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My First Time With Samantha

Posted by: Author: Age: 20s Posted on: 0 comments
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This is a work of fiction. A fantasy of mine? Sure. But the people, places, and events in the story never happened, and are straight from my imagination. I hope you enjoy.


High school sucks. That's not an opinion, that's a fact. Whether you're quarterback of the football team, or president of the chess club, everyone goes through some of the worst experiences of their lives in high school. However, this is the story of how a tall, lanky nerd like me managed to have the single most erotic experience of my life.

Going into my sophomore year in high school, I was, in my own opinion, the single least attractive human being on the planet. At 5'10, 130 pounds, my physique was pretty much that of a stick figure. I had blonde hair, and hazel-green eyes, which were basically the only aspect of my appearance that I actually liked. I was socially awkward, didn't involve myself in any extracurricular activities, and was in nearly every aspect, the exact definition of a loser. And as any teenage loser can tell you, there is an astonishing lack of sex for the "offies" in high school. This was also intensified by the fact that I was a new kid in school, and knew absolutely nobody.

Going into the first day of school, I had made it my mission to find a hot girl to get with. And, as pretty much anyone could have predicted, by my fourth hour class on the first day, I had talked to exactly zero girls. I was mad at myself. I had seen plenty of them; from cheerleaders and dancers to drama girls, I had seen plenty, but had not had the courage to talk to any of them. I told myself that in my next class, I would find the hottest girl in it, and sit down right next to her. Was it cheesy and probably stupid? Absolutely. But my god, did it work.

When I walked into the classroom, my eye immediately was drawn to a beautiful girl with red hair sitting at a desk. Despite her red hair, she wasn't a ginger. She had a healthy tan, and had no freckles. She was looking down, reading a book and there was an open seat to her left. I swallowed my fear, and sat down next to her. She looked up at me.

I had heard the phrase "swept off your feet" used before, but I don't think I fully understood that feeling until I saw her eyes. Never before and never since have I seen eyes so passionately blue. Her red hair fell in bangs over her forehead. She wore some makeup, but it was very tasteful, and was hardly noticeable. I don't think she needed it anyway, because she is naturally gorgeous.

"Hi, I'm Samantha," she said. I snapped out of the trance I had been in and told her my name.

We started talking, and I discovered that she was also new there. She was shy, and in a lot of ways was nerdy. She read a lot, and she got straight A's. One thing that struck me was how intelligent she was. This was no stupid slut; she was witty and smart and simply amazing. We talked a lot the rest of the year, and ate lunch together every day. Eventually, by that winter, she asked to come over to my house. Our fourth hour was Biology, and we both needed to study for our midterm final.

She came over, and we went upstairs to my room to study. My parents were very laid back, and had always been open and had never shamed sexuality. They trusted me to be smart, and make the decisions I felt were best for me. But I honestly wasn't interested in sex that night; I was interested in not flunking Biology.

She and I studied for a while, but eventually we both got cold, and this was where the flirting began.

"Luke, why don't you break out some blankets? I'm freezing!" she said. Me, being a sixteen year old boy with the most beautiful girl I'd ever seen in my room, gladly obliged. We both laid on our stomachs on the floor, with the Biology book in front of us, but soon, the already scarce studying would become non existent.

"Feel how cold my hands are!" she said, and put her hands in mine. I realized she was flirting at this point, and began to flirt back.

"Here, I'll warm them up," I said, and held them close to my chest. She looked at me, and I looked at her. Her blue eyes were locked on my hazel ones, and I have no idea where inside me the courage came from, but I kissed her. Me, the tall, awkward, gawky sixteen year old who had never had a girlfriend in his entire life, got his first kiss. I was in store for much more.

Immediately, her cold hands went from in mine, to behind my back, gripping me, and she pulled me close. I rolled on top of her, and we began to make out. As she later told me, I was a horrible kisser, mostly due to lack of experience. But she didn't care, and in fact thought it was cute. I realized then that my door was unlocked, and my parents could walk in at any time. I knew they were downstairs, out of sight and earshot, and probably had no reason to come up and check on us. But, I wasn't going to be cock blocked by my mom, so I quickly broke the embrace, got up, and locked the door. Samantha, got up from the floor and laid down on my bed. We went back to making out.

Having already reached first base, I was feeling confident, and decided to go for second.I reached down and grabbed her boobs. They were c-cups, and were perky and round. Within a moment, she pulled me over to where we were both laying on our sides, and she reached down and began to massage my dick through my jeans. The feeling of cotton going up and down my circumcised cock, mixed with the sensation of her tits in my hands got me hard instantly. Her lips pulled away from mine.

"Do you want to go to Australia?" she asked.

"What?" I said, confused.

She giggled. "What I mean, silly, is do you want to go down under?" and with that, she stuffed her hand down my pants and boxers and felt my cock. I was shocked, and froze for a moment, but soon recovered as the feeling of her hand on my bare cock was amazing. I felt her other hand go for my pants button and zipper, and I started to pull her light blue t-shirt off.

By the time I had gotten it off, she had pulled my pants down so that now my underwear was the only thing covering my dick. She was wearing a white lacy bra, and she pulled her hands away from my cock to reach behind her to take it off. She got up on her knees, and I was still laying down when her bra dropped off and I saw my first pair of tits. Her pink nipples were medium sized, and I could feel my cock throbbing as she began to rub them.

"Wanna cop a feel?" she asked. I was too nervous to speak, but I managed a nod. I got up on my knees, level with her now. She grabbed my hands, and placed them on her breasts. I began to squeeze and feel, and it was simply amazing. She grabbed my t-shirt, and took it off me. After feeling her jugs for a while, she reached down and pulled my boxers down over my cock. Seven inches of hardwood sprung up at attention. She smiled, and said she was pleasantly surprised by how big I was.

"Your turn," I said.

"Oh, of course," she replied and unbuttoned her jeans and took them off. Now she was standing in front of me wearing only her white panties that matched her bra.

"Keep going," I said with a chuckle. She giggled and pulled down her panties to reveal her perfect little pussy topped by a small strip of red pubic hair.

She got back on the bed, and leaned back. With us both fully nude, I grabbed her tan legs and spread them apart. Her labia were plump, and I could tell she was very aroused. I rubbed my thumb across her slit, and she guided me to her clit. I rubbed it and she moaned. I proceeded to take my other hand and stick my middle finger into her hole. It only took a minute or so of fingering her and rubbing her clitoris before I felt her pussy begin to contract on my finger. She arched her back, and let out a soft, but passionate moan as she orgasmed. She laid there in the afterglow for a few seconds, and then lifted her head up to look at me.

She sat up, gave me a lustful little smile, and gently pushed me onto my back. She reached down, and grabbed my erect cock, which was extremely hard from having just felt her cum on my hand. She stroked it nice and slow to begin with, and I let out a low moan. She began to speed up, and using her left hand, she tickled my balls with her long fingers. She stroked even faster, and I let out a slightly louder moan as I began to feel my orgasm build.

"Oh my God, I'm going to cum!" I whispered loudly, and I felt rope after rope of warm cum shoot out onto my stomach and chest. My whole lower half of my body tingled, and I just laid there for a second motionless. I felt her mouth on my stomach as she licked up all of the cum and swallowed it. I looked at her. She looked at me. She leaned in and gave me a peck on the lips, and got off the bed to grab our clothes to get dressed. We studied for about fifteen more minutes before my parents came up and told her that her parents were here to pick her up. We hugged goodbye, and as we did, she leaned in and said "We need to do this again."

"Absolutely," I replied. She left, and I masturbated that night thinking about the experience I had that evening. I then proceeded to get a 65% on my Biology mid-term the next day. In hindsight, I'd say it was worth it.



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