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Robert Oakley exposed himself to two women out walking their dogs on separate occasions, a court heard.
The 51-year-old, of Lyons Street, Southampton, followed his victims before pleasuring himself in front of them in Frog Lane, Fordingbridge.
Both were left “badly frightened”.
Oakley still denies two charges of indecent exposure he was accused of, however, following a three day trial at Southampton Crown Court, he was found guilty.
Prosecuting, Siobhan Linsley said the offences were aggravated by his antecedence.
Defending, Gaylene Coles said that her client had suffered a number of traumatic events as a child.
She mentioned that he had issues with alcoholism in the past.
During sentencing, Judge Gary Burrell QC said that Oakley “seemed quite belligerent and arrogant” during his trial.
He said: “This sort of offence can sometimes lead to contact offences.
“You badly frightened both of these women. One was quite robust about it but the other was clearly frightened and scared by your behaviour. She was upset.”
He added: “You have exposed yourself to women before, but these offences are still aggravating factors.
“They were alone and where no one was around, and they were therefore vulnerable.”
For the offences which happened on January 25 and 28 last year, he was jailed for six months and made the subject of a five-year restraining order against one of his victims.
He must sign on as a sex offender for seven years.
Commenting on an earlier occasion, PC Sarah Taylor said: “We would like to thank those women who came forward and told us what happened to them. Being subjected to something like this can be very distressing and shocking, sometimes leaving a victim unsure of what to do or how to report this kind of thing to us. We absolutely want to receive your call and bring offenders like Oakley to justice. If it’s happening now, always call 999. These incidents rightly concerned the community in Fordingbridge at the time and we’re pleased to be able to say now that we were able to put a stop to this, with the community’s help.”