High School: Zero to Hero Ch. 05

Although I firmly believe reading the preceding chapters is essential to the development of the story this far, I know it's been a while since I have published them. I have therefore decided to include a brief summary of the story to this point. As always, thanks again to my editor Romantic1.

The story so far: Shortly after his eighteenth birthday, Ben heads off to spend the summer before his senior year in high school lifeguarding at a rustic yet upscale country club in the mountains. There he manages to loose his virginity to his not-really-a-cousin cousin Ashley. Being a little older, a little wiser, and a little more experienced she offers to take Ben under her wing and help him become not only the best man he can be but the type of lover the women in his life would want him to be.

With a new found understanding of himself, and a bit more confidence, Ben returns to high school for his senior year. There he reconnects with his friends who are also struggling with their transitions into adulthood. Together they form a small tight knit group and begin exploring their developing sexual identities in ways only teenagers can do.

An unexpected turn of events finds Ben at odds with the starting quarterback and later has him standing in front of half the school awaiting word as to who will be crowned this year's Homecoming King and Queen.

Despite things heating up in the bedroom they are still students and some of them are also athletes. However, along the way new friends are made and brought into the circle and teenagers will do what teenagers will do when they have the time.

So, without further delay, on with the story.

Chapter Five - Birth of the harem

"We survived!" Jenn cried out as we exited the school on our last day of the first semester.

"Winter break here I come!" Sarah shouted.

Other hoots and hollers could be heard as other students flooded into the student parking lot after our last exam.

"Let's get going so we can get things ready for tonight," I said ushering the girls along.

The plan was to have an end of the semester party tonight at Jenn's house. Her parents were gone for the long weekend and wouldn't be back until Sunday. With other parties, we had demonstrated that we could handle a party on our own and not have anything get out of hand. We were pretty selective with who we invited and trusted everyone that came. Tonight would be no different.

Shortly after arriving at her house Jenn toke up a seat on a stool in her kitchen. "The three of us plus Ashley. Ben, Doug, and the twins make eight. Adding in Heather, Jess, Kylie, and Amanda make twelve. That's a pretty good sized group don't you think?"

"Hey, that's three guys to nine girls," I said with a laugh. "I like those odds."

"I bet you do," Jenn said in jest. "Especially since you've already fucked half of them."

"Good point," I said. "Now I know who I will be spending time talking to tonight."

"Us!" Sarah emphasized sarcastically.

"Uh, no," I said in my own sarcastic tone. "The girls I haven't slept with yet. Duh!" Two light slaps later, I was laughing so hard I nearly fell over.

Before the girls could resume abusing me, the doorbell rang.

Jenn opened the door and screamed. "Ashley!" They two of them hugged, and Sarah ran from her spot into the kitchen and nearly tackled Ashley to the ground with a flying leap into her arms.

"Hello to you too, Sarah." Ashley said once Sarah finally let go. The pair held each other at arms length.

"What, no hug for your cousin?" Ashley quipped when I finally sauntered out of the kitchen.

"Oh, don't mind him," Jenn said.

"Yeah. Knuckle head over there is going to spend tonight flirting with the girls he hasn't slept with yet," Sarah continued.

"Oh," Ashley said without much of a reaction. "I guess that means I get the two of you all to myself this weekend."

Before I could protest, the three of them ran upstairs and locked themselves in Jenn's room. I knocked but they told me to go away and that they were having girl time. I just shook my head and walked away. I figured my best bet would be to go pick up the drinks, snacks, and other stuff for the party from the store.

At the store, midway through my shopping list I ran into Summer.

"Hey Summer," I said. "Glad to be done with school?"

"Yeah. I really need this break. Physics and AP Government really kicked my butt this semester," She said with a sigh.

"Yeah, I opted to take just the regular government class. With taking AP trig, physics, and everything else I just needed something that wasn't super heavy." I said as we walked around the store gathering up our respective items.

"So what are you up to tonight?" I asked after a short period of silence.

"Actually nothing," Summer said. "I've been so focused on finals I didn't make any plans. I am sure there is a party somewhere I will get invited to."

"Well, about that," I said pulling my phone from my pocket. I dialed Jenn's cell and it just rang and rang. "Answer your damn phone," I said sarcastically. "Let me try again," I said to Summer hitting redial. This time Jenn answered.

"Oh, God!" She said panting heavily into the phone. "It's Steve," I heard her say to someone else. I could tell she was in the middle of something sexual.

"Everything okay?" I asked in a teasing tone.

"Oh, God yes!" She cried out again. "Jenn has a dildo in my ass and Ashley is working a vibrator in and out of my cunt," she moaned again.

"I ran into Summer, and she doesn't have any plans tonight," I said not sure if Jenn was in any condition to answer.

"Invite -- Oh, my God, yes! - her," she screamed. She then must have dropped the phone because it got a little quieter and I could her climaxing while Sarah and Ashley talked faintly in the background saying all kinds of dirty and nasty things to Jenn. I listened for a few moments before hanging up.

I turned to Summer and noticed she was blushing. "She sounded, uh, busy," she said unsure of how to phrase what she overheard.

"Oh, the volume was turned up wasn't it?" I asked semi embarrassed, not for myself but more for Summer since she looked like she was on the verge of blushing. She just nodded. "Well, if after that you still want to come tonight, you are more than welcome." She laughed and said she would think about it.

I went further, "Feel free to bring someone if you want. There is going to be about twelve other people there."

After walking together around a few aisles in relative silence, Summer finally asked me the question I knew she'd been thinking of for several moments.

"I thought you and Jenn were kind of a thing?" she stated. I just shrugged. "Well, you two have, uh, how do I put this?" She asked herself.

"Fucked," I said rather bluntly. This caused Summer to both laugh and blush at the same time.

"Yeah, I guess that's one way to put it," she said.

"We have fucked," I assured her. "And we're really good friends," I added.

"Then if you don't mind my asking, how are you okay talking to her on the phone while she's obviously with someone else right now?" I could tell she was trying to wrap her brain around it.

"It's complicated," I said trying to figure out a way to explain it without giving away too much private information.

"So are you boyfriend and girlfriend?" She asked.

"No," I answered. "More like friends with benefits."

"So, you're single?" She asked next.

"Technically, I guess. Yes. I would say I am single," I said trying to answer in her terms.

"Oh," she said thinking about it for a second. "Do you love her?"

"In a way, I do," I paused, "In some ways she's like a sister to me. We grew up as very close friends. In other ways, she is closer to me than a sister and more of a friend to me than many other people."

"Do you know who she's with now?" She asked continuing her line of questions.

"I do," I said definitively. "That too is kind of complicated."

"Oh," she said still unsure of her take on the whole thing. "Well, I don't want to pry."

"Okay," I said accepting she had enough information for now. I had a feeling she would be asking me more questions though.

Sure enough, a few aisles later. "Did you sleep with Heather the night of homecoming?" She asked stopping mid stride.

"A gentlemen never kisses and tells," I said trying to confirm her suspicion yet dodge the question at the same time.

"And Sarah from the track team?" She asked next.

I smiled, but otherwise gave her my best poker face.

"And Rachel the head cheerleader?" She was persistent.

"Ah, see that one is a flat out lie," I said. I would never sleep with Rachel. Never in a million years.

"HA!" Summer exclaimed as if she just trapped me. "So you did sleep with Heather and Sarah!" I didn't say anything.

"What about the Myers twins? Didn't you and your friend Doug go out with them earlier this year?" She asked.

"You aren't going to give up are you?" I asked. "Do we need to go through the entire female student body for me to quell your curiosity?"

"No," she said hanging her head. "I am just trying to figure out your type."

"My type?" I asked her wondering what she was tying to get at.

"Yeah," she said. "Blond. Brunette. Tall. Short. You know, the type of girl you're attracted to."

"I don't really have a type," I said as I mentally compared Sarah, Jenn, Ashley, and Heather. They were so far the only four girls I had slept with, and they had similar athletic builds but otherwise didn't have many similar features. Well, other than all being about the same height. "You know what," I said changing my mind, "I do have a type."

"What is it?" She asked.

"Well, I would have to say medium height, athletic build, long hair, and a great personality," I said with a touch of humor. "Oh, and a great ass."

"So, am I your type?" She asked giving me a strange look that was half curious, half flirtatious.

I gave her a quick once over. She had on a pair of black boots over her jeans. A heavy winter coat that hid a very athletic body with curves in all the right places. I had to admit that I checked her out from time to time during practice or at a swim meet. There were certain perks to being on a team that was both coed and in a pool.

"I guess so," I said. "You're beautiful. You have a very nice body that is trim and athletic, yet feminine. You're smart, have a great sense of humor, and you care about those around you." I paused. "So yeah, I guess if there was a measure of mutual attraction, I would say you're my type and given the chance I would entertain the idea of going out on a date."

"Interesting," was all she said. After we got to the end of the aisle I realized I had everything on my list, which left me with a cartful of items while Summer only had a bag of chips and a bottle of soda.

"Is that all you needed?" I asked as we made out way to the checkout.

"Yup," she said with a smile.

"I didn't mean to keep you," I said apologizing for tying her up for the last half-hour or so as I checked off every item on the list the girls made for me.

"The company and the conversation was worth it," she said with a smile.

Once my bill was totaled, paid for, and the bags packed, Summer was nice enough to help me push the cart out to my Jeep and help me load things up.

"So," I said as I shut the tailgate of my Jeep, "Will I be seeing you at Jenn's house tonight."

"Maybe," She said with a coy smile before turning around and walking back to her car.

"Women," I said to myself out loud.

+++

The party was great. Summer did show up along with Alex. Alex was a knockout like Summer. She was on the swim team with us, but unlike Summer's more proportioned chest she had breasts more like Heather. She loved to show them off too. She wore low cut tops and bras that pushed her boobs together and despite the cold winter weather tonight was no exception.

With the odds being pretty much four-to-one, it was a girl party. Ben, Doug and I found ourselves outside on the back patio at one point cooling off.

"So tell me boys," I said. "How does it feel to be dating the Myers twins?"

The exchanged a look and didn't say a word.

"Oh come on," I said. "Doug, you owe me."

"It's good," was all Doug would say.

"That's it?" I said. "You're dating two of the hottest girls in school and all you can say is 'good'?"

"Fine," he said. "You tell us about bedding Heather the night of homecoming, and we'll tell you about the twins."

"Okay," I said. I then proceeded to them the story as candidly as I could without making it sound like I was bragging. When I was finished I told him to spill it.

"First of all," Doug started, "The twins don't do anything by themselves. You think it's bad when two girls get up and go the bathroom together, imagine not only sisters but twins." I laughed. I knew how bad Jenn and Sarah could get at times. "So, all our dates have been double dates."

"Double," Ben parroted before taking a sip of water.

"So you guys haven't had any alone time with your own girlfriends?" I asked. "Bummer."

"Not exactly," Doug said, hemming and hawing. "Like I said, they do everything together."

"Everything," Ben parroted Doug again for emphasis. He flashed a slight smile.

"So, before Ben came along?" I asked holding up three fingers. Doug nodded. "And when Ben started dating Liz?" I asked holding up two sets of two. Neither one said anything, but they didn't need to.

"So, what was it like?" I asked after a period of silence. "You know, being a foursome."

"First time was weird," Doug said.

"Weird," Ben echoed.

"But once you get over that initial weirdness, well, yeah. It's worth it," he said with a huge smile creeping across his face.

"So worth it," Ben echoed. The two of them then bumped fists without even looking at each other.

"What about the two of them? Do they, well, you know?" I asked nondescriptly.

"Like I said. Everything." Doug said with a chuckle.

"Ev. Er. Re. Thing." Ben said.

"Wow," I said in disbelief. "Twins."

"Twins," the two echoed simultaneously.

"So yeah, I can say I have done something the great Steve Smith hasn't done," Doug said puffing his chest out.

"Oh, what exactly is that?" I asked.

"Have an four way orgy and experience two girls at the same time," he said while he gave Ben another fist-bump.

"Well," I said ready to correct him. "I'll give you that you've done twins, which I haven't done yet, but the key word is 'yet', and I have had both a three way with two girls as well as a four way with three girls."

"You're shitting me, bro," Ben said in disbelief. He leaned forward.

"Scouts' honor," I said holding up the old Cub Scout sign with my fingers.

Before we could continue the Myers twins, Heather, and Alex came on to the patio.

"There you are darling," Liz said walking up to Ben.

"We were wondering where the only guys at the party got to," Heather said taking up a spot next to me.

"We couldn't handle the amount of estrogen in the house," I said jokingly. "We needed to come out here and have some guy time."

"Well, the three of you are needed inside," Alex said. "Jenn has some kind of game organized."

'Oh shit.' I thought to myself. 'What is she up to now?'

The Myers twins helped Ben and Doug up, and Alex and Heather made sure to drag me into the house. I could see out of the corner of my eye that the girls were explaining something to their respective lovers.

"There you are, Steve," Summer said as I made my way into the living room.

"Where is Jenn?" I asked.

"She kicked us all out of the upstairs TV room and said she was setting up a game for us. You're to go upstairs to her room and wait for her there," Summer explained.

When I entered Jenn's room everything suddenly went dark as a blindfold was pulled over my eyes and tied behind my head.

"What the hell?" I asked in a near panic.

"Here," I heard Sarah say, "Sit him down." I felt a chair being pushed under me, and a sat down with a thud.

"Get his shirt off," I heard Heather say.

"I'll get his pants," Ashley announced.

So far, I placed three girls in the room but I didn't know why. And I was clueless as to why they were taking my clothes off.

"He's not putting up much of a fight," Sarah said disappointingly.

"Well, he is a good boy," Ashley said. "Aren't you?" She asked. I felt her fingers scrape across my bare chest.

"I would like to think so," I said trying to be humble.

"Do you think he's a good boy, Heather?" Sarah asked.

"Oh, I know he's a good boy," she said emphasizing the words 'good' and 'boy'.

I then felt a hand grip my now exposed dick. I thought it might be Heather's hand.

"Jenn wants him nice and hard," I heard Ashley say, "but don't get him too fired up just yet."

Whoever was handling my dick did as they were told. They got me nice and hard, but didn't stroke me any longer than they had to.

"Okay," Heather said, "He's ready." I felt a kiss on my cheek and then Heather whispered in my ear, "Just relax and try and enjoy yourself.

Heather helped me stand and led me to the TV room. Luckily, I knew where I was going. I got placed in an upright chair and then my hands were pulled back behind me and bound with a pair of fuzzy handcuffs. I heard Ben and Doug stumble into the room being lead by twins. I heard them get told to sit, and then I heard two more pairs of cuffs. I assumed they were naked and blindfolded as well.

"Steve? You in here?" I head Ben ask.

"Yup," I replied.

"You naked?" Doug asked next.

"Yup," I echoed.

"Any idea what's going on?" Ben asked.

"You guys watch Futurama at all?" I asked. They both said yes. "Well, I suspect death by Snoo-Snoo." Both guys laughed getting my rather obscure geeky reference to a clip from the animated cartoon show in which the main characters are threatened by a group of Amazonian women with the prospect of being fucked to death as a part of their mating ritual.

Once we were quiet we heard some commotion as the girls returned to the room. There were a few gasps and some oohs and aahs.

"Welcome to blowjob school ladies," I heard Jenn say from somewhere in the room.

Over the course of the next few minutes Jenn explained that she wanted to teach a few of the less experienced girls how to give blowjobs. Ashley whispered in my ear, "Some of the girls are shy and inexperienced; I won't tell you who, but you might guess." We were told that we were blindfolded so we would just judge the girls if they were bad at it, or try to hook up with them later if they were good at it. According to Jenn's instructions, the only thing we were allowed to say was if we were in pain or close to orgasming. Nothing more. Once the last instructions were given earplugs were inserted, and I went from being just blind to being nearly deaf too. A radio was turned up loud so we couldn't hear through the earplugs.

I sensed people moving around, a few forming a circle around me. I figured Sarah and Jenn didn't need pointers and would most likely be the ones sharing information. I figured the same for the twins and Ashley. I also knew Heather was an expert at blow-jobs, and I really hoped, for the sake of males everywhere, that she was willing to share some of her knowledge and experience.

By deductive reasoning, while I sat naked, blind, and deaf, I figured that left Summer, Alex, Jess, Kylie, and Amanda as prospective students. Just as I figured out who the students were, I felt a hand tentatively grasp my dick. Although it was hard, my dick was not yet fully engorged. It didn't take long to change that. I felt my dick change hands a few times, and each hand had a different feel to it -- a different grasp and touch. I also felt a few pokes and prods that must have been part of a more clinical exploration. My dick was lifted up, moved side to side, and even sprung like it was a diving board. My balls were also explored and played with.