Midlife Crisis Mistress

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Written by Jordan Upshaw

Names have been changed to protect anonymity.

When John was 16 he was expelled from boarding school. He was sent home while the administration decided whether or not to allow him to return.

Depressed and facing an uncertain future, John’s mother decided to send him to a hot yoga class made up of single divorcée moms during the time he would have normally been at school.

His mother’s best friend, River, was the yoga instructor. She was in her mid-forties. John thought she was “a cool yoga instructor” and someone who was easy to talk to.

“We just started talking and she’s just like an awesome person all around. She’s just the coolest person ever. She’s so much fun to go out with on a Saturday night.”

John’s boarding school ruled not to allow him to return. This meant he had to begin attending public school for the first time in his life. Due to his dyslexia and ADD, John had always struggled with English, and being out of school for so long had worsened the problem. So his mother enlisted River to tutor him.

At first they bonded over a mutual love of the English language and learning. Their friendship grew from there.

“She started out telling me a little bit about her life and her first divorce and her daughter. It started out like that and then just evolved naturally into more and more heavy stuff.”

After a few weeks, the friendship turned into an affair.

“We were in her kitchen and I decided to, I don’t know, just make a move, see what happened. I was feeling it. I thought she was feeling it and clearly she was. She didn’t hesitate at all.”

After they had sex, River drove him home like normal. John thought it was going to be a one-time thing. But the next time he went to her house for tutoring she was the one who made a move. John described his thoughts at the time as pleasantly surprised. “Alright, well I guess this is happening. And then it just kept happening.”

John says sex didn’t affect their friendship at all. After they started sleeping together, River confided in John about more serious topics such as her husband’s struggles with addiction and the childhood sexual abuse she endured at the hands of a relative—topics she felt she couldn’t talk to her husband about.

Since River’s husband didn’t live in the house and she didn’t wear a wedding ring, John assumed they were no longer together.

“It was kind of just free range for her to get stuff off her chest because she didn’t have anybody to talk to about that.”

“I would talk about me getting kicked out of boarding school which was a really tough time for me. We were just kind of each other’s therapists. She knew that I wasn’t going to say anything to anybody.”

The only person John told about the affair at the time was his younger brother.

John didn’t have a driver’s license yet so River started picking him up from school to take him to her house for tutoring, drugs, and sex.

“I was doing an 8 ball of molly a week. I used to sell it. So I used to bring molly over and all sorts of stuff.

“We sort of had a deal going because she loved my ADD meds. We would do drugs and fuck all of the time. Or drink alcohol and fuck. I would trade her ADD meds for alcohol. Even if I didn’t give her pills she would still buy alcohol for me and all my friends as long as my mom didn’t find out.

“I didn’t think of myself as a mistress. It never felt like she was buying me things. It was a friendship.”

Aside from Adderall and molly, they would also do various prescription painkillers, codeine, cocaine, and Xanax before sex. They never used protection, something John now chalks up to being “young and dumb.”

They usually saw each other two or three times a week, not always for drugs and sex. “I actually did use her as a tutor. My school got out at 2:45, she’d pick me up, we’d do some work, fuck, then go pick up her daughter and my brother at 5:00. Then we’d all hang out.”

Legally the relationship amounted to statutory rape, but John maintains River never took advantage of him.

John had been having sex with girls his own age for about a year prior to meeting her. “She was the fourth person I’d had sex with. I was her number 50. I knew what I was doing. She definitely didn’t take advantage of me.”

“When we were together it was like we were best friends. I never saw her as ‘the cool mom,’ I saw her as an actual friend. We still would’ve been friends even if this had never happened. It was never weird. The only weird part was having to hide shit from my mom.”

John and his mother are very close but the affair with River was something he’s kept a secret from her.

John explained River always felt more like a friend than an adult. The age difference never gave him pause. “To us it wasn’t weird. She always said I was very mature for my age. I’ve always tried to be as mature as possible and I think that’s kind of what it was. It wasn’t the age for her, I don’t think she was thinking about age. I wasn’t like a little 16-year-old kid. That’s why we got along.

“We’d sleep together and then afterwards it was just back to regular life. A momentary lapse in reality is the best way to put it. We ignored the rest of the world for like an hour and just said, ‘Fuck it. Let’s do whatever we want. Let’s get drunk and fuck, who cares?’ And then we can go back to having to deal with the real world. And that was the fun of it.

“That’s what it was for both of us. I forgot about getting kicked out of school and all the stress. And her dealing with everything in her life. It was perfect because we both needed it. We felt equal in everything that we did.”

John didn’t realize River was still married until the end of the relationship when she told him her husband was coming home from working out of state. “I felt like it wasn’t my place to ask [about her husband]. If she wanted to tell me then she would’ve.”

River’s marital status never bothered John. “I was in that teenage kid stage where it was kind of cool. Even now, if I had sex with a woman who was married I still wouldn’t care.

If I wasn’t comfortable with it, I would’ve said no. And she would’ve said no too.”

After awhile that’s exactly what happened. River told John she was no longer comfortable with them having sex.

“At a certain point she felt like she was holding me back from going out and doing stuff with people my own age. She didn’t want to interfere with my high school experience.

“I still don’t know why she ended it. She just said she wanted to and I was fine with that. I’m sure she had her reasons.”

Shortly after the affair ended, River moved to another state with her husband and daughter.

“I wouldn’t say I was upset about it. I wasn’t disappointed. We aren’t up at night wondering what could have been. We knew it couldn’t turn into anything more. She was just fun. Even now, she’s just like the most fun person.”

John had been bullied for most of his childhood and up until high school he had very few friends. He says his relationship with River helped him to overcome the insecurities he suffered from at the time.

“It turned the tide for my self confidence. Afterwards, I was happy. I knew how to talk to girls now. That’s when I stopped being bullied, when I stopped caring what other people thought. It just made me feel better about myself. It made me feel like I was somebody.

“We’ve moved on with our lives now. That was a part of our lives that we laugh about. It was a great part of our lives. It made both of us much better people. It made me a much better person and I learned a lot. Not just sexually, but about myself. It made me happier as a person. It made her happier as a person too.

“Nothing [about the friendship] changed. We just stopped sleeping together. The entire time, it was a friendship. It wasn’t based on sex. It was more heavily based on friends than benefits and that continued after we stopped sleeping together. That’s what made the friendship last.

“I never had second thoughts. I don’t think she did either, even now.”

John still talks to River sometimes. They text occasionally. She sends him a birthday card every year. When he turned 21, five years after the affair, he received one in the mail that said: “Happy Birthday to My Midlife Crisis.”

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