Teen
2006-12-04
Chapter 1 - The Proposal
"I need your help. Can I Come Over?". . . I had a very important date with Caroline coming up and I was intensely nervous. It was going to be the day I had sex with her. We had been going out for about a month and decided it was time to finally do it. She was the most beautiful girl I had ever seen. 5'8, long, curly blonde hair, a slim figure with B cup breasts, and the most amazing legs and ass I have ever laid eyes on. We had never really done anything sexually before. We only touched each other a bit and made out, but a few days ago she told me she wanted me to take her virginity. I was in complete shock. We had never discussed anything like that before. But who was I to turn down sex?
Anyway, I’m getting ahead of my self. My name is Alex and im a 18 year old senior in a Toronto highschool. I’m 5'11 and around 180 lbs (mostly muscle).
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I have brown eyes and brown hair. I’m really into sports and weight training. I’m a starting flank for my school’s rugby team and plan on playing professionally some day. And for those of you who must know. . . I have a 7 inch penis. Now back to the story.
My nerves were starting to take over. I couldn’t concentrate in school, at the gym, or on the field. I was so worried that I would be complete shit in bed. My friends kept telling me not to worry and that since she’s never done it before, she has nothing to compare to. All of that went through one ear and out the other. There had to be something I could do to make sure I could please this amazing girl. Then an idea came to me.
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You see, I have this very close friend. We’ve known each other since we were 6. We’ve always told each other all of our secrets and have always been able to completely trust one another. Her name is Emily, and I was about to ask her something that could change our relationship forever.
"Hello?"
"Hey Em, it’s me", I said through the phone.
"Hey hun, what’s up?", she replied.
"I need your help. Can I come over?", I asked.
"Sure, I’m not doing anything. "
I hung up the phone and left my house. Emily only lived a few blocks down so it was a short walk. As I walked, I began to think about Emily. She is one of the most amazing people I’ve ever known, second only to Caroline. She sweet, funny, caring, and has always been there for me. I could only hope she could help me with this.
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Along with her personality, she also is very attractive. She’s 5'6, has straight, shoulder length, blonde hair, a tight round ass, and C cup breasts. She is any mans dream.
I walked towards her front steps feeling as nervous as ever. What the hell is the matter with me?, I thought to myself, you’ve been friends with her forever, just suck it up. I rang the doorbell and she answered instantly.
"Hey you! How you doin’?" she said as I walked in the door.
"I’m alright", I replied "Is anybody home right now?"
"No, my parents are away for the weekend. Why?" she asked me with a slightly suspicious look.
"Don’t worry. . . lets go downstairs. "
We sat down and started talking about random shit that was happening in out lives. I couldn’t get up a courage to bring up the reason I needed to see her.
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Then, without knowing, she brought it up herself.
"So. . . how’s things with Caroline?"
"Everything’s okay. . . I guess. " I murmured.
"Well that doesn’t sound to good. What’s going on?" she asked.
"Here’s the thing. Two nights ago, Caroline asked me if I would take her virginity next weekend while her parents are gone. " I told her.
"That’s great.
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. . I don’t see the problem. . . " she said, looking confused.
"Well I’m worried I’m gonna fuck up while doing it. " I confessed.
"That’s ridiculous! I’m sure you’d be great. "
"Well I’m not. That’s why I came over. I know that you and Kevin did some things while you were going out. . . and.
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. well. . . would you have sex with me?"
Silence. I was scared to look at her so I looked at the ground. When I finally look up, I saw the most shocked expression on her face.
". . . what. . . " was all she could manage to spit out.
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"Look, we’ve been friends for a long time and I really need someone who’s close to me that can help me. I know that person is you. "
"Wow. . . I wasn’t expecting this," she replied, "Do you realize what something like this could do to our friendship? And what about Caroline? She’s one of my very best friends. If she ever found out, she would never want to see you or me again! You know I’m always here for you but there’s just to much risk. "
"I know there’s a lot of risk. . . but I don’t think anything can change what we have together, especially something like sex. I might just bring us closer together. "
"Fair enough. But did you think about how this would effect you’re relationship with Caroline if she found out?" she argued.
"She won’t find out.
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You wouldn’t tell her. There’s no way in hell I’m going to tell her. And she’ll benefit from it in the end. Please Em, I need your help. "
She looked at me thoughtfully for about 2 minutes and finally said, "Okay. I can see this is important to you and what kind of friend would I be if I didn’t help you out?"
"Thank you so much! You won’t regret this. " I leaned over and gave her a kiss on the cheek.
"I sure hope not. Now when do you want to do this?" she asked.
"How about right now?" I answered.
"Wow, somebody’s anxious. . . alright, lets go to my room. "
Chapter 2 - The Fun
I laid her down on the bed and began kissing her lips.
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She hesitated slightly, but became very involved almost seconds later. Amazing sensations ran through me as I felt her warm tongue connect with my own. This was so much different than kissing Caroline. I slowly began to caress her body and remove pieces of her clothing as well as my own. I took her shirt off and started kissing her neck and chest, while removing my own shirt and reaching around to take off her bra. When those beautiful breasts were exposed I almost came in my pants. They were so firm and soft and had the hardest nipples I’ve seen in my life. My mouth moved immediately towards them and I began to suck on one while tweaking the other. I could tell she enjoyed this very much from her screams of ecstacy. Without notice, she flipped me over on to my back and began sucking on my nipples. I had never considered this before but must admit that it felt amazing. She kissed down my chest and stomach until she reached my pants. She undid the button of my jeans and pulled them down along with my boxers. My 7 inch cock sprang upwards almost hitting her face. She grabbed by cock and began to stroke it while kissing and licking the head.
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When she started sucking it fully, she was also rubbing my balls and putting her finger around my asshole. This came as a total surprise. I was experiencing so many sensations at one time. Her hot, wet mouth around my cock and the pressure she was applying to my asshole was putting me way over the edge. I knew I couldn’t hold back much longer. "Oh my God! I’m gonna cum. . . oh. . . suck my dick!. . . That feels so fucking good.
" At that moment I came into her mouth. She swallowed it all down with a satisfied "mmm" following. But I was worried that because I already came, I wouldn’t have any strength to have sex. "Don’t worry," she told me, "Just give me what I need and we can see what happens from there. " I happily obliged.
She sat down next to me and we made out again while I unbuttoned her pants. I slid my hand through her panties and played with her pussy. I had never done this before, but since she seemed to enjoy it, I could tell I was doing something right.
I pulled my hand out and she licked my finger, tasting her own juices. I could already feel my cock growing again. I removed her pants along with her panties and got my first look at her pussy. She was completely shaved, had no tan lines, and the juices flowing from her pussy made it glisten. It was the perfect sight. I kissed my way down her legs until I reached her sweet mound. I leaned in and started kissing the outside of her lips.
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I then stuck my tongue in and went to work. The taste was different but wonderful. I had heard nasty things about how pussies smell and taste, but in the moment, it was the best thing I had ever experienced in those departments. Knowing from science class where and what the clitoris is, I started to suck and bit the tiny organ. She started lifting her ass and smacking her pussy against my face. She was practically screaming at the top of her lungs. Only moments later, her pussy erupted with juices. There was so much fluid I could barley contain it in my mouth. I sprayed everywhere. "How did that happen?" I asked her. "Oh, I forgot to tell you. . . I’m a squirter. " This turned me on even more.
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I couldn’t wait to get inside that hot, wet pussy. But first I turned her over onto her stomach and played with her ass. It was so round and firm, and her asshole had a beautiful pink colour. I moved my mouth forward and started licking her asshole. "That feels so fucking good! Suck my asshole. I’m gonna fucking cum all over your face again!" All that dirty talk really got me going. I stuck my finger in her pussy while I continued to lick her ass. This made her go wild and she came again, this one even more explosive than the last. She appeared to be exhausted, but I was feeling like my dick was going to explode. I had go get inside of her.
I asked her if I needed to put on a condom and she said that she was on the pill. I climbed up through her legs and licked her tits again while slowly fingering her pussy. This got her pretty worked up again so I decided to take the plunge. I grabbed hold of my dick and placed it at the entrance of her hot cunt. I rubbed the head of my dick up and down her slit before I put it in.
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I was amazed at how warm and tight it was. I slowly began to thrust myself deeper into her pussy and she responded by thrusting back. I laid on top of her, crushing her tits against my chest and giving her long deep kisses. After 5 minutes of amazing sex, Emily asked me to do something for her. "Alex. . . could you suck my toes while you fuck me?" she asked timidly, "Of course honey. Anything for you. " I lifted my body up, with my dick still inside her, and moved her legs so that they were on my chest. With her feet in front of my face, I grabbed one and began sucking on her toes. It felt so erotic sucking her feet while fucking her pussy. Her toes tasted so good and her pussy was so hot. . .
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but I couldn’t come. . . I wouldn’t allow myself. I wanted this to last as long as possible. I lifted her body and flipped myself over so she was on top of me. "Now it’s time for you to do some work. " I said to her, "I thought this was a learning experience for you. " she replied, "Just shut up and fuck me!" And she did just that. I lay on my back and she rode me like a bull. As she did this, I roughly rubbed her nipples and tits. This looked like it was going to be the end for me. I sat up and wrapped my arms around her while quickly humping her pussy. I lifted my head and looked into her eyes. I loved this girl, and the way she looked at me, I knew she felt the same.
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At that instant, I came inside of her. I was the longest and hardest I had ever came and has been till this day. I lay back down with her laying on my chest. I caressed her back and ass, and she gave me a deep long kiss.
"How was that. " I asked her.
"I think your ready for Caroline. . . I’m just not sure she’s ready for you!"
End of Part 1
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