Becoming the Man He was Meant to Be Pt. 01

He casually reached over and opened his friend's trousers releasing his hard compact cock. Just as causally he began to fondle Jeremy. Serena took the initiative to remove their guest's pants as Tony stroked and caressed Jeremy's bouncing cock. She could feel the heat building in her body and the dampness beginning to ooze from her pussy as she watched her lover and master fondle another man's cock for the first time. She had been wrong about her reaction. She could see in Tony's eyes that he was truly happy and in his element.

"My I undress for you Sir," She asked softly still kneeling before the pair."

"Mmmmmmm, yes please do. I am sure Jeremy will be very pleased to see your body."

Jeremy thought he might cum on the spot when she stood and reached behind her back to lower the dress's zipper.

"Perhaps you could use some help with that," Tony suggested as he slowly stroked Jeremy's cock.

Serena turned and stooped down to allow Tony to lower her zipper. When she stood and turned the dress fell. She lifted her feet and left the expensive fabric in a puddle on the floor. She was braless so there were only her translucent panties shielding her nakedness. Jeremy's breathing became more ragged as his eyes drank in the beauty that stood all but naked before him. There was not a flaw on the flesh of the nearly perfectly formed woman. Serena's pert tits were like the watch of a hypnotist to Jeremy. His focus fixed upon the gentle rise and fall of the olive orbs with dark enticing circles. He was nearly salivating over the prospect of taking her tits into his mouth and sucking and biting her delicious flesh. His desire was not lost on Serena or Tony.

"Sir, perhaps your friend would like to unveil the last of me," Serena suggested.

"An excellent idea and then you can finish undressing him," Tony replied as he stood.

Serena stepped forward until her long silky leg pressed against Jeremy's bare knee. Tony began to remove and toss aside his tuxedo as he watched Jeremy slowly slide Serena's panties down her long legs. When he was done she playfully pulled his head forward and nuzzled his face against her tiny bush. Tony's jacket and shirt were gone and he was lowering his zipper when Serena pulled Jeremy to his feet. As Tony shed his pants and boxers, Serena removed Jeremy's coat and shirt. Once they were all naked, Tony moved behind Serena. He reached forward and pulled Jeremy tight to the woman. Serena became the filing in an erotic sandwich. She loved the feel of the male bodies and their hard cocks pressed against her. Tony kissed her shoulders and neck while she kissed Jeremy's mouth.

Tongues began to dance around as mouths and hands roamed around. Tony slid around enough so their faces met and suddenly Serena found herself sharing a three way kiss with the two men. Tongues moved from mouth to mouth to mouth blurring the lines of who was kissing who. After several more minutes of kissing, fondling and rubbing their hot flesh against each other Tony said that it was time for bed.

"Yes, Sir," Serena and Jeremy said in unison.

There was a curved floating stairway leading from the sitting room to a balcony which provided access to the master bedroom suite. Tony lead the way to the bedroom that itself was larger than any hotel room Jeremy had ever seen. In the center of the main room was a massive oak bed with a thick plush mattress. Tony didn't bother to pull down the embroidered silk bedspread before diving into the middle of the bed. He lay upon his back patting his hands on each side clearly inviting his playmates to join him. Jeremy slid in on Tony's right and Serena on his left.

He kissed them each and then softly moaned, "Suck me."

Jeremy felt a rush of pure elation upon being ordered to pleasure Tony in front a woman. He had resisted when Tony did it in front of Brian. There was no need for a spanking on that New Year's morning.

Jeremy kissed and licked his way down one side while Serena did the same on the other. Their lips and tongues met at Tony's cock. Tony caressed his lovers as they combined to lick every inch of his cock and balls. He moaned appreciatively as they began trading off. When Serna was sucking Tony's cock, Jeremy sucked his balls and vice versa. When their mouths came together they shared brief kisses. Soon Tony wanted more. He had Serena mount his cock. As she slowly road him slipping her wet silky cunt up and down his poll, Tony position Jeremy on his hands and knees with his ass facing Serena and his chubby throbbing cock hanging over Tony's face.

"Lick his sweet little hole, Serena," Tony commanded. "Make his boy cunt ready while you get my cock nice and slick!"

Tony grabbed Jeremy's cock and pulled him down causing his ass to rise up and be presented to Serena. She continued to impale herself on Tony's rigid pole as she began enthusiastically following her master's instructions. She was truly excited to see Tony fuck the sexy ass being presented to her. Tony started kissing and licking Jeremy's twitching cock. Jeremy had to fight to hold back his orgasm. The combination of the anticipation of having his ass drilled by Tony, the ass tonguing Serena was giving him and Tony's fondling and sucking was driving him to the edge. Serena's cries of passion were muffled by Jeremy's ass as she tongue fucked him while cumming on Tony's cock. There was nothing to muffle the moaning caused by the orgasming beauty pushing her tongue into Jeremy's tight hole.

"Oh god, yes!" Jeremy cried out. "Please, Sir, I need your cock so much."

Serena bit into the softening rim of Jeremy's anal orifice as his words sent her body into another orgasm. Her weight was pressed into Tony and she was grinding her pussy hard down on his rigid member. In that position her cervix pressed against the head of Tony's invading serpent.

"Enough," Tony growled as he pushed Jeremy away.

Serena quickly climbed off her lover and watched as he grabbed Jeremy and pulled the anxious young man to his knees.

"Get some lotion for his cunt!" Tony called to Serena as he pushed Jeremy's face down to the soft bedcovers and slid a single finger into his ass.

Serena ran to the bath and quickly returned with a bottle of expensive bath oil. She poured some on Jeremy's crack as instructed.

"Oil up my cock!" Tony ordered as he worked the oil into Jeremy's ass with his fingers.

Once his cock was oiled and Jeremy's ass was greased and stretched Tony moved into position and ordered Serena to feed Jeremy her cunt. As Tony slowly slid his cock into Jeremy's slippery asshole, Serena propped herself up against oak headboard and spread her legs so that Jeremy's face was between her thighs. Jeremy dove into the task of eating the exotic dark haired beauty's pussy as Tony rhythmically plowed his ass. Serena was gasping for breath and cumming again within seconds. Tony's cock's insistent jabbing of Jeremy's prostate had the young man nearly delirious with pleasure. Had his face not been smoothed with Serena's pussy his cries would have shaken the wall hangings. Tony felt like he had discovered perfection itself. Two of his loves, his sweet pets were under him and the three of them were sharing a great passion and all were filled with pleasure. Almost as if a switch was thrown Tony and Jeremy came as one. Their cocks erupted; Tony's sending his hot semen into Jeremy's bowels, Jeremy's creating a pool of thick musky goo on the expensive bed covers.

After a few more thrusts Tony fell away and lay on his back panting and smiling. Jeremy rolled the other way onto his back and also lay panting and smiling. Serena stretched out and her legs framed too spots on the silk bedspread. Near her pussy was a large wet circle formed by the flow from her sex. Below that was a smaller puddle slowly being absorbed by the exquisite imported fabric. Tony recovered first and pulled Serena to him. He held her close enjoying the warmth of her quivering flesh against his body as he kissed her softly. Jeremy scooted closer and pressed his body against Serena's backside. The trio soon drifted off to sleep entwined in each other's arms. As if they were of but one mind they each dreamed of a shared life of sexually charged bliss with the other two.

Chapter 11- Tony Returns to Endeavor

Two days after the party, Serena and Tony left New York. Even though school would not start until January 15th, Tony was ready to get back home. It was going to be several days before Jeremy joined them but with all that remained to be done Tony would be well occupied. Besides between them they had nearly fucked Serena's pussy raw on New Year's Day. Tony chuckled to himself when he thought about his friend squirming on his sore ass while flying home. Jeremy had practically begged for the spanking he got with his sassy mouth and Serena spared no enthusiasm when she used her biggest dildo on him.

They were met by Tony's new Endeavor office manager when they arrived at the airport. Jack Mason was forty-five and had worked for Madison family since a year before Tony was born. He was thrilled at the opportunity Tony offered him to take his family away from the city. Jack had grown up in a small town and felt that it was a better life. He had arrived in Endeavor the day after Christmas. Tony was surprised at the progress report he received as the three of them rode to Endeavor in the new limo Jack had bought for Tony. The driver was a local man. Tony had specifically asked that as many jobs as possible go to the citizens of Endeavor and its environs. In addition to the limo, smaller less ostentatious vehicles had also been purchase for Serena and Tony's personal use. Temporary offices were already being set up and the process of staffing had begun.

The only hitch at that point was that the apartment renovations were behind schedule. Tony had planned to move Serena into her own apartment by the time classes began. Jack had already made arrangements at the hotel to have rooms available for Tony, Serena and several others including himself. Jack had purchased a house just off of College Boulevard that was in need of some renovation. The huge once elegant home was built by one of Endeavor's leading citizens before the college existed. When the man died, his heirs moved the business to a bigger more prosperous town. The home served as a summer retreat until Endeavor no longer stimulated the interest of the family. It had been closed up for more than twenty-five years. Jack was thrilled when he learned it was available. Since the rental his family would be living in until the house was restored would not be available until February first, he was living the bachelor life at the hotel.

Tony decided that the limo would be kept garaged and only used for longer trips. It was not appropriate for anyone to be chauffeured around the small town. Truth was cars were barely needed in Endeavor. They were only needed to leave town. The only place Tony could imagine driving to would be the Dimpler farm. Since he had already made plans to give Connie a job and an apartment in town that would be an infrequent journey.

Connie was the one new person in Tony's life that Serena was not anxious to meet. His feelings toward the young woman were obvious when he spoke of her. Serena had no doubt that Tony was in love with Connie. Even though Serena also had no doubts about his feelings for herself she feared that a growing attraction to another woman might diminish his attraction to her. When she thought about such things she recognized the paradox of her feelings. After only one night with Jeremy and Tony she no longer worried about Tony's feelings for the men in his life. Which was odd because Tony's love for Jeremy was even clearer than his love for Connie. Then there was Sherry the madam that had broken her own rules and fucked Tony. Serena was not yet sure of that relationship. Tony clearly felt Sherry was special and had deep feelings for her. But they seemed less like the feelings one has for a lover and more like the feelings one has toward a mentor or a parent. To Serena it seemed that for Tony all emotional pairings would lead to sexual connections.

By the time they were within ten miles of Endeavor Tony was nearly giddy with excitement. He was home and he was extraordinarily happy. Serena liked seeing him so happy. She also liked the little town she saw outside the darkened windows of the limo.

"Wow, Tony you didn't tell me how beautiful our new home would be." She cooed as the limo turned onto Main Street.

"I am glad you like it, baby. I do not intend to ever live anywhere else and I want you with me always," Tony said sincerely as he took her hand in his.

Jack smiled at his boss. He thought Tony was lucky to have a woman like Serena. Though Jack was devoted to his wife and family and never entertained a thought of cheating, if Serena was available to him he knew he would stray at least once. Her physical beauty and allure was undeniable by anyone. But there was more to Jack's attraction to the green-eyed former prostitute. He had come to know her over the years that she had shared Tony's bed and life. He thought she was smart, witty, interesting and caring. Her devotion to Tony was obvious as was her kind and gentle way with everyone she knew.

The limo pulled up to the hotel and Jack led the couple up to their separate rooms. He explained that he felt it would be more appropriate to keep up appearances of a chaste relationship in the small town. Tony agreed. He knew that there were reputations to consider as well as other factors. While he had no intention of lying to anyone he had a personal relationship with, people like the Dimplers did not need to know that he was sleeping with his personal assistant. It would make them very concerned when he brought their daughter to town.

Tony and Serena were given the two finest rooms in the small hotel. Each occupied a front corner of the top floor of the elegant old building. There were three other rooms on that floor. Jack's was in the back. The room reserved for Jeremy's was adjacent to Tony's and the remaining room had been serving as Jack's temporary office. He assumed it would remain unoccupied when he moved to the new offices later that week.

"Jack, thank you for setting everything up so well. I do not think we will need anything else today. I would like you to make some time tomorrow to meet with Serena and help her get set up for her new job. She takes care of me very well already, but I want to make sure she is cognoscente of all the little details that will be trusted to her now."

"Yes, Sir and thank you, Tony. This town is great and I know my family will be very happy here. I am going to head down the street and check on the construction work."

Endeavor had seen more activity in the two weeks then it usually did in two years. Every construction worker in the area had been put to work renovating property for Tony. Most had no idea who they were working for, but were grateful for the income. Three small buildings just outside the business district were being turned into apartments. The long closed W.T. Grants store on the corner of Main Street and Eastern Way was being converted into the headquarters of the Madison family enterprises. Behind the building that stood just two blocks from the Prospect Lane whore houses the foundation for a new four story office building was being laid. It would be the tallest building in town when it was completed eclipsing the old town hall building by five feet. Almost no one in town knew what the Madison Trusts were. They didn't really care much either. All they knew was investment in Endeavor was a rare thing. They hoped that it would be the good thing it seemed to be. Other less obvious investments were also being made; most of them using corporations that disguised the name of the real buyer. Tony did not want everyone in town to know the extent of his wealth and holdings in the town. There was one transaction that had yet to be begun. Serena was excited about the prospect of owning a house where other women sold their bodies and she just collected a fee for making the arrangements. Tony had had a virtually untraceable entity created as an offshore concern. If he was to buy a whorehouse he did not want anyone to ever know his family was the owner. The Cayman Islands discrete banking system would shield the identity of the owner of the funds used to make such a purchase from even the IRS. Since Serena's friend Jillian's name would appear on the deed to the house, no one would ever know the real owner.

Serena had cooked up the idea of her friend being the visible partner in the enterprise. Jillian had become bored with fucking rich old men. She could have simply retired but that would have meant giving up the only thing that truly excited her sexually; being paid for sex. Jillian enjoyed being a prostitute. It was her perversion as much as her profession. When Serena told her about the small town full of horny young men willing to lay down big bucks to fuck small town whores it seemed the perfect solution. Though she didn't really need the money so much as the willing patrons Jillian figured they would pay much more for her talents. Tony agreed to the plan provided that one of the existing houses could be purchased. He was reasonably sure that the town would not like a carpetbagger coming in and opening a seventh house of ill repute.

Prospect Lane was the first place Tony took Serena that afternoon when they went on a walking tour. Since it was daylight and the students were all away there was no activity at all on the street. Tony knew that most of the working girls were on vacation as there was little local trade to service. He had called Sherry before they left New York to make sure she would be around. As it turned out her and her husband were both in the house when Tony showed up with Serena. Tony was a bit concerned to see the strange man in the parlor when Sherry showed them in.

"Tony, I don't think you have met my husband, Jeff. Jeff this is Tony Madison and his friend Serena."

Jeff stood and offered his hand, "Sherry has told me a lot about you, Tony. Nice to meet you. Must say seems pretty ambitious of a student to want to own his own whore stable."

Sherry winced inside at her husband's characterization of their business. But she couldn't say anything. Though she was the face of the house, Jeff owned it and in a since her. She loved him and was glad he was a gentle man physically. His only kink was humiliation and fucking the women that worked for him. He never let Sherry forget that she was a whore. Part of his cut was getting to use the other girls whenever and however he wanted even though he insisted that Sherry be true. Except on those occasions when he would sell her for a big price. Sherry knew one of the reasons that she couldn't resist Tony was that he never treated her like a whore.

Serena who had always been unusually perceptive was uneasy. She could feel the tension in the room. She knew that Tony had fucked Sherry but thought it unlikely that Jeff had that information. But Jeff definitely had some feeling about Tony as did Sherry. Serena figured that Jeff had picked up on a vibe even though he didn't know its meaning. Tony shrugged off the question indicating that he wasn't an average student. Even though Jeff realized he was dealing with a man of some substance he pressed his point.

"Well than, you might be in luck. This exquisite creature isn't by chance going to be the lead treasure in your stable is she?" Jeff asked leering at Serena like a stray dog looks into the butcher shop window.

"I think we need to straighten some things out, Jeff. First I do not plan to own a stable. I am acting on behalf of someone that is interested in running a house in a nice quite town. Second, I would be grateful if you employed manners that were appropriate to gentlemen outside of a whorehouse when speaking to women in my company. Finally, since my business is with your wife, perhaps you would be kind enough to sit down and shut the fuck up!"