tagLesbian SexScarlett's Challenge

Scarlett's Challenge

byYKN4949©

Chapter 1: The Gauntlet is Thrown

I had my hand underneath of her shirt and I was rubbing her breast through her bra. She was moaning around my kiss and I could feel her rubbing her hips against mine. Occasionally her hands would brush against my breasts and I would feel my entire body shudder. I decided to go for it one more time. I took the waistband of her panties in my fingers and started to slide them off down her hips. Instantly, her hands were on my wrists and she was rolling her eyes and pushing me away.

"Listen Scarlett," she said, "I have told you before, I don't fuck girls. We can kiss and you can play with my boobs but that's it." I couldn't believe her. How was she able to kiss so passionately and rub me so openly but still claim that she didn't want to go any farther. I was surer than ever that she was just playing games with me. I decided to play along.

"Isn't there anything I can do to change your mind?" I said, biting my lower lip and trying to be as sexy as I could. To my surprise, she seemed to consider it.

"Well..." she said, "Maybe there is something you could do."

I guess I should drop back a minute and catch us up to this point. My name is Scarlett Byrne and I am 25 years old. I have been told, and tend to believe, that I am very beautiful. I am a petite girl, 5'2 and around 90lbs. I have long, straight, brown hair and large brown eyes. I am especially proud of my long eyelashes and upturned pixie nose. I have thick, pink lips and dimples when I smile. I have that sort of All-American girl face. My body is, as I said, petite. But it is very womanly nonetheless. I have small, 30-A breasts and hips that flare out just enough. I am a big exerciser and so my stomach is flat and my belly button is pierced and I have a toned, muscular butt. My legs are long given my height and very shapely. I used to get made fun of for my tiny feet but I have always liked them and now I think people think they are cute and make me look girlish.

I have been living on my own ever since I graduated from high school. My mother and I had never gotten along and when I told her that I was a lesbian she kicked me out and I have been making it on my own since then. I worked a couple of odd jobs and made a little bit of money. I lived in ratty trailers and with some pretty scary people for a while. I tried to figure out what I was going to do with myself.

One day I was walking past a parking lot near my job and I noticed an old used book store with air conditioning tucked into a corner. The hotel I was living in at the time didn't have any air, so I decided to go browse around and try to store up some of the cold for later use. I went inside and loved it immediately. It was overflowing with old books and it was dark and quiet and had that smell of old paper. I walked around for a while and enjoyed the ambiance. Eventually, I decided I had wondered around long enough. I found a book and walked it up to the checkout.

The guy running the place was absolutely ancient. He looked like he was about to keel over at any second and I tried not to talk too loudly and risk knocking him over. I told him how much I admired his store and he seemed genuinely grateful.

"Yeah, she's a good old place," he replied looking around, "It's a shame it's going to be gone in a few days."

"What do you mean?" I asked, honestly dismayed. I had been looking forward to coming back.

"I am retiring on Saturday. I have been at this too long. I am ready for a break. Heading on down to Florida to live with my daughter," he explained to me and I could tell that he was relieved, but the next question I asked seemed to break his heart.

"But why does this place have to close?"

"No one wants it. The interstate took most of the business off of this road and the profit margin has gotten pretty thin," he explained. I asked him how thin, "I just a couple hundred a week after taxes."

"Do you own the building?" I asked and he nodded. He went on to explain that he couldn't unload the place and that he was going to sell it to the bank for next to nothing so that they could tear it down and extend the parking lot.

"I have an idea," I said. With that I set in motion the process of buying the old store. In exchange for $100 a month to the old man, I would run the store and keep whatever profits came after that. I went with him and he changed his will so that when he died the store would be mine. By that Saturday, the store was essentially mine and I actually owned all of the books outright and I was incredibly excited.

I threw myself into the store and fixed it up, I put ads in weird little newspapers where I could get free or cheap space. I made cheap tea and gave it away for free. I also devised ways to get my hands on books cheaply by taking old books from libraries or damaged books from wholesalers. Finally, I catalogued everything that the store had with a computer and even did research and found that some of the older books were quite valuable. Now I had a sort of hippie clientele that came in and read and sometimes bought books. I also occasionally had book dealers and collectors come in and pay good money for some of my rarer pieces. Finally, I got licensing from the local university to buy back and sell some of their text books at an enormous profit. All in all I was able to maintain the cute atmosphere at the store but still make a little more money than the old man had been able to make.

For a year after I opened the store I lived in a little store room in the back. It wasn't exactly glamorous but I didn't mind. I just didn't bring any dates back home. After that year the old man died down in Florida and the deed to the store came in the mail. I decided to move into a real home. A store across the street had an apartment above it and the rent was relatively low and the commute was fantastic so I rented it. It was a cute little place with a kitchen/living room, two bedrooms, and a bathroom. For a while, this worked out very well.

However, one year the economy took a big drop and the demand for some of my more expensive books dropped off. I realized that in order to make money I was going to have to figure out a different revenue stream. I was still making enough money to keep up the store and to pay my rent but at the end of the week I ended up running low on food and I had to cancel luxuries at my home like cable and internet. I decided to rent out my extra room to a college student to make ends meet. The college was huge and they had a severe housing problem. Making it worse was the fact that rent in local apartments was astronomical. I would be doing well by doing good if I rented the room out cheap to a student in need.

The first girl who came in response to the room was Kegan Kelley. She was a 19 year old freshman and quite possibly the most beautiful girl I had ever seen in my life. I rented her the room on the spot. Her parents were quite wealthy and I was actually able to get her to pay a little more than half of my rent. Beyond that, she was 5'9 110lbs, she had long dirty blonde hair and blue eyes. She had the face of a movie star and the most amazing body I had ever seen. She was built like a model with long legs, a thin stomach, elegant features, and small, perky breasts. Beyond that, she was a very sweet girl and we got along very, very well.

She moved in a few days later and disaster was averted. Furthermore, I found that I liked having someone in the house. She was impressed with my cooking ability and she herself was actually quite handy when it came to things like broken light bulbs or dirty sinks; things about which I had no knowledge about. Further, she guided all of her cute friends to my store and they spent money on text books and other little things and my life got better. I also came to have a friend, despite the fact that she was 6 years younger than me. We would sit up late and talk and drink coffee in our pajamas. Despite the fact that I thought I was falling for her, I never told her that I was a lesbian and I decided not to act on it. She occasionally had a boy over, but none of them ever spent the night and I just sort of figured we would both have sort of asexual existences within the apartment. However, one night things changed.

Kegan had gone out with some friends for the evening, to a party of some sort at a frat house. I was in for the night. It was a Thursday night which meant that if I wanted to go do something for the weekend I had to get my books in order and find out what sort of paycheck I would be able to give myself for the week. I had just finished up and was packing my stuff into my backpack when Kegan came home. She was hammered.

"Hey Scarlett," she said, far too loudly, "How're you?" She sort of stumbled into the room and flopped down on the chair.

"Good," I said giggling, "You?"

"Drunk," she said and we both laughed. When that subsided we were both quiet for a while and I figured she had fallen asleep. I got up and put my bag away and then went to my room to get ready for bed. I decided to let her sleep on the couch. I was just taking my shirt off when I looked at the door. She was standing there, with her mouth open, staring at me. I blushed.

"What're you doing Kegan?" I asked, feeling embarrassed but also very excited.

"You are so pretty," she explained, "Do you think I am pretty?"

"Very," I said, feeling my heart trying to burst through my chest.

"You know Scarlett. I am not gay or anything. Really. But sometimes I just like to make out with girls," she said and started walking towards me.

"I am a lesbian," I told her and she stopped for a second and looked at me. Then she smiled and kept coming towards me. I froze but soon she was right next to me. She leaned forward and gave me a kiss. She tasted like vodka but it was still a very sweet kiss. She put her arms around my and kissed me. I help her and kissed back. We fell backwards onto the bed and our tongues explored the inside of each other's mouths. Finally it broke and we looked at one another. I knew that this was wrong but I wanted it so badly. I kissed her again. For a long time we simply lay in bed, our legs and arms interlocked around one another and our lips locked together. My pussy was absolutely dripping but I was nervous to go any farther.

Finally, after what might've been an hour of gently kissing and holding one another, I reached my hand to her breast and rubbed it gently. For several seconds she moaned and really seemed to enjoy herself. Then she put her hand over mine.

"No Scarlett, just making out," she said and I felt so frustrated and angry, but I wanted to kiss her and so I didn't stop. Eventually we fell asleep that way, entangled in one another, our lips touching.

We both woke up the next morning at around the same time and both of us were a bit embarrassed. She got up and went to take some aspirin and get a shower. I made a good hangover breakfast with eggs and bacon. She came into the kitchen and we ate quietly for a few awkward minutes. Eventually she spoke first.

"Sorry I was a mess last night," She said, not taking her eyes off of her food. I felt terrible.

"No, I am sorry I tried to take advantage of you," I said, feeling dirty even as it came out of my mouth. She giggled a little bit.

"I think I threw myself on you more than let you take advantage," she said and I giggled back. Suddenly, things felt a lot lighter and we chatted about her night and how she was. She expressed surprise that I was a lesbian briefly but we didn't talk about much. Finally, she was done eating and decided to head to school, I had to go and open the store.

"I'll talk to you later," I told her and started to walk out the door, but she stopped me.

"You know I wasn't just lying or talking because I was drunk you know," she said as she collected her books.

"What do you mean?"

"I really do like to make-out with girls every once in a while," she said and she gave me a mischievous look as she brushed past me in the door way, "If you're interested."

From that point on we would occasionally have a little date at home where we would eat and rent a scary movie. We would make popcorn and get a little blanket and hunker together and watch, and scream, and then kiss. Eventually we even got to the point where she would let me fondle her breasts with my palms through her bra and she would very occasionally do the same. But anytime I tried to go farther, she quickly stopped me.

I think this brings up back to where we started. Kegan had finally relented a little and had indicated that in fact, there might be some way for me to get into her pants. My heart was racing like it had been that first night and I was desperate to do anything.

"Well what do you want?" I asked, trying to stay calm and cool and sexy.

"What about a challenge?" she said and her eyes lighted up as though it was coming to her suddenly, but I knew her pretty well. She had been planning this for weeks. She was always scheming. I had learned this through the months she had been with me. She had a goal, like that night she kissed me, she had been planning to do that for some time, she just got drunk to cover it. Another time, she had meticulously inched her food in the refrigeration to the left into my area, a bit by bit for weeks until she claimed an entire extra shelf and then feigned ignorance when I confronted her. It was always small little things like that; I really found it more cute than anything else. I found everything about her to be cute in all honesty.

"What do you mean a challenge," I asked, but I was enticed.

"Well you are a lesbian and I am straight and you want to seduce me right?" she asked and I reluctantly nodded in response, "Well prove to me that you are really good at seducing straight women. Give me reason to believe you're worth playing for the other team." I was confused.

"I guess I am still not really getting it," I told her.

"Okay, let me see if I can spell it out," she said, pretending she was annoyed but really loving how much I wanted this, "We will come up with a list of 5 girls or types girls, straight women who, for whatever reason, will be really difficult for you to seduce. If you seduce them all you can have me."

"I like it," I said, my mind racing and unable to comprehend much beyond the last sentence.

"If you get them to do some really kinky stuff, I will let you do anything that you want with me," she said, blushing and staring at me. I could tell that she was going to be rooting for me, in secret, "But if you don't do it, you have to stop trying to fuck me forever."

"Agreed," I said, finally considering what she was offering in a more rational way in my mind, "So what kind of girl do you have in mind?" I had to admit I didn't like my odds. I was 25 years old and had 4 sexual partners in my entire life. I was a bit shy and there weren't many lesbians in my little town. I had to try though; Kegan was the kind of girl I wanted.

"Well the one girl I have in mind already is the girl in charge of the University Campus Baptist Society. She is always protesting abortion and gay marriage and stuff. She would be tough I would imagine. She is the first one," Kegan said and my heart sank. This was supposed to be a challenge, not an impossibility.

"Good lord Kegan. I have to theoretically be able to get this girl. This is impossible," I said. Kegan was pretending she hadn't heard me. She stretched out on the couch and let her hair fall over her face in a very sexy way. She rubbed her body as though she was stretching, but she was really just showing off. It was working.

"Well if you don't even want to try, I guess we can just call it all off," she said, looking at me though her hair and smiling a devil's grin.

"Who else?" I asked and she giggled at me.

"Well you can think of some too. Don't just rely on me. I mean you have to run it past me first, but you can try too," she said.

"Oh, okay," I said. We sat for a while, thinking. I just considered all of the options before me and was almost unable to think.

"I've got one," she said and I turned and I looked at her, "Okay, so girls in college are going to be a little bit open to experimenting. That's not really a challenge. However, girls in high school. That's a different matter. I want you to fuck a girl in high school. But not just any girl, I want you to fuck like the queen bee of a school. The one who has a football player boyfriend and wants to pump out his kids. I want you to go after...the head cheerleader at a high school," she said. I was a little stunned by this suggestion. However, cheerleaders had always been a huge turn-on for me. I just nodded at her while I considered how to do this. Needed to find an 18-year-old high school cheerleader... "I got one," I said suddenly, "I have a friend who is getting married really soon, like in the next month or so. I bet it would be really tough to get to her. I mean she is going to be into her husband and everything. It should be great," I said. Kegan considered it for a while.

"How long have you known her," Kegan asked.

"Oh since we were little kids. We were in the same elementary school growing up," I explained and Kegan seemed to light up.

"Oh that is so dirty. She is on the list," she said. I could tell that this was really exciting her and in turn it excited me as well. She came up with another idea very quickly, "Hey, did you parents have any friends growing up, or like neighbors or anything?" she asked. I considered it for a while. My mother didn't really have many friends.

"Well, there was Mrs. Selber. She lived down the street. She had a giant hairy mole," I said.

"Oh yes her!" Kegan said laughing. Then I realized something.

"Oh you know what? Right next door to my mother was a woman. Mrs. Something... Oh yeah, Mrs. Hoke. She was my mother's friend. They walk to church together and they get together to watch American Idol. She is a little bit younger than my mother though, like 43 or something like that. She was pretty hot the last time I saw her," I said, remembering Mrs. Hoke and feeling very excited by it.

"Perfect," Kegan said. The last one took a long while. We were both thinking but nothing was coming to mind. I started thinking about the other people we had already considered. I was thinking about my friend and being in third-grade with her when I was suddenly struck by something.

"I've got it," I said. Kegan shook her head out of her stupor and looked at me.

"What?' she asked.

"I told you about my friend who is getting married and you were asking about when we met. Well I am just remembering that my third-grade teacher that year. She was very young, it was her first year, she was like 23 or something like that. Third grade was like 16 years ago for me, so she is still pretty young. It would be pretty dirty to go after her, don't you think?" I asked and Kegan's eyes got wide.

"Perfect," she said. She leaned forward and gave me a kiss. I put my arms around her and kissed her deeply. We went to bed a few hours later and as she was closing the door to her room she spoke to me.

"Good luck Scarlett," she said, "You're going to need it."

Chapter 2: The Cheerleader

For about a week I didn't think anything more of it. The store was an absolute disaster as I was trying to clear out space for my annual trip to local schools to pick up unwanted library books. I had rented a truck for that purpose and after a fire sale I was ready to roll. I got in the front seat of the truck and headed first to one of the local middle schools. I managed to a get a good number of decent books there and then I headed over to one of the high schools. It was closing in on the end of the school day and I wanted to slip in and out before there were hundreds of new drivers waiting to crash into my rented van.

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