Sexual Awakenings Ch. 01

My other hand slid between her cheeks and over her asshole to reach her pussy from the other side. I pressed my left ring and middle fingers against those exposed lips and easily pushed them inside of her.

Ashley cried out in passion at the sensation.

"When's the last time you were touched like this?" I asked.

"You mean other than my own hand?" She replied. It was getting hard to resist her appeal. The young woman had a drive to rival my own. "It's been a little while I guess."

I stopped talking and focused on a steady upward thrust from my left hand. Ashley enjoyed the attention and moaned her approval every few breaths. My right hand stayed on the top of her inner heat, where her clit was, but I wondered if it could be put to better use. So on a downward pull of my left, I thrusted my ring and middle fingers into the top of her slit. I made sure to rub them against her hot clit.

"Awwww fuck!" Ashley exclaimed. "Fuck! That's MMMM!" She groaned as I repeatedly slid all four fingers in and out of her. "Fuck! Feels so damn good!"

Ashley continued to curse and grind her hips on my fingers. Then, out of nowhere, something came to mind.

"You uh, you didn't wear any panties today, did you Ashley?"

"You just, mmmmm, noticed?" She answered.

I thought for a quick second. "You wanted this. You wanted to get me alone today didn't you?"

"Yes!" She squealed on a particularly strong thrust. "But I didn't know Emily would, ohh! That you'd fuck her first. Guess I should've gone to lunch last." She quipped.

"Were you planning on coming on to me or just gonna see how the day played out?"

"Shh, after this." She commanded.

I continued my upward thrusts, alternating the fingers of each hand so when two slid out, the other two slid in. Soon enough her breaths grew quicker and shorter, like a runner out of breath. Beads of sweat formed in between her breasts and reminded me how her soft flesh has tasted. I lowered my head to one of her nipples and lightly pinched it between my lips.

"Oohhhh fffffuck!" Ashley yelled in my ear. "FUCK!"

I felt her legs try to clamp down on my hands, to keep my fingers buried inside of her. But I was stronger. My fingers flew in and out of her while she groaned aloud and cursed my name. Her legs trembled under the weight of her spamming body and I worried she might collapse. But all of her training as a cheerleader gave her strong legs because she made it through her orgasm standing up. As I watched her enjoy the climax I wondered how quickly I could get my shorts off and get her on the couch.

With a final inhale of fresh oxygen Ashley came down from the high I had given her. And she came down with a plan that differed from mine as I would soon find out.

"Ah, hmm, well," she began, "that was quite the pleasure ride Brandon. Now let me loose before my arms cramp up."

As I cut and ripped the tape from her arms she told me that she had planned on somehow separating her and I from Emily and outright ask me about a rumor. When I asked about the rumor she said she would find out soon enough.

She stepped free of the ladder and I gazed over her semi-nude form. Her tanned legs led to her curvy hips and up over her flat belly. Her bra and shirt had unfortunately fallen down and covered her tits but I knew I'd see them again before the day was done. A quick glance at the clock on the wall told me we still had plenty of time before we were due for inspection.

"Ok Brandon, first things first, or I guess, second." She giggled at her own joke. "Gonna need you to finish the trim so at least that job is done for the day."

I figured it was only fair and besides, it'd take me five minutes to finish the small section. So I selected a brush and a paint tray and brought them to the ladder.

"Oh but you're going to do this without your shorts on." Ashley added.

"Sorry, um, what?"

"You know you heard me." She sidled up to me and placed her hands on my hips. "But it's ok, I wanted to take them off myself anyways."

Ashley made quick work of my button and zipper. She threw the open flaps to the sides and pushed my shorts down to my ankles. All that separated my long bulge from her was the cotton boxer briefs I still had on. Now I wanted her to touch it, to take it in her hands, and pump it up and down.

"So the rumor about you is true as well. And I guess Emily wasn't exaggerating, much." She said as she stared at my crotch. "Good to know. Hurry up and finish Brandon."

I grinned like the horny schoolboy I was and turned to climb up. The smack I felt on my ass told me that Ashley's sexual appetite might not just rival mine, but surpass it.

As I thought, it only took a few minutes but when I climbed down I realized Ashley was gone. She had collected our clothes as well. I called out her name and got my answer.

Chapter Six - Principal's Office

"Will Brandon please report to the headmasters office?" I heard her on the school's PA system.

I made the quick journey to the office and practically burst through the closed door. The bright lights momentarily blinded me but I soon regained my vision. There was Ashley, with her top still on, sitting in the headmaster's leather chair. Both of our shorts were lying on the desk in between the two of us. It was a solid oak desk that took up the majority of the office.

"Come on over here Brandon." She stood up and waved me over.

Under the harsh glare of the lights I could clearly make out her bottom half and the blonde strip of trimmed hair that beckoned me to listen to her. As I approached her I let her put her hands on my shoulders, turn me around, and push me down into the chair she had just vacated.

"Oh, I left you alone too long." Her gaze dropped to my crotch where my limp dick resided under my briefs. She reached out to take hold of it and then stopped. "Actually let's see if I can prove the rumor about you true again while also disproving the rumor about my boobs again."

I watched, eyes glazing over, as she grabbed her shirt and lifted it above and off her head. Her pink bra, still unclasped, slid down her arms when she dropped them to her sides. Silently, she cupped her massive tits in her hands and massaged them, proving again that they were all natural. She pressed them together and held them to her chest. It wasn't long before my shaft hardened to its full length and all too soon Ashley stopped her show. She grabbed my shaft in her right hand and softly commented on it.

"See your rumor was that you were well-endowed. And every now and then a classmate would see a bulge in your pants but you never know if that's the true definition anyways. Then one of the basketball players I slept with happened to mention your size."

I gave her a quizzical look.

"Oh he's not gay. Just happened to accidentally see you in the locker room one time. But it's amazing what I can get a guy to talk about and admit when he's under my naked body!" Her blue eyes lit up. "And I must say that you are pretty damn impressive."

"Now before I go on I must know that you will let me return your favor." She half-turned and picked something up from the desk. As soon as I heard the tape roll unravel I knew she was making good on the promise from earlier. I smirked and willingly let her tie my wrists to the arms on the chair and even tape my ankles to the chairs legs.

"Excellent!" Her blue eyes sparked. "I already see the allure that you must've seen."

"I only hope I feel as good as you felt earlier." I replied.

"Oh trust me. I know you won't be complaining. After all this is probably the first time you've been tied down, huh?"

"Considering you're only the fifth woman I've been with, yeah it is."

"Only five?" She seemed doubtful but continued. "Well you're pretty damn good with dirty talk. Now about that large elephant in the room." Her voice trailed off as she lowered herself to her knees.

Ashley's hands went to my waist and hooked into my boxers. With a quick tug she pulled them down my hips and allowed all eight inches to bounce free. I lifted my ass up and she finished pulling them down to the middle of my thighs.

"Damn Brandon. Very impressive." She took hold of my shaft with her right hand. "I mean, I've seen your bulge before."

I gave her another quizzical look.

"You think only guys look at girls Brandon, and not the opposite? Sometimes I've even intentionally done things like bending over in front of guys to see their bodies react. And yours doesn't disappoint." She stated.

With her hand on the base of my shaft I watched Ashley lower her head over my waist. Her long and curly blond hair surrounded my hips and upper thighs. I could no longer see her but when her warm lips surrounded the head of my shaft it was my turn to curse her name.

"Oh, fuck Ashley." I exhaled.

She drew me in slowly and worked at least half of my dick into her wet mouth. I gasped in pleasure when her head bobbed up and down on the smooth skin and tightly sucked the head past her lips again and again.

"Goddamn you feel so good." I said to encourage her.

She broke her oral fixation but replaced it with steady pumps of her hand.

"That's right. You didn't really get much playtime today did you?"

"Ohhhhh." I groaned when she tightly squeezed my shaft.

"Good thing we're not in a rush, isn't it?"

Ashley lowered her lips and resumed sucking my shaft tighter than before. For me it was already the best blow-job of my young life. Granted it was only my third one but who was I to argue with myself. I was already on cloud nine and quickly getting brought up even higher. Involuntarily I strained to raise my hips off the chair and tried to fuck her lips. But she was stronger than me when gravity was on her side. Her left hand came down on my right hip and pushed me down to hold me there. I let her continue to suck and lick my throbbing shaft, knowing I would soon explode in her mouth.

Ashley could feel it coming to an end for me too. Her head bobbed even faster and her lips drew an even tighter circle and then... Then she took her mouth off and left my dick bobbing in the warm air.

"Ashley, what the fuck?" I asked with a trace of anger.

"I told you," she stood up in front of my face, "I even will guarantee," she pulled my thighs and hips forward, towards the edge of the chair, "you won't be disappointed." Then she turned around.

Ashley was right of course. For now I had her beautiful ass mere inches from my face. I had seen, thanks to a certain monthly magazine, my fair share of bottoms, in pictures and a handful in real life. And while Emily certainly had a very fine and very round ass, Ashley was in another class, not better, just different. Her heart-shaped ass was perfectly shaped. It wasn't round like Emily's but I could still get a firm grip and maybe even sink my teeth into it. Maybe even spank it.

Ashley lowered her hips over mine and spread her legs. I felt her soft bottom contact my stomach. With her back now blocking my vision I was again forced to only feel her actions. Her hand gripped my shaft and guided it, with heat-seeking precision, to her inner thighs. This time we both gasped as our bodies intimately connected with the others and she forced her body down onto mine.

As she buried my shaft inside of her a sudden rush of memories came to mind. All the times I had watched her practice cheers once basketball practice had ended, or playing co-ed volleyball, or any time I glimpsed her cleavage and mentally undressed her; they all came to me at once.

"You've no idea how long I've wanted you like this Ashley." I admitted.

"Really now?" She sighed. "Tell me why."

"Well to start with, mmm," I paused when she lifted and dropped her hips, "I could always point out that you're beautiful, your blond hair and bright blue eyes, ahh," she rose up and came down again, "or I could reference how you being a few inches shorter than me is very attractive to me for various activities, but hmmmm." I let out a long groan and stayed silent while she found her rhythm to control the repeated penetration.

"Go on." Ashley sternly whispered.

"Mmm but I've really wanted you because of your sexy toned legs and thighs. I've pictured you wrapping those legs around my waist and letting me take you against a wall."

Now it was Ashley's turn to moan.

"Ohhh fuck, that would be sexy." Her pace quickened on top of me and her hips slammed down with more and more force.

"But the one thing I've wanted most Ashley, the parts of your body that I just can't resist are your massive tits."

"Mmm I like them too." She admitted while her hips pounded down onto mine.

"I'd like to grab them right now and squeeze them while you fuck me. I can hear them bouncing against your chest Ashley. God I want them in my hands."

"Oh shit!" Ashley exclaimed.

I could sense her lean forward and open a drawer. She moved some things around and then leaned back against me. The cool sensation of metal rubbed along my arm as she cut away the tape with scissors on first one arm, and then the other.

I wrapped my left arm around the front of her and felt her soft flesh compress against it. I brought my arm under her left breast, cupped as much of her right breast as I could, and squeezed it as hard as I dared.

"Fuck!" Ashley yelled. "Oh god yes!"

Ashley's warm body bounced on mine in random, but rapid, movements. If she couldn't maintain a rhythm then she was probably on the cusp of a climax. I brought my right hand around to her front and draped it along her right thigh.

"I'm going to make you cum Ashley." I whispered through her deep groans.

My forefinger found her sensitive clit and firmly rubbed it. Her body convulsed against mine. In my position I didn't really have any leverage except for my arms. I held her tight and massaged her breast with one hand while I stroked her hot button with the other.

"Oh fu, oh fuc," then she took a deep breath.

"Cum on my huge cock." I said in her ear.

Ashley's toned body went rigid and her inner heat clamped down on my dick. It felt like it was being squeezed in the most pleasurable way possible. Then her mouth gave way to her own pleasure.

"MMMMM FFFFFUUUUUCCKKK!" She yelled loud enough to be heard anywhere in the school.

Then she was still. Which wasn't going to work for me. With her still on my lap and impaled on my shaft I reached down and picked up the scissors that she had dropped. I leaned sideways and just managed a quick cut on one leg followed by a second and I was free from my restraints.

Without a spoken word I braced my hands in the chair's arms and lifted myself up to a standing position. I moved slowly to keep myself inside of her and she was forced to lean forward and use the desk for support. I gazed over her bare back and alluring ass for a long second. Sweat glistened down her spine and led between her beautiful cheeks. She moved like she was going to stand up, but gave it a second thought and lowered her upper body till she lay flat on the desk. Well, as flat as her breasts would let her I suppose.

"Oh god." I heard her whisper.

"What was that Ashley?" I asked as I withdrew most of my shaft.

"I've uh, I was just thinking that I've never been in this position before." She admitted.

"Same here, but I can see why it's so appealing." I placed my hands on her cheeks.

"Mmm I bet you can." Her voice trailed off again.

I moved my hands to the bottom curve of her hourglass figure, right where I could feel her hip bones, and wrapped my fingers around them. It may have been my first time taking a girl from behind but I knew enough to hold her as steady as I could. Last thing I wanted to do was slide out and injure her.

"Ready?" I asked to no response.

I slowly, but firmly, pressed myself forward, all the way back into her inner flesh. Ashley parted her legs a little more and welcomed me in until I was buried inside of her. Then I heard her whisper again.

"Sorry, what did you say?" I asked.

"I said, I guess it's your turn to cum now?" She repeated.

"You don't think you'll enjoy it?" I curiously asked.

"Between your fingers and then sitting in your lap the way I did I'm doing alright with enjoyment. Besides, you've earned your time." I could practically hear the smile on her face as she spoke.

I pulled back and thrusted my shaft in her, harder this time. We both grunted at the renewed sensation. I looked down at her beautiful ass and watched it while my hips moved back and forth. The feeling of her tight pussy surrounding my long dick, coupled with the sight of her ass jiggling with every thrust was mesmerizing. No, it was intoxicating.

I couldn't look away and wished there was a way I never had too. This hot piece of ass had filled my mind at night, and intentionally teased me during school. The fact that she was the cheer captain, had a hourglass figure, and had a huge set of natural breasts was all icing on the cake at the moment. Because in that moment I had arguably the most popular girl in school bent over in front of me, completely in my control, after having just fucked her best friend.

The thoughts ran through my brain and drove me to a higher state of arousal. My thick cock repeatedly penetrated her pink flesh at an ever increasing rate. Her body was being rapidly pushed back and forth against the oak wood but she never complained once.

I never knew how badly I wanted Ashley until this day. How I wanted to undress her and feel her against me. To have her on top of me and watch her face as she took my manhood inside of her. The need to pick up her light body and hold her against a wall while I fucked her.

Then a familiar feeling came over me. From my waist I could feel an internal heat build and knew I would soon experience a sweet release. My thrusts became stronger and longer. All I wanted to feel was the smooth tip sliding along the inside of her pussy. My body tensed in anticipation

"MMM!" I grunted and gave a final thrust. "Fucking hell!" I exclaimed as the white-hot cum erupted from my shaft.

"Mmm I can feel it." I heard Ashley say from what felt like a ways off.

Each shot pulsated through my shaft and exploded into her. I stayed still while I emptied myself into her and watched as her hips rocked back and forth against me.

"All done back there?" Ashley asked in a sweet voice. "It feels like you are."

My only response would have been to collapse forward, on top of her, or backwards into the leather chair. I chose the latter. Ashley groaned as I unceremoniously slipped my dick out of her warmth and fell into the chair with a loud sigh of exhaustion.

"Oh thank god," Ashley began, "I think my boobs were about to start chafing from your grinding." She turned around with a smile but saw the concern on my face. "I'm fine, Brandon, more than fine actually."

"I'm more than fine too if you're wondering." I grinned.

Ashley sat down on the desk facing me. "Like I even need to wonder. You just fucked me AND you did it on the headmasters desk, while staring at my ass. Yeah, like there's any doubt." She smirked.

"How did you know I was staring at your ass?"

"Where else would you look? Now hurry up and get dressed. We need to clean up before dumbass comes back." She reminded me on her way out of the office. "You know, I'll never look at this office quite the same way."

I stood up and followed her down the hall, "You plan on being called in there again with only two months left of our senior year?"

"Well I still don't plan on attending Friday chapel, do you?"

I thought for a quick second, "No, I don't."

"Exactly," she turned to face me at the entrance to the freshly painted lounge, "cause what's the worst he could do to us? Give us another weekend detention?" She had a Cheshire grin on her face now.

I palmed her ass and pulled her close to me. "I sure as hell hope so."