Scarlett's Challenge

"Okay," she said in a voice barely above a whisper, but she still just stood there next to the bed in her sexy underwear looking at me. I was going to have to guide her.

"Okay Meredith," I said, taking my finger out of my pussy, "I want you to sit down on this bed and pit your feet against my feet facing me." She climbed up onto the bed and put her bare feet against the bottoms of mine, they felt a bit cold like she was nervous.

"The door is open," she said, pointing to the bedroom door which stood a few inches ajar.

"I'll worry about that," I replied and then I took my finger and started rubbing my clit gently again, "Okay Meredith. I want you take you panties and pull them to the side so I can see your pussy," I said. She did as she was told and I saw her shaved pussy with its pink little lips and a large, hard little clit.

"Like this?" She asked in a sweet, innocent way and I nodded at her.

"Okay now. I want you to take your finger and get it nice and wet with your pussy," she did that, "Okay now take the pad of that finger and rub it gently on your little clitoris. Believe me; once you get started you will know what feels good." She started to circle her clitoris and she was letting out little yelps of pleasure. She looked so cute, bent over watching her finger move over her pussy and seeming to enjoy it.

"Oh God Scarlett, this is so wrong," she said and I make a shushing noise and told her to keep going.

"No I want you to take that finger and just nice and easy slide it into your pussy," I told her and slowly she complied, "No don't stop playing with your clit. You can use the other hand if you have to," I said. She did this and I started playing with myself again. I had never done any mutual masturbation, but I found that I enjoyed it. It was so sexy to see someone fucking themselves and it was equally sexy to know that they were seeing the same thing. These sorts of thoughts were rushing through my mind when suddenly my pussy started to tingle and I could hear myself starting to moan. I was fucking my pussy very hard with my finger when the orgasm came. Meredith stopped altogether to watch me. My pussy squeezed tight on my finger and slowly my orgasm subsided.

"That was really pretty," Meredith told me and I smiled. I got up on my hands and knees and crawled over to her.

"Have you really never played with yourself before Meredith," I asked as I put my hand against her pussy lips. She shivered and then smiled at me.

"Oh come on Scarlett. That was fun don't ruin it," she said and I knew the answer. She was pretty good at playing innocent, I had to admit that. I leaned forward and kissed her on lips while I stroked her pussy with the back of my hand. She squirmed a little bit but surrendered completely to the kiss. She put her hands on my shoulder and I leaned farther in, sucking her tongue into my mouth and nibbling on it. She seemed to really enjoy this so I did it more. Suddenly, she started to squirm and then she put her hands on my shoulder and pushed me away.

"Oh God," She said and her eyes looked hurt, "I am sorry Scarlett. This is wrong. I've known you since you were a girl. Your mother and I are good friends. I am married! My kids are downstairs." As she spoke she became more and more hysterical. She tried to get up from the bed, but I grabbed both of her wrists and held her close.

"Meredith," I said and she looked into my eyes, "Relax. I don't want you to run away with me and leave your family and I don't want you to tell my mom about it. I want you to fuck me just one time." She paused for a second and looked at me.

"Just once?" she asked after a long pause. I giggled and then leaned forward and started kissing me again. Once again, I gently stroked her soft pussy lips with the back of my hand, getting it wet with her juices.

"You still want me to fuck you?" I asked. Now it was her turn to giggle. She paused for a long while. She was fighting something, but I knew I was going to win.

"Please," she said and wrapped her arms around me. I had an idea. I put my arms around Meredith and pulled her over onto the bed and rolled her around so that her head was on the pillow. I kissed her again and cupped my hand over her pussy. I then pulled down her bra so that her breasts were exposed and gently began to suck on them. She moaned writhed on the bed and I could feel her pussy dripping onto my hands.

I broke contact with her and she lay on the bed, looking at me with desire. I stood up and turned around and then I lay down on top over her in the 69 position. I found myself face to face with her pussy. I breathed her in but before I could start to lick her, she attacked my pussy. She was licking me hard and grabbed my waist and pulled me in.

"Oh my God Scarlett, this tastes so good!" she said and I smiled. I always love compliments you know. Now I began to repay the favor, gently licking her pussy in contrast to her hard reaming of my pussy. She was incredibly horny at this point. She stopped licking me and started grinding her pussy into my face. I sucked on her clit while she moaned and bucked. Suddenly there was a crash from downstairs.

"You boys be quiet! I am trying to help out Ms. Byrne. If you can't be good then I am going to make you stay at Grandma's tonight when Daddy and I go out!" she yelled at her children. I hadn't stopped sucking her pussy the whole time. Lucky for us the door had been opened.

I took this opportunity to plunge my finger deep into her pussy and she came instantly. I rode her body as she arched her back and screamed. She started licking my pussy again and the entire situation was so hot that I started cumming again, grinding my shaved pussy into my mother's best friend's face. Eventually our orgasms subsided and I collapsed on top of her for a few moments.

After a long time, I caught my breath and rolled over. I crawled on my hands and knees and lay down next to Meredith while she panted on the bed.

"How was that?" I asked her and then gave her a kiss on the cheek.

"That was wonderful Scarlett," She said and turned kissed me on the lips.

"Happy anniversary," I said and she started to laugh. However, this seemed to remind her of the situation we were in and she sat up and then went back to the bathroom to get changed back into her regular clothes. I too got dressed and then sat down on the bed and waited for her to come out.

She walked out still putting earrings back into her ear, suddenly a mother and a wife again and no longer looking like a stripper. I missed the hot stripper. She was all business now too, "Scarlett, I had fun with you this afternoon but I can't ever do this again," she said, suddenly blushing. It was like she had been drunk with lust and was waking up the next morning and realizing the mess she had gotten herself into.

"That's fine," I replied.

"You aren't going to tell your mother are you?" she asked and I laughed loudly.

"No Mrs. Hoke. I got you covered," I said. With that she led me downstairs and to the front door. She told me to feel free to come by anytime and have dinner with her and her husband. It was cute to see her embarrassments and attempts to deal with her actions.

"Thanks for the memories Mrs. Hoke," I said to her as I started to turn to walk back to my car. She put her hand on my shoulder and turned me around. She looked around conspiratorially and then gave me a quick peck on the cheek.

"You too Scarlett," she said and then gave me a quick wink before quickly walking back into her house and closing the door.

Chapter 4: A Friend

"I don't think that counts," Kegan said, plopping down on the couch in our apartment. I sat down next to her and clicked the movie on.

"Oh come on, it was hard enough getting her into bed. I wasn't going to ask her to do anything kinky," I said.

"Well I understand that, but this is going to count against you," she said.

"Come on, her kids were just downstairs and I had sex with her on her husbands bed on her anniversary. She called down to her kids and yelled at them while I was eating her out!" I said. I felt like I had an ironclad argument that I deserved some points for the kinkiness of my actions.

"Oh wait! She yelled at them while you guys were together?" Kegan asked.

"Yeah. I told you that before," I replied.

"Well I didn't hear that," She replied, "It counts."

"That's what I thought," I said and I gave her a kiss. She kissed back and as I leaned over and pushed her down onto the bed the popcorn fell onto the floor. She laughed and then pushed me back up into a sitting position.

"Hey there Scarlett," she said, "You still have three more missions to go before you get paid. Come on, let's watch the movie." I shrugged and then put my arms around her and watched the movie. We went to bed in our separate rooms again that night. She was really starting to drive me crazy. Even as I was fucking other girls, I found that it made me just want her more and more. I felt like we were getting closer as well. She really liked hearing my stories when I came back from a conquest. She was going out less with her friends for movie nights and we even went on a sort of date to the French restaurant that Mrs. Hoke was going to with her husband. I was starting to think that I loved her and that she loved me too. That's why it broke my heart to go my separate ways with her each night. The next day I got a phone call that cheered me up quite a bit. It was a call from my friend Connie Winters.

"Hey Scarlett, how're you!" she said in an excited voice. I was happy to hear from her too.

"Hey Connie, not too bad. How about you, how was the honeymoon?" I asked, trying to be a good sport. We had been best friends since we were little girls, but I hadn't been invited to the wedding. She didn't even have any sisters. I should've been the maid of honor! But I wasn't going to get all bent out of shape about it. I knew it wasn't her decision.

"Oh it was wonderful. I really love the beach!" she said. I knew for a fact that they had gone to a beach in Delaware. For their honeymoon.

"Well great! Your mom told me the ceremony was very nice," I said. At the firehouse.

"Yeah it was. Hey I am sorry that you weren't invited. You know I really wanted you to be there but Todd was afraid that it might be a little awkward if you were there," she explained.

"Why?" I asked, knowing the answer but still not really believing it.

"Well you know, you guys date for a while." she explained, obviously feeling uncomfortable.

"Yes, we did go out three times in high school before I came out," I said. Todd was a dickhead then and he was a dickhead now. Connie had only married him because she had strenuously believed that it was wrong to have sex before marriage. She was 23 years old and wanted to have sex. So now she was married to Todd. Her last name wasn't even really Winters anymore. It was Schlictman. I decided to drop it.

"So do you want to come over and see picture and stuff?" she asked. It was really the last thing on earth I wanted to do, to look at pictures of Todd. However, I had figured I could work on something else so I agreed. I grabbed my big purse and headed for the door.

I arrived at the Schlictman abode, a tiny little cottage with four rooms, a few minutes later. Connie was sitting on the front stoop waiting for me. She looked beautiful. She was a short girl just like me; she was 5'3 and weighed about 105lbs. She had short blonde hair in a pageboy cut. She had big blue eyes and a funny shaped nose that was cute on her but wouldn't work with anyone else. She had a long, elegant neck and small, perky breasts. She was very slim and had long, thin legs. Her skin was very fair and despite the fact that she had just spent a honeymoon at the beach, was neither tanned nor burned. She was wearing a white wife beater tank-top with no bra and a pair of boxer shorts; she was wearing flip flops as well.

She ran up to me and threw her arms around my shoulder and gave me a huge hug. I could feel her breasts against me and I could feel my body tingle. Despite the fact that Connie was gorgeous and had been forever, I had never before consciously considered having sex with her. She was the homecoming queen in high school and the social butterfly, I was a year ahead of her in school, but she was always the cool one and had probably been the reason I had finally made it off of the JV cheerleading squad my junior year. She had always taken care of me. Maybe that was why I was still angry about her wedding.

Anyway, I just hadn't ever thought of her like that. Maybe it was because she was a bit of an airhead. But now I felt the heat from her body against mine and I found myself deeply attracted to her. I could smell her perfume and feel her soft body and I wanted her. But I had to move slowly.

"Oh you look great," I said, speaking honestly as our hug broke.

"Thanks! So do you," she said and I had to admit, I felt like I looked good today, with my favorite little skirt and a white polo shirt on.

"Come on in, look at my new house," she said. And indicated towards the front door with her hand. I followed her as she opened the door. I tried to act excited, but the house was a little wreck. It was in worse shape than my little apartment and at least as small. The living room barely had enough room for a couch and a TV and the kitchen had only a microwave with no real oven. The bedroom was completely filled by the queen sized bed and the wallpaper was peeling. The bathroom had a weird smell that I decided to associate with Todd and the floor was very sticky. I could tell she had tried hard to fix the house up to impress me so I acted impressed. She made some instant coffee and we settled in on the couch.

"So how is your store doing?" she asked. I think the idea of being a housewife was unsavory for Connie, but that is what Todd wanted. She was always wondering how my business was doing. Oddly enough, she probably had a better mind for business than I did. She was also always interested in my love life, but I just pretended like nothing new had occurred.

"So tell me about the honeymoon!" I said finally, I kind of wanted the details about it.

"Oh it was really, really nice. Todd's dad has this little condo near the beach in Delaware and we just went up there and stayed."

"Was it on the beach?"

"No, it was only like two blocks away though," she replied. I think that she honestly had liked it, so I decided not to get on her about it too much.

"So...you waited all this time," I said finally getting obvious for her, "how was the sex?"

"Oh my God Scarlett!" she said and then laughed. She was a bit of a prude and always had been. Not just about having sex, but discussing it as well.

"Come on, I tell you about all of my sexual adventures."

"Yeah against my will," she replied giggling. I just stared at her intently. Eventually she sighed and rolled her eyes, "Fine if you must know. We had sex three times." She said it as though that were the extent of the information that was necessary.

"Three times in a week?" I asked and she nodded naively. I was laughing on the inside, but on the outside I was trying to be positive to protect my friend.

"Well the first night we had sex and then the next night Todd had a little too much to drink..." She droned on, giving excuses for his poor stamina and inability.

"How was it? How big is he? How long did you guys go for?" I said, shifting gears towards performance. Connie was blushing and sipping her disgusting instant coffee. I felt sad. Connie was a very sweet girl and she surely deserved a good deal more than this.

"It was really nice," she said unsurely. She hesitated for a bit. But she knew me, she knew I would press her until she answered the other questions, so she just blurted them out, "He is a little small I guess. Like 3" I guess. He didn't last too long either, probably like two minutes or so. But he says that he will get better with practice." I felt even worse for her now. These were her first sexual experience? Does that even count?

"Oh," I said. If you can't say anything nice and all that.

"It really was nice though Scar," she said and I nodded, "I know you don't like Todd but I love him and I wish you would just get over it!" She was suddenly angry and I was a bit taken by surprise.

"Hey back off, I didn't say anything," I replied, "Besides, I have every reason to be angry. We are best friends. I have known you since you were in second grade. I think I have the right to be angry. Hell, I have the obligation to dislike him at this point. And you know what? It wouldn't have been awkward if I had been at your wedding. We went out on two dates when we were freshman. He fucking whipped his dick out in his dad's car at the drive-in and I made him take me home. It was at the very moment that I saw that little penis that I realized that I was gay. That's why he doesn't like me, because I saw his complete lack of manhood in every sense of that word. I should've been there because I love you." By this time, Connie was crying. I felt terrible, but everything I had said needed to be said. I put my arm around her and she cried for a while.

"That wasn't the reason he didn't want you there," she said and I was a bit surprised.

"What do you mean?" I said. "I said that wasn't why he didn't want you there. It was my fault," she explained. I was entirely confused at this point.

"Hon, you need to explain this to me a little bit better because that doesn't make any sense."

"He told me about that night at the drive-in a long time ago. I wasn't upset about it and I don't think that he is embarrassed about it anymore or anything," she said. I figured that he still should be, but I kept listening to her, "It was just, well...One night we were talking about stuff. Todd and I. So he was talking about how he thinks that lesbians are hot."

"Gross," I said. Usually, I don't mind if guys think two girls together is hot. I tend to agree with them. But not Todd.

"Anyway. He made me tell him what girl I would be with if I was going to be with any girl. Anyway, I couldn't think of anyone because I am not gay. But I said you. I said you because I care about you and it's true. If I had to be with a girl I would be with you because I love you," she said. I was dumbstruck. There was something so incredibly sweet about Connie and I couldn't believe how flattered I felt, "But anyway, he thought that there was more to it than that because you are a lesbian. I think he was afraid that I was like unconsciously into you or something and he didn't want you to be at the wedding. But you see, it was my fault. I should've just said a celebrity or something and then he wouldn't have worried about it."

"Connie, listen I am sorry," I said and put my arms around her in a big hug. We hugged for a while. When we broke the hug I addressed her in a serious voice, "I want you to know three things. First, I am not mad at you for not inviting me. I never ever blamed you and I was never angry at you. Second, it wasn't your fault, Todd was being a dick. He really shouldn't have held what you said against you and he certainly shouldn't have held it against me. Third, Connie I love you and I want to be your best friend forever, so I won't ever let Todd get in between us, okay?" She was crying again, but I think it was because she was happy this. Time, eventually, she got herself under control and she gave me another big hug.

"Thanks Scarlett," she said and I waved it off. We generally didn't have a lot of emotional moments between us and we both felt a little bit uncomfortable. I decided to break the ice.

"So his dick is still tiny?" I asked and she took the opportunity to laugh.

"Yeah I guess so," she said, "I couldn't even tell when it was in." That sent me into a gale of giggles. I was rolling around on the floor and Connie was begging me to be nice. I apologized after I was able to get myself under control.