10 Sex Toys With Ridiculously Ancient Origins PHOTO Roman era 'wooden phallus' found: Is this the oldest sex toy? Free press The oldest dildo in the world is approximately 28,000 years old. It was discovered in 2005 in Tbingen, Germany by archaeological researchers at the university there. It is eight inches long and " The Evolution of Sex Toys The Pleasure Chest The long and satisfying 28,000 year history of the dildo The Surprising History of Dildos: Humans Have Been Using Them for Over 28,000 Years