The Perfect Night Changes Depending on Who You Spend it With
Just like he’d promised, Leo had foisted his work off on one of his friends when Isaac had come to the fortress, and he had only had to wait a minute or two while Leo went to go change before taking him out on their date.
They’d gone to a really nice supper at a place that made really fancy meat cakes that tasted really good and not at all like meat cakes usually tasted. The restaurant was owned by some fancy royal chef from out east who’d moved to Three Hills and been unable to get a job working in the castle, probably because of racism. But the food was good and the boy who’d brought it to them had been wearing tight shorts, and Isaac hadn’t felt bad looking because Leo had been looking too.
“You didn’t have to pay,” Isaac said, holding Leo’s hand as they left the restaurant, heading south.
“Of course I did, knights are chivalrous,” Leo told Isaac. He smiled. “Besides, I wanted to. When you take a cute boy out for supper, you pay for him. Everyone knows that.”
“Exactly, so I should have paid for yours,” Isaac shot back.
“Hey now,” Leo said, smiling. “You can pay next time. Let me handle tonight.”
“Well, I guess I already did that, didn’t I?” Isaac asked, walking closer to Leo. “You’ve been doing a very good job handling everything.”
“Hm, I’ve got more things to handle.” Leo squeezed Isaac’s hand. “There’s somewhere else I wanted to take you. I think you’ll really like it and this is a great night for it.”
“Okay.” Isaac smiled, looking around. It was a cold night, and a cloudy one, with a stiff wind blowing, so hopefully it was an indoor thing. And hopefully it was a naked thing. “What is it?”
Isaac looked over at him, giving a smile. “You want to wrestle?”
“No. Well, eventually. But I mean watching wrestling.”
Hm. Isaac didn’t really like violence, but wrestling was basically just fucking with clothes on, right? He could probably handle it by just pretending the wrestlers were naked. Leo was doing something nice for him, so he didn’t want to be a jerk about it. “I didn’t know you could watch wrestling.”
“Oh yeah,” Leo told him, clearly excited. “There’re a couple of teams here in the city. It was something I missed when I first came here, because I used to do it at home.”
“You used to wrestle, or you used to watch wrestling?” Isaac wondered, hope in his chest. And his dick.
“Both,” Leo said, fanning the flames of Isaac’s new fantasy. “I mostly watch now, because I’m too busy to really keep in practice.”
“Really?” Isaac looked Leo over. “You’re a knight. I’m sure you keep in shape.” Isaac could see that Leo kept in shape, and the tight clothes he’d been wearing when they’d met before clearly hadn’t been a one-off. Even in the dark Isaac could tell that he wasn’t wearing smallclothes, and if it were lighter he didn’t think he’d have to look too hard to see what he was getting into with Leo, or rather what Leo would be getting into him.
“I guess so,” Leo agreed. “But they’re pretty different skills, so they’d want me to practice a lot, and I can’t. But I go to watch, and your timing is perfect, because my favourite ring is open tonight.”
“Oh?” Isaac asked.
“Aw, come on, tell me!”
“Nope, you’ll just have to wait and see.”
“I’ve never been good at waiting to see,” Isaac informed him.
“To tell you the truth, neither have I.” At that, Leo stopped walking, pulled Isaac into a kiss that Isaac was surprised but in no way disappointed by. He was a good kisser. “I’ve been wanting to do that since I saw you again. But we’ve waited six months, so I can wait twenty more minutes if you can.”
“I’ll try, but I’m not sure you did anything but burn through my famously short patience,” Isaac warned, slightly out of breath from the kiss.
Leo laughed. “Come on, I picked this restaurant because it’s not far from where we’re going.”
He wasn’t wrong. He led Isaac just a few short blocks to a low building. Leo opened the door for Isaac, letting him lead into a foyer with a desk, where they waited in line behind just two other people. Leo put some coins on the counter as they stepped up. “Hey, Dolly.”
“Hey there, Leo,” said the girl working there, taking the coins. “Who’s this?”
“My friend Isaac. I’m going to get him interested in the sport.”
“Well good. Maybe he can convince you to finally start competing here,” said Dolly, whose curls bobbed as she smiled at Isaac.
“No promises,” Isaac told her, returning the smile. “He’s got a mind of his own.”
“I know,” she said, openly undressing Leo with her eyes. Leo was blushing a little and he pulled Isaac away, to a big set of doors. “Bye, Leo.”
“She’s got a crush on you,” Isaac teased.
“I’m pretty sure imagining guys wrestling just makes her horny,” said Leo. “Which, you know. I totally get.”
So did Isaac. “So do you come here for the sport or for the boners?”
“Right now I come here because I’m hoping for a second date with a cute boy and I want to impress him.” Leo told Isaac. He led him past the big doors and to a smaller door, which he held open again, and which led to some stairs. Leo took him down those stairs and into a circular room that overlooked a smaller, enclosed area. “Normally I watch from up there, but since you’re special I got us a better view.”
Isaac looked up, saw another ring around them, much larger. There were more people up there than down here, which was pretty empty except for a few people. “Wrestling doesn’t draw a big crowd?”
“On other nights it does, but most people have pretty bad taste,” Leo said. The room they were in was pretty dark, and Leo took Isaac halfway around it, and they leaned together on a low wall that overlooked the lower area that was lit by some really big lanterns. Isaac guessed that was where the wrestling would happen.
They were pretty much alone, and that didn’t really change, only a few more people showing up on their level and more populating the top ring. A door opened and a man in a robe came out. “Good evening, everyone,” he said, in a booming voice. There were some cheers. “Let’s waste no time, and get you right to tonight’s bouts! First up we have two of our veterans, Adam the Snake and Ronny Red!”
People cheered as another door opened down there and two guys about Isaac and Leo’s age came out. Isaac blinked, standing straighter. Both of them were wearing the smallest smallclothes Isaac had ever seen, cut to be basically a sling that kept their dicks in place, and nothing else. They waved at the audience, smiling, and then shook hands before facing each other. One of them had red hair and the other one had a snake tattoo coiling all the way up his right leg and into the front of his smallclothes, leaving no mystery about where its head was, so it wasn’t hard to guess which wrestler was which.
“You could have mentioned what the wrestling uniform was,” Isaac said as the man raised a hand.
“And spoil the surprise?”
Isaac snorted. The wrestling started, and the two guys went at each other, grabbing and grappling and trying to pull each other to the ground and just generally touching each other all over. Isaac wasn’t going to pretend to understand wrestling, but he sure did understand naked guys groping each other, and watched with way more investment than he’d thought he might have.
His investment strained against the front of his pants as Leo’s hand rested on Isaac’s thigh. As Adam was pinned to the ground by Ronny, who Isaac was pretty sure gave a few good celebratory humps while he was there, Isaac shifted positions so that Leo’s hand was right near his boner. “Oh good, you are having fun,” Leo teased.
Isaac nodded, “I could be having…more fun,” he offered, reaching down and untying his pants quickly. Leo grinned and slipped his hand inside while the two wrestlers got up, left, and were replaced after a minute by two more.
Hank Major and Underdog were maybe a year younger than Isaac, but they were dressed the same way, and both Isaac and Leo watched them closely as they went at it, standing up for way longer than the other two had. Over the course of the match Underdog’s smallclothes got pulled down, but that didn’t stop him from wrestling his way to victory, finishing the match with his leg around Hank Major’s neck just as Leo finished Isaac off right into his pants, the crowd’s cheer covering Isaac’s gasp.
As Leo took his hand away, Isaac moved over, sliding in between him and the wall so he could have Leo’s boner against his ass, just to give Leo ideas in case he hadn’t already had them. He smirked over his shoulder, let Leo put a hand around his middle. “This is fun,” he said. Both wrestlers were standing up now, and Hank Major had popped out of his clothes, a good part of his boner showing, which he didn’t seem bothered by as he shook Underdog’s hand. For his part, once that was done, Underdog just kicked his smallclothes the rest of the way off and tossed them upwards, right at the spectators. And right at Isaac.
Isaac may have used just a little bit of Dark to make sure he caught them, and Underdog grinned up at him, waving before putting his arm around Hank Major and walking out of the ring with him.
“Thought you’d like it,” Leo murmured, his other hand slipping into the back of Isaac’s pants now. “And you got a souvenir.”
“Bet I can convince you to wear this for me.”
“Underdog’s a lot smaller than I am.”
“I know.” Isaac licked his lips as Leo slipped a cum-slicked finger inside him. “You really should start competing. I’d come cheer you on.”
Leo snickered, kissed Isaac’s neck. “The next match is going to start,” he said.
The next two wrestlers were named Little Charlie and Big Mouse, and they were the same size, though the bulge in Little Charlie’s smallclothes suggested that wasn’t true where it counted. They got started slowly as Leo fingered Isaac, his boner pressing hard against Isaac’s butt.
To make sure Leo knew he was having a good time, Isaac used a little Dark to pull down Leo’s pants, and his own, just to free everything up. Nobody could see them anyway, and anyone who could would only see them hugging. “I’d kind of thought our first time would be more romantic,” Leo said quietly, leaking all over Isaac’s butt.
Isaac grinned. “Well, I didn’t really know what that meant a year ago, but you took me for a nice dinner and now we’re watching naked guys grope each other for fun. I may be new to all of this, but I can’t think of anything more romantic. But if you want to wait until we’re somewhere else…”
“No, I’ve been waiting since the summer,” Leo said immediately. He pulled his fingers out. “As long as you’re happy.”
“Very happy,” Isaac promised.
“Good. Watch this,” Leo said, gesturing to the match. Little Charlie had fallen to the ground, pulling Big Mouse on top of him, and they were fighting to decide who would end up on top. As Leo pressed his cock inside Isaac, Big Mouse ended up winning, and he tugged his own smallclothes aside and pulled his cock out. He got Little Charlie on his stomach and pushed his cock right past the tiny strip of fabric that covered their buttcracks. And Big Mouse started fucking his opponent, right there in the ring while the audience cheered.
“Is that allowed?” Isaac asked. The guy overseeing the match didn’t seem to have a problem with it, and clearly nobody else did either, including Little Charlie, who wasn’t trying that hard to get away. Isaac could see his face from this angle, and he was clearly enjoying himself.
“Of course it is,” Leo said, starting to move inside of Isaac. “Why do you think this is my favourite ring?”
“I thought maybe because it lets you do this without people seeing,” Isaac breathed, squeezing Leo.
“I don’t care much if people see.”
“Me either.” Isaac grinned. “See, we’d make good wrestlers.”
“Obviously.” Leo fucked him at a much slower pace than Big Mouse fucked Little Charlie, but he barely lasted any longer, shooting inside Isaac just as Big Mouse was standing up to be declared the winner. He turned and made Little Charlie lick his dick clean before helping him stand with a hug and a big kiss.
“I could stay here the rest of the night,” Leo said, nuzzling Isaac’s neck as Big Mouse hooked a finger into Little Charlie’s smallclothes and led him out of the ring.
“How many more matches are there?” Isaac asked.
Leo shrugged. “They usually have a fair few. Probably like ten?”
Isaac grinned, snuggling into Leo’s hold. “Stay there the whole time and I’ll wear Underdog’s uniform for you.”
“Deal,” Leo said immediately, and Isaac laughed, watching the next wrestlers come out. Judging by their matching uniforms—two pairs of red smallclothes and two of black—and the fact that there were four of them, it looked like this one would be a team event. Isaac was having a great time, and that didn’t change once for the whole night.