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Cuckold, by Jezebel Rose

CHAPTER I

In my final year of college, 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 mailroom 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 is not as I was barely scraping by, but hey, I was not a CEO either. I had not even remotely considered how I would pay off student loans yet, so yea, I faced the problems any regular college student would. My brother, James, and sister, Madison, 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 hidden, I mean it is unclear where she got her looks and body. 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 ancestral 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.

“Ouch… 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 hush…” 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 crept 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 jazzed 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 was—” 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 “shah…” 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 say to 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 certain respect for her.

CHAPTER II

Around two weeks into the 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 significant. Of course, the senior year group was the lowest, 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 specific insecurity issues. Now, I was an unspectacular American person, roughly 5’10” but I was not very well built. I was not fat; on the contrary, in fact, I was a little skinnier than I would like to have been, with almost no muscle mass. Therefore, I did not get much attention from the girls and inadequate care from the people.

 

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 significant was riddled with the huge, muscular albeit dumb jocks and their female counterparts, 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 escapades dick sizes, where they would usually praise the monster cocks, 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 had even heard some of them pointing and whispering about me under their breath when they thought I could not listen to 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 people would look at them.

The people 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 with steam, and these giggling girls would continuously 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 consecutive 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. They were awkward encounters, to say the least.

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

 

Even if there were friendly people, 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 off cute, 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 Sarah.

 

Sarah was in my lab class and collaborated 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, preferably the serene angelic white, with cute freckles and a fantastic 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, her demeanor was. She was unconditionally kind and did not hang out with the skanky girls. She was very friendly to 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 beautiful, 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 did not seem to notice, and I did not about pick a fight with one of those vast people.

Even the skanks seemed to whisper negatives about her, suggesting how her hot 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 did not think about her erotically, even if it was a scarce though. 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 love her. I also occasionally fantasized about having a huge cock and making her gasp when I took it out. She would just spend hours marveling at it, while she sat on 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, beautiful girl was one I would want to spend the rest of my life with. I tried to steal her away from here and bring her to 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. However, when I would call her to ask her, she would knowingly giggle softly, as if she knew what I was up to. She did not protest it, so I did not 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 could not have their way with her, which was somewhat true, but I definitely did not see her falling for one of those obnoxious people.

 

I also became acquainted with another person in my class, whose name was Ronny. This was a far less amiable acquaintance, and Ronny was seen often as the “Douche of all douches.” He had a big strong build, at 6’3″ and 230 lbs. He was also handsome as well, obviously. He expressed heavy interest in “plowing” Sarah from the beginning, and if it were not 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 people would laugh, and the girls would giggle, in which case Ronny would look at them and give that “douche” 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 Sarah would never laugh, usually just avoid Ronny’s eye contact, because in the end, he was doing this because of her, and I had a feeling she knew that. Ronny 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 merely blush and look away; a reaction I felt came from her knowing she caused it, and from not wanting to give Ronny 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 Sarah would giggle, after which Ronny would be ecstatic and look at her. As usual, she would blush heavily and look away, but even that was enough to hike up Ronny’s ego, which would make him bolder. Sarah 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 shouted a little too, it must have looked foolish. I looked over at Sarah who was holding her mouth while she smiled and I felt happy knowing I made her smile. Ronny immediately looked over at her too, and I assume, she did not look away because she was too busy trying to contain her laughter, but Ronny looked directly at her, and he made eye contact.

Her giggling slowly subsided to just a pleasant smile, and I could only see Ronny’s ego blowing out of proportion in his head. The eye contact lingered, and she finally looked away blushing heavily, still smiling. Ronny 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.

 

Sarah and I continued our routine of meeting up for lunch and studying for the lab, and Ronny continued his silly “dominance” routine. More and more often, I would see Sarah 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 more extended eye contact with the person while blushing and laughing, 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.

Many people would visit the bathroom throughout the length of the class, but I noticed an increase in the frequency of Ronny’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 would not react, so I would turn and look at Sarah, 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 Ronny were funny to her and we would both giggle a little. As I would look around at some of the 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 Sarah 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 bend in entirely, 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 person and she loved my attitude and personality.

 

It was getting late, and I had quite a bit to drink, far more than she did at least. My mouth started running, and I started spilling my insecurities out. I told her about how I can never measure up to the douchebags in our school in both body size and the ohm… “Other” dimension. She just giggled and told me not to worry about it.

I would win her and other girls over with my friendliness and personality, my diligence and patience. When I finally brought up the taboo subject of Ronny and his douche persona, I saw her smile a little. I asked her what was so funny and she replied “huh… oh nothing. I just hush- I think its funny how he gets under your skin. You’re a much better person than him, don’t let him affect you.” I smiled and thanked her.

 

The rest of the night after I had brought up Ronny, she seemed very distracted and aloof. I spilled my insecurities further and told her how much I hated him, and him continually calling me “small boy” and “tiny dick” to which she giggled and repeated “tiny dick…” under her breath. I loved making her laugh. I told her I felt so insecure around him and he emasculated me a lot. She seemed to find all of this quite funny, and I mentally congratulated myself for being so hilarious.

 

She went on to say how she definitely thought Ronny was attractive, but that was it, she knew he was a major douche. Again, I never ever thought anything of her giggling and distraction, just assumed she found my story-telling and talking style very entertaining. I said, “All I ever want is for you to be happy.” She smiled at me.

Sarah and I went on more and more dates until finally one day when we were back home at my place, I managed to get my hand up her shirt while kissing her and things got hot from there. We moved it into the bedroom all the while with me whispering how “I’ve wanted this for so long,” and “I thought this day would never come.” After a handful of more self-depreciating comments, until she finally put her hand on my mouth and said, “shah… stop, I’m here now, so let’s just do it.”

I managed to get her shirt and pants off so that she was only in her underwear. After that, she took off my shirt. I felt a little self-conscious about my lack of muscle, but she told me she thought it was cute. She finally managed to get my pants and briefs off, after which my erection stood free in the air. She paused for a moment to look at it, then looked back at me and bit her lip, trying to stifle a smile. When she saw I was, a little hurt she put her hand on it.

She lied me down on the bed and sucked it into her mouth. It fit inside her mouth without a problem until my pubic hair tickled her lips. She finally got up and straddled me, rubbing her thighs against my cock. I told her I had a condom in my drawer, after which she took off the rest of her clothes and went over to get it. She tore the condom wrapper and tried to slowly put the condom on me.

 

I do not know why but the condom seemed suddenly bigger. It wasn’t as this was the first time I had had sex, and weren’t all condoms the same size, except magnums (Which I would never dream of buying)? My dick could barely fill it up. She looked a little puzzled as to how and why I did not have a dick big enough to fill even a regular condom. She tried to squeeze the sides down along the length of my penis but to no avail. She looked a little disappointed, but she wanted to hide it.

She said, “Oh its ok, we don’t really need to have sex, do we? We can still enjoy ourselves right?” This time I was the one who was disappointed, but of course, I did not show it. ‘Having her here is more than enough,’ I thought. We just cuddled and kissed.

 

I admired her flawless, angelic body all night long. She was hairless from the eyelashes down. It really made me wonder if she was an angel in physical form. I admired her milky white complexion and gorgeous fluffy pink pussy and pink nipples. Over the course of the night, I sucked her nipples constantly and came at least four times as she stroked me with her incredibly soft hands. There was barely any motion as she stroked, as moving her hand up and down just an inch or so already made it slip off my cock. She seemed amused at the idea, and there was something else too… However, I was too inebriated and in too much ecstasy to notice anything strange. In the morning, she was gone when I woke up, and I went about my day as usual.

When heading to class, I noticed her outside talking to a large person, who I could not make out from the back. She was giggling and blushing slightly, and when I came up to them, I saw it was Ronny… fucking Ronny. “Hey, little Dick? How’s it going?” he asked and chuckled. A couple that walked past us chuckled at the comment as well and the person high fived Ronny on the way past.

 

“Fuck you, Ronny!” I retorted. “Ohm… Careful now, little dick here has a temper,” he said, directing his talk to Sarah. “Better be careful baby, he’ll snap in a second. Come to sit with the guys and me, we’ll take care of you…,” he continued, winking at her. She giggled and playfully hit him, “Stoops… be nice!” to which he put his hands up playfully, slowly pivoted around and headed to class. I was angry, so I said nothing about the issue.

Over the next two weeks, Sarah would text me saying she was heading to class a little earlier than average; it was curious, but nothing strange. I would catch him at least three times a week chatting with her outside of class, until the point where she would actually be laughing while blushing and smacking him playfully. When I asked her about it, she replied, “Oh nothing, he’s just a big douche… hum- and he was… just… saying some stupid things, so it was funny. That’s all.”

One day I came around through the exit of the class from the other side, so I was approaching my seat from the top of the hall, down the stairs. There were no pillars past my desk further up, so coming down from the top; my view of the front of the class was unobstructed, all the way until the exit. I walked down unusually slowly and saw Ronny making faces at my desk, with Sarah already there. Obviously, I could not see her face since I was behind her, but I was able to see the motion of her giggling and quickly looking down.

 

As I finally approached the table, she gave a surprised “Oh!” and said, “I was looking for you in the front of the class.” I asked her about the faces Ronny was making and again she said something along the lines of, “Baby don’t worry, he’s just a big idiot, and sometimes he does and says funny stuff, that’s all.” I just accepted it and moved on, and since the midterm session was coming close, I could not have any distractions.

Through our many sessions of studying and many more dates, I progressively fell more and more in love with Sarah. She was so beautiful and funny, and charming too. She kept telling me how smart I was and how much of a right person I was. It continuously convinced me that she was the kind of person who would make the perfect wife.

She obviously did not care about the physical aspect too much, since she did not pressure me into sex at all, and while I did want to keep seeing her milky white body and lovely pussy lips, I did not want to have another embarrassing session like the first one. We went to dinners and movies and yes occasionally fooled around, but I made sure never to mention condoms ever, so we just touched, and I gently played with her body. She never got to orgasm, but I regularly came four or five times. Her hands were just so unbelievably soft. However, it was limited almost exclusively to that, because she would want to finish quickly so we could only watch another movie at home or play a game.

Again, as I always would, I told her “All I want is for you to be happy.”

 

Then one day I was walking to class when I walked past one of Sarah’s friends who smiled pleasantly and waved. “Hi Tiny di—” she stopped mid-sentence and spun around to look at me, and I looked at her.

“OH… hush Hi hum—Justin. How’s it hum… How’s it going?” she managed to stammer out.

“Umm… okay I guess?” I replied, quizzically. “Okay, Bye!” she said quickly and hurried off. It was odd because that girl wasn’t in my class, and definitely wasn’t friends with Ronny and the other douches, so how…?

When I made it to lunch, I told Sarah about the run-in with her friend and what she said. Sarah quickly turned red, looked around and nervously giggled “Well… Oh, I am sure Ronny being the douche he is must be telling some other people and… Well, who knows? Who cares really? Right baby?” she spluttered, with little confidence in her voice. “Yea… I guess so…” I replied, concerned.

We continued working on the Psychology lab, but the entire time Sarah was furiously texting on her phone and seemed a little annoyed at someone on the other end. I managed to read the first line she typed into the iPhone, which was tilted down towards me. It said, “Amy, why the hell did you say…” and then she pulled the phone towards her and continued typing.

Please purchase this story and support me as an author! Thank you! ~ Jezebel Rose

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