Becoming the Man He was Meant to Be Pt. 01

Chapter 13 -- The Orgy

When Serena got back to the hotel she found the threesome in her room dressed and ready. Tony told her to get ready. While the three of them chatted and had a drink, Serena stripped down and headed for the bath. She knew Tony was testing her and the new one. Serena had no idea if Connie could pass all Tony's tests. But she was damn well determined that she would not fail her lover and master. Jeremy couldn't contain his excitement when Serena returned from her shower and dropped her towel on the floor. She strutted around displaying her treasures as she did her hair and makeup and then selected clothing for the night. She knew Tony wanted her to display herself and she did her best to accommodate his desires. Jeremy wondered why they couldn't just stay in the hotel and fuck. The two couples had dinner in the hotel's small dining room. They were the only patrons that evening. The waiter was practically drooling over the two sexily dressed women as he served.

At exactly eight o'clock Tony rang Sherry's door bell. She greeted her guests wearing an expensive silk robe that was short enough to show off her still sexy legs. It was belted and slightly open showing off Sherry's cleavage and the top of her lacey red bra. She asked them to come in a very happy tone. Sherry was living a new life since Tony freed her. She had regained control over her body and life. Sex was again fun. She was excited about the evening that lay ahead. Once they were inside she pulled Jeremy into her arms, gave him a big wet kiss and tight hug.

"So it is a special night for you baby! We are going to give you a monster celebration. Happy birthday hot stuff."

Jeremy was thrilled that it seemed Sherry was to join them. He had only had sex in a group larger than four once. That was at a surfer party a couple of years before. Since it was fifteen guys and five chicks at the party there wasn't enough pussy to go around. He liked the odds having an extra woman provided. She suggested that they go to the parlor and have a drink before heading to the playroom.

"Surprise!" The guests shouted as Sherry flipped on the light in the garishly decorated parlor.

Before anyone could react, Tony grabbed Jeremy, pulled him into a bear hug and kissed him full on the mouth with tongue.

"Happy Birthday, lover," Tony said loud enough for everyone to hear as he grabbed Jeremy's ass cheek and gave it a firm squeeze.

Jeremy was really excited as he looked around the room at all the sexy people and realized he was being giving a real orgy. He saw Billy and Jake who he didn't really know. He had met Billy once and thought the kid might be a fun fuck if he brought along one of his hot sisters. Jake looked like a typical local to Jeremy. But next to Jake was Billy's very untypical sister. Jeremy had hooked up with Connie his first year at Ballmon. He and another student took turns with her mouth and pussy one memorable night in a shed behind one of the local bars. Kelly was sitting on the sofa smiling. Jeremy was very familiar with her talents. He really liked the odds at that point; five pussies and four cocks. Since Billy and Connie were brother and sister he figured that meant only three cocks for her and Kelly took them two at a time. He hadn't yet seen the biggest surprise. When the side door opened and Larry and Janet entered the room, Jeremy broke into a wide grin.

"Fuck, Tony, this is amazing. Thank you, Sir," He said as Sherry and Kelly began passing out drinks.

After a couple of drinks things started heating up in the parlor. Kissing lead to groping and clothes were beginning to be removed. Tony suggested a move to the playroom.

"Tonight's rule, no clothes in the playroom. Leave everything but your underwear here," Sherry said as she slipped off her robe.

She was wearing a pair of red lacy panties to match her nipple-less bra. Tony who was standing next to her gave each of her exposed pink nubs a little tweak before starting to lose his clothes. The women all wore very sexy matching panty and bra sets. Kelly's was complemented by a see thru camisole. Tony had his red devil boxers on. Jeremy wore a blue silk brief that was barely more than a jock strap with a pouch. Larry had gone commando figuring that was the easiest way to go to an orgy. He stood in the middle of the room with his hard cock proudly on display. Jake had a new pair of boxers that looked like they came from a 1950's Sear's catalogue. Billy was embarrassed with the top of his huge erection sticking out of the waistband of his white J.C. Penny briefs. Billy's embarrassment was made worse by the fact that his sister was one of the half naked sexy women causing his erection and looking at him. Tony thought the scene was delicious as he stood by the door watching the nearly naked group head to the playroom.

By the time Tony reached the playroom, Janet was already on her knees in front of Jeremy. She was sucking his balls through the silky blue pouch. The others were forming a circle around them. Tony moved behind Billy and yanked his briefs down. He held the younger man firmly with one arm across his smooth chest while taking Billy's huge fully erect cock in his free hand. Billy was excited to feel Tony's semi erect cock and satiny boxers pressed into his bare flesh. Tony knew only a couple of the people in the room had seen Billy's monster cock. He was also pretty sure few if any of the others had ever seen one that big.

"Let Jeremy have his fun, gang. Who wants a taste of this sweet monster?" Tony called out.

Everyone turned their attention to the cock Tony was happily stroking. Even Janet paused her worship of her young lover's pouch upon catching a glimpse of Billy's long fat hooded snake.

"Damn!" Tyler gasped as he watched Tony roll Billy's foreskin further back.

Jillian, licked her lips and moved over next to Billy to get a better look at the purple headed beast. Kelly winked at Billy from across the playroom. Sherry nearly wet her panties with excitement. She had always liked large cocks. Jeff's almost ten inches had been one of the things that hooked her on him. She had only been with few men bigger than Jeff and never one as big as Billy. Serena who had no doubt that Tony would be certain to arrange a ride for her on Billy's cock in the future went down to her knees and started sucking the nearest available cock. It was Larry that benefited from her sudden urgent desire to have a cock in her mouth. Jake who had had Billy's cock about everyway a guy can take cock wasn't as interested in his friend as he was the other cocks in the room. He got on the floor next to Janet and lowered Jeremy's pouch. The sight of Jeremy's fat little erect cock made Jake drool. When Jeremy didn't pull away the young gay man took it as a signal to go farther.

He pulled the jock strap down Jeremy's legs as he ran his tongue along all six inches of the tasty shaft. Janet lost interest in Billy's big cock when Jillian knelt in front of him and began to take the monster shaft into her talented mouth. As she turned back to Jeremy, Janet saw her husband's cock being devoured by Serena. She took Jeremy's cock head into her mouth as her new partner began to lick Jeremy's balls. Jake and Janet began kissing, sucking and licking all over to Jeremy's delight. When their mouths came near one another Jake confused Janet by shying away from kissing her. He didn't seem to mind when she reached into the fly of his boxers and pulled out his hard cock, however. Jake's cock was about an inch longer than Jeremy's but much thinner. Janet smiled thinking that his cock was thin like his body.

Meanwhile Sherry had moved over to watch Jillian take Billy's long cock deep. She caressed Tony's erection through the satin material of his undershorts as she whispered in his ear.

"Baby, does this sweet young thing know how to use that beautiful cock?" She asked.

"Darling, that cock is fresh as a daisy. He has never so much as touched a pussy with his little finger," Tony answered as he turned to the forty-one year-old madam.

He slid his hand into her red panties and slipped his middle finger into her already dripping cunt.

"Mmmmmm, seems like we have nice experienced pussy here that is ready to go," He said in a sexy tone that nearly melted Sherry.

"Billy boy you are going to get two treats at once. Lie down on the floor." Tony ordered.

Again attention was on Billy. Sherry straddled his hips and lowered herself onto the pole that Jillian was aiming skyward. She moaned seductively as she took every bit of the over foot-long cock inside her body.

"Oh god what a cock!" She cried out when she hit bottom.

Billy was speechless as her cunt enveloped his big shaft in a warm wet cocoon. Tony gave another order and Jillian quickly discarded her panties straddled Billy's face. The young man took a deep breath and inhaled the aroma of a woman for the first time. He was hopelessly hooked on pussy eating from his first taste. Sherry began to slide her wet cunt up and down the huge throbbing shaft as Jillian fed Billy her pussy. Kelly and Connie had crawled over close, wanting a better look at the action and a chance to be with Tony. For a moment Connie wished that Billy wasn't her brother. She knew she would never have the chance to have a cock that big in her. Kelly wondered if she could take Tony and Billy at the same time. Since Billy's big tool was very busy being fucked by Sherry, both women moved to Tony's feet.

They pulled Tony's underwear down as he told Jillian that she was worth every dime he paid for her. That was all she needed to reach the edge. Billy continued to enthusiastically eat her pussy as she flooded his face with creamy female cum. When Jillian fell back needing a moment to recover Billy saw his then naked sister expertly sucking Tony's cock and Kelly licking Tony's ass. At the same moment Sherry drove her cunt down hard on Billy's cock. The combined pleasures and sights caused his cock to erupt. The feeling of Billy's huge cannon flooding her cunt sent Sherry into orgasm. She continued to fuck the thrashing young man and he continued to be transfixed watching his sister suck cock.

Across the room Janet was sucking Jake's cock hard while Jake deep throated Jeremy. He thought that Jake was a good cock sucker and the blow job combined with all the sex going on around him was very exciting. However, he wanted his first orgasm of the night to be in a pussy. It really didn't much matter which pussy since he had already had all the women in the room. However, it had been longest since he had fucked Connie and decided she was his first choice. Jake was just happy that he had a nice cock in his mouth and didn't care who was sucking his dick. He hoped to have some cock in his ass soon. Janet was enjoying sucking a stranger's cock for the first time in her life but really wanted to get her first taste of pussy. She looked around and saw her husband riding Serena doggie style. She was surprised how much she liked seeing Larry fuck Tony's beautiful lover.

She left the two boys and crawled over to kiss her husband and tell him how much she loved him. Then she made her way to where Connie and Jillian were wrapped together giving a little show at Tony's request. Tony was fucking Sherry doggie style while Kelly licked his balls as he watched the women. Billy was rock hard just watching his sister eat the same pussy he had just licked. However, it was more his sister's curvy body then anything that was turning him on. Janet thought about mounting Billy, but that is not what she really wanted. Besides she was a bit afraid that the big cock would hurt her. She was accustomed to Larry and Jeremy who were barely half the size of Billy. Even Tony's cock was at least four inches shorter than Billy. So she went to Kelly and coaxed her to spread her legs.

"Teach me what to do," Janet cooed as she moved between the prostitute's wide open legs.

As Kelly began to talk Janet through her first pussy licking Tony pulled away from Sherry. Larry had cum in Serena and fallen away panting. Tony wanted to double fuck Serena with Jeremy. He grabbed Serena's arm and led her over to where Jeremy and Jake were. They had switched into a sixty nine position and Jake was moaning like he was on the verge of cumming.

"Jeremy, I have another present for you," Tony said causing his friend to look up.

Just as Jeremy took his lips from Jake's cock, Jake came sending his seed flying into Jeremy's face and neck.

Tony and Jeremy both laughed as Jake nearly convulsed from the pleasure. Serena knelt and cleaned her master's friend with her tongue. Tony suggested that Jake go see Larry, hinting that Larry would love to fuck the kid's ass.

"You want to try a double with Serena?" Tony asked Jeremy.

"Is that a rhetorical question Sir?"

They took Serena over to the sling and Jeremy got into position. Tony helped get Serena in on top of Jeremy and then guided his two lovers together. Once Jeremy was deep inside Serena's pussy Tony moved into position and guided his cock head to her pussy. Serena was tighter and without Kelly's experience but still Tony managed to get his cock head into her alongside Jeremy's cock. He slowly pushed until about two-thirds of his length was in her. He began to gently fuck her causing his cock to slide along Jeremy's cock. Serena came first quickly followed by Jeremy. Tony was still holding out and pulled his cock from Serena's sloppy pussy.

The action had pretty much moved to the center of the room. The other eight participants were almost in a heap. Jake was on his hands and knees with Larry fucking him. Kelly who had enjoyed feeding Janet her first taste of pussy was on her back with Connie squatting on her face. Jillian was on her back being banged by Billy. Sherry was watching the action and fondling Billy's tightening balls. Janet was sucking Jake's cock. Tony, Serena and Jeremy joined in. Jeremy stood in front of Connie and fed her his half erect cock while she continued to ride Kelly's face. Serena knelt and began cleaning the pussy juice from Tony's still rock hard cock. Sherry moved over and spread her legs near Jake's face. Jake was so enthralled with the ass fucking he was getting that Sherry had to pull his face to her crotch. He didn't have much skill but every time Larry slammed into him it pushed his nose into Sherry's throbbing clit and soon sent her over the edge.

As he watched the writhing bodies around him, Tony made a decision. His first load of cum would go in Jeremy's ass. It was yet another test. Jeremy had become totally submissive to Tony, but Tony was not yet sure if that was born more of Jeremy's confinement to campus or of a true attachment and desire to submit. Tony left Serena and Jillian to play with each other and moved over behind Jeremy. He slipped his arms around Jeremy as Connie continued to suck him. Tony pressed his cock into the crease of Jeremy's wiggling ass.

"I want to fuck you my pet," Tony said in a low growl only Jeremy could hear.

Jeremy's whole body tingled. He knew that he could not resist anything Tony wanted. He was happily hooked on his master. He had never felt so strongly about anyone.

"Get on your hands and knees and show everyone what hot bitch you are for me," Tony added.

Jeremy hesitated for only a few seconds as Tony continued to grind his throbbing cock into his sub's ass crack. Once Jeremy was in position, Tony told Connie to use her tongue to loosen up Jeremy's asshole. The farm girl enthusiastically dove into the task. She wanted to please Tony completely. If that meant licking another guys ass she would lick it better than anyone had ever licked him before. She used her tongue and fingers to push her spit into the excited young man's rectum.

"That's enough baby. Coat my dick and get out of the way," Tony growled after a few minutes.

Jeremy knew he was going to get a good hard fucking with much less lubrication than he usually had. He was shaking in anticipation as Connie did her best to make Tony's cock slick. He heard Larry cry out as the older man pumped his seed into Jake's ass. Jake's screams of ecstasy were muffled by Sherry's orgasming cunt. Billy had cum again this time inside Jillian's writhing body. The young man's huge cock drove her crazy with pleasure. Billy laid back recovering and watching his first lover prepare to take the birthday boy. As Tony pressed his cock head to Jeremy's still tight hole, the confirmed sub was shaking with the excitement of being watched while his master took him. He pushed his ass back trying to help Tony get pass the resistant sphincter. Most of the party goers were now focused on Jeremy and his soon to be full ass. Tony grabbed Jeremy's hips and thrust hard.

"Put you tit in his mouth Connie! I don't want to hear his cries," Tony barked as his cock spread Jeremy's anal rim wide open.

Jeremy bit into Connie's soft breast and pushed back to fully capture his lover's cock. Tony began fucking Jeremy hard. The excitement of being watched, the joy in serving his master and feel of Tony's cock jabbing into his prostate erased all pain. Jeremy released Connie's tit which would bear his bite mark for weeks and cried out his joy and desire.

"Oh god yes! It feels so good when you fuck me, Sir. I want everyone to know what a hot little bitch I am for you, Tony!"

Tony roared as a ribbon of thick cum shot from his cock deep inside Jeremy's willing ass. Almost everyone in the room wanted to be Jeremy at that moment.

As he backed away Tony snarled, "Fuck your cunt is amazing. Now you may fuck Connie as a reward for being such a good little slut boy!

Jeremy jumped on the very willing little blond. His aching cock quickly found her dripping cunt. He fucked her hard and rough bringing her to a series or orgasms bordering on delirium. While they fucked and others returned to various activities Tony walked across the room.

"Time for a little game of guess who I am fucking," He called out as he flipped off the lights.

Suddenly the room was pitch black. Other than feel there was no way to know who was who. Tony carefully made his way back to the group and crawled into the mass of writhing, steamy flesh. The atmosphere was charged with sexuality and mystery. The room smelled of sex. Everyone was moving about. Mouths and hands found pussies, cocks, asses, tits and every other body part. Cocks found cunts. Sometime they knew who they were sucking or fucking; sometimes not. At one point Connie realized that she was sucking Billy's cock. There was no mistaking his dick. Though she wanted to stop she lingered over his big tool, enjoying it and hoping he didn't know it was her. When she finally did pull her mouth away as someone else began licking Billy's shaft he found Connie's hairless pussy. Neither knew it was the other as he enjoyed his sister's sweet quivering pussy and she enjoyed his enthusiastic but awkward oral skills.

When she reached down to caress his head and guide him she realized who was eating her pussy. She did not stop him. She wanted him. She wanted to feel his huge cock sliding in and out of her pussy. She no longer cared that he was her brother. She tugged his shoulders encouraging him to move up her body. Even when Billy reached her luscious tits he still had no idea he was with his sister.

It wasn't until his cock was almost inside her and she cried out, "Oh god yes, fuck me Billy!" that he knew he was about to fuck his own sister.

At that point he didn't care. Connie was hot and sexy. He kissed her hard and deep as he drove his huge throbbing cock into her waiting pussy. No guy that she had ever fucked came close to preparing her for the feeling of having Billy's tool inside her body. Billy was by far the one family member she really loved. Her parents were her parents and she loved them but that was different. Don was simply an ass who had never been anything but a jerk to her. The younger boys were too young to really know. Sharon was more a competitor over recent years than a sister.