Teen
2008-05-16

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 I’m a 18-year-old senior in a Toronto high school. I’m 5'11 and around 180 lbs (mostly muscle) with brown eyes and brown hair.

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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. You see, I have this very close friend.

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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. Along with her personality, she also is very attractive.

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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 the courage to bring up the reason I needed to see her. Then, without knowing, she brought it up herself.

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“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… well. .

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. 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.

“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. .

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. 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. It 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. 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.

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”

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. 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.

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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 ecstasy. 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. 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.

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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. 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.

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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. 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.

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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. 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. . .

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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. . . 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.

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” 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. At that instant, I came inside of her. It was the longest and hardest I had ever came and has been till this day. I lay back down with her lying 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 you’re ready for Caroline. .

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. I’m just not sure she’s ready for you!”

Chapter 3 - The Surprise

My night with Caroline was coming up with thoughts of my session with Emily fresh in my mind. I wanted to have another go with her before this weekend but there was never a good time. It’s not like I needed more practice, the way I made Emily scream in pleasure was reassuring enough. I was just dying to get into her tight pussy again. Feeling her warm fuck-hole tighten up as I slowly pushed inside of her. . . but I needed to get my mind straight.
I forgot to mention that Caroline had been away for the whole week on vacation with her parents and was returning without them because she had work Saturday morning. Just incase you were wondering where she was all this time. Well, it was the morning of that special day, and I had slept in so I had strength for that night. I even jerked off to make sure I didn’t shoot my load too soon. I had just finished up when my cell phone rang. It was Caroline.

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“Hey baby. ” I said answering the phone.

“Hey hot stuff! I’ve been thinking about you all week. I’ve missed you so much. ”

“ Me too hunny. Are you ready for tonight?” I asked.

“I am so ready for this. I can’t wait! Are you ready?” she asked back.

“I guess you could say I’ve been preparing. ” I answered with a smile on my face.

“Sounds great. I need to head off to work. . . so I’ll see you at 7?”

“I wouldn’t miss it for the world.

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” I hung up the phone and went to take a shower.

I stepped out of the shower and began shaving my face when I heard the doorbell ring. I threw a towel around my waist and ran downstairs expecting it to be my mom and sister who were out shopping for the day. But they weren’t supposed to be back for at least another hour. I opened the door and was pleasantly surprised at what I saw. It was my little sister’s friend Stephanie. Now, I’m usually not one to go for younger girls, but this one was a 18-year-old bombshell. Her long brown hair framed her perfect face and fell down towards her young perky breasts. She was pretty short at 5'4 but had a sweet little ass. She was wearing a low cut tank top and a short skirt. Trying to conceal my growing erection wasn’t easy.

“Hi Alex, is Jennifer here?” she asked with the sweetest smile on her face.

“Sorry Steph, she’s out shopping with our mom. She won’t be back for around an hour. ”

“Oh, I see.

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Would you mind if I waited here for her?” as she asked, I could see her eyes moving up and down my body and linger slightly at my crotch.

“Ya, no problem. Just make yourself comfortable. You know where everything is. I just need to finish up upstairs. I’ll be back down in 18 minutes. ”

“Okay. . . ” she called as I walked up the stairs.

Oh man, this girl is so fucking hot. I would do anything to get inside of her. I thought to myself as I began shaving the rest of my face. I looked down at my crotch and decided it would be good if I did a little trimming down there. I applied shaving cream to my parts and began shaving them.

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I was pretty worked up over Steph, so my dick was at full attention, which makes it a bit harder to shave. When I finished, I moved over to the bathtub to wash the hair off when I noticed the door was opened slightly. I quickly flew the door open and there was Stephanie, falling to the floor with her hands up her skirt. I couldn’t believe what I was seeing. This hot little thing was finger fucking herself while watching me shave my balls.

“Oh my god! I’m so sorry Alex! I couldn’t help myself. When I saw you in that towel, you made my pussy so wet. I had to get a look at your dick. ” she was speaking so fast I could barley make out the words. Her face was completely red and I couldn’t tell if that was from shame or because she was just masturbating. I walked over to her, picked her up off the floor and sat her down on the edge of the bathtub.

“Don’t worry about it Steph. I can understand you being curious. At your age, I would have done anything to see a pair of tits. ”

“So you’re not mad at me?” she asked.

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“Of course not. It would be kinda hypocritical of me considering the fact that I’ve thought about you when I’ve masturbated. ” I admitted.

“Are you serious? That makes me so happy. ” as she said this, she reached over and placed her hand on my dick. The fun was about to start.

Chapter 4 – The

Her small hands barely fit around my thick cock, but she was jerking like a pro in no time. She told me she had never touched a dick before and wasn’t sure if what she was doing was right. Feeling a little devious, I told her I would enjoy it much more if she used her mouth. She didn’t seem opposed to this idea and put her mouth right on my dick. Her mouth was quite small so she couldn’t fit much in, but it felt amazing nonetheless. As we progressed, she began to develop a technique without much guidance. She was sucking on the head, stroking the shaft and rubbing my balls at the same time. She then moved her hand away from my balls and dived into her pussy. I removed her top so I could see those sweet tits as she sucked me off.

I pinched her nipples, and rubbed her back and ass. She was furiously fingering herself, which in turn made her suck and stroke harder. It was all too much for me to take and I came in her mouth. She was taken by surprise and released my dick from her grip, which left me jerking off on her tits and stomach. With her little finger, she grabbed some cum off her chest and put it in her mouth.

“Wow Steph, that was unbelievable. Any man would be lucky to have a sex toy like you. ” I said totally exhausted.

“That man is you. Anytime you want me, you can have me. ”

These words drove me wild. “Then I am the luckiest man in the world. What do you say we get you cleaned up. ”

I reached over and turned on the shower so we could wash off. When the water was hot enough, we both jumped in.

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I grabbed the soap and started lathering up her body. Her back was pressed up against my chest and I slowly rubber her tits. Her skin and the hot water felt so good against my body, my cock started to stir. I turned her around and placed my hands on her cheeks. She was absolutely beautiful. I leaned in and kissed her lips softly. She returned by slipping her tongue into my mouth. As we kissed, I fingered her pussy getting her excited again. She dropped to her knees and placed my cock between her tits and started jerking me off. It had to have been the sexiest sight I have ever seen. This hot, young, skank was rubbing my cock all over her perky tits. It was almost too much to take but I knew I had to get something else from her. I lifted her up into my arms and told her to wrap her arms around my neck and her legs around my waist. My dick was just at the entrance of her hot, little cunt. They way she looked at me I could tell she was ready to lose her virginity.

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“This is going to hurt. ” I said. I pushed her against the shower wall, our lips met, and my dick pushed through her pussy taking away her innocence. She let out a terrible scream and bit on my shoulder. I held her close and told her that the pain will be gone and pleasure will follow. After about a minute of holding that position, she started to get used to the size of my invading cock. She was actually the one who began slowly humping. I was hitting her with long, full thrusts, and the look of pure joy washed over her face. I put my hands under her ass for support and fucked the life into this girl. I had never heard someone scream that loud before. It felt like she had 3 orgasms in 5 minutes.
I pulled her off my cock so I could try something I had always wanted to do. I turned her around and bent her over so her ass was facing me. I got down on my knees and started eating out her asshole. I could tell she loved this when her hands went right for her clit.

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I was roughly grabbing her ass cheeks and sucking on that tight little hole for so long, I forgot that I hadn’t shot my load yet. I stood up with her still facing the other way and put my dick back in her pussy. She lifted her torso up so her back was against my chest, which gave me easy access to her tits and clit. I fucked her fast and rough while biting on her neck until I knew I had to cum. Realizing I didn’t have a condom on, I pulled out, turned her around, and put my cock in her mouth. I knew she had learned something from our fuckfest when I started cumming, and she took it all in her mouth. She stood up, swallowed it down, and gave me a long passionate kiss. I turned off the water and helped her out of the shower. We dried each other off and got dressed.

“This was the most amazing experience I have ever had. ” She said.

“It was amazing for me too. I’ll never forget it. ”

Just then, I heard the front door open. Steph rushed down to the family room and I waited at the top of the stairs as my mom and sister walked through the door.

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Steph came running from the family room and gave my sister a hug. My sister asked why her hair was wet and she replied by saying, “I was feeling kinda dirty. ” She looked up at me, gave me a wink and I went back into my room to prepare for my big night. . . which didn’t seem so big anymore.

*Warning - Contains Incest

Chapter 5 - The Intrigue

It was 6:00 and I needed to leave my house to pick up Caroline from work in an hour, but first I had to convince my mom to let me take out the car overnight. There was no way in hell I was going to tell her I was staying over at Caroline’s house. She would have smacked me upside the head and swallowed the car keys. This was going to be tricky. I walked into the kitchen and my mom was sitting there reading a magazine.

“Hey mom. . . would it be ok if a took the car out tonight?”

“Sure hun, I’m not planning on going anywhere.

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” she replied with a smile.

“The thing is. . . I won’t be home until tomorrow. ”

“Well where are you going?” she asked, becoming slightly suspicious.

“Uh. . . I’m staying over at Kevin’s house. There’s a fight on and he’s the only guy with pay per view. The fight won’t end till late so we were planning on crashing there. ” That should do the trick. I thought confidently.

“You know son, I’m not an idiot.

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I know you’re going to stay over at Caroline’s while her parents are gone. Were you planning on fucking her tonight?”

I couldn’t believe my ears! Not only did my mom know exactly what was going on, she also knew that we were gonna have sex!

“Mom. . . how. . . . where did you get that idea?” She stood up and walked towards me.

“Like I said hun, I’m not an idiot. If you want these car keys, you’re gonna have to work for them. ”

Let me take a minute to tell you about my mother. When I was 10, my father left my mom, my sister, and me for some old high school sweetheart. I couldn’t understand what kind of person would leave my mom for someone else. She was absolutely stunning.

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She was 5'8, had long black hair, piercing blue eyes, and large, succulent lips. She kinda resembled Angelina Jolie with a body to match. She had large, firm D cup tits (I knew this from searching through her drawers), a slim waist, and a small, tight ass. I had always fantasized about my mom while going through puberty, and that trend has not stopped. My mom worked so hard to provide for my sister and me. I only ever wanted her to be happy. So there I was. My MILF of a mom looking me in the eyes with pure lust. I did the only thing that seemed natural to do at the time. I shoved my tongue down her throat.
This wasn’t a kiss of love. It was raw, animalistic, and purely sexual. I lifted her on to our kitchen table so I could get inside that pussy with my tongue. She was wearing a bathrobe with nothing underneath, so I had easy access. I pulled on the rope around her waist to reveal the sweetest tits and fattest pussy I had ever seen.

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She had most of her pussy shaved, with a small line leading from her clit. I dove right into her with my tongue and got pussy juice all over my face. She tasted so much different than Emily did, and the smell was a lot stronger. But this only turned me on more. I started fingering her while rubbing her clit. I almost fit my whole fist in her pussy. I flipped her over and continued to eat her out doggy style. I then moved from her pussy to her asshole. I sucked on her hole and fisted her wet cunt. This made my dick pop out of the top of my pants. I was ready for some relief. Once she was nice and wet down there, I decided it was my turn to get some action. I walked around the table so I was facing her head. I flipped her on to her back and let her head fall off the back of the table. I slipped off my pants and shoved my cock down her throat.

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I had no mercy for her as I grabbed the back of her head and skull fucked the life out of her. I thought for sure she would start choking, but she swallowed me whole. I could feel the head of my dick hitting the back of her throat. I had started sucking her nipples and rubbing her clit when I got that familiar feeling in my dick so I pulled out of her mouth, got behind her, and placed my dick at the entrance of her pussy.
"No baby, you can't fuck mommy there. It would be too wrong. "

Too wrong? Just great. I was so close to getting inside of her and she pulls this bullshit on me. I can't believe sh. . . .

"You'd better stick it in my ass. "

. .

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. things couldn’t get any better. I was about to give a girl my first ass pounding and it was my own mom. Life kept getting better and better. I moved my dick from her pussy to her ass and rubbed it against her hole. It was so small. I didn’t think I could fit it in. I got up and headed for the cupboard and grabbed a bottle of baby oil. I got back on the table, applied it to my mom’s asshole and to my dick, and worked my way inside her. I humped her as slowly as I could so she could get used to the invading member in her ass. She started to moan as I pushed in and out quicker and quicker. As we started to get into a rhythm, we got the shock of our lives. Standing in the doorway was my little sister.

Jennifer is a 18-year-old replica of my mother. She has the jet-black hair, which she always wears in a ponytail, blue eyes and a well-developed chest and ass (I would say she’s a large C cup).

She’s quite tall for a 18 year old at 5'10 (we both got our height from our father). She started to really develop at the age of 18 and now she is the fantasy of every guy at our school, including myself. Seeing her stand there in shock got me even hornier. I continued to pound away at my mom’s ass leaving Jen there to figure out what was going on. The tight grip of her ass on my dick, and my sister standing there, was a lethal combination and I soon shot my load straight up her ass. I collapsed on top of her for a minute trying to catch my breath. My sister still hadn’t moved a muscle but when I looked at her closely I could see that her nipples were erect under her tank top. Could my sister really be getting off to watching me fuck our mom in the ass? I thought to myself. I pulled my dick out of her ass and watched the cum flow out. My mom quickly stood up and put on her bathrobe.

“Jennifer dear,” my mom said, “let us explain what happened here. ” But Jen didn’t want to hear it. She turned around and walked up the stairs to her room. “Oh no. I better go talk to her.

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”

“No, let me mom. I know what to say. ” I walked up the stairs to her bedroom door when I realized I was still completely naked. I went into my room first and grabbed a pair of boxers and a t-shirt and walked back to her door. I didn’t bother knocking and just walked in. And what did I see? My little sister naked on her bed with 3 fingers in her pussy. My dick popped up like a jack-in-the-box. She looked over at me, smiled, and motioned for me to join her. This was all the incentive I needed. I pulled off my shirt and boxers and jumped into her bed.

“Oh Jen. . . I’ve wanted this for so long. ”

“Me too Alex.

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. . now lets fuck!”

I got on top of her and we started kissing while discovering each other’s bodies. I squeezed her beautiful breasts and pinched her long nipples.

I had never seen nipples so erect. They felt great rubbing against my chest. I took my mouth away from hers and sucked on her tits. She started to moan really loudly and I could feel the heat from her pussy on my dick, which was right in front of it. She pulled my head away from her tit, looked into my eyes and said “I want you to take me right now. ” Without taking my eyes off hers, I guided my dick into her wet pussy. I felt some resistance and could tell she was still a virgin. I couldn’t believe this. A girl this hot still hadn’t had sex. I was in heaven. I slowly started rubbing her clit making her more comfortable with my dick inside of her.

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I then shoved my full member into her tight cunt. But she barely let out a whimper. She just kept looking right into my eyes, never even blinking. I slowly started to pick up the pace and in no time I was giving her full thrusts. She started to moan and groan and dug her nails into my back. She wrapped her legs around me and started to hump back, meeting me at full thrust. She had a beautiful patch of hair on her pussy that felt wonderful against my shaved pelvis. I looked over at the clock and saw that it was 5 to 7 and I needed to pick up Caroline from work, so I started humping her as fast as I could. Her screams became louder and I was sent into a state of pure ecstasy as I shot load after load into her virgin cunt. I pulled out of her and laid down next to her. “Sorry Jen, but I need to pick up Caroline from work. ” She looked at me with sad eyes and replied, “At least let me clean you up first. ” She lifted up my limp dick and started sucking and licking off my cum and her juices. Within seconds my dick was a rock. She started to use her hands while sucking me to allow me to have the full experience.

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She then grabbed her tits, put them around my cock and jerked me off with them. She somehow managed to suck on it at the same time. It felt so amazing. I shot my second load of our session right in her face and it fell on her tits. She picked it up with her finger and rubbed it on her nipples and on her lips. This bitch really loves the cum. I gave her a kiss on the lips and told her that we would do this again soon but I needed to leave. After another quick kiss, I ran into my bedroom, threw on some nice clothes, ran down stairs, gave my mom a slap on the ass, and went to pick up Caroline for our date.

Chapter 5 - The Date

As I was driving down to the mall to pick up Cali (that was my nickname for her because she was in love with California), my mind started to wonder. What would Caroline think if she found out the things I have done in the past week? Since we had talked about losing our virginity together, I had already had sex with her, and my, best friend Emily, my sisters little friend Stephanie, my hot mom, and my even hotter sister. I had done all these things without even considering how Cali would feel if she found out. At the beginning I had convinced myself that I was doing those things for her benefit, but in reality, it was my own perverse mind that led me to cheating on her over and over. But I decided that what happened in the past should stay in the past. . .

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. even though I planned on fucking all those girls again. There was no need for Caroline to know about it.

I drove up to the mall entrance and Cali was standing there waiting for me. Her slender body looked magnificent with her white blouse, short, black skirt, stockings and high heels. But I couldn’t wait to take them all off.

“ Hi baby!” she exclaimed as she crawled into the car. I gave her a long kiss on the lips and replied,

“ You look so beautiful. . . ” I handed her a bouquet of roses, and she blushed and said thank you. “I made reservations at Dante’s for 7:30 so we need to get moving. . . are we still going back to your place tonight.

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. . ?” I asked.

“You know it!” she replied with a mischievous smile.

We arrived at Dante’s at 7:15 and we were seated by 7:20. Dante’s was our favourite restaurant. All they served was authentic Italian food and the portions were huge. Once we were seated, we ordered out food and started chatting about our week. As I stated before, I was not about to tell Cali what I had really done all week so I lied my ass off. I told her I mostly stayed in my room thinking about her and counting down the minutes until I could see her again. Her heart melted over this and told me I was the sweetest guy in the world. Suddenly I felt something moving up my leg. I looked at Cali and she was smiling at me. It was her foot. She kicked off her shoes and started to rub my inner thigh.

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This got my dick hard as a rock. I had never seen her acting like this. I decided to take in a step further and undid my pants. Since the tablecloth almost reached the floor, we had total privacy. With her nylon covered feet, she pulled down the elastic on my boxers and started to massage my cock. They feeling of the material on my skin was amazing. She managed to get a full grip on my dick with both her feet and slowly began jerking my off. I couldn’t believe what was happening. My mostly timid girlfriend was fucking me with her feet in a public place. I had to shoot my load and she knew it, so she started to jerk faster and faster. I shot load after load of cum on the bottom of the table, the floor, and Cali’s feet and legs. I let out a groan and some people looked over, but they didn’t suspect anything. We kept the dinner talk to a minimum and ate quickly, knowing perfectly well what was going to happen after dinner.

We finished up, I paid the check and we were off to her house. The drive back seemed like hours long, when in reality it was only 18 minutes.

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We walked into her house and, wasting no time, walked upstairs. We got to her door but she told me to wait outside until she was ready. I wasn’t going to argue so patiently waited outside her door until she told me to go in. When I walked in, I saw the most beautiful sight. The entire room was filled with lit candles, there were two glasses of Champaign on her dresser, and my gorgeous girlfriend was lying on her bed in her bra and panties. She sat up and walked towards me. She was still wearing her stockings and heels, which turned me on a lot. She gave me a long kiss and told me to sit on the bed. She grabbed the Champaign glasses, handed one to me and we toasted to a perfect night. We put the glasses down and I immediately started kissing her ears and neck (which always drove her wild). Meanwhile, she was reaching under my shirt and rubbing my chest. I ripped my shirt off and started working on her bra. When I got it open, I was struck by the sight on two perfectly formed breasts topped with the pinkest nipples. They really got my blood pumping. I slowly kissed down her chest until I reached her erect nipples.

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I gave them each a small kiss and she let out a small whimper.

I gave her another kiss on her lips and got to my knees so I could kiss her other lips. I slowly pulled down her lacy panties and revealed a small pink pussy with a small patch of very blonde pubic hair. I started kissing her inner thigh and around her pubs until I saw her pussy start to moisten. I gently gave her lips and clit a kiss and she pushed her mound right against my face. She was getting pretty horny, so I took my tongue and slowly, but firmly, lapped up her juices. I started to move faster and rubbed her clit with my finger. She started to moan and breath very heavily. I knew her first orgasm was about to hit. With my other hand I stuck my finger in her pussy and finger fucked her while eating her out. Her pussy was so tight my finger felt resistance. She started to buck her hips and scream in pleasure for what seemed like five minutes.

She sat up, got me off my knees and kissed me so she could taste her own juices. She rolled me over onto the bed and stood up facing me. She reached down to take off her heels and stockings but I stopped her.

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“No baby, keep them on. They turn me on so much. ” She obeyed me and climbed on the bed next to me.

“You wanna try something fun?” she asked.

“I’ll do anything you want beautiful. ” I replied and kissed her cheek.

She turned her body around so I was facing her rear and sat on my face. I happily went to work on her pussy thinking nothing of it. Then I felt her bend over and slip off my pants. When she pulled down my boxers, my dick sprang up and hit her in the face. “Are you alright?” I asked her almost laughing. “Just keep eating. ” she said, half laughing herself. I began licking again when I felt a then familiar sensation on my dick. It was of course her tongue.

She made slow, soft circles around the head of my cock and licked the length of my shaft. I then felt her take my whole dick into her mouth and suck on it like a vacuum. Her hot mouth took most of my dick all the way. This was very surprising to me because I knew she had never done it before. While she was sucking me off, I started to play with her ass. I was rubbing and massaging her cheeks and at times, ran my finger over her asshole. I received positive reactions every time I did this so I decided to put my entire finger in her ass. I could hear her start to moan while my cock was still in her mouth. More and more juices started to flow out of her and I could tell she was reaching an orgasm. I fingered her asshole with full force and she began humping my face again. When she started to orgasm, she was still able to keep my dick in her mouth. The juices flowing on my face and tight suction on my dick made me shoot a huge load into her mouth. As soon as we both finished cumming, I realized that she had never experienced a male ejaculation before and must have been seriously surprised. She slowly got off my face and turned towards me. I could see the cum dripping from her lips and chin.

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Just when I was about to explain, she leaned in and kissed me. Having to taste some of my own cum wasn’t something I wanted to do, but I wasn’t about to stop her from kissing me. As we kissed, I softly caressed her body, rubbing my hands over her smooth, silky skin. I lifted myself up and put her flat against the bed. With one hand I played with her tits, and I played with her pussy with the other one. I was ready to give it to her and by the amount of juices flowing out of her, I could tell she was too.

I grabbed hold of my cock and rubbed the head up and down her slit to get it covered in juices. Instead of shoving it in her pussy, I kept teasing her by slapping my dick hard against her clit. By this time she couldn’t take anymore, so she grabbed my cock with one hand and my ass with the other, and pulled me into her. My dick sunk in easily until I felt some resistance. I laid myself down on top of her and kissed her lips in an attempt to distract her from the pain she was about to experience. She looked into my eyes with a stare that told me she was ready. As we kissed, I pushed my dick as far inside of her as I could. To my surprise, she did not scream. A single tear fell down her cheek, which I quickly kissed away, but no scream.

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She just smiled and nodded at me. I pulled my cock half way out and hit her with another long, deep thrust. She closed her eyes and started to fell the pleasure that follows. She wrapped her legs around me and I started to pick up the pace. She began moaning with satisfaction and meeting my thrusts with her own. I quickly grabbed her and turned myself over so she was on top. Without hesitation, she placed her hands on my chest and dropped down hard on my cock. I started to massage her gorgeous ass and played with her curly blonde pubic hair. She kept on riding me without slowing down the pace for even one second. To see just how far she was willing to go, I inserted a finger into her asshole. To my pleasant surprise, she let out a long moan and continued to ride me like a bull, so I continued to finger her ass. At that point I really wanted to see her ass in action so I told her to stop and face the other way. She quickly did so and soon I was watching a beautiful ass bounce up and down my dick. I sat up so her back was against my chest and reached around to find her tits. I pinched her hard nipples and then reached down to find her clit.

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I could feel her orgasm, as well as mine, quickly approaching. I rubbed her clit without mercy until I felt her pussy turn into a vice. As this happened, I began to cum inside of her (Cali decided to take the pill a while ago so a condom wasn’t necessary. . . even though I still should have worn one). I laid down on the bed with her body on top of me. Both of us were sweating and breathing very hard, and my head was spinning. I softly placed her next to me pulled my dick out of her. I watched as my cum leaked out of her swollen cunt. I looked at Caroline, she looked at me, and we both smiled at each other, and fell asleep in each other’s arms.

The End. . .
.