Jack, Control, and Tom
For several days after he and Rory had zoom sex, after he had fucked Nicholas and been fucked by Tom, not much happened. He spent his days at the bank doing what he always did. He talked to Rory over zoom, getting to know him, learning about his life. They jerked off together, which was fun, but Matt found it ultimately frustrated him. He wanted more of this guy.
On Friday a week later, he got on an app and found a nice, smart woman who seemed to want to hook up. He got to her place in Riverdale and as soon as he walked in her house, he knew. She was beautiful, hot, willing and clearly eager to get going, but when she pulled off her shirt and slid her hand into his pants, he was only half hard. He could see she was beautiful, and a part of him totally wanted to fuck her, but some other part of him wasn't all that interested. He went down on her so at least she would have a good time, but even that – something he normally loved doing – left him feeling empty. Dissatisfied.
When she offered to get him off, he shrugged and put his pants on. He went home, ate a lot of ice cream and went to bed.
He connected with his group every morning, just giving updates, offering advice about moving funds around, timings of purchases, strategies for managing risks. He was happy to talk to them, he realized. Marco was over-stimulated every time, but he was full of good ideas. Liam was the quiet one, but when he spoke it was always with some amazing distillation of what they were trying to do. Nicholas seemed to take a leadership role which Matt was happy to go along with since he felt like he didn't quite know what he was doing yet. But somehow, through every conversation, he couldn't get the memory of their pricks in his mouth or his ass. It was distracting.
Liam called him on Saturday morning asking if he wanted to get some lunch, ostensibly so Matt could ask questions about the investments, but he could tell there was another motive. He was beginning to suspect there was always another motive with these guys.
They went to a diner on Danforth and had club sandwiches and beer. It was a nice day, warm and bright and Liam suggested they go for a walk. Matt kept waiting for him to make some kind of pass at him, or lascivious suggestion, but he didn't. They got to a park and were watching some kids play baseball when Liam turned to him and said, “So Rory? You two are kind of into each other?”
Matt felt a bit stunned by the question. “I guess? I barely know him.”
With a laugh, Liam said, “Yeah, but you do know him in some ways. Really really well.”
Shrugging, Matt said, “Ok, fine. Why do you ask?”
“Just wondering. He's my cousin...so I've known him my whole life. We were born in Wales, but we left when we were kids.”
“Your cousin? Isn't that kind of...incestuous?”
Liam threw his head back and laughed, barely able to breathe for a minute. “Chill, Matt. When I was initiated Rory wasn't part of it. Happy?”'
He realized he did feel relieved. But it felt strange because they had nevertheless been together, naked, and fucked him and each given him a load of cum together. He saw a bench and sat on it, and Liam joined him. They sat in the sun, talking about their high school years. Matt started to really like the guy. He was a bit like Rory, but less extroverted.
They went to a bar and had more beer. After a few sips, Liam said, “Uh, Matt...you should know that once a month for a while, new members...well, have to go to a special meeting on Sundays. And that would be tomorrow. At the office.”
Matt took a big swig of his beer. “Special meeting...does that mean what I think it means?”
Looking guilty, Liam said, “Yeah. Something like that. With Jack. And maybe Tom. But you and the other two new members. I forget their names...anyway...”
“I don't remember either. Well, I guess 'in for a penny' and all that.” He raised his beer to Liam and they clinked glasses.
Matt was soon feeling nice and tipsy and he could tell Liam was right behind him. The bar was quiet with just one other couple having wine. At one point Matt got up to piss and went into the little washroom. As he stood, watching the stream from his cock, Liam came in and went into the stall. He heard his voice behind him. “When you're done there, why don't you come in and join me?”
Matt turned and Liam was sitting on the toilet, his pants down and his cock out which he was stroking to a big fat erection. Now used to how things worked with these guys, Matt nevertheless grinned at him and walked into the stall and awkwardly closed the door. Liam said, “Give me that cock of yours.”
He complied. He unzipped his jeans and pulled out his achingly hard dick which Liam immediately started to suck, still fisting his own. Matt put his hands in Liam' red curls and thrust into his mouth a few times which made Liam moan. It was quick and a little dirty and Matt emptied his balls into Liam' mouth in record time. Liam swallowed happily, and then stood up, pushing Matt down, which he wasn't expecting, but he knew the drill by now. Liam made a strangled sound – hopefully not too loud – and a few big ropes of cum spewed out onto Matt's outstretched tongue. He swallowed, a little shocked, but by this point he was used to cum in his mouth, and he was learning that if the conditions were right – as these were – he was all for it. He stood up and Liam gave him big wet kiss, clearly enjoying the taste of himself.
They went back into the restaurant and pretended like they hadn't just sucked each other off, finished their beer and left.
When Matt got home, there was an email from Jack and as Liam had told him, he was to go to the office tomorrow morning at seven. Jesus. No rest for the wicked. He sat down on the sofa and read more of the handbook and, he realized, with growing excitement. This group really had an amazing strategy that he didn't think anyone else had figured out. Very cool.
When he arrived just before seven, Tom let him in. He had a little smile on his face, and Matt felt better, remembering the feel his body, the way they had kissed with Nicholas' cum in their mouths. He internally shook his head, walking past Tom and into the conference room. What have I become? As much as he was loving it, a part of him still didn't quite believe how much he wanted cock.
He looked around the room which seemed almost empty, but then he saw Frank Chiang, and Roger Freeman standing by the window talking to Jack who looked over at him and said, “Good morning, Matt. Tom, lead these gentlemen into seminar room three.
Tom said, “Will do.” He turned to Matt, “Follow me gentlemen.”
They trailed after him down the hall. Frank was a tall guy with longish dark hair and deep brown eyes, and delicate features. Roger was a built dude with light tan skin and a very healthy beard. Since Matt assumed he knew the kind of thing that was about to happen, he pictures these guys without clothes and realized he felt nervous. But he was glad Tom was there.
They got to the conference room which turned out to be empty except for a wardrobe. Tom turned to them. “Gentlemen, leave your clothes in the wardrobe and stand in the middle of the room.” He grinned at Matt and then left the room.
Right away, Frank said, “Fuck, man. I thought that shit was over with.”
Matt laughed and said, “I have a feeling we'll be doing this from now on. I'm Matt.”
They shook hands and Roger introduced himself. They took their clothes off chatting a little nervously. Roger was indeed built with developed muscles he clearly trimmed his body hair which would have covered his chest and groin with fur if he didn't. Matt couldn't help but notice a very generous-sized dick in all that trimmed bush.
Frank was slim and had very little hair and another impressive tool hanging between his legs.
Just as Roger closed the wardrobe door, Tom and Jack came into the room. Nude of course. And hard. Jack said, “Get on your knees.”
Matt realized he was feeling scared but the kind of scared that was about not knowing what was going to happen. Scared like getting on a roller coaster. He realized his dick was getting a little active.
Just then, a third guy came into the room, also nude. Jack turned to him and said, “Glad you could make it on such short notice, Andre.”
Andre grinned and said, “Glad to help.” He stood beside the other two. Andre was a smaller dude with a tight, toned body, short dirty blonde hair and, Matt realized, amazing almost light brown eyes. His cock was impressively hard and thick. Matt looked at Jack, remembering taking his super-sized prick in his ass, remembering the buckets of cum pouring down his throat.
Jack looked at them a moment and said, “Well gentlemen. Here we are are again. We wanted to remind you of what you did to become a member of this organization. We feel it's important for you to keep it in mind. It is part of the bond that holds us together.” He turned to Frank. “Come here.”
Tom said to Matt, “You start with me.” He was grinning again.
And Roger went over to Andre and knelt down. Jack said, “You know what to do.”
Matt looked up at Tom and had to smile since he was more than happy to get right in there with this guy. Tom ran his hand through his hair as Matt licked his prick from top to bottom, even tasting his trimmed balls that were hanging there waiting. Then he took his whole cock in, remembering what he had learned recently, and let it push into his throat. Tom moaned softly and caressed his face. He could taste some sweet precum oozing into his tongue as Tom pulled out, then slid in again, the head of his cock feeling really smooth. Tom slowly began to fuck his mouth, but lingering as he pushed in as if he as really enjoying the feel of Matt's mouth on the underside of his cock.
Matt tried to look beside him, but could barely see Roger taking Andre's impressive piece of meat. He heard Jack's voice say, “Move to your right, Frank go to Tom.”
Matt reluctantly let Tom slide out of his mouth and moved over to Andre. His cock was all shiny and rigid. He gave Matt a grin and started to push his dick into his mouth which Matt took eagerly. He was really getting into sucking cock and he didn't care what it meant. Andre thrust deep and Matt had to breathe deeply so as not to spit him out, calming a gag or two.
Then he moved over to Jack who said, and not in an entirely unfriendly way, “Take my dick, Matt. You've done this before.”
Matt took a deeper breathe and relaxed his throat and pulled that huge long thing into his mouth, right to the top of his throat. He stopped and relaxed again and Jack pushed even more, pushing the limit of what Matt could take. Then he pulled all the way out and his dick trailed a long rope of spit and precum, then shoved it back in. His mouth felt stretched.
Jack used his face hard for a few minutes, but then pulled out and slapped his dick on his cheek, saying, “Get on your hands and knees. I'm ready to fuck.”
As if hypnotized, Matt turned around. He realized he was now face-to-face with Frank who was in the midst of taking Andre's cock deep, and then Roger got down so they were in a kind of circle, Tom's cock pushing into him. He felt Jack's dick start to invade his ass and he shut his eyes, relaxing his hole and let it happen. He wasn't gentle, but he remembered the feeling from before and knew he could do it. When Jack was fully in, he opened his eyes as Jack started to pound him.
Roger's ass was now being taken by Tom. Roger seemed annoyed, but Frank looked like he was going into space. His eyes were closed and his mouth was partly open. He was close enough that Matt decided to make things interesting. He leaned forward and slipped his tongue in Frank's mouth in a big wet kiss and Frank responded in kind. Roger snorted in disgust and said, “This is fucking lame.”
But Jack, hearing this, said, “Roger. Get the fuck over here.”
He pulled his cock out of Matt, who suddenly felt empty. He could tell his ass was gaping. But Tom moved around and slipped his dick in and started to more gently fuck him, running his hands up and down his back. He watched Jack move over and slap Roger's ass, hard. Then again. “You fucking cock-sucker, I'm going to take you into next week. Open that asshole.”
Roger looked afraid and shut his eyes as Jack jammed his prong deep. Roger moaned and not from pleasure. Jack was merciless and fucked him hard, pushing him forward so that Matt was able to explore his mouth and not from pleasure, but because he knew he would hate it. He drove his tongue into his mouth, feeling Roger's beard scratch his chin.
Andre and Tom switched a couple of times and Matt was starting to enjoy Andre just as much. As Jack relentlessly tore into Roger, Matt turned to Frank and kissed him again, enjoying the way his tongue played with his. Tom said, “I want to see you two fuck. Is that acceptable, Jack.”
“If they want to, let them. It shows solidarity.”
Frank grinned at him and pushed him backward. He was laying on his back with Tom above him. He was looking right up at Tom's big balls. Frank pulled his legs up and pushed his cock in. He realized someone had produced some lube because it went in nice and smoothly. With Frank's face above him, his cock beginning to piston its way into his hole, already stretched by Jack's big piece, Tom knelt down and fed him his dick which was drooling precum. He sucked it in, tasting all that sweet juice and he rode on the waves of being taken from both ends.
All he could hear from the other three were Roger's groans and then Andre was making some noise and he wondered if he had given Roger his cock to suck. But he couldn't think about it much, because of all the cock in his ass and face. Frank was getting into it and his thrusts were getting faster and deeper, and Tom was breathing heavily as well, as Matt sucked, and jerked his own cock, wanting a mouthful. Now that he had a taste for cum, he realized he wanted it all the time.
Frank came first with a loud moan and fired shots into his ass while fucking even harder. Tom pulled out of his mouth and instead of coming on his tongue, pushed Frank out of the way and slid his prick into him, pushing his legs apart so he could lean down and kiss him. Matt was beginning to like this guy a lot. Almost as much as Rory. But he would think about that later.
Tom fucked fast and they mashed their mouths together the whole time until he felt Tom begin to gasp and he pulled back, his eyes shut as he dumped his load deep. Then he leaned forward again and they kissed slowly, lazily. He had a clean, youthful energy that Matt found himself in to. His eyes were bright blue and his curls were...adorable. Matt was surprised at himself for the millionth time and as they kissed he felt a wave of affection for this dude. He put his arms around his torso and they looked at each other, grinning.
But beside them, things were happening. Roger was being punished. He was on his knees and Andre had his hands behind his back and Jack was crouched in front of him holding his face and jamming that huge cock of his deep into his face. Over and over he thrust and Roger was clearly having trouble. Then Jack pulled out. Roger's face was dripping with spit. “You ready to be nice, Roger?”
Roger just nodded. He had clearly learned his lesson because he said, “Fuck me, Jack. I want you to fuck me.”
Jack smiled a little wickedly and said, “Good boy.”
Roger's beard was wet and Matt realized it was cum, which he assumed was Jack's. There were big blobs of it on his neck and chest as well. But somehow Jack was ready to go again and he moved around and took Roger's hips in his hands and stuffed that massive tool into his ass. No preambles or preparation or even lube. Jack growled, “You're going to love this, right?”
Roger just said yes. And then Jack took off, fucking hard. Andre moved around and fed Roger his dick but was clearly taking it easy on him. In fact Matt got the sense that Andre didn't really approve of what Jack was doing, but he was in charge.
After a few minutes, with a roar, Jack emptied himself in Roger's ass. He pulled out and slapped his ass a few times and then left the room without a word. He was pissed.
Andre pulled out of Roger's mouth and said, “You ok?”
“I'm fine. I guess I learned my lesson.”
He stood up a little unsteadily and to his surprise, Andre got on his knees and started to suck his cock, given it some nice attention. Roger seemed surprised, but didn't stop him. Andre was clearly an expert because he sucked a load out of Roger in not time who threw his head back as he filled Andre's mouth. Andre stood up and they kissed. Then Andre, even more surprisingly, cleaned all of Jack's cum off Roger's chest and neck, even sucking it out of his beard. It was all really gentle and Matt could tell Roger was grateful. They had a nice kiss and left the room.
It was just Tom and Frank left, but Frank stood up and said, “Well...it's been interesting as usual, but I've got to go. See you tomorrow night.”
He left and Matt stood up, assuming he had to leave. But Tom said, “Why don't you stay...we can hang out...if you want.”
Tom stood up and Matt admired his eyes, and his curls. “Sure...why not?”
Beaming, Tom led him out of the room – still naked – and down the hall to a door that he unlocked from a keypad on the wall. When the door opened, they went into what Matt realized was an apartment. “You live here?”
“Yeah. This is my place. Jack may be tough and sometimes brutal, but he's been amazing to me. I was in a tough place a few years ago, and he hired me and I got cleaned up...I was doing some heavy drugs...anyway, he said I could live here and I've been here ever since.”
Matt was surprised. “I wasn't expecting that from Jack. I'm impressed.”
“You should be...behind that angry exterior, he's a pussycat. Anyway, you want to have a shower?”
With a laugh, Matt said, “Fuck, yeah!”
They stood in a big shower stall and kissed and washed each other. When they got out and were drying each other off, Matt decided something. “You know, Tom...Rory and I...I think we're starting something. But I really like you. It's a bit confusing.”
Tom's face broke out in a big smile. He leaned forward and kissed him softly. “I know you and Rory are into each other. That's cool. We can be into each other too. Maybe all three of us will be into each other. Let's just see what happens.”
If someone had said to Matt a month previous that he would find himself contemplating a relationship with a guy, much less two guys, he would have said they were nuts. He couldn't believe how quickly his life had changed. It was like that initiation with seven cocks and fourteen loads of cum had reset his sexuality. Radically.
They ate dinner that Tom prepared while Matt watched, pouring glasses of wine for them, then made their way to Tom's bedroom. Earlier, Tom had retrieved his clothes, but he had only put his underwear on and these Tom proceeded to pull off with a sly smile. They kissed and Tom sucked his nipples for ages, which Matt had never experienced before. It hadn't occurred to him or the girls he dated that this was a thing. But it was a thing and he loved it. When Tom bit them gently he thought he would come right away, so he pushed Tom on the bed and feasted on his cock for a while, slurping and pumping and squeezing out globs of precum and growled and swallowed as much as he could. Then Tom pointed to some lube beside the bed and Matt didn't need any instructions. He slicked himself up and pushed his way into this lovely, gentle man who had was surprised to find himself really liking.
He fucked him for what seemed like hours until finally, gasping, almost overwhelmed, spewed a gallon of cum into him, kissing him the whole time. Tom flipped him over and did the same, taking even longer and finally coming in his mouth – because he knew he liked it – then cleaning his face off of some ropes of jizz that didn't quite make it.
They were asleep really fast and the last thing Matt remembered was how much he wanted to tell Rory about this, about how amazing this young man was. Maybe Tom was right to say that surprising things were possible.
Matt woke up early, his phone alarm going, and pulled himself out of Tom's arms, dressed and with a quick kiss, left him in bed. He made his way home just in time to connect with his group for their morning meeting. When he signed into the group, they were already talking excitedly. “Hey, Matt...have you looked at our stocks?” Nicholas seemed stoked.
“No...I haven't had a chance.”
Marco burst out, grinning like a fool. “Twenty percent, man! It's working.”
They all gave a little cheer and talked about next steps. Matt was amazed. Twenty percent. That was unheard of. He grinned like a fool, and not just because Liam was grinning at him. He remembering taking his cum and almost without thinking, knew he wanted more.
When they signed off, he showered and got ready for work, excited by their financial success. He started having fantasies of buying a house.
During his lunch break, he buzzed Rory who answered with a big smile. “Hey, Rory. I'm so glad to see you.”
“Me too.”
“I wanted to tell you I spent the night with Tom. He's a very cool dude.” He told him and he was almost afraid of the answer, as if Rory would be jealous, but really, he wasn't sure what the response would be.
“Tom? That's awesome! He's the sweetest guy. He and I have fucked many times, so I approve.”
“You have? I got the sense from Tom that you weren't that close.”
“I think he's just being shy. The little brat. I'm glad you got to hang with him. I really like him.”
When Matt rang off and went back to work he felt good. Really good. Excited. Things in his life were taking interesting turns.
