Gain Bobby's loyalty

The first course of action is clear. Bobby looks like he'll take the side of the first person who comes along and tells him what to do... provided he trusts them.

You arrange for Bobby and you to share a room in the Black Apartments. You are not sure how to gain his trust that first night.. but something give you an idea when he starts getting upset when the lights go out.

"Hey... Brad.."
Bobby says to you.

"Whats up.. you ok, bud?"
You reply.

"No man... this creeps me out, ok? This is the first time I've been alone on my own away from home... and I know no one here... and I'm honestly scared... jeez this place is scary."
He almost seems to cry.

"What? I mean the room is a little dark, ok... and we are on an island full of strangers... but I mean, you'll be fine. Just relax a little."

"Relax how, Bard.. how?"
Bobby almost pouts...

"Well, just wack off... I won't mind... just be quiet about it."

Bobby seems ashamed to speak...
"... wack off? Whats that?"

Bobby must have been home schooled.
"Ok... well, you must have been sheltered your whole life... wacking off means masturbation... jacking off?"

Bobby stops for a bit.
"I dont know how...my parents told me I'd go to hell if I did."

You laugh a bit.
"That gives me the first idea for our party. We will be pro-wacking. Non-religious, I guess. I know how to do it quite well, and I'm not in hell, am I?"

Bobby laughs.
"This might be hell!"

You laugh a bit, and reply,
"Well, yeah, but then you are here for no reason at all, so you might as well join in in the sin."

Bobby chuckles.
"I guess so.. but how do I... wack?"

"Just pull out your dick and stroke, man"
You reply, a bit perturbed.

"Ok..."
You hear him move around abit, but nothing really comes of it.
"This is not working... and is stupid."

"You're doing it wrong then. I'm not going to help you out if you cant do this..."
You try to fall back asleep.

Bobby throws his pillow at you.
"Just show me how.. ok?"

You groan and get out of bed.
"If I do, you owe me, ok?"

He nods and you walk over to his bed and sit down. YOu turn on his bed lamp and notice that he's still got his undies on.
"Listen, those need to come off first."

He sheepishly takes his pants off, as you take yours off. He's got a bit smaller dick than your own, but at 18 you figure you both have growing to do. Besides, your are both fairly thin, and probably will put on a bit of weight yet.

You think of the hottest porn scene you've seen before, and your dick gets hard. You spit in your hand and start jerking off. Bobby tries to follow, but his dick does not get hard. Seeing Bobby staring at you jerking off makes you harder, but soon you realize he's not getting it.

Your pants are all the way off, and his are just below his junk. You stand up and pull off his pants all the way. He's not sure how to take this... but its clear that taking his shorts off woke his dick up. You shrug and realize that you'd have to get dirty at some point. You kneel before him and start jerking his dick off.

Bobby nearly screams before he catches himself.
"Holy shit that feels great... don't stop."
His hand hits the wall. "Don't stop Brad... fuck!"

"Calm down Bobby, others will hear us... just relax and enjoy."

But he doesn't relax, and soon you have cum all over your arm. You clean it off on one of his towels nearby, and you climb back into bed without a word.

"Uhm, thanks, Brad..."

You wait for Bobby to fall asleep, and then jerk yourself off.