Trailing rhymes with:
derailing, grayling, railing, ailing, assailing, ayling, bailing, baling, curtailing, derailing, detailing, emailing, entailing, failing, flailing, grayling, hailing, impaling, inhaling, jailing, mailing, nailing, prevailing, railing, regaling, sailing, saling, scaling, surveilling, tailing, unavailing, unfailing, unveiling, veiling, wailing, whaling
Trailing sounds like:
thrilling, trilling, trillions, trolling, twirling