Scarlett's Challenge

Carefully, I moved my hand farther up her soft, supple breast until my finger grazed her nipple. She didn't stir in the slightest as I touched it. It was small and quickly became very hard. I slowly took my fingertips and circled them around her nipple. With my other fingers I very slightly kneaded her breasts. She moaned in her sleep and pushed herself back against. I opened my palm and engulfed her entire breast within it, carefully. I kneaded it with my whole palm, paying particular attention to her nipples, being soft and caring with them. I wanted my touch to be ever so light. She was still moaning and her body writhed in her sleep. I moved my hand down now, and slowly I began to play with her other breast. I used the same care here as I had before, touching with my palm and fingers and gently kneading but applying as litter pressure as humanly possible. She continued to respond to my touch, squeaking in her sleep and moving her head around. She looked beautiful with her eyes closed and her hair covering her face. I leaned forward and gently kissed her neck. I continued to kiss her neck and gently stroked her breasts for a long time.

I next removed my hand from Tori's shirt and gently rolled her over so that she was laying on her stomach, still deep in sleep. I took her panties in my hand and carefully pulled them down her legs and threw them off. Her ass was absolutely perfect, big but not too big and muscular but not too muscular, with a little pink asshole. I put my hands on either side of her body and gently lowered myself until my face was just a few inches from her asshole. I could smell her pussy and could see than it was dripping onto the blankets we had laid down on the bottom of the tent.

I stuck out my tongue and pressed against her cute little asshole. I loved to eat asshole and her's was amazingly cute. It tasted wonderful as my tongue lapped at it. I didn't put too much pressure on her asshole, just allowed my tongue to rub over her as softly and carefully as possible, bringing her taste in and listening to her moan. Her pussy was getting wetter by the second and I had an idea. I sucked once on her asshole, just a little bit of pressure, and then licked thickly and fully one last time.

I leaned over onto my left hip and left elbow and then I took my right hand and very carefully rubbed it against Tori's pussy. I could hear her breathing shallowly and lustily in her sleep and she was letting out pathetic little moans every few seconds. Once my fingers were soaking wet with her juices, I rubbed my fingers all over Tori's asshole. I repeated this process a few times, enjoying the soft wet feel of her pussy and the little bud of her asshole. When her asshole was as completely soaked as her pussy, I took my middle finger and pressed it against her asshole. I applied the slightest pressure and quickly my finger was sinking into her virgin asshole. It was like her body was trying to suck my finger in. I took my index finger and set it next to my middle finger and soon the tips of both were sinking into her asshole. I worked carefully and lovingly, working my fingers deeper and deeper into her ass. I was surprised both by how tight she was but also by how willing her asshole was to make way for my fingers, to allow me in. After a few careful minutes of gentle work, my last knuckles pressed up against the skin around her asshole and they could go no further. I was just about to start rubbing her pussy as well when she stirred.

"Oh God," she said suddenly, then her head turned and looked down towards me, "Oh shit! Scarlett what are you doing down there," she said, a little disoriented. I decided to take advantage of this. I gently started to rub the inside of her ass with my fingers, careful not to move them around too much, just enough for her to feel the delicate pressure.

"You are so tense all the time baby," I cooed, slowly moving.

"I am tense!" she moaned and put her head in the pillow.

"I was just trying to help you relax. This job of yours, taking care of the Action Committee, it is too tough to do without a little bit of help. I am not a good speaker or a good administrator. I am helping you the way I know best," I said.

"This is very, very wrong Scarlett," She said, coming awake more now, "This is everything that we stand against!" I stopped moving for a moment. My blood was running cold. I had only one option now and it was a huge gamble. The entire Challenge rested on her response. Not to mention the off chance of jail time. I slowly started to pull my fingers out.

"Do you want me to stop," I said, sounding as embarrassed and ashamed as I could.

"No!" she said loudly and quickly and pushed her hips back into me, filling her asshole again with my fingers, "Don't you ever just want to do something because it is wrong?"

"Yeah baby," I said and slowly started to rub her again. She was talking quickly now, although she would occasionally become silent or moan. She was telling me about her inner struggle. Her desire for bodily lust but her purpose in the Lord. She talked about her sexual and spiritual needs and how they always felt like they were in conflict. She said that she had wanted to lose her virginity but hated herself for feeling that way. She was obviously in a lot of emotional strain, but she was taking it out on her little asshole, grinding herself into my fingers while she spoke.

"Tori," I said, "Sex is a gift from God. If sex were just supposed to be about procreation and you were only supposed to do it with certain people at certain times he wouldn't have made it feel so good. He wouldn't have made it work with people of the same sex. He wouldn't have made masturbation possible. He could do all those things if he wanted to, but he doesn't. Do you think God is out to trick you and trip you up," I asked. She moaned loudly and I could see her biting her lip.

"Oh Jesus," she said, "No. God loves us. He wouldn't purposefully try to deceive us," she said and it came to her as a revelation it seemed. She started fucking even harder.

"Do you like have my fingers in your asshole?" I asked. She seemed shocked.

"Is that what you're doing down there?" she asked and I nodded, "I love it," she answered. I continued to work slowly. She surprised me though. Carefully, she threw one leg over my head and spun herself around so that she was laying on her back and watching me. My fingers swirled in her asshole, but they stayed in. She seemed to really enjoy that feeling and she smiled down at me. Her nipples were very hard and soon her pussy was dripping down onto my fingers.

I started fucking her ass with my fingers even harder than before. I looked at her pussy, which was shaved bare just as mine was. It was very cute with slightly brown pussy lips. I leaned forward and kissed her pussy once before starting to lick her. I lapped at her as I had her asshole earlier, running my tongued from my fingers at her anus all the way up to her clit. She started playing with both her nipples while she watched me. She was squirming a bit but her eyes were focused on me, watching and enjoying my actions. She took one of her hands and gently played with my hair.

There was little build-up to her orgasm. One second I was playing with her asshole and gently licking her clit and the next she was shaking and moaning and grabbing my head with both of her hands and pushing my face harder into her cunt. She came hard and for a very long time and I just kept fucking her with my tongue and my fingers and it slowly subsided. She lay panting while I carefully removed my fingers from her asshole and licked her cunt one last time.

"Want to try?" I asked.

"Yes," she said and I could hear that same old passion in her voice, only this time it was directed towards me. She sat up and pushed me down onto the ground. I landed on my elbows and spread my leg. She crawled in between and them and our nipples touched. This drove me crazy and I arched my back into her and moaned. She leaned forward and caught my moan in her mouth, sucking it in and driving her tongue into my mouth. She put her left hand behind my head and with her right hand she started to rub my pussy. Her fingers were so delicate and soft. I felt like I was going to explode.

Slowly she moved her hand down to my anus. I knew she wanted to try to do for me what I did for her. She was very careful and only used her index finger, but she quickly and forcefully inserted her slender finger into my asshole, filling me up and making me moan. She started sucking on my nipples while she continued to fuck my ass with her finger. She started to rub my clit with the back of her thumb, rubbing the nail against it gently. I began to squirm and my pussy was soaking the entire blanket beneath us. I was right about her passion. She was attacking me in a way no woman had done before. Every inch of her seemed to vibrate while she fucked me. She kissed like we were going down on the Titanic and she held me tight in everything that we did.

She didn't even get a chance to eat me out. I started bucking quickly. I had the most intense orgasm I could remember in my life. I shook all over and I was afraid that someone was going to come running over to the tent because I was screaming so loud. It felt like it lasted forever and the pleasure was so intense it almost hurt. To try to quiet me down, Tori placed her lips over mine and again caught my noise. She slowly pulled her fingers out of my ass and put her arms around me. Kissing me and falling down on top of me while my orgasm subsided.

We lay there for a long while. Talking quietly about nothing in particular and kissing. Eventually we fell asleep that way, her lying between my legs and our pussies on top of one another. When the alarm from the author went off in the middle of the night, Tori quickly switched it off, gave me a deep and passionate kiss, and then we again fell asleep in each other's arms.

Chapter 6: The Teacher

"Quick sweetie, come into the new kitchen!" was the first thing I heard when I made it back into my store the next morning. Sweetie. I couldn't believe she had just called me that from upstairs in the new room. The workers had been at it all week and I guess they were finished. I went upstairs and I saw Kegan standing in front of our new oven with a big cute smile on her face.

"Its great!" I said and I meant it. It was much bigger than the kitchen/living room in the apartment and it looked so slick with all of the stainless steel appliances. The entire house looked brand new. There were wood floors in the two side rooms, black and white tile in the bathroom, and slate tile in the kitchen. The walls were freshly covered in paint and it seemed that all we needed to do was to move the stuff over from the old apartment and give my month's notice to the landlord.

"I can't wait to move in!" she said, and then she crossed her arms and raised her eyebrows, "I was hoping that we could celebrate last night by bringing the couch and the TV over here to watch a movie but you were nowhere to be found."

"I told you last week, I had to go protest with your little friend Tori," I said, trying to remember if I had actually told her.

"Oh a protest! How'd it go?" she asked, hoisting herself up and sitting on the kitchen counter.

"Didn't happen," I explained, purposefully leading her to ask more questions.

"Why not? Did you guys scare the abortionist or gay person off?" she asked.

"It was a transgender woman and no we didn't even try to chase her off, it seems that Tori Miller had had a big night with a certain young lady and didn't have the energy to get up and harass anyone," I explained.

"You didn't!" she exclaimed and then slowly drew the entire story out of me. She called me nasty for starting to fuck a girl while she was still asleep and I just shrugged my shoulders. She agreed that this was my kinkiest conquest yet and probably the most unlikely.

"So I am really close now I guess," I said to her and she nodded her head. "You know what that means," she said to me and jumped down from the counter. Simultaneously we ran to one another. Our arms were around each other and our tongues were within each other's mouths in a moment. We lay down on the floor and Kegan wrapped her legs around my waist and I put my arms behind her neck. Her hips ached against my body and her hands soon found their way to my breasts. She was rubbing my nipples through my shirt and our tongues danced together. Suddenly, she stopped.

"No, No, No," she said, unlocking me from her legs and then pushing herself back, "We had a deal and I don't want to change it now. Everything is going so well and I really do not want to screw it up." She stood up and straightened her shirt, "Come on, let's go start moving the stuff."

I sat on the floor, dumbfounded. I loved Kegan and I could tell that she felt the same, but she did some things that I just couldn't understand. She was an enigma. Probably part of the reason I was so into her. So I shrugged my shoulders and headed over to the apartment.

The next week I told the landlord that it was going to be the last month I paid for the apartment. My security deposit covered that month's rent and so, over the course of a weekend, we moved all of the stuff over to our new place, except for one of the beds. So we had a new home with a kitchen, a living room, a bathroom with a claw foot tub, and a small living room. It was great and I couldn't wait for our first night in it together. That was until Kegan through a wrench in that plan.

"Hey Scar," she said to me as we got the last bit of furniture together.

"Yeah?"

"Spring break starts tomorrow. I haven't been home to see my folks since Christmas. I think I had better head home until next Sunday and make sure that they are doing alright," she said. Kegan rarely showed anything vulnerable, but I could tell she wanted to go home. I decided not to make her feel uncomfortable.

"That's fine babe," I said, "We will just have our first night together next week."

"You are so great!" she said and threw her arms around me and gave me a kiss. A few minutes later she was all packed up and heading out the door. I was a little disappointed, but I decided to use the opportunity to its fullest.

I had contacted the local school board recently and explained to them that I had just recently cleaned out my bookstore and had found dozens of unique children's books that were both valuable and edifying to the children. They sent someone over to the store to look through the books and they enthusiastically agreed to buy the books. I then decided that I would donate the books in order to ensure that the school was willing to let me keep other old books when they were finished. Of course I didn't say that, but I felt it was a pretty good chance to do well while doing good.

I asked if I could deliver the books to my old elementary school, Margaret Cantor Primary School. They agreed and on the Thursday of Kegan's spring break I packed up the boxes into my car, put a dolly into the trunk and headed over to the school. It always felt weird walking into one of my old schools, especially the elementary school. Everything looked so tiny by comparison to what it had once been.

I carted the books over to the library and it made me think of Cindi. I almost laughed when a haggard, bald, female library came up to grab the books and warmly thank me for the donation. Not exactly like Cindi, I thought to myself. After she signed for the books and helped me unload them I thanked her and headed out the door. It was around 3:45 and the students had left 45 minutes earlier. I decided to go take a look around my old stomping grounds.

I saw the place where Shirley Whitmore peed her pants in kindergarten right next to the art room, I saw the lunch room where a boy push me out of my chair and chipped one of my baby teeth, and I saw the water fountain where Bobby Franklin gave me my first kiss in the fifth grade. It was a regular trip down memory lane. Finally, I came to my third grade classroom. The sign over the door indicated that Ms. Tapper was still in that classroom. I walked over and looked in the door and saw her working at her desk.

I was stunned. She had been a brand new teacher my third grade year, probably around 23 years old and youthful. Now she was 16 years older but she looked almost exactly the same. She was still very petite and had long, black hair and brown eyes, not a wrinkle or a hint of gray in her hair. Her skin was a beautiful olive color and she had that cute Jewish look that I really enjoyed in a woman, with soft features and a prominent, but perfectly proportionate, nose. Her body was still very toned from what I could see as she sat in her desk grading papers, although her breasts looked larger than I remembered. All in all, she was at least as beautiful as she had been all those years ago when I was her student. I was glad that I had included her on my Challenge.

I opened the door quietly and she walked in. She kept working for a few moments without noticing. She suddenly realized that someone was in her room and she lifted one finger briefly, letting me know that I should hold on for a minute. Finally, she looked up smiling, but didn't seem to recognize me.

"Hello," she said after a moment, "Can I help you?"

"You don't know who I am do you?" I asked. I know that teachers probably hear that constantly but I didn't know how else to do it.

"I am sorry I don't," she said and I respected her for her honesty.

"You were my third grade teacher," I said and her smile brightened up.

"Oh goodness," she said in a very wholesome way, "I have had so many students here but let's see if I can guess. You are a little bit older than most of the former students who still come in here, so you must have been in one of my first two or three classes."

"I was in your first class, actually," I hinted. She put her finger on her chin and tapped it several times, obviously thinking deeply.

"Scarlett Byrne?!" she said suddenly and seemed positive.

"Yes!"

"How're you. Oh my God, I remember when you were just a little girl. I can't believe you are already grown up. It makes me feel like an old woman," she said as she got up from behind her desk and then ran around and gave me a big hug.

"You look great," I said, reacting to her 'old' comment, "You look exactly the same as you did when I was in third grade."

"You always were a sweet girl," she said and gave me another quick hug. She asked me about working and whether I had started a family. I told her about my store and the fact that I was single. She seemed genuinely happy to see me. It reminded me of how sweet she had always been when I was her student. We chatted about little things for a few moments. She looked back at her desk fleetingly as though she had to work but didn't want to say anything.

"Well, I guess I should head back to my store," I said, I had kept it closed longer than my sign had indicated already anyway, "Say. Would you like to get dinner tonight? I am starving and I hate eating in restaurants by myself. My treat." It sounded a bit weird, but I was banking on her being polite. She was more than that, she seemed excited.

"Oh yes! That sounds great. I have to finish grading these papers, would you like to meet at the restaurant in two hours?" she asked. We agreed on a place and I went home to take a shower and get changed. Two hours later I was at her favorite Italian restaurant wearing my favorite dress. I sat down at the table and she arrived a few minutes later.

"Thanks for waiting. I am sorry, I decided to go home and get changed," she said and she looked fabulous. She was wearing a tight black dress. Conservative, but showing her curves, "I just love that a former student wants to talk to me. You know the best thing about being a teacher is knowing that you are impacting someone's life," she explained and I nodded.