This chapter explores how sexual identity and sexting behaviours are shaped by cultural, historical, and social influences, drawing on the theory that sexuality is not fixed but constructed through societal discourse. Sexting, particularly among adolescents, reflects these evolving norms. Data shows that boys who engage in active sexting, especially those doing so occasionally or frequently, tend to use self-generated images and videos, often shared via social media. Being in a relationship significantly increases the likelihood of sexting, though other factors such as the number of relationships, religious beliefs, ethnicity, sexual orientation, and school type. For some, particularly within the gay community, sexting may serve as a means of identity expression and social belonging, outweighing potential legal or social risks. The findings suggest that sexting is not merely a personal act, but a socially embedded practice shaped by the need for connection, identity affirmation, and cultural expectations.