Army Staff Sgt. Timothy Ray Oliver II an information technology specialist at the Joint Communications Support Element on MacDill Air Force Base, was seeking a “no-strings-attached” sexual relationship when investigators say he posted an ad on online classified service Craigslist.
But instead of finding an adult, he conversed with what he thought was a teenage girl and was arrested on a federal enticement charge this month by Air Force investigators after they set up a sting.
A spokesman for MacDill Air Force Base said the investigation is ongoing.
Oliver’s troubles began Oct. 20 when he posted in the “casual encounters” section, according to a federal criminal complaint, and stated that Oliver sought “any age, size or race ...”
Ten days later, he received a response from someone claiming to be a 15-year-old girl.
But it was really an undercover investigator with the Air Force Office of Special Investigations.
In several ensuing email exchanges, Oliver tried to ascertain the purported teen’s age, solicited a picture from her and engaged in sexually explicit dialogue. He also told her that he worked for “The United States Army in Communications,” and sent several pictures of himself, including one with no shirt. Then he tried to arrange a surreptitious meeting without her mother’s knowledge.
On Nov. 2, Oliver, a decorated soldier who served in Iraq among other foreign assignments and was now working at a unit tasked with providing advanced communications systems for the military, asked the “child” for a topless photo, according to the complaint.
He also expressed concern about entrapment.
“I’d love nothing more than to have sex with you,” he wrote on Nov. 2. “You have a great little body. But I have to cover myself. Those pics I sent weren’t really me if you want the real ones and you’re really interested in hooking up Monday let me know.”
When questioned about the fake picture, he said, “because of our te difference in our age. I’m sorry. You could’ve been someone trolling trying to set up people.”
Despite his concern, Oliver tried to arrange a meeting, according to the complaint, “after her mother went to work,”
On Nov. 3, Oliver told the “child’ to go for a run near Bayshore Boulevard, according to the complaint. Air Force investigators watched him leave MacDill around 2 p.m. and drive around in the area he said he would meet the “child.”
He later wrote her saying he had driven around looking for her but couldn’t find her.
Oliver asked for another meeting and, on Nov. 4, while sitting in his Ford Focus while parked as his son’s football practice, engaged in more sexually explicit email conversations, according to the complaint.
Based on the email conversations and observations of Oliver leaving MacDill to seek out the “child,” he was arrested Nov. 5 and charged with coercion and enticement of a child for sex.
He was released from a Pinellas County Jail two days later on a $30,000 signature bond, according to court records, ordered to wear a GPS device and prevented from having unsupervised contact with minors, including his own children.
The Federal Public Defenders Office which is representing Oliver, did not immediately return a call and email seeking comment.
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