The Lake House Lessons 05

When I showed up at Dana's house that evening, I was surprised to see Emily, another girl in her clique. Emily was pleasant enough looking, with a nice body, and somehow had insinuated herself into the in crowd, despite not being a cheerleader or exceptionally hot.

"You know, Emily," Dana asked, "right?"

"Not really," I responded. I shook her hand awkwardly and said, "Jack."

Emily said, a little nervously "Yeah, I don't think we've ever actually met, but Dana has told me a lot about you."

Dana interjected, "Emily needs a little help in physics, so I hoped that you wouldn't mind if she sat in today."

She bent slightly to give me a view of her cleavage then shot me a look that I felt in my crotch, so it was not surprising that I agreed. I sat between the two of them and we went over the next few units. Dana definitely began to make some progress, and Emily, it seemed, was actually in pretty good shape on the material, but just needed a little push on a few things.

I was admittedly a bit of a physics nerd, and loved talking about it, so I didn't even notice that we had gone more than two hours without a break.

Finally, Dana pushed away from the table and said, "That's it, I have had enough."

I complimented both of them on their work and they thanked me. I waited for Emily to leave, so I could get my hands on Dana, but she didn't make any move out the door. I figured that Emily's presence would prevent me from getting my "compensation", so I got up to leave.

Dana said, "Stay, please. I have to ask you something."

"What?" I asked. She looked at Emily, who nodded, a bit shyly.

"Emily, here, has turned 18 last week and is a virgin," Dana stated.

I saw Emily blush and lower her eyes.

"I suggested to her that you might be willing to help her with that condition. I told her about what my sister had done for you, and that I thought that you would be gentle and treat her well, but also show her a good time."

I sat there quietly, thinking. Now, I was the experienced one? The world really had turned. I looked again at Emily. She was no Dana, but who was, really? But she was far, far from repellent. And I knew from recent experience that this must have been really hard for her to allow Dana to raise with me. I could tell that she was uncomfortable.

"Of course," I said, smiling at Emily. "How could anyone resist Emily? I would be honored to be your first."

Dana looked at me and smiled. "O.K., you can use my room. Emily, why don't you go up and get comfortable?"

She turned and nervously walked upstairs to Dana's room.

Dana grabbed my arm and said, "I thought you would be willing to do this, and that you would be gentle and nice. Emily is a great girl, but she had a very protective, religious family. This is a big 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."

I went up to Dana's room. I could see that Ariel was not in her room, which was good. This situation was really odd, but at the end of the day, I was about to have sex with another attractive girl from school, who would actually be grateful to me for screwing her. Not to mention, Dana would be pleased, which could only be good for me.

When I got to Dana's room, the door was open but the lights were off. I could make out a shape in the bed, under the covers. I turned on Dana's desk lamp, which threw off a little light, and closed the door. Emily was under the blankets, which were pulled up to her chin. I kicked off my shoes and sat on the bed.

"Please give me your hand," I asked.

She wriggled a hand out from under the blanket, carefully not exposing anything, and gave it to me. I held it in my hands, feeling her trembling a little, and said, "We really don't have to do this, if you don't want to. I'll even say we did, if you want."

"No," she responded. "I want to do this, I'm just scared."

"There is nothing to be scared of," I said gently. "Look, you know that until last Saturday, I was a virgin like you, and then, I wasn't. It felt great, and it was fun and sex really feels good."

"Really?" she asked.

"Yes," I responded, "We will take it as slowly as you want, and we won't do anything you don't want to. In fact, we will stop anytime you want."

She smiled, and when she did, she seemed to relax. Her face was round and fair; she had blue eyes and auburn hair. I slowly leaned toward her and kissed her on the lips. We awkwardly kissed for a while, and the kisses gradually increased in quality and passion. I noticed that she was still wearing her bra, as I began to stroke her neck and shoulders. I pushed the covers down just an inch or two, revealing the softness of her creamy white upper chest and the top of her bra cups. Her tits looked to be of pretty good size, roughly like Ariel's. I took off my shirt and pressed my torso against her at an angle so that my cock, which was growing in size, was still against the bed. Taking it slowly. I kissed her neck and breasts above the bra, moving the covers down a few more inches until her breasts were fully exposed. Her bra was plain but sheer, and I could see her dark nipples poking slightly through the fabric.

I started to gently caress her tits, through the bra, and she began to moan slightly, close her eyes and tilt her head back. I continued to do this until she sat up a little, reached behind her back, unclasped the bra and pulled it off. Her breasts were very nice. Round, white and firm with small round areolas and a nice sized dark nipple. I took them in my hands and looked at Emily.

"You are very beautiful," I said.

She smiled and I took that as a signal to begin kissing her tits and sucking on her nipples. She closed her eyes and threw her head back against the pillow, letting out sighs and moans, and wiggling her hips under the covers. She pressed my head against her chest, encouraging me to keep going. I became very aroused at this point, but realized I still needed to take things slowly. I pushed the covers down further, exposing her soft, flat belly. I could see she was wearing white panties. I kissed under her breasts, then softly down her body until I reached the top of her panties. I then reached down and put my hand between her legs. Her panties were soaked. I kept rubbing her over the panties and could tell that she had a pretty full bush under there. She was writhing like crazy and pressing herself against my hand, still moaning and sighing. I was dying to stick my rod into her, but knew I should go slow.

My hand began to reach under the waistband of her panties, until my fingers felt her pubic hair. It was full and curly. Emily lifted her hips off the bed, which I understood meant I should take her underwear off, so I slid it down, throwing the covers back to expose her nice legs, and then over her feet. I tossed them on the floor and looked back at her, fully naked. I still was wearing my shorts, and my cock was pressing hard against them.

But instead of ripping them off, I started to rub Emily's legs, occasionally brushing against her crotch. She spread her legs, and I could see her lips, with her juices dripping on to the sheets. I started rubbing her lips, gently inserting one finger into the slippery hole, which caused her to moan harder and pant. My fingers explored her gently, and I started to finger her clit. She threw her hips into the air as if shocked, and gasped.

"O.K.?" I asked.

"Oh, yeah," she said, dreamily, but began to breathe heavily.

I increased my attention to her clit which caused her to writhe and throw her hips into the air until she screamed, "Oh my god" repeatedly. I kept going until she stopped thrashing and screaming.

Emily looked at me, her eyes on fire, and said, "That was amazing."

I said, "Thanks, I'm glad you enjoyed it. Can I show you what you have done to me?"

"Yes, please," she said enthusiastically.

I stood up and took off my shorts and boxers, and my cock was standing straight and pointing right at her.

"Wow," she said. "Dana said it was big, but I had no idea."

"Yeah," said, "it is, I guess."

"Can I touch it?" she asked.

"Of course." I got on the bed and she reached out, gingerly, and grabbed it, just below the head.

"Can I kiss it?" she asked, shyly.

"Absolutely," I responded.

She leaned forward and kissed my tip. Then she put the head in her mouth.

"That feels great," I said encouragingly.

She took me out of her mouth and said, "Will that fit inside me?"

"It should," I replied.

"Then let's try" she said, with a combination of fear and excitement.

I reached into Dana's night stand and grabbed a condom. I had never used one before, but didn't want Emily to know that. I tore open the package and was able to figure out how to slide the sheath over my cock. I kissed her and positioned myself above her as she spread her legs wide. I lowered myself so that the bottom of my cock pressed against her lips without trying to enter. I wiggled my hips against her, and she responded in kind. I could feel that she was slick and ready. I reached down and guided the tip until just the head was inside her. She moaned and opened her hips as if welcoming me.

I pushed forward more, slowly, hearing Emily moan with pleasure and say, "oh my god, it is so big."

"Does it hurt?" I asked?

"No, no, no," she responded.

I pushed in deeper until I felt some resistance.

"This might hurt a little," I whispered, and pushed through what I guessed was her hymen.

Emily yelped briefly, but then pressed against me, so I pushed my cock fully in. She yelled out and started kissing my face. I slowly withdrew my throbbing member and then plunged it back in. Emily's hips left the bed to meet my thrust, and I began to thrust faster and faster. I felt Emily pressing against my cock, harder and harder, and she began to pant harder and harder. The condom deadened my feeling, so I wasn't even close to cumming.

She screamed out my name and dug her fingernails into my back as she thrashed under me with a tremendous orgasm. But I kept going, and a few thrusts later, she came again. Emily was moaning and laughing as I continued to pound her pussy until I came with a gasp. Worried about leakage, I quickly pulled my flagging cock out and flopped on my back. I reached over and pulled Emily close to me and held her in my arms.

"Are you O.K.?" I asked.

"More than O.K. That was great. Thank you," she whispered.

"No, thank you, I replied. You were incredible."

We laid there for a while. I grabbed some tissues off of the night table and handed some to Emily. I clumsily removed the condom and tied it off, noticing a little blood on the outside. Emily cleaned herself off, and we lay in the bed, together. I felt her hand reaching toward my cock, and she started to stroke it gently. It didn't take long until she had me fully aroused. While rubbing my engorged cock, Emily started to kiss my chest and stomach, and then moved down and began licking my shaft.

"Let me know if I do anything wrong," she said, "I've never done this before."

"Don't worry," I said, "that feels great."

What she lacked in technique, she made up with enthusiasm, and she soon had me on the edge of climaxing.

"I'm going to cum," I panted, "pull me out if you don't want me to go off in your mouth."

Instead of pulling me out, she stuck my cock in deeper, and I came with a rush. She gagged, but swallowed it down and looked at me with a satisfied grin.

"Wow, that was incredible," I said, as she cuddled next to me. We laid there as I stroked her hair.

After a while, she got up, and I could see her naked body, including the matted hair between her legs, and she put on what I assumed was Dana's robe, grabbed her dirty tissues and went out, presumably to the bathroom. I threw on my clothing, and when Emily returned, I grabbed the condom and the tissues, went to the bathroom and cleaned myself off. We stood awkwardly in Dana's bedroom, trying to figure out what to say.

Finally, Emily said, "I appreciate what you did. This is a night I will always remember in a good way. I have heard so many bad stories about girls losing their virginity to jerks, that I am happy that mine was great. Even if we never do that again."

I hugged and kissed her, and we walked together downstairs.

Dana was watching television. "All good?" she asked.

"All good," both Emily and I responded, laughing.

"You sounded like you were having fun."

Emily blushed, and I shrugged.

"That is what you wanted, right?" I asked.

"Absolutely," she responded.

Emily looked at her watch. "Damn, I need to go home. My parents will be wondering where I am."

I kissed her good night, and Emily said, "good night," and walked out the door.

I turned to Dana and said, "I guess I should go, too."

"Why?" she asked, fixing me with that irresistible stare. "I'm not done with you. Especially now that you are warmed up."

"Seriously?" I asked.

"Seriously," she responded, and pressed her awesome body against mine, kissing me on the lips. "By the way, I heard that you asked out some girl from South, but it didn't go well."

I looked at her, surprised that she not only knew, but that she cared to know.

"Uh, yeah," I said, "Fiona Callahan, from South. Know her?"

Dana replied, "No, never heard of her."

"How did you know that?" I asked.

"I make it my business to know these things," she said, mysteriously, and kissed me again before taking my hand and leading me upstairs.

When we entered her room, the bed was a mess, and there were small bloodstains on the sheet. Dana looked at me, and shook her head, then walked over and stripped the bottom sheet, laying down the top sheet over the mattress.

"I can't believe it," she said, as she took off her clothing, "but I have been thinking of doing this with you again ever since you left on Tuesday."

I said, "me too."

She continued, "in fact, I thought about trying to get you over here yesterday, but decided to wait."

As she talked, I was staring at her standing there in her bra and panties, and, as my cock hardened, I pulled off my shirt and shorts and threw them on the floor. I walked behind her, and pressed my cock against her ass as I unclasped her bra and took it off of her, running my hands over her firm tits and pressing my cock harder against her ass. I then walked around her and slowly pulled down her panties as I kneeled down in front of her, and she stepped out of them. Her spicy scent enveloped me and made me crazy.

I gently pushed Dana down so that she was sitting on the edge of the bed and immersed my face between her legs. She opened her legs wide, and I began lapping away like a dog. She laughed and pressed the back of my head so that my face pushed into her gap. Then she laid back and spread her legs almost into a split, so that she was wide open.

"Cheerleading does have its benefits," she said, laughing.

I licked all around her inner and outer lips and began to probe her with my fingers. Occasionally, I reached up and grabbed one of her beautiful breasts. She was writhing under my face, pressing her hips up as I tasted her flowing juices. As she started to move toward orgasm, I started to suck on her clit, which caused her to yell out and start thrashing wildly. I continued to lick her clit, and reached behind her and gently rubbed the area near her asshole. Based on her whimpering and writhing, she seemed pleased with this. She screamed out and shuddered, and her ass lowered to the bed, with her legs off the bed, bent at the knees.

I stood up, opened her legs and leaned in so that my cock entered her. I thrust hard, and she lifted her legs and wrapped them around me. With my feet on the floor, I pounded away, hard. Having already cum twice with Emily, I was in no rush, and kept alternating jack hammer blasts with side to side rocking. Dana arched her back to meet my thrusts, and she kept squeezing my back harder with her legs. I heard her breathing harder and harder, until I felt her contract inside, squeezing my cock and causing me to blow my load as she screamed my name.

I honestly don't think that I ever felt that good, that powerful. I buckled on top of her and my shrinking cock slid out. I stood up, then sat on the bed next to Dana, whose legs were still hanging off the bed, cum dripping from her pussy. She reached up and rubbed my back a little, tracing the fading scars left by Cara, then sat up next to me.

"That was exactly what I needed," she said. "But my mom will be home soon, so we better clean up and get dressed."

Ten minutes later, we were downstairs, and I was gathering my stuff when Mrs. Angelo came in. She was wearing a tight shirt, short skirt and heels, and looked hot. We exchanged pleasantries; she poured her wine and went upstairs. I said good bye to Dana.

Before I left, she said—"Jack, I am having a pre-graduation party here on Saturday night at 9. Should be a blowout. Why don't you come?"

"Of course," I said, happy that I had finally cracked the "cool kids" parties that were always going on without me. "Can I bring Fred and Gina?" I asked, figuring that my good fortune should benefit my best friends.

"Of course," she responded. "The more the merrier." Then she asked, "by the way, can we have another tutoring session tomorrow, same time? I really need it."

I wasn't exactly sure what she "needed", but I agreed.

I gave her a little kiss and walked out to my car, once again marveling at what was going on in my life.

Dad was not home when I arrived, but Sarah was watching TV. As I walked by her she looked at me, quizzically. I don't know if it was the look on my face, or my mussed hair, or maybe even a smell, but she asked,

"Again?"

I smiled and said, "You don't know the half of it."

Before she could pump me for details, I went up to my room and went online. There were more friend requests, including from the two underclass girls who had left me notes, and even some girls from other high schools who were friends with girls from my school. And one from Emily, with a smiley face message. I accepted them all.

I saw that Fred was on line. I messaged him that I had just got back from Dana's, and she invited us, and Gina, to a party on Saturday.

"Did you do her again?" he asked.

"Actually, yes," I responded.

I decided not to mention Emily, both to protect her reputation, but also because I thought it might get Fred pissed off at me. I told him that I would try to talk to Gina at school and tell her about the party. As I fell asleep, I thought of two good ideas, and hoped that I would remember them in the morning.