In the last few decades, the access to the Internet has massified, becoming an essential part of the everyday life of people, providing means of communication, information, and leisure, among others. This also can be established in the case of teenagers, which, as statistics points out, are rapidly increasing in the number of users, the amount of use – intensity –, and the differences in the uses of the Internet that they do – variability –. The younger users of the Internet are the more susceptible ones to be affected by the increasing and various kinds of risks taking place online, such as “cyberbullying” and “sexting.” Despite the public opinion and the debate in mass media, the exchange of sexual messages and/or pictures has been focused on in only a few studies in the Latin American region. The present chapter will analyze the relationship among the different forms of exchanging “sexual images/messages through digital media” (“only send,” “only receive,” “receive and send,” and “‘those who do neither of the two things”) experienced by Chilean and Uruguayan adolescents. The analysis will be based on the data gathered around the Global Kids Online Survey in both countries. These are national surveys applied to children and teenagers, users of the Internet, between nine and 17 years-old, but these particular indicators are comparable between both countries only for the teenagers in the range of 13 to 17 years old. This analysis will allow us to explore on the self-reported sexual images/messages sharing behaviors mentioned above or the lack of it in the aforementioned Latin American countries, checking for the most relevant socio-demographical variables identified by the specialized literature: sex, age, access, and education of the head of the household and subjective wellbeing indicators of the teenagers that answered the survey. These results will contribute to a critical discussion on a topic that is highly mentioned on parents' concerns about children's digital experiences.