into my mouth and I felt my body grow weak.

I rolled over so that I was on top of her and she wrapped her legs around my waist. I leaned forward and kissed her again, my hair draping over her face and I looked into her eyes. I could tell that she wanted this and I let any remaining guilt I had about the situation melt away. I kissed around. I felt her hands on me. One was rubbing my side and the other was clutching the back of my head, pulling me in.

Finally I broke the kiss and got up on my knees. Cindi opened her legs and I was able to slide out and stand in front of her. She was lying on the bed, with her legs spread open, looking at me. I could see her white panties and it thrilled me. I decided to give her a thrill. I pulled my white t-shirt up over my head and threw it on the floor. I then unzipped my pants and slide them down. I was standing in my black bra and my black thong with red lace trim and her eyes were on them. I smiled.

"You like what you see?" I asked and she nodded. I reached behind my back and unhooked my bra. I brought my hands forward and let the bra slide off of my arms and land on the floor. My nipples were little pink bullets. Finally I slid my thong down around my ankles and threw them off. My pussy was waxed completely and I felt good showing off my little pink pussy lips. Cindi gasped when she saw it. By now she had slid back so that she was sitting at the top of the bed with her back against the headrest. I got on the bed on my hands and knees and crawled towards her slowly. She was biting her lip and looked frozen.

I straddled her hips and took my left breast in my hand. I carefully placed it against her mouth. She hesitated for only a second and then she began to suck on it. I moaned loudly and my whole body shook. No one I had ever been with had ever sucked my nipple like that. Her tongue danced across it and she bit on it gently and my entire body threatened to melt. I popped the nipple out and took my other breast in my hand and put it against her mouth. If anything it felt even better this time and I could feel my pussy dripping onto her legs.

I popped that nipple out as well and sat for a minute straddling her. I bent down and kissed her again. I started to lean back and she came with me. I put my arms around her and easily unzipped her cheerleader uniform. It slipped off easily and she lay in her bra. I unhooked that as well and took it off. Her breasts were perfect. They were just the right size and she had medium sized, pink nipples. I took one in my mouth and tried my best to mimic her actions. She moaned and arched her back and then fell back on the bed. I followed, licking her nipple and with my hand, rubbing the other one. She was wiggling and moaning underneath of me and I could feel her hips rubbing against my leg. I knew she was ready.

I moved down her body and pushed up her skirt. I took her little white panties in my hand and pulled them down and removed them. She had shaved her hair into a little landing strip, something that I found to be incredibly sexy. Her little pink pussy lips were glistening they were so wet and her panties felt damp in my hand. I got down on my knees in front of her pussy. I breathed deeply and took in her smell. She smelled clean and sweet and I was intoxicated. I leaned forward and gently kissed her clit. A tremor rushed through her body. I extended my tongue and began to slowly and carefully lap at her pussy. Her skirt fell down over my head but I could feel her rubbing her own breasts and I could hear her moaning deeply.

I loved her taste. It was unlike any pussy I had ever eaten before, it was so pure and it tasted good. She was really enjoying the lapping and I was deciding to kick it up a little bit. I took my right hand palm up and carefully inserted my ring finger into her pussy very slowly, right underneath of my chin as I lapped at her clit. She thrust her hips hard against my finger and she shook a little bit. She screamed so loud I thought that someone was going to come up and knock on the door.