Robert Jenner, who claims to be a naturist, also strolled around a shopping centre wearing see-through trousers.
The 43-year-old showed off his privates to a teen schoolgirl and pregnant woman while working as a self-employed courier for parcel firm Hermes.
He dropped off parcels in crotchless jeans during a ten month flashing campaign in Kent and exposed himself to day trippers at a park.
Jenner was today caged for two years at Canterbury Crown Court after being convicted of ten counts of exposure.
The former soldier was also made subject to a bizarre Criminal Behaviour Order for seven years – forcing him to wear at least one layer of clothing that hides his manhood.
EXPOSED HIS PACKAGE
Judge Simon James told Jenner he was in reality "an exhibitionist who revels in upsetting people" with "entrenched anti-social views" about naturism.
Jurors heard Jenner was sacked by Hermes after bosses received complaints of him flashing.
The 14-year-old girl who saw his privates as she passed him in an alleyway in February last year was left feeling "uncomfortable".
She said: "He had his penis out of his trousers. It was coming out through a hole. I looked away."
Jenner repeatedly flouted his bail conditions by wearing see-through underwear in the lead-up to his trial.
He has previously been hauled before the courts for mixing cement in his front garden while completely starkers.
Jenner admitted that he loves being naked while doing up his house and is proud of his buff body – but he does worry about splinters.
Prosecutor Daniel Stevenson said Jenner sometimes wore see-through tights or shorts at a supermarket, shopping centre and near a children's play area.
He said: "He claims to be a naturist and has stood trial in the past and found not guilty of similar offences, which relate to him acting as a naked and claiming the right to be naked in public.
"The prosecution say it was his aim is that the deliberate exposure of his penis has nothing at all to do with naturism and the only explanation is that he was acting in a deliberately provocative manner with the full intention of causing as much alarm and distress as possible."
Jenner, of Snodland, Kent, was forced to sign the Sex Offenders' List for ten years following today's hearing.
Judge James said: "Over an extended period you have been deliberately exposing your genitals to unsuspecting members of the public.
"Those you have approached, although not exclusively, were young women who described their shock, upset and distress.
"These offences have been the culmination of a pattern of similar conduct and you have admitted that you have acted similarly on literally hundreds of other occasions."
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