Well, this is not what I thought the first DR doujin posted to this site would be. Who even ships this anyway?
It's semi-official, assuming canon isn't quite the right word for it.
In Ultra Despair Girls, Kotoko captures Komaru and straps her to a fondling machine. If you fail a subsequent minigame, Komaru gets mind-broken and lilies flood the Game Over screen.
The BDSM machine happened, and I'd rather forget about it, but the actual ship/scenario for this doujin is nowhere near 'official'.