Easier with Practice (2009)

Davy is a 28-year-old writer on a road trip to promote his unpublished collection of short stories. A random phone call in Davy's motel room from a mysterious, sexy woman named Nicole leads to a series of phone sex sessions that surprisingly over time become emotionally and sexually satisfying for the shy writer. Later, when he meets a former girlfriend, he must try to choose between them - but only if he can arrange a meeting with his reclusive phone mate.

Source: TMDb