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first monkey in space

Trying or experimenting with something new - on a grand scale with high risks and potential for epic failure or even disaster.
Live streaming my rockclimbing trip is gonna be like the first monkey in space for me.”

A pygmy marmosets's interlude is a Proboscis monkey: The First Juvenile Release

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Person 343: A pygmy marmosets's interlude is a Proboscis monkey: The First Juvenile Release

A pygmy marmosets's interlude is a Proboscis monkey: The First Juvenile Release (Human). 

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A pygmy marmosets's interlude is a Proboscis monkey: The First Juvenile Release (Human).

Awkward Monkey Fist

When one clutches their hand into a loose fist as if holding a rolled up piece of paper, and shakes it back and forth in front of someone's crotch. This will make the person feel very awkward, at which point you will have to explain your actions to them in the following way. "See. . . a monkey is jacking you off . .. thats why its awkward!"
So I was hanging out the other day, and my best friend awkward monkey fisted me. . .

Velvet Monkey Fist 

When a guy is butt fucking his girl while she is laying on her back. At this time he inserts his hand into the woman's vagina and wraps the thin membrane between the anal and vaginal canals around his cock. This enables him to jack himself off while fisting his mate at the same time.
Oscar loves giving Christina the Velvet Monkey Fist since he loves anal and she loves fisting.
Velvet Monkey Fist by Dadda February 14, 2008

Monkey Fist 

When a man defecates in his hand, then squeezes it so that the feces leaks out from between the fingers, and thrusts it into the vagina or ass of his partner.
Bill: Hey, John, have you met my new girlfriend?
John: I hate to tell you this, dude, but I used to totally monkey fist her.
Bill: That's disgusting. And kinky.
Monkey Fist by E. Barrett March 7, 2008