In this study, we investigated brain dynamics from electroencephalographic (EEG) signals during affective tactile stimulation conveyed by the dynamical contact with different fabrics. Thirty-three healthy subjects (16 females) were enrolled to interact with a haptic device able to mimic caress-like stimuli conveyed by strips of different fabrics moved back and forth at different velocities. Specifically, two velocity levels (i.e., 9.4 and 65 mm/sec) and two kinds of fabric (i.e., burlap and silk) were selected to deliver pleasant and unpleasant affective elicitations, according to subjects' self-assessment. EEG power spectra and functional connectivity were then calculated and analyzed. Experimental results, reported in terms of p-value topographic maps, demonstrated that caresses administered through unpleasant fabrics increased brain activity in the θ (4-8 Hz), α (8-14 Hz), and β (14-30 Hz) bands, whereas the use of pleasant fabrics enhanced functional connections in specific areas (e.g., frontal, occipital, and temporal cortices) depending on the oscillations frequency and caressing velocity. Furthermore, we adopted K-NN algorithms to automatically recognize the pleasantness of the haptic stimulation at a single-subject level using EEG power spectra, achieving a recognition accuracy up to 74.24%. Finally, we showed how brain oscillation power in the α and β bands over contralateral frontal- and central-cortex were the most informative features characterizing the pleasantness of a tactile stimulus on the forearm.