Size Does Matter Ch. 01

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He was a nerd, but his size definitely changed my mind.
4.6k words
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Part 1 of the 2 part series

Updated 06/08/2023
Created 03/26/2017
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How could I have guessed that the nerdiest guy on campus would turn out to have the most magnificent cock I had ever seen and be the best lover I could have ever hoped for.
Yes . . . size does matter!

**************************************

"Geez, who knew?"

I'm here in his bed, watching him in the bathroom. He just stepped out of the shower and feeling me watching him turned and grinned that wide toothy grin that I love and that never fails to get me wet in anticipation. He's tall, with a runner's body, broad shoulders, slim hips, 185 lbs., twenty-six years old and his name is Jacob Liebowitz. Add to that, Jacob is a member of MENSA, from a good family, the second oldest in a family of four boys and has the potential to one day be a very wealthy man.

Oh, did I mention that he is the king of the nerds, that he was untouched and unsullied until he met me and I "took" his virginity, or that he has the longest, thickest, most beautiful cock I've ever seen or experienced?

As he stands there at the sink brushing his teeth, his cock is hanging long and heavy between his legs; my clit becomes achy with desire knowing how it could transform in just a few seconds into a hard, fully engorged appendage that strikes fear in the hearts of young impressionable girls like me. To the woman who first asked the question, "Does size matter?" my answer is a resounding YES! If his dick hadn't been so long, thick and delicious looking I've often wondered would I have been attracted to him?

Sometimes, particularly on a morning like this one, I'll go into the bathroom, and he'll let me hold it for him as he pees. We'll both laugh and giggle like two naughty children, but the giggles don't last for very long. As the last few drops fall from the tip of his cock, I'll slide it into my mouth and suckle him until he starts to grunt and thrust, spraying cum down my throat. He loves that.

He says emotionally the feeling of being loved and wanted, coupled with the physical sensation of having his dick milked by a beautiful, desirable woman is beyond description. He says he does his best and most imaginative, creative work on those days when I send him off to work happy and satisfied after an early morning blow-job or quickie fuck.

Funny, I don't think it was until after Jacob and I got together, that he realized what an exceptional cock he had.

*****

My name is Cameryn O'Donnell. I am twenty-one, attractive, smart, good upbringing, and a bit self-absorbed. Through high school, I was one of the popular girls. My time was taken up with my girlfriends (who were clones of myself), cheerleading, drama club, ski club, travel club, and of course my boyfriend, Stephen. As expected of someone like me, Stephen had been the captain of the football team while in high school and after graduating, he quickly became a star on the University's football team as well.

During high school, of course, I had my cliché of friends, but I can honestly say that I don't think I ever deliberately set out to be mean to people (nerds, goths, geeks, etc.). I know it sounds horrible, but there were some people who didn't matter to me; people I saw, but didn't see. Truth be told, I really didn't lose a lot of time or energy worrying about people I didn't know or have anything in common with, like the geeky girl with the thick glasses and stringy hair, the skinny guy in the too short pants, the nerds who always sat together during lunch, for example. Does that sound mean? Anyway, those attitudes began to change when I went to University.

After I had graduated high school, I was accepted at the same University as Stephen, and within a week of my being away at school and on my own, I had sex with Stephen, in my dorm room. Though it was my first time, it was obviously not Stephen's, which did not surprise me. After all, he was a few years older than I was and since I wasn't putting out back then, I had suspected he was getting it from someone, (probably that skank Tiffany).

After that, we had sex regularly where ever, whenever we could throughout my freshman year. Stephen was my first serious boyfriend, and just as self-centered as I was. As I say this, an incident immediately comes to mind that showed Stephen's foremost concern was to satisfy himself and to meet his needs and desires first. This should have been an early red flag.

Stephen wanted us to go on a spur of the moment trip to Spring Break with his friend Peter and Peter's girlfriend of the week, Tiffany. Unfortunately, the only accommodation available on such short notice was a room with two double beds that Stephen suggested we could share. I didn't like these arrangements because Peter had always creeped me out and I wanted nothing to do with him, but not wanting to argue with Stephen or spoil our trip, I finally gave in and agreed to share the room.

We went to dinner and then enjoyed a little partying afterward before we returned to our room and fell into our beds exhausted and a little drunk. Around three o'clock that morning, still groggy from the alcohol and half asleep I felt Stephen poking me from behind and easing his knee between my thighs opened them wider. With my leg resting on top of his, he reached down, positioned his cockhead at the entrance to my pussy, and pushed forward and inside me.

"Mmmmm," I moaned, irritated but still struggling not to wake up totally.

"Shhhh . . . ." he whispered in my ear.

"Oh God Stephen, don't, they can see and hear us," I said.

"Shhhh," he said again and pressed up into me a little harder, his cockhead and half of his shaft sliding further into my resisting pussy. Stephen began to stroke, and in discomfort, I tried to squirm away from him.

"Damn it, Stephen, stop!" I hissed at him, now fully awake.

"Shhhh, he said again. Not so loud. Just be quite, relax and enjoy the fuck. Hell, I can already feel your pussy getting wetter."

"Get off me!" I said to him a little louder than I had intended. I was not sure if I was more pissed with his infuriating attitude or with the roughness of his intrusion.

"Alright, alright," he said even as he continued to stroke with a slow, steady motion until I felt his balls lightly tapping against my ass. He had his entire length buried in my pussy by now and somehow had maneuvered me onto my stomach and was riding me from behind. He began thrusting harder and deeper, having covered my mouth to quiet me. Giving up trying to struggle with him, I was no longer protesting but was resigned to let him use my pussy so that I could go back to sleep.

Despite my initial reluctance, the friction of his cock moving in and out of my pussy rubbing and pulling my clit ignited an orgasm, and I could feel it building and building until I exploded. Stephen's pace increased, and I could tell he was on the verge of cumming.

"Stephen, Stephen . . . don't cum inside me," I mumbled into the hand that still covered my mouth.

"Don't cum in me," I managed to repeat, just as he erupted high up inside my unprotected pussy, unloading two thick blasts of cum.

"Please God, please don't let me get pregnant," I thought as he ground his hips into me one last time before rolling off saying, "Damn, baby I'm sorry. You felt soooo good, I didn't mean to cum inside you, but I just couldn't help it."

"Yeah, right," I said sarcastically before getting up to clean myself. As I walked into the bathroom, I could feel Stephen's cum already beginning to leak out of me. When I entered the bathroom, I turned and casually glanced across the room only to see Peter sitting up in his bed with his dick exposed, jerking himself as he looked straight at me, he had heard and seen everything.

With embarrassment and repulsion, I quickly went into the bathroom and closed the door.

*****

By the start of my junior year, I had broken up with Stephen and started dating Marc, one of the top players on the school's nationally recognized golf team. It was around this time that I was called in for a meeting with my academic advisor to discuss my grades. Obviously, there had been too much partying and not enough studying, and I found myself in jeopardy of being put on academic suspension. My advisor and I agreed that with a bit more focus I could bring my grades up, but that it would probably be a good idea if I got some tutoring with my philosophy class.

It was on the recommendation of my advisor that I contacted Jacob Liebowitz. Jacob was a graduate student and teaching assistant who was temporarily tutoring students to earn extra money. From the very beginning, I disliked Jacob. Granted he was brilliant, but he was also condescending, misogynistic and maybe worst of all, a nerd. The day we met, he was wearing a pair of too tight jeans, a red and black plaid short sleeved shirt buttoned up to his Adam's apple, the proverbial pocket protector, big black rimmed glasses, and brown wing tipped shoes. Although I couldn't see it at the time, I later realized he was actually a nice looking man. Physically, he had thick, dark wavy hair that was too long and in desperate need of a hair stylist; piercing but sensitive grey eyes that were hidden by big, dark rimmed glasses, and a physical countenance of strength and determination that was disguised by his awkward, uncoordinated attire.

We disliked each other right off. Jacob's continued rude, condescending attitude and antagonistic behavior towards me sometimes brought me to the edge of tears and hurt feelings. Despite the drama, all things considered, my being tutored by Jacob had academically been the right thing to do. By mid-year I had broken up with my boyfriend Marc, my grades were on an upswing, and I could see an increased understanding and improvement in my philosophy class. I slowly began to see Jacob in a different light, he was still rude and condescending, but I did sometimes notice a softness in his tone when we talked and occasionally would catch him staring at me when he thought I didn't notice.

I remembered when I received my philosophy progress sheet and saw that it was marginally better than I had expected, I impulsively threw my arms around Jacob's neck and hugged him. I may have been mistaken, but I swear I felt something pressing against my thigh. When Jacob realized he was having an erection, he pulled away, turned and hurriedly left the room leaving me staring after him.

Was he embarrassed? God . . . he was such a nerd; I briefly wondered if he had been with a woman before but quickly dismissed the thought. Despite being the king of the nerds, Jacob was a twenty-six year old, reasonably good looking man, and the thought he had never had sex with a woman was ridiculous.

One evening during a tutoring session, I was sitting at my desk going over a paper I had written. Jacob, sitting across from me took his glasses off casually, and for not the first time, I noticed how handsome he was. Grey eyes, a deep cleft in his chin, rugged features. Watching him, I felt myself becoming aroused. At the end of the evening as he packed up to leave, following an impulse I went to kiss him on his cheek, but he turned his head, and I kissed him full on the lips instead. The kiss lasted that second or two longer than it should have, and this time it was my turn to pull away and look at him confused.

*****

As the end of the school year approached, the sexual tension between us was undeniable, but neither of us spoke about it. I don't know exactly when the dynamics of the relationship changed, but I realized they had, if not on his part, definitely on mine. My last tutoring session was scheduled for three o'clock in his office, to be followed at four by a Skype meeting with my cohort study group that included three of his other tutorial students. As the four o'clock session began and Jacob settled in behind his computer monitor, the others logged on one by one. I sat across the room watching, listening and taking notes as he addressed the gathered cyber group.

It had been at least two months since I had been with a man and sitting there watching Jacob, I could feel myself becoming aroused. I recognized the all too familiar achiness between my legs that I would have when I wanted sex with my old boyfriend, Marc. I put down my note pad, and without saying a word, I stood and removed my blouse, my breasts on display for him. I saw his gaze self-consciously shift from his monitor to my 36B breasts, high and firm with quarter sized areolas and long, dark nipples that were now hard and erect. Raising my hands to cup and fondle my breasts I closed my eyes, amazed at how quickly my nipples had turned into hard peaks and how this nerdy professor brought out the slutty side of my nature.

Standing on the other side of his desk, I watched as his eyes shifted from the monitor to rest on my breasts. He held his breath and then quickly exhaled as he struggled to resume his lecture. Holding his eyes with mine, I fondled my breasts and smiled seductively at how easy it had been to excite and distract him. I sat down in the chair opposite his desk, and it may have been my imagination, but for a moment, I thought I saw what I could only describe as panic on his face that quickly changed to anticipation. From the chair, I slipped to the floor, onto my hands and knees and began to crawl under his desk toward him. As I drew closer to him, he somehow managed to pick up his online conversation with his students. I slowly crawled toward him, and though he initially presented half-hearted resistance, he eventually relaxed and allowed me to open his legs. I let my hand run lightly along his inner thigh and with my right hand caressed the hardening length of his cock. I buried my face in his groin and inhaled the scent of his manhood and growing arousal through the fabric of his pants as I covered his captive cock from tip to base with kisses.

I could feel the subtle movement as his hips pressed against my mouth. I pulled away, looked at his growing erection, and noticed the small circle of dampness where his cockhead was now leaking pre-cum and staining the fabric across his thigh. I crawled between his knees again, but this time reached forward and unzipped his pants. His cock was hard, but I managed to free him and watched in pleased surprise when it sprang up, long, thick, uncircumcised and eager. My mouth opened in readiness, and slowly rubbing his cock with my hand, I eased the head between my lips, red lipstick smearing down the shaft.

I took my time and licked him like a lolli-pop, up and down in long, slow licks as one at a time I freed his balls and took them into my mouth to suck gently. I pressed my tongue against the underside of his cock and teased its length, lingering over the thick pulsing vein. Working my way up his cock, I pulled back his wrinkly foreskin and with my tongue swirled around his cockhead before guiding him deeper into my mouth. I heard him moan and stopped pleasuring him fearing his on-line students had heard him. There was silence, and then "Mr. Liebowitz? Mr. Liebowitz?" The sound of the student's voice got Jacob's attention and brought him out of his reverie. Jacob regained his composure and resumed talking, and I went back to sucking his cock.

I took his entire cockhead into my mouth and began to stroke it in and out. His cockhead brushed across the roof of my mouth, and against the back of my throat until it haltingly slid down my throat. I held him, letting my throat contract and release around his cock and began to move my mouth up and down his cock gradually increasing my tempo. He couldn't talk clearly, and I could only imagine how his students must have been staring at him in concerned silence as he finally stammered out, "session dismissed for today, we'll continue tomorrow at three o'clock." Jacob had abruptly ended the session without question, and with a shaking hand managed to turn off his computer.

Jacob spread his legs wider for me, and his hands slipped down under the desk to become entangled in my hair. One hand reached around to the back of my head pressing my mouth further down his cockshaft until the full length was nestled tightly inside the warm, moist sheath created by my mouth and throat.

I'll never forget how it was that afternoon between his leg, feeling the warmth and strength of his growing erection. It was obvious he was extremely excited by the way his cock jerked so hard in my mouth, I was afraid he was going to cum. I backed off his cock and began fondling him between his legs, running my hand along the length of his cock and the insides of his thighs. I took hold of his cock and began to squeeze and stroke it. From the way he groaned with pleasure, I could tell he loved the feel of my hand on his dick. I would squeeze and release, squeeze and stroke his cock forcing it to become longer and thicker in my hand. Jacob couldn't help himself, and soon couldn't hold back the moans of pleasure and finally gave in to the exquisite torture as I jerked him. Sensing his readiness, I increased my rhythm until he was on the brink of exploding. With a final hard jerk, I pushed his engorged, throbbing cock back into my mouth just as he lost whatever control remained and he began to ejaculate in several long spurts, spraying cum down my throat leaving me no option but to swallow all he could give me.

"Oh my God, Cammie," he kept repeating in a low, hoarse whisper. Finally pushing back his chair from the desk he pulled me into his lap, kissing me hard, deep and hungrily, tasting his cum on my lips.

*****

I sat in his lap, his now semi-hard cock pressed between my ass cheeks, his mouth sucking eagerly on my tits. My attitude toward Jacob had gradually changed, and listening to him talk, so had his. Jacob said that over the last month or so since we had kissed that day, being around me, smelling my perfume, seeing and touch me would leave him feeling unsettled. Clearly embarrassed, but almost compelled to speak, he said he had started having wet dreams. Like a pubescent school boy, he'd occasionally awaken during the night as copious threads of hot cum shot out of his cock making a mess in his boxers. The first time it happened, all he could do was groan in disbelief and embarrassment knowing he had been dreaming about having sex with me.

I could feel Jake getting hard as we talked, and began to move off his lap when he surprised me by suddenly confessing that he had not had sexual intercourse with a woman before. Even though I had begun to suspect this anyway, I was still surprised to hear him say this.

By the end of the school year, despite my reluctance to be seen with Jacob, we had quietly begun to date, but I didn't want my friends to know, I mean how would that look? One of the most popular girls on campus and the super nerdy teaching assistant being seen out together. Whenever we were together the date would end with us satisfying each other short of fucking. Mutual masturbation, my giving him oral sex, him giving me oral sex. For a while, this seemed enough for us, but I quickly saw that it was not; despite his being a virgin his sexual appetite was freed and wouldn't be satisfied until he was able to bury his cock inside me. Though I tried hard to deny my growing desired for him, I could feel myself weakening. I still couldn't see myself having sex with such a nerdy, unsophisticated guy, but like Jacob, I knew that we would have sex sooner or later.

I underestimated Jacob and his persistence. I remember how it happened the night he had sex for the first time. I was at home, had just stepped out of the shower and was standing naked and wet in front of the bathroom mirror combing through my wet hair when the doorbell rang. The bell began ringing so insistently that I threw on my robe and ran to the door. Looking through the peephole, I saw it was Jacob, and though surprised that he would come by unannounced I opened the door to let him in.

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