This one probably crosses the line. I could not think of a title that could possibly sum up the content in this video. It goes from v*rgin humiliation, to cuckolding, to fantasy, to bi, and back through the list all over again.

In this story, you're a v*rgin in school with his very first girlfriend. You've barely even kissed yet. As you stroll down the hall holding hands, your most-feared bully shows up with his two punk friends. He's t*rmented you all throughout your entire school career, and he gets a sadistic pleasure out of making your life a true hell.

He begins to humiliate you in the most degrading, filthy, horrific ways possible: through your l*ttle girlfriend. While his l*ttle friends watch out for anyone who might interrupt, he begins to fondle your girlfriend as she is pressed up against you, with you flat against the wall. He touches her in places you've never even seen. Eventually, reluctantly, she starts to moan and whimper. Her p*ssy juices soak your pants...and even you get the beginnings of a hard-on, because you're a v*rgin in school and your girlfriend is practically cumming right on you - because another guy is sexually dominating her on top of you. He, also being a boy, is so aroused by the imposed fingering, that he can't contain his erection and is now determined to f*ck her. Right on top of you, in the middle of the hallway, looking you straight in the eyes as he enters her. Her mouth opens in a gasp and she nearly goes cross-eyed. His huge c*ck penetrates her v*rgin p*ssy and, after some initial p*in, her wetness allows him to pump in and out of her with ease. You can hear the wet sl*shing noises and feel the pulse of her hips grinding against you with every thrust. He's basically f*cking you both, regardless of whether you say no.

The story ends in the most painful cuckolding way: Since she can't even look at you anymore, she dumps you and you have to see her every day and be filled with shame and confusion. Then, the ultimate slap in the face: She starts to date your bully. You have to watch them dirty dancing at the prom. She was never that way with you. Ever. But there she is, grinding her body against his and making out right in front of you.

Prepare your tissues, boys, because this one will make you cry AND c*m.

A Very F*cked Up Story - WMV HD