A court heard Wilson identified vulnerable women, including several from the city and East Devon who cannot be named for legal reasons, who he then intimidated and abused over the internet and by phone.
Wilson had met and had brief flings with some of the five women and when they split up he poured "venom into their wounds" said a judge.
Wilson started a two-year jail term yesterday after he admitted one charge of harassment and four counts of sending grossly offensive, obscene, indecent or menacing messages.
Prosecutor Ann Hampshire submitted a report to Exeter Crown Court which said Wilson "desired to have sex with the women" and felt jealous and possessive towards them, and that turned to "nastiness".
David Evans, in mitigation, said: "He went on the website, Plenty of Fish, searching for love and a relationship but found the reality fell far short of the picture he allowed himself to paint in his mind."
Wilson, from Winkebury, Hampshire, pestered the women and then "put them in fear" by making vile comments about "raping them, hoping their children would die" and describing the women using offensive terms. He asked a young victim if she had a "high sex drive" and whether she "liked a lot of sex". When she rejected his advances, he used a racially offensive term to describe her. The victim was in court and was in tears as she gave evidence.
He also abused another woman when their "fling" came to an end, threatening to "stab her" and "rape her" which left her extremely frightened.
Mrs Hampshire said all the victims were members of the Plenty of Fish dating website and Wilson used different usernames to dish out "appalling abuse".
Judge Stephen Wildblood QC jailed Wilson and also made a Sexual Offences Prevention Order and Restraining Order for an unlimited period.
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