The First Meeting, And After
Matt got home in the afternoon after the almost twenty-four hours of...what? Initiation, yes, but there was more. Way more. He had, in that short time, probably the best sex of his life with Rory. A guy. And before that it had never dawned on him as a possibility that he would ever have done it. He would have punched someone who suggested it. But now?
Quite apart from the fact that he had sucked off six other guys, swallowed their loads and then got fucked by them. Including Dave. And not just fucked in the ass, but had cum dumped into him seven times. And then...fuck...he had fucked Rory. That was blowing his mind. And he had loved it. And kissed Rory. A lot.
He sat on the sofa and pulled out the card that Rory had given him when he left the house. They had been standing in the big front hall of the house and Matt had realized he was surprised to see Rory all dressed up in a really well tailored suit that fit him perfectly in all the right places. His pale hair and intense eyes were a shocking contrast to the dark grey of the suit. Matt had been unable to say much because he was feeling too many things at the same time. He had wanted to kiss him, but he also wanted to run. He wanted to get back in bed with him and he wanted to say, But I'm not fucking gay! He didn't know what to do.
Rory had seemed to get it. He handed Matt his card and said, “I'd love to hang with you again, Matt. We did something pretty awesome down there. That other shit was just theatrics. We did something different. Better.” Then he had leaned over and kissed him very chastely on the cheek. That had been almost the most shocking thing of all. Just that little touch from his lips. Matt had just looked at him, but he had found himself smiling despite himself. All he could say was, “Cool.” Rory had given him a grin and left the house. He remembered standing there feeling stunned.
In his own place, he got in the shower – even though he'd already had one at the big house – and stood under very hot water for a while. His body ached. His asshole ached. His jaw was sore. But despite all that, he couldn't get the image of Rory's face out of his head, the way they had kissed for ages while he fucked him. The taste of his cum.
For the thousandth time since leaving the house, he said to himself, what the actual fucking fuck? He went to the gym and lifted a bunch of weights, used various machines and ran a bunch on the indoor track. In the shower he suddenly felt strange, almost vulnerable. He wondered if anyone could notice that he had been gang-fucked the day before. And, more surprisingly, he surreptitiously checked out other guys in the shower, something he'd never done before. So many different bodies, so many different sizes, shapes. Long cocks, big balls, hairy, trimmed, ripped, a little paunchy. It wasn't that he was excited so much, but he was fascinated.
A couple of the guy in the showers looked back and that was a trip. He quickly looked away, afraid of what might happen if he didn't.
Back in the locker room, one of the dudes from the shower had a locker across from him and he was clearly putting on a show. He stood, stark naked, and towelled his hair, then turned and bent over, displaying his ass. Matt tried not to look, but managed to sneak a glance or two before slamming his locker closed and almost running from the gym.
He checked his email when he got home and there was one from the Investment Society. A meeting Monday night. This was really happening. There was also one from Rory asking him how he was. That felt nice, but at the same time he felt strange that it felt nice. What did that mean?
Matt went to bed early and slept long, way longer than usual. He got up at noon and still didn't feel like doing much. His body ached. His ass felt bruised and his hole was tender.
After eating breakfast, there was another email from the Investment Society. A big pdf which seemed to be a manual about how the society worked and the basic principles of their approach to investment. Matt spent the whole afternoon reading it, making notes, and getting excited. Matt wasn't rich, but he had a good job and a bit of cash that he hoped would become a lot of cash with this new way of looking at things. When he finally went to bed, he was stoked. This could be the making of him.
He went to work at the bank. He was a branch manager and kind of liked it, but was really hoping to move into the corporate offices. At the end of the work day, he left his office, and made his way to the address from the email which turned out to be in one of the tall buildings downtown. Toronto has a few of them now. Really tall. The forty-second floor. Matt had never liked heights much so he decided he wasn't going to look out the windows.
The office was a heavy wooden door the just had a number on it. “Five”. Weird. When he knocked it was immediately opened by a youngish guy in a nice suit. “Welcome Mr. Oberland. Just through those doors.
As he walked to a set of big double doors, he wondered how the hell this dude knew his name. But that was forgotten when he walked into a huge conference room with an equally huge table. There were some guys sitting, some standing in little groups, talking. All guys, he realized. He guessed they wouldn't win any anti-misogyny awards. He noticed that all of the guys from Saturday were there. Plus a bunch of others. A couple of them nodded to him and he felt better.
“Take your seats, gentlemen.” It was the tall dude, the really tall one with big prick. He was in this amazing fuck-off suit and his deep brown eyes seemed to bore into his. Impressive man, Matt thought. Matt wondered where to sit and the curly-haired guy from the weekend waved him over with a big smile.
“Hey, nice to see you.”
Matt grinned, feeling weird having had this guy's cock and cum before even knowing his name. As if he read his mind, the guy said, “Nicholas. Glad you're here, Matt.” He looked genuinely pleased and not in a I'm-going-to-fuck-you way, but just in a nice way.
The tall guy introduced himself – Matt remembered some guys called him Jack – as Jack Morgan. He introduced Matt and a couple of others who Matt assumed were also new– Frank Chiang, Roger Freeman – and then the meeting started. He noticed an agenda in front of him, so Matt followed along, but not having a clue what was happening. He took notes where he could.
Jack started by saying that two members – Harry MacKendall and Rory Mullen had been moved to Vancouver for a while. Matt realized he was disappointed. He had begun to feel that Rory was the only guy he fully trusted. And not just because he had fucked him and that they had slept together. At least he thought that was the case.
Toward the end of the meeting Jack said, “So we're going to form teams again this year. Everything's the same except for the new guys. Those dark eyes turned to Matt. “Matt...you will be with Nicholas, Marco and,” He referred to the screen of his laptop which sat in front of him, “Liam.” You should meet with them after this, Matt, and work on logistics.
Matt had no idea what the logistics were, and he wondered who Liam and Marco were. And, he realized, he wondered how Rory was. And when he wondered if he felt a little tug of something. It was kind of in his cock, but also in his gut. He had no idea what to do with that.
When the meeting finished, he walked out with Nicholas and saw two guy standing outside the room he recognized and was actually glad to see. He remembered Marco who had been so excited and had filled his mouth twice. He was grinning at Matt and shook his hand with a similar excitement as he had fucked his face. “Nice to see you, Matt.” He had that wicked grin again. Liam was the red-head and in clothes he looked striking, the contrast of his red hair with his dark blue suit was something. Liam shook his hand warmly and said, “Good to see you with clothes on, Matt.” Matt tried to seem casual, cool, but he could tell his face was glowing with embarrassment.
Nicholas said, “Let's go into one of the small offices and talk strategy. He opened the door to a little room that seemed more like a living room: big armchairs and a coffee table. When they were seated, the same dude who let him in came in and said, “Anyone need a drink? Dinner?”
Liam looked up at the guy and smiled. “I could use a scotch, Tom. Anyone else?” They ordered drinks and some snacks and Tom disappeared. Nicholas turned to him. “Tom is the guy who does everything. You'll get to know him.”
It was a strange way of putting it, but Matt didn't think much more about it. They spent the next hour or so talking about who did what and co-ordinating their laptops so they could work remotely, getting themselves all zoom-ready. Tom returned with drinks and some cheese and crackers. Matt was grateful for the drink and as soon as he finished it, Tom reached for his glass and refilled it from a bottle he had brought.
When the drinks were done, Liam and Marco both stood up and Marco said, “Well gentlemen, I have to run. Coming Liam?”
Liam gave him a big smile that seemed odd to Matt. He turned to them and said, “I'll see you next week, if not before. Stay in touch, Matt. We usually have a quick online meeting every morning at seven.”
They left the room and he was sure he saw Liam pat Marco on the ass. Didn't he?
It was just Nicholas, who was sipping his drink and looking at him. Matt started to feel a little awkward as if something was expected of him. Then Nicholas got up and opened a door that Matt had noticed which he assumed was a closet, but turned out to be another room. With a bed.
He frantically tried to think of way of graciously declining what Nicholas was about to offer, but to his amazement, Nicholas stood there, pulling his jacket off, then his shirt. His pants. Then he said, “Well?”
Matt swallowed and said, his voice almost cracking like a teenage boy's, “But I...”
“Come on, Matt. You've done this before. Go with it.”
And then the other door opened and Tom was there. He saw Nicholas who was just in his underwear, which was, Matt noticed, full of hard dick. Tom said, “I'm glad you haven't started.”
Nicholas said, “Right on time. Why don't you help Matt with his clothes. He seemed to be having trouble deciding what he wants.”
Without a word, Tom turned to him. His eyes were bright and his brown hair was curly and he had a big smile on his face. He was slim, but Matt could tell by the way he filled his suit that he was toned. He knelt down in front of him and said, “Let's get you out of these...” And proceeded to pull Matt's jacket off. Frozen, Matt just let him. For some reason he couldn't stop this from happening. Tom was grinning as he pulled his tie off, then unbuttoned his shirt. Then Nicholas was beside him and he took Matt's hand and pulled him up. He looked into Nicholas' big blue-green eyes. Then he felt Tom undoing his pants and then he noticed that Nicholas was now nude and his dick was pressing against his thigh. His bare thigh, because Tom had pulled his pants down and he found himself stepping out of them.
Nicholas moved closer to him. He could feel his breath on his face, could feel his cock pressing against his which, to his amazement, was no longer soft. It was almost completely hard. Nicholas' cock felt hot. Nicholas said, “Matt, we like to invest in more than money. We like to invest in each other. We like to get to know each other really, really well.”
And then he kissed him and at the same time, he felt Tom's mouth engulf his prick. He kissed him really deeply, his tongue exploring all over his mouth and Matt just had to go along with it, just had to let his own tongue join and he suddenly felt intense lust for this dude. Another dude. He pushed his face into Nicholas and Tom mashed their dicks together and tried to suck them both. Matt felt a little nuts. He didn't think he was capable of it, but he pushed Nicholas into the bedroom and threw him on the bed. He wanted this guy. Fuck did he want him. And Tom was right behind. Matt got on the bed and went for Nicholas' cock which he certainly had sucked before. And then he felt it. Tom's face in his ass, his face pushing its way between his cheeks and driving his tongue inside him. With a moan he took Nicholas' cock deep in his mouth, feeling his hands pushing him down on it.
While his throat took Nicholas' rock hardness, he felt – and realized he had hoped – for the feel of Tom's cock pushing at his hole. It was still tender from all the fucking from the weekend, but he didn't care. He didn't fucking care. Tom pushed in and he got up onto his knees and Tom pulled his face around and they had some mouth action at that awkward angle but it felt amazing. It all felt amazing. Nicholas stood up on the bed and fed his cock to both of them so they were kissing each other with a big dick between their mouths and their tongues. Tom fucked him harder, gripping his hips tightly. Matt remembered all the fucking from the other day and this felt...amazing. It was like he'd been doing it his whole life. Nicholas stuffed his prong deep in his face and he was being fucked from both ends. And he wanted more. And more.
He felt completely unleashed as if he had never had sex before. He decided to switch things up. He said to Tom, “You have any lube in this place?”
Tom laughed and pulled out an industrial-sized pump bottle from beside the bed. “We do.”
Matt pumped a few times and started to work it into Nicholas' ass who was now on his back, his legs extended since he clearly knew what Matt wanted. As he worked on Nicholas' hole, Tom licked his ear and said, “And I'm going to take you at the same time.”
Matt wasn't entirely sure what he meant but realized he didn't care. Once Nicholas was all slippery he wanted a little payback, so without warning he jammed his dick deep and Nicholas just grinned, his mouth open, his eyes wide. “Fuck yeah, Matt. I've wanted this ever since I first saw you.”
So Matt aimed for the coming weekend and went to town, but Tom stopped him. “Hold on...”
He stuffed his dick back in Matt and then bit his ear, saying, “Go for it.”
He did. He went for it. He fucked Nicholas hard and each time he pulled back for another lunge, Tom's nice-sized cock went deep into him. It felt like nothing he had ever imagined. Almost too intense. He slowed down a little and leaned down to take Nicholas' tongue and spit. The weight of Tom behind him, in him, felt really good. Really good. He wanted to do this again. With other guys. He would have imagined he would never want this, but now? It just felt right.
He was getting close and he got his hips working harder and Nicholas pulled him down and said in his ear, “When you jizz in my ass, Matt, you get to clean it out.”
By this point he knew what that meant and instead of disgusting him, it sent a shiver up his spine, a shiver that became an epic, full-body orgasm. He threw his head back and felt Tom bite his neck and felt his balls emptying into Nicholas' ass with what felt like firehose-level spurts of cum.
He felt Tom slide out of him and he got around and stuffed his cock into Nicholas' waiting mouth, spewing cum already which splashed on Nicholas' face before Tom emptied his balls into the other guy's mouth, who swallowed and growled at the same time. Tom grinned and leaned down and they were clearly sharing since their kisses sounded very liquid.
Matt, his balls empty for now, got down and started to tongue Nicholas' hole and since he had never done it before, wasn't sure how to work it, but Tom pushed his face deeper and he could get his tongue in, tasting himself, his sharp, tangy cum on his tongue mixed with Nicholas' juices.
He sat up, licking his lips. Nicholas said, “Who wants mine?”
But without waiting for an answer he pushed Tom down on the bed and Tom moved so his face was near Matt's and Nicholas proceeded to jerk a huge load into their waiting mouths, shifting the angle a few times so they both got a few splashes on their tongues. He and Tom shared the load between them, in a nice, long, kiss. He could see getting to like this guy. That should have been a surprising thought. He also realized his mind stopped being surprised. Maybe there were no more surprises. Except the ones he wanted.
The three of them lay in the bed for a while. He and Tom kissed some more, and Nicholas joined in, in a lazy three way meeting of mouths. But then Tom got up and found his clothes. He stuck his head in the little bedroom and said, “I have to run, things to do. Nice to hang with, Matt.” He winked and left the room. Nicholas sat up and said, “Yeah. I have to get home. My ex is bringing our kid first thing in the morning.”
“You were married?”
“Sure. It didn't take. Besides,” and he leaned down and gave Matt some more tongue, “This is way better.”
He got off the bed and dressed. Matt watched him slide his underwear on. His legs were nicely toned, but not too muscular. His chest – with all the curly hair – was taut, but also slim. He had never really noticed guy's bodies before, but he realized he was enjoying really seeing them. Tom was also slim and he started to get the sense that if he was going to like guys, it was slimmer guys he liked. He thought of Rory who, while not being slim exactly, was not bulky or built.
And as he watched Nicholas leave with a little wave, he lay naked on the bed, his ass still a bit sore, the taste of cum in his mouth, and thought of Rory. He went into the other room and got his phone. He decided to text him. He sent a friendly hello and waited. It was earlier in Vancouver.
Sure enough, his phoned pinged and there he was. Matt suggested a video call, and right away he saw his face. It was still light in Vancouver, dinner time in the summer. He seemed happy to see him, his electric blue eyes intense, his pale face and equally light hair a real contrast. Matt found himself actually longing for him. Ok, that part was still surprising.
“How's it going? How was your first meeting?”
Matt thought a moment. “Interesting. Everyone seemed nice and that big pdf is a real page-turner.”
Rory laughed and sipped a beer that appeared on the screen. “Yeah. It's a lot. How did you feel seeing everyone again?”
Matt knew what he meant. “Oh...fine. I hung out with Nicholas and Tom afterward...”
Matt knew he didn't have to say more, because Rory had the biggest grin on his face. “Oh really. You got some payback, I guess?”
“Something like that.”
“I can tell because you aren't wearing anything, are you? What did you think of Tom?”
“Well...he's eager to please, let's put it that way.” Matt felt strange talking so openly about what he had just done. But he realized it was kind of exciting. His cock certainly thought so.
Rory had little smile on his face. He tilted the screen of his laptop and suddenly Matt could see his big pale cock all hard and ready, his track pants down around his knees. Rory said, “How interesting?”
Feeling foolish, but turned on, Matt pointed his phone at his crotch where his cock had certainly chubbed up. He said, “I just got off, Rory...I don't know if I have it in me.”
“Let's find out. Tell me who did what to who.”
So he did. He told him everything. He told him how it felt when Tom's face was in his ass, he told him what it felt like when Tom sucked Nicholas and him at the same time, he told him what it was like to fuck while being fucked. He couldn't quite believe he did, but he wanted to. And was turning him on like crazy to do it. He was getting really hot telling Rory who clearly was enjoying it just as much. He started to grunt and moan as Matt talked and then he said, “I wish I was there with you, Matt.”
“What would you do?”
“Oh fuck, I would totally ream you. I would stuff this big cock in your sloppy hole and take you into space.”
“Hard?”
“As hard as I could...fuck, Matt...I'm close...I wish I was there with you...fuck...fuck...I wish we were kissing....fuck!”
Matt was getting close himself. At first he didn't think he could, but the more turned on Rory got, the more he was right behind him and soon, as he fisted his streaming dick, he started to spurt again and he pointed the phone down, really close, so Rory could watch the cum pour out the end of his dick.
He heard Rory's voice. “Eat some...”
He took a big fingerful and moved the phone and brought it to his mouth and cleaned it off. That seemed to do it and Rory managed to tilt the screen even more and moved it closer and his big pale cock burst, several ropes going straight up and then down all over his moving hand, coating his fingers. Then he tilted his screen and sucked all the cum off his hand and fingers.
Matt said, “Nice, Rory. That was...really hot.”
“I wish we were kissing, but this will do.”
Thinking a second, he said, “Will you be back anytime soon?”
Rory's face got still. “Not sure. Maybe in September? Jack has given me a ton of work to do setting up another office.”
“Oh that's why you're there. He didn't say.”
“Typical Jack. He likes to keep people guessing. Asshole.”
“You don't like him much?”
“He's an amazing investor, but as a person? At least he has big dick and knows how to use it, that's all I can say.”
They talked for a while, but finally Matt said, “Rory...I've got to sleep...thanks for the chat...and...well, you know.”
“For the video fuck? Yeah, that was cool. I'll buzz you tomorrow.”
They rang off and Matt got into bed. He was really tired again and decided sex did that to him. Guy sex, apparently. He wondered, just before he went to sleep, if he should hook up with a woman and see what would happen, as if wondering if something had changed. But he fell asleep before he could think about it any more.
