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Introduction:

Part 1 is a slow build, with future parts ramping up

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.

She continued. “I think we need to start taking some gradual steps to get you past whatever this stress is about showing your body. Ok?”

“Um. OK,” I replied, but didn't actually know what I was agreeing to.

“Good! I’m glad you are on board,” she said, genuinely delighted. “OK, first I’ll go, then you follow my lead.”

“Lead? Mom, what are you talking about?”

But as I was saying this, my mom stood and slipped off her robe. I had assumed it was some sort of underwear underneath, but I was very wrong.

Underneath the robe was…nothing. My mom stood in front of me fully nude. Her pale skin was slightly flushed red. Her tits were incredible. So full and despite her age, retained all their perkiness. Her pussy was a tight slit and completely bare. She gave a small spin and showed off a perfect bubble butt that begged for a squeeze. Her legs were toned and shapely. She ran her hands gently over her skin. She seemed almost nervous, which would be a new thing for me to see from her. “Well?”

Despite how scantily clad my mom usually dressed, I had never actually seen her fully nude. It was the one last normal barrier, or so I thought at the time, that had not been crossed in the apartment. She was so undeniably hot and I could only stare and admire her shape and beauty. I felt my dick start to stir and I begged for it to stop.

I realized she had asked a question. “Uhhh… well what?” I said without taking my eyes off her tits.

She smiled. “Well. It’s your turn. Maybe start slow with your shirt. Or maybe all the way at once is better?" My mom kept the same casualness about this as she did with how she usually walked around the house. She made getting naked together seem as natural as could be.

“Better for what?!” I asked. “What are you asking mom?”

“Like I said, we are taking steps to get you comfortable. The first step is get used to being seen naked in the safest way. What’s safer than at home? With me?”

“Mom? What? I can't get naked with you? It’s just wrong,” I protested. Did she actually think I would just strip naked?

“I know you are feeling uncomfortable, but that is the point. I’ve been so open with my body for most of your life. I’ve seen you naked before. Let’s try.”

“Seeing me naked as a baby hardly counts mom,” I shot back.

“That’s fair. Just your shirt for now. Please? For me?” She made a pouty face and clasped her hand together in front of her. This had the effect of make her adorable but also pushed her tits together.

This was beyond strange. But a part of me liked it. I liked that a girl was working so hard to get me to take my clothes off. Nevermind that it was my mother. The attention was nibbling away a bit at the voice that told me to hide my body. She was right. I could do this with her. She's my mom and the last person I should be ashamed to have see me.

I gave a sigh and lifted my shirt over my head, letting it fall the the floor. I instinctively crossed my arms in front of me in a vain attempt to hide. I kept my eyes on the ground.

"Honey. You look really good," my mom said, genuinely. "Do you work out?"

I did, a lot in my attempts to look better. But I pushed back. "What are you talking about? I am way too skinny." I had inherited my mother's pale skin and thin body. I felt like a rail.

"Too skinny? You are thin, but you also look really toned," my mom said, not taking her eyes off my body. She stepped forward and without asking ran her fingers along my chest and stomach. "You even have a six-pack," she said. She then touched my face gently, and said "I'm so sorry you see yourself in such a different way than other people see you."

Her touch felt amazing. I had never let anyone touch me like this. I dropped my arms. Mom smiled to see me thaw a bit. She ran both her hands along my arms. She was so close, her tits grazing me as she caressed me. "And these arms. They are really sexy. You seem strong." She massaged and grabbed at my muscles, as if examining a prized horse. "Turn for me."

I let her turn me and felt her run her hands up and down my back. "Your shoulders are nice and broad too. It looks really manly with your lean figure."

I closed my eyes and enjoyed the sensation of her running her hands all around me. How could I have pushed away all the girls that wanted to do just this over the years? This is what I had been missing. That was a part of my shame as well. It's not like girls hadn't shown interest. But my disgust at my own body had always led to self-sabotage.

"Is this OK for you?" my mom asked as she stroked my back.

"Yea mom. It feels nice." Out of my control, my dick had also been responding to the attention.

She hugged me from behind and ran her hands over my chest and stomach. I felt her tits push into me. I could tell her nipples were hard. She was enjoying this too. "I'm so glad you could feel this relaxed with me. I'm very proud to have a son with a body like yours." She let go and turned me to face her. I looked at her face as she smiled at me approvingly. Then I saw her eyes widen a bit.

"And it seems there's more I should be proud of. Wow." I looked down and was horrified to see that I was pitching a massive tent underneath my towel. My dick was hard as steel and begging to burst from the towel. It's outline made it obvious to its size. I moved to cover up in embarrassment, but my mom grabbed my hand.

"Show me," she said, with a bit of demand in her voice.

"What?"

"Show me your dick," she said flatly.

"You're my mom. I can't just show you my dick," I stuttered. "Listen, you've already done so much to make me more comfortable. You are the first person in a long time to touch me without me wanting to scream. I love you so much more for that." I genuinely meant that too.

She smiled and let go of my hand to put her hand on the side of my face. "You're being so brave. And you have nothing to be ashamed of. I don't want to push you too hard." We smiled at each other. I was lucky to have a mother like her who could handle this so well.

"But sometimes you just have to listen to your mother." With a swift movement, she ripped the towel off of me and stepped back as I instinctively grabbed at the towel.

"Mom! No!" I yelled in horror. My attempts to cover were awkward and only did a partial job as my dick was fully hard. I was left to stand in front of my naked mother essentially grasping my fully hard cock that wanted nothing more than to cum buckets.

"I'm sorry, sweetie. I had to. Now let me get a look at you. Open up!" As she said this she herself opened her arms wide and took a more open stance with her legs. Her gorgeous body was fully on display. I knew before, but this left no doubt as to why men shelled over so much money to see her naked. Her tits bounced playfully, and her sex was a perfect pinkish slit, with not a hair in sight. In a mock threatening tone she said, "if you don't, I'll just have to come over there and make you."

I laughed at her playfulness and relaxed a bit. Her stance, her tone, the way she was acting like some new-wave body positivity coach. All of it was just so strange that it took some of the edge off. "You know this is weird right?"

She smiled, knowing she was getting to me. "I guess. But there are plenty of open families out there that are naked all the time. It doesn't have to be a big deal."

Slowly I let go of my manhood and let my arms fall to the side. My dick stood out proudly, and my head was glaring red from strain and desire.

I watched as my mom's face went from warm curiosity, to suddenly shift a bit more serious as she stared at it.

"Mom? What? Is it bad?"

Now she was the one to stutter. "Umm... No Josh. It's not bad at all. It's just..."

"What is it?!" I yelled in worry. My anxiety about my body was screaming, knowing it had been justified all along.

"Josh...you're...well, you're huge," she said, in a tone that conveyed how impressed she was.

"Huh?"

"Yea. You're penis is really nice." Her face turned almost clinical in how she was studying my member. "I see a lot of dicks, you know?"

"Yes, mom. I am aware," I chuckled. I had been vaguely aware that some men paid for "extra" liberties at the club. She had once eluded that it never included sex, but that some guys would pay to be able to jerk off to her in the VIP room.

"Yours is big, has good girth. I can tell the head is nice and fat and would feel great."

Did she just said that my dick would feel good to her?

"I mean..." and she took a step forward and extended her arm. I thought for a moment she was going to grab my dick. I felt suddenly ashamed that I didn't move back but instead subtly thrust my hip forward as if I wanted her to. Instead, she made a fist and compared my dick against her fist and forearm. It did indeed look impressive in the size comparison. The sensation of her skin grazing my shaft made it twitch. A tiny shiny orb of pre-cum shone at the tip. Fuck.

"Oh, sorry. I got carried away too fast," she apologized. "I know this is a lot and I had to push you already, but I didn't mean to...you know...do that," she said, pointing to the glistening pre-cum.

I was still well aware that I was making no move away from her. "It's ok, I guess. If it's ok with you." I then asked her shyly, "So...it's good? I...look good?"

She smiled sweetly at me. "Yes sweetie. You look better than good. I know a lot of the girls I work with would like nothing more to get a hold of you."

I smiled at her odd compliment. "Thanks. I think this is really helping."

"Good! Now on to the next phase of my plan!" She said, comically rubbing her hands together.

"What? This is enough. Honestly mom. I feel better. I think we are good."

"No, dear. We have more to do. And I have you like this, so I am going to keep going until I know you are OK. No son of mine is going to be ashamed of their body and not be able to enjoy everything it can do. I'm off to work for now, but we'll talk more over the weekend." She gave me a kiss and went into her room to get changed before she left.

I was left alone, in the living room, cock out and aroused. What the fuck had just happened? I made my way to my room and sat stunned on the edge of my bed. As soon as I heard the apartment door close, I jerked myself furiously to the memory of my mom's skin touching mine.

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