The man, who is in his 40s but cannot be named because it would identify the victim, filmed the attacks between January 2014 and August 2025.
He pleaded guilty to 32 charges, including 12 counts of rape, 14 counts of assault by penetration and six counts of sexual assault, at Northampton Crown Court.
Ten of the offences, including four rapes, four counts of assault by penetration and two sexual assaults, were committed with other unknown offenders.
All of the offences were recorded on his devices, including one rape where a snoring sound can be heard on the video.
Prosecutor Alexandra Felix KC said: “The prosecution maintain that all of the offences were committed while the victim had been drugged and stupefied.”
But the court heard the man may argue that she was sleeping during some of the attacks.
He stood in the dock, scrunching up his face as he entered his pleas, then after admitting the 14th charge asked the judge: “Can I have one moment please?”
He then sat down with his head in his hands and broke down in tears, staying seated for the rest of his arraignment, as he sobbed and wiped tears from his eyes.
Judge David Herbert KC told him he faces a “substantial” prison sentence, which could include a life sentence or an extended sentence, when he is sentenced on 18 September.
