I showed this to my son and his eyes immediately rolled so far back in his head we had to visit an ophthalmologist to correct them.
Pegging is anal penetration via strap-on
"Sliding into your DMs (direct messages)" is a term meaning "to message someone" usually with the implication of flirtatiousness or the like.
A Dungeon Master, one who runs a game of Dungeons and Dragons, is often called a DM.
Thus 'sliding into your DMs' also fits pegging a dungeon master.