Drama learning is helpful for English speaking, however, few studies provided students with opportunities to practice drama conversations individually. This study proposed a Context-Awareness Smart Learning Mechanism (CASLM) and integrated into SmartVpen that consisted of context-aware learning content, context-aware input assistance, oral recognition feedback, peer cooperative learning, and smart conversation robot. The participants were 68 eighth grade-students divided into three groups: an experimental group (EG) who used SmartVpen, a control group 1 (CG1) who used typical camera and voice recorder, and a control group 2 (CG2) who used papers and pencils. The results showed the EG outperformed the other groups concerning oral and conversational skills, which indicated the use of SmartVpen had significant effects in both English oral speaking and conversational skills. Additionally, the number of time to complete conversation practices can predict students' oral performance by 30%. Furthermore, the results also showed the EG tend to practice drama conversations more frequently than the CG1, which demonstrated practicing English drama conversations using SmartVpen can effectively improve students' learning motivation. Thus, we suggested English conversations practice activities should be conducted in authentic context with SmartVpen to support students' speaking and facilitate them to apply what they learned in real-life situations.