Dana's Side Ch. 01

I could feel him trembling a little, and he asked "Is your room next to your sister's?"

"Yes," I replied.

"Won't that be awkward?"

"Not really, um, look, this won't be the first time I've had a guy in my room, and she certainly has had her share."

We went into my room, and I closed the door and turned on a small lamp. I liked a little light on when I had sex—I liked to see the guy, and I think they liked to see me. Jack looked around my room and surprised me by coming over to me, and starting to kiss me. I expected, despite the reports from Ariel, that I would have to take the lead, but once I offered myself to him, he seemed to be willing to show initiative.

He pulled my shirt over my head, displaying the sexy pink bra that I chose, in case we got to this point. He leaned forward and tenderly kissed my neck and chest, gently holding my breasts in his hands. He pulled me close, and I could feel his hard cock pressing against me. It did seem to be pretty big. He reached behind me and fumbled with my bra strap before figuring it out and opening it. I tossed it off and he looked at them with what appeared to be awe. Which was cute, especially since he had seen some pretty incredible boobs over Memorial Day Weekend.

"Go ahead," I said, and he sat down on the bed, and stuck his face into my cleavage. He started to gently rub my breasts and kiss and lick my nipples until they were hard. It felt great, and I began to moan, and felt myself getting wet. It had been way too long, and Ariel was right that he seemed to know what he was doing.

While he continued to kiss and lick my breasts, I pulled down my shorts, then my panties. I had recently trimmed my bush into a triangle, and I stood there, in front of Jack and watched him look at me with lust, which I found exciting. He stood up, and I could see the substantial bulge in his pants, so I removed his shirt, unbuttoned his shorts and pulled them down before removing his plaid boxers. His cock jumped out at me, quivering. It was large, thick and beautiful.

"Ariel wasn't lying about your equipment," I said, grabbing it and stroking it gently as it twitched in my hands.

We fell onto my bed, and he slowly kissed me all over. I felt the scars on his back, which, he said, were Cara's fault, and he continued to sweetly kiss me. He reached down and began to gently stroke my pussy, and I was burning with desire, and dripping wet. I spread my legs and he took the hint, and started teasing me. I was gently stroking his head and back while my hips were writhing when he finally stuck a finger inside me.

He continued to tease me, either intentionally or accidentally avoiding my clit, when I wanted him desperately to touch it. Instead, he started to kiss and lick my tits, harder this time, and I could do nothing but moan and writhe. He began to finger fuck me, twisting his fingers, and I was bucking my hips in time with his thrusts, until he finally gave my clit a flick. I gasped with pleasure, as he began to stimulate my clit more and more, and stuck his fingers in me. It was incredible. He kept going, faster and faster until I had a huge orgasm that caused me to yell out. I wanted him inside me badly.

I opened my eyes and looked at his handsome, smiling face, smiled back at him and said, in a voice full of desire, "I want to feel that cock inside me."

"I didn't bring a condom," he said.

"No problem, you don't need one. Please get on top of me now."

He moved between my splayed legs, and slowly pressed his huge cock inside of me until he was fully in. It felt great, and I wiggled my ass as he slowly withdrew. I figured that he would cum quickly from the excitement, but I had, again, underestimated Jack. We slowly fucked, and I loved the way his cock filled me up.

I lifted my legs onto his shoulders, which allowed him to penetrate me even deeper, and I was trembling with pleasure. We started to go faster and faster, grunting and moaning with passion until I was on the verge of climaxing, when Jack yelled out "I'm cumming" and I felt a huge shot of cum shoot out of him and into me.

I let myself go, and had another incredible orgasm, and was pounding the bed with my hands. Jack fell on top of me, and I could feel his chest pressing against my sensitive, hard nipples. After a few seconds, he rolled off of me, then pulled me close to him to cuddle. It felt nice.

"Ariel didn't exaggerate about how good you were, either," I said softly.

"Thank you. How could I not want to bring pleasure to such a beautiful woman?" he responded.

How sweet, I thought. I smiled at him and snuggled closer. After a few minutes, I sat up and said, "My mother will be home soon, so we should clean up and get downstairs."

"Your mom doesn't know that you do this when she is out?" he asked.

"She knows," I responded, "but Ariel and I try not to rub her face in it."

"Got it," he said.

He tenderly kissed me again and stood up, wiped his cock with some tissues and grabbed his clothing. Jack looked out the bedroom door, and ran naked into the bathroom. I followed a few minutes later and went downstairs.

Jack was gathering his stuff, and said, "Dana—you can keep the review books and use them. When do you want another tutoring session?"

"I have to work tomorrow, so how about Thursday, same time and place?"

"Same everything?" he asked, smiling playfully.

"Wow, you really have changed from the shy guy who never talks to anyone," I noted.

"I guess," he responded, "you can thank Ariel for that."

"I will," I said, "same everything—but maybe not exactly the same, that might be dull," I shot him my best, sexiest look, and I could see him blush.

The door opened and Mom came in. I said, "Mom, you remember Jack, we used to be friends in middle school, and he is going to help me pass physics."

Mom smiled at Jack and said, "It has been a while, Jack. Your sister is friendly with Ariel, right? Sarah?"

"Yes, ma'am," he responded.

Mom reached into the fridge and pulled out a bottle of white wine, and poured herself a glass. "Need to take the edge off at the end of the day," she said. "Anyway, thanks for helping Dana. We need her to keep her scholarship. We can't pay you much, but—"

Jack interrupted. "Mrs. Angelo, don't worry, Dana and I have it all worked out."

She took her glass and headed up the stairs.

I looked at Jack and said, "I think she drinks too much, but she has been lonely since Dad left."

Jack looked uncomfortable, and said "it has been a long time, right?"

"Yeah," I responded, "Too long."

"But she is still very attractive; I can't imagine she would have trouble finding someone," Jack noted.

I thought for a second before responding. "I think that Dad leaving ruined her confidence. I mean, I've seen pictures—when she was younger, she was so beautiful, and she and Dad fell madly in love. But then, well, then he started cheating on her and left for a younger woman."

"That sucks," Jack said.

"Yeah, I know. Then, I understand she tried to meet men, but no one was interested in someone with two kids, so she kind of shut down. Now, she works late every night to make enough money for us to be able to do extracurriculars at school and go to college, comes home and has dinner, sometimes too much wine, and goes to sleep. And on the weekends, sometimes she works, and sometimes she just does things around the house or watches television. I wish I could think of something to do."

It struck me that I was telling this personal stuff to a guy who two days ago, I wouldn't have said "hello" to at school, not to mention that we had just had great sex.

While I was thinking, Jack said, "Yeah, I wish there was."

He gently kissed me goodbye and left.

I went up to Ariel's room and knocked on the door before walking in. She was lying on her bed with her laptop on her flat belly.

"So?" she asked, "It sounded like you were having fun in there."

"Jesus, Ariel," I responded. "He was incredible. And you were right, not only did he seem to know what to do, he was so gentle and appreciative. What did you guys tell him? You should write it down and sell it."

Ariel smiled and said, "Basically, that he should be confident, not cocky. That he should be attentive to what the woman says and the hints she drops, both in bed and otherwise. That he should respect her feelings. That most women like cuddling and stuff like that, maybe as much as the actual sex."

"Well, so far, it seems like he has taken your lessons to heart," I said.

"Yeah, so far, so good. But according to Cara, he was not afraid to get rough with her, when she wanted him to, so he seems to be adaptable. And what about the tutoring?"

"Actually," I said, "he was great at that, too. I'm understanding the work, and actually enjoying it. You were right, he is a nice guy."

"Will you be seeing him again?" she asked.

"Yes. We are having another tutoring session on Thursday, followed by another bedroom session, I expect."

"Great," Ariel said. "I'm glad I could help." She turned back to her laptop and I went to my room and fired mine up.

I got chat messages from Lisa and Jess asking me how the tutoring went. I responded that it went well, that Jack was great, that we had slept together, and that he was hung, and really good. I figured the word would be all over school by the morning, and should boost Jack's social standing immeasurably. I thought I owed him at least that.

I went downstairs and read a chapter of the physics review book. It was not completely incomprehensible, so I read it again, checked some things on the Internet and worked on the questions. For some reason, I wanted Jack to be impressed with my progress. Eventually, I got tired and went to bed. I slept through the night for the first time in a while.