My kink revolves around a particular incident/fantasy that happened while in college, partially based on fact mixed with some fiction. I have been hooked ever since. Here is how it all started.
My cuckold obsession started with a real life event, when I was in college and dating my first long term girlfriend. One evening after sex, the conversation steered toward her many ex boyfriends. After much prodding, I was devastated to find out that her previous boyfriends were all much larger in the cock department than I was. In fact her most recent ex boyfriend was the largest of them all. Through extended coaxing, I convinced her to tell me more about him. She went into great detail about his enormous size, thickness, and length of his cock. She told me that she actually measured him once. Flaccid he was 7 inches in length, and hard he was over 10 plus inches and thick as beer can. If this were true, he was nearly twice the size of me hard and he being flaccid. I actually met the guy once, and he was a tall, scrawny, pale, thin guy. The kind of guy that you would never guess had a huge hog in his pants. He didn't really stand out and had no real memorable qualities. Obviously, there was one... a very huge one at that!
Of course, this made me extremely jealous, but the strangest part is that it also turned me on. I didn't understand why at the time. I got so hard thinking about his size and masturbated obsessively when picturing him with my girlfriend. He would be defiling her every hole in ways that I never could. I began watch a lot of porn in which guys with huge cocks were with petite girls similar to my girlfriend. She did confide in me that this gifted cock did have one flaw, it was so large, that he had trouble getting and keeping an erection. I imagined that it was the sheer size that made it difficult to get fully erect. She said it would take 20-30 mins of stroking his cock with her hands and mouth to get him fully hard. However, she didn't mind since the payoff was glorious! I asked her once why she broke up with him. She told me that he was a crappy boyfriend and cheated on her all the time. The only reason she stayed with him as long as she did, was because of his huge cock. This naturally made me even more fascinated by the thought of seeing his flaccid cock. It must be flattening to know that a woman would spend that much time and effort just to make a man hard.
This detail of course made it into my daily masturbation fantasy of being their servant and worshiping his cock for her enjoyment. I felt compelled to be on my knees and help prepare his over sized flaccid cock for her eventual pleasure. Getting him erect was too tedious a task for her, that would be my new job. I would take pride in my new role to service his superior cock to full erection, and when his erection would fade, and it most certainly would, I would be there to work him back to his full glory. I would be instrumental in the success of their love making. It gave me purpose.
My obsession went on for a while, with chronic masturbation to the image of his huge cock satisfying my petite girlfriend. I kept this hidden from her for a long time, but I think she suspected because occasionally during sex to spice things up, she would reference his huge cock and it would be an instant turn on for me and I would immediately blow my load. However, even this began to have a lessening effect. Her tales of their sex-capades became more graphic, and her verbal humiliation toward me began to grow. She would taunt me with comparisons. Oddly, even this humiliation seemed to turn me on in ways that I never imagined. I would instantly get hard thinking about his huge flaccid shaft in her hands. Not only was I becoming a cuckold, it excited me to be compared to a much larger and superior cocks. I imagined threesomes where they both are laughing at my size. After a while, I had to take things to the next level. I had to see for myself. I had to know if my girlfriend was exaggerating, and if her ex was really that huge.
Her ex belonged to a gym nearby, and I joined under the guise of wanting to get back to shape. I was once quite the athlete, it was reasonable that I wanted to tone up. I began timing my workouts to finish around the same time as his, hoping to hit the showers the same time as he did. One day, I timed it perfectly. There I was, showering right next him. I found myself staring, almost mesmerized. There he was, his soapy wet massive flaccid cock swinging in all it's glory. It was true, his cock was truly the largest I had ever seen. My jaw must of dropped in amazement, because he turned to me and said "take a picture, it will last longer!" I froze with embarrassment. He laughed with amusement as he noticed my own small appendage sticking straight up as I could not hide my tiny erection from seeing his cock. Memories of being teased in locker rooms of the past flashed before me as I quickly turned off the water and grabbed my towel to cover up and leave. I quickly dressed and left the gym before he had time to see me again.