From dick + ride.
dickride (third-person singular simple present dickrides, present participle dickriding, simple past dickrode, past participle dickridden)
- (informal, transitive, vulgar) To behave in a submissive, subservient, or overflattering manner toward.
1999 April 1, Always with Wings, “Re: 2pac was better than Biggie”, in alt.rap[1] (Usenet):yeah,but look at how many people dickride rakim,nas,slick rick,krs-one,and the roots?they probably have never even heard their music........
1999 August 4, Arnold Layne, “Re: Ray Cappo on the Blair Witch Project”, in alt.music.hardcore[2] (Usenet):Go dickride every single band to ever emerge from England between the years 1987 to the present. Oh wait, you already do!
1999 November 26, OHHLA Webmaster: 'Flash', “Re: Goodbye RMHH, Hello alt.rap”, in rec.music.hip-hop[3] (Usenet):I think the problem is that a lot of people who +do+ dickride don't realize the fact they are cutting their favorite artists slack.
2003 May 19, JuiceRoc, “Re: One of the Dumbest Incidents In Hip Hop History”, in rec.music.hip-hop[4] (Usenet):you think im about materialism cause i dont dickride wu tang and i like money.
- The word alludes to having sex in the cowgirl position, with the sense that the "dickrider" is making an effort to please the other party. In a context discussing actual sex, however, a construction like "ride his dick" is much more likely than one like "dickride him."
