From dick ride
dickride (third-person singular simple present dickrides present participle dickriding simple past dickrode past participle dickridden
( informal , transitive , vulgar ) 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."