Previous research on commercial sex has described fluidity between different forms of relationships, whereby commercial sexual relationships can be both long-term and viewed as intimate from the buyer's perspective. This article explores the construction of intimacy in long-term commercial relationships. More specifically, it examines the meaning of transactions in long-term paid sexual relationships in Sweden. Interviews were conducted with 23 Swedish men with experience purchasing sex as 'regulars'. An inductive thematic analysis was conducted. Findings show that the emotional experience is a key focus for these men when they purchase sex. The emotions involved are not delimited in time and space but are experienced both within and outside of the actual sexual encounter. Such emotions can be understood as the very precondition for the experiences of intimacy, while at the same time they create difficulties for the men who purchase sex. Experiences of intimacy are experienced in the ambiguity between unbounded and bounded authenticity and by not drawing a clear line between emotional subjectivity and consumer subjectivity.