A Sheltered Teenager's Unfortunate Life Lesson (teen x old man)

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ValerieLeigh99

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This is just another longtime fantasy of mine which I'm going to attempt to summarize in written form. There are inevitably going to be plot holes and so I encourage questions :) realism is my goal here.

Arrangement 4: first of all I'd just like to point out that I am 100% aware that this is very similar to my 'arrangement 1' plot, but there's a good reason but I'm making a distinguishment between the two despite their similarities. I've actually lived out a watered-down version of arrangement 1, whereas this is more or less a more intense version that I don't know that I would have ever had the bravery to dabble in. Especially as a teenager, lol

Anyway, the idea here would involve an old man living nearby or even next door to a teenaged girl whose family he knows very well. Family friends for years and years perhaps? Longtime neighbors? Whatever pairing we go with, the main thing that makes this idea work is:

1.) My characters high level of trust for the old man

And....

2.) The old man's high amount of time spent with me (perhaps babysitting over the years) and knows very well just how airheaded I am

So far, this is no different than arrangement 1, but where it becomes different is where it goes from here. You would still be tricking me, and you would still be looking to exploit my naivety. You'll be much more cold-hearted about it here though.

One thing you've always noticed about me is that I'm always smiling. Like, ALWAYS, and it drives you mad. It was cute at first but lately? Well, lately it's been very annoying. It's grown into such a bother to you that you've actually smiled at the very thought of me having to be upset over something. To finally have something in my life that DOESN'T go my way. To have something that I finally have to work my way out of instead of being handed the golden ticket out of trouble. To look me in my tear-filled eyes and tell me that "hey, life's a bitch and it's just the way it is..." before I actually have endure my most humiliating moment ever. That moment? Your mind has wandered to two possibilities:

1.) Seeing the soft, youthful lips you've loved staring at, wrapped around you with tear-filled, downcast eyes, while talking down to me about how life stings and how this was bound to happen someday, even if metaphorically...

Or....

2.) Having my hands tied together while bent over the side of your bed, drilling my first anal sex right into me with so much Vaseline that any tightening is rendered useless, letting out the first cries and whimpers that you've ever heard me make - ones that show that I'm clearly experiencing the worst situation of my life.

Yeah, those explanations could both use some work. The end goal however for either choice remains the same: you want to see me walk away from this with a reason NOT to smile..... for once in my freaking life. Unfair? Yes, but life's a bitch. That was your point from the beginning. The means to achieving that goal is up for discussion. The first idea I have though, is for you to set me up to cause a problem inadvertently during one of my routine visits to your house. Maybe you arrange something in your house to break when I touch it, or maybe you feign an injury when accidentally bumping into me. Its up to you, but you'll make me work it off one way or the other. Do you scare me into either of the two ideas above? Or do you have me do tons of yard work in the hot sun after giving me the choice between that or the choices above, only to look an exhausted me in the eye and tell me "hey, not good enough... like I said, life stings sometimes..." before having me do either of the above ideas ANYWAY? Once again, just ideas.
 
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