tagFirst TimeHigh School: Zero to Hero Ch. 00

High School: Zero to Hero Ch. 00

byyoursilentknight©

This is the beginning of a rather long series (Prolog, ten chapters, and an epilog). There is also a follow up series in the works, so if this is well received I hope to continue the development of the characters. This is not a quick "stroke story" but it is not a novel either. Each story will be branded with the 'theme' that best fits. Story elements will include mostly first-time, group sex, and romance.

Lastly I would like to thank 'Romantic1' for serving as my editor. Over the years I have enjoyed reading his stories and his Road Trip series is what inspired me to get back into writing.


High School: Zero to Hero - Prolog

July fourth between my junior and senior year was the day my life started to change. It was the night I can honestly say I became a man. Even though I had turned eighteen at the end of June, I didn't feel any different. Ashley managed to change that.

We were sitting out in a field watching the fireworks. The night had a gentle breeze which chilled the summer air. Ashley, clad in cutoff shorts and a tank top, shivered. Instinctively I wrapped my arms around her in an attempt to keep her warm. I didn't think anything of it. She seemed to appreciate the added body heat and nestled herself back into my lap and pulled my arms tight around her. Had it been any other girl than my cousin, it would have been a very romantic moment, at least that's what I thought.

I guess I should mention that Ashley isn't my cousin by birth. She is my step father's niece so our cousin status is only by name and not by blood. As I wrestled with this in my head, I thought back to how she has extended an offer for me to come work with her for the summer as a lifeguard at a posh mountain resort. I was a little surprised by her offer since we had little in common other than both being competitive swimmers. She was also a few years older than me, so we rarely had much to talk about during family gatherings. However, the pay was better than the job I had the previous summer, so I took it.

Apparently being 'cousins' wasn't an issue for Ashley. In the middle of the grand finale, she turned her head, leaned back and looked up at me. Expecting her to say something, I looked down at her. She looked into my eyes in a way I cannot really explain and then kissed me. My own cousin kissed me right on the lips. I sat there in shock, and passively accepted her kiss. After a few seconds, she stopped, and we watched the last few seconds of the grand finale.

Once everything was finished, we started our walk back to the staff cabin area. The resort we worked at was a lot like a country club expect it had more of a rustic feel, and people came to stay for weeks at a time. After a few steps, Ashley slipped her hand into mine, and we walked the rest of the way hand in hand. Since Ashley was senior staff she had her own cabin and thus a measure of privacy. In contrast, the cabin I shared with two other staff members sat in the middle of a cluster of smaller cabins.

"Steve," Ashley said turning to face me when we reached her cabin, "Can I ask you a personal question?"

"Sure." I said not really sure what she would want to know. I don't have anything to be ashamed of, well maybe kissing my cousin, but seeing as she was the one asking me, I didn't think I had to worry about that being too taboo.

"Are you a virgin?" She asked bluntly. Bluntly enough so that it caught me a little off guard.

"Uh. Yeah." I paused for a second, "I mean, I've kissed a girl. You know, other than you tonight, and fooled around a little. But never, you know, gone all the way." The most recent kisses I had gotten before Ashley were two of my high school friends Sarah and Jenn on the day of my eighteenth birthday. While there were no real romantic feelings, Jenn and I made out a little. Other than that I didn't have a whole lot of experience with women.

The light from the cabin's porch was casting a soft yellow glow on her face, and I could tell she was looking at me intently; so, in turn I looked back at her and gave her a quick once over.

She had on a pair of flip flops which showed off her dainty feet and cute toes topped off with a red, white, and blue nail polish pattern. Her legs were had an athlete's tone, and her short cutoffs accented her thighs. Her tank top was short enough to show off a teasingly amount of her flat abs and her pierced belly button. The cold night air had caused her nipples to poke against the thin fabric of her tank top which stretched over her medium-sized breasts. They weren't the biggest things I had ever seen, nothing like what I had seen on porn websites, but they were slightly bigger than most of the other girls on the swim team with me. She had her hair pulled back into a ponytail that stuck out from behind her lifeguard visor. When I finished my once over, my eyes rested in her deep blue eyes which were still staring intently at me.

"What if I could change that?" Ashley said, again rather bluntly.

"What do you mean?" I naively asked.

"What if I offered to teach you everything you ever wanted to know about sex, and help you enter your senior year not a virgin?" She said with a coy smile.

"But you're my cousin," I said sheepishly.

"We're not related," She said. "We can do whatever we want, and there is nothing illegal or immoral about it." Her coy smile grew to an impish grin. "Plus, it will be a long summer for both of us if we don't do anything about this sexual tension between us."

"What sexual tension?" I asked, still oblivious that a hot girl was throwing herself at me.

"You're hot," She said again being blunt. "And I see the way you look at me around the pool when I am in my suit."

I guess I had been caught. I am a red blooded teenage male. I don't care if it's your cousin, your sister, or whatever, if you see a hot girl in a swimsuit, you will look.

"I..." before I could say anything else, she cut me off.

"Here's the deal," She said motioning me to a bench swing in front of her staff cabin. "I already know that coach has been scouting you for a spot on State's team. He sees some real potential in you. So I figure if you end up going to college at State, you and I will get to hang out a lot more. I also know what it's like to be an awkward teenager in high school and have no clue about sex, romance, and whatnot." She paused. "No offense."

"None taken," I said instinctively.

"I was lucky enough to have someone show me the ropes, so to speak, and teach me about sex without making it weird." She stopped for a second to let my brain catch up and make sure I was following along. "So, I am offering to do the same to you. I do like you. I liked you when we first met that one Thanksgiving a few years ago, but we really didn't have time to get to know each other."

"Okay," I said still taking it all in. "So how is this going to work? I mean is it just going to be Sex Ed 101 or something?"

She laughed which caused me to be a little embarrassed at my lack of knowledge on the subject. Sensing my embarrassment she slid a little closer to me. "Not at all." She looked at me and smiled. "But first, you have to tell me you're okay with the idea."

"If you will be my teacher, then I will gladly be your student." I smiled at her and I decided to just throw my insecurities and sexual ignorance out the window. Then, and I have no idea where it came from, but deep inside of me a switch went off. I decided to come out of my shy timid shell, so I leaned down and kissed her. Not a chaste on the lips kiss like before, but an honest to goodness kiss. Our tongues found each other and for the next few minutes we just kissed under the stars while the swing rocked gently back and forth.

"Wow," Ashley said as our kiss finally broke, and we came up for air. "You are a damn good kisser."

"Thanks," I said relishing in the compliment.

"I guess that is one less thing I have to teach you," She smiled, "You're off to a good start already."

We sat in silence for a little while before Ashley suggested we head inside to get out of the chilly air.

"One of the perks of being in charge of the pool this year is that I get my own cabin." She did a little twirl with her arms out as she entered the middle of the main room. "Not much, but it is home for the summer."

I sheepishly stood near the door still unsure of my role in all this.

"Have a seat." She said gesturing toward the small couch. "Would you like something to drink?" I nodded, and she brought me a bottle of water and took her seat next to me.

"Let me lay out a few ground rules first, so that you understand how this will work." She explained, "These were the same rules laid out for me, and they seemed to have worked." I just nodded and followed along. "First, if at any time you're uncomfortable with something, just say so. Second, if at any time you want to know something, just ask. There are no limits other than the ones you set for yourself. Lastly, no falling in love." This one caught me a little off guard. "This whole process will be very emotional for both of us. We are going to share something that is very unique and very powerful. We will love each other, but I do not expect you to fall romantically in love with me and become my boyfriend. The point of this process is for you to learn. We will always have a special bond, but I don't want to get in the way of your experiences when you go back to school, and I don't think you want to get in my way either. Is that okay?"

Truth be told, I had never had a girlfriend, so I guess I could handle it. "Yeah." I nodded in affirmation.

We spent the next few hours talking about everything I thought I knew about sex, love, life, and relationships. We talked about all my misconceptions about what kids my age were doing in high school compared to what they said they were doing. I was surprised to find out that, rather than being the weird one and still a virgin, it was more likely that most people in my school were virgins than not. We also talked about porn star sex versus what sex was really like. In some ways our discussion was very arousing, but also very clinical. I found myself getting aroused and then calming back down as the conversation would shift from something overtly sexual to something more benign. Every now and then, I would steal a glance at Ashley's breasts or down to her crotch which, with her sitting Indian style next to me, gave me a little peek at her black underwear.

We also talked a lot about how I perceived myself. I explained to her that I felt like I was a relative nobody in school -- a geek. It wasn't that I had low self-esteem, it was just that I didn't fit into any particular clique. I was smart, but not smart enough for the nerds. I was athletic, but since I was a swimmer I didn't fit in with the jocks who played more popular sports like football or basketball. I did have a few close friends, but otherwise I felt invisible.

It was two in the morning when I realized what time it was. Ashley and I had been talking for nearly four hours and had covered so much ground. Yet it didn't feel like we had been talking that long.

"I think it's time for bed," Ashley said stretching her arms up over her head while yawning. This gave me a very nice glimpse of her stomach as her tank top rose up.

Thinking this was my chance to make an exit and do something about the raging hard-on I was dealing with I thanked her for giving me this opportunity and teaching me so much in just one night. As we got up, I gave her a hug and then started to walk to the door to show myself out.

"And just where do you think you're going?" She said placing her hand on her hip and looking at me as though I were doing something wrong.

"Uh, to bed?" I asked rhetorically pointing toward the door.

She smiled and then pointed toward her bedroom door.

When we were both in her bedroom, she turned to face me. "You're first real lesson is going to be two fold." She stood a few inches from me letting the sexual tension build. "The first part is going to be patience. The biggest problem a lot of people have when it comes to sex is that they rush things. It's common with guys, but girls are just a guilty. So be patient. Take your time. Enjoy it." She paused letting the first part sink in. "The second part is going to be hands on." She flashed that impish grin at me for a brief second. "I am going to let you explore my body tonight. No sex. So there won't be any pressure on you to perform. I just want you to be able to touch what you want to touch, feel want you want to feel, and see what you want to see." She paused for a second. "And don't worry, I'll enjoy it as much as you will."

I took a step towards her. I may have not known much, but I knew enough that starting off with a kiss was probably a good idea. I leaned down and we kissed. While we kissed, I let my hands roam over Ashley's body. I teased my hand up and down her sides, across her back, and down to her ass. She was a few inches shorter than I was, and had a petite frame compared to my broader physique. I cupped one hand on each ass cheek and lifted her up. She in turn wrapped her arms and legs around me, and let me carry her toward the bed.

She giggled as I tossed her to the bed. "You're a natural," She said striking a sensual pose on the bed. "Now, be a good boy and take off your shirt." She paused. "And remember, take your time."

I did as I was told. I slowly peeled my shirt off. I made sure to accentuate my movements without overtly flexing any of my muscles. Ashley licked her lips in anticipation and gave me a wanton stare as I tossed my shirt onto the chair next to the bed. I then took our evening a step further and slowly undid my shorts and slid them to the ground without letting them just fall. I turned and walked away from her giving her a view of my backside as I bent over in nothing more than my briefs.

"Um," She moaned out loud, "I love the view tonight."

I pulled the back of my underwear down. "Then you'll love seeing a full moon." I turned pulling them back up and walked back towards the bed.

"This is good," She said with a giggle. "Another key to this whole sex and romance thing is to have fun and not take it too seriously. So many times people get caught up in trying to make things perfect that they forget how much fun sex and intimacy can be."

I crawled onto the bed and hovered my body over her. "You know what I want?" I asked in a low husky voice.

Ashley just shook her head side-to-side.

"I want to see this amazing body of yours. I've wanted to see it since we first met." I could feel her body melt beneath me. I guessed I must be doing something right, so I continued talking. "I want to see those amazing breasts of yours. I want to see that amazing ass. I want to see your pussy." She moaned again. "You like that idea don't you?" I asked her. "You like the idea of showing your cousin your naked body."

She moaned an affirmation. Our lips were inches away from each other. One lesson I had picked up on from watching porn and reading erotic stories was the idea of dirty talk. I could only guess that from what I had said so far and her reactions, I was doing all right.

I rolled over onto my back and then pulled Ashley up onto of me so she was straddling my hips. I could feel the warmth of her crotch pressed against mine. It was something I hadn't really expected, but I welcomed the sensation.

I let my hands roam over her body as she straddled me. I let my finger glance over her breasts and stomach with a light, airy touch. She bit her lower lip which really turned me on. She then reached back and pulled the tie out of her hair letting it fall haphazardly across her shoulders. I slid my hands under her tank top and then slowly lifted it up over her head and tossed it aside. Her breasts were now clad in only a black lacy bra. I could see the faint outline of her nipple and areola through the fabric.

I pulled her down for another kiss and let my hands roam over her freshly exposed skin. I let my fingers lightly graze her back which caused her to gasp into my mouth. After letting my fingers trace and dance their way around the outline of her bra, I finally undid the clasp.

Ashley sat up straddling my waist and held the bra to her chest with one arm while she brushed her hair behind her shoulders with the other. She then slowly teased the bra out from under her arms. She bit her lip as she watched me intently following ever movement of her hands just waiting for that first glimpse of her exposed breasts. She cupped one breast in each hand and looked down at me with a smile.

"34C," She said with a smile. "I will explain what that means in detail later, but soon you'll get an idea of a girl's size just by looking at her." She paused and bit her lip again. "I love my breasts. I think they are the perfect size. Don't you?" All I could do was nod. My dick ached in its trapped position pined between our hips. "I've always said more than a handful is a waste." For emphasis she squeezed her breasts. "You know what else I love about my breasts? I love that my nipples are so sensitive. Sometimes I can orgasm just from having my nipples played with."

This time for emphasis she squeezed her legs against my body. This pushed my hips up and ground my dick against her crotch. It must have been equally enjoyable for her as it was for me because she let out a soft moan. She continued to play with her breasts squeezing and kneading them in her hands. It was torture for me to watch but I reminded myself to be patient. After a few more agonizing moments of watching her play with her breasts, she finally revealed her bare breasts to me. "You like?"

I licked my lips in anticipation. "I do. They're prefect," I said. I had seen many fake boobs on porn stars and they just never looked right to me. I also didn't like huge boobs since they just seemed to be more trouble than they were worth. Most of the girls I was around had tight, trim, athletic bodies and were, as I would later find out, more in the A to B cup range.

I ran my hands, which I had let fall to my side on the bed, up her legs to her hips, then up the sides of her ribs to just bellow her breasts. I let my thumbs cup under each breast while my fingers slowly inched their way across the tops of her breasts. Once my palms were centered over her breasts, I gave them a gently squeeze. They felt soft, yet firm. Spongy, yet springy. Ashley moaned as my hands and fingers explored and played with her breasts. She let out a more desperate moan when I pinched her nipples between my fingers.

"Another way to stimulate the nipples," She said nearly panting, "Is to use your mouth. Would you like to suck on my nipples?"

Wordlessly, I pulled her body down to mine and took her left breast in my mouth. I really didn't know what to do, but began by just sucking on her nipple.

"Use your tongue," She said panting a little heavier. "Pretend you're French kissing my nipple." I did as I was told. "Oh God yes," She moaned. "Just like that. Now make circles," She moaned again. "Now, here's a trick. Write the alphabet with your tongue on my nipple, and play with my other one with your hand."

Again, I did as I was told. 'A. B. C. D.' I kept going. 'E. F. G.' Ashley let out a guttural moan. 'H. I. J. K.'

"Oh God, you're good," She nearly panted.

'L. M. N. O. P.' She then shifted so she was propped up on her left arm. With her right hand, she grabbed my hand and crushed it against her breast and squeezed more forcefully than I was. I took it as a clue and grabbed tight against her breast. 'Q. R. S.'

She let out another deep guttural moan and squeezed her legs together against my body. The heat coming from her crotch was almost an inferno now. If this kept up for much longer I feared I was going to blow my load in my underwear. 'T. U. V.'

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