Sex in Waukesha County Jail lobby, woman sentenced – to jail

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Karen Hill

WAUKESHA, Wis. - A woman who prosecutors said had sex in the Waukesha County Jail lobby pleaded no contest and was sentenced to jail time on Monday.  

Jail time

In Court:

Karen Hill, 68, pleaded no contest to misdemeanor disorderly conduct. Court records show she was sentenced to 90 days in the Waukesha County Jail with credit for 34 days served. 

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Hill was later accused of having sex at a Waukesha laundromat with the same man. That case was dismissed and read in during sentencing for the jail lobby sex case.

Desmound Cleveland, the man with whom prosecutors said Hill was involved in both the jail lobby and laundromat sex cases, was previously sentenced to 60 days in jail for disorderly conduct in the laundromat sex case. He was sentenced to time served for the jail lobby case.

Desmound Cleveland

Sex in jail lobby

The backstory:

According to a criminal complaint, a sheriff's deputy was called to the jail lobby on May 2, 2024. The jail supervisor "called to report two individuals had sex in the jail lobby" and Hill was still on the scene.

The deputy was able to get video surveillance of the incident, which happened around 3 a.m. It showed two people in the lobby "engaged in sexual acts," per the complaint.

The complaint states the deputy contacted Hill. She said Cleveland was her boyfriend, and they intended to hang out at a boarding house, but they got locked out. They then walked to the jail lobby and took a nap. 

Hill admitted she and Cleveland "had sexual intercourse and that it was consensual," the complaint said. She added that "she tried to cover both of them up with articles of clothing so no one would see them."

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When the deputy questioned Cleveland about what happened, the complaint states he said: "Sex happens." He also said he knew there were cameras.

Laundromat sex

What they're saying:

Police were called to a laundromat near Hartwell and Broadway on Dec. 24, 2024. According to a criminal complaint, the owner said he was watching security video and saw two people "engaging in sexual intercourse" under a blanket "in full view of the camera."

Couple accused of having sex at Waukesha laundromat

At one point in the video, prosecutors said the blanket slipped and both Cleveland and Hill could be seen with their pants down. An unsuspecting patron was sitting "not far" from them the entire time.

An employee yelled at the two to get out and apologized to the other customers, per the complaint.

Cleveland was arrested on Jan. 5, 2025. Court filings said he admitted to being at the laundromat with Hill "some time in December" and said they were "touching" each other while waiting on their clothes. However, per the complaint, at no time did video show the two cleaning clothes at the laundromat.