Dana’s Side Ch. 02
Mar 14, 2023 // By:analsex // No Comment
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Feeling good on Wednesday morning, I dressed to my usual standards of hotness, and went off to school. I shocked Mr. Stone by actually answering a question in physics, and was heading off to lunch when I realized that I was walking by Jack’s locker. I went over to him, put my hand on his shoulder and whispered into his ear that I had mentioned to a few of my friends about our post-tutoring session, and I hoped that it would help to make up for the fact that I had been part of the reason that he had been socially excluded.
As I left, I said, so that everyone could hear, “Tomorrow at 5, my house, right?”
“Yeah, see you then,” he responded.
I figured that would definitely get tongues wagging.
At lunch, I could see that Jack and his friend Gina were fighting, and she stormed out of the cafeteria. I wondered if it had anything to do with me, because it seemed like Gina was particularly pissed off at me. But she really didn’t matter to me. Instead, I spent the lunch period answering questions from my friends about Jack. They were curious, and I was only complimentary.
Emily was quiet during the whole discussion, and it struck me that I could probably convince Jack to deflower Emily. I didn’t think it would take much convincing because she was cute, and because he would sympathize with her. And based on the day before, I was pretty sure that he would treat her well, and make her first time a good experience.
After lunch, I called Emily over to speak with her privately and told her my thoughts. After hearing me praise Jack, she was eager, but wanted to be sure that it was O.K. with me.
“No problem,” I said.
“I don’t own him, and he doesn’t own me.”
We agreed that she would come to my tutoring session the next day on the pretext that she needed some help, and afterwards, I would talk to Jack about it. They could use my room while I studied. Emily seemed excited as we went to class.
After my shift at Orlando’s, I came home, showered and got back to studying physics. I worked on the second chapter, and after I understood it, I did the questions. I realized that it wasn’t so hard, I just needed someone to explain it to me properly.
I watched some TV, then went on to Facebook. I accepted Jack’s friend request, and checked out his profile. There wasn’t much on it; he had a bunch of friends from other schools, mostly nerdy looking guys and unattractive girls with bad skin and unflattering haircuts and clothing, some family members, including Sarah, as well as Ariel, Cara and Beth. There were some pictures of him with his two friends, some at what looked like science fairs and academic competitions and a few of him and his father touring colleges. I noticed that his father was pretty good looking for an older guy.
About 8:30, I got a text from Maria saying, “I’m at the movies. That guy Jack you were raving about is here with some girl. Redhead. From South, I think.”
“Thanks, good for him,” I texted back.
Information like this was important, even though I had no real relationship with Jack. But now that he was on my radar screen, I needed to know how the date went. I went into Ariel’s room and told her that Jack was on a date with a girl from South. She went online and Facebook messaged Sarah, who confirmed it.
I studied a little more, watched some TV and went to bed.
I woke up Thursday and checked my email and Facebook. There was an email from Ariel, from late the prior night.
“Jack’s date went nowhere. He came home pretty early, but believe it or not, Cara texted him for a booty call, and he went there. Haven’t heard from Cara.”
Wow, I thought, Jack is really getting around. It surprised me that I cared so much, after just one time with him, but I guess I felt good for him. He was such a scrawny little nerd for so long, he had lots of lost time to make up for. And, if all went well, he would be making up a good piece of it that night.
Nothing of great interest happened at school, although I noticed that Jack’s friend Gina ate at a different table, sitting with a group of kids that actually were below her in the pecking order, which was pretty remarkable. On the other hand, I noticed that Jack was getting more attention from the girls at school and even high five’s from the guys. It felt good to know that simply the rumor that someone had slept with me was still enough to raise their status. I was curiously looking forward to tutoring and fucking Jack later that night.
Emily came over to my house at about 4:30, and we discussed how we were going to arrange this. She was nervous, and even showed me her underwear, which was plain, but still sexy, and I assured him that Jack would love it. She asked me for some pointers, but all I could say was, enjoy yourself, don’t do anything you don’t want to, and not to be scared.
Jack arrived punctually at 5, and seemed a little flustered seeing Emily. I told him that Emily needed a little help in physics, and strategically flashed him a bit of cleavage yenibosna escort and shot him a look, so it was not surprising to me that he agreed to help her. We started by going over the 2 chapters that I worked on alone, and Jack seemed impressed at how well I had done. It wasn’t perfect, but he said that I had come a long way in just a couple of days.
He worked for a while on Emily’s issues, which were minor compared to mine, and then we went back to the review book and continued to plow through it. As with the prior time, Jack was a great teacher, and I felt like I was really making progress in understanding this.
After about 2 hours, I pushed back from the table and said, “That’s it, I’ve had enough.”
Jack complimented us on our work, and sounded sincere. He kept looking at me in a way that I understood to mean, “What’s going on?” I guess he thought that Emily’s presence meant that we were not going to do it, so he started to get ready to leave.
I said, “Stay, please. I have to ask you something.”
“What?” Jack asked.
I looked at Emily to confirm, and she nodded, shyly. “Emily is a virgin,” I stated. I saw Emily blush and lower her eyes. “I suggested to her that you might be willing to help her change that. I told her about what Ariel had done for you, and that I thought that you would be gentle and treat her well, but also show her a good time.”
Jack sat there quietly, thinking. He looked at Emily, then at me.
“Of course,” he said, smiling at Emily. “How could anyone resist you, Emily? I would be honored to be your first,” he said, awkwardly.
I smiled. This was the kind of thing that I loved.
“O.K., you can use my room. Emily, why don’t you go up and get comfortable?”
Emily turned and nervously walked upstairs to my room. I took Jack’s arm and said, “I thought you would be willing to do this, and that you would be gentle and nice. Emily is great, but she had a very protective, religious family. This is a huge deal for her. Oh, and there are condoms in my night table—make sure you use them, Emily isn’t on birth control yet.”
“Don’t worry, I had a great first experience, thanks to Ariel, and I will do my best for Emily,” Jack responded, and went upstairs.
His earnestness and willingness to please was refreshing.
I turned on the TV so that I wouldn’t hear them upstairs. I was actually kind of turned on by the fact that they would be doing it in my room. And I still intended to screw Jack, after Emily had primed the pump, so to speak. I was watching some show about expensive houses, and could still hear them going at it upstairs. Then I was watching some show about ghosts, when they came downstairs. Emily was beaming, and Jack looked pretty pleased, too.
“It was all good?” I asked.
“All good,” both Emily and Jack responded, laughing.
“You sounded like you were having fun.”
Emily blushed, and Jack shrugged. “That is what you wanted, right?” Jack asked.
“Absolutely,” Emily responded.
She looked at her watch. “Damn, I need to go home. My parents will be wondering where I am.”
Jack gave her a friendly kiss good night, and Emily said, “good night,” and walked out the door.
Jack turned to me and said, “I guess I should go, too.”
“Why?” I asked, fixing him with my best stare. “I’m not done with you. Especially now that you are warmed up,” I whispered to him.
“Seriously?” he asked.
“Seriously,” I responded, pressed myself against him and kissed him on the lips. I pulled away and said, “By the way, I heard that you asked out some girl from South, but it didn’t go well.”
He looked at me with surprise. “Uh, yeah,” he said, “Fiona Callahan, from South. Know her?”
I replied, “Nope, never heard of her.”
“How did you know that?” Jack asked.
“I make it my business to know these things,” I said, trying to be mysterious, and kissed him again before taking his hand and leading him back upstairs.
When we entered my room, the bed was a mess, and there were small bloodstains on the sheet. I looked at Jack, and shook my head, then stripped the bottom sheet, laying down the top sheet over the mattress. I thought for a second before saying, as I got undressed, “I can’t believe it, but I have been thinking of doing this with you again ever since you left on Tuesday.”
Jack responded, “me too.”
I continued, “in fact, I thought about trying to get you over here yesterday, but decided to wait.”
As I talked, Jack was staring at me hungrily, and I could see his cock rising in his shorts. He ripped off his clothing and threw them on the floor, exposing his strong chest and shoulders and his large, throbbing cock. He walked behind me and pressed his cock against my butt as he removed my bra, and caressed my tits. I melted into him as he pressed his cock into my ass. Jack then walked around to my front, and slowly pulled down my panties. He took a deep breath, appearing to draw in my scent zeytinburnu escort and smiled.
He firmly but gently pushed me down so that I was sitting on the edge of the bed and he knelt in front of me and began licking my pussy. It felt good, and tickled, and I laughed and pressed the back of his head into my crotch. I was tingling all over. I lay back and spread my legs almost into a split, so that I was wide open, and he could have his way with my pussy.
“Cheerleading does have its benefits,” I said, laughing.
His attention to me was unbelievable. He licked me all over and used his fingers to probe inside me. Occasionally, he would reach up and fondle my breasts. I was writhing with pleasure, and was pressing my hips up against his face. I was panting and writhing when he started to suck on my clit, which made me crazy, and I yelled out and was thrashing on the bed. Despite my activity, Jack kept licking, and he reached behind me and started teasing my asshole.
I was in ecstasy, and was moaning and writhing until I had an intense orgasm, which caused me to scream out and start shaking. When it passed, I lowered my ass to the bed and dropped my feet to the ground to regain my balance. I could not believe how this guy just rocked my world.
But he was not done. He stood up, his thick long cock pointing up and quivering. I was still paralyzed from the orgasm, and he gently spread my legs and pushed his cock into me. He thrust hard, and I wrapped my legs around his waist. Using the leverage from his feet on the floor, he started banging away at me hard, and it was incredible.
He switched between thrusting and rocking, and my head was close to exploding. I realized that he had already screwed Emily, so he would be in no rush, and I smiled at the prospect. I arched my back to meet his long, hard thrusts, and kept squeezing his back with my legs. I started to lose control, breathing harder and harder, until I came again. My vaginal muscles squeezed his cock, and I heard myself yelling his name as he filled me with cum.
If anything, that was even better than the first orgasm of the night. Jack fell on top of me as his cock slipped out. He stood up and sat next to me on the bed. I must have looked awful, sweaty and mussed, with cum leaking from my pussy, but he didn’t seem to mind. I reached up and rubbed his back a little, feeling the scars that Cara gave him. He reached out his hand and helped me to a sitting position and looked at me, smiling. I smiled back and licked my dry lips. “That was exactly what I needed,” I purred. “But my mom will be home soon, so we better clean up and get dressed.”
A little while later, we were cleaned up and dressed and straightening up downstairs, when Mom came in, looking pretty. We chatted briefly, and she grabbed her wine and went upstairs. I told Jack about the party that I had planned for Saturday, and invited him. He asked if Gina and Fred could come, and I said yes.
What he didn’t know, and what I couldn’t really let him know, was that at that moment, had he asked me pretty much anything, I would have said yes. But it was way too soon for me to admit to the world how I felt about Jack Davis. I had a certain reputation to uphold. Instead, I asked him for another tutoring session for the next night, which was Friday. I legitimately needed the tutoring, and I wanted more of his cock and tongue, but my ego needed to still make it look like I was allowing him to fuck me, and not that I was asking for it. I was not surprised that he agreed. He gave me a little kiss and left.
I texted Emily, to make sure she was O.K., and she said, “I’m great. That was fun. Do you think he would do that again?”
I really didn’t want to share Jack with her, but I couldn’t tell her that. Instead, I texted back, “I don’t know, but I think it would be awkward if we were both sleeping with him, so let’s find you someone else.”
I think that she got the message. I then texted Jessica and cancelled our plans to go out on Friday night to try to get into a bar and pick up some college guys.
“You O.K.?” she asked. “I thought that you were ready to go out again.”
“Yeah, I’m fine, but I have a tutoring session.”
“Seriously, how late will that go, we can go out at like 10,” she responded.
“No,” I texted back. “I’ll probably just hang with Jack.”
Jessica texted back, “Really? Is his cock a magic wand or something?”
“Not exactly,” I responded.
She didn’t text back, and I was glad, because I was close to admitting my infatuation with the class valedictorian.
I went back to the physics book and began to read the next chapter. I could not believe that it actually made some sense. I worked on the questions for a while, occasionally checking things on the Internet, until I thought I got most of it right. There was still one question that was impossible, but I knew that Jack would be able to explain it to me.
I was relaxed, satisfied and mellow. I found some mecidiyeköy escort ice cream in the freezer, grabbed a spoon and sat in front of the TV, slowly letting the chocolate melt in my mouth. Eventually, I went up to my room, changed my sheets, checked Facebook one last time, pulled up Jack’s profile to see if he had posted anything about us, and was happy that he hadn’t. I didn’t care if people knew we fucked, in fact, I started that story, but I didn’t want him to be boasting to his nerd buddies about it.
On Friday, I completely stunned Mr. Stone by answering a pretty tough physics question, and getting it almost right, and when he started to point out my mistake, I realized what it was, and corrected it. It was easy when I could hear Jack’s explanation in my head and see the notes that we worked on. It struck me that the regular physics class that I was in was for averagely smart kids, and that in reality, I was better than that, when I paid attention or cared. Now, between the fear of losing my chance to go to college, and all that would mean, and wanting to make Jack proud, I was working at least close to the level I could. Which was kind of a revelation to me. I had always succeeded because of my looks, but I also realized that my ability to reach the top of the social heap at North was also based on being smart.
Before lunch, I remembered that I would be passing Jack’s locker, and when I did, he called me over. Last week, even if he had the balls to call out to me, I would have walked right by him, but today, I walked over to his locker, as everyone in the hall watched. This whole thing with me and Jack was the talk of the school, and no one knew exactly what was going on. I kind of enjoyed that. I touched his arm familiarly, and asked, “Hey, Jack, what’s going on?”
“Not much,” he responded. “But I have a couple of ideas I wanted to run past you.”
I started to get a little turned on and looked at him in a way that seemed to fluster him.
He recovered and said, “No, not about that, at least not about us, I guess.”
I turned down the heat and looked at him.
Jack continued, “O.K., so first, I was thinking—your mom and my dad should meet—maybe they would like each other, I mean, they are both single and kind of lonely.”
I thought about it for a second. “Actually, that seems like a good idea. Let me ask Ariel what she thinks and if she likes the idea we can try to make it work.”
“You know, I should discuss it with Sarah, too,” he suggested.
“O.K., what’s the other idea?” I asked.
“This is sort of a reciprocation thing,” he started, his voice low. “My friend Fred, you know, until last week, we were both 18 year old virgins, and we could commiserate. But now I’m not, and I know he is jealous.”
“What do you want me to do?” I asked a little horrified, “fuck him?”
“No, no, no,” he responded quickly.
Good, I thought. Actually, I probably would have done it as a favor to Jack, but I didn’t really want to, even though it was pretty much exactly what I had asked him to do with Emily.
Jack continued, “But what about Emily? Do you think that she would agree to sort of ‘pay it forward’?” he asked.
Perfect, I thought, and chuckled. “So Ariel was your first, then I asked you to be Emily’s, then we ask Emily to be Fred’s? I like it. I’ll ask her later. Based on how much she enjoyed her first time with you, I’m guessing she would be up for it.”
“Great,” he responded—”let’s talk later.”
“O.K., I replied. “And same time tonight for tutoring?” I asked, giving him my best look again. “Just me, this time, by the way.”
“Sure,” he stammered as I walked away.
After lunch, I found Emily, and told her Jack’s proposal. I admitted that Fred was not as cute as Jack, but he was Jack’s friend, and it would be nice to “pay it forward.” I think that Emily had realized that she liked sex, and that this was a little wild, considering her parents’ religiousness, so she was up for it. At the end of the day, I found Emily and we went to the parking lot, hoping to find Jack. He was walking to his very nice car, and I called out his name.
He turned and walked back to us and Emily said, “Dana told me your idea, and, you know, I’m in.”
“That’s great, you can’t imagine how happy he will be.”
Emily smiled at Jack. “Actually, I can,” she responded, and it was his turn to smile.
“Three things, though,” he said. “Please don’t let him know that we had sex, or that we planned this. And please try to make it look natural.”
She responded, “Makes sense to me.”
“See you later,” he said to them and went to my car. I briefly watched his butt as he went to the car, then turned and went to mine.
I went home and killed a little time online, did a little studying for a non-physics final, and then reviewed the work that Jack had asked me to do. I showered and put on a t-shirt and shorts that were flattering, but not over the top, although I decided to go braless, just to see if he had any reaction. I brought the physics books to the table and watched TV.
Ariel came home from the restaurant and changed out of her work clothing, grabbed a beer from the refrigerator and sat down next to me. We made small talk about the restaurant—there was some good gossip about one of the cooks that Ariel wanted me to know—and about school.
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