Chapter 1

I opened the front door of our modest apartment, tossed by backpack carelessly on the ground, and made my way to my bedroom, all but slamming the door behind me. I flopped down on the bed and buried my head in my pillow. I was completely exhausted and frustrated by another long day at school.

It’s not that I am a bad student and struggling academically. That’s all fine actually. School comes pretty easy to me. And it’s not for a lack of friends either. While not the most popular boy in school, I had a great group of friends that I knew appreciated me. It was something else that I had tried to hide for so long, and now I wasn’t sure if I could keep hiding it. I hated my body. I felt too skinny, unattractive, and not masculine. No matter the attention I got, or positive feedback I heard, I knew deep down I would be a lonely loser my whole life because my body just wasn’t attractive. And now that we were swimming at school, there was no way to hide it.

“What’s wrong, Josh,” mom said, coming out of the kitchen. She had obviously had heard me making an angry ruckus as I came home.

“Nothing,” I muttered unconvincingly.

This was my second problem actually. Mom, as loving as she was, was one person I felt I could never talk to about this. She just wouldn’t get it. How I knew she wouldn’t get it - because of her job. My mom was a stripper at a high-end club. How could someone like that be able to help someone like me?

I had known for a few years now. Growing up, I just knew that mom worked a lot at night and that it was a secret place I couldn’t visit. When it came to ‘Bring your parent to school’ day, where mom would have to talk about her job, she would always just say she worked for an entertainment company doing customer service. Thinking back, she wasn’t lying about the “service” part for sure. Sometimes mom would have very good-looking colleagues come home from work with her and I thought nothing of it. It wasn’t until about three years ago that I learned the truth. And mom was the one to tell me.

One day, she had sat me down at the dining table and told me about her job. She explained that business had been going well and as she got more popular and I turned 18, there was a chance someone would find out and tell me before she could tell me herself. I was shocked as I had avoided thinking of my mom as a sexual being all together. I finally took a real look at her at that time and realized she really was a MILF. She had long, wavy red hair that was often tied in a messy bun at the top of her head. She had a graceful long neck and perfectly clear pale skin. That day she was wearing a normal t-shirt that was cut off to just a bit below her ample C cup tits. She wore a comically short skirt that barely covered her ass and reminded me of an anime school girl. I am actually pretty sure that is what she google searched to find it. Looking back on it now, you’d think I was the most dense kid in the world to not realize something was up.

Since I was pretty young, my mom had dressed pretty openly at home. Of course none of my friends knew. I did not want to deal with them spreading rumors about her all over school. Around them, she at least made some effort to cover up. But on normal days when it was just us, she felt free to dress as she wished. Which was usually pretty skimpy. It’s just who she is. After she told me, it took me a while to not feel weird about it. Especially since I was in the prime ‘jerk-off any chance I get’ time of my life. But like all things, you get used to it and it stops even being that notable.

“Well, you must be starved,” she said, heading back into the kitchen and returning with a pot of pasta and a plate to serve me at the table. She was dressed today in a tight t-shirt that left barely anything to the imagination about her big natural tits. Try as I might, sometimes I couldn’t totally block out her blatant sexuality. Just cuz she was my mom, doesn’t mean she wasn’t hot. Her tits jiggled as she made her way to the table.

“How was school?” she asked.

“Fine,” I said, again unable to hide my obvious anguish, especially as I did not even bother looking up from my plate.

Mom sat down across from me. “Josh, I can tell something is wrong. Maybe I can help?”

“It’s no big deal. I’m fine,” I replied. I did want to tell her, but there’s no way she could help. I really felt that she of all people wouldn’t be able to understand what it’s like to not feel comfortable in your own skin.

“OK, but I am here if you want to talk about it,” she said, somewhat sadly. We made idle chit chat and then settled in on the couch to watch TV. I had my feet up on the coffee table, and she had her legs resting on mine. I looked over and could see far up her thigh owing to her tiny booty shorts that had ridden up. Each time I glanced at her I could see she was looking back at me with concern.

After some time, I excused myself to go to bed. She immediately stood up and gave me a hug.

“I know I am your old mom and you think I won’t get your problems. But I love you, and would do anything to help you get through whatever it is.”

I hugged her back and let myself enjoy her love and support for that moment. I was also just a tiny bit aware of the feeling of her tits against me. “I know mom. Thank you. Love you too.”

I stayed in my room the rest of night and just dicked around online. From across the apartment I heard my mom eventually go to her room and shut the door.

The next morning I woke up to alluring smell of bacon in the kitchen. I made my way out just in time to see my mom placing the bacon on a table spread with pancakes and fresh fruit.

“Morning sleepy!” she said cheerfully. Surprisingly she was wearing a relatively modest pajama set that was still flowy enough that I caught glimpses of her breasts down her shirt when she bent over a bit.

“Morning. This looks great!,” I said, referring to the food. “Thank you.”

“Anything for my guy,” she said and gave me a kiss on the forehead. Her breasts basically smothered my face for a brief moment.

We ate breakfast and made light talk, but at some point my mom’s face got a bit serious. “OK, you seem to be in a better mood. But I’m not. It’s really hard for me to see how upset you are after school sometimes. I need you to tell me what’s going on.”

“It’s nothing mom. Just give it a rest,” I begged.

“No. I can’t, honey. A mother needs to know.” She reached across the small table and put her hand on mine.

I looked up and was really touched by the concern in her eyes. “Fine,” I said.

She gave a smile and looked a bit more hopeful. Her green eyes against her pale skin and red hair were so striking and beautiful.

“I ... I don’t like going swimming at school.” I looked up, and she had a puzzled expression on her face.

“Ok ... so...”

“Every day for the past month we have had swimming at school. It’s supposed to be fun and everyone loves it. But I always sit out.”

“You’ve always been a great swimmer!” my mom encouraged. “I used to have to drag you out of the pool when it was time to leave.”

“That was when I was little,” I tried to explain. “It just feels different now. I ... I just don’t want people to see ... to see my body.” As I said this, I looked down and couldn’t bare to see that puzzled look on my mom’s face. I had had the feeling that she couldn’t understand and now that I had opened up, I was afraid my fears were being confirmed.

There was a long silence. So long, that I couldn’t help but look up to see what was going on. When I did, I saw the tears welling in my mother’s eyes, and she looked on me with such love. She got up and hugged my head tight. Her soft tits fully pressed into my face as she embraced me.

“Oh, my boy. I wish you could have told me sooner.” She kept me in her embrace and stroked my hair. “It’s totally normal to be concerned about your body. You just need to build your confidence.”

She made it sound so easy. A little anger rose in me at her assumption of what it would take. “That’s easy for you to say,” I said with an edge in my voice. “You don’t have to deal with this at all.”

My mom pulled me back, but still held my head. Rather than meet my anger with hers, she had a small smile on her face. “You’re right about that. Any stress about my body is long gone. But,” she said and gave a little kiss to my head, “that doesn’t mean I didn’t go through a phase where I was shy about being seen. Even when I started dancing, I was shy. But with years of practice, I’ve learned to love this,” she said, gesturing to her body. “And I can help you love yours too. It’s part of a mother’s job.” She released me from the hug, and started walking to her bedroom. “You need to go to school and I have a lot to do before work. It’s a late night, so we will talk again tomorrow. Let mommy think about it for a bit. Clear the table before you leave, please.”

“Thanks mom,” I replied. I was doubtful that she could do anything and assumed she just didn’t know what else to say but wanted me to feel cared for. Which I did. I cleaned up breakfast after I had finished, just as she asked, got ready, then headed out to school.

The day was pretty uneventful, but ended with a gym session and no swim (thank God), so when I got home I knew I had to shower immediately. I hopped in the shower and enjoyed the heat loosening up my muscles after an intense workout. I wrapped a towel around my waist and avoided the mirror as I put a clean shirt on.

As I left the bathroom, I was surprised to see my mom sitting on the couch waiting for me. She wore her hair up in a messy bun and had a silk robe on which usually meant there was just underwear underneath.

“Hi Josh. Welcome home,” she greeted warmly.

“Hey mom. Still home? I figured you’d be on your way to work by now.”

“I pushed back my shift after our talk this morning. Come, sit. I want to talk some more.” She patted the spot on the couch next to her.

“Uh, sure,” I said reluctantly. I hadn’t remembered that she had promised to think about my problem and come up with something to help. To be honest, I just wanted her to forget about it.

I sat near her on the couch, and she immediately moved to close the gap between us. She took my hand and looked me directly in the eye.

“I thought a lot about how you feel ashamed of your body. I even spoke with a few of my coworkers about it.”

I was never fully clear if when she mentioned coworkers, these were fellow strippers or if they were the men paying her.