Dana's Side Ch. 06

Tuesday

I woke up with dim light filtering through the curtains and a bad case of cotton mouth. As my haze lifted, I realized that I was asleep, lying on my side between Jack's legs, with my head resting on his thigh. It looked like Jack's head was on Ariel's belly, as if we had fallen asleep in the middle of something. I began to remember some of the previous night's activities, but after the double blow job, it all was just a mass of sex and skin. It must have been good, because as I thought about it I started to feel a little tingly, and felt myself start to get wet.

I lay there, not moving, and I saw Jack's cock begin to stiffen. I wasn't sure if he was awake and getting horny again, or if it was just a reflex during sleep, but I didn't really care. I reached out and gently directed his cock into my mouth, softly sucking and licking it without any urgency, just enjoying the feel of it getting harder and bigger in my mouth. Jack must have been awake, and he began to run his fingers through my hair, and his fingers kept getting caught in knots and tangles. I could see that Jack was also gently caressing Ariel's pussy. Where last night was insane, this was quiet and relaxed, but it felt good and, considering the fact that I was naked in bed with my sister, surprisingly comfortable. Jack's cock began to twitch, but I wanted my pussy to have some fun, so I took his cock out of my mouth, got up and lowered myself onto his rod, and just sat there, as he continued to finger Ariel.

I started to bounce up and down on his cock, speeding up as my arousal increased, while Jack was fingering Ariel with one hand, making her squirm, and rubbing my tits with his other hand. Jack came inside me at the same time that he brought Ariel to a moaning orgasm. I stopped bouncing and felt his cock go soft, but he wasn't finished—he used his hand to massage my clit until I began to wiggle my hips and came, laughing. I fell on top of Jack, resting my head on his chest and fell asleep.

When I woke up, I was still lying on Jack, but Ariel was sitting on Jack's face, facing me, grinding her pussy into his face. There was a look of incredible pleasure on her beautiful face, and I was struck at how much I loved her. I lifted myself off of Jack and turned around so that I was straddling Jack, my knees on the bed, with my butt facing Ariel, I began to lick his hard cock like a Popsicle, and I could feel him moaning, even if his mouth was muffled by Ariel's crotch. I lifted my ass up in the air, and Ariel bent over and began to lick my pussy from behind. Her oral sex skills were incredible, and I was soon shaking with pleasure, which caused me to increase the intensity of my stimulation of Jack's cock. He blasted yet another load of cum into my mouth at the same time as I heard Ariel scream out and I felt the wave of another orgasm roll over me, making me laugh hysterically, again. Ariel fell on top of me, causing me to collapse onto Jack

The three of us lay there, panting, as we recovered. Eventually, Ariel rolled off of me, and I climbed off of Jack. The room was a disaster area. The bed was a mess—the sheets were pulled off, crumpled and stained, there were pillows all over the place and the blanket was jammed under the bed. I looked at Jack and Ariel, both naked, trying to process the whole thing. I certainly didn't feel embarrassed, yet there was a certain exhilarating taboo to it. Jack broke the uncomfortable silence saying, tentatively, "Well...that was fun..."

"Holy crap," Ariel said, "that was incredible, and Dana, wow..."

Jack asked us, "Had you ever done anything like that with each other before?"

I looked at him and said, "No, but I'm not unhappy that it did now."

Ariel smiled and said, "I agree, but we need to keep this between us, O.K.?"

We all agreed. This was a special night that I would always remember, but never expected to repeat.

I went into the shower, and although I wouldn't have minded if Jack came to join me, or Ariel for that matter, I was kind of glad that they didn't so I could have a little space. Jack followed me in, and when he was done, Ariel showered. We dressed, stripped the bed, found what looked like cum stains on the carpet and cleaned them before heading downstairs. Steve and Sarah were already at the dining room table and gave us huge, knowing smiles when the three of us came downstairs together.

Before anyone else spoke, Ariel looked at Sarah and said, pleasantly but firmly, "What you think happened, happened. We keep this among ourselves, like the other stuff, right?"

Sarah agreed, and Steve pointed out he didn't know what the "other stuff" was, and neither did I, but they agreed anyway. We ate breakfast and needed to clean up and get on the road, because Ariel and I had to work that night.

Ariel and I gathered laundry and ran the washer and dryer while Jack cleaned up outside with Steve and Sarah packed up the kitchen and straightened up the common areas. We finished by putting all of the bedrooms back into order, loaded up the car and drove home. Even though he gave up some leg room, Jack offered to sit in the back between me and Ariel, and we both rested our heads on his shoulders and slept much of the way home.

We got home and only had a few minutes to chat with Mom before Ariel and I had to change and go to the restaurant.

When I got there, Tanya looked at me and said, "I think I know what you have been doing all weekend, and with who."

I smiled and said, "You are right, I'm feeling pretty good right now."

"I'm glad," she said, as I went out on the floor for my shift.

Wednesday

I knew that I needed to resolve my situation with Jack, and wasn't surprised when he called me and asked to get together. I was surprised that he picked the park. Clearly, he wanted a public place, one where we could still have some privacy, but where we wouldn't be able to avoid our issues by just having sex. What I wanted was to end "friends with benefits" and move into an exclusive relationship. I was confident that if I asked him, he would agree, but was that what he really wanted? Not to mention, if I asked him, would it mean that I had lost control of the relationship? But did that really matter anymore? I was usually in charge in my prior relationships. I decided whether or not to sleep with them. I used my assets to lead almost every guy I ever dated around, and that included Jack, at least at the start. Now, I was uncomfortable with being the one asking for him to decide to choose me. My goal was to get him to ask, but if he wanted to keep things the way they were, I would agree. And, as with Gina, I was willing to wait, because at the end of the day, I knew I was really the best choice.

I knew that if I came on too hard, it would be too obvious, and but I wanted him to know that I valued our relationship and thought about it. I found the not particularly flattering clothing I wore during our first tutoring session, and put them on, hoping that he would notice. I kept my makeup and hair simple and went out to the park. I arrived a couple of minutes late, and was surprised to see that Jack wasn't there yet. In the past, he was always right on time. I wondered if he was trying to play with my head, but I didn't think that was the way he did things. I sat on our agreed upon bench and waited.

His lateness was beginning to worry me, when I saw his car pull into the parking lot. I saw him approach, and shivered, despite the heat. I noticed that his stride was more confident than it was back before his first weekend at the lake house. When he got closer, I smiled at him, and stood up. I could see him look me over and smile, I hoped it was because he recognized my outfit. I hugged him and gave him a gentle kiss on the lips. He looked at me with real affection, which was a good sign, and we sat down on the bench, facing each other.

Before I could say anything, he just started talking, the words rushing from his mouth, "Dana, I wanted to talk to you, because I am confused. On the one hand, you act like you want to be my girlfriend, exclusively, but on the other hand, you push me away. You tell me about other girls, you agree with Ariel to share me over the weekend. You even seemed to agree with me over the weekend that we should continue as friends with benefits, but other times, I sense that you don't want that, at all."

I looked at him, confused. When did I say that I agreed that we should continue as friends with benefits? Did I say something to make him think that? I wasn't sure what to do, so I thought I could make him commit.

"What do you want?" I asked.

He didn't say what I hoped, instead responding, "What I want, is for you to be straight with me. For example, you once told me that you thought that Natalie was a better fit for me than you, and you know how my first date with her went. Do you still think that, because if you do, I think I should ask her out again."

Fuck, I thought to myself. Why did I ever say that? Fuck Fuck Fuck. What could I say, without looking like a needy idiot? Natalie was a real threat, but I knew there was some issue that got between them before, so I didn't think she was so formidable. And if he struck out again, I knew he would come back to me, unless I acted like a bitch now.

I gritted my teeth and said, "I guess that if you want to go out with Natalie, then you should." I took a deep breath, smiled at him, and said, trying to recover some degree of dignity, saying, "I hope you understand that I also have guys I want to date, and if your attempts to sleep with Natalie fail, I might not be there when you want me."

I could see a brief flicker of doubt cross his face before he said, "I understand, and I want us to stay friends," he said.

"With benefits," I replied, flashing him a look that I hoped would remind him of what he was risking. We kissed, briefly and went home separately.

This was, surely, not how I wanted this to go, and I had a nagging feeling that I had been manipulated by Jack, which was uncomfortable, but a little exciting. Of course, one of the things that I liked about him was that he didn't play games, but I also respected the fact that he was growing confident enough not to just give in to me.

Epilogue

Over the next couple of weeks, Jack went out with Natalie a few times, and my sources told me that they seemed to be enjoying themselves. I didn't really want to see anyone else, so I threw myself into as many waitressing shifts as I could get. Tanya was worried for me, but I told her that I would be fine.

I had heard from Lisa, who had heard from one of Natalie's friends, that she and Jack decided to stop seeing each other, so I wasn't surprised when Jack called me. Considering the fact that I hadn't been laid since the lake house, I was extremely horny, and was about to invite myself to his house for some rebound sex, but before I could, he asked me out to dinner that night. I realized, strangely, that it would be our first real public date. I poured myself into a tight black mini dress with the skimpiest of lingerie, and I could tell that Jack appreciated how I looked. He actually wore a sport jacket.

We went to The Tuscan Villa, and had an incredible meal. But even better than the food was the conversation. I realized how little we really knew about each other, and we talked about our hopes for the future. Jack told me about how miserable he was for most of high school, and I discussed how badly I felt for the way I lorded it over everyone. We left the restaurant, and I loved the way Jack lightly placed his hand on the small of my back as we walked out. I was looking forward to fucking his brains out, but when we got to my house, he walked me to the door, kissed me goodnight and left.

My body was buzzing with desire, but I realized what he was doing. He wanted to go through the process of getting to know each other better before we would have sex again. To make sure that our relationship was based on friendship, not just lust. I realized with a laugh that he was, knowingly or not, turning my old game of making him anticipate sex to increase his desire back on me. It was working.

The next morning, Jack called, and invited me to the movies. I got someone to cover my shift that night, and agreed. At the theatre, Jack went to get popcorn, and I saw him get on a longer line rather than the one that was being served by a kind of slutty looking girl with big tits who I recognized as an underclassman at North. I wondered if she was the cause of his fight with Gina, and if so, silently thanked her. We saw a French comedy that I never would have picked on my own, but which turned out to be both funny and poignant. Jack held my hand during the movie, and I rested my head on his shoulder. After, we drove to my house and talked and made out in the car for a while. I went to give him a blow job, but he surprised me when he stopped me, and he again walked me to my door and refused to come inside. I was dying, and thought about pulling out my vibrator, but figured I could wait for one more date, which would be the third, which was, traditionally, when sex often happened.

When I came home from work the next day, there was a bouquet of flowers waiting for me, with a note from Jack, saying, "I have really enjoyed getting to know you the last few days and am looking forward to our third date." Mom and Ariel wanted to know what was going on, and I explained as best I could. He called me later that night, and invited me to his house the next night, for dinner. I wore a flattering, but not particularly revealing outfit, but wore the bustier, corset and panties I had used for the "appreciation" evening underneath as a surprise, if we got that far. Jack cooked me a delicious chicken stir fry for dinner, and we talked about how we felt about each other. Eventually, we went to Jack's room, where he appreciated my surprise, and we had truly incredible sex that somehow felt more meaningful than any we had before.

The rest of the summer was unbelievable. If I wasn't working, I was with Jack. We did everything and anything together, from going to museums to shopping to just watching TV. The sex was incredible, and we ended up sleeping over at each other's houses regularly. Mom and Mark didn't give us a hard time, because they were doing the same thing. I was as happy as I ever remembered being. I considered Jack to be my closest friend, and we reveled in each other in and out of bed. Tanya joked that she needed to tie weights to my legs to keep me on the ground.

As we got closer to the time to leave for college, it got difficult. Jack and I were so close but we also knew that it wasn't realistic for us to keep things the same when we went away. Our colleges were far enough apart to make it hard to maintain a long distance relationship, and we were both comfortable enough with each other to acknowledge that we had very healthy sexual appetites. So, after long discussions, some tears, and lots of sex, we agreed that when we went to college, we were each free to see other people, but that we would try to remain friends, and if appropriate, enjoy the benefits. I know that I was confident that Jack and I would remain friends, but recognized the risk that he would find someone else who would click with him on every level. And I believed the same was possible for me. But I also was happy to know that we could still see each other, too. If at some point, we were in a position to get back together full time, and we both wanted to, that would be great, too. Our last night before I left for cheerleading practice was awesome, and we both cried when Jack left my house.

College turned out to be everything I had hoped, and more. It was great having Sarah there; she had become like another older sister to me. She helped guide me through the transition, taking me under her wing and giving me great advice. I joined her sorority and ultimately became its president.

One day, during my freshman year, I found out that some pictures of me in my cheerleading uniform were getting posted to the Internet, and were gaining some popularity. After that, I occasionally saw other candid shots of me, at sporting events, at parties, or even just walking around campus, on the web and started to get a little annoyed, until I was approached by a local modeling agency. I figured, if people liked looking at me and pictures of me, I might as well get paid for it. I did a little swimsuit and catalog modeling, and made appearances at trade shows and store openings. I had to quit cheerleading my last year to have time to do this, while keeping up my studies and my sorority duties, but it paid for my last year of college, and even let me build up some savings. I was offered a fairly large sum of money from a magazine to pose nude, and after a little soul searching, I declined. I didn't want nude pictures to surface some time later when, I hoped, to have a real job, or a family.

I worked my ass off in my classes, determined not to be thought of as a dumb cheerleader, and received a degree, cum laude, with a double major in communications and marketing. My social life was active, and my sexual needs were rarely unmet. Jack and I continued to hook up during college, and we even visited each other when we were in relationships, as friends. Nevertheless, I never found anyone in college who meant as much to me as Jack did.

During Christmas break of my senior year, I got a call from Sarah, who was visiting her father and Jack. We met at the coffee shop and she told me that she was working in Washington, D.C. with a big party planning firm, and wanted to hire me as her assistant when I graduated. It sounded like a good opportunity, and I accepted. After graduation, I moved to Washington, got a small apartment and worked for Sarah. I took to the job, and was rapidly promoted and had my own assistant, who I also hired from State. Sarah opened her own firm, Lake House Promotions, and I went with her. She generously gave me 5% of the firm at the start, and I ultimately became the chief operating officer, with 25% equity in the firm. Jack was also a part owner, and we all did very well when the firm went public.

As always, my social life was active. I dated many well known and powerful men, politicians, businessmen, actors and athletes. I had a strict policy of never dating married men, because I saw how cheating screwed up my mother's life for so long. Although Mom dated Mark for a while, ultimately they broke up, but she remarried shortly after and is happy. Most of my relationships were, unfortunately, short term, although there were a few that lasted for over a year. Jack and I still found time to get together when we were between relationships, and we talked often, about life, and people, and even about our relationships with other people. We had one memorable week at Lake House's company villa in St. Bart's where neither of us wore clothing for most of the week and only got out of bed to use the bathroom. I still wonder what the kitchen and house staff thought about that, and the noises that came from the bedroom, but they were paid well to keep quiet.

I never felt the same about anyone as I did about Jack, and held out hope that someday we might find ourselves in the position to be together. But I was in Washington, and he was pursuing his Ph.D. in physics and teaching jobs in schools that always seemed to be in the Midwest. I knew that he would be an incredible professor. One day, he called me and told me he had met Rebecca, who he described as a brilliant physicist and almost as beautiful as me. They had met at a physics symposium and he told me he knew from the moment they met that he wanted to marry her.

They married shortly thereafter. Sarah and I planned the wedding for them, as our joint gift. Before the wedding, I had a brief conversation with Rebecca in which she made it clear that she understood that Jack and I had strong feelings for each other, and that she trusted both of us would not act on those feelings. I made it clear to her that I had no intention of doing anything to interfere with their happiness. I was one of Jack's "groomsmen", along with Mark, Fred, Steve, and a professor friend of Jack's named Rakesh, and attended the wedding with my then-boyfriend, a baseball player who I had started dating right before the wedding. Ariel came with her fiancé, Robert.