Becoming the Man He was Meant to Be Pt. 01

"Jack, baby relax. Everything is ok," Serena said softly as she reached out to touch him.

"Yeah, man. No worries here. It was just a fun night with friends," Tony added.

"Damn, not sure my wife would see it that way," Jack stammered.

"Well let's not tell her then. Look, you had fun, Serena had fun, everyone had fun and as long as you are cool no one got hurt," Tony added.

"Yeah, you might be right. Maybe we can talk later. I think I better get in the shower," Jack said actually starting to feel better.

He reasoned that Tony was right. He also figured that given his feelings toward Serena and Tony's lifestyle something was bound to happen eventually. That it was while his wife was far away and extremely unlikely to ever know was a good thing. Not knowing what else to do in the rather awkward situation of being in bed naked with his boss's girlfriend while his boss was in the room, Jack leaned over and gave Serena a quick kiss. Then he slipped out of bed and went off to the bathroom.

"Come on baby, we need to go get going too. I have some things I want to talk about. Let's go to your room," Tony said to Serena.

After checking to make sure the hall was empty, Tony walked her naked to her room.

"Why didn't we just go to your room it is closer?" She asked as they got to her door.

"More adventure this way," He teased, "Besides we couldn't get much talking in with Jeremy and Jillian fucking."

Tony stripped down and took Serena to the shower. As she washed him he explained the plan. It was to be Serena's job to keep Jeremy occupied for the day. Before he left he was going to tell Jeremy that there was to be a party for him at Sherry's. Larry and Janet had already told Jeremy that they were going out of town for the next two days. Everyone would be getting to Sherry's and waiting in the parlor for the surprise. Before they finished showering Tony turned Serena around and fucked her as she braced herself against the tile wall. She stayed to wash his seed out of her pussy while he went back to his room wearing a towel. Jillian and Jeremy had just finished and were lying on their backs recovering when he entered the room.

"Jillian, grab your money and get back to your room. Jeremy and I need to talk and Serena will be looking for you," He ordered still playing the pimp.

"Yes sir, thank you, Tony," She said as she got out of bed and gave her pimp a big kiss while clutching the two fifties in her hand.

Tony grabbed his wallet and pulled out three hundreds.

"That's for last night, you were great!"

Having Tony pay her like that in front of Jeremy made her want to get on her knees and suck his cock again. But she knew she had been dismissed. Back in her room she grabbed a dildo and fucked herself to a powerful orgasm.

"Fuck, man. What the hell was that all about?" Jeremy asked still dazed from the wild fuck Jillian had given him.

"She doesn't really get off unless she is being paid. But that is not important. I wanted it to be a surprise but I don't have time for that shit. I have arranged a little party for you. I rented Sherry's play room and you, Serena, Jillian and I are going to go have an all night fuck fest. It is my birthday gift to you."

"Fuck my birthday is in February. But thanks anyway, Sir."

"I know that! But you are going to be confined to campus until at least April if not all semester. This week may be your last chance to have any pussy for awhile. I thought you would like a foursome with me and some very hot women."

"Oh yes of course, I know I will love it. Sorry Sir. So when does this shindig start?"

"That's better, I was afraid I was going to have to take my belt off and wail your ass! The party will be at eight. But this afternoon I want you to go to the city with Serena and Jillian. They want to shop for some shit for Jillian's new house and probably some whore clothes. Anyway, they will need help."

Jeremy agreed and headed for the shower. Tony had never used a belt on Jeremy or anyone else. But both were immediately intrigued by the idea of increasing the level of their play punishments. Tony got Jack and headed to the office. As they walked, Jack felt the need to talk about the previous night.

"Damn Tony, Serena is amazing, but I have never cheated on Stace before. I feel so fucking good and so bad at the same time."

"Jack, I don't know what to say. I am not exactly the poster boy for monogamy. Hell I don't think I believe it is the right thing for anyone. But I also don't tell people how to live. Serena is a great fuck. She likes you and you like her as long as it doesn't take away from your feelings for Stace I can't see it as a problem."

"But Serena is your lover. It doesn't bother you at all?"

"Actually no. Hell, I basically told her to fuck you. She wouldn't do it if I didn't want her to. Anyway, don't freak out and tell Stace. Also, you should know it is ok with me if you want to do it again with Serena."

"Tony, you are a pretty amazing man. But I don't know about doing it again."

There was a lot to do at the office so the two didn't talk anymore about the night or fucking. At about four Tony had a surprise visitor.

Connie had had a big fight with Sharon. The older Dimpler sister was upset and jealous over Tony and Connie. It had become pretty clear that Connie had won the battle for Tony's affection. Of course the odd thing was had Sharon known more about Tony she wouldn't have wanted his affection. To her Tony was a sexy, wealthy, kind man who would be the perfect husband. She had no idea that he was a Dominate, bisexual that would never settle for a single partner. Sharon being the oldest had grown up with a lot of responsibility and was often in charge. While she would play the weaker sex in bed no man would ever dominate her totally. In addition, she found the idea of male gay sex repulsive. Even she couldn't explain why a guy sucking another guy's cock was bad when she was ok licking pussy. Deep down she wanted her man to be a man. Finally, though she shared Tony with Connie and had fucked many guys, once she got married she wanted the kind of marriage her parents had. On the other hand these things just made Tony more attractive to Connie. When the fight got loud and Mrs. Dimpler stepped in Sharon spilled her guts about Connie and Tony having sex. Connie didn't stoop to retaliating by telling her mother that Sharon had also fucked Tony. She wasn't sure her mother would believe her and she didn't really want her to know about Tony's promiscuity.

"Connie, I know you really like that boy. We all think he is a nice boy. But if you let a boy like that have things before he is committed he might see no reason to ever commit to you," Mrs. Dimpler said sincerely worried about her daughter.

"Look not every one wants what you want. Tony and I do love each other. But I already know he is not the kind of man that is going to marry some hick girl and live on some damn farm. I already told him that I am willing to be whatever he wants to be with him," Connie said desperate to make her mother understand.

Her mother slapped her hard and berated her, "I didn't raise you to be a slut. Now stop this foolishness and I won't tell your father a word of it. You know what he would do."

"Mom, it isn't foolishness. Things are different. Ask Miss goody-goody there about her own trips to the hayloft. She is becoming an old maid while spreading her legs trying to hook a man," Connie spat out. "I am sorry momma, but I got to go. I can't stay here where people thinks such bad things that ain't true about me."

Connie packed a bag and begged Billy to take her into town to see Tony. Billy tried to think of an excuse not to take her, knowing that Tony had other plans that night. However, short of telling Connie about the orgy he had no idea what to say. So he threw her suitcase in the pickup and they went to get Jake. Connie rode in the middle of the two boys on the truck's bench seat. Sharon locked herself in her room. Mrs. Dimpler hid her tears and never told her husband what had happened. She knew that he would disown Connie and ban Tony from the house. She knew that Mr. Dimpler liked Tony and she didn't want Connie out of their lives so it was better her husband not know anything. Billy dropped Connie at Tony's office and went on to Sherry's as planned.

Connie buried her face in Tony's shoulder and began to cry as she told him the story of her day.

"Connie, I told you I can't give you what you want. I like you a lot, maybe even love you. But I also love Serena and at least two guys. I can never be the husband your family wants me to be to you."

"I don't care what my family wants," She said as if pleading. "Tony, I want you however I can have you. I love you and I want you, the real you."

"Connie, you don't know what that means. Christ, yesterday, I fucked your brother in the meadow. Last night I fucked a beautiful whore while my girlfriend spent the night with another man at my urging. This morning I sold the whore I slept with to one of my male lovers. The list goes on. Tonight I have an orgy planned as a surprise for that same guy I sold the whore to this morning," Tony said almost desperate to convince her that her feelings were misplaced.

"Damnit! All of that only makes me want you to fuck me right here on your desk, Sir. Please don't reject me because you think I am some country girl wanting a husband. Tony I want you and I will be anything you want to be part of your life."

He pulled her into his arms and kissed her deeply. She had made it clear that she was his to do with as he pleased. There was no doubt that he had feelings for her. But then he had feelings for many people. He didn't really understand how it was that he could be connected to so many. His feelings for Connie caused him to make one last attempt to dissuade her. He held her and looked hard into her eyes as he spoke.

"You can never turn back from this decision. Your family will likely reject you. No young man in this area will ever marry you. You will be in my possession. If in the future you change your mind, you will lose everything you have ever known, Connie. I would never hold you against your will, so you could be free of me, but you would have nothing to go back to, you would have to leave Endeavor forever."

"Tony, I will never change my mind. It will never take any force for you to hold me. I am yours for as long as you want me. Please, Sir, tell me that you will have me."

Tony smiled and kissed her again. She had her answer and he had his pledge. She was his. As the kiss continued he slid his hand under her dress and squeezed her ass through the soft simple cotton panties she wore. He knew her manner of dress would soon change. Serena would be her mentor, helping her to develop a sexier style. Before they got much further the office door opened and Serena stepped in the room. She had concluded her shopping and dropped an exhausted Jeremy off at the hotel to rest up for the party.

"Hey baby, this is Connie," Tony said without releasing the farm girl from his arms. "Connie, this is my lover, Serena who I have told you about."

The women looked each other over after exchanging greetings. Tony had told them pretty much everything about each other. Connie had even seen Serena's pictures. She decided that the exotic big city whore was even more beautiful and alluring in person. Serena only had a description of Connie and her imagination before that moment. She had expected a simple plain country girl. What she saw was an extremely pretty, sexy little package in her lover's arms. She knew that Connie would turn heads in any city in the world given the right makeup and clothes. Tony decided to test Connie's pledge. He knew that Serena would unquestionably do anything he said. He was not completely sure Connie would be able to be so obedient.

"Serena, close and lock the door. It is time you two got acquainted," Tony instructed.

Serena pushed the door shut and turned the lock. Then she turned back to the couple knowing Tony didn't have a drink and some casual conversation in mind. "Ok, good, now both of you take your clothes off!"

Serena immediately moved her hands to the buttons holding closed her expensive jeans. Connie froze, unsure of what Tony was going to expect of her. Serena tried to use her eyes to get Connie to comply with Tony's command as her pants fell to the floor. But Connie was too confused to realize the seriousness of her inaction.

"Damn Connie, you just made a fucking pledge to me. Now the first fucking request I make you disobey me?" Tony said angrily.

Connie realizing her mistake tried to diffuse the anger as Serena continued to undress, "Sir, please, I am sorry. I need to learn what you expect of me. Please give me a chance."

Tony turned toward Serena who was down to just her panties, "Tear these rags off this little bitch!"

Serena was only too happy to comply with that order. She grabbed the front of Connie's simple shift and yanked hard. Fabric ripped and buttons flew off. Connie tried to move away as Serena yanked the torn fabric from the farm girl's shoulders.

"Don't fight this, sweet thing. Your master wants you naked, but I don't want to hurt you," Serena said genuinely trying to help Connie learn.

Connie looked from Serena to Tony who was smiling as he watched Serena forcibly strip his new pet. She saw the futility of her plight. She knew if she didn't give in to everything Tony wanted she would lose him right there. Serena continued by tearing away Connie's old well worn slip. A new feeling came over Connie as Serena pressed her bare tits against the farm girl and reach around to unsnap her bra. She felt the tingle and rush of sexual excitement. She had no control over or idea of what was to happen that afternoon. She was Tony's to command and do with as he wanted. The bra fell away and Serena tore off Connie's cotton panties.

"Bend over the desk, Connie," Tony said softly in a firm manner.

Connie complied as Serena slipped off her own panties. Tony removed his belt and snapped the expensive leather. Connie shuddered and jumped. Her father had used the leather strap on her backside, but never bare assed. She was frightened and excited at the same time. Tony walked over and caressed her supple pale buttock. His touch caused her face to flush and her pussy to dampen. She couldn't stop the slight curl of a smile on lips when she heard the belt buckle clang on the floor. A rush of pure ecstasy set her body on fire when she felt the first slap of his hand on her bare flesh. After three more hard slaps, Tony bent over her and licked the edge of her ear.

"You will never forget your first day as my pet," He whispered in a deep husky tone.

Connie shivered as she remained bent over the desk awaiting her master's next move. She didn't have to wait long. Tony continued the spanking, delivering a total of fifteen firm whacks to her ass. When he stopped her ass was red and stinging. The burn was pure pleasure to the completely devoted sub.

"Serena, kiss your sister's sweet red ass," He ordered

The older woman went to Connie and knelt behind her. She softly kissed and licked the well spanked ass of her master's new pet. It was as if it was a loving welcome to the family. She did not feel jealous. She knew that Connie would be no more than her equal. Tony would love all of his pets.

"Connie come here," Was Tony's next order.

She came to him immediately and he gave her instructions, "Tonight you will join us at the orgy. After we are done here Serena will help you with clothing and begin to teach you about makeup and such. Before that you must show your new sister how happy you are to be joining her."

It was fairly clear that Tony was going to require Connie to pleasure Serena. That did not bother her; she found Serena very alluring and enjoyed sex with other women. What had her concerned was participating in the orgy. If Tony wanted others to fuck her that was ok but Billy would be there. At the very least she would be reveled as a slut to her little brother. At worst Tony would require her to actually fuck Billy. Something she had fantasized about ever since accidently seeing his huge cock. It wasn't something that she ever thought she could do for real though.

"Sir, may I speak, please?" She asked in small voice.

"Yes, my pet, what is it you wish?"

"Um, tonight, it will be my pleasure to do as you wish, but is Billy going to be a part of the orgy?"

"Yes, and he is looking forward to his first taste of pussy."

The look in Tony's eyes concerned Connie. She did not want her brother's first taste to be her pussy. Tony saw the look in her eyes and decided to reassure her.

"You need not be concerned. Other than seeing each other naked there is no requirement you two do anything together. I will not make you fuck him. But I am not really sure why you would object to it as I have seen you rather enthusiastically eat your sister's cunt."

"Sir, I do not know myself why but the two are different somehow. I will honor my pledge and would fuck Billy if you asked it of me, but I do not wish to do so."

"It is enough that you would if I wanted it. I will make no demands at the orgy of anyone other than all enjoy themselves. What does or does not happen between you and Billy will be your business. Now it is time you used your pretty mouth on Serena's pussy."

He placed Serena on her back on his desk. Her ass was barely on the edge, her legs spread, her knees bent and her heels pressed to the smooth oak. This left her dripping pussy wide open. He guided Connie into position and ordered her to eat Serena's cunt and make her scream. He knew that Serena would make Connie work hard by holding back her orgasm. The hot blond used her lips, tongue and fingers to pleasure the exotic beauty. Serena squirmed on the desktop as she fought back the rising tide in her loins. She could feel Tony's eyes boring into her as he watched his new pet eat her pussy. Tony was excited, his cock hard in his pants. But his relief would wait. He wanted to save all of his sexual energy for the party. After thirty minutes Serena could hold out no longer. Connie heard the scream she had been commanded to elicit as Serena's body was overcome with pleasure.

Tony moved behind Connie and slipped two fingers into her pussy and third onto her clit. Within a minute she came hard on his hand. The power of the orgasm caused her to fall on top of Serena. The two women embraced each other as Tony stepped back.

"Serena, find her some overalls to wear and then take her to Sherry's and get her cleaned up and dressed for later. Then meet me at the hotel. We don't want Jeremy knowing about any extra guests."

Tony headed to the hotel to check on Jeremy while the girls carried out his orders. Fortunately there were plenty of sexy clothes available at Sherry's that fit Connie. By the time Serena left the new pet in the capable hands of Sherry and Kelly, Connie was bathed and clothes had been selected. Sherry would handle the first lesson in makeup. In the mean time Tony had awakened Jeremy and dragged him off to a shared shower. Jeremy assumed it was bend over and pick up the soap time, but Tony just wanted to spend some time with him without sex. They both ignored their hard cocks as they washed up and talked.

Once they were clean, dried and dressed the guys went to check on Jillian who was officially Jeremy's date for the evening. When she let them in, only wearing her sexy undergarments, Tony handed her a thousand dollars as payment for the evening and told her to finish getting dressed. She would have preferred that he fuck her on the spot. Jeremy knew from his morning experience with the stunning woman that she was going to be hot and ready after receiving payment.