Dana's Side Ch. 03

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Dana and Jack try to define their relationship.
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Part 3 of the 6 part series

Updated 09/22/2022
Created 06/21/2012
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Saturday

I spent Saturday morning studying physics, and then began to prepare for the party. Ariel was nice enough to buy some beer and other booze, and I got some chips and other snacks. We were veterans of the high school party, and it didn't take long for us to have everything set. Mom helped out a bit, and I could tell that she was nervous about her date with Mr. Davis. Ariel and I tried to calm her down, and we spent some time rooting through her closet, until we found an outfit that she looked great in, and wasn't too desperate looking.

After lunch, Ariel left, presumably to go to Jack's, and I forced myself to look happy for her. The house was mostly ready, and I was feeling a little pissed off at Ariel, so I decided to go to the gym. I called Lisa, and suggested that a workout would be good for her anger. She agreed to pick me up and work out with me. I put on my workout clothes, and waited until she came. I got into the car, and she started telling me about how pissed at Hank she was, and what she was going to wear to the party to make him crazy.

"All good ideas," I said.

"What's your problem?" Lisa asked.

"Me? I'm just nervous about physics," I lied.

"But isn't your tutor helping calm you down, in more ways than one?"

"He is, actually," and I laughed.

We got to the gym and had a good workout. I sweated and felt good. We went for a cup of coffee, and continued to discuss Hank's stupidity, and thinking of guys who would be at the party who might be good for Lisa.

At one point, she asked, maybe jokingly, "Should I try to get a shot at your buddy Jack? You seem to be enjoying him."

It took significant control for me to simply laugh, and say, like I had to Emily, that it would be awkward for us to be sleeping with the same guy, and she agreed. Instead, we identified a couple of guys who had graduated last year, who were invited, and who I actually knew from personal experience were pretty good in bed. Lisa and I left the coffee shop, and she dropped me off at home.

Mom was beginning to freak out about the date, and had started to drink, and I convinced her to calm down, and to slow down her drinking. Ariel wasn't home yet, and I started to imagine her and Jack together, which didn't help my mood all that much. I showered and laid out my clothes for the party. My plan was to play it cool with Jack, see what happened, and make sure that he was with me at the end of the night. All without making it obvious to everyone else at the party.

I continued to arrange things for the party, when Ariel came home. Her hair was wet, and she was smiling.

"Have fun?" I asked, trying to sound upbeat.

"Yeah," she said. "It is nice to know that all guys aren't assholes."

"I guess," I said, noncommittally.

"Everything under control here?" she asked, "because Mom wants me to stick around to make sure you are O.K."

"Yeah. It's all good right now."

"Great," she said, and went upstairs. I heard the shower go on and assumed that Ariel was showering. It was strange thinking that I was sharing Jack with Ariel, but I also knew that if and when I told her to back off, she would. And he did seem to make her happy. I thought about the fact that if my plans worked out, Jack would have screwed both me and Ariel in the same day, which was a little weird. But it didn't make me want to do it any less.

A little before 7, Mom came downstairs, looking great. She was nervous, but excited. Ariel was watching TV and I was straightening up when the doorbell rang. I opened it, and Mr. Davis was there.

He introduced himself, and when I told him I was Dana, he said, "Jack's friend, right?"

I smiled and said, "yes, he's been such a great help."

Mr. Davis said hello to Ariel, who spent time at his house with Sarah, then approached Mom, saying, "Linda, you look beautiful. Thanks for agreeing to do this."

He was tall, like Jack, but dark, more like Sarah. He was kind of handsome, and had a similar charming awkwardness as Jack. I hoped Mom would have fun with him.

Mom responded, "No, Mark, thanks for asking. Shall we go?"

He took her arm and led her out the door.

Ariel discussed how cute they were, and I got up to shower and dress. Ariel went to the bar area and poured herself a tequila and started drinking it as I went up the stairs. I guess she was going to get drunk while we partied. I showered and put on the tiny, sheer bra and panties that I had chosen, and a skin tight, short black dress, sheer black stockings and boots. I fixed my hair and did my makeup. I looked hot, and if Jack didn't want me, I was confident that I could find someone else. Of course, I knew most of the guys who were invited, and really wasn't interested. But that could change.

As we had arranged, Emily arrived a little early, and we went over how she was going to seduce Jack's friend Fred. I knew that in reality, it wouldn't take much, but I wanted Emily to make it look real, and make Fred feel good about it. I gave her a few flirting tips, and she helped me make the final preparations for the party.

We turned the music on, and people started to show up. I grabbed a beer, and Emily and I went out into the back yard. The crowd started growing, and my group of closest friends gathered around me to drink and talk. I kept scanning the crowd for Jack, but didn't see him. I was talking to Lisa, who did, in fact, look incredible, when I noticed that Jack had quietly joined the circle, with his soon to be lucky friend Fred, and that he had positioned Fred to stand next to Emily. I was impressed.

I saw that Jack had gotten a good haircut and was looking at me, and appreciating how I looked. Good, I thought. I said, coolly, "Hey, Jack, I'm happy you could make it." I leaned over to give him a quick kiss on the cheek, and whispered, "Play it cool, enjoy yourself, the night is young. And, by the way, I like the haircut."

I stood back up and saw that Emily and Fred were talking, their heads close, and Emily was touching Fred's arm. She was a quick study. After a few minutes, Emily guided Fred away to a bench and they kept talking. I turned to Lisa and encouraged her to mingle and make sure that Hank saw how cute she looked.

When I turned back to talk to Jack, he was gone, and I saw him heading back to the house, looking around for someone. I wondered if he was looking for Gina, his other friend, who I hadn't seen. It was nice that Jack wanted his friends to have fun, and I felt kind of bad that my friends and I had spent the last four years essentially pushing them down just because they were smart and shy. But that was done, and I think I had made amends with Jack, and was on the way to doing so for Fred, even though, I hoped, he would never know that I was involved. Gina, however, seemed like a tougher nut to crack. She really seemed to hate me and resent my friendship with Jack.

After a while, I found that my circle had changed, and it was mostly guys, hitting on me. I was enjoying flirting with them, and even met one guy, Jimmy, who was a friend of Maria's older brother Carlo, who seemed cool. I noticed Jack was coming out of the house, with a short girl who looked kind of cute. It took me a few minutes to realize that it was Gina, with a real hairstyle, some makeup and nice clothes. As they approached me, I could see that Jack was smiling. He caught my eye and nodded.

I could see him direct Gina to look where Emily and Fred were still sitting on the bench, talking, laughing, and touching. Gina and Jack returned to the house after a few minutes. Something about the two of them made me a little uneasy, but I was having fun. I took another drink from my beer and went back to flirting with Jimmy.

I decided that I needed to circulate, and I walked toward the house. I thought I saw Lisa making out with a college guy, and saw Hank and a bunch of his jock friends laughing and watching baseball on the TV. I couldn't believe that he had the balls to come to the party, and I hoped it would not lead to a scene with Lisa. I wanted my last high school party to be fun for everyone.

I saw Gina talking to Paul, a kind of goofy guy who I always thought was pretty nice, but I didn't see Jack anywhere. I was pleased that he wasn't hanging out with Gina. As I was standing in the dining area, I saw Emily and Fred, holding hands, walk through. Emily caught my eye and smiled. I smiled back, happy that they were going to do it. My feeling was that sex was fun, if done for the right reasons, and in the right way, and I hoped that it was good for them.

I poured myself a beer and went into the next room to make sure that there were enough snacks, and that nothing was being broken. When I came back, I saw, across the room, Jack speaking with a skinny, very pretty junior, Natalie Kim. She appeared from nowhere at the beginning of school, and was quickly recognized as one of the prettiest and smartest girls in her class. I had invited some of the prettier juniors to the party, mostly, but not only, the cheerleaders. I hadn't focused on the fact that Natalie was exactly the kind of girl that would be perfect for Jack, and watching them flirt, I felt the hair stand up on the back of my neck. I could see from her body language that she was interested, and I couldn't imagine that Jack wouldn't be. They were laughing and drinking.

I couldn't let that happen, but I also had no real claim on Jack. It had to be his choice, and I couldn't let him know that I was trying to sabotage him. So, I went over to them, and stood behind Jack before tapping him on the shoulder.

"Can I borrow you for a second?" I asked, "You don't mind, do you, Nat?"

"Of course not," Natalie responded, but I sensed a little edge to her voice.

She was either being polite to her hostess, or afraid of me, but I didn't care. I led Jack away from Natalie to a private spot.

"Natalie Kim," I said, appreciatively, "She'd be a good choice for you."

Jack looked confused and sort of nodded.

I continued, "She is smart and pretty." I then leaned up and kissed Jack hard on the lips, tasting beer, and quickly gave his cock a little pat. "I know what we said the other day, and it's obviously up to you, but if you play your cards right, there will be a lot more where that came from. If you are interested, don't leave the party early."

He told me that Fred had left with Emily (which I already knew, and which made us both smile) and he didn't have a ride home yet, although Natalie had offered him one.

I gave him a hot look and said, "You can go with her, if you want, or stick around and I'll take care of your ride." I turned and disappeared, leaving Jack to his thoughts. I believed that I had weighted the scale one way, but with guys and the chance to have a new girl, sometimes you never knew.

I found a spot where I could see Jack, but he couldn't see me, and I watched him blow Natalie off, but not until they exchanged phone numbers. I started to walk back outside, and saw Gina talking with, of all people, Hank. I thought about warning her, but figured that she was a big girl and I knew that she didn't take shit from anyone.

I spent the rest of the party getting a good buzz on, talking with my friends, trying to prevent Lisa from making a huge mistake by going home with a particular guy and generally enjoying myself. I noticed that Jack had planted himself on the couch and was watching a ball game and talking. It looked like he was settled in and wasn't going anywhere. I didn't see Gina or Hank, and hoped that didn't turn into a problem, but it wasn't my problem.

By about 2, the party was winding down, and I saw Jack begin to help clean up. Ariel staggered down the stairs, and she and I, along with the remaining guests, began to gather and throw away the garbage, gather the recyclables, put away food, and generally try to straighten up. We woke up the drunks and sent them home, broke up the couples, and convinced them to get their clothing back on. After a while, it was just Ariel, Jack and me, and we worked to make the house reasonably presentable.

"Have you seen Mom?" asked Ariel.

"No," I responded, and checked my phone.

"No text either."

Ariel and I ran upstairs to see if Mom had come in without us noticing, but her room was empty. We all stopped and briefly thought what that might mean, but really didn't want to really think about it.

Ariel decided to go to sleep and Jack and I were alone in the kitchen. I smiled at Jack and said, "I see you made your choice. I'm flattered—Natalie is really cute."

"Not like you," he said, and I smiled back at him.

"You're not half bad yourself," I responded, "Maybe you can have her another night, but tonight you are mine."

"What about my ride home?" Jack asked.

"No ride home for you. Stay here with me; I think it will be O.K.," I said.

Jack texted his father and then we went up to my room. Jack received a response to his text, and while he was reading it, I stripped out of my dress, leaving on only my tiny lingerie. Jack turned to face me and stood there, staring at me hungrily. Which was exactly the effect I was hoping to have. He pulled off his clothing and threw it on the floor, looking at me with lust in his eyes.

"I am glad you stayed for me, you deserve a reward," I stated, pushing him down so that he was sitting on the end of the bed, his beautiful cock hard and pointing up and out.

I slowly removed my bra and panties for his benefit, then got on my knees between his legs and lowered my mouth onto his throbbing cock. I put my hands around its root and began sucking it deeply into my mouth. I twisted my hands on the shaft as I bobbed my head back and forth, using my tongue to ratchet up the pressure. My hair was flying around as I sucked away in a frenzy. I was almost out of control, and eventually, I heard Jack yell that he was about to cum. I cupped his balls and gave a gentle squeeze as he blasted a huge load into my mouth. I choked from the volume, but forced it down, before smiling and licking my lips. The ability to give a man that amount of pleasure was a huge turn on for me.

We crawled onto the bed, and Jack repaid my frenzy by attacking my tits, licking and sucking and rubbing them until I was moaning with pleasure. He licked circles on my breasts and I was writhing and beginning to rub myself. Jack seemed to realize what I was doing, and reached down and began to rub my clit while still spending time stimulating my nipples.

I spread my legs wider, and Jack stuck two fingers into my wet pussy. I found myself raising my hips off of the bed to meet his thrusting. Jack crawled on top of me and slammed his cock deep inside of me. Amazingly, I came almost immediately, shaking and yelling, as Jack continued to fuck me like a man possessed. I was having one of the longest orgasms of my life, wave after wave of pleasure rolling though my body, and I was moaning and grunting when I felt Jack shoot another huge blast of cum into me, then collapse on top of me, his face resting on my neck. It was incredible, and I was still tingling all over.

Sunday

I was half asleep when I felt something lightly poking my butt. Once I remembered that Jack was in bed with me, I smiled, realizing that it was his cock. I pressed back against him, forcing more of his cock between my thighs. I felt the warmth of his chest against my back and just lay there, half sleeping, and feeling good.

Jack gently pressed further in, and I opened my eyes and looked at the clock on the night table. It was 5:37 a.m. and clearly Jack was interested in a little early morning sex, which I was not against.

I whispered to him, "Are you waking me up at this ridiculous hour to fuck again?"

He must have thought I was angry, because he stammered, "um, kind of, not really, uh, I guess."

I laughed and said, "Great idea," pressing my butt hard against his cock.

Jack reached over and started stroking my breasts while slowly pulling his hard member from my thighs. I lifted my leg and he slid his cock into my wet pussy from behind. This was not like last night's crazy screwing. Instead, it was tender, slow and gentle. We stayed like this, slowly moving in rhythm while he played with my tits until he came.

I think he realized that I didn't have an orgasm, so he reached down to start rubbing my clit. I appreciated his concern, but I honestly just wanted to lay there in his arms, so I pushed my hand away, saying, "it's O.K. I don't have to cum every time. I know that you aren't taking me for granted. That felt nice, and I'm glad you got off."

It was so comfortable laying there in his arms that I fell asleep until about 7, when I needed to go to the bathroom. I checked Mom's room, and it was empty, and I looked outside, and Mom's car wasn't there. I wondered if that meant that she had stayed over at Jack's with his dad. I went back to my room and told Jack, and he smiled, then looked like he realized the strangeness of the situation. We took a quick shower together, helping each other to clean the places that were either difficult or fun to clean, and got dressed.

We were drinking coffee when I saw that look on Jack's face like he wanted to ask me something but was afraid. I was pretty sure I knew what was coming.

He got his courage up and said, "Can I ask you something, and don't get mad."

"Sure," I responded.

"Um, yesterday, we had that talk about not being a couple and all," he started.

I smiled and interrupted, "and you want to know why I interfered with your attempt to get into Natalie's pants?"

"Well, yeah, I mean, I wasn't even sure about her," he continued.

"No, I could see you liked her, and I really hope you pursue her," I said, even though I meant exactly the opposite, but couldn't say what I meant.

"I don't understand," he replied, looking confused.

I looked at him and put on my best act, saying, "I meant what I said yesterday. We aren't a couple, and both of us are free to see whoever we want. But here's a dirty secret about me—I am competitive. I have always used my looks to get what I want. I admit that. And when you aren't with me, you should do what, and who, you want. But especially in my house, when you have a choice between me and someone else, I always want you to pick me. You passed that test, and, I think, made out better than you would have if you had kept after Natalie."

He nodded, and said, "So, what you are saying, is you are O.K. with me seeing other people, as long as I pick you when given the choice?"

"Exactly. I'm not proud of that, but that's the way I see it."

"I think I understand. I can live with that now," he said.

Good, I thought. You can play around a little, but at the end of the day, I want you with me. And I want you to figure that out yourself.

We kissed and Jack stood up to leave. At that point, Mom came through the front door, her hair wet and tied back, with no makeup and wearing an unfamiliar t-shirt and sweatpants with the logo of a fancy private college that, I guessed, was where Jack's father went. There was an awkward exchange of hellos and goodbyes as Jack left. It was pretty amusing, and although I didn't want to dwell on it, I was happy for Mom.

I spent the rest of the morning cleaning up the house, and when Ariel staggered out of bed, she helped a little. So did Mom, and when we asked her about her date, would only say, "Mark is a very nice guy, and we had a great time."

When I pressed her for more information, she just said, "I'm not going to ask you about why Jack was leaving here this morning, and you aren't going to ask me any more questions."

Based on that, I was pretty sure that they had slept together, but I only asked, "Will you be seeing him again?"

"I hope so," she responded.

Once the house was back in order, Mom actually went up to bed for a nap, further reinforcing my belief that she didn't sleep much the night before. I hoped, for her sake, that Mr. Davis was as good as his son.

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