Chapter 1 -- Tony Grows Up
Young Anthony was immediately placed in the hands of an army of tutors while a group of trusties looked after the family fortune. His tutors taught the usual school subjects and in addition taught him about the world of high finance. At 17 he took over the management of the Mad Millions as he called them. He proved to be more than competent and in six months the trusties fired themselves leaving Tony in complete charge of the job. College had never been mentioned for Tony. He had already been trained for his job and clearly did it very well. But he knew that there was much missing in his life. Friends and lovers not the least of what was missing. He was not a virgin; sex had been part of his tutoring and on his 18th birthday his guardian gave him a live-in prostitute.
Tony slept beside the beautiful well paid woman and enjoyed sexual activities that most young men could only dream of. He always felt there was something missing even though he couldn't quite grasp just what it was he seemed to need. He did not believe it was merely that she was being paid to be his lover. He knew that there was something more causing his feelings. Most times he did not consciously think of her as merely a paid slut. She was his companion and sometime confidant. There was also a big advantage to his lover being a whore. It gave him complete freedom to experiment sexually. He quickly discovered his dominant sexual persona. He liked being in total control. He enjoyed indulging in rough physical activities and even occasional humiliation. His paid lover did anything he asked or demanded without complaint or question. Before he was 19 he knew he was and would always be a sexual dominant. It gave him great pleasure but there was something missing. Something he longed to discover and embrace as he had embraced sexual dominance.
However it was more than sex he was missing. He had not attended an organized school since his parents died. He had learned social skills from a tutor and was very good at interacting with people in the business world. But he did not know how to make friends. His only companions were employees and his whore. He was desperately unhappy. He also was becoming bored with his job. Managing the 'Mad Millions' was very easy for him. He was so good at it that by his 20th birthday he had grown the assets to over a billion dollars. At that time only a handful of families had that level of wealth. In addition, to a lonely social life and an increasingly boring job he loathed the crowded city. He reasoned that he hated the city so because it only reminded him that among millions of people he had no friends.
Tony decided that a regular college experience was the way for him to learn things that his tutors could not teach. He knew that managing the family fortune could easily be done part-time while going to school. He also knew that with technology it could be managed from virtually anywhere on the planet. All that remained was for him to find the right college. He looked at all of the major prestigious schools knowing that he could go anywhere he chose. The size of the check that he could write to their endowment fund meant guaranteed acceptance. None of those schools felt right. He did not want to go to a large school and get lost amongst tens of thousands of students. Many of the smaller schools he knew were located in cities where he would still be lost in the crowd. When he was close to choosing a very small school in rural Maryland, he accidentally stumbled upon Ballmon. He liked the Maryland school's location away from the city but was concerned about its extremely small student body and limited curriculum
Ballmon had more than double the students of the other college which allowed for a more diverse curriculum. It was even more remote and removed from city life which really pleased Tony. In addition, something told him an all-male student body was the perfect choice. The only problem was his age. He would be almost twenty-one before the new school year began. Ballmon tended to attract students directly out of high school almost exclusively. More over the in coming class was overwhelmingly from prep schools. Tony was young and rich but he was no kid and did not have daddy and mommy for support. Physically he was a very handsome, imposing, fully mature man. He could easily have been taken for being in his mid-twenties. Mentally, he was a mature business executive who had already succeeded among the sharks of high finance. He wondered if he could find friendships in a group of 18 and 19 year-old guys whose only concern was where they would get their next piece of ass.
He put aside those concerns and wrote a million dollar check to the Ballmon scholarship fund. He wrote another large check to his bedmate so that she would not have to sell her body to another man while he was away. The next few months were filled with a lot of introspection and some doubt. He was giving up a luxurious easy life where anything he could want was at his fingertips for the austere life of a college student in the middle of nowhere. He was giving up the culture of the city for the hominess of the country. He could only assume few luxuries and little culture would be found in Endeavor. He was giving up a sex partner that quickly acceded to any demand for what he assumed would be the sex life of a monk. He was giving up all that was familiar to him in exchange for the unknown. He was giving up a large penthouse apartment to share a tiny room with an eighteen year-old smelly, farting guy.
The idea of a roommate was the one thing that did not really concern him. In truth he had to admit to himself that it excited him in many ways. Some he understood, some he didn't. There was the hope for companionship and male camaraderie that he had never known. He knew that often college roommates became life-long close friends. He wanted that kind of friendship. There was something else that excited him and even invaded his dreams that summer as he waited for the day of his departure for college.
He imagined seeing his future roommate naked. The thought intrigued and somewhat tormented him, especially when it caused sexual arousal. He imagined different looking men, but all were handsome and always there was their cock hanging down from a small bush of hair and fully exposed asses seemingly calling to him. He had of course seen other men naked in his life, mostly at the Downtown Athletic club in the locker room after exercising. Though he was naturally fit, membership in such clubs was a tool of business. He had never given much conscious thought to the naked men he had seen in the past. But these dreams and fantasies made him realize he had taken note of the bodies of these men in his subconscious. He could recall many of them as he thought back. In addition, the idea of being in so intimate a setting as a small bedroom with a naked man somehow seemed different than his locker room experiences. For the rest of the summer he avoided the club's locker room for fear of becoming aroused in the presence of naked men. He hoped that when faced with a naked room mate he would discover that his thoughts were pure fantasy and he would not become aroused.
He did allow himself a small indulgence in the fantasy that summer. A few times while fucking his whore anally he closed his eyes and imagined he was fucking a man. He had fucked her in the ass many times before. He had pretty much fucked her every way a man can fuck a woman. But this was different; he had always known he was fucking a woman. But on these few occasions in his mind instead of his beautiful paid lover he was fucking a young man. He imagined that if he reached between his partner's legs, instead of a pussy he would find a pair of warm balls covered in soft fur and a hard cock twitching with excitement. In his head instead of the excited high pitched female moans that were filling room he heard the deep moans of a man nearing climax from having his prostate stimulated by the hard cock that was stretching his rectum wide open. Though he had cum in her ass many times, that summer was the first time he had dropped to his knees and licked his oozing seed as it leaked from her puckered sphincter. She squealed in delight at the pleasure it gave her not questioning his new behavior. He imagined going lower and finding a pair of balls to suck instead of a creamy cunt. Since the fantasy quickly faded away and his cock grew hard again while he licked and sucked the delicious female cum from her orgasming pussy he again assumed the thoughts were mere fantasy. He thought it was just a healthy erotic dream and not an indication that he wanted sex with a man in real life.
Finally, the morning of his departure arrived. Even though they had had a sexual marathon the previous evening he fucked her one last time. In a way it felt to him like the first time he had really made love to her. He knew she must have felt it also. She stayed in his bed while he showered. Before he could dress she begged him to let her suck his cock one more time. He agreed and she sucked and licked him with vigor until he fed her what little cum his body could muster. He had always been able to quickly recover sexually and deliver some cum even after many orgasms. She remained in his bed while he dressed, watching him and fighting tears. She stood as he prepared to leave. They had one last kiss, her naked and shaking, he fully dressed and anxious to leave. She told him for the first time that she loved him. Even though she was there because he had paid her she did love him and would have stayed with him for free at that point. He did not return her words even though he did feel something that he assumed was akin to love. He knew if he told her that he loved her he would not be able to leave her. He did not want to stay, he was anxious for his new life, and he did not want to take her with him. He left her a rich woman and she would likely soon find a new bedmate. That thought made him sad, but he could not ask her to wait for him. She however, planned to do just that.