Woodstock man pleads guilty to attempting to force sex act on woman

A Woodstock man has pleaded guilty to attempting to force a woman to perform a sexual act; authorities alleged he attempted to stop her from leaving. Find out how much prison time he got.

A Woodstock man has pleaded guilty to attempting to force a woman to perform a sexual act and was sentenced to three years in prison. Dillon Tripamer, 27, entered a guilty plea in June to attempted criminal sexual assault, a Class 2 felony, according to the judgment order filed in McHenry County court and signed by Judge Mark Gerhardt. “Mr. Tripamer is pleased to have reached a resolution in this matter,” said Megan Kostolansky, one of the attorneys at Rotunno & Giralamo who represented him.

“Although differing views exist surrounding the circumstances that led to his arrest and charge, Mr. Tripamer’s biggest priority was putting this behind him, and returning home to his family.” Authorities had alleged in a criminal complaint that on May 27, 2025, a woman was attempting to leave Tripamer’s home but couldn’t find her keys or cellphone. When she asked Tripamer where her items were, he responded that “she needed to perform [a sex act] on him prior to leaving” and attempted to force her to do so, according to Judge Cynthia Lamb in an order denying his pretrial release at his initial court appearance, about five months later, on Oct. 31.

As the woman freed herself from his grip and ran toward the door, he blocked it, and when she attempted to run again, he “grabbed her ankle causing her to fall to the ground and causing a red mark to her ankle,” according to the complaint. He then pulled her onto the floor and attempted to remove her clothes and said, “Let’s have some fun before you go,” according to the complaint. When “the attack” stopped, there was a fight over the woman’s cellphone, authorities said.

Tripamer “grabbed [the woman] by the neck, leaving red marks, and twisted the cellphone out of her hands,” according to the complaint. Authorities said Tripamer also deleted an application from the phone that had showed security camera footage in the home. The incident occurred when a child was in the home, authorities said.

Tripamer ultimately pleaded guilty to the single felony charge for removing the woman’s pants “by the use of force ... with the intent to commit an act of sexual penetration.” In exchange for the guilty plea, two counts of domestic battery, Class A misdemeanors, were dismissed. Tripamer is required to serve half his prison time and is receiving credit for 230 days in McHenry county jail since his arrest.

Following incarceration, which under truth-in-sentencing laws will be about 10 months and two week, he will be on mandatory supervised release for one year, according to the order.