Becoming the Man He was Meant to Be Pt. 01

After smoking one of the gifted cigars with the old farmer, Tony took his leave of the Dimplers. When Tony got back to town he was happy to find that Jeremy had arrived. He found him walking down main from the bus station toward the hotel.

"Hey sailor, need a lift?" Tony said playfully as he pulled up next to his friend.

"Shit, fine fucking greeting! I get to town and no one is around. Fuck I called three times from the LA airport to get you to come get me when I got here! Good thing I found the one bus that was running today."

"Shut up and get in! I thought you weren't coming until tomorrow. I was out of town."

"I got an earlier flight to surprise you. Guess the surprise was on me. What do you mean out of town?"

"You got another surprise coming too. You are going to have to bunk with me tonight. Someone else is using your room. And out of town means out of fucking town like in the country."

"Ha in the country. Jeez you are a randy mutha, out fucking Connie Dimpler when you got Serna's hot cunt all the time. Oh and who the hell did you give my room to?"

"Watch you mouth about Serna!"

"Shit, man, you know I am kidding and fuck you can't deny she has a hot cunt."

"Ok I will give you that."

"I hope you are going to give me a lot more. You still haven't told me why I am sleeping with you tonight. Not that I mind."

Tony told Jeremy the whole story about Sherry and Jeff and buying the houses after they got upstairs to his room. Since Serena and Sherry were still out he figured that Sherry was giving the girl the grand tour. Figuring they had a little time Tony asked Jeremy if he had had his cock sucked lately.

"Not for two days Sir," Jeremy replied with a hint of sass.

"Good. I haven't had a tasty cock in my mouth since you left New York. Take your clothes off. After I finish punishing your ass for your sassy mouth earlier I am going to suck you dry!"

Jeremy didn't hesitate to start stripping and both men were naked in seconds. Tony pulled his friend over to the bed and gave him a good hard spanking with his bare hand. He didn't stop until his palm was red and sore and Jeremy's ass was covered in scarlet hand prints. It was all Jeremy could do to keep from cumming in Tony's lap as his cock rubbed Tony's leg while his ass was getting smacked. Tony's own erection was uncomfortably wedged between him and Jeremy. As soon as the spanking was done he told Jeremy to stand up. Tony was just getting into sucking his friends hot little cock when the door flew open.

Serena and Sherry had decided to surprise Tony. They had picked up Tony's favorite whore at the airport and brought her over for some group play. It was the women that got the biggest surprise that afternoon. The three of them, Serena, Sherry and Kelly stood opened mouth staring at the sight of Tony sucking the cock of a clearly well spanked hunk of a guy. Sherry regained her composure first and ushered the other two in to get the door closed. Tony looked up and let his friends cock slip from his mouth.

"Hello ladies," He said cheerfully with a wicked smile on his face. "Looks like we are going to have a party buddy. Does everyone know Jeremy?"

Not waiting for an answer Tony returned to sucking his friends cock. The women took the greeting for an invitation to join in and were soon naked. Sherry and Serena laid out on to bed and began to lick each other's pussies. Kelly got on the floor next to Jeremy and worked her way between the two men. While Tony continued sucking his friends cock, she began to lick Tony's balls and rigid shaft. Soon all five of them were on the large bed with their naked bodies rolling around and intertwining in various ways. Mouths found and claimed various body parts. Pussies, cocks, tits and asses all got attention. At times they didn't know who they were sucking or who was sucking on them. The guys traded off fucking the three willing women. Jeremy was particularly excited to be having sex with Sherry. He had wondered since his first trip to Prospect Lane what it would be like to fuck the elusive older madam. He had tried that night and several more times since to buy her. He wasn't disappointed when he finally got his wish. Sherry was an enthusiastic participant enjoying her new freedom with wild abandon. She would always love Tony for exposing Jeff's true feelings and releasing her from her self imposed bondage. After two orgasms Tony was spent. Jeremy managed to go on for a bit after his third but finally had to beg off and rest. The women continued with the guys just watching for awhile. The five of them went out for a late dinner that night. When bed time came, Jeremy slept as the filling between Sherry and Kelly. Serena slept with Tony.

The next day Sherry and Kelly returned to Prospect Lane. They had to get the house ready for the other girl's return and the reopening. There had been no sign of Jeff and with more women in the house Tony reluctantly agreed to Sherry's desire to sleep at home. She said that she and her girls would be more than a match for Jeff now that he had no hold over them. It was never an issue. Jeff was already in Barbados spending his money and employing his seduction skills on unsuspecting young female tourists. Jeremy went to visit Larry and Janet while Serna and Tony made the long drive out to the airport again. Serena's friend Jillian was arriving that afternoon.

Jeremy still did not know about the surprise orgy Tony had cooked up with Hendersons. There were going to be more participants than originally planned also. Jillian had been added to the guest list after they decided she would be moving to Endeavor. Sherry and Kelly were also added to the guest list. With a planned group that included five women and only three guys, Tony decided he needed to find some more cock for the party. The only other guys in town that Tony had been intimate with were Billy and Jake. He figured the pair of eighteen-year-old country boys would have the time of their lives and decided on including them. He was certain Billy's huge cock would be a welcome addition for the women. Jeremy didn't return to the hotel that night. He had a lot of catching up to do with his friends. Tony, Serena and Jillian had a rather sedate and short three way before the women went off to sleep in Serena's room. Tony was actually happy to be alone in his bed that night.

The next day Tony met with Janet to discus Jeremy's surprise. She was excited about the additional people. However, she thought that so many people coming to their house might raise some suspicions amongst the neighbors. They decided to move the party to Sherry's house. Prospect Lane would still be quiet since the students would not be back for five more days. Tony knew the playroom would be a great place for the festivities. After that he took a drive out to the Dimpler's to see Billy. Mrs. Dimpler greeted Tony and told him that Connie had gone with Sharon to the next town to deliver some quilts they had sold. When Tony said he was looking for Billy, she directed him out to the far meadow. Billy was off alone mending fences. As Tony walked off toward the fields, he saw Mr. Dimpler and the younger boys working behind the tractor barn. Tony was glad to see that Billy would be alone. Billy was so involved in his work that he didn't hear Tony coming up until he was almost close enough to grab him.

"Damn, you could scare a guy half to death that way!" Billy exclaimed when he turned from the fence to find Tony looming over him.

"Hey, hot stuff," Tony said with a grin that would put the Cheshire cat to shame. "Sorry to spook ya."

"Nice surprise really, but what the hell you doing way out here?"

"Looking for you."

"Yeah right. You probably came by to take Connie for a drive and since she wasn't here you came looking to fuck me."

"Hey, no reason to be pissy. I came to see you. I wanted to invite you to a party but hell if you going to be a jerk maybe I will just forget it."

"What party? Come on Tony I am sorry. I will make it up to you."

"Ok apology accepted. The party is a special treat I am doing for a friend from school. We are having a little orgy. I got way more pussy than cock coming, so I thought maybe you and Jake might enjoy joining in."

"An orgy?" Billy said dumbfounded.

"Yeah an orgy. You know a bunch of people get naked and have sex with each other."

"I know what it is. But you know that you and Jake are the only people I ever had sex with. I never even seen a girl naked other than Connie and when we peeked at Jake's sister."

"Well then this will be a good chance for you to see several hot naked women. On top of that you will get to taste and fuck your first pussy."

Tony could see the uncertainty in his younger friend's eyes.

"Don't worry, there will be plenty of cock too. Everyone who is going to be there is bisexual. Lots of stuff will happen. You can suck cock and get one in your ass maybe too if you want that. And man, watching these women go down on each other will put you in orbit," Tony added.

"Wow, you mean anything goes?"

The lump in Billy's jeans and his panting between words gave away his excitement.

"Yeah, pretty much as long as you know to stop if someone says no."

"Ok, cool. Will you come with me to see Jake. I don't think I could ask him alone."

"Sure, but you two have fucked since that night haven't you?"

"Yeah, a few times. But we don't talk about stuff really."

"Alright, but I think we need to take care of something first," Tony added and grabbed Billy's crotch.

"We can't do that out here!" Billy protested.

"Who the fuck is going to see us, a passing crow? Your family is all busy elsewhere," Tony said as he lowered Billy's zipper.

Before Billy knew what was happening Tony had him up against the fence with his pants down at his ankles. Tony was fucking him with only spit for lube. Though the initial pain felt like someone had stuck a hot spike in his ass, Billy soon loosened up and felt only pleasure. Tony reached under Billy's belly and jerked his friend's cock while plowing his ass. Billy's cum dried up on the fence rail and Tony's leaked from the young man's ass into his underwear as the walked over to see Jake. Billy's friend was blown away by the invitation. Despite his reservations about sex with women Jake quickly accepted. He couldn't resist the possibility of tasting some new cock and even though he didn't really want pussy he liked watching. Tony drove back to town with visions of ten naked bodies cavorting in Sherry's play room dancing in his subconscious. He wondered how the combinations would actually play out in such a group. He decided that he would try to make sure everyone at least did something with Jeremy. He was the guest of honor and soon would be back on house arrest. He figured that his sub friend could handle four cocks and five cunts in the same night. As it turned out there would be one more pussy in the mix.

Chapter 12 -- Party Preparations

Tony went from the Dimpler's farm straight to Sherry's house. He had invited all the guests and agreed with Janet to move the party, but he hadn't asked Sherry if they could use her house.

"Hello, Tony," Kelly said with a big smile when she answered the door wearing only a skimpy pair of black panties that barely covered her slit.

Had her pussy not been shaved bare her pubic hair would be sticking out. That thought amused Tony since her hair was as black as the panties. But at that moment it was her small pert tits that really drew Tony's attention. Though she was barely a b cup, her nipples were thick and about a quarter inch long. The surrounding areolas were like small pink circles surrounding a target. Tony knew from experience that her tits were firm and tasty.

"Hey baby, I see it is casual day," Tony said.

"We weren't expecting company," Sherry said as she entered the room.

She was completely naked. The older woman's tits were a stark contrast to Kelly's pert little morsels. Sherry had large breasts which had just begun to droop slightly. However they were still full and luscious. Tony noticed for the first time that while Sherry had much larger tits than Kelly, her nipples were much smaller, almost nonexistent in comparison. Sherry's areolas while large had little additional pigment so they were nearly the same color as the surrounding breast tissue.

"Um did I interrupt something?" Tony asked sheepishly figuring the two women had been playing when he arrived.

"No baby, just a little cleaning. You know everything is better naked," She said giggling.

"Well I have to give you that. Hell nothing like being greeted by two beautiful naked hotties."

"So what brings you by? With all that pussy you got at the hotel now we didn't expect to see you so soon."

"Well I don't think there can ever be too much pussy in my life. But honestly it wasn't sex that brought me by. I was hoping you would be ok with moving tomorrow nights party here."

"Baby, this is more your house than mine now. You are of course welcome anytime. Now is there anything else we can do for you?"

Even though Tony had just shot a load in Billy's ass less than two hours earlier, he couldn't resist the obvious offer. They went to the nearest bedroom and the women took turns riding his face and cock. When Tony left the house he ran into Serena and Jillian leaving the house across the street. Serena hugged him and gave him a big kiss. She could taste pussy on his lips.

"Hey baby, we were just talking to Ms. Jarrod about Jillian taking over the house. The girls are due back day after tomorrow. She is going to stay to say goodbye to them and introduce the new owner. Jillian will move in the next day and get things going."

"Sounds like a plan. Did you gals drive or do you want to ride back to the hotel with me?"

"We walked so we will go with you. But let's go somewhere. There won't be much to do at the hotel until you have some time to recharge baby," Serena answered with a bit of a sarcastic hint in her voice.

"Baby, keep up the sass and I will take you into Sherry's parlor and use the paddle on your hot ass."

Serena laughed sweetly, kissed him and told him how much she loved him. Jillian looked on jealously wishing she had a man like Tony. They picked up Jack and went out for dinner and a bit of pub crawling Endeavor style. The small college town bars were almost empty except for a few locals here and there. The two couples managed to drink enough to make the owners happy they stayed opened. The next day Jack rationalized that it was the amount of drink that caused him to fall off the fidelity wagon. He also decided that the night with Serena was well worth the guilt he would carry. It all started rather innocently when the four of them returned to the hotel.

"Serena, I think you should tuck Jack in," Tony teased as he helped his manager up the back stairs of the hotel. "Would you like that Jack?"

"If she helps me undress first I would love it, boss," Jack answered with a wicked gleam in his eye.

All four of them went into Jack's room and Tony watched as the two girls undressed his employee. Jack had been away from his wife for weeks and had not even masturbated for several days. Having two beautiful women strip him naked caused a not unexpected reaction. Tony enjoyed the sight of his dark haired, blue eyed employee naked and aroused by the women. It was the first time he had seen his long time associate unclothed. Jack's body was fairly furry with a nice covering of black hair from his chest to his feet. His thick seven and half inch cock looked good standing up from a forest of thick pubic hair. Tony could see Jack's large balls despite the thickness of his hair.

"Baby, I think Jack is in need," Tony said with a big grin. "Jack you wanna fuck Serena?"

"From the moment I met her, Tony," Jack managed to slur.

Serena felt surprisingly turned on by the idea of fucking Jack. The pair had been friends for a few years and Jack had shared many private thoughts with her. She knew that he had only been with two women in his life. She had also known that he was very attracted to her.

"Sir, do you really want me to fuck him?" Serena asked Tony in a tone that gave away her desire.

Tony took Serena in his arms and kissed her softly before whispering in her ear, "Yes, it is my gift to you both. Make him feel good baby. You may be the only other women he is ever with."

Serena kissed Tony's cheek and thanked him. She was amazed at his generosity. She could tell it was not like he was giving her away but that he was giving two people a gift. Tony escorted Jillian out of the room as Serena began to undress. It was the first time Tony fucked Jillian alone.

Tony awoke the next morning with the beautiful blonds' long hair draped over his chest and her naked body draped around his torso and legs. It was Jeremy's insistent knocking on the door that disturbed Tony's comfortable slumber. Tony reluctantly went to the door to see who was knocking. Upon discovering it was Jeremy he opened the door and invited him in. Jeremy did a double take when he saw Tony was with a beautiful blond instead of Serena.

"Who is your cute friend," A sleepy voice asked.

Jill didn't bother to try to hide her nakedness any more than Tony had. She just lay on the bed smiling with her near perfect body displayed for the stranger.

"This is my very dear friend Jeremy, who I think Serena probably mentioned to you," Tony answered. "Jeremy, this is Serena's friend Jillian who I know I told you about."

"Damn nice to meet you pretty lady," Jeremy said as his cock hardened in his jeans.

"Nice to meet you too. I have heard some interesting things about you sexy," Jillian said as she casually ran her hand down her still exposed body. "You aren't by chance in the market for a little pussy are you?"

She had enjoyed her night with Tony. It was something she had wanted since the first threesome they had. However, it had been five days since anyone had paid her to fuck. She was itching to be compensated by more than an orgasm. Jeremy was a bit confused. He wanted to join Tony and Jillian, but really didn't understand the question.

"Well if you knew me you would know I am always in the market for pussy," Jeremy said in a rakish way.

Tony who had caught Jillian's meaning quickly interjected, "You can have her for an hour for two hundred bucks."

Jeremy was more confused than ever. Jillian was even more turned on by Tony acting as her pimp.

"Come on, hand over the money and get busy I have to go check on Serena!" Tony demanded.

Not wanting to disobey Tony, Jeremy pulled out his wallet and gave Tony four fifty dollar bills. Tony put two of them on the nightstand and got dressed. Jillian was already moaning around Jeremy's cock when Tony stepped out of the room with the other hundred in his pocket. Tony entered Jack's room without knocking. He smiled at the sight of his beautiful lover lying naked atop his friend and manager. He knew Jack would never cheat on his own. He also had seen the way Jack looked at Serena and she at him. They clearly wanted each other and just as clearly needed a push to fulfill their desires.

"Sorry, to break up this great scene, but we got work to do today," Tony said after a minute of enjoying the view.

Jack sat up and looked around startled. He soundlessly mouthed the word fuck. Serena as was typical awoke with a smile. She looked at Tony and smiled and then looked to Jack and became concerned. Tony too was a bit worried by Jack's reaction. His manager looked like a frightened cornered animal. Yet he made no move to leave the bed or even hide his nakedness. The shock of awaking with Serena nude by his side and the realization of the previous night's activity not to mention the pleasure he remembered left him confused and dazed.