The First Time

Chapter Two

Early the next day, Finn headed off to the library. It was an unlikely lead but he was unsure of where else to start. As he walked, he agonized over how to even ask for what he was looking for. He imagined walking up to the librarian, Turtle Princess. 'Hey, TP, I was wondering if you have any books on doing it in the butt?' He'd have to figure out something better than that before he got there.

For some reason, he thought of his brother. Jake would definitely come up with a less awkward way to say it. But wait a minute. Jake had been with various partners before Lady and Finn knew for a fact that quite a few of them had been guys. Jake would be able to tell him all about how sex worked with two dudes. Finn turned around in his tracks as he decided to pay his brother a visit to ask for advice.

.....

Lady was, thankfully, visiting T.V. and her parents in the Crystal Dimension when he arrived. His brother, still in a fluffy pink robe and slippers, was just starting out his day when he welcomed Finn inside.

"What brings you by?" Jake asked with a yawn, as Finn sat himself down at Jake and Lady's kitchen table.

"Dude, I need homie help. It's urgent," Finn gushed. "Fern and I tried to do it last night, but his thing is massive. Like, stupidly big. It wouldn't fit at all. What do I do?"

The dog made a choking sound and held on to the counter for support.

"Finn, are you aware that it is, like, 7:15 am right now? What the heck are you saying to me first thing in the morning?"

The blond seemed surprised at his reaction. Given the problem at hand, Jake was the obvious choice of person to seek guidance from.

"I just figured since you've slept with kind of a lot of guys you would know what to do," he explained defensively. "I mean this is really important. Are Fern and I supposed to not have sex just because his ding dong is the size of a goblin arm? That would be crazy."

Jake knew that Finn and Fern were deeply in love. While he didn't fully understand it, he accepted and supported it. Finn had grown into a young adult that Jake could respect and be proud of, and despite the rocky start to their relationship, he was growing to love and understand Fern more every day. Still, the idea of digging up his own promiscuous past to give his little brother sex tips to use with his cursed demon doppelganger boyfriend was... a lot. Although he willed himself to keep an open mind, Jake was having a hard time dealing and it didn't help that Finn was being utterly tactless about the whole situation.

"Alright, dude," Jake said in a defeated exhale. "If I help you with this, it's important to me that I don't hear any more descriptions of how big Fern's thing is, okay? That's not something I need to know about."

"Okay, don't talk about the size of it," Finn parroted. "But wait, what about the appearance or the texture?" he asked thoughtfully.

"Texture?! Oh, my glob, dude. No. No more descriptions of any part of Fern's anatomy, at all. Period," the dog said sternly, rubbing his temples.

"But what if it's relevant-"

"Finn...," Jake cut him off in a threatening tone.

The human chuckled sheepishly.

"Okay, okay. Just stick to the facts," he agreed.

"Right," Jake said emphatically. "Sheesh. I'm gonna need some coffee for this," he added before disappearing into the pantry to retrieve the beans and grinder.

Later as they sipped their coffee at the table, Jake summarized the situation as he understood it. The teen wanted to know how to engage in anal sex for the first time and to overcome the difficulties of having a partner with an above-average-sized penis.

Instantly failing to adhere to Jake's request for boundaries, Finn corrected him.

"Not just above average sized, dude, enormous. When we tried last night, it was like trying to fit a candy cane through the eye of a sewing needle. It freaking hurt, and... Jake?"

But the dog was no longer listening. He had laid his head down on the table and was covering his ears with his hands. Finn pantomimed locking his lips and throwing away the key to let his brother know it was safe to uncover them, but Jake had already had enough.

"I can't do this, man," he said miserably, his head still on the table.

"What like, at all?" Finn questioned.

"Uh-uh," Jake groaned. "Some things are just not for an older brother to hear, okay?"

"But, how are Fern and I supposed to do it if you won't help me?" the human whined.

"I don't know, man," Jake sighed. "You're just gonna have to find somebody else. Maybe Bubblegum. I know she and Marcelline are super sex-positive. Go talk to her."

Finn considered this. He wasn't thrilled about the idea of asking his first crush for help with such a private matter. But it would probably be okay, right? Things between him and Bonnibel were a lot different and now their friendship had a solid foundation of mutual respect. Anyway, what choice did he have? Jake clearly wasn't going to be of any use and he was desperate for whatever help he could get.

"Okay. I guess I'll go over to the castle after this," he said unsurely. "Just goes to show you how serious I am if I'm willing to talk to Bonnie about it."

But Jake was still too rattled to congratulate him on this breakthrough. He got up from the table and crossed over to Finn, attempting to take his mug.

"What, right now?" the blond asked, surprised. "But, I'm not finished with my coffee yet."

"Yes, right now," Jake said firmly. "You can take the coffee with you."

He dragged Finn up from the chair and began ushering him out of the kitchen.

"But your mug..." the human spluttered.

"Keep it!" Jake shouted as he shoved his brother out of the door and slammed it behind him.

Finn stood staring at it in shock for several seconds. He took a noisy slurp of coffee from his newly inherited mug.

"What a wad," he said finally, before heading off in the direction of the castle.

                                     .....

Once he was rid of Finn, Jake felt the full weight of his emotional exhaustion. He leaned his back against the door and let himself slide down it to a kneeling position.

He felt guilty for abandoning Finn in his time of need but rationalized that it was quite a lot for the human to ask of him. After picking himself up and returning to his coffee at the table, however, he worried if he had done the wrong thing. He loved Bonnibel, but she tended to overlook the nuance of a matter in favor of quantifiable facts. Walking Finn through the mechanics of sex was one thing, but would she stress the importance of being emotionally prepared and supportive of one's partner? Jake couldn't be sure.

Gloom settled over the dog. No matter how uncomfortable it was, he had a responsibility as Finn's oldest friend and de facto role model to make sure his little brother had all the tools necessary to navigate this experience safely. If he couldn't bring himself to discuss it with Finn directly, the least he could do was go and talk to Fern. Which is exactly what he resolved to do.