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What started with a picture of Weiner's junk bulging in his undies led to several self-portraits, including one of his erect penis. This immediately raises the question: if he sends these photos to women he has never met, what does he send to women he is dating? If only for the fact that Stipe doesn't seem to be trying to impress anyone, the video and the pictures are kind of interesting. His naked photo first appeared briefly on TheDirty. Chanchez freely admits that the grainy photos are of him but he obviously did not take the pictures or send them to someone as an attempt at seduction. Weinergate started when the Congressman sent a sext message to a year-old woman via twitter. The penis picture had no other body parts visible, which makes it difficult to identify.

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Journey. Age: 25.
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The penis picture had no other body parts visible, which makes it difficult to identify.

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Briar. Age: 25.
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Chris Brown: Yes, That Is a Picture of My Dick

A few celebrity bloggers thought the penis picture would hurt Brown's career. These pictures were not just ranked 1 because they ended a political career, but because they were accompanied by transcripts of Weiner's sext messages. Much like penis pics, it is impossible to send sext messages that are not ridiculous when taken out of context. Justin Timberlake : The leaked photos attributed to Timberlake have never been confirmed as belonging to him.

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