My last job was a haven for innuendo and wrongness,
whether unintentional or otherwise. At one point I was having a conversation about food with Kelly, who was a vegetarian, and I told her "I think you ought to get back on the meat" to the amusement of many.

The best, however, occured when we having one of our frequent sessions were we posed each other 'would you rather'/moral dilemma type questions rather than doing any proper work.

I gave Kelly a complex one, involving her and her sister being locked in chambers, which would be flooded with lethal nerve gas in exactly one minute. Each chamber, however, contained a button that, if pressed, would gas the chamber of the person who pressed it, but open the door of the other one.
The question being, would she sacrifice herself to save her sister, or gamble on her sister pressing the button? Kelly decided she'd need to ponder that one for a bit and we got back to work.

About five minutes later, another colleague (who hadn't heard the earlier bit) was walking back to his desk just in time to hear;

Me: So, you've still not answered my question.
Kelly: Ahh, wait 30 seconds, then push my button.

The expression on his face, and his choking gasp of "What?!" were priceless, and after I finished laughing I explained to him that the context was that of a twisted Saw-esque mind game, rather than some form of clumsy office seduction.

These are but two examples of the many innuendos that occured. They are though the only accidental ones I can think of. We truly were some filthy minded people.

I'm not even going to try and make a length joke in this qotw.
(Uncle Comrade, Tue 17 Jun 2008, 1:09, Reply)