Possible electron pairing in pi-conjugated positively charged annulenes such as (CH)(18) (18an) and (CH)(30) (30an) is studied and compared with that in the positively charged acenes. The total electron-phonon coupling constants in the monocations (l(HOMO)) for 18an and 30an are estimated. The E-2g modes of 1611 and 1201 cm(-1) most strongly couple to the highest occupied molecular orbitals (HOMO) in 18an and 30an, respectively. The lHOMO values for annulenes are larger than those for acenes. The phase pattern difference between the HOMO of acenes localized on the edge part of carbon atoms and the delocalized HOMO of annulenes is the main reason for the calculated results. In view of the calculated results of the lHOMO values, intramolecular electron mobility (sigma(intra), (HOMO)), and the reorganization energies (REHOMO) in the positively charged molecules, the monocations of annulenes cannot easily become good conductors compared with the monocations of acenes, but the condition of the attractive electron-electron interactions is realized more easily in the monocations of annulenes than in the monocations of acenes. The hypothetical intramolecular supercurrent originating from both intramolecular and intermolecular vibrations in the monocations of annulenes and acenes in a case where the distance between two adjacent molecules is too large for the molecular crystal to become normal metallic state, is also discussed.