Scarlett's Challenge

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YKN4949
YKN4949
5,864 Followers

"Fuck me! Fuck me Scarlett!" She screamed at me as she placed a hand on the back of my head. I started to rub deeper, harder and I kept my pace licking her sweet little pussy. She began to squeal and push my face harder into her pussy. I felt like I was hanging on for my life. Suddenly, her entire body became stiff and she shook all over. Her pussy clenched tight over and over again on my finger and then she went limp on the bed. She was panting now and I sat up in front of her.

"How was that Cinid?" I asked and she quickly sat up, despite her panting, and kissed me deeply on the mouth, licking her own pussy off of my face. She was almost crying now.

"Oh my God Scarlett. That was amazing. Thank you so so much. That was so hot," she said and was laughing. She was also absent mindedly rubbing my nipple and driving me crazy. I groaned and kissed her again.

"Want to pay me back?" I asked and she nodded vehemently, "You have to promise to do just this one thing that I ask okay? You have to pay me back?"

"Okay," she said a bit warily, but relaxed when I smiled, "What do you want baby?" I didn't respond directly. Instead I just lay down on the pillow. I spread my legs and then bent them back and hooked them under my elbows so that my pussy was straight up in the air.

"Lick my little asshole while you finger me," I said. She looked stunned. I wanted her to do this for two reasons. The first was that in order to complete the challenge I had to convince the girl I was fucking to do something nasty. The second, and more important reason, was that I loved when girl's played with my asshole. I loved to get my asshole eaten out.

"Really?" she asked and looked at me out of the corner of her eye. I nodded and for a second she looked uncomfortable but then she seemed to warm to the idea. She leaned forward and kissed my pussy once. It was an amazing feeling and I almost changed my mind and asked her to eat me out. But the thought of Kegan kept my mind focused.

She paused for a second and then her tongue touched my asshole and my entire body was on fire. My ass was wet from my pussy and she started lapping the juice out of it. "Finger fuck me too baby," I said while I groaned. She put her middle finger against my pussy and rubbed my clit gently. Next she slowly started to slide it into my pussy. She really knew what she was doing in this case; most girls tended to know how to finger a pussy. I was more surprised by how well she took to ass licking. Soon she had lapped up all of the pussy juice and I could feel her warm tongue gently blanketing my asshole. Then she stuck her tongue out rigid and slowly started to insert it into my asshole. She worked her tongue into my ass at the same pace that her finger worked into my pussy. I grabbed her pigtails with my hands and worked her tongue deeper and deeper into my asshole.

Soon I was completely out of control. I was rubbing my asshole against her tongue and humping her finger hard. She was groaning and I was shrieking. Suddenly my entire body felt warm and my pussy and asshole tingled. My body trembled and I humped harder than ever. Suddenly my orgasm went to an entirely different level. I was shaking and yanking on Cindi's pig tales and then I collapsed on the bed, panting. Cindi slid up my body and planted her lips on mine. I kissed her deeply and tasted my asshole and pussy on her. She was giggling as I wrapped my legs around her. We kissed for a while, she really seemed to enjoy it. She fell asleep with my body wrapped around her's and I fell asleep to the rhythm of her heartbeat.

Chapter 3: Mother's Friend

When I got back to the house the next day I immediately told Kegan. To say the least she was shocked. I gave Cindi's panties as proof which she thought was sufficiently gross but she believed me.

"Well did you do something nasty? That's part of the challenge too?" she explained and I told her about the cheerleader burying her tongue in my asshole. She seemed to accept this as nasty enough although she couldn't believe that I really had enjoyed it. I was doing well so far.

"So what happened after you guys woke up," she asked. I laughed a little.

"She was really happy because she had stayed out all night and hopefully scared the shit out of her mom. So I drove her home. She seemed to be in a good mood. Anyway we got to her house and she gave me a kiss and said that maybe we could see each other again. But she assured me she didn't think that she was a lesbian and that she didn't want to date or anything. It was really hard to not act really relieved by that you know. I was terrified I was going to have this cheerleader following me around. Don't get me wrong, she is really hot, but I don't think I am in the mood for that kind of aggravation," I explained. While I had been talking Kegan had gotten on her computer.

"Damn," she said.

"What?" I asked. She turned the computer around and showed it to me. Cindi was on the screen wearing her cheerleading uniform and smiling.

"You weren't kidding," she said.

"Where'd you get that?"

"It was on the school website," she explained, "Well you got one down now, only four almost impossible missions to go." With that she gave a long, sensuous kiss and I felt my knees get weak. I had thought for a few minutes while I was with Cindi the night before that maybe there were other beautiful girls out there for me. But now, with Kegan kissing me hard on the lips with her hand on my waist, I knew that anyone else would be a mere distraction. I wanted now to quickly get to my next girl. Like Kegan had said, one down four to go.

I made a conscious decision about my next mission. The next person I would go after would be my mom's old friend Meredith Hoke. I hadn't seen her in years. Not since my mother had kicked me out of the house. Not that I hadn't been back home at all during that time, it's just I tended to not stay for very long before my mom kicked me out again. I remember Mrs. Hoke being incredibly beautiful and I found it surprising that someone as beautiful and sweet as Mrs. Hoke would want to spend any time at all with my mother. But that is the way things seem to work. Mrs. Hoke was sweet but demure. My mother was a bitch but she was assertive. As a result of this dichotomy, my mother ended up controlling Mrs. Hoke most of the time.

I had decided to go after Mrs. Hoke next because I knew that my mother was going to be out of town for the week and that her house would be empty. It helped with my plan that my mother wasn't there and it also decreased the odds of my mother getting in my way at some point.

It was the Saturday after my experience with Cindi that I went over to my mother's house. I went over in mid-afternoon. This was a time I figured that Mr. Hoke would likely be at work and that Mrs. Hoke would be sitting around the house, waiting for someone to come over and snatch her up. I pulled my car up into the driveway and got out. I tried my best not to look over at the Hoke's house. I walked up to my mom's door and knocked. I stood there, knowing that no one was going to come to the door.

My heart almost jumped out of my throat when in fact the door did open. Standing in the doorway was Mrs. Hoke.

"Mrs. Hoke?" I exclaimed and almost fell over. She was taken aback a little as well.

"Oh my God!" she said in a pleasant voice, "Scarlett I haven't seen you in ages!" Mrs. Hoke was more beautiful than I remembered. It seemed as though having kids and aging to 43 had caused her to take better care of herself. She had medium length brown hair and brown eyes like before and a kind, delicate face. She didn't look like a mother but instead like a news anchor, older to the point of being distinguished but still sexy. She was tall and elegant, 5'8 and probably around 120lbs. Her breasts were larger, probably as a result of growing older and having children, but they still seemed firm and young. Her legs were graceful looking and she had a beautiful smile on her face. I was immediately glad that Mrs. Hoke had somehow made it on my list.

"I know," I said and threw my arms around her in a big hug, "What're you doing here?"

"Oh your mother wanted me to get the mail while she was out of town," she explained, bending over and picking up the letters on the floor next to the mail slot and giving me a pretty nice view of her cleavage.

"She's out of town?" I said, in mock disappointment.

"Oh yes," she said, "she didn't tell you?" I shook my head. I was breaking Kegan's rule about lying, but in this instance I felt it was necessary.

"Well. Never mind then, I suppose. It was nice seeing you again," I said and then turned and started walking to my car. She ran down next to me and stopped me.

"Hey, why don't you come over to my house and have a cup of coffee or something, no sense in leaving right away. You just got here," she said, putting her hand on my shoulder to get me to stop.

"Oh no, I don't want to impose," I said, but everything was working according to plan up to this point, better than according to plan actually.

"Believe me, you would not be imposing. It will be nice to have the company of someone who is over the age of 8 for a change. Come on over," she said and moved her head towards her house. I smiled and shrugged my shoulders.

"What the heck," I said and she nodded her head and smiled. We walked across my mother's lawn and then across Mrs. Hoke's lawn and climbed up her stairs, "I really appreciate this Mrs. Hoke, it's very nice of you to let me come in."

"Nonsense. Listen to me, I have known you since you were twelve years old. We are old friends. If you can't count on your old friends then who can you count on? Oh, one more thing. Don't call me Mrs. Hoke. You're an adult now. I would appreciate it if you call me Meredith," She said as she opened the door to the sound of little boys running around and making a general racket.

"Sure thing, Meredith," I said, feeling awkward in actually saying it but feeling better. I couldn't imagine moaning out "Mrs. Hoke." This dirty thought made smile and pussy tingled a little bit. I had to control myself. I had to remain cool if I wanted to get this done. There might only be this once chance.

Meredith and two sons, one was 8 and the other was 6. They were cute little boys and it seemed that they spent most of the day running around, knocking things over, and causing their mother to have a massive headache. She seemed genuinely relieved to have an adult to talk with. She fixed us something to drink and we sat in the kitchen and sipped them slowly and spoke a little. She seemed not to notice anything that the children were doing, but occasionally she would yell something and they would quiet down for a moment or so.

She asked me about my job and I asked her how the children were doing. She seemed completely burned out with the kids. I gathered that they were her kids. She had wanted them and she had given birth to them. Her husband seemed to be little more than a sperm donor who came home every night for a free dinner and a place to watch TV.

"So why haven't I seen you in years?" she asked, trying to change the subject away from herself. I noticed now that she was a bit haggard. Not in her skin or in her hair, she was meticulously put together and incredibly beautiful. Her eyes, on the other hand, looked worn out and I actually started to feel bad for her. I decided to lay some of my troubles on her. Maybe they would make her feel better about herself.

"My mom didn't tell you?" I asked.

"No," she said, shaking her head and then leaning back in her chair. She had her legs crossed and she was absent mindedly smoking a cigarette.

"She kicked me out right after high school," I said bluntly. Her eyebrows raised and she leaned forward. She was my mother's close friend, but as in any situation, she always wanted the really good dirt on all of her closest friends.

"No! She hadn't told me. What was it about?" she asked. Leaning forward conspiratorially.

"Well. I guess it was the night I graduated. I came home that night and I was just in the world's best mood you know. I had done something that no one in my family had ever done before. So I decided to tell my mom off about all the stuff she said I would never do and be honest with her. She had said she wasn't going to go to my graduation because she was busy, but when I got home she was sitting in the living room watching TV," I explained and she nodded her head.

"So what happened?"

"Well I sat down and I told her all of the things that she said about me that were lies. Like when she told me that I was too stupid to graduate or called me a whore and said I'd get pregnant before I turned 18. Then, when it was all finished I told her that I was a lesbian," I explained. Meredith simply froze for a few seconds.

"Well..."she said and then paused again for a few seconds. She leaned in even closer, "Was that true?"

"Well yeah I mean I wasn't too stupid to graduate and I didn't get pregnant," I said. She laughed a little and this seemed to relax her.

"No. The other thing," she said, then briefly turned to yell at the boys to keep it down.

"Yeah it's true," I said and she looked at me for a few seconds. I could tell she was thinking something along the lines of 'but she is so pretty' or 'but she is so feminine.' But I was sort of used to this reaction from people a bit older than myself and didn't take any offense or anything.

"Do you have a...partner?"

"Nope. Kind of a small town here, hard to find other girls with similar... interests," I explained and again she laughed, a little more openly this time.

"Well, don't tell your mother I said anything, but I think that it is absolutely rotten of her. You can choose to do whatever you want to do. You are and were an adult," she said. This was actually pretty sweet of her. I had never heard her actually say anything negative about my mother in all the years I knew her, let alone come out and say my mother was wrong about something specific.

"Thanks," I replied. I decided that there was nothing more on this vein so I decided to change tacks, "So how is your husband?"

"Oh he is fine," she said completely reflexively, "It's actually our anniversary tonight."

"Oh that's exciting!" I said and then considered what this meant for my chances and decided to ignore it and press on.

"What are you guys going to do?" I asked.

"Oh well, Jim usually gets home around 6, so I have a sitter coming over at that point to watch the boys. We are going to go downtown and get something to eat at that new French place and then we are going to see a movie," she said and made it sound like the most exciting thing in the world. Sounded like the most unimaginative date in the history of mankind to me, but that was just me.

"Sounds like fun. I have been to that restaurant. It is very good. It's only a couple of blocks from my store," I explained and she seemed very proud of herself. She put out her cigarette and once again yelled at the boys to be quiet, "What did you get him?"

"Oh well..." she said and I realized I had hit something fun, "Can we talk about something?"

"Sure," I replied and knew for a fact that it was going to be good.

"Since the boys were born, my husband and I...we haven't been intimate as much as we had been in the past. I thought at first it was because I was a little out of shape from the pregnancy so I started a little home gym in the basement. I think I have gotten myself back into shape," she said.

"You look great!" I said, cutting her off. She blushed a little bit and then pressed on.

"Well that didn't help anything. So I have been trying to think of other things that I could do. So I decided this year for my anniversary present I would buy my husband a special present. I got some....lingerie. I bought some really sexy lingerie and I am going to wear it tonight and see if I can, I don't, jumpstart the thing. I don't know if it is going to work, I don't even know if I look good in it," she explained.

"I am sure you look great," I said, laying it on thick, but sensing that she liked it that way.

"Oh I don't know. I this that maybe it isn't as flattering for my tummy as it could be," she explained and looked down at her toned stomach and rubbed it through her sweater.

"Go put it on," I said, "I can tell you how it looks. " "Oh no. I don't know if I can do that," she said, shaking her head and taking a nervous sip from her coffee.

"Hey, Meredith. Think about who you are talking to here. I think I would know better than most women how good you look in lingerie. If you know what I mean," I said and winked at her. She relaxed a little and laughed at my joke and I knew she was going to do it.

"Alright!" she said and stood up, she was almost giddy now, "I am actually really excited that I can show it to someone." She beckoned me to stand up and follow her and I did as she said. She yelled something at the children and we walked up the stairs to her bedroom. Her house was generally a mess, as you would imagine a house with two little boys would be, but her room was something different altogether. It was a large, clean, and happy little oasis. Meredith pointed towards the bed and I sat down and smoothed out my skirt. She walked over to the nightstand next to her bed and took out a small package.

"I'll be right back," she said, taking the package and walking into the bathroom. I scooted back on the bed until my shoulders were resting against the headrest. I crossed my legs in front of me and waited for Meredith to return. She was obviously excited because she was back out just a couple of minutes later and she looked absolutely perfect.

Her hair was tied back behind her in a little bun, she was wearing a bra that was just a little bit to small for her large breasts. The bra itself was bright pink on the bottom and pulled her breasts apart. There was black lace on the top of the cups of the bra. The shoulder straps were thin and black but the other straps were pink as well. She was wearing a pink thong from what I could tell and over top of this was a pink and black garter belt. The garter belt was connected to tight black fishnet stockings and she had long, black gloves that came up to her elbows. I could hardly breathe while I looked at her. She spun around once and smiled at me. I couldn't believe how tight her ass was when she spun around.

"What do you think? What does my stomach look like?" She asked, staring at me intently.

"Perfect," I said and I meant it. I decided to go for it now. I uncrossed my legs and spread them apart. While I did this I flipped my little tartan skirt up and revealed that I was wearing no panties. My pussy was already wet with excitement and I started to gently rub my clit with my fingers. Meredith stopped moving and stared at me intently, her eyes glued to my hairless pussy. While she was mesmerized, I reached up and removed my t-shirt. I quickly unhooked my black bra as well and laid it down on her bed next to my shirt. I returned on hand to my dripping pussy and the other one I used to gently tweak my nipples. I moaned a little bit. This seemed to pull Meredith out of her stupor.

"My God Scarlett!," she said, "What the Hell are you doing?"

"Don't you ever masturbate Meredith?" I asked and giggled at her. With that I plunged my middle finger into my pussy and kept rubbing my clit with my thumb. I was clawing at my breasts now and my entire body pulsated in a gentle motion.

"Why are you doing that?" she said and actually pointed at my pussy.

"Oh God! Meredith you are so sexy," I said and I could tell that she was fighting not to act flattered, "Come here baby. I can teach you how to do this. You are so sexy. You don't need someone else to appreciate that to have fun. Come on, I'll show you how to do this and anytime you want to feel sexy you can just do it by yourself." She looked at me for a few seconds and I kept fucking my pussy harder. I couldn't believe how much fun it was to have someone watching me. Finally she acted.

YKN4949
YKN4949
5,864 Followers
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