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ROTW 4 - Chatroulette Puppet on Tits, D...

ROTW 4 - Chatroulette Puppet on Tits, Dicks, Gays, and Marriage from rupertontheweb
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ROTW 4 - Chatroulette Puppet on Tits, Dicks, Gays, and Marriage from In this special episode of Rupert on the Web, Rupert meets the woman of his dreams, only to be thwarted by his inability to present her with an engagement ring! He also meets so...
Time: 5:46   |   Views: 692   |   Rating: 58% Funny

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Rupert on the Web - Chatroulette 3: Sho...

Rupert on the Web - Chatroulette 3: Show Me Your Boobies from rupertontheweb
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Rupert on the Web - Chatroulette 3: Show Me Your Boobies from Rupert's latest adventure on chatroulette, sees him meed a Danish 'odd couple', tries his hand a rapping, and when he finally meets a woman on chatroulette, he seems incapable o...
Time: 3:11   |   Views: 1,533   |   Rating: 66% Funny

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Rupert on the Web Chatroulette 2

Rupert on the Web Chatroulette 2 from rupertontheweb
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Rupert on the Web Chatroulette 2 from Rupert has another go on the famous chatroulette. This time he meets a disappointing superman, an attractive blonde lady, and inadvertently makes an enemy when he wakes someone up!
Time: 4:00   |   Views: 175   |   Rating: 100% Funny

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Rupert on the Web - Chatroulette 01

Rupert on the Web - Chatroulette 01 from rupertontheweb
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Rupert on the Web - Chatroulette 01 from Rupert having his first go on chatroulette, and thoroughly enjoying himself. In this episode, he encounters a frenchman, a brief pair of enjoyable boobies, and a young group of ...
Time: 3:52   |   Views: 108   |   Rating: 86% Funny