My 2nd story ever, this is the last of my high school sexual adventures, chronologically. There will be more, but they all happened before this. This is a completely true story.
I highly suggest that you read my story "My Sister's Best Friend Raegen" first, before you read this. It will help you learn a little bit about me.
So for those of you who ignored my advice, here is some basic info about me. My name is Logan, I am about 5'10"(I stopped growing my sophomore year), well tanned, nice build, and fairly definitive muscle tone, and I have a 9 inch cock when hard.
This takes place 2 years after the events with Raegen.
I don't know when I first fell in love with her, all I do know is that it had happened, and there was no turning back.
"I could never have her though" I thought to myself. She was Ben's girl, and he was one of my better friends. Even if she was interested in me, I would never date her, I couldn't do that to Ben, could I?
It all started at the beginning of the Forensics team season, on the bus ride to the first meet. Although she was a sophomore, and had been in High School for a year and a half now, this was her first year on the team, and her first ever meet. She got on the bus and looked around awkwardly. None of her close friends were on the team, and she couldn't figure out where to sit. I felt bad for her, and since I figured she knew me better than others, since I was friends with Ben, I invited her to come sit by me, which she gratefully accepted, and took a seat by me.
That was when I noticed something I hadn't really noticed before. She was gorgeous. She was about 4'10" tall, and weighed about 125 lbs at the time. She had soft white skin, with just a bit of color on it, as she had just started tanning for the winter. Her brown eyes were beautiful, looking at me gently and softly, they could melt your heart just looking at them. She had long, soft, silky, brown hair. She was perfection.
We hit it off right away. She was nice, intelligent, smart, and caring. It was more than easy talking to her, it was natural. Throughout the season, it became a tradition that we would ride to the meet and back together. When she became tired she would fall asleep, leaning her head onto my shoulder. I never really took that as much, after all, she was just tired. But one day she leaned her head over onto my shoulder, then snuggled up against me, still awake. I looked down at her, in all her perfection, and realized, I was in love.
I never told her of course. She was Ben's girl, I had no claim to her, and I didn't want to make he uncomfortable, and ruin what we already had. So we just went on like we always had, sitting with each other and snuggling. That changed of course, with the last meet of the regular season.
In my state, each area is divided up into districts for Forensics, which then hold preliminary competitions to see who will be sent to state from each district. They take the top 3 places from each event and send them to state, and even though she had 2 more years of the team left, Carissa was stressing out over whether she would make it to state or not. She had literally stressed herself into sickness that day, so I pulled her aside and told her "Relax, you're going to do fine, I promise" she just smiled at me as if that was all the encouragement she needed. She gave me a hug, and walked off to her round.
The day went by quickly, and before we knew it they were announcing results. After about 30 minutes of giving out medals, they reached Carissa's event. Half of our team, including myself, had qualified for state. I imagine she felt like she had to make it, or she would feel like a failure. They began reading off the results. She wasn't called of as 6th, then 5th went by and it wasn't her. They looked at the paper, and called up 4th place.....Carissa. She was devastated. She held onto her composure long enough to accept her medal, shake hands with the organizer of the meet, and then walk back over to us. Then she buried her head into my shoulder, and started crying.
She went on like this for a while, all the way out to the bus, and about half way home, before she finally cried herself out. Even then, it took a hell of a lot of compliments and re-assurances about next year from me to calm her down. When she finally stopped crying, she raised her head up from her shoulder, and I saw she had a stray tear rolling down her cheek. I reached out to wipe it off, and when I did she looked up, and stared into my eye. I held her gaze for 5 second, and then she leaned in, and kissed me.
"What is going on" I thought to myself "I can't be doing this, she is Ben's girlfriend!" my conscious screamed out, but it just felt right. I began kissing back, and we began kissing even more intensely, then my hands, acting as if they had a mind of their own, began exploring. They worked their way under her shirt, and cupped her tits, which were size A, nearly size B, causing her to let out a gasp. After about five minutes of groping her tits, my hands then worked their way down, rubbing down her belly, along the curves of her waist, down around her inner thighs, until they finally reached her panties. I teased her by rubbing my finger along the outline of the panties, before finally pushing my hand under them, and getting a handful of pussy.
I felt a nice down of pubic hair above her slit, but nothing more than that. She obviously like to maintain her lower parts. I began rubbing my finger alone the outside of her pussy lips, and up and down her slit, causing her to gasp and quietly moan, while she thrusted her hips up to meet my finger. I did this for 10 minutes, until she was very wet, and then I slid my finger into her hole.
"Damn this is tight" was my first thought, as her vaginal walls constricted around my finger. I slowly began thrusting my finger in and out, being careful as to not break her hymen. She soon became more and more aroused, becoming closer to her climax. As I started fingering her faster, she started whimpering a little, forcing me to stop and remind her she needed to be quiet.
I kept on finger fucking her, picking up my pace for a whole of 5 minutes. I then took my thumb, and began rubbing he clit back and forth as my finger went in and out. This pushed her over the edge, and she threw her head into my shoulder, biting my jacket as she moaned in what seemed like an amazing climax. Eventually she came down from her orgasmic high, I gently lifted her face to look at mine, and gave her one last kiss, before we drifted off to sleep.
I woke up to bright lights being flashed on inside the bus. We had arrived home, and it was time to get off. I put my hands up to stretch as I yawned, only to realize my hand was still in Carissa's pants, resting against her pussy. Before I could even pull it out, I heard a gasp, and saw that we had been spotted. The guy who saw us got up, and left the bus quickly, acting as if he hand't seen anything. I didn't really think he would tell anyone, so I didn't mention it to Carissa when I woke her up. I walked her over to her car, gave her one quick kiss, and then walked off the my car.
I came to school that Monday, and things were a little weird. I would walk by groups of people and they would just start mumbling among themselves while looking at me. I didn't even think what this could be about, until my friend Joel came up to me and said "Did you really do it?" I was about to ask what, but then it hit me. He was talking about me and Carissa. I hung down my head and said "Yes." Joel simply replied "Good luck man.." and then walked off.
The day passed without incident up until 5th hour, when I saw Ben in the hall. I began to open my mouth to say something, an explanation maybe, but was interrupted by his fist connecting with my jaw. The pain immediately shot through me. I wanted to scream obscenities at him, throw a punch back, but instead I just collapsed onto the nearby wall, after all, I did sort of deserve it. Ben turned around and walked away without saying anything. It probably took all of his willpower for him to not beat the crap out of me.
Later that night, I was at home when I received a text message from Carissa. "Ben just broke up with me....I need someone to talk to, please come over..." I didn't even text back, I jumped into my car and drove over to her house, I made this mess after all, the least I could do was comfort her.
I got out of my car and knocked on her door. Her parents of course weren't home, her dad traveled across the state selling computers, and her mom worked as a nurse at the local hospital. She was probably home alone 90% of the time. She instantly opened the door, and flung herself at me, and began crying. I carried us into her living, and we sat down on her couch. She just sat there and cried for what seemed like forever, while I whispered comforting words to her. Eventually she ran out of tears, and just sat sniffling, when I felt that feeling again. What I felt on the bus that night. I looked down at her, and before I even knew what was happening, I began kissing her.
We both stood up and started kissing even more, my hands began straying again, and found the outside of her pajama tops, they gripped them, and pulled them off over her head. She sat back down, and I began kissing her down from her neck, across he chest and belly, down the the waistline of her pajama bottoms. I reached my hands up, and quickly pulled them off. I took in the sight, the most beautiful girl in the world, the love of my life, sat in front of my in only her matching red bra and panties.
My hand reached around her back, and un-clipped her bra. I pulled it off and threw it to the side. I took at quick moment to admire her perfect, rounder, and albeit small tits, before diving in and sucking one into my mouth, while fondling the other one with my hand. She let out a loud gasp, and with no one around to catch us, I didn't bother quieting her.
Eventually I worked my way down to her panties, and I slowly pulled them off to reveal the best looking pussy I had ever seen. It was hairless too. She had shaved recently. Was it just coincidence, or has she been planning this. Hell I didn't care, she was here, she was the love of my life, and she was ready. I dove my head into her pussy, alternating between flicking my tongue in and out of her opening, and sucking in her clit. My hand worked their way up and began cupping and playing with her tits, and pinching her nipples. I knew she wasn't going to last long. After about 15 minutes of this, she place her hand on the back of my head, and thrusted her hips out, and let out a loud moan as she climaxed.
After she cam down, she got up and began undressing me. She pulled my shirt off, then my pants, and finally my boxers, allowing my 9 inch hard cock to spring out. I saw her eyes widen, but she said nothing. She took it in her hand and began pumping back and forth for a while, picking up speed. After 20 minutes of this(I had jacked off a few minutes before she had asked me to come over) , I felt my balls tightening, and new I was about to cum. I told he I was close, so she picked up speed and began pumping as fast as she could. I couldn't hold it in anymore, I let out a loud moan as I came all over myself and her, splattering my chest with cum, and having some land on her tits and face.
We walked into the bathroom and hopped into the shower to wash ourselves off. While we were in the shower, we made out, and I teased her by rubbing my cock in between her pussy lips. When we got out of the shower, we were both hornier than we had been when we started. Still naked, we walked into her parents room, where she layed down on her parents bed, looked at me, and teasingly said "I'm waiting...." I knew what she wanted, but I wasn't sure if I was going to go through with it. She just broke up with her boyfriend, she probably isn't thinking straight, maybe I should wait. The only excuse I could come up with was "I don't have a condom." "My parents started me on birth control last year. I never had plans to do anything with Ben until we married, but my parents said I should still use it just in case. I guess they were right" she said with a smile on her face.
Well I guess this was going to happen. I walked over to her, and she spread her legs for me. I took my dick and gently put it against her hole, and then pushed. My cock popped in about 1 inch, before meeting her barrier. I looked her in those piercing brown eyes, looking for anything that might show uncertainty, but all I saw was pure lust. I backed out, and with a push, shoved 5 inches of my cock inside of her, breaking her hymen, and causing her to let out a whimper. She took it surprisingly well, and after a few minutes of her adjusting, I began picking up pace. I was ramming it in and out faster than I had even with any girl before, my balls slapping against her ass as I pumped in and out echoed throughout the whole house, mixed in with her screams of pleasure.
Eventually with each thrust I was completely bottoming out, shoving my entire 9 inches inside of her pussy. I knew I wasn't going to last much longer, and began fucking her with increase speed. As I picked up speed, her moans started blending, until it was just one continuous groan the filled the room. She finally hit her climax, letting out a shrill scream, yelling "Oh my god! Aaaaaaaahhhh, oh my god Logan, I'm so full right now, ooooooohhhhhhh mmmmyyyy godddddddd" she began screaming. All I had to do was look down, she her small titties rolling around as I pounded her pussy, and feel her pussy walls contracting around my dick as she was climaxing, and I was pushed over the edge. With a final thrust I pushed into her, and came inside of her. I had never came so much before in my life, not even after my first time having sex. I filled up her entire pussy, and then it began squirting out, onto her parents' bed. The feel of my warm cum filling up the inside of her pussy sent her into another orgasm, making her squeal again.
Eventually we both came down, and like that night on the bus, feel asleep cuddled with each other.
This is the last time I ever had sex in high school, or college for that matter. All the true stories I am posting from here on happened before this. Why did I stop having sex with people, when I seemed to be on a roll? Because of Carissa. I have been dating here for 3 years now, and they have been the best 3 years of my life. I am a junior in college, and she is a freshman. We attend different colleges, but we still visit each other on weekends. So yes, unlike any of my other stories, this one actually led to a relationship, that still lasts to this day.