Dana's Side Ch. 02

"Tutoring session with Jack?" she asked.

"Yeah," I said.

"How's it going?" she asked.

"Great," I responded. "He really is a good tutor and I think I'm getting it."

"And the rest?" she asked.

"Really good, too. He's great in bed, which you know, and I like him."

Ariel looked at me. "What are you saying?" she asked.

"I don't know. I'm comfortable with him. I enjoy being with him," I said.

"Then what do you think is going to happen with you two?"

"I don't know," I responded. "He and I are so different. We have different friends, and he is so smart, I worry that he will get bored with me—outside of the bedroom, of course, and eventually that won't be enough."

Ariel thought before responding. "If you are hesitating because you are afraid that dating Jack will hurt your social status, they you are really being silly. Not only is it dumb in general, but high school is over for you. You don't need to protect your precious status. And if you are worried about him getting bored with you, then it is up to you to make sure doesn't happen. But if it does, it does, and what have you lost if you guys spend a bunch of time together before it happens?"

Ariel made some good points, but I wasn't ready to try to commit, if I expected to be hurt at the end.

"You are right about the first part," I said, "but the second, I don't know. It's still early, and my gut tells me to try to keep it casual now, not try for anything exclusive, and see what happens."

Ariel responded, "I think you are making a mistake, but taking it slower may not be a bad idea."

"By the way," I said, "Jack thinks that we should try to set up Mom with his father. Sarah thinks it's a good idea, too. What do you think?"

"Why not?" Ariel responded. "I mean, any excuse to get Mom out with a guy is O.K. with me, and Mr. Davis is a pretty good looking guy. I say, go for it." She got off the couch and went upstairs.

A little while later, Jack knocked at the door and I let him in. I gave him a friendly kiss hello, and we sat at the dining room table. I told him that Ariel liked the idea of setting up our parents, and he texted Sarah. We started studying, and I could tell that Jack was impressed with where I was. I wasn't getting everything right, not by a mile, but I was definitely doing well enough that I could see that passing was more likely than not. Jack was incredibly encouraging, and explained where I was having trouble.

I also noticed that he kept stealing looks at my unbound tits as they moved under my shirt, and my face, which I appreciated. At the end of a little more than two hours, I started to lose focus, so we stopped. I could tell that Jack was eager to get naked, but it was Friday, and I saw no reason to rush. Mom was working late on some project at work, so I thought it might be fun to just hang out with Jack before getting to the sex, which I was also looking forward to.

So, after we closed the books, I said, "It's Friday, you know,"

"Meaning what?" he asked.

"Meaning that most normal people don't study late on Friday."

"Are you going out?" Jack asked, looking a little concerned.

"No, not tonight," I responded, "How about we do something?"

Jack looked a little confused by the situation, and said "O.K., so what do you want to do?"

"Let's have a beer and chill," I suggested. I got us a couple of beers and we sat on the couch, drinking and watching TV.

I had dated and had sex with a bunch of guys, but only a few times did I have any sort of relationship that lasted long enough for me to be comfortable with the guy, and just hang out. Usually, it was some sort of intense courtship thing, followed by a few days or weeks of sex, then a breakup. But those few longer relationships, lasting months, instead of weeks, were great. Somehow, after knowing Jack for only a few days, I felt that level of comfort. What I didn't know, though, was whether I really felt a real emotional connection with him, or whether it was just the fact that we had great sex and that he was nice to me. And, of course, I couldn't tell if he was just in this for the sex, or the fact that he was being talked about at school.

We sat, quietly, watching TV, and I turned to Jack and said, "Thanks so much for everything. I really feel like I'm going to pass this thing. And I actually am starting to enjoy it."

"No problem," he said smiling, "I've enjoyed it, too."

I could see that Jack was about to say something, and was struggling with whether to say it. Finally, he blurted out, "What is going on with us? I enjoy spending time with you. You must know I am incredibly attracted to you, and the sex is amazing."

I guessed that we were going to have to talk about this before I really wanted to. I looked at Jack and realized that he really was a good guy.

"You deserve better than me," I said, softly.

"Are you kidding?" he responded. "You're perfect."

I appreciated that he believed that, but I didn't think I really was perfect for him. I shook my head and he drank his beer.

"Look," I said, "you are so smart, so interesting, and you deserve a girl who can keep up with your mind, and give you the physical things you want, too. I can't do all of that that and you know it."

"No, that's not true at all," he said, emphatically.

Again, I appreciated that, and smiled. I guess I had to say this, but it was going to be hard, so I took a drink, and said, "someday, and it could be soon, or not, you are going to find that girl. And maybe I will find a guy who is the one for me, but, I have to admit that I enjoy your company, and, yes, the sex is amazing."

Now, it was his turn to smile at me, but he looked concerned.

"So?" he asked.

I needed to make it appear that I wanted an open relationship, and if it worked out for us, then it was meant to be. I took another swig of beer and said, "So, here's my thinking—we can still hang out, be friends and, yeah, screw as much as we want, but it isn't an exclusive thing. And if either of us needs to end it to be with someone else, it ends, with no hard feelings. What do you think?"

He didn't need to think very long, and said "That works for me. Kind of a friend with benefits deal, right?"

"Exactly," I said.

Why wouldn't he agree? He would still get to sleep with me, but could still see other people, including possibly my sister. But I wasn't going to make it easy for him.

"And how about we explore some of those benefits now," I said in my most seductive voice, leaning over to kiss him

He eagerly kissed me back and we made out on the couch for a while. I could see that he was getting aroused, and I bent down and kissed his cock through his shorts. I realized that I wanted it inside me, so I led him up the stairs to my bedroom.

In fact, I wanted to be naked with him, and quickly took off my clothing, as he did the same. I loved the way he looked at me, like he was seeing a beautiful work of art, and it turned me on. But I wanted to savor this. We got into the bed, facing each other and just kissed for a while, stroking each other gently. Jack pressed his cock against me and rubbed my back and butt, and I rubbed him, too. It was very nice, and I was getting aroused.

I lifted my top leg, and reached down, grabbed his big hard cock and slid it into me. I wrapped my leg around his thigh, pulling him close, so that his cock was deep inside of me, and my chest pressed against his. We stayed like this, not moving, and I loved the way he filled me up. I rested my head against him and closed my eyes, just enjoying the feeling of his body next to and in me. After a while, Jack began to slowly, agonizingly slowly, pull his cock out, then slowly push it back in. I rocked my hips in time with his slow thrusting, and felt chills all over my body.

Keeping his rigid member inside me, Jack rolled me onto my back. I bent my knees and arched my back, lifting my hips, as Jack moved to his knees. I thanked my cheerleading coach for the abdominal exercises that she made me do, allowing me to remain in this position which allowed Jack to enter me deeply.

He began to thrust harder and faster, and I moved my hips in time. Then, when I thought I was feeling as good as possible, he began to rub my clit, and my body began to shake. He kept rubbing and thrusting until he came, and I yelled out with pleasure from my orgasm and dropped flat on the bed. Jack landed on top of me, and he buried his face in my neck. He rolled off and held me close, saying nothing, just breathing. I didn't want it to end, but I knew that Mom would be home soon, so we cleaned off and got dressed.

We went downstairs, opened a couple of beers and started to watch a movie. I was happy and I sat there, watching, leaning against Jack's surprisingly strong arm. Mom came home a few minutes later, and I was glad we had gotten out of bed before she came home. She had caught me a few times in the past, and it really wasn't a big deal, but I tried not to make it a regular thing. I kind of felt like it made her feel like she was being a bad mother.

Mom looked happy, and when she saw Jack, she said, "Funny that you are here, Jack, I just got off the phone with your father."

"Really," he replied, "why?"

"He called me up out of the blue and asked me out to dinner tomorrow night."

"That's great," Jack responded. "He's a good guy."

"Did you guys have anything to do with this?" Mom asked, although she probably knew the answer.

I responded, "Yeah. Jack and I have been spending time together lately, and we thought that the two of you would get along. Ariel and Sarah agreed, so here we are."

Mom smiled and said, "I guess a kick in the butt from your kids isn't a terrible thing. I said yes, by the way—so I won't be here for your party tomorrow. I hope you don't mind."

"You have fun, and don't worry about us, we'll be fine," I responded.

"I'll ask Ariel to stick around in case you need anything," Mom said, and went to her room.

I raised my beer to Jack and said, "Wouldn't it be funny," she started, if my mother and your father...." I realized where this was going, and decided not to go there. Instead, I cuddled with Jack while we watched the movie.

The door opened and we sat up. It was Ariel, dressed to impress, and looking like she had a couple too many.

"Good to see you two getting along," she said, a bit loudly.

I responded, "So, where have you been?"

"Out at the bars. They are filled with douchebags who think that buying one drink for a girl is a ticket into her pants. A couple of my friends found guys they liked, at least for tonight, but I'm not going to take that crap anymore. Any guy who wants me is going to have to treat me right. Like you, Jack."

Without waiting for a response, she turned and made her way unsteadily up the stairs in her heels.

There wasn't much to say, so Jack and I sat quietly, watching the movie until it ended. I wanted to plant another seed in Jack's brain, so when he got up to leave and said, "See you tomorrow," I gave him a pretty seductive look and said, "Just so you know, if I pass this test on Tuesday, I am really going to show you my appreciation. You won't know what hit you."

He looked a little stunned by that, so I kissed him good night and he left the house.

I went upstairs to talk to Ariel. She had taken off her makeup and was sitting in her room, in a night shirt, looking more like an athlete than a drinker. "What happened?" I asked.

"Nothing good," she responded. "Every cute guy I met acted like an asshole. One guy started pawing me, and I don't think he expected me to be strong enough to remove his hand and nearly break his wrist. Another guy seemed nice enough, and we started to talk. I thought it might work out, when he told me that he was looking for someone to do a threesome with his girlfriend. Meanwhile, Beth was just looking to get laid, and found some pumped up asshole and left, and Cara was just trying to get drunk. Sarah was with Dave, this guy she has been sort of seeing. Finally, I let this slightly older guy buy me a drink, and he actually offered me $200 for a blow job. I almost punched him in the nose, but decided I didn't need to spend the night dealing with cops."

"Jesus," I said. "I think that may be a night for the record books."

"What about you and Jack?" she asked.

"Actually, we had a little talk tonight," I started. "We agreed that we weren't going to have any kind of exclusive relationship."

Ariel looked at me and said, "Is that what you want?"

"It is, right now," I said, and I kind of believed it.

"Well, then," Ariel said, "then you won't mind if I visit Jack tomorrow?"

I had no choice but to say, "Of course not. Have fun."

I wasn't happy, but I knew that if I wanted to take this position, I had to be consistent. And after the night that Ariel had, how could I begrudge her some good sex with a nice guy?

I got up and went to bed. I was getting into bed, when my phone rang, and it was Lisa. She was crying. After I calmed her down, I asked, "What's the matter?"

"I broke up with Hank," she sobbed.

"What happened?" I asked.

"He hit me," she said.

"What?" I asked.

"Not hard, or anything, but it hurt."

"What happened?" I asked, getting angry myself.

"I saw him flirting with some girl at school, so I called him on it. He denied it, but I told him I saw it. He got defensive, and tried to make it about how I don't go down on him enough, which, by the way, I do—he's the one who won't go down on me, but it got a little heated and he whacked my shoulder. I told him that we were through, and to go fuck himself."

"Good," I said. "You can do better."

She cried a little longer, and I consoled her.

"What happens if he comes to the party tomorrow?" she asked.

"I don't want to have a problem trying to keep him away," I said.

"I understand," she said.

"So," I replied, "you need to look super cute, flirt with other guys and show him what he is missing."

"Great idea," she said. We chatted a little more and then ended the call.