Rupert on the Web
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Chatroulette Puppet Rupert 10
Rupertontheweb
6,099 views
Rupert's 10th escapade on chatroulette, and on this journey he meets a welsh Justin Bieber lookalike, a suspected ghost, and a man who's leg turns out to be the least of Ru...
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Imrpov Chatroulette Puppet searches for Boobies (Rupert 9)
Rupertontheweb
1,403 views
After a brief break from broadcasting, Rupert's back and he's on a mission: To see his first pair of chatroulette boobies. It may take time, but he's prepared to work at ...
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Rupert - Chatroulette Puppet 8 - Rudeness, and Jason Biggs
Rupertontheweb
2,992 views
Rupert's latest video shows him giving back some of the rudeness he's witnessed on chatroulette. He masturbates a little, and even does a swear! Don't be watching if you'...
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Chatroulette Puppet Rupert on the Web 7 - Taking on Racism
Rupertontheweb
1,531 views
In this episode, Rupert quizzes a man about how to find boobies, but did he pick the right man to take advice from? He also meets an Australian young lady who wants to hea...
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Funny Chatroulette Puppet - Rupert 6
Rupertontheweb
1,451 views
Rupert's latest journey into the weird and wonderful world of random chattery, saw him meet 'Gollum', a man so taken with his dreadful teeth, that he seemed incapable of ch...
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Rupert the Chatroulette Puppet 5 - Jesus gets high!
Rupertontheweb
2,154 views
In this episode, Rupert meets Jesus (or a man who looks like him), some 'willy wobblers', and also a Marine, whom Rupert mistakes for a prisoner in jail!
If you like Ruper...
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Rupert on the Web - Chatroulette 4 - Tits, Dicks and Gays
Rupertontheweb
3,731 views
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 me...
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Rupert on the Web - Chatroulette 3: Show Me Your Boobies
Rupertontheweb
19,732 views
Rupert's latest adventure on chatroulette, sees him meet a Danish 'odd couple', try his hand a rapping, and when he finally meets a woman on chatroulette, he seems incapabl...
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Rupert on the Web Chatroulette 2
Rupertontheweb
3,974 views
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 so...
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Rupert on the Web - Chatroulette 01
Rupertontheweb
3,992 views
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 gro...
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