When I Met Lily

When I Met Lily

It was my birthday. I was turning 15, and my parents were making a big deal of it. They had invited the entire family… even those cousins that I don’t even know. I was very disappointed when my parents told me that they wanted a “family” birthday this year. I had been planning a fun day: friends, pizza, cake, video games, movies, more video games, etc. And two weeks before my birthday, they blew it. They insisted that instead of friends, I should have a huge family birthday.

I was not impressed to say the least, and the only reason I agreed to it, is because of what they said I could have after my birthday. They told me that since I was 15 now, when we went to the cottage I could stay in the guest house out back. I had been bugging for it since I was 12, and now that I am a “man” they say, I can live independently out back in the guest house.

Fast forward three days. We are throwing our luggage in the car for the long journey to the cottage. OK, maybe it’s not that long, but for a bored fifteen year old, four hours was a long time.

After finally arriving, I unlocked the door to my home for the next 2 weeks, and was immediately met with the musty smell of the guest house. It wasn’t too pretty, but it was independence. I began unpacking when I heard a laugh, and some screams from somewhere outside. I ran outside to the lake and saw to my delight some girls playing in the water. There was a small girl, maybe 10 years old and she was splashing up a storm. But it was the other girl that caught my attention. She looked to be about 13 or 14, but it was hard to tell in the water. Just then, my mother came outside.

“Jake, would you mind running next door to ask if we could borrow some sugar. Looks like we forgot ours at home, and I don’t want to go into town until tomorrow.” She asked.

I was startled and realized that I had been staring. “Ummm… Ya. Ya! Of course.” I stammered. This was my chance to get a closer look at the girls.

As I wandered through the line of trees to the neighbours cottage, I noticed that I couldn’t hear the girls anymore. As I emerged on the other side of the trees, I saw them drying off. What a beautiful body she had. She stood at about 5’4”, with beautiful tanned legs. Her caramel coloured hair hung down, just past her shoulders, but it was her piercing blue eyes that really stood out. I don’t know how long I stood staring at her, it could have been ten seconds, but it could have been ten minutes.

“Can I help you son?” asked a deep voice from behind me.

I jumped almost a foot in the air! “Huh?! No! I mean yes! I mean can I have some sugar?! Agh!” I blurted out.

“You wanna try that again kid?” asked the man. I said, “Yes please. My name is Jake, and I live next door. I was wondering if we could borrow some sugar?”

“Well nice to meet you Jake. I’m Philip, and of course you can borrow some sugar. Come on in and I will get it for you.” Said he, and then, looking over my shoulder, “Lily! Lexie! Time to come in for lunch!” he shouted to the two girls.

I followed the man into the cottage, where he introduced his wife, Trudy, and his daughters. His youngest, Lexie, was 11, and his eldest (whom I was very interested in) was Lily and she was 15 next week. I shook all their hands, and Trudy suggested that I come over later for a bon fire.

I ran home with the sugar, asked my parents, gulfed my lunch down and ran to the guest house. I wanted out of my clothes and into my bathing suit. I wanted into the lake!

I closed and locked the door, and pulled my shirt over my head. I had a nicely tanned body, and for a 15 year old, I think I had a pretty nice body. While I wasn’t super ripped, I had enough muscles to look fit. I had a faint trace of a six pack, but I wasn’t concerned about developing it. I pulled my pants down and admired my body in the mirror. I stood at 6’0”, about 150 lbs. I had short brown hair, with blond streaks and dark brown eyes. I pulled my boxers down and admired my body again. At 15, my cock was not fully developed, but it was pretty close. It was about 5.5” of erect circumcised penis! Not too bad for a 15 year old!

I ran to the lake in my knee length, lime green bathing shorts and jumped in. The water was cool and refreshing, and almost immediately felt “the cold lake affect.”

I swam around for about 20 minutes before I noticed her. Lily was watching from a lounge chair on her deck. She was hiding behind a magazine, but definitely watching me.

I made a big show of climbing out of the water onto the dock, and allowed my bathing suit to cling to me, outlining my package. Then I bent over slowly and picked up my towel, and began to dry myself off slowly. I was trying to give her a show.

I spent the rest of the afternoon unpacking and helping my mom fix supper. Dad was outside fixing a broken plank on the deck.

After dinner, I put on track pants, a baggy sweater, and some smelly bug spray and headed over to the bon fire. They were just starting when I got there, and I took a seat next to Lily. She smiled at me shyly. I didn’t say anything, and neither did I. We had a pretty awkward hour sitting there, until I noticed what book was beside her.

“You read Harry Potter too!?” I asked.

“Yes! They are like my favourite book!” she said cheerily.

“Me too!”

And that was it. We talked for three hours. About books, about school, about friends, about boyfriends and girlfriends. All sorts of stuff. It was almost 11 when Philip sent me home.

The next morning I didn’t bother getting dressed; I just threw on my bathing suit and ran into the cottage for breakfast. I wolfed down a bowl or Raisin Bran, and then ran to the water. The cool water was almost sharp on my still tired body. I splashed around for about five minutes before Lily came out to join me. She explained that her sister was still sleeping and her parents were busy working around the cottage. She was talking to me, but I wasn’t really listening to her… I was admiring her! Her beautiful, shiny, straight hair hung down, just passed her shoulders. Her cherry red bikini top had little triangles covering her small but perky breasts. I estimated them to be a B, which is not bad for a 14 year old. Below her breasts was her beautiful, tanned, smooth, stomach with her perfect “innie” belly button, and below that was her cherry red bikini bottoms, covering her pussy. And below that were her beautiful, smooth, tanned legs.

She jumped off the dock, over top of me, and before she hit the water, I had a nice view of her ass. Oh how perfect that small round ass looked. I could feel my cock growing hard under the water.

We splashed around, pretty uneventfully, for about 30 minutes.

“I think I am gonna get out soon to work on my tan.” Stated Lily.

“Not if I have anything to do about it!” I shouted.

Then I dived towards her and she shrieked. I picked her up and threw her thrashing a couple feet through the air into the water. She came up laughing, and I came up hard again.

She dove under the water and swam swiftly towards me. I didn’t have time to dive out of the way, and she swam under me, through my legs. I felt her hair, and then her leg graze my cock.

Oh god! Had she felt me? Did she know I was hard? Did she think I was some kind of pervert? She came up for air on the other side of me and said she had to get out so she could tan. I thought I blew it with her, so I left the water feeling pretty depressed about myself.

After drying off, I pulled my bathing suit off and saw that I was still hard. Immediately all I could think of was her. I decided I needed some “stress relief.” I lay down on my bed, spit in my hand, and started stroking my hard cock. Oh it felt so good thinking of her. How I wanted her so! I needed her! I continued to think about her for 4 minutes, and before I knew it, I had that tightening feeling in my balls. I started to moan quietly, and pumped my hand up and down my penis faster and faster, and then I erupted. One squirt, two, three, four, five squirts!

After getting dressed, my mother asked me if I wanted to go into town with her. I said sure, and ten minutes later we were off for the 30 minute drive to town.

At the grocery store, I went off by myself, because shopping with my mother is really boring. I was looking at magazines, when I heard a familiar laugh nearby, and to my surprise saw Lily standing in the pharmacy aisle, looking at sun tan lotion.

“Hey Lily!” I said as I walked down the aisle towards her. Her little sister had just run off to the chocolate bars, and it was just us in the aisle.

“Hey big boy.” Smirked Lily. I looked at her, startled.

Then she reached her hand back, and pushed a package of condoms into my basket. “You might need these later.” She smiled.

Before I could ask what she was talking about, she walked off to join her sister. Was she joking? Was she serious? I didn’t know, so I bought the condoms anyway. I couldn’t believe my luck. I could lose my virginity tonight! I could hardly contain my excitement. But surely she must be joking.

We got back to the cottage, and I spent the rest of the afternoon trying to read. All I could think about was the condoms hiding in my dresser. Oh how I wished she wasn’t joking.

After supper, I helped with the dishes. Then we went out on the boat, and watched the sunset. I went to bed around 10, dreaming of that beautiful body on top of mine.

I was awoken with tapping at the window. I looked up startled, and was shocked to see the beautiful smiling face of Lily staring back at me.

“What are you doing here?” I asked as I let her in the door.

“Oh as if you don’t know. I have been watching you since you got here, and I know you have been watching me. Look Jake, I really like you and I think you really like me. Am I right?” she asked.

“Yes… I mean… I guess.” I said, my ears burning with embarrassment.

“We only have two weeks together, and I don’t want to leave you, and have to wonder for the rest of my life; What if he took my virginity?” she said is a sheepish voice.

My heart was beating like crazy. “What are you saying?” I asked.

“I want you to be my first Jake, and I want to be your first.” She said.

I smiled and embraced her. We moved over to the bed, and I kissed her softly on the lips. We started making out, and I started to feel her up. She reached down and pulled my shirt up over my head, and I did the same for her. I continued to kiss her, our tongues dancing together as I unclipped her bra. My hands closed around her breasts as we lowered ourselves to lie down on the bed.

I started to massage her beautiful, perky breasts while we continued to kiss. She started to moan and unbutton my pants.

I broke our kiss and started sucking her nipple, and flicking it back and forth with my tongue. She started moaning faster and almost ripped my pants off! She pulled me so tight and I pulled her pants down, revealing the hottest undies I had ever seen. It wasn’t a thong, but it was still small and skimpy. Red, with darker red stripes and a neat little bow at the top. I only saw them for a moment, because I pulled them off and threw them on the floor with her pants, shirt, and bra.

We were now completely naked except for my blue plaid boxers. We rolled around on the bed groping and kissing each other, each of us moaning lightly. I reached my hand down, and started to rub my finger around by her pussy. She started moaning louder, so I started playing with her clit.

“Oh! Ok Jake! Ya baby! Ya!” she moaned.

Encouraged, I continued for a few minutes, until I placed my middle finger at the entrance of her pussy. I had read that the first time was often painful for the girl, and I didn’t want to hurt her so I very slowly applied pressure.

My finger slipped between her dripping pussy lips into her. She gasped, and I pushed further. She moaned, and I started pushing in, and pulling out with m finger. She seemed to be loving it. I kept at this, and started sucking on her nipple again. She moaned even louder.

After a little more than two minutes, I began to play with her other boob with my unoccupied hand, and she started to moan so loudly, she was practically screaming.

“Agh!!!!!! I’m going to cum Jake! You’re going to make me cum Jake!” she moaned.

And with that, she began to convulse, and moan very loudly. She did this for about 40 seconds, and then I realised that I had made her orgasm. I was quite proud of myself.

“Oh Jake! That was awesome! That’s the best orgasm I ever had! Way better than when I do it to myself! Now it’s your turn!” she said.

Then she rolled me onto my back, pulled my boxers off, and started staring at my penis. “It’s so much bigger than I thought!” she said.

She then proceeded to kiss the head, and then lick it. After a few more seconds’ hesitation, she put my rock hard cock into her mouth. She was an amateur, but so was I. And this felt amazing. She put almost all of it in right away. Then pulled it back out, and said, “I have no gag reflex.” I smiled, and couldn’t believe my luck. She got back to work immediately, and began to suck me. She was doing such an amazing job. It was the most incredible thing I ever felt, and I soon lost track of time. I can’t even say how long she did this to me, but eventually, probably not too long after, I stopped her. She looked up at me and said,

“I’m ready. I want you in me Jake. I want you to fuck me right now.”

“If you are sure.” I said. And with that, I grabbed the box of condoms, and slipped one on.

She lay down on the bed and spread her legs. I placed my cock at the mouth of her pussy. “Do it.” She said.

And with that, I pushed into her slowly. I felt a slight obstruction, which I knew must mean she was truly a virgin. I applied a little more pressure, and in I went. We gasped at the same time. “Please wait Jake.” She asked, tears almost in her eyes. And that’s what I did. I waited for almost two whole minutes, and then she asked me to continue. I pulled out slightly, and pushed back in. I did this for several minutes, barely moving so she could get used to it.

Once her look of pain subsided, I pulled further out, and pushed in deeper, faster. With that, her expression turned to one of pleasure. I loved the feeling of her all around me. She was so tight, it felt so amazing. I didn’t know how much longer I could hold it.

I continued to push in deeper, and started thrusting faster. She started to moan loudly, and started contracting a muscle somewhere in her body. It felt amazing to me, and I soon started moaning to. I pounded my 5.5” penis into her, over and over again for about seven minutes before I started to feel that tightening sensation. I knew I was almost done, and from her breathing I could tell she was too.

“Oh baby! I’m going to cum soon!” I said. “Me too! Just do it!” she said.

And with that, I started to thrust faster. Another thirty seconds, and I felt her tighten up around me. I realised what was happening; we were both having an orgasm at the same time.

Strings and strings of my cum shot out of me, and I moaned loudly. Things must have been good on her side too because she was moaning just as loud.

When we finished, I rolled over and looked at her. She smiled, and we fell asleep in each others arms. This was going to be the best two weeks of my life.

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