Lewis Hart also sent sexualised images to his landlord six months later during a campaign of harassment while he was on police bail.
The 36-year-old sent several messages to the woman telling her that he found her attractive, Teesside Crown Court heard.
Jon Harley, prosecuting, said Hart told the teenager that he wanted to ‘get it out of his system’ when he sent her the sexually explicit images last May.
He said the defendant sent a WhatsApp message to the woman while he was intoxicated and the harassment had left the victim feeling physically sick.
Lewis Hart (Image: Cleveland Police)
Hart, of Blackmore Close, Guisborough, pleaded guilty to sending sexual communication to a child, sent a photograph or video to cause alarm, distress or humiliation, and cause harassment without violence.
John Nixon, mitigating, said the father had become ‘low and desperate’ when he committed the offences.
“It doesn’t excuse what happened but does show that it was out of character and is something that he bitterly regrets indeed,” he added.
“There is a very good prospect of rehabilitation and little likelihood of further offences being committed. He still plays a role in the life of his biological children and there is hope for the future.”
Judge Timothy Stead jailed Hart for a total of 16 months.
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He said: “It is understood that you and your family had been having a difficult time and your own mental health has not always been good.
“The difficulty in this case lies in the most serious offence in this case, sexual communication with a child, is an offence committed against a 14-year-old.
“You sent six images to her and are undoubtedly of a sexual nature and most people would find them troubling and disgusting.”
Hart was also ordered to sign on the sex offenders’ register for ten years and was made subject of a ten-year restraining order.