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The Jock’s Secret Crush

Chapter 36

Ch. 37 / 63 Dec 16, 2025

“You were in prison?” she asked.

It takes guts to become this vulnerable to someone, and I hadn’t talked to anyone about the heavy stuff since I’d been in prison.I hadn’t told Emily everything yet but it still felt great to get this off my chest. If I wanted something real with her, I had to be the one to start talking.

She’d been honest with me and bared her soul, telling me about her deepest insecurities while thinking of me as a good guy.

It was wrong of me to pretend to be one.

If she met the Seth back at my dad’s farm two years ago, she wouldn’t even recognize me because I wasn’t the same guy. A lot of shit happened, and it changed me, for better or for worse, I wasn’t sure but when I came out of juvie, I promised myself I wasn’t going to be that self-destructive boy.

It wasn’t fair how I painted this amazing picture for Emily to see when it was far from the truth.

She needed to accept all of me. The truth, the lies, the ugly so here I was, telling her things that no one knew except for my mom, dad, coach, and Sky.

To my surprise, she burst into a giggle, slapping my chest playfully. “Not funny.”

I cringed inwardly.

She thought I was so perfect that I could never go to prison.

When she realized that I wasn’t laughing, she stopped. Her dark honey eyes blazed with confusion and then for the first time, I saw fear within them.

“You’re serious right now?”

“I wish I was joking about this. I want to be honest with you, Emily as you have been with me.” I raised my hand, palm up towards her to see how she would react.

She could be accepting or she couple totally flip. I had to be ready.

Tentatively, she placed her small hand in mine. That was enough to tell me that Emily would listen to me no matter what.

“I’m gonna have to tell you from the start.” I began, “Emily, I used to be a male escort.”

I waited to see the disgust cross her features but surprisingly she kept her expressions schooled. I guess when I told her I’d been to prison, she’d expected me to tell her I was some kind of a cold-blooded murderer so being a male escort paled in comparison.

“But you were only sixteen.” She said.

“I didn’t look like it. I was a teenage escort, clients have tastes like that and I looked older than most boys my age. It worked out. Anyway, my job was basically to just accompany wealthy ladies to parties. That’s all I had to do, but sometimes they needed other services.”

She nodded, still keeping a straight face.

“I did that for extra cash. But, to be honest with you, I did it to rile up my father. He wanted me to be a perfect son and I wanted to show him that I wasn’t.”

“Why?”

“Dad’s a certified womanizer, he’s always been. He’s a cheater, he cheated on my mother before I was even out of the crib and it went on for ages. He was always with someone. I was used to seeing him bring women as soon as my mother stepped out for work.” I ran my hand through my hair, “he did it while I was in the house, Emily. Do you know how fucked up that is? I was only four when I first started seeing this.”

“That’s awful for a child to see his father constantly cheating.”

“And what’s even worse is when I got older and confronted him about it, he said it’s normal for men to have side chicks. He said my mom was different but he was allowed to have more. I grew up thinking men could screw around.”

“Why did your mom let this happen?”

“Because she loved him and she thought he would change.”

I couldn’t forget it even if I tried. Being ten and watching Dad screw a lady from the neighborhood, the nice one, the one who always brought baked cookies and chatted with my mother. The ladies threw themselves at him, Monroe Senior took good care of them. That day I came home from school and heard the moans and grunts only to be welcomed by the hideous sight. Then something even worse happened, Mom walked in.

It was followed by the lady doing a walk of shame, but in her case, she just gloated in front of my mother almost saying ′look I got a piece of your husband too.′ and then both my parents were screaming obscenities at each other while I stayed there and listened. Something turned off at that time, things changed.

“When I was fourteen, mom’s had enough so she filed for divorce. Anyway, I’m getting off track. I basically did escort work as revenge to show my father that I was no better than he was. Stupid, I know but he knew I was talented in hockey so I was about to use that against him by soiling his name.”

Emily listened to me without being judgmental, maybe the things I was about to tell her next would change that.

“There was an older group I was hanging out with, they got me into some other serious shit.”

“I remember you told me they were your friends.”

“Well, some friends they were.”

She touched my shoulder, I looked at her hand on my bicep, caressing slowly, urging me to go on, listening intently.

“What I’m about to tell you might change how you see me.”

What’s the worst that could happen? She would tell me to pack and maybe even ask me to leave her brother’s studio and move into my old accommodation. I would hate not having to kiss her, or touch her, to be on the receiving end of those smiles, but it was now or never.

“We’d been drinking heavily that night. There were four of us. Mike, Chip, Evan, and I. Mike was the one with the craziest ideas, he was seventeen at the time. I was sixteen. After a few beers, we were driving around town, and Mike started to dare us. He dared Chip to go into an old factory and start a fire.”

Emily looked shocked.

“I insisted it was a bad idea, but they didn’t listen to me. Nobody listened and they started yelling, calling me names. It wasn’t long before Mike realized what we’d done. The entire building caught fire. I rushed out of the car to put out the fire but it was too late. When I tried asking the boys for help, they left me there.”

Emily’s hand tightened around mine, “Did someone get hurt?”

"Yes, there was someone.” I swallowed as bile rose in my throat, reviving that ugly night. “When the police came for investigation, they told them it was my idea to start the arson.”

“That is disgusting!”

“Chip said I was the perpetrator and the others backed up that story. They came from good families so they could have gotten off easily but luckily, I had proof. During the conversation in the car, I’d taken a Snapchat video of the boys discussing the plan. I showed the footage to the judge. I thought if I was going down, I was going to take them with me.”

Emily waited patiently for me to complete. I was scared to even look at her, I wasn’t ready for her disgust or revulsion but I was also a greedy bastard, so a part of me hoped she would forgive me after all this.

“A man was injured in the arson. He was a guard and he’d seen me trying to put out the fire. He was my alibi, he told the court the truth. We were still charged with third-degree-arson and one-fifty thousand dollars worth of damages.”

I hadn’t heard a peep from her so I went on. “Since I wasn’t part of the plan, my sentence was shorter. One year in juvie and twenty-five grand as a fine which I’m still paying to this day. The other boys got three years but they are out on probation.”

She hadn’t let go of my hand so I thought that was a good sign.

“That’s my truth. You know everything now.”

“It must have been tough...in juvie, I mean.”

“It was bad but I managed to spend a year there. There were pretty dangerous kids there doing time for violent crimes like murder or rape. Everyone stayed away from me because they were probably scared of my death glares.” I laughed humorlessly thinking of that one time an intimidating guy who was a year older than I asked if I would like to have some “fun” which was his idea of sucking dick.

“I’ve wanted to tell you this for a while. I’m happy I did. I really didn’t want you to think you ended up sleeping with an ex-convict.”

She shook her head, “Thank you for sharing this with me, and it doesn’t change anything.” She leaned forward and kissed my lips lightly.

I wasn’t ready to hear what she said next.

“I still want you, Seth.”