Kai’s first time

Kai was never bad looking, but also not really ever considered especially handsome. He was fairly skinny, had ginger hair, green eyes, and stopped growing at 5’6”. He never cared for mainstream “masculine” sports, being more fascinated generally considered “feminine” sports. This seems completely normal, but Kai thought he was very different from a young age, although he wasn’t quite sure how. One indication was whenever he saw other guys changing (whether it be at school, or in swimming pool locker rooms), he couldn’t help but shoot curious glances. While he enjoyed undressing other boys with his eyes, Kai’s favourite fantasy however, was James.

James was the epitome of heterosexuality. James was athletic, playing a medley of sports, including, but not limited to: baseball, football, and especially, hockey. He was good -hell, even great - looking, having luscious, dirty blonde hair, defined muscles, had a grand stature of 6’4”, as well as eyes both as captivating and blue as the ocean.

James and Kai were friends since the second grade, and, despite their differences, being almost polar opposites, were inseparable. The two of them did absolutely everything together, going to theme parks, movies, biking, and in their teenage years, even jerking off. They also shared somethings, including secrets, mutual interests in WW2, and almost, a birthday. James turned 18 a measly 3 days before Kai.

To celebrate Kai’s birthday, James decided to get a hotel for both of them to have a short trip to the mountains on a weekend.“Happy birthday Kai! I hope you’ll love your birthday present. I booked us a hotel room in Banff for this weekend!” James exclaimed while handing Kai a pamphlet from the hotel he booked.

Kai was elated  to get to spend some alone time with his friend, and he said to James, “Wow, thank you so much dude!” Kai’s birthday was on a Tuesday, so he had to sit through school on Wednesday, Thursday, and Friday, anticipating the weekend get-away. Friday night finally came, and Kai was very ready to get picked up by James. They had planned to leave for Banff (a 3 hour trip from their houses), on Friday night to make the most of Saturday.

Kai had packed the night before, which meant he would be completely ready for James to pull up to his house at 4 PM sharp. Kai was known to over prepare, and this was no different. Just in case his fantasies came true, Kai shaved all of his little body hair for James, packed condoms, and of course, lube. All of these would soon come in handy.

Kai was outside waiting for 4PM, and with it, James to arrive. Sure enough, 4PM rolled around, and Kai could hear the distinctive sound of James’ 2003 Pontiac Firebird roaring down the street. Honk honk! James laid on his horn before his car even stopped. He always did this so Kai knew he was there, but this time it was unnecessary, as Kai was anticipating James’ arrival outside.

Kai eagerly threw his bags in the back, and hopped into the front passenger seat.

Fast forward to Kai and James getting checked into the hotel, and sitting in the room. “Hey, I haven’t gotten any relief for a few days, do you mind if I jerk off?” James asked.

“No, go ahead, stud!” Kai responded. With this, James took his shirt and shorts off, then practically ripped his tented boxers off. James was horny. Not horny, but, horny. 

While James was busy doing this, Kai hurriedly dug to the bottom of his bag to fetch his bottle of lube, knowing that James never had his own, and would ask for some soon. Kai never was very coordinated, but he accurately threw this bottle of magic right into James’ now free, and ready hand. James caught the bottle with his left hand, and flicked it open with his right hand. 

James emptied what seemed to be a lake of lube onto his hairy dick. He slowly rubbed the lube all over his growing cock. “Oh my god,” James groaned, “I needed this sooo bad dude!” 

Kai smiled methodically, his brain’s gears turning in thought. Could it be? Would he finally get his dream? 

“I’ll be right back. And don’t be so loud.” Chuckled Kai, as he made his way to the bathroom. Along with the lube and condoms (one of which he didn’t plan on using), Kai packed a face cloth. Kai had used the bathroom before leaving his house, and pretended he wasn’t hungry when James asked what he wanted to eat. This meant that all he had to do wash himself to be ready for anal. 

Quickly, Kai turned the tap to get some warm water. While waiting for the water to heat up, Kai dropped his pants and underwear to the ground, and jumped put of his shirt. Kai put the cloth under water, turned the tap off, and proceeded to wipe himself extra clean. Finally, he was ready.

Kai knew what to expect after opening the door. James’ left hand behind his head, displaying his hairy, but maintained armpit hair, his right hand stroking his 8.5” dick, a shaved chest and stomach, a beautiful bush, and hairy legs. Kai found out he was correct after coming out of the bathroom.

James had his eyes closed, and was focused on the sloshing of the lube on his dick, so he didn’t hear or see Kai coming to his bed naked and aroused.

Kai placed himself onto James’s bed, and asked, “Need some help James?”

James was shaken out of his lust, and almost jumped off the bed from being frightened. “Jesus Kai! A little hey first could’ve worked. Also, did you just ask to give me a hand job? You know I’m straight, right?” James said.

Kai was a bit disappointed, but was still set on his goal. “I figured you just might of wanted some help. Who cares if your straight or gay, a had job is a hand job. Just close your eyes again.” he almost pleaded.

James wasn’t sure about it. “I don’t know Kai. It’s fine if your gay, but I don’t want it to wreck our friendship…” James thought aloud, “Ok, fine. But don’t suck me, just your hand.” James closed his eyes, imagining an ex girlfriend giving him a hand job.

Kai was more than happy with this, and placed his hand on James. “Ok, no sucking.” Kai replied.

Kai expertly navigated James’ dick. He knew exactly what James liked, and he researched  a lot about what to do. James was uncut, so Kai rolled his foreskin back and forth with one hand, and glided across James’ shaft firmly. “Fuck… dude… where did… you - you learn how to… do - do this?” James slowly asked.

Kai smiled, knowing James was loving it. “I’ve been waiting awhile for this, I wasn’t going to try without knowing what to do.” Kai stated matter of factly.

James accepted this answer, but he didn’t have much of a choice, as he was enjoying it a lot, and probably couldn’t have formed a sentence.

Kai then took his hand off of James’ shaft, and cupped James’ balls, massaging them delicately. While simultaneously playing with James’ head, Kai played with his friends balls, lightly pulling on the skin.

If it wasn’t for the lube, Kai would’ve gone against what James said, and started sucking, but instead, he placed his left hand back on James’ shaft to go from the base to the tip, taking his right hand and getting more lube. This time though, the lube wasn’t going on James, it was going on Kai’s finger, and into himself.

Kai stretched himself while working on James. Once Kai thought he was a stretched as his finger could make him, he asked James, “Can you stand up, I have a surprise?” James’ response consisted of nodding his head, and standing up. Kai put his chest on the bed, but raised his ass in the air, on display for James. Kai then asked James another question, “Well… are you going to use it!” As if this was his cue, James just moaned out a, “Yes.”  

James took hold of his own dick, and guided it into Kai. Now it was James turn to show of what he knew (or at least what he could apply from his sexual experiences). He pressed his dick against Kai’s ass, teasing, “Tell me what you want.”

Kai wasn’t going to waste time, so his answer was straight forward. “You, I want you James!” 

“Oh yeah, ” James teased, “are you sure.”

“Mhmm, please.” Kai desperately said.

“Here I come.” James told Kai, as he entered Kai’s ass slowly. “Wow, your tight. This is awesome!” James didn’t even realize he only had the head of his penis in Kai, and couldn’t wait for the rest of what was coming.

Kai was moaning away in euphoria, ahhh. James took pride in his work, and to him, that meant doing it as good as he could. He didn’t think he could wait much longer before he could cum, but he wasn’t even balls deep yet, just halfway down his dick. “There’s still more where that came from!” James declared, showing himself all the way into Kai.

“Holy shit James. You feel even bigger than you look,” Kai said, trying to be coherent in his lustful state, “I never want this to end!”

Kai’s wish of never ending anal didn’t come to fruition, as about 1 and a half minutes into the anal, Kai could feel James’ dick tensing up. “I’m about to cum, Kai.” James excitedly said.

His thrusting quickened. Smack smack smack. Then it slowed to deep, deliberate thrusts. One     rope of cum was released. After that, another. And another. Then one final, large, rope. 

Kai could feel the wetness in him. “That was awesome, James. Are you sure your straight.” Kai laughed at his own statement.

“I’m not so sure anymore, I’ve never felt anything like that with a girl.” James giggled while his dick was softening in Kai. James collapsed onto Kai. One final thrust. Plop, his dick slipped out of Kai.

Kai and James laid there together for hours, until James started getting another erection. “Hey Kai, want to help…” James asked.

Thank you for reading my first story. Any and all criticism, suggestions, etc. are welcome and encouraged.