The Good Guy Always Loses

Thanks for choosing to read my story everyone! I hope you enjoy!

Please forgive me for any spelling or grammar errors. I proof-read the story several times, but sometime these things slip through :S

DISCLAIMER: "This is a completely fictional story. All of the characters are fictional and any resemblance to anyone in the real-world, is purely coincidental. The characters, though fictional, are also all over the age of 18. Needless to say, this story contains heavy and highly erotic sexual themes and imagery. Thank you."

Without further ado let's begin the story. ENJOY!!

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This is the story of how I, Jeff, a good, decent guy, had my heart and soul torn in two and finally ended up being cuckolded.

CHAPTER I: INTRODUCTION AND EARLY EXPERIENCE

In my final year of college in UMass I had moved off campus into my own house and paid all the rent, utilities and other expenses, using the money I got from work, and some from my parents. I was a mail-room attendant at the nearby dorms, where students picked up packages and so on, but was looking for a more fulfilling job.

Since it was my last year, I had few classes and dedicated most of my time for work, so any extra hours or late shifts I could pull were taken advantage of, and that's more money made. It's not like I was barely scraping by, but hey, I wasn't a CEO either. I hadn't even remotely considered how I would pay-off student loans yet, so yea, I basically faced the problems any regular college student would. My brother, James and sister, Stacey, went to school here in Massachusetts as well.

I was born into a non-spectacular family, where my brother and I were the same height, and while I didn't know anything about his, my dick was quite small, around four and a half inches.

My sister was an unknown beauty. When I say unknown, I mean it is unclear where she got her looks and body from. She was a beautiful girl with striking green eyes and had a great hourglass figure, with D-cups.

Now I definitely do not have constant incestual thoughts about her, but did have a strange run-in with her once. I was "fortunate" enough to have been in her room when she came out of the shower one day with her back still turned to me, and she dropped her towel.

She was still fiddling in her drawers for the clothes to wear, when she bent over quite far, enough to give me a very uninhibited view. She seemed to stay there for an eternity, an eternity of me just staring into her flawless crack. When she finally turned around and saw me, she jumped a little, causing her D-cups to jiggle quite generously.

"uuhhh... I..uuuhh..." was all I managed to croak out, before we spent a good fifteen seconds in awkward silence just staring at each other, her into my eyes, and me at her perky tits and perfect figure. After slowly picking up her towel and holding it at her side, she gave me an inquisitive eyebrow raise, sort of asking me "What are you still doing here?"

Not knowing what to do, I just continued to stare at her beautiful tits.

After an inappropriate wait, I finally mustered the brainpower to say "Sorry, I uhh..." and quickly left the room. That night I stroked my small penis to her for the first and last time.

When I realized my door was open, I freaked. She was standing outside watching me for the entire session, out of range of my view, until I got up, and creeped to the door and saw her. This time it caused me to jump back to the middle of the room and my little worm to wiggle.

She walked into my room, slowly and deliberately. The moonlight caused her catwalk like strut to make my dick stand on end. She looked into my eyes the entire time. Completely unsure of what to do I stood there dumbfounded, with an erection, as my sister walked up to me. After thirty seconds of staring into her steely eyes, she finally proceeded to look down at my dick and back up into my eyes.

She then took the index finger of her right hand and placed it under the head of my penis and bounced it up and down a couple of times, after which she just rubbed under the tip a little. It was very sensitive, and given the highly erotic scenario, I immediately jizzed a decent amount of spunk onto the entire length of her finger and felt a shudder run through my body.

She gave a humorless chuckle and looked deep into my fully dilated pupils. "Are you proud of yourself, jerking to your sister?" she asked softly.

"I...no I swear I wasn—" I stopped short, unaware of how to rectify the situation.

"That's what I thought... Disgusting, you should be ashamed," she said. I felt a little hurt inside, but understood.

After an uncomfortably long period of her studying my shrinking cock, her eyes softened and she tenderly whispered "shhh..." She reached out and held my hand with her left one, and brought the finger with my cum on it to her mouth and sucked it clean. The strange mixture of feeling her silky soft hand holding mine, and witnessing the lewd sight of her patiently sucking the cum off her finger, caused my cock to grow very hard again and curl upwards a little.

Upon seeing this, she gave a slight smile and told me it tasted good, probably due to my good diet. She gave another smile, a pleasant one this time, before proceeding to tell me, "this never happened," and that it would never happen again. I quickly agreed and watched her deliberately walk back to her room, looking back occasionally to lock eyes with me and give another one of those devilish, "boner-causing" smiles.

I jumped straight back into bed and that was the end of everything. That was before we broke for college and we never saw each other again without the presence of our family members, so it never came up or affected me after that, mainly out of my unquestionable respect for her.

CHAPTER II: JENNY AND TODD

Around two weeks into senior year I had gotten somewhat used to my schedule and classes, and could spend a little more time paying attention to other things, as opposed to figuring out where and how to get to classes, navigating the route from my house to work etc.

One thing I did notice was the small "communities" formed by each year group and major. Of course the senior year group was the smallest, because people were very spread out by then, so in these small communities people knew each other pretty well, or at least passed by nearly everyone regularly.

I was a diligent and hard-working student, like many others in our school, but it was clear that I had certain insecurity issues. Now, I was an unspectacular American guy, roughly 5'10" but I wasn't very well built. I wasn't fat, on the contrary in fact, I was a little skinnier than I would like to have been, with almost no muscle mass. So needless to say, I didn't get much attention from the girls and bad attention from the guys.

My insecurities stemmed from the fact that I was in the major of Psychology, so the demographic of people I went to school with, in my classes etc. was a little skewed. My class year and major was riddled with the huge, muscular albeit dumb jocks and their female counter-parts, plastic-as-fuck, dirty skanks.

As you would expect, the conversations amongst the girls generally ranged from make-up, boys and vampire diaries to the occasional under the breath comparison of their sexual escapade's dick sizes, where they would generally praise the monster cocks and put down and laugh about the tiny dicks. The conversations amongst the guys generally ranged from sports, "fucking some bitches," protein shakes, and even their own dick-sizes, where they would literally compliment themselves, while putting down the guys who they assumed had smaller dicks, regardless of whether they said it to their faces or not.

I've even heard some of them pointing and whispering about me under their breath when they thought I couldn't hear them, talking about how they wanted to "bet" I had a tiny prick. Additionally when these douches would walk past their skank counterparts, these girls would do the same thing, whispering under their breath "not-so-subtlety" about how they bet each has an enormous dick and giggling when the guys would look at them.

The guys would just walk past with a shit-eating grin on their face, winking or pointing at the girls. Their heads would just be filled up of steam, and these giggling girls would constantly feed and stroke their egos, to the point these douches would walk around feeling like gods. I hated seeing it, and it was a vicious cycle that got worse with every progressive year.

I on the other hand, had only had sex on two occasions in the past, and both were when I was of legal age and of course, both were unspectacular. I was actually glad I ejaculated relatively quickly and finished it up. They were embarrassing encounters to say the least.

So as you can imagine, this didn't do much to help my confidence, especially when I would be constantly reminded that I was in the minority of small useless guys, by both the douches and skanks, every time I walked by them. It was rare to find friendly guys and nice, non-materialistic girls.

Even if there were friendly guys, depending on their size and structure, they would soon either be turned into one of the douchebags, or a social outcast. A similar process took place with the girls. All girls start of nice, but the unattractive ones, become outcasts and the pretty, cute girls, slowly become dirty whores after constant exposure to the douches and other whores. This was a far more disturbing transformation in my opinion, because it symbolized the destruction of innocence and served to prove that all good things will fall.

It was difficult to find a good girl who was pretty and friendly. This was the mindset I went into my final year with and it was confirmed for the most part in the first two weeks, that is, until I met Jenny.

Jenny was in my lab class and partnered with me for the semester project. She was a strikingly beautiful girl, with light blonde hair and gorgeous blue eyes. She had very light skin, but not the disgusting pale type, rather the serene angelic white, with cute freckles and an amazing body. Her breasts were not anything special, but not flat chested either. She had a somewhat frail structure and overall a very innocent and celestial look to her.

What enthralled me most about her however was her demeanor. She was unconditionally kind and didn't hang out with the skanky girls. She was very friendly with me and seemed to be very diligent in her work habits, which almost got me convinced that she could be the one-in-a-million we all look for.

She was very attractive, but without the pounds of make-up, massive breasts and overly bitchy attitude that most attractive girls inevitably get. People definitely noticed. I heard whispers from douches all round, of how they would completely wreck her, milk her, or "stretch her sweet holes," or some variation of that sort. One even said that he would make her his "sweet little cum bucket." It infuriated the hell out of me, but she didn't seem to notice, and I wasn't about pick a fight with one of those huge guys.

Even the skanks seemed to whisper negatives about her, suggesting how her good girl shit was just an act and she was a slut underneath. 'Jealousy is a funny thing' I thought, these girls finally came across someone who outclassed them in every way imaginable, so they had to try to bring her down to their level through silly rumors. I paid no attention to them, because unlike the douches, they were not an immediate threat to her.

I would be a liar if I said I didn't think about her erotically, even if it was a very rare thought. Her beautiful white skin and golden hair, entwined with her haunting blue eyes were hypnotic. I would picture how good she would have looked naked, just lying on my bed, allowing me to just gently touch and play with her. My thoughts would always be gentle though, and I would never think about hurting her, only loving her. I also occasionally fantasized having a huge cock and making her gasp when I took it out. She would just spend hours marveling at it, while she sat in my lap and I sucked on her nipples or rubbed her thighs.

I immediately noticed how shy she was. This made her even more attractive in everyone's eyes, especially mine, because a quiet, smart, attractive girl was one I would want to spend the rest of my life with. I wanted to steal her away from here and bring her to a land with grassy fields, beautiful sunsets and where it would only be the two of us. That way she would never have to face these morons and would stay the naive, cute and innocent girl she was forever.

She would be very polite to me and everyone else around her, and would never respond to nasty comments other bitches said about her. Even when the douches came up to hit on her, she would just blush and shy away, then continue about her work. I absolutely loved it.

Luckily we had roughly the same schedule, so I could ask her to have lunch with me to "discuss class" without the context of a date. But when I would call her to ask her, she would knowingly giggle softly, as if she knew what I was up to. She didn't protest it, so I didn't bring it up further, just enjoyed her company.

We became very friendly and close over the following few weeks. This in turn caused me to be the target of many of the douches, because they thought that I was keeping her away from them, so they couldn't have their way with her, which was somewhat true, but I definitely did not see her falling for one of those obnoxious guys.

I also became acquainted with another person in my class, who's name was Todd. This was a far less amiable acquaintance, and Todd was seen often as the "Douche of all douches." He had a big strong build, at 6'3" and 230 lbs. He was also very good-looking as well, obviously. He expressed heavy interest in "plowing" Jenny from the beginning and if it wasn't for me being a pussy and occupying her time, he would have gone through with his attempt.

Occasionally when I would walk around, he would purposely walk into me and push me, which would result in me being winded, stumbling back and sometimes even falling over, dropping my equipment. He would call me "small-boy" and "tiny-dick" often as well. Upon hearing and seeing this, many of the other guys would laugh and the girls would giggle, in which case Todd would look at them and give that "douchey" grin so they would receive validation on their enjoyment. It was feeling like high school in my class again!

But I thought nothing of it because Jenny would never laugh, usually just avoid Todd's eye contact, because in the end, he was doing this because of her, and I had a feeling she knew that. Todd would often try to look at her after a situation like that to see her reaction. I assume it was some form of stating dominance over me and showing her he was big and strong. She would simply blush and look away, a reaction I felt came from her knowing she caused it, and also from not wanting to give Todd the satisfaction of looking at her.

Sometimes I would fall over and admittedly it was quite funny as I rolled like a fool, and everyone including Jenny would giggle, after which Todd would be ecstatic and look at her. As usual she would blush heavily and look away, but even that was enough to hike up Todd's ego, which would make him bolder. Jenny would usually always come to help me up, unless it occurred far away from the desk we sat on, in which case she would just look over and appear concerned.

Once when such an event occurred and I fell over particularly clumsily, everyone almost burst out laughing and truthfully, I laughed a little too, it must have looked very stupid. I looked over at Jenny who was holding her mouth while she laughed and I felt happy knowing I made her laugh. Todd immediately looked over at her too and I assume, she didn't look away because she was too busy trying to contain her laughter, but Todd looked directly at her and he made eye contact.

Her giggling slowly subsided to just a pleasant smile and I could just see Todd's ego blowing out of proportion in his head. The eye contact lingered and she finally looked away blushing heavily, still smiling. Todd walked away victorious. 'What an idiot' I thought, 'He gets excited because she didn't look away, even if she couldn't help it.' I laughed at his stupidity silently in my head as I walked back towards my table.

This was a big lecture hall with many lab assistants, so it took a good 30 seconds to get to your seat at the least. On my way over I saw Jenny stealing glances towards the other side of the room. I could see her eyes following something all the way across to where the exit door was and every time she stole a glance she would smile and blush a little before looking back down at her lap.

I was approaching my seat and would be able to see what she was looking at, but there was a big support pillar right next to our table so it blocked my view of everything on that side until I literally got around it and sat down next to her. Just as I was rounding the pillar I saw her look up at the corner again and give the cutest shy smile, quickly blush then look down again, and I finally came around the pillar to sit down, only to witness the exit doors swinging. I thought nothing of it and continued into the class and got my mind of it by chatting with her. A minute and a half or so into the lecture I saw Todd, re-entering through the exit doors. Again I thought nothing of it and just continued with class.

Jenny and I continued our routine of meeting up for lunch and studying for lab, and Todd continued his silly "dominance" routine. More and more often, I would see Jenny looking at the "mysterious figure" moving towards the exit, while I trudged up the stairs to my seat past the pillar. She would progressively smile more and have longer eye contact with the person while blushing and smiling, then looking away. It was timed so perfectly while I was walking up the stairs and besides the support pillars blocking my view, almost as if it was planned that way. When I asked her about it, I tried my best to seem curious rather than confrontational and she just told me it was her friend. I accepted it and just kept going.

Lots of people would visit the bathroom throughout the length of the class, but I noticed an increase in the frequency of Todd's bathroom visits. As he walked to the exit he would be looking at our table, to which I would look at him and gesture 'What?' with my shoulders. He wouldn't react, so I would turn and look at Jenny, who quickly tried to mask her smile, and look at me with a curious expression. I would smile back at her, assuming my shoulder shrugs at Todd were funny to her and we would both giggle a little. As I would look around at some of others in the class, they would look at me and shake their heads, as if they were chastising my stupidity.

On one of the days where we would have our regular lunch "dates" I couldn't make it, so I asked her to dinner instead, and she somewhat hesitantly said, "um... sure." We made it to dinner, in a place close to my house and we enjoyed a nice Italian meal, for which I paid, after much persuasion on my part.

I managed to convince Jenny to come back to my house for a quick drink. I had just turned twenty-one and was eager to show off my alcohol collection to impress her. We got a little tipsy and were watching some stupid videos. I finally mustered up the courage to lean over and kiss her. After a little bit of hesitation on her part, she allowed me to lean in completely and we used our tongues.

I tried to push it a little further by sliding my hand up her shirt, but her hand stopped mine. She told me too much was happening in one night and we should take it slow. She told me I was such a friendly guy and she loved my attitude and personality.