Sexual Awaenings

Chapter One - The Beginning

This story begins like any other story. That is, any other story about the time you had a weekend detention with two other eighteen year old female classmates. But this is the best story to start with when it comes to the overall story of my early adult years.

I had attended a private, meaning religious, school since the seventh grade. It wasn't all bad I suppose. But by the time I reached my senior year and turned eighteen I was more than ready to be done with the strict rules and the irrelevant punishments. Every Friday morning there was a chapel service and every Friday morning, since I had turned eighteen two months back, I weaseled my way out of going.

Normally I had done so by simply being late but on a few occasions I had gone out to a diner with two young women that I desperately wanted to avoid what I was already in. The dreaded friend zone.

The three of us got along quite well. Besides me, a strapping five foot ten inches tall young man with short brown hair and hazel eyes , there was Ashley and Emily. Ashley was the school's head cheerleader and had long, blond hair and bright blue eyes. Emily was also on the cheer squad and also had long blond hair, though she had green eyes and was a few inches taller than Ashley but still an inch or two shorter than me.

Well on one particular Friday morning in early April the three of us were pulled from class and directed to the Headmasters office. We knew we would all graduate in less than eight weeks so we didn't dread going. We assumed there wasn't much he could do. But I would end up being glad to be so very wrong this time.

"I've had enough of your excuses! Every Friday you have some reason to miss chapel and now, now you're gonna miss your precious Saturday! Instead of being able to sleep in and relax all day you will be here!" said the headmaster to the three of us. "Now I've already contacted all three of your parents and I have their support in this matter."

We were all standing in his office, Ashley, Emily, and myself, Brandon. Though we thought most of, if not all, our absences from chapel had gone unnoticed we were apparently wrong. Now, it seemed, was the time to pay the piper.

"Tomorrow you will spend as long as it takes to repaint our teachers lounge. As you know, being a privately funded school we get no help from tax revenue so we have to get a little creative when we need some upkeep performed around here. You all just volunteered for free labor. I'll be here to let you in at ten and then I will lock you in. The door is self-locking when you leave but the job better get done. I'll be back by five so no goofing off."

"Yes headmaster." we replied.

While I could think of much better ways to spend a Saturday morning / afternoon it wouldn't be so bad with these two girls to keep me company. Perhaps I might make some headway in breaking out of the friend zone with them. At the very least I'd be spending quality time with just them while we weren't having to abide by the school's strict dress code.

I showed up the following morning in a pair of well-worn khakis and a t-shirt. Figured I might ruin whatever I wore so it might as well be headed for the trash pile anyways. Just as I parked and locked my truck I heard another vehicle pull into the lot.

Ashley parked and walked over to me. She wore a pair of torn jean shorts and a shirt that stretched tight cross her chest. It wasn't low-cut but it did leave little to my imagination. There was a rumor amongst the guys in my class, for over a year now, that her boobs were enhanced. During the summer between our sophomore and junior year she had developed quite the pair. I seriously doubted the rumor myself and thought it was a oddly-timed coincidence. Having attended a few basketball games and watching her cheer I also could tell that she had a nice bottom.

"Hey Brandon. What no sexy jean shorts for you?" she smiled as she thrust her hips sideways.

I couldn't figure out what was hotter that morning. How much sex appeal she was oozing out, or that she was so confident in doing so.

"No I'd be afraid of showing too much with tight shorts on." I replied and opened my arms for a friendly hug.

"Oh come on. We're friends aren't we?" Ashley welcomed the hug. "And friends share with each other don't they?" It wasn't a tight hug but thanks to her massive chest it didn't have to be in order to feel her against me.

Before I could reply or attempt to move my hardening dick into a tucked position we heard Emily calling out to us.

"Hey guys, wait up!"

I turned to watch Emily jog towards us. While she wasn't as busty as Ashley she certainly wasn't flat either. If I had to compare them I'd say that there was no way I could fit one of Ashley's tits in one of my hands but I'm pretty sure I could just fit one of Emily's.

However, she had something else that, for me, was a greater asset. It had been at one of those away games for basketball that I had attended I had walked in on Emily changing into her cheerleading uniform. She didn't know I had seen her when she was naked from the waist down cause she had been facing away from the door. I had stared for a few seconds and backed away, silently. Even now I don't know how she had mixed up the boys and girls locked forms at that school but I can still picture her smooth, round ass in my mind.

Between Ashley's friendly hug, memories of Emily's bare ass, and me being a eighteen year old male, I now had rapidly tightening shorts. I made an excuse up that I had forgotten my wallet in my truck and used the driver side door to block the adjustment I made. Under my shorts I was wearing cotton boxer briefs which made it easy to tuck my semi-hard shaft so it wouldn't be as obvious.

After a few minutes of standing by the school's entrance the headmaster pulled up and unlocked the door for us.

"All the supplies are in the lounge for you and all of the wall furnishings have been removed. Your job is simple. Roll as much of the wall as possible and use brushes to finish the trim and corners. It should take you the whole day to get it done. I'll be back by five and expect a completed job. Any questions?"

None of us had any so within two minutes he was gone and we got to work. The first three hours seemed to fly by for the most part. We talked about school and rumors and such, nothing noteworthy. Both Ashley and I had painted rooms before so we rolled all four walls by one in the afternoon. That's the hour that started the change for all three of us.

"Oh what the hell?!" Emily and I heard Ashley ask loudly.

Given our current topic of conversation we both assumed Ashley had found something else to complain about or gotten paint on her clothes again.

"What now?" I asked, slightly exasperated.

"Oh nothing I suppose." Ashley responded, picking up on my tone. "Unless you are hungry for lunch and then you realize the old bastard didn't leave us anything to eat and the main door locks behind us."

"So now what? Cause now that you mention it I am getting a little hungry." Emily stated.

"Let's just take turns going to lunch." I suggested. "That way we can finish this damn painting and we won't get locked out."

"Sounds like a great idea Brandon. I'll even go first." Ashley volunteered.

"Wait, what?" I was momentarily confused at her quickness.

"It's all right Brandon. Go ahead Ashley. All we've got left is trim work anyways." Emily said.

Ashley grabbed her purse and took off. I was left with Emily by myself now. I tried to clean up at first, to keep my distance, as I didn't want to embarrass myself or her. I was attracted to her but I also had heard she was still a virgin, after having a steady boyfriend for the past two and a half years, so I assumed she was saving herself. And I didn't have a problem with that. I wasn't one myself but who was I to judge. Then, just a few minutes after Ashley had left, she needed my help with the ladder.

"Brandon this ladder is a little wobbly. Come over and hold it steady so I don't fall." Emily stated more than asked for help.

Now I had always considered myself to be a gentleman to ladies. A horny gentleman but a gentleman still. But when I took hold of those bottom legs of the ladder I still looked up. I saw what would still be my favorite bottom years from that day. Under her pleated mini-skirt Emily was wearing a nice pair of pink cotton bikini panties. The bottom half of each cheek was laid bare for me to stare and be aroused at. It was one of the fastest erections I got in my young life.

After I stared at her round bottom for a minute I looked away. It was just in time as Emily finished with the space she was doing and needed to move the ladder. Once again she had me hold it and once again I stared at her beautiful ass.

It wasn't bad enough that it was my favorite part of the female anatomy. It wasn't bad enough that a girl I was already attracted to had such a nice round one or that it was just a few feet above my head. It wasn't even bad enough that I was pretty sure no one else had ever seen it completely bare. No, the worst part was that this would be the closest I'd come to it. Unless I risked our friendship.

But that would be a big risk I told myself as we once again repositioned the ladder. Sure the reward would be great but I'd risk not only Emily's friendship but potentially Ashley's as well. I decided to not risk it.

Chapter Two - The Decision

Then again...

It was Emily, the virgin, who had worn the revealing panties. It was the virgin who had me holding the ladder while she painted. It was Emily.

By the next time she was done and ready to come down I had made up my mind. I'd stay close to the ladder as she came down and see how she reacted. I hoped I'd make quite the impression.

Emily took each rung slowly and kept her body bent at the waist. Her bottom stayed out away from the ladder and I became convinced she knew exactly what she was doing. I stayed still, with my erection held upright against my waist, and let her descend. When her legs passed between my arms I saw her hesitate, but only briefly. Her bottom came within two inches of my mouth and I almost leaned forward and kissed her cheeks right there. Then her lower back was in front of my face and I knew if she wanted to she could ask me to move now. She was only two rungs from the floor and she knew I was still there.

Emily stayed quiet and went down to the bottom rung. Her bottom was just above my waist now and I could feel the air in the room had changed somehow. It felt a bit warmer than a few minutes ago. I swore she took a deep breath and stepped down to the floor. I held the legs of the ladder even tighter as her soft cheeks slid down my hard shaft. I heard her gasp when I pressed against her and it moved between her cheeks.

"Oh damn." She whispered. "W-what are you doing?"

"Just letting you feel the impression you've made on me." I whispered back.

"I was beginning to think you didn't notice. But still, I wasn't exactly expecting this." She shook her hips a little to make her point.

"Yeah I know. I don't know what came over me and maybe I shouldn't have pulled this on you." I began to back away from her.

"No no." Emily scooted backwards to me. "Stay there, please."

"I uh, I don't get you right now. Am I doing something wrong or right with you?" I was getting confused.

Emily thought for a few seconds. "Both I guess. Are you a virgin Brandon, like me?"

"No." I quickly responded.

"I didn't think so. I might be the only one in our class at this point." She pushed her hips against mine.

"Just so I'm clear here." I began. "Before I risk our friendship any more than I already have."

"We both have. I wore a skirt on purpose just to get a rise out of you." She moved to turn her body to face me and I let her.

I placed an arm on each side of the ladder and leaned in close to her.

"So what are you saying Em? You want me to take your virginity?" Even as I said the words it felt like my dick swelled even more.

"I'm saying that I'm comfortable with you Brandon, very comfortable. I've known you for about six years now and I figure if I couldn't lose my virginity with my ex of over two years than I'd like to lose it to someone I know. Before I go off to college of course."

"So you want to have sex, here in the teachers lounge?" I still sought clarification for some stupid reason.

"Well just promise me you'll go slow. Don't rush it and I'll see how far I can go. But if not here than somewhere else," she added, "with you, Brandon."

"Then turn back around." I directed her. "And follow my lead."

Em already knew what to do when she faced away from me. Her cheeks found my shaft and surrounded it between the two of them. I lowered my left arm to her flat belly and pulled her tight against me. With her only an inch or two shorter than me I found myself staring at her bare neck. I pressed my mouth against the space where it met her right shoulder blade and nibbled on her skin to garner a reaction.

"Mmm." Emily softly moaned, so I bit her harder. "Ohh yeah!" She moaned a little louder.

Encouraged, I slid my left hand up under her loose fitting shirt until I felt her bra. I palmed her right breast and spread my fingers out along the circumference of it. I could just barely fit it in my extended grip. I squeezed it and reveled in the feeling of her already hardened nipple pressing back against my palm. She moaned her approval again.

"Take off your shirt." I whispered in her ear and leaned my upper body back enough to let her.

Em's back was smooth and showed off just how fit she was. Not muscular, just in shape. I resumed nibbling and kissing her neck and shoulder while caressing her both breasts through her bra.

"Tell me Em. Cause I'm curious. How many lucky guys have you shown your bare chest too?" I was more than curious, I wanted her mind to be filling with thoughts about nudity and sex. I wanted her as horny as I could get her.

"Before now," she reached back between us and unhooked her bra, "only my ex." She let the unclasped bra fall down her arms and drop to the floor.

I loudly exhaled as I cupped her bare breasts, taking my time with each one. They were most certainly a handful.

"Well they feel magnificent." I stated.

"Really? But you haven't seen them yet. Want me to turn around?" She asked permission. So damn hot.

"Not just yet. But I have another question for you." I brought my right hand under her skirt and placed it at the top of her soft panties. "I think you know where I'm going with this." My hand slid under her panties and down her waist. I felt her bush and her inner heat. "Have you ever gone this far before?" My middle and ring fingers found the source of her heat and gently traced the outside edges.

Emily rocked her hips back into me as I stroked her. "Just once. We were spooning and I brought his hand between my legs." She writhed as the memory came to her. "I let him touch me like you are now."

Time to see if taking it slow had paid off or not. I pressed my two fingers against her outer lips and then easily slid them inside of her, up to the first knuckle.

"Oohhhh!" Emily sharply exclaimed. "But not like this."

Now I knew I had gone farther than anyone else, and it aroused me even more. I reminded myself to let my actual brain stay in control, for now.

I slowly thrusted my fingers in and out of her warm lips while still molesting her breasts with my other hand. Her body, caught between me and the ladder, had nowhere to go and preferred it that way. She kept herself pressed backwards against me and spread her thighs just a little more further apart. I did a quick clock check and realized Ashley had been gone about fifteen minutes so I should pick up the pace a bit. I let my left hand slide down her toned body and under her skirt. I pushed her panties down her thighs until they dropped to the floor like her bra had.

"Well if no one has ever treated you like this before," I forcefully thrusted my fingers in to make my point, "then I doubt you've ever been treated like this."

With my fingers still inside of her I managed to drop to my knees and push her skirt up with my free hand. I now had an almost perfect view of her bare round bottom. It was very smooth and shaped as if someone had taken a basketball, cut it in half, and used it as a mold for her. Truly enticing. So much so that I pressed my face against her soft flesh and kissed her, first on one cheek and then the other. She moaned her approval.

"You know," Emily began, "my first try with you didn't quite work."

"What do you mean?" I asked right before running my tongue up and down the space between her cheeks.

"Damn that feels good." She gasped. "I mean a few weeks back, that away game. Awww!" She cried out when I sunk my teeth into her. "I saw you had just finished off a big drink on the bus and hoped you'd head straight for the bathroom."

I could feel my dick bulge at this revelation.

"So I raced down the stairs to where they were and risked no one else walking in on me when I dropped my panties. I saw you in the mirror when you walked in and how you stared at me. Ohhhh, keep biting. And I wondered, what did I do wrong? Cause you left."

I paused for a moment before I responded. I would be truthful but delicate.

"Nothing you did was wrong. Had there not been others coming down the stairs it might have worked out differently that day. As it was I had to tell the others it was broken and to use the other men's room on campus. I basically saved you from about four other guys walking in on you."

"Well that makes seNSE!" She ended on a high note as I pulled her soft flesh into my mouth and bit down. "I was starting to think either you were gay or just not attracted to me."

"Well if you must know, it was enough to get a good rise out of me." I needed to bolster her confidence just a bit more. "Enough that I uh, took care of myself later that night." I hinted.

"You mean you ahhh," I licked her again, " you jerked off to me?"

I could smell her scent between her thighs. Just a little more and then I'd move on.

"Wouldn't be the first time." I commented before resuming my nibbling.

"Oh god I don't know why but that's really hot."

I stood up and quickly worked her skirt loose.

"It's hot because you now know that your body has a power when it comes to mine."

Emily moaned, "Ahh."

I picked her up in my arms and walked us to the couch.

"A power to turn me on, to arouse me." Her arms were wrapped around my neck and I felt her nails dig into me at my admission. "Your beautiful naked body is a magnificent sight to look at."

"You're just saying that." She said as I let her legs down, right next to the couch. "Cause I'm naked and you want to have sex with me."

Well she wasn't wrong. "Yes that's true." My admission made her giggle. "But your body is beautiful you know."

"Mmm tell me how." She stated as she sat down on the couch.

I knelt in front of her and noticed her naked boobs for the first time. They were very round and perky, probably barely even needed a bra to support them. Then there were her areolas. They were large too, I'd say about the size of a silver dollar coin and her hardened nipples stuck out a half inch or so, but were rounded at the tip.

"Your boobs are very enticing, they're soft and perky, a nice bounce when you do your cheers." She blushed but I pressed on. "Then there's your round bottom."

"Oh so you like my butt?!"

"Very much so. It's my favorite part, next to this of course." I placed my hands on her legs and guided them apart. Her blond bush was on full display for me and I took notice of its dampness. "This treasure you're giving me. This sultry and sexy pussy of yours. It makes me, well it just makes me hungry."