Sexual activity online may result in positive experiences for young people, or lead them to engage in risky behaviours possibly resulting in sexual assault or abuse. The aim of our study was to investigate associations between online sexual behaviours among Swedish youth and background factors as well as aspects of well-being. The behaviours investigated were: having sex online with a contact met online, having sex with an online contact offline, posting sexual pictures online, and selling sex online. We used data from a representative sample of 3,432 Swedish youth who were asked about their lifetime experiences as well as their experiences within the previous year. We hypothesized that more advanced online sexual behaviours were associated with more problematic background factors, worse psychosocial well-being and riskier behaviours in general. Bivariate relationships were evaluated followed by a multiple logistic regression model. Our data suggested that most Swedish youth do not perform any of the assessed online sexual behaviours. Young people who reported online sexual behaviour showed a more problematic background, rated their health as poorer, had a more sexualized life and had experienced more sexual or physical abuse. Professionals who work with young people need to help them better evaluate potential risks online and offer support when needed. Youths who sell sex online are especially at risk and need extra attention, as they might be in greater need of protection and therapeutic support.