It would make a lot of sense if the conditions for receiving the LOL-TM would be the same as those for getting the E-Peen. I’m jumping on the “definite bug” bandwagon here. Since I did not experience this issue myself, I’m not in a position to file a proper report, but I would suggest you do if you got the TM but no Peen.

Edit: Now that I see there are two versions of the LOLcat TM where one fits the old description of the Peen way better than the other I need to revise this. If you got the short LOLcat TM you got the Peen, if you talked WIM into therapy in addition to sending him LOLcats you get a longer TM, a flezz reward, but no E-Peen. It makes sense that this is intended behaviour.