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1.
Barstooling is a verb and involves visiting several bars and sitting directly at the bar for at least one or two cocktails. This is similar to a Pub Crawl, except barstooling usually involves mostly dive bars and can involve fewer people. Barstooling is best started during daylight hours and can progress for as long as one can remain stable on the barstool. Barstooling usually ends when someone falls off the barstool.
K-hot and I went barstooling in the afternoon and we got hammered.
by Nightraider November 05, 2007
 
2.
Barstooling is when three men or more penetrate a woman at the same time anal,vaginal, and oral. Occasionally multiple peni in the same orifice,When performing this act the individuals resemble a barstool i.e. The peni are the legs and the woman is the seat.
My homies and me picked up this skank and proceeded to barstool that trick. My crew an me ended up barstooling that ho at the motel.
by Mr. Bigg574 August 15, 2013