A common sexual gratification method used in the mainstream hip-hop community. To "get one's swoll on" is to paint around one's anus with dark red lipstick, making it resemble a vagina. The rapper will then visit a gynecologist and request a full vaginal exam, presenting his painted anus as the vagina. The sexual gratification is achieved later that day while masturbating and thinking about how the gynecologist was so easily duped. It is widely believed that this practice within the hip-hop community was started by T-Pain (Tushie-Pain). ORIGIN: the swollen condition of the anal opening after being prodded by the gloved hands and speculum of a seasoned gynecologist.
"shit just don't feel right but im gonna hold on
till the hole in my 44 long
im gonna hit the ob-gyn and get my swoll on
sometimes my head gone"
-drag on, "life is short (so you might as well get your swoll on as much as possible)"