Two men, not necessarily homosexual who flip flop during sexual intercourse with each other.
When Kevin and Eric sleep together, they always go caboose caboose.
by Elusive Reclusuve June 14, 2017
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The brother of the girl you with.
Hey Hainer, is your brother the douche caboose coming with us?
by Ajudichop April 25, 2021
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The act of contributing to a Tennessee Train Track, and getting stuck with the last position of the chain.
“How did your Thursday go last week?”

“Man, it was crazy, the only problem was that I was the Colorado Caboose of the train, now my teeth are all soggy.”
by Homosexual_Badger April 18, 2023
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We went out and ran a jtrain on t-caboose last night.
by chicken! February 11, 2008
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People who type part of a sentence, send the message, and then finish it in another message (applies to online chat rooms or messaging programs)
Tom: No homo
Jim: Yes
Jim: It's totally homo
Tom: No
Tom: You're just jealous
Tom: My purple orange isn't homo
Jim: Kakagawa, you have Caboose Syndrome.
by Skull Tooth April 14, 2010
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