Takeru and Patamon's Awkward First Time

Story by Liariv on SoFurry

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I have not been in a good mood to write recently, but this popped into my head last night and I have been able to visualize it better than I have anything in months, so I wrote it in a day. It is not like stuff I normally do! Also, it is my first story to incorporate elements from Digimon Adventure Tri!https://docs.google.com/document/d/1h7H4zMDJWf4aZ71Odimt3cGm8kaQ7tOgsGJ6NH-v1v8/edit


Warning: This story contains descriptions of sex between a human and a Digimon, reader discretion is advised. Also, this story is different from stories I normally do, it's somewhat of a vent story, and is the most realistic story I've ever done. You have been warned.

***

Takeru Ishida sat at his desk, working on an assignment for school. He was hardly sure what the assignment was about anymore, and was just writing down whatever came into his head. His Digimon, Patamon, was relaxing on his bed. Once Takeru had reached what he believed to be a satisfactory word count, he lay back in his chair and took a drink from a glass of juice on his desk. Patamon opened one eye and say Takeru was no longer busy, he fluttered over, and alit on Takeru's lap, looking up at his partner.

"I'm finally done!" said Takeru, peering down at his Digimon, and placing a hand on his head, feeling his short fur, before taking another drink.

"Umm. Takeru..." squeaked Patamon, a blush just slightly visible under his thin fur, "Can we talk about sex?" Takeru gave a splutter, he was so surprised by what Patamon had just said that he almost choked on his juice.

"Wh-What? Where did this come from?" Takeru said with a tone of utter disbelief in his voice.

"Well, I was in the cyberspace the other day, and I overheard Gabumon say to Agumon that having sex with Yamato had really brought them closer together and he had really been enjoying it, then Agumon agreed and said the same thing about Taichi. I bet if we have sex then it'll bring us closer together" explained Patamon earnestly.

"Well, that's quite something!" Takeru said as he listened to Patamon's story. Being a teenager, Takeru of course considered sex on a regular basis, but he had never thought about sex with Patamon before, and he couldn't believe what he'd heard. Did Taichi and Yamato really have sex with their Digimon?

"So, do you think we can have sex?" asked Patamon.

"Umm, I dunno. We'll see..." said Takeru. He was pretty flustered by the whole experience, and he needed more time to think about it.

"Okay" replied Patamon, snuggling in and getting comfortable on Takeru's lap.

***

Several days later, Takeru was visiting his brother Yamato at his dad's apartment. Their parents were separated. Takeru lived with their mother, and Yamato lived with their father, although the two brothers still saw each other on a regular basis. They had been sitting in Yamato's room for a while, and had been talking about all sorts of things, Takeru's Schoolwork, Yamato's music, their Digimon, and other things that Takeru could hardly remember. Yamato's Digimon, Gabumon, was nowhere to be seen.

"Umm, Brother..." stammered Takeru. "Is it okay if I ask you something kinda personal?"

"Yeah, I guess" replied Yamato.

"Well, have you ever, I mean, do you ever..." Takeru had to stop beating around the bush, and just spit it out. "Do you ever have sex with Gabumon?" Yamato was left speechless. He eventually began to stammer out an answer.

"W-What? No! I mean..." Yamato began, but Takeru cut him off.

"Patamon told me." Takeru stated. Yamato gave a sigh.

"Well, I guess there's no point in hiding it anymore" said Yamato. "I really need to have a talk with Gabumon about being more discrete. So tell me, why do you ask?"

"Well, Patamon..." Takeru began, now it was his turn to be flustered. "Patamon wants us to try having sex too, and I thought since you're my brother and all I could ask you for advice."

"Sure thing, I can give you some advice!" Yamato replied. This was a pretty weird thing to talk about, but his brother came to him for advice, and he couldn't just ignore him. "I'm sure you know the basics of sex already, but since Patamon's a boy that makes things a little bit more complicated. There are all sorts of things you can do with him still though, like playing with his..." Yamato hesitated for a second. "Playing with his penis or his butt, or he can play with yours. It might take a while to find something you both like, but just try what feels right."

"Okay" said Takeru, nodding and trying to take everything in.

"Hang on a second" said Yamato. He stood up, and opened up the bottom drawer of his bedside table. From the drawer he pulled some condoms, and a small bottle of lube and handed them to Takeru. "It's important to do it cleanly and safely. You know about condoms already, right?" Takeru nodded. "Good. You should be able to get away with oral without a condom since it's Patamon, but if you're gonna do it in the butt, be sure to use a condom and lots of lube."

"H-Hang on..." stammered Takeru. "Do it in the butt?"

"Well, like I said, since Patamon's a boy, if you want to- well- penetrate him, your options or limited... Or if you want him to penetrate you as well, I suppose. You don't know about anal sex? Well, to do it, you put your penis in your partner's butt, you just need to be slow and careful and use lots of lubricant, also you should probably use your finger first, so he can get used to having something inside him, and be sure to have a towel handy, Digimon can be messy. Got all that?" Yamato asked.

"Y-yeah, I think so." said Takeru, a smirk starting to form across his face. "Is that the kind of thing you do with Gabumon?"

"Now now, a gentleman never tells!" said Yamato coyly, "I hope my advice has helped, so remember, be safe, have fun, and do be gentle with Patamon! He's only small!"

"Thanks a lot brother!" said Takeru, standing up and giving Yamato a hug. "I don't know what I'd do without you"

"You're welcome Takeru," Yamato replied, hugging back. "Look at the time, you'd better get going!" Takeru looked at his watch, it was much later than he thought.

"I better had. Thanks again!" he said, before Yamato walked him to the door of the apartment and he started off home.

***

Once Takeru had gotten home, he went to his room and turned on his computer. He pulled out his phone and sent a text to Patamon, and no sooner than the message had been sent, Patamon jumped out of his computer screen and landed on his lap.

"Hey Patamon, good news! I got some advice about sex from Yamato, so we could try it tonight! You know, if you want to..." Takeru said, feeling his heart flutter at the mere thought of suggesting such a thing to Patamon.

"Sure, I'd love to!" replied Patamon. "What did you learn from Yamato?"

Takeru recounted everything Yamato had told him earlier, including showing Patamon the condoms and bottle of lube. Patamon, like Takeru, seemed to know some parts already but some he didn't seem to have any idea what Takeru was talking about until he explained further. Before Takeru could finish telling Patamon everything, his mother called them, saying it was time for dinner, and once they had eaten, Takeru realised he still had homework to do, so he completed it while continuing to talk to Patamon about sex, and the night they were soon going to be spending together.

***

Once Takeru had finished, he got up, and sat down on his bed next to Patamon. He lay back, resting his head on the pillow, and Patamon climbed onto his chest.

"You ready?" Takeru asked, looking into Patamon's large eyes.

"Yep" replied Patamon. Takeru wrapped his arms around Patamon, and pulled him close. He pressed his lips against Patamon's, and gently slipped his tongue into his Digimon's mouth. He felt Patamon shiver as they kissed. Using his tongue, Takeru explored Patamon's mouth, running the tip of his tongue over Patamon's tiny teeth. He felt Patamon's tongue push against his, but it was far too weak to put up any real resistance. Takeru felt kind of sorry for Patamon, so he relented, letting the Digimon's tongue into his mouth.

Takeru could feel Patamon's tongue in his mouth now, exploring his mouth just as he had explored Patamon's moments before. As they kissed, Takeru ran his hands over Patamon's soft fuzzy back, and played with his ear-like wings, or were they wing-like ears? Before long, Patamon broke the kiss, and gazed into Takeru's eyes.

"Ahhh... I feel... So, I dunno... Hot..." gasped Patamon between deep breaths. He was sitting on his hind legs on Takeru's chest, and Takeru noticed a bulge in the area of his crotch that wasn't usually there. Takeru placed a hand on Patamon's front, and gently ran it down his soft belly, causing Patamon to gasp and shiver. Once he reached Patamon's crotch, he groped around a bit, before figuring out what Patamon had going on down there. He had a pouch, like a double sided fold of skin covering his genitals. As soon as Takeru grabbed his crotch, he relaxed it, allowing Takeru to pull his cock and balls out of it. Takeru thought it was weird, like he had a foreskin covering everything.

Once Patamon's cock was free from its pouch, Takeru took a few seconds to examine it. He'd never seen Patamon's cock before, and it was strange to say the least. His balls were pretty normal looking, they were fuzzy and cream coloured much like the rest of his underside, however his cock was pink, cone shaped, and tapered to a point. It was also small, much smaller than Takeru's, but it matched the size of Patamon's body well.

"Is it okay if I suck it?"asked Takeru, his eyes flicking back and forth between Patamon's face and his cock.

"Yeah, sure" replied Patamon, sounding somewhat unsure of himself. Takeru pulled Patamon closer, until Patamon was practically straddling his face. Takeru felt Patamon put his hands on his head for support, and he held his hands against Patamon's back so he wouldn't lose his balance. Takeru took Patamon's cock in his mouth, and began to gently run his tongue over his length. He felt Patamon moan and give small squeaks as he sucked, as well as squirm around. Soon enough, Patamon gave a yelp and tried to pull away.

"Ahh! Takeru! Stop! I don't like this!" he squealed, pushing back against Takeru's head. Takeru quickly released Patamon, and he tumbled back onto Takeru's chest.

"What's wrong?" asked Takeru with concern. "Did it hurt?"

"N-No..." gasped Patamon. "I just... Didn't like how it felt."

"That's okay" smiled Takeru, gently stroking Patamon, "We can try something else." Takeru lifted Patamon up and placed him on the bed beside, him. "First, I'd like to get out of these clothes though." He unbuttoned his shirt, and took it off, and slid off his trousers and underwear, leaving him lying naked on the bed. He noticed Patamon's boner had gone down a bit since he had sucked him, but Takeru was still hard as a rock.

"Can I touch you?" asked Patamon, looking up and down Takeru's naked body.

"Sure thing" replied Takeru, turning around so Patamon was sitting in between his legs. He figured from Patamon's perspective his cock probably looked quite formidable. Patamon stood up on his back legs, and put his tiny arms on Takeru's cock. He began rubbing and examining his partner's length, pulling back his foreskin and examining the head, as well as fondling his balls. "Well, what do you think?" asked Takeru.

"It's... big!" Patamon replied, continuing to touch and examine his dick.

"Can we try something else now?" asked Takeru.

"Like what?" Patamon replied.

"Could I try playing with your butt?" Takeru asked, feeling embarrassed he even suggested such a thing.

"Uhh, sure, okay" said Patamon, sounding as unsure of himself as ever. Takeru lay down, and picked up Patamon and sat him on his chest once again.

"Think you could turn around?" Takeru asked. Patamon did as he was told, and turned around so his butt was facing towards Takeru's face. Takeru grabbed the bottle of lube off his bedside table. He looked back at Patamon, and took notice of his anus, between his pert butt cheeks, balls, and tiny tail. He suddenly felt an urge to lick it, but he decided against it. He figured Patamon probably wouldn't like that either. He squirted a generous amount of lube onto his fingers, and gently pressed his finger against Patamon's anus. Patamon's anus contracted, and he gave a gasp.

"Cold..." moaned Patamon. Takeru slowed down, and gently rubbed the outside of Patamon's anus with his finger.

"Shh, it's okay, just relax" said Takeru as reassuringly as he could. He felt Patamon's anus relax, and once he was sure Patamon was relaxed enough, he gently pushed his finger into Patamon's butt. Patamon winced and breathed in sharply past his teeth, making a hissing sound. Takeru held his finger in place inside Patamon. "Are you okay?" Takeru asked, worriedly.

"Yeah, fine..." Patamon moaned. "Just... Go slow." Takeru gently pushed his finger deeper into Patamon's ass. He could feel Patamon's tight inner walls squeezing down on him, the pressure and the heat was incredible. He could only imagine how it would feel against his cock. He pushed his finger in up to the knuckle, and gently drew it out again. Every tiny motion seems to make Patamon either twitch, moan, or wince. The more Takeru slid his finger in and out, the looser Patamon's butt seemed, and Patamon's moans and squeaks of pain seemed to be giving away to moans and gasps of pleasure, although it was hard to tell.

"Hey Patamon, think we could do it in the butt now?" asked Takeru. Fingering Patamon had made him really horny, and he felt desperately in need of release. He hadn't masturbated since Patamon had first mentioned having sex from the anticipation of it all.

"Yeah, I think so" gasped Patamon. "Just be slow and gentle." Takeru gently drew his finger out of Patamon's back side, and Patamon turned around to face Takeru. Takeru grabbed a condom and took it out of the wrapper. He leaned up so he could get a good view of his cock, pulled his foreskin back, and slid the condom on over the head of his cock, rolling it all the way to the bottom. He squirted some more lube on his hand, and rubbed it all over his cock. He felt like he was about to cum from rubbing himself alone, but he wanted to save it for Patamon.

"You ready?" he asked, looking down at Patamon, who was lying on his belly on Takeru's chest. Patamon gave a nod, and Takeru grabbed his cock, and placed it under Patamon's tail. He pushed forward, but it didn't go in. Rubbing against Patamon's cheeks felt good enough on its own, but Takeru wanted more, He moved his cock up and down, until he found Patamon's anus, and began to push his cock forward. Suddenly, without warning, it slid deep into Patamon's ass, almost all the way in. Patamon gave a deafening squeal.

"Ahh! Takeru! Stop! Stop! Stop! It hurts! It hurts! Take it out! Take it out! Take it out!" shrieked Patamon, flailing around and flapping his wings wildly. Takeru wasted no time in grabbing Patamon and pulling him off his cock. Patamon stopped flailing and let Takeru hold him. There were tears in his eyes and he was gently sobbing.

"Shh, I'm so sorry Patamon." Takeru said, hugging him tightly and giving him a kiss on the forehead. "We don't have to have sex anymore tonight, maybe doing it in the butt isn't for you." Patamon didn't say anything, he just hung onto Takeru tightly and cried quietly. Takeru grabbed the towel from beside the bed, and began gently cleaning the lube off Patamon's rear end and his own cock. He pulled the condom off his dick as well. Once they were both clean, he examined the towel. There were a few tiny specs of blood on the area he had used to clean Patamon's butt. He felt bad about that, but it had been an accident and he was sure Patamon would forgive him. "I'm pretty tired, let's get some sleep, shall we? We can try having sex some other time, and do it better next time."

"I'd like that," said Patamon with a smile, he had stopped crying, but his face and eyes were still a bit red. Takeru pulled the covers over them, and hugged Patamon close to him. He never wanted to hurt Patamon in that way again. All in all, the sex had not been a success, but in a way, it had brought them closer together.