Best Night of My Life Part 1

By JDawg21

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Tags: cheerleaders, breasts, ass

Added: 07 Nov 2011 Views: 20046 Avg Score: 4.96

Three cheerleaders prove that sometime a nice guy can finish first.
Authors Note: Although based on certain true events, this story is a work of fiction. It is intended for entertainment purposes only. It builds slowly and contains a lot of details. Yes, there is sex in this story. No, it doesn't happen right away. If you are looking for a story with raunchy sex at the get-go that never lets up, you probably won't enjoy this. Most of the scenes are a build-up of erotically charged circumstances.


I had just turned 17 when I experienced what would become the single greatest night of my life, up to that point anyway.

I was a Junior in High School. My life had passed by with no experiences between myself and any girls beyond first base, which was very disappointing. I was a classic “nice guy”. Girls were always happy to hang out with me, study with me (I was a straight A and B student), but they never wanted to date me seriously. I continuously found myself stuck in the dreaded Friend Zone with no escape.

It was shortly after the school year started that this story occurred. It was September, but in Arizona that means it was still well over 100 degrees during the day and not much better at night. My parents had decided to renovate our house and add an extension that would be a 4 th bedroom, since we only had a 3 bedroom and that left me and my brother sharing a room (my sister had her own room). My brother and I are very different people with next to nothing in common, so adding a new bedroom to give us some space was going to be great.

However, that meant one full weekend with one side of the house knocked open while the extension was added, and none of us really wanted to stay in the house that weekend with only a thin sheet of plastic covering the gaping hole in the side of the house that did little to keep our nice, cool AC inside.

My parents figured this was an opportune moment to get some alone time, so they booked themselves a nice suite at a hotel and arranged for all of us children to stay with friends for the weekend.

I was staying at my friend Joe’s house. He was 2 years younger but a nice guy and we had been friends for years. His sister, Lauren, was my age and in the same grade as me, not to mention a total knockout. Long brunette hair, deep brown eyes, and a tall athletic figure which was to be expected since she was on the Spirit Squad (our schools term for cheerleaders) and the dance team also. She was easily among the hottest girls in school.

She and I were never close, but she always was very nice to me and said I was her favorite of all her brother’s friends. She said all his other friends were 2 to 3 years younger like him and still very immature, particularly in regards to his hot sister. She said they were all little horndogs who spent most of their time making inappropriate comments and trying to spy on her in the shower or changing clothes. She liked me best because I was respectful and I also kept Joe acting more mature when he and I hung out.

I had spent the night at Joe and Lauren’s house quite a bit over the years. When we were all younger it wasn’t unusual for all of us to hang out late at night in the family room watching TV or playing video games all night long. Back then, of course, Joe and I usually just wore our little kid fruit-of-the-loom underwear and a t-shirt. Lauren would usually wear a sort of sleep shirt and just her panties, the sleep shirt was usually long enough to cover her panties but not 100% of the time. We were all too little to care about such things back then, of course.

These days, Joe and I were both older so we had graduated to boxers which seemed much cooler. Lauren, to my surprise, still wore the sleep shirt with no bra and panties, and by now she was old enough and hot enough to look really good in a pair of sheer white panties when I was fortunate enough to catch a glimpse whenever her sleep shirt failed to conceal everything, and I was old enough to appreciate it. Joe told me that she never just walked around in panties and a thin t-shirt when any of his younger friends stayed over, she always covered up with sweats. I guess she just felt more comfortable with me since I had been seeing her dressed like that at night for many years now.

Joe was a great hockey player, he was a slightly short and chunky kid who looked nothing like his sister with her long legs and trim, athletic figure. Seeing her in just a pair of panties also gave a great view of her legs, one of her best features (I tend to be a legs and ass man) along her tight, heart shaped ass that I secretly admired and ogled whenever I could.

Joe’s physical body shape did, however, make him perfectly suited to play hockey goalie. He was one of the best players in his league, maybe even the state for his age bracket. He had several other good players on his team that year and they qualified for the regional tournament in California at the last moment, which is what led to the night in question.

I arrived at Joe and Lauren’s house about 8 P.M. on Friday night, with a duffel bag full of my stuff that I figured I would need to stay for the entire weekend. My parents had set all of this up months ago, so I figured it was all set to go.

I knocked and was surprised when Ashley, one of Lauren’s best friends and another girl from my school answered. Ashley is another hot girl, which was not surprising since she was another cheerleader. She looks very similar to Lauren, with long brunette hair and a trim figure. Many people mistook them for sisters. She was wearing a half shirt which showed off her flat, smooth stomach and very short, cutoff jean shorts that exposed a lot of nicely tan and shapely leg (my inner horndog sprang to life at the sight of her incredible legs, I quickly shunned him back down and composed myself).

“Oh, hi Jeff!” she said, smiling brightly.

“Oh…um, hi Ashley” I stammered back. “I was just, um, I’m here to see Joe.”

Ashley looked a little confused, I wasn’t sure why, until she spoke again. “He’s not here. He’s in California with his parents for the hockey tournament.”

She must have noticed the look of confusion of my face, because she invited me in and called for Lauren. Lauren came around the corner to the front hall. She was wearing a pair a short, spandex shorts that fit her like a second skin, showing off her great ass almost as if she were not wearing anything, and short enough to still show off her own great legs. She wasn’t even wearing a shirt at all, just a matching sports bra, leaving her well toned tummy totally exposed and accentuating the firmness of her breasts.

“Hi, Jeff. Joe is going to be out of town all weekend. My parents took him to California for his hockey tournament thing. They won’t be back until late Sunday night,” Lauren informed me.

“Oh, ummm,” I continued to stammer. Two of the hottest girls in school standing in front me in tight, tiny outfits was not helping me to think clearly. “I was supposed to stay here this weekend. My house is being renovated so it has a giant hole in the side at the moment. My parents are at a hotel and all us kids are supposed to stay at a friends place. My parents set it up with your parents, like, months ago, for me to stay here.”

Lauren furrowed her brow. “Hmmm, that doesn’t sound like my parents to forget something like that. Let me check the calendar”

I knew she meant the monthly calendar that her mom keeps on the front of the fridge with a magnet. Her mom writes everyone’s appointments, Joe’s hockey games, football games that Lauren is cheLaureng at and such on the calendar. It had been September for almost a full week but the calendar on the fridge was still showing August. Lauren flipped it to September and written there on this weekend was “Jeff Staying” on Friday, Saturday, and Sunday.

“Huh,” said Lauren is surprise. “Here it is. Mom never flipped the calendar over to the new month. I guess with all the excitement with Joe’s team making the tournament they forgot.”

“So, what now?” I asked. “I can’t stay at my own place, for obvious reasons. And my parent’s just have a hotel suite for the two of them, I think they wanted a weekend away from the kids. I guess I could try and call my friend Mark. I could probably stay at his place tonight at least, but tomorrow he has some overnight thing at his church. Maybe I could stay with Sean on Saturday night….” I muttered as I tried to figure out what to do. It was already past 8 on Friday, working out last minute arrangements would not be easy.

“Oh, don’t be silly. You can stay here. We don’t mind,” said Lauren, and Ashley smiled and nodded. “We’ll feel better with a man in the house anyway. It was my parent’s idea for you to stay here so I’m sure they won’t mind. It’s not like they don’t know who you are.”

“Oh. OK then, I guess I’ll just…stay here then,” I said. “By ‘we’ I assume you mean you and Ashley?”

“And Sara,” said Lauren. “She’s in the other room going over the takeout menus. We were just about to order some food so you are just in time.”

Lauren called out to Sara, and she came into the room. This was getting to be too much. Sara was their other best friend, and another member of the cheerleading squad, of course. The three of these girls were always together so I shouldn’t have been surprised.

Sara was also very hot, but in a much different way from Lauren and Ashley. She was 18, as was Ashley though Lauren was still 17 like me. Sara was a blonde, for starters. Her hair was shorter, only a little past the shoulders but very cute. Bright blue eyes and a killer smile helped a whole lot too. She was the shortest, lacking the long legs of her friends, but she more than made up for it in chest size. She easily had the largest bra size in school, a very impressive set that was large yet firm and almost gravity defying in their pertness. Every guy in school knew who Sara was and would have given his right arm for a peek down her shirt. She was a huge flirt and the most daring of the three, having instigated more than one game of Truth or Dare, or Seven Minutes in Heaven at some of the parties over the summer.

Sara had been my one and only trip past first base, when I got picked at random from all the guys to spend those seven minutes in a closet with her at one of those parties, last year shortly after my 16th birthday. It was dark and I couldn’t see a thing, we kissed and made out and after a moment when I didn’t make a move she had literally grabbed my hand and placed it on her right breast. For those few minutes I had total access to her magnificent chest, fondling and squeezing both the left and the right, under the shirt but not her bra unfortunately. Second base, at least. I got a huge erection in my jeans, having never touched a girl like that before, but managed to fight it back down at the last minute as our seven minutes expired and the door to the closet opened.

She and I had never talked about those seven minutes. I was the envy of every guy in school, they all pestered me for details about what happened in the closet. Did I touch her breasts? Did I see them? Fondle them? Could I describe them? I just kept my mouth shut. I told everyone that all we did was kiss a little. The guys were disappointed in the lack of details and they all said I should have made a move on her. I just didn’t feel like sharing the salacious details with the whole school. I didn’t even tell Joe, and he had a serious crush on Sara, out of all his sisters hot friends. Being a leg and ass man I preferred Lauren and Ashley over Sara, but I certainly came to understand why most guys preferred Sara after that night.

So Sara walked into the front room, and saw me standing there holding my duffel bag. She smiled coyly and raised one delicate eyebrow in my direction. “And what do we have here? Is it an early birthday present for me?” she asked, causing me to blush furiously. Sara was wearing cutoff jean shorts like Ashley, though not quite as short. She had on what looked like a man’s button shirt, tied off at the waist with the sleeves rolled up and quite a few buttons were open, revealing a generous amount of cleavage from her magnificent set.

“Jeff was scheduled to stay with us this weekend. His house is being remodeled. I guess my parent’s forgot all about it. He doesn’t really have anyplace else to stay so I said he could still stay here with us. I hope that’s ok,” Lauren said.

“Well now, that’s just fine with me,” Sara cooed. “It should make the next couple of days more interesting. Of course, that ruins my plans to sleep in the buff tonight. Or maybe not. I’ll guess we’ll just have to wait and see.”

I was blushing even more furiously and I’m certain she was doing it on purpose just to get a reaction out of me.

Lauren tried to rescue me and distract Sara at the same time. “My parent’s said Ashley and Sara could stay over for the weekend, they didn’t want me staying in the house all alone. Now let’s see about those takeout menus. I’m starving.”

We ordered some Chinese, and while waiting for the delivery Sara looked in my direction and said “You know, Jeff, I’ve always wondered why you never told any of the guys about that incident in the closet.” Lauren and Ashley looked over at me expectantly as well, showing no surprise. They had been at the party so of course they had seen me and Sara going into and coming out of there.

“Do you two know about what actually happened in the closet?” I asked them, and they nodded.

“Girls talk, you know” said Lauren. “About everything. Sara told us all about it. She said you were a fantastic kisser and hand the soft hands of a surgeon. Most guys go straight for the nipple or start pinching or twisting. She said you were very gentle and took your time.”

I was sure I was blushing bright scarlet again, not even knowing how to respond. I never knew anyone else at school was aware of what had happened between Sara and me in the closet.

“You know, Jeff, the only other guy who has ever had the opportunity to cop a feel is my ex-boyfriend Trevor. He is a year older so he goes to the High School now and we’re not together anymore anyway,” said Sara. “That means you are the only guy in the entire school who has ever touched or caressed my breasts in anyway. Seems to me that would earn you a lot of cred in the locker room with the guys at school.”

“Yeah, I guess. I just, I don’t know, I guess I wanted it to be just between us. I know it was just a game at a party and I was picked at random but it was memorable for me. That was the first time I ever touched a girl. Actually, it’s the only time I have ever touched a girl. It didn’t seem right to turn it into some conquest story that I embellish and spread all over the school.” The girls were listening to me and seemed surprised when I mentioned it was my first time but they didn’t indicate that they thought it was anything I should be ashamed about.

Sara did seem a bit amused but to my surprise she stood up, and walked over to where I was sitting at the table. She leaned down to get closer to me, allowing me a very nice view down her shirt as she did so and I could see her magnificent breasts encased in only a small, lacy white bra that was so sheer it was almost see through. I could clearly see the outlines of her nipples. She put her face right next to mine, and whispered in my ear, “I’m honored to have been your first. And thank you for being so discreet. It’s nice to know that there are still some nice guys out there.” Then she gave my ear a little nibble, pulled back a little and gave me a brief kiss on the lips before standing up straight again.

I was at a loss as to how to respond, and Lauren and Ashley were both also watching with interest as to what I would say next, but thankfully I was saved when the doorbell rang. Our Chinese food had arrived.

As we dished out the food, we all sat around the table eating and the girls starting getting into “girl talk” mode. They started bitching about their ex boyfriends, I was surprised that all 3 were single at the moment since they had no shortage of guys willing to worship them for the opportunity to date them. They then went into detail about some of the other girls at the school and which ones were sluts, apparently Ashley had dumped her boyfriend just a couple days ago after she found out he slept with one of the Mat Maids (a sort of cheer squad for the wrestling team). Basically, the Mat Maids are comprised of girls who couldn’t make the Spirit Squad and they try to make up for not being the hottest girls by being the sluttiest instead. I was surprised that they were talking so openly about this stuff with a guy from their school right there in the room with them, but it was a rare peek into the thought process of The Teenage Girl so I listened intently while taking mental notes.

The girls then turned to me and they asked what I thought, and what was said in the guy’s locker room?

“Yeah, I hear guys talking about the Mat Maids in the locker room. A lot. I think Crissi has done it with at least half the football team by now. The guys even compare notes when they both have slept with the same girl. They don’t really respect the maids, but then the maids don’t really respect themselves either. They throw themselves at the football players and beg them for sex. Not a lot of teenage guys would turn that down.”

“And what do they say about us?” asked Lauren.

“Well, we all agree that the Spirit Squad girls are way hotter than the Mat Maids. And not just in pure physical hotness, but also as girlfriend material and not just a one time sex thing.”

“No, that’s not what I meant,” said Lauren. “I mean, what do they say about us?” waving her hands at herself and her friends. “What do they say about the three of us in particular? We are sharing intimate girl talk secrets with you, now it is your turn to give us the scoop on the guy locker room talk.”

Both Ashley and Sara also nodded enthusiastically. This was rare chance to hear the truth about what the other side really thought about them, if I was willing to part with the information. Let’s just say it wasn’t a hard decision in my part, not with 3 hot girls begging me for the details.

“I guess that is only fair,” I replied. “For starters, almost every guy thinks that Lauren and Ashley are related, like cousins or something. They agree that you two have the nicest legs out of all the cheerleaders and we all look forward to Fridays because you wear your cheer uniforms to school and we all appreciate the short skirts. As for Sara, she gets talked about the most in the locker room. She is the most outgoing, the most fun and flirty. I think she gets the guys more riled up than any of the other girls. And every single guy always mention her, umm, well that is, they talk about her…”

“My breasts?” Sara asked. “You mean these?” and she pulled her shirt open to reveal them sheathed in only the lacy white bra. “Of course they do. You can say it,” she laughed, tucking herself back in.

“Well, yes. Your breasts. Every guy in school would give anything to see them just once.”

“Even you?” asked Ashley. “You’re the only guy in school who has ever touched them. Does that put Sara number one on your list?”

“Well, I mean, I did really enjoy those seven minutes in heaven, don’t get me wrong. I just usually am attracted more to a great pair of legs and a great ass.”

“Really?” said Lauren, laughing herself. “Don’t tell me I’ve been walking around all this time in just my panties with a boy in the house who likes that sort of thing more he ever let on.”

“Well, to be fair,” said Sara, “you do have a great ass. You can’t blame the poor boy for looking if you sashay around in front of him in just a tiny pair of panties. Just my luck though. The only guy in school that I have allowed the honor of fondling my breasts and he turns out to be a legs and ass man.”

“You told us it was under the shirt but not the bra,” said Ashley. “Maybe if you let him caress them without the bra and see them with the light on instead of in a dark closet you could change his mind. I mean, if anyone could change him to a boobs man if would be you and your boobs.”

“Ha, not likely,” said Sara. “He’s been sneaking glances at your legs in those shorty shorts you are wearing all night long. I could probably stuff my exposed boobs directly into his face and he would still be checking out your legs or Lauren’s tight little ass in those skintight spandex shorts.”

All the girls were giggling and squealing with glee by now, and I was shocked to hear them talk so openly about each other’s bodies and which parts of those bodies I found the most arousing, but I couldn’t help but laugh with them.

“It’s all a moot point, really” I finally chimed in. “Yes, you are the 3 hottest girls in school and yes, you all look fantastic tonight and I have been appreciating the scenery. But since I am the classic ‘nice guy’ and you all ‘like me as a friend’ it is not like I will ever have a chance with any of you unless we get picked to be in a closet for seven minutes.” I sighed. “Story of my life, really. Mr. Nice Guy, always the friend but never the boyfriend. No reason we can’t hang out and have fun tonight though.”

I stood up and started collecting the dishes. “I’ll take care of these,” I said. “It’s only fair since you girls paid for the food.” I took the stack of dirty dishes into the kitchen and started to rinse them off and place them into the dishwasher. I thought I saw the 3 girls exchange a glance with each other when I mentioned being always being stuck as the nice guy who never gets the girl, and at one point while I was washing the dishes I thought I heard them whispLaureng together about something but I couldn’t make out what was being said.

After I finished the dishes and walked back into the dining room the girls said they wanted to watch a movie. Ashley and Lauren each took hold of my hands and dragged me into the family room and dropped me onto the couch. Where they up to something? They sat down on either side of me while Sara put a tape into the VCR and hit play. The movie was a romantic comedy, though I confess I don’t recall which one. It was one of the ones with Molly Ringwald. Pretty in Pink, I think.

What I do remember is both Lauren and Ashley deciding to cuddle with me, each laying all over me as we sat on the couch watching the film. Ashley had her head on my shoulder, and I remember she smelled really nice. I put one arm around her and pulled her in a bit closer and she nuzzled my neck and settled in nice and comfortably. Lauren actually layed down on the couch and put her head in my lap. With no other place to put my arm with her taking up that side of the couch I actually had my hand on her hip and as she twisted around a bit to get comfortable she rolled over onto her stomach a bit more and that left my hand on her ass. Not that I was squeezing or grabbing it or anything, but my hand was resting directly on her ass. Lauren didn’t say anything about or seem to mind, so I left my hand there for the rest of the movie, enjoying it more and more every time Lauren would shift around to get comfy and my hand grazed over more and more of her tight ass.

Sara was sitting on the love seat next to us. She was laying down on her back with her head propped up on a pillow, about five minutes into the movie she declared that she “was getting hot in here” and abruptly unbuttoned her shirt and tossed it aside. Ashley and Lauren both giggled and just shrugged as if to indicate that was Sara. She lay down on her back again, with only the small, lacy white bra that was practically see through encasing her breasts. Her nipples were most definitely poking through the thin fabric.

With all the distractions of Ashley nuzzling and even giving me little pecks on my neck every so often, my hand on Lauren’s ass with her not seeming to mind at all (I even got brave about halfway through the movie and gave it a little squeeze or pat a couple times) and Sara’s awesome breasts not 3 feet away, I don’t think I paid any attention to the movie at all. The girls all loved it and had obviously seen it many times, able to quote word for word the best scenes.

To my great disappointment the movie ended and the girls got up off the couch. “So what now,” asked Ashley, stretching her arms above her head, causing her half shirt to ride up and graze the bottom of her breasts. I could plainly see she wasn’t wearing a bra, but I don’t think she realized how high her shirt was.

“I feel like a swim,” said Sara. I knew there was a very nice pool in the back yard, having used it many times before when hanging out with Joe.

“That should be fine,” said Lauren.

The girls disappeared back into Lauren’s room to change into their suits...

continued in part 2