Scarlett's Challenge

We chatted amiably throughout the rest of the evening. If found out that she had been married for six years at one point but was now divorced and living with another female teacher so that they could afford a townhouse. I also learned that she was trying to become a vice-principal as she was hoping that she could steer policy decisions at the school. She was all-consumed with her work and seemed like someone who didn't get out to have dinner with an adult friend nearly often enough. She was very inquisitive about my life and seemed to take some personal satisfaction from the fact that I appeared to be succeeding in life, which I thought was sweet.

Eventually, the meal ended and I paid for the meal and then looked over at Felicity, as I had been instructed to call her. "So would you like to go get some coffee?" I asked. I was desperate to keep this sort of date going, but she quickly put the kibosh on that.

"Oh I wish I could Scarlett, I really do, but I have to get back and prepare my lesson plan for tomorrow and I should really work on my new reading curriculum proposal for the school board," she explained as she stood up from the table. I stood up as well and she gave me a quick hug, thanked me and for looking her up and then headed for the door. I went home alone and depressed. It didn't look like this last Challenge was going to be completed.

The next day I was sitting at the cash register in my shop, reading the newspaper and watching some teenage boys rifling through some antique Playboys. I didn't make it a habit to carry pornography, but these magazines were from 1954 and were valuable collectors' items. I was making sure that they didn't tear any of the pages or, God forbid, take them into the bathroom.

I was just about to fall asleep at the register when the phone rang, "Hello, Byrne's Used Books," I answered.

"Hello...Scarlett?" the female voice on the phone asked.

"Yes this is Scarlett Byrne. How may I help you?"

"Oh Scarlett, this is Felicity. FelicityTapper."

"Oh hi Ms. Tapper. I mean Felicity. How're you? What can I do for you?"

"Well I got home from dinner last night and I just sort of threw my pocketbook onto the table and didn't think anything more about it. Well this morning when I was getting my things together for school I realized that I somehow grabbed your credit card last night after you paid. I guess I am just not used to another person paying for my meals. Anyway, I am really sorry. I was wondering where your store was located so I could drop this off with you this evening," she explained. I hadn't even realized it was missing.

"Oh don't worry about it," I explained, "You know what, I know you are busy. Why don't you let me drop by on my lunch hour and I will pick up the card from you. Does 1:30 work for you?"

"That is actually perfect. The kids will be in lunch and then P.E. from 1:00 to 2:30," she replied, "I mean if you don't mind. It really is no trouble for me to come by your store after work."

"No at all," I replied, "I will see you at 1:30."

"See you then. Sorry again," she said and then hung up. This was the absolute last chance to finish the Challenge before Kegan got back from her parents. I was going to have to play a little dirty to finish this thing.

At 1:15 I cleared out my store and put my 'at lunch' sign up and drove over to the elementary school. The butterflies were really flapping in my stomach and I was intensely nervous. I was more nervous than I had been for any of my other challenges, both because this was in many ways kinkier than my other missions and also because it was the least certain. Ms. Tapper had given me no indication that she was in any way shape or form attracted to anything, let alone me.

I arrived in her classroom at 1:30 and walked in the door. She was sitting at her desk again, still looking beautiful and I knew that, despite my nerves, I had what it took to do this.

"Thanks for coming over," she said, reaching into her desk and pulling out my credit card. She handed it to me, "I really am sorry."

"I'm sure," I said, in a slightly sarcastic voice. She looked a bit confused, "Don't act like that. You know what is going on. Last night, you kept staring at me during dinner and putting your hands on my hands. Then you steal my credit card so that you can see me again. What's next? Are you going to show up at my store? Why do you think I came over here?"

"Oh my goodness Scarlett. Are you joking," she said, sitting back in her chair and looking at me dumbfounded.

"I am not joking," I said.

"We both know that nothing like that is going on," she said, getting a bit angry now, showing me a little bit of fire, which I found very exciting.

"Maybe we both know that and maybe if they did an investigation they'd find out that I was making everything up and that you weren't coming on to a former student. But, in the meantime, I wonder what parents would say about a teacher who wants to fuck her students when they grow up? I wonder if the School Board could justify putting someone in a position such as vice principal while such an investigation was underway?" I said and I could see that she understood what I was getting at.

"What do you want?" she said in a whining, defeated voice, "I don't have any money and it's not like being vice-principal is going to get me anything that you want."

"You already have what I want," I explained. With that I opened up my purse and pulled out my strap-on. Her eyes got huge and she blushed.

"Oh no Scarlett," she begged, "please." As she begged me to stop and quickly pulled my t-shirt off and unhooked my bra and removed it as well. I slipped my skirt down onto the floor and revealed that I wasn't wearing any panties. I strapped the dildo on while I talked to her.

"I want you to strip and then bend over your desk," I demanded. She hesitated for a few second, "Now." With that she got out of her stupor and quietly began to disrobe. She unzipped her long skirt and let it fall onto the floor. She her tight pink sweater over her head and threw it on the heap. She removed a cute pair of white panties and her black bra. Her breasts were even bigger than I had thought, probably D-cups on her small, 5'5 120lbs frame. She had her eyes closed as she turned around and put her hands on her desk. She was being brave but I could tell she wanted to cry. I felt sort of terrible, but I promised myself I wouldn't stop. I justified it by saying that she would enjoy it and hoping that I wasn't lying.

I got down on my knees behind her. Her asshole was at my nose level and I blew on her ass just to watch her squirm a bit. Then I stuck out my tongue and started licking it. I lapped at it softly, letting my warn, wet tongue wash over her asshole. She was as still as a statute while I worked, but her body seemed more relaxed as though she liked it. I let my tongue become more rigid and I started to slowly worked my tongue into her asshole. She grunted as my tongue went an inch or two into her ass. Still she was quiet. After a few minutes of this, I was satisfied that her asshole was well lubricated. As I stood up I touched her pussy briefly with my hand. She was wet. I smiled to myself. It was working.

"When was the last time you got fucked Ms. Tapper?" I asked as I stood. I leaned over her and gave her a kiss on the back of the neck. Unconsciously, she arched her back and pressed into me. She didn't answer, "Come on. Don't be shy. I'd hate to not be done when the children come back," I said.

"Four years ago," she answered. I considered this to be a little bit sad. Luckily it was about to be remedied.

"When was the last time you got fucked in the ass," I asked as I positioned the plastic cock against the little bud of her asshole. Again she paused for a second, but this time she answered without further prompting.

"18 years ago," she said. I was sure she was being honest. I was a little surprised. I figured that she was going to say never. I wanted to know how it happened, but I decided to just go for it.

Slowly, I pushed the tip of the cock into her ass. She moaned in a high pitched voice, but worked hard to be quiet. I was proud of her. Slowly but surely, the cock slid deep and deeper into her ass. She was biting her tongue, but soon she was pushing back into me, driving the cock deeper into her ass. Suddenly, a breakthrough occurred.

"Oh God yes, baby," she said. She seemed a bit embarrassed that she said it, but it was undeniable. She was a little bit into it now. I put my hands on her hips and pulled her in. Suddenly, my hips were against hers and the entire cock was buried in her asshole. She started to bounce up and down a little bit, working the cock around inside of her. I slide the cock in and out of her ass and she breathed in deeply. I started fucking her ass in long, slow strokes. She took one of her hands and started to rub her breasts.

I continued on at a slow pace for quite a while. Fucking her slowly and softly. She started pushing her hips back and I decided to give her what she wanted. I started slamming the cock into her ass. At the same time, I ground her tits around from behind and rubbed her hard, pink nipples. I kissed the middle of her back while I fucked her. Suddenly, her body started to buck hard and I could tell she was having an orgasm. I kept fucking her hard and she had a very hard time staying quiet. Eventually her entire body went limp and she fell to her knees in front of the desk and the cock popped out of her ass.

For a second I let her sit on her knees and breath. Then I got back to business, "Turn around I need you to clean my dildo," I informed her. She turned around and looked at me.

"How?" she asked, genuinely unsure.

"Suck my dildo Ms. Tapper," I said. She remained business like now. Not indicating whether she loved it or loathed it, but she opened her mouth and took my dildo in her hand. She guided it to her lips and took it into her mouth. She seemed to enjoy her own flavor on it because soon she was sucking it for all it was worth.

"Finger me," I said and she didn't miss a beat. While she was sucking the dildo, she took her index finger and gently inserted it into my sopping wet pussy. I felt electricity shoot through my body. Carefully, she inserted another two fingers into my pussy while she continued to suck on the cock, licking her own asshole off of it.

I fell over in an intense orgasm. The entire idea was just so hot and her fingers were so knowing. I moaned loudly and fell to the floor on top of her. She put her hand over my mouth to keep me quiet but continued to work her fingers in my pussy until my orgasm finally subsided. We sat silently for a minute and then I quickly leaned forward and kissed her. I was surprised to find that she kissed back. We kissed more deeply. I started to gently rub her pussy with my hand, manipulating the soft folds of shaved pussy. She moaned into my mouth and again she came, this time very quickly. It was like a flood gate had been opened, the slightest touch of her clit sent her over the edge.

After a series of consecutive orgasms, Felicity went completely limp. I touched her gently but she did not respond. I began to grow a bit nervous. However, a few moments later she stirred and looked at me and smiled again for the first time since I first came into the room, "Thank you," she said.

"My pleasure," I said, kissing her, "you're very good." She blushed.

"I am really sorry," she said, "but the kids are going to be back soon or someone might walk by the door," she warned. I got the hint. Slowly we got dressed together.

"Thanks again Mrs. Tapper," I said.

"You know we can't have a relationship," she said looking serious and forlorn, "All the stuff you said before is true. It would be career suicide."

"I just wanted to fuck you," I said honestly and she giggled.

"Thanks for putting that gently," she said and kissed me again.

"Maybe we'll do it again sometime," I said.

"Don't hold your breath young lady," she said as I walked out the door. I looked back once briefly and she was already in her chair working as though absolutely nothing had happened. She was certainly a strange woman and unlike the other girls I had been with during the Challenge, I didn't feel like I knew her any better now than I did before we had sex.

It was surely the most bizarre little interlude in my Challenge, but as I walked out the front door with my credit card in my pocket, all I was thinking about was Kegan.

Chapter 7: The Reward

"Honey I am Home!" Kegan yelled two days later when she opened the door from the lower level of our building and into the upstairs apartment. I was sitting at the kitchen table drinking coffee and waiting for her. I knew that she was coming home that morning and I felt butterflies in my stomach as I waited.

"Kegan!" I yelled and stood up. She dropped her bags on the tile floor and ran and put her arms around me. I gave her a kiss and she kissed me back, deeply.

"How was your week," she asked as she sat down at the table and I got her a cup of coffee as well.

"Not bad," I replied, not wanting to get too far into it, "How're your parents?"

"They were fine," she said and I could tell she was hiding something as well. We sat silently for a few minutes. I took a deep breath and told her everything about my week and my experience with Ms. Tapper. She listened silently and didn't seem to respond at all. I was very nervous that maybe I had been wrong all along. Maybe she had really just made the bet to get me away from her or for her own bizarre entertainment and that she wasn't really interested in me. It didn't really sound like Kegan, but her silence was deafening.

"Scarlett, we need to talk," she said and sounded very nervous. She was looking into her coffee and refused to look up. My blood was running cold and my heart was in my stomach.

"Okay," I said and felt a bit dizzy.

"I didn't go home this weekend just to hang out with my parents. Like, it was part of the reason, but there was something else that I had to do," she said and then paused.

"Okay."

"I had to tell them something," she said and then looked up, "Scarlett I told my parents I was a lesbian this weekend. It was a little bit intense, but they are supporting me. I had to tell them that so that they wouldn't be surprised you know, at least I am hoping they would've been surprised if I hadn't done it," she said and I was confused.

"What?" I asked.

"Sorry," she said, "Listen, I wanted to ask you something. Scarlett, I want you to be my girlfriend." I was quiet for a minute. My heart was soaring. I was so happy I just didn't know how to express myself. I knew I was torturing her, but I was trying not to.

"Yes, oh my God yes!" I was finally able to stammer out. She looked into my eyes and it was a very magic moment. It felt so incredibly right. I leaned across the table and kissed her. She put her hand on my cheek and kissed back. We sat at the table for a long while, just kissing and holding one another.

"Would you like to got to bed?" she asked and all I did was nod. She took me by the hand and led me to the bedroom. I was in my pajamas at the time and she quickly pulled the shirt over my head. My breasts feel free and she kissed them gently, sucking on my nipples and holding me close.

"I love you," I said and she stopped. She looked into my eyes.

"I love you too," she said and then looked back down, her big blue eyes closing as she started sucking on my nipple again. She put her hands around my waist and pushed my pajama pants down. They fell in a heap on the floor and I kicked them off. She continued to kiss me the entire time.

She slowly pushed my down onto the bed and I spread my legs for her to fall in between them, but she let me fall on my own, laying on my back on the bed. I watched her as she slowly undressed for me. I had dreamed of this moment since the first time I saw her. She bent over me and kissed my bellybutton ring. As she stood she took the bottom of her polo shirt and lifted her arms over her head and threw the shirt on the floor. She danced for me, spinning and showing her body. While she danced, she unhooked her bra and slid it down her arms. She had the cutest little breasts with a teardrop shape and perky little nipples. She kicked off her flip flops and giggled when one hit me in the arm. I kept watching as she unzipped her jeans and slowly worked the tight denim down her legs. She slipped them off carefully and continued her dance. I saw that she was wearing a lacy thong and her ass was very cute, tight and firm. Finally she slipped the thong off as well. Her pussy was very small and looked incredibly tight. I saw that she had a small landing strip of public hair and I wanted to kiss her pussy.

She stood naked in front of me for the first time and I was stunned by how good she looked. Even in my wildest dreams I never thought a girl who looked like Kegan would ever be in front of me. She was like an actress or a supermodel. She slinked herself over towards me, walking in a carefree and seductive way. My legs were still apart and she dropped her body between them. Our breasts were touching and I wrapped my legs around her. She kissed me and I kissed back. We lay like that for a very long time, just kissing and holding onto one another.

After a few minutes of this she moved her body up and put her nipple against my mouth. I opened it up and took her nipple in. I sucked gently on her and swirled my tongue around on it. She arched her back into me and she squeaked a sexy little noise.

"I've never had that done before," she said.

"Liar," I said around her nipple.

"No seriously," she said, pulling her nipple from my mouth and looking at me with her baby blue eyes, "I have never wanted to be with anyone in my entire life. You are my first," she explained. I pulled in for a big hug and held her close.

"I have an idea," I said and she raised her eyebrows. I pulled her over and spread my legs wide, I gently pulled her legs around until we were scissored into each other's legs. We inched our bodies together until, in the most magical moment of my entire life, our pussies touched. We gently rubbed them together at a slow rate and while we did this I watched her play with her tits. I did the same. She was a loud lover, which I greatly enjoyed. She moaned and groaned while we played.

Slowly I pulled myself out from between her legs. I quickly swung myself around put my face between her legs. She started playing with my hair. I breathed in deeply. She smelled unbelievable. She was musty and sweet in just the right way and when I finally tasted her I couldn't believe how delicious she was. I lapped at her for a long time, tasted her tiny pink clit and nibbled on her pink labia. Slowly, I inserted one finger into her pussy. She was incredibly tight and she moaned and squirmed but begged me to keep going. I started licking her clit more intently.

Suddenly, she leaned over my back. While I continued to lick and finger her pussy, I felt her fingers touch my pussy from behind. I grunted into her pussy and licked her more quickly. She stroked my pussy gently, never actually entering it, but rubbing it softly and then putting her fingers into her mouth. She started to rub my little asshole as well. I was surprised by this but I shook my ass into it. I kept licking her while she worked her index finger into my asshole. I started fucking her pussy faster and licking her harder. She, in turn, started to really fuck my ass. After a few seconds of this pace, she came hard. Her pussy squirted hard on me and I tried to drink it all in but it was too much. She fell back on the bed and kept humping her hips into my face and finger until she finally relaxed and laid down. We sat for a while and just breathed.