Paul O’Neill, 57, organised sex shows by speaking to women online and requesting performances involving young girls.
The Crown Prosecution Service said the virtual rape case was thought to be the first of its kind.
O’Neill, of Wollaston Vale, Nottingham, pleaded guilty to 30 charges of procuring children as young as four for sex acts, including rape.
He was jailed for life at Nottingham Crown Court with a minimum sentence of 12 years.
O'Neill used chat logs and paid over £6,000 for several years to satisfy his “fetishes” with child abuse, virginity and incest.
Judge Gregory Dickinson told him: “In plain English, you are a danger to children.
“Given the chance, you will offend again. You are obsessed with and addicted to the most vile and horrific abuse.
“It should reduce any compassionate human being to tears.
“You demanded that these little children should suffer pain and degradation.
“You wanted to see children - very young girls. You paid for the most extensive sexual abuse.”
Some of the victims were from families desperate for cash for medicine and hospital bills, the court heard.
On one occasion, he offered to double his payment if the victim was aged five.
O'Neill retired last August after working at The Becket School in West Bridgford, Notts, for 25 years.
Prosecutor James Varley told the court: “Mr O’ Neill, a retired teacher, a bastion of the local church community and a Sunday school teacher, appeared to a wholesome married father of two.
“In fact, he had a dark side to him which he kept concealed – he was obsessed with the the sexual exploitation of pre-pubescent girls… and enjoyed the sexual abuse and degradation of young girls."
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