James Frost attacked a woman he had just met at his home address in Kursaal Way, Southend in the early hours of 27 March this year.
The woman was eventually able to fight him off and escape from the address.
Then, on 30 March, Frost forced his way into an address in Southend and sexually assaulted the woman inside.
Again, the woman was able to fight him off.
Two officers went to his address later that day and the 39 year-old Frost assaulted them as they attempted to restrain him.
He was later charged and on 10 June he admitted one count of rape, one count of assault by penetration, and two counts of assaulting an emergency worker.
At Basildon Crown Court on Tuesday 3 November he was jailed for a total of 11 years and told he will spend a further five on extended licence.
Investigating officer PC Caroline Thrower, said: “James Frost subjected two women he did not know to horrific ordeals.
“He is clearly a dangerous offender and Essex is a safer place with him behind bars.
“I want to praise the bravery of the two women he attacked and their courage throughout this investigation.
“I hope knowing he will spend a significant time in prison will help them to move forward.”