Warnings: I don't own the boys. If I did, I'd tie Sam down to a bed and have my wicked way with him. And I don't make any money.

While the underage N/C is not shown, this story is told first person by a man planning to rape a minor and it is implied at the end, so please keep that in mind and do not read if you are not comfortable with this.

Bobby's Big Brother

My name is Blaine Singer and I'm Bobby Singer's big brother. Now, Bobby and me ain't very close but, time to time, I drop by to visit. And when I do, I always hope the Winchesters are there because, you see, I've become quite fond of John and his boys. Especially his boys. And especially his youngest, Sammy.

Now I'm a patient man and by that I mean I've had my eye on young Sammy since I first met the kid a couple of years ago. Two years ago I think. Yeah, two, 'cause he was only fourteen and while that was so damn tempting - gives me a hard on thinking about it - I knew that messing around with a boy that young wasn't going to go unnoticed. See Sammy's got this older brother who don't miss much and even back then and at the age of sixteen (when I first met him), Dean was someone to be reckoned with. Especially if he thought someone was a threat to his brother and most especially if he knew what I wanted from the kid. And Sammy also has a great big pappa bear with an even bigger reputation of taking care of any threats to his family. Any. And, of course, Sammy also has my own little brother, Bobby, who'd kill to keep him safe. He'd kill even me and especially if he knew how much I loved stuffing my dick into unsuspecting teenagers. But as much as that should have put a damper on my enthusaism and might have even made a lessor man reconsider such a treasured prey. It didn't. In fact it made this conquest even more important.

And it just made me wait for two more years so Sammy'd be big enough. Wait and plan. And so now, two years later as I sit at a nice friendly family dinner with the Winchesters at Bobby's house, I can hardly keep the smile off my face because tonight, I'm going to fuck that sixteen year old boy.

I guess you're wondering why Dean didn't do it for me. Why Sammy? Well its easy enough to figure out. I'm a coward. Dean is too much of everything for me to see him as anything other than a brute, but Sammy, oh sweet, sweet Samy with his shy dimpled smile, soft babylike skin and wide, wondering eyes so full of gentleness and compassion, screamed lust right to my cock. Which is, right now, so hard I could probably cut ice with it.

But now comes the careful planning 'cause, see, I don't want to get caught, and so far everything is going the right way. Bobby and John got a hunt for tonight and, Dean, 'though he was originally supposed to hang out at home with his little brother now has a hot date. Thanks to me. Of course he doesn't know that part. He just thinks its his charm that has one of the hottest girls in the area wanting to see a movie with him. Okay, that might be part of it. But the money I'm paying her to make sure she fulfills Dean's every wish with her talented mouth and even more talented body - after all his brother is about to fulfill mine - is a bigger part. So that leaves me and Sammy. Well Sammy only because, as far as my family and his are concerned, I'm also going to be gone. I'm a busy man afterall and I'm leaving for a week, in an hour.

So everything is set. John and Bobby will leave. I'll leave. I'll watch Dean leave and then double back. Then it'll be fun time for me.

Sammy won't know what hit him. Or fucked him actually. And the best part? He won't even remember 'cause, see, I've spiked his drink. He's going to be exhausted and go to bed early. By the time I get there, he's going to be unconscious and then I'll have my fun.

I have that all the planned out as well. First, I'm going to remove all his clothings, oh man, I could shoot my load just thinking about that. Then I'm going to run my tongue and hands over every square inch of his innocence, starting with his nipples and moving down his chest to his young cock, and then suck and nip my way behind the soft furry balls and towards the prize. His cherry little ass.

Then, 'cause I'd hate to have this end too soon, I'll get him to give me a blow job first. Impossible you think, with him out cold? Nah, you just got to be more careful when you shoot your load that he doesn't choke, but I figure a boy like that is going to have wonderfully strong swallow reflex. Oh God, I think I might need to whack off even before that.

After I've come down his wonderful throat, I am going to roll him onto his front and get to prepping him for the main event. I figure he'll need at least three fingers in his ass, fucking him open before he'll even start to be ready for me. Yeah, three for sure. I might be bald and fat but I'm still well hung. That's a Singer thing. Ask Bobby.

When he's taking my fingers like he's been born to do, I'm going to take them out, lube up my rock hard cock and then drive in all the way, in one thrust. I want to feel my balls smacking his ass as I pull out and plow back in. God, I can't wait. And I know, from experiences that Bobby will never know about, that I'll be able to last about twenty minutes, regardless of how tight Sam is, before I'm ready to blow my load.

Then, once I'm done, and depending on the time, I might start all over again.

Doesn't that sound wonderful to you? I'd invite you in to help me fuck this beautiful boy, but I really don't like to share even with women. And if everything goes off like I'm planning, I should be able to do this again the next time we're all at my brothers. Of course that will depend. Maybe I won't be interested in fucking him after I've filled his bowels with my spunk. Ha! Ha! Who am I kidding? I'll be lucky if I can ever find another boy as good as him to satisfy me in between.

Ooh and the final piece? The one that I'm going to use to masterbate with afterwards? My souvenir? Well, once I finish fucking the kid and I re-dress him 'cause I don't want anyone to know what I've done, I'm going to keep his underwear. Can you imagine his shock when he wakes up in the morning, his ass burning and his underwear missing? I just wish I could be there to see it.

I'm betting he's never going to tell...

Well I gotta go now, Sammy is just finishing the last of his drugged drink and I'm supposed to be leaving. It's been nice talking to you and hey, maybe next time I'll set it up so I can invite you in on this. Or rather, in on Sammy.

_________________________

When sixteen year old Sam Winchester woke up the next morning he realized two things right away:

The first was that his ass was hurting. Burning bad. And the second was that he wasn't wearing underwear.

The End.