Kai's Unforgettable Detour

"Are you coming tonight, Kai?"

"Of course, Jasmine. i wouldn't miss it for the world", Kai said with a dumb smile on his face.

"Great! I was hoping to see you there", she smiled as she turned and walked back to her station.

Kai had been working as a server at the Sunset Grill for 3 weeks. He instantly formed a crush on the restaurant's hostess, Jasmine. She was 20, with long curly blonde hair, big breasts, a slim waistline, but with a perfect amount of meat on her bones. It was Sunday evening, the start to the "weekend" in the serving world, and everyone was going to Jasmine's for a party after work.

Kai was 22, 5'11 with an average build. He has been single for 6 months. Since then he's had a few one night stands but he's been going on his longest dry spell since he could remember and it's been on his mind for some time.

"HEYYY KAIIII!"

Kai shuddered to himself as a wave of annoyance washed over him. It was James, one of his fellow servers. James was flamboyant, a mix of white and Korean, and petite at just 5'3. It's not that Kai cared that James was gay, he just found him obnoxious. James had to be the center of attention. He was loud, flirty with everyone he talked to - man or woman. He proclaimed himself as 'one of the girls'.

"What is it James?" he asked with a visibly irked look on his face.

"Are you going to Jazz's tonight?"

"Yeah, why?", asked Kai.

"Oh, no reason, I just know she wants to fuck you is all!" James laughed loudly, heading back out to the dining area to check on his tables.

'Can it just be 9pm yet?' Kai thought to himself.

9pm

Most of the wait staff was gone, along with Jasmine. Kai and James were among the last 3 servers on for the night. Kai changed out of his work clothes and headed out the door.

'Finally. Time for an incredible night' he thought. He would go home, shower and get ready, and could be at the party in less than an hour.

As Kai got to his car, he saw that his tire was flat.

"You've gotta be kidding me" he said to himself. His phone was nearly dead, he had a spare tire but didnt have a jack to change it.

"Kai, what's the matter, babe? OH SHIT, your tire. That's just shitty"

It was James.

'Of course it had to be him. As if I'm not irritated enough' Kai thought.

"Do you have Triple A?" James asked.

"No, I don't drive much, so I've never needed it."

"Wellll, if you'd like, I can drive you to your house, but you live close to Jasmine, right? I live 25 minutes in the opposite direction and I'm not driving back and forth. I need to shower real quick before heading over. Then I can drop you off at your house or bring you straight to Jazz's, whichever you'd prefer."

Left with no other option, Kai agreed. He tried calming himself down.

'Oh well, a minor setback. Now I'm making it my mission to hook up with Jasmine tonight. It's going to happen.' he thought to himself.

James talked the entire ride but Kai paid no attention. James didn't even notice, lost in his own ramblings. They arrived at James' apartment.

"you can watch TV. I'm just gonna get ready real quick and we'll head out" said James. "You can pregame if you want. I have some vodka in the freezer, or beer in the fridge. I also have some weed. I always keep a bowl packed for when I get home after a double shift, hahaha"

'I could go for a smoke after being forced to listen to James for the past 30 minutes' he thought.

"Yeah, I'll smoke a bit" Kai said and he grabbed the pipe. After 2 hits Kai was noticably relaxed. James also took a hit before heading to the shower.

Kai closed his eyes and laid his head back on the top of the couch. He wondered what Jasmine was doing. Thought about what they'd talk about, where the night would lead. Would he make out with her? Get head? Or - God willing - finally have sex? The thought of the possibility got him hard.

Just then, James came out of the bathroom wearing a towel (around his upper body, covering his chest like a woman would wear one). Kai rolled his eyes. 'Of course that's how James would wear a towel' he thought to himself. James had eye liner and a barely noticeable pink shade of lipstick on. His hair was wet and curly, and laid just past his shoulders.

"Just gonna grab some wine and finish getting ready and we'll be off. How's the weed hitting you, it's good stuff, right?"

Kai noticed that he hadn't gotten up since he sat down.

"Yeah, now that you mention it I feel great.

James noticed Kai's erection.

"Yeah I can see that! Am I getting you too hot and bothered in my towel?" James laughed.

"If you must know, I was thinking about Jasmine."

"I'm just fucking with you Kai. I know you're straight. I have perfect gay-dar"

James went to the kitchen and reached for the tallest cabinet to grab a wine glass. In doing so, the towel lifted and exposed the very bottom of his ass cheek, just for a moment. Kai couldn't help but notice how smooth James' legs were. And now that he thought about it, James didnt have any body hair, on his arms, his face, and - as he just saw - his ass. His build was very feminine actually. Not much muscle to be seen.

James finished pouring his wine and walked back to the bathroom. Kai's eyes followed him without Kai realizing it. James closed the door and Kai started thinking. 'Was I just checking out James' body? It must be the weed. Or because I can't stop thinking about potentially hooking up with the hottest girl. 30 minutes from now I'll have my chance.'

"Ok, Im just about ready" said James as he walked into the living room. He was wearing tight jeans and a girly shirt, exposing his midriff. As he walked by, Kai noticed he was wearing a white thong, the strings pulled over his hips. James walked behind the couch and started rubbing Kai's shoulders.

"I can see the tension you're holding in your shoulders. I'm a certified masseuse, I'm just waiting tables until I can build up a clientele."

"That actually feels really good" said Kai.

The weed had cleared any annoyance with James that Kai had in that moment. He closed his eyes and slumped forward, letting James do his thing.

Again, Kai started feeling his pants rise.

"Wow, I really must be doing it for you, huh Kai?? I mean, I know I look hot as fuck, but you can't keep blaming your boners on your thoughts about Jasmine haha"

Kai was speechless. He couldn't think of how to explain it. James sat down next to him, which made Kai uncomfortable.

"I'm kidding!" James said. "And don't worry, your secret is safe with me. I won't tell anyone that my hot-ass body got you rock hard" he joked.

Kai looked at James. His makeup really made him look feminine, almost like a Korean girl.

"I'm really good at keeping secrets" James said as he put his hand on Kai's thigh. Kai froze. Just feeling a touch so close to his junk started to get him growing more. It felt good, he had to admit. So good that he didn't push James hand away.

'What am I doing?' Kai thought to himself, almost panicked. You're not gay, and you are NOT getting turned on by James, of all people. James' hand remained, much to his own surprise. He really thought Kai would have jumped up from his seat by now. The seconds felt like minutes.

'You are not doing this', Kai said to himself in his head. 'Don't go through with this. Push his hand away and stand up.'

James started rubbing the inner of Kai's thigh, causing him to breathe heavily. Again his brain protested, 'Don't, don't, DON'T!'

But his dick had control now, and despite his brain's demands, Kai twisted his hip towards James, letting his shaft slip below James' hand.

James smiled, he couldn't believe how easy it was. He slowly rubbed Kai's still growing cock up and down from over his pants. Kai kept his eyes closed, still wondering if he could fight the urge to go on. For minutes, James teased Kai's dick, wondering what it would look like if Kai let him take it out. Finally, he unbuttoned Kai's pants and slid his zipper down. His cock, still hidden by his boxer briefs, pulsed heavily, a spot of pre-cum formed at the top. James slid his fingers over the top of Kai's briefs and lifted them down over his dick. He was HUGE, he figured Kai was packing, but didnt expect the 8 1/2 inches that he just revealed. James gave it a slight squeeze and pulled his hand towards the tip. A glob of pre-cum drooled out and ran down over James' hand. Kai shivered. James used the sticky mess to lube it up and began working his cock slowly, using only his thumb and pointer finger, teasing from the balls to the tip, then repeating. Kai's legs were shaking in anticipation. Finally, James put his tongue on the tip of Kai's dick and pressed it against his pee hole. Kai moaned. James now used his full hand to properly stroke his full cock up and down, still licking the tip.

"How does it feel so good?" Kai muttered, mostly to himself.

"I've barely started, baby" James giggled. "You're going to get the best head of your life"

He started taking Kai's cock into his mouth, gyrating and going further down each with each bob. James fully removed Kai's pants at the same time. Kai eagerly kicked them off his feet and pushed his pelvis towards the edge of the couch, giving James more room to work his magic. James was taking his whole 8 1/2 inch cock in his throat, leaving it there and circling his mouth clockwise. It felt incredible. Kai was in heaven. He felt like he was hovering over his body, watching himself get the greatest blowjob of his life. Kai was squirming in his seat.

James climbed onto the couch on all fours, still sucking, now perpendicular to Kai. Kai opened his eyes and saw James' thong strings as well as the top of his ass crack. Instinctively he began rubbing James' ass over his jeans. He watched James and thrusted his cock to his sucking rhythm. Any cares about getting head from a guy had disappeared from his mind. He was living in the moment, his brain silenced. James wriggled his jeans down, exposing his smooth bubble butt, only contained by his white thong, letting Kai continue to rub it.

'Fuck, this is intense. I cant believe I'm doing this' Kai thought to himself, tears starting to form in the corners of his eyes.

But he really wouldn't believe what he was about to say next. He was lost in the moment and his mouth started talking for him.

"I need to fuck you" he breathed, almost inaudibly.

But James heard. He continued to slurp on Kai's cock for a minute. He then sat up and straddled Kai's lap, letting his cock rub between his cheeks. He then raised up and let Kai's tip press against his hole. Kai lifted his hips, trying to press his way in.

"Not so fast" James told him. "Just let me do all the work." He was running his fingers through Kai's hair. "I'm going to take care of your every need."

Kai's dickhead popped into James' tiny boy pussy, causing James' to quietly gasp. James then slowly took Kai's enormous cock in, inch by inch. A stream of pre-cum oozed out and down Kai's balls.

"It's so tight!" moaned Kai.

James ass now fully enveloped Kai's cock. He sat there for a moment, letting his muscles relax around it, then began rocking towards and away from Kai, lifting his shirt and pressing his erect nipple into Kai's lips. Kai obliged and began licking circles on it. James' nipples were tiny but puffy, soft.

"Mmmm, that's what i like" he whispered.

They continued in this rhythm for minutes. James rocking back and forth and Kai licking. James then laid Kai down on the couch, still sitting atop him. He started lifting up and down, slowly at first, still getting used to the giant cock inside of him, then faster, lifting almost enough for his tip to fall out before slamming back down. Kai reached over his head and grabbed onto the armrest, bracing himself for James' incredibly intense riding.

"oh my God, James. You're amazing at this."

But at the same time, James was thinking the same thing. Riding Kai, who was very masculine, made James feel even more feminine than usual.

Kai looked down at James' thong, which was now soaked through with pre-cum. The white was now translucent, showing off James' tiny cock. It was about the length and width of Kai's thumb. His pubic area, like the rest of his body, was completely hairless.

James spun around and started riding backwards, looking back to watch Kai, who had his eyes locked on his. Kai started admiring James backside, rubbing his hands all over his back and ass as James rode his cock.

James began rubbing his little clit of a dick inside his wet thong.

"You make me feel so feminine" he said. "You feel so good in my pussy. I want to ride you for hours."

Kai grabbed James hips and began lifting him up and down to his desired rhythm. He needed to take control now.

Kai rocked James up into the doggy style position, with his forearms on the armrest. he hrabbed James' shoulders and started pounding hard. The sound of his balls slapping James ass intensified.

"Oh my god!" James screamed, tears now running down his cheeks. "Your cock feels so good!"

Kai just moaned. He grabbed James by the hair and pulled his head back and began kissing his neck, now fucking him slower, feeling James tight o-ring pull on his dick with each movement, in and out.

"I want you to put a baby in me" James whispered, breathing heavily.

James began ramming his ass back into Kai. Faster. Harder. "I want you to fill me"

"Mmmm, MMMM. I'm gonna burst!" Kai yelled. "DO IT. Give me all your cum!" James demanded.

"OH FUCK, FUCK, FUUUUCCKK!"

A week's worth of cum found it's way out of Kai and into James. Kai was cumming hard. Every rope as intense as the last. It felt like it would never stop. His cum must've been all the way to his stomach by now, he thought.

"I can feel it! OMG it's so warm!"

Kai grabbed James hips and continued to pound away for a minute longer. His cock still game. A second wave came over him. "Oh FUCK, it's happeneing AGAIN!"

Kai had never came twice in one fuck before. By this time, warm jizz began to spirt out of James' ass with every thrust, covering Kai's balls.

Kai pulled out and laid back, physically exhausted. James turned around and began licking Kai's balls clean. Kai just panted, still unsure of what came over him.

"So do you think we'll have a boy or a girl?" James joked.

Kai's post-nut clarity started kicking in.

'What have i just done?' he thought. 'It felt amazing but my God, I just fucked a guy. I came in him. TWICE!' he said in his head. Kai was visibly distraught.

"What's the matter, stud? Was I not good enough?" It sounded like you loved it?

" James laughed.

"I just dont know what came over me, I've never had the urge to do anything like that before" Kai said.

"Hmm, well..." James hesitated.

"What?"

"Well, the weed you smoked was called X Kush. It MIGHT have some aphrodisiac effects." James said, biting his lip.

"Oh my God, so you gave me that, knowing I would get horny??"

Kai was in shock.

"Well it might've got you horny, but it didn't mean you were forced to fuck me... But it was some great sex, right? You came twice for fuck's sake. And nobody has to know." James smiled.

"I guess."

Kai thought to himself for a minute and calmed down.

"Ok...ok. You never talk about this. To anyone!"

"I told you, nobody will ever know, except us."

Kai got his clothes and began dressing.

"Listen, I will admit, the head and sex were great. I just need some time to process what happened tonight."

James got up and poured himself another glass of wine, still wearing just his cutoff shirt and panties.

"So...are you glad I let the air out of your tire at work?" James smiled.

"Wait..you WHAT?"

James had orchestrated the whole thing. He knew that Kai had been horny, watching him flirt with Jasmine all week. He knew if he could get him alone and lower his inhibitions, that Kai would give in. He just needed a little push and he would melt in the palm of his hand...and then mouth and boypussy. It turned out to be a detour that Kai would never forget.