An increasingly relevant wordplay on the cliché "cautiously optimistic". As the world continues in free fall, its much more realistic to expect negative outcomes. Therefore, its much more pragmatic to maintain a cautiously pessimistic demeanor, rather than a cautiously optimistic one.
My cat is always cautiously pessimistic when inspecting anything new that I bring into the house.
When one has two pussies stacked one atop the other, for easy alternating insertion. Usually done doggystyle, this position is used mostly in FFM (female-female-male) porn.
Did you see Ava Devine and Alica Saint in that new Peter North flick? He stacked their asses up into double decker pussies and fucked them both, man!
Easily the most negative person in a group of people that are otherwise having a great time. But instead of keeping it to himself, it becomes his mission the fuck the fun up for anybody that looks too happy.
BRO 1: Hey I got these four girls to come back to chill with us at the house!
BRO 2: these girls don't like you bro, they're just gonna smoke your shit up, drink the liquor and leave. I bet at least two of them have the herp, either way this shit is weak don't bring them over I got shit to do at noon tomorrow.
BRO 1: never fails always such a fucking pessimistic pete..