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Introduction:

A true story about my first experience about the first woman I ever loved.
Jessica~

This is a true story that happened a while back to me. I really felt like getting it out and hopefully you guys like it. Everything is true, except the names are changed as I do not want the real identities to be revealed. The story of course isn’t word for word true, I couldn’t remember all of it. There was more time in between the events that I wrote about, but I didn't include that time because there wasn't a lot of sex in those times and you guys would get bored. It's a pretty short story and it's not really mindless sex, it’s got more of a story to it. So if your going to leave comments about “more sex0rz” just leave now. Enjoy.

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My name is Alex and I am 16 years old and starting my sophomore year at high-school in Ann Arbor, Michigan. I am about 6 feet tall, brown hair and blue eyes. Pretty average build, I played soccer in school. I’ve got nearly a 7 inch dick, so I suppose that’s alright. I am still a virgin and the furthest I had gone sexually was when I had oral sex with from my ex-girlfriend in my freshman year. I always had a crush on one of my sister’s best friends, Jessica.

Jessica. In my eyes she was the most beautiful girl who ever walked this Earth. She was just so pretty, she had long blonde hair and blue eyes, was only probably about 5 foot 5 inches, and had pretty average 32B breasts. I don’t really think she had much of a thing for me at all, nothing more than a smile when she came over to my house or something but damn I always thought she was beautiful. Like I said, it didn’t seem she paid much attention to me until things finally started looking up.

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My sister Jenny was having a few of her friends, including Jessica, and a few of her guy friends over as she does every Friday night, and I had one of my friends Zach over as well. My sister is just a year older than me and one grade above me. Zach and I were downstairs playing Foosball when my sister and her entourage arrived. They all headed downstairs to watch a movie. I didn’t see Jessica and it seemed odd at first but then I saw her coming downstairs with a soda. As she walked past me she just looked at me and said “Hi Alex!” I said hi and she just continued on by to our family room to join everyone else. Zach just looked at me and laughed because he knew I liked Jessica. I punched him in the arm and told him to shut up. He punched me back and said he had to go home for dinner. So I bid him farewell as a grabbed a blanket (my basement was cold) and I went into the family room to join them in watching Saw.

Everyone there was paired up with someone cuddled up in a blanket watching and
enjoying the movie. That is except for me and Jessica. It was kind of awkward and all, just us two sitting by ourselves and everyone else paired up. Our eyes met a few times, again, quite awkward, but I didn’t pay much attention to it. I was pretty sure Jessica knew of my affection for her but I wasn’t sure if she liked me at all or thought I was just an annoying little brother of her best friend. Andrew, one of my sisters guy-friends and also one of mine, noticed Jessica didn’t have a blanket and I was sitting by myself. He knew I liked her too so just to piss me off he says, “Jessica go sit by Alex you look cold and he has a blanket you know.” I glared at him and he just gave me that dumb grin of his. So Jessica got up and walked over to me and I generously gave her over half of my blanket, not wanting to seem rude. We were right next to each other for quite a while, just watching the movie. I was already getting a hard-on just from being so close to her. Thank god for that blanket and the dim lights otherwise that could be pretty embarrassing. The movie was getting to a scary part and I knew Jessica was never for watching many scary movies. She hugged my arm, brushing against my thigh getting my junk even more excited.
I didn’t have to suffer long as she began to doze off and she just rested her head
on my shoulder.

Everyone got up and said they were going to go for a walk, even though the movie wasn’t even half over. I didn’t join them as I didn’t want to wake Jessica. So there it was just the two of us down in a dark basement. Awkward, yes? I started to get up trying not to wake her but she make little grunts and slowly awoke. Jessica woke up and looked around and asked me where they went. She was still hugged around my arm and I simply replied, “They went for a walk but I didn’t want to wake you, sorry if you wanted to go with them…” She giggled and looked at me and said “Aww that’s so sweet of you” She just smiled at me. There was a moment of silence and something told me to do it… I leaned in a kissed her gently and she kissed me back. I put my hand behind her head and on her lower back as we kissed. Our tongues danced around each other and I swear her hand brushed against my hard-on a few times. Sadly this heaven did not last long as the others were returning. I reluctantly pulled back and looked into her blue eyes… That was one of the best moments of my life and I will never forget it. Jessica just smiled at me and sat back up as everyone else settled back down to finish the movie. Andrew looked at me and winked.

The rest of the movie was pretty uneventful for me and Jessica, she just sat next to me and I had my arm around her, my hard-on still going as strong as ever. Thank god, my boner had calmed down as people started to leave when the movie was finished. I got up and walked to the door with everyone saying goodbye and talking for a few minutes. I walked over to Jessica and said bye, she smiled and me and gave me a peck on the cheek. As soon as the door closed I casually walked into my bedroom and closed and locked the door. Having a boner for two hours can take it’s toll on a man… I slowly stroked my not too large seven inch cock. Climax couldn’t “come” soon enough. God that was one of the best orgasms of my life. Bet you couldn’t guess what my thoughts were on…

I wasn’t really sure what would happen from then on because Jessica was my sister’s friend after all and that could be weird for her. I mustered up the confidence to call her Sunday night. We talked for probably 3 hours about all sorts of things. I told her I’d see her tomorrow and slowly hung up the phone. I took a big breath and finally realized my fantasies were coming true.

The next day I couldn’t wait for school. I only had one class with Jessica, which was Chemistry, which was 4th period. Fourth period is the last period of the day and the day was soooo damn long. I rushed to chemistry after 3rd block. I was the first one in the room, the teacher just gave me a strange look for being there so fast. After about five minutes Jessica walked in and sat down next to me. We didn’t get much of a chance to talk but she told me to stop by her locker after school. I quite nearly ran to her locker after dropping my books off at my own. I was greeted with a “Hey stud!” I just laughed and said hey. She invited me over to her house that night. I probably took 30 minutes getting ready (that’s a ton of time for me, who doesn’t usually “get ready” at all, I just walk out the door).

I walked over to her house since she didn’t live too far away and rang the doorbell. Jessica was there immediately and told me that her parents weren’t home and invited me up to her room for a movie. We sat down on the couch in there and popped in a movie. I put my arm around her and leaned in on me. After a while she laid down and put her head on my lap, which was just calling to get poked. I resisted sooo much not to get excited but god damn my teenage hormones within three minutes I was at full mast, I absolutely had to be poking her in the head. She giggled a little and I felt my face get red. “W-What are you laughing at…?” Jessica burst out laughing at how nervous I was. “Why you so nervous? It’s not like I’ve never met a 16 year old guy before.” That relaxed me a little. Then what she did next totally surprised me. “Well lets see what we’ve got down here anyways while he’s here!”
Well I wasn’t going to deny her so I said, “Go ahead no ones gonna stop you.” She slowly unzipped my pants and looking at my dick stretching the fabric of my boxers. As she slowly slid my boxers down, I lifted my butt up to let her get them down. My seven inch dick was going down with my boxers and suddenly sprang up into her face, at full attention. “Ooo what do we have here?” Jessica asked playfully. She grabbed me with both hands and spit on my cock. She slowly started pumping it and then fully engulfed me in her warm wet mouth. “Ooo Jessica that feels so good” I said, in a slow voice. “Oh I bet it does big guy.” Jessica giggled. She continued to bob up and down on my dick for a while and then got up. I was about to question her when she stripped off all her clothes, so I joined her in doing so and then she continued with her business. I could feel her tongue exploring every inch of my dick. “I’m about to come Jessica… are you sure you want it in your mouth?” I asked. I heard no response so I just closed my eyes and put my head back and enjoyed it. I heard soft slurping noises and grunts from her as she sped up. I could hold it no more so I let it go. “Oh shit Jessica don’t stop!” She picked up the pace even more until I was done, she didn’t swallow it but she licked up every last drop before she was done with me. “Your turn” she said. My turn. Sounds good to me!

We switched positions on the couch, she laid on the couch with her legs spread and that beautiful wet shaved pussy in my face. I put a finger in her and right away she said “Are you kidding?! Put two in.” I looked at her for a second, hesitant, then I complied and put another in. I slowly finger fucked her and listened to the noises she was making. I felt her pussy starting to tighten so I pulled my fingers out and dove in with my tongue. Jessica put her legs on my shoulders and pushed my head in with both hands as I tongue fucked her. Boy did she come fast and hard. “FUCK ALEX! FUCK!” She had quite a long orgasm from what I could tell and when she was done I slurped up every last bit of that sweet pussy juice. She slowly opened her eyes and just looked at me. I got up and kissed her more passionately that I’ve ever kissed anyone before. We heard the garage door opening downstairs. She told me I had to get out before her parents found her and I told her I would call her. I ran downstairs and left through the back door. I walked home trying to register what had just happened in my mind. I got home and immediately called her. I asked her what happened when they got home and she said “Nothing, they just thought it was weird that I was home, usually I'd be out with someone heh.” She asked me if I wanted to skip school with her tomorrow so we could be together. “Is that a rhetorical question Jessica? Of course I would.”We talked for a bit longer and then I hung up, knowing tomorrow would be an awesome day.

I couldn’t get to sleep for some time because I just couldn’t go to sleep I was just so madly in love with this woman. I was nearly asleep when I heard a tap on the window. I opened the blinds and I saw Jessica standing there. I whispered “What are you doing!” but of course she couldn’t hear me, the windows were closed. I opened the front door quietly and stepped outside, shutting the door behind me. Jessica was wearing a tight pink shirt, I could see her tits quite easily, and short yellow gym shorts. I asked her what the hell she was doing and she just told me she had to see me. “Do you want to hang out for a bit?” she asked. I looked at her. “Are you crazy? I’m not supposed to be out now!” I was a bit dumbfounded… “Just a little” she said laughing. She grabbed my hand and we just went for a short walk.

I took her to the golf course nearby and we laid down on the 15th fairway (I don’t know why I remember what hole it was, but it sticks out in my mind) and looked at the stars. A lot happened. She talked to me and told me she always sort of had a thing for me since the 8th grade, and that she wished this would have happened sooner. I told her I’d always liked her as long as I could remember. We sat in silence for a moment, looking at each other. “I love you Alex.” Wow. “I love you too Jessica.” Again, it was one of the happiest moments of my life. We talked for a long time before we started to get… personal. Jessica rolled over on her side and put her hand on my crotch, which already had an erect penis there. She laughed and said “Are you never not hard?” I said, “Once in a blue moon.” She glanced over at the moon and said “Looks like that’s not tonight. Lucky me” She grinned. I took her shirt and shorts off, she wasn’t wearing and under-garments fortunately for me. She did the same to me, I told her to wait for a second and grabbed the condom out of my pocket and told her to continue. I put the condom on and rolled on the top of her. I looked her in the eyes and told her “I’ve been waiting too long for this” She grabbed my ass cheeks and pulled me in. She wasn’t a virgin, which wasn’t a surprise I guess. I told her I was and I felt a little embarrassed but she said it doesn’t matter, "I think you know what to do." She winked at me. I started pumping in and out, slowly and first and starting to pick up speed. Jessica was driving her nails into my back but it turned me on so much. We kissed and I kept going faster and faster. “Oh shit Jessica I’m about to come…”I said embarrassed. “Oh no you don’t buddy I’m not there yet.” I smiled a little bit and tried to hold off. After about 30 seconds I could feel her groping me with her pussy. This was just too much for me “I’m coming Jessica!”I said, nearly shouting. “Oh shit Alex faster! OH GOD KEEP GOING DON’T STOP PLEEEEASE!” She burst into orgasm. I slowed down, my dick going limp I gave her one last kiss and I slowly and reluctantly rolled off of her, completely out of breath. “God I love you Jessica.” “I know,” she said laughing. I started laughing too. I knew this wouldn’t be a night I’d soon forget. I dozed off and was awoken by the sound of a semi on the highway on the other side of the fairway. I looked around and it was nearly the butt crack of dawn. I shook Jessica awake and we got up. I walked her home, gave her a passionate kiss and she promised last night wouldn’t be the last one like it. I walked home in a trance, played last nights events over and over again. I flopped into my bed and home as tired as hell. Then I remembered about tomorrow. I fell on my bed and fell asleep immediately.

I awoke at the normal time on a school day, telling my unassuming parents goodbye, they didn't even notice my absence last night. At about 9 O'clock I didn't even bother calling Jessica. I rushed over and knocked on her door. She answered and just smiled. Jessica grabbed my hand and took me upstairs. We watched another movie. I laid down on her bed and she laid down cuddled up next to me. I slid my hand up her shirt and massaged her breast for a while, listening to her short soft moans. Jessica slid her hand down my pants and just fondled my cock and balls for a while until I was fully erect. She pulled my pants and boxers down and started slurping away. She pushed me down her throat as deep as she could get it, choking a little. I didn't last long watching her doing that. This time I didn't come in her mouth. After a while she stopped and stripped down to nothing and sat on top of it, going up and down doing all the work. I just laid there and watched the scenery. How she timed it I don't really know, but we came about the same time together, I didn't even have to try to hold back. "Oh god I've never had sex this good... AHHHHH" She screamed as she came. She got off of me and told me she was going to take a shower and clean up. If Jessica thought she was actually taking a shower she had another thing coming.

I waited about five minutes when I heard the shower turn on and walked towards the bathroom. For some odd reason the door was cracked, not even closed. I pushed it open and walked towards the shower curtain and pulled it open, but she wasn't there. Suddenly she leaped on me completely naked from behind and she laughed. "Bet you didn't see THAT coming did you?" she giggled. I grabbed her from behind and swung her around to the front and we got in the shower. We cleaned each other taking extra care with each others bits and enjoying each moment of it. That was one of the greatest days ever. We finished our movie and I went home because I had to be home when my parents got home. As she kissed me goodbye, she groped my crotch and I groped her breast. She noticed I was hard again. "Oh my god Alex you never go soft do you?" she said. "Only once in a blue moon" I smiled and she smiled back, I kissed her one last time and left for home.

Jessica~
18 comments

Anonymous readerReport

2009-03-23 23:37:57
did this really happen in ann arbor? how long ago? which high school? Don't take these questions the wrong way, i'm just curious because i live there.

Anonymous readerReport

2008-09-08 15:45:10
I think I'm the one who knocked your sister up. I took her cherry, when she was ten, and we've been fucking ever since. Your dog fucks her, too, so maybe he's the one who knocked her up. We'll know when she has whatever it is.

Anonymous readerReport

2008-09-03 16:59:42
THAT WAZ THE BEST FUCKING STORY IVE READ IN THIS HOLE FUCKING PAGE KEEP THEM COMMIN

Anonymous readerReport

2008-08-07 20:38:26
So you're the rat bastard who knocked up my sister Jessica

READER2Report

2008-08-06 06:36:04
thats kinda like me and my gf kali that story kinda was similar to how w emet and when i lost my viginity:)

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