School District Forks Over $125,000 For Male Teen Student’s Mind-Blowing Sex Trauma With Teacher

Caswell YouTube screenshot/The Dr Phil Show

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A taxpayer-funded school district in Oklahoma has agreed to pay $125,000 to the family of a male teenager who was traumatized by a female middle school teacher with a slew of sex — including a stand-up-style romp in the back of her classroom and an intense, weeks-long, two-state, sex-filled romance.

The now-former teacher is Jennifer Caswell. She was 27 when at the time of the mind-blowing sex trauma (back in 2014).

Caswell was an English teacher at a middle school in tiny Hollis, Oklahoma (pop.: 2,060). The unidentified student was 15 years old and in eighth grade at the time.

Attorneys for Hollis Public Schools agreed to the $125,000 settlement last week, reports The Oklahoman.

The original $1 million federal lawsuit claimed pain, suffering and emotional anguish resulting from sexual encounters the student had with the twentysomething teacher.

The sex caused the student’s grades to drop, the mad dad alleged. Also, he stopped engaging in extracurricular activities.

The furious father also claimed that his son was humiliated when other students found out he was having sex with a 27-year-old teacher.

“The truth is that this has a terrible effect on a child,” Charles Watts, an attorney representing the family, told The Oklahoman. “You can expect in his future life that he will have a hard time with relationships.”

The student’s father testified in a deposition that then-school principal Marty Webb accused the student of falsely boasting about all the sex and instructed him “to keep his mouth closed” as rumors about the trysts with Caswell spread around school.

The father also swore that school officials threatened to punish his son — with paddling or perhaps in-school suspension — over the rumors. School officials deny this allegation.

Police arrested Caswell in June 2014 on statutory rape charges when they found her and the student in a Best Western motel room in Olive Branch, Mississippi, according to a contemporaneous story in The Oklahoman.

After the cold busting at the Olive Branch Best Western, the student spilled the beans. He told police he and Caswell had sex in her SUV, in her house and inside the home of her father — a local pastor.

Caswell was going through a divorce with her husband at the time of the sexcapades with the teen student.

The lonely teacher appeared on the Dr. Phil show in 2015 to discuss her star-crossed love affair. (RELATED: Teacher Who Had Standing-Up Classroom Sex With Teen Tells Dr. Phil She Was Lonely, Blames Ex-Husband)

The eighth grader was the aggressor, Caswell insisted. He constantly flirted with the teacher, complimented her and showered her with affection.

And it worked! One day, Caswell said, she let her guard down and had sex with the student standing up in the back of her classroom.

“He was flirty. I should have put a stop to it then, and I didn’t,” Caswell, who taught sixth, seventh and eighth graders said. “I wasn’t used to getting attention. It felt nice to have someone to compliment me and things like that, because I felt very unwanted.”

Caswell felt undesirable, she said, because her seven-year marriage was going badly at the time (when she was known as Jennifer Sexton).

“I never got complimented. Never even got a birthday present, Christmas present, for Valentine’s Day, nothing. I felt really bad about myself,” Caswell told Dr. Phil, choking back tears.

She griped to Dr. Phil that her no-good husband didn’t shower her with affection the way the unidentified 15-year-old student did.

“We didn’t fight, but that’s only because we didn’t talk. It was like living with a roommate,” she explained. “He would come home. He would talk on the phone to his friends for an hour or two, and then he would go to the playroom and play his Xbox until 1 or 2 in the morning.”

They didn’t hug or cuddle.

The teen with whom Caswell had a bunch of sex was way more amorous. He was “mature” and “funny.”

“He would always tell me how beautiful I was and how I was a good person on the inside,” Caswell told Dr. Phil.

“I never thought I’d be in this situation,” she lamented. “I’m not a monster and I’m not a predator. I made a stupid decision.”

Caswell, now 31, pleaded guilty to a bunch of sex crimes including second-degree rape and forcible sodomy.

A judge sentenced her to 10 years in prison.

She now resides at Mabel Bassett Correctional Center in McLoud, Oklahoma.

Her sentence requires her to serve at least eight and a half years in prison.

A federal lawsuit exclusively against Caswell for intentional infliction of emotional distress is ongoing, despite the fact that Caswell will likely be judgement-proof for the remainder of her life.

Lawsuits by male teens and their parents over sex flings with female high school teachers are surprisingly common in modern-day America.

The gold-standard case involved forensic science teacher Rachelle Heenan in the suburban sprawl beyond Dallas, Texas. A 2014 lawsuit alleged that the thirtysomething teacher repeatedly exploited a male student who was 17 years old at the time by engaging in raunchy sexting sessions and, eventually, a slew of sex romps. According to the lawsuit, all the sex so stunted the student emotionally that he was forced to postpone entry into the U.S. Marine Corps. (RELATED: Lawsuit: Teen’s Sex Romps With Female Teacher So Mind-Blowing He Can’t Join Marines)

Also in 2014, the family of a 17-year-old male student at Options Public Charter School in Washington, D.C. filed a $3 million lawsuit claiming that 22-year-old substitute teacher Symone Greene provided oral sex to him on the very first day of her teaching assignment, in her classroom, right behind the teacher’s desk. The student, a football player, allegedly asked Greene to engage in a number of sexual acts equal to the number on his football jersey. (RELATED: Family Of 17-Year-Old Male Student Who Received Oral Sex From Teacher Now Wants $3 Million)

A third 2014 lawsuit involved Pennsylvania English teacher Lauren Harrington-Cooper who had a tryst with at least one male student. Harrington-Cooper began the relationship with the senior after having his sister tell him she thought he was “hot.” There were a few dalliances that included oral sex and intercourse. The student’s parents say they found sexually explicit chat on their computer as well. A letter from an attorney for the male teen called him “a victim of sexual assault” who suffered “damages and injuries” as a result of sex with the 31-year-old English teacher. (RELATED: Sex With This Teacher Was So Traumatic For A Male Teenager He Plans To Sue School District)

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