As a hardcore fan of this story, I want to continue it and ensure Jake faces many dilemmas. The credit belongs to Willy D for the original story.

Jake’s Dilemma by Willy D..
Jake’s Dilemma – Mom’s POV by TPK.

*****

Jake’s Next Dillemma…

It happened, and it wasn’t a nightmare. I was a nudist at home in privacy, but my stepmom exposed me to almost the entire neighborhood. Everyone saw my naked body. There was no going back to what they thought of me before. They now knew how small, smooth, and pathetic my penis was, and they will never forget it.

Since that happened six days ago, I couldn’t stop reliving the horror in my head. When my swim trunks hit the floor and everyone looked between my legs, that moment was recorded in my head. It wouldn’t quit playing. I wish something would take away this feeling of humiliation. I was in bed, anxious and scared of how else I could be embarrassed.

I can’t believe so many of my neighbors saw me naked last week, and some were even passively mocking me. I have to live next to these people for a long time. How will I ever get over this? While this happened last Sunday, I still can’t get over it. I was lying naked in bed, and I looked underneath the covers at my naked body. My penis was just sad, bald, and incredibly tiny. Why was I crucified with this unbelievably small penis?

I wish I had never been born like this. I am built like a little boy, and it looked like I never fully grown like men typically do. This is what I get for being a pervert and allowing this to happen, but my stepmother couldn’t know the truth. It would ruin everything, and I couldn’t let that happen. Most people would think I was foolish for letting it get so out of hand. But trust me, my stepmother will never see me as a pervert. She is my stepmother, and I love her. For the sake of our relationship, I needed to keep on lying indefinitely. I’d rather have the reputation as an innocent guy with a very small penis than a pervert who physically gets off from the water jets in the pool.

Like before, I would be able to handle everything. It couldn’t get much worse. I walked into the living room, and my stepmom had a few gardening tools.

She smiled at my stark naked body and said, “Jake, I need your help with the garden today.”

I hated gardening, so I sighed and replied, “Okay. What do you need help with?”

I was on my way to the backyard when my stepmom stopped me.

“Jake, where are you going?”

“To the backyard,” as I pointed to the transparent door.

“Silly Jake. No. I need help in the front.”

“Okay,” I said, heading back to my room. “Just let me put some clothes on.”

She confusingly asked, “Why?”

I turned to her with a perplexed look. Did she just ask me why I wanted to wear clothes in the front yard of her house? She couldn’t have expected me to work like this. Everyone would see me.

“But I’m still naked. Everyone will see me like this.”

“Yes, you are naked, indeed, with your adorable little pee-pee down there. And yes, I understand your hesitation, Jake, but you should be fine. You bravely swam in the nude with most of the neighbors here. You don’t have anything to hide anymore, quite literally.”

Why was this happening to me?

“But.” I stammered.

“Jake. I’ve told you many times at this point. I want you to feel comfortable all the time. You don’t like wearing clothes. So, you don’t need to right now or ever. And besides, it’s just a little gardening.”

I couldn’t argue with her request because it made logical sense. I had to do this to protect my dignity. She saw me as a nudist, and I needed to continue being that way. It was my identity, but how much would she expand on that title? She forcefully threw the door open before I could mentally prepare myself for commanding the outside world with my little weenie. The subtle rays of light traveled through the house, and I was more than nervous.

Even though most of the neighborhood saw me naked and would always know how tiny I was, there were still other people who hadn’t seen what I could offer to the ladies. I was hoping for my body to remain a secret, but pretty soon, the whole neighborhood would be aware of how I looked. Every inch and cavity will be known. I couldn’t handle that fate.

I walked outside and felt the coolness touch my body. I felt incredibly exposed and vulnerable. Anyone passing by would see my naked body and what little I offered. The sun was out, but the outside felt really lovely and cool. I looked around the street. I felt relieved because I couldn’t see anyone.

My stepmom handed me a shovel and a pot of tulips.

As I dug through the cold dirt, she said, “Jake, be careful. There may be some earthworms in the ground. You don’t want them biting off your little worm,” as she giggled. I just continued working.

I was distracted by the hard labor; I didn’t even worry about my naked body. If I can finish this quickly enough, I can escape.

As I thought about how I could finish faster, out of nowhere, I heard, “Hi, neighbors!”

My stepmother turned and smiled at a mysterious man.

“Mr. Rogers. How are you on this fine Saturday?” She positively asked.

“Same old. Same old. I am still getting settled.” I didn’t want to turn around. I was praying he wouldn’t acknowledge me. “Wow. This must be Jake.”

Why would I think he wouldn’t address a fully naked boy working in the front yard? I didn’t know Mr. Rogers because he was new to the neighborhood. My stepmom was a social butterfly, so she knew everyone, which meant everyone knew me by default.

I turned my head and greeted him with a soft “Hi.”

I couldn’t believe this was the Mr. Rogers she spoke of before. He was a very tall and masculine man with a full beard. He was built like a lumberjack or something only the manifest of men could do. His intimidating voice alone was filled with testosterone.

“Jake, your Mom here mentioned you were a nudist, but I didn’t know you were this brave.”

I knew exactly what this man was referring to. I was bent over planting a tulip. I could feel his eyes wander over my smooth, little butt. Many women have seen my body without clothes, but this felt different. I felt even more exposed from the perspective of a mature and traditionally masculine man. He had a full, unfiltered view of my smooth, little butt. It was downright humiliating.

What was even worse was how my body was laid out. I know he noticed my scared, tight hole. I felt the wind gracefully massage my white, bare butt. It was a reminder of why I’ve been perpetually embarrassed since I decided to live with my stepmom.

“Thanks, I guess. Being nude is quite fun.”

“I agree with you. I enjoy it as well. But I could never be at your level. Being nude in the front yard is a bold statement.”

“Thank you, sir.”

“Well, it was a pleasure meeting you both, but I should,” –

Before he could finish, she said, “Jake. Don’t be rude. Come and greet Mr. Rogers.”

“No, it’s okay. The boy is working hard.”

“That’s not the Jake I’ve raised. Jake, come meet our nice neighbor.”

Why didn’t she just let him leave? I knew she was going to ask something so ridiculous of me. I was in the perfect spot before. At least he would have only been given the pleasure of seeing my behind; now he’ll see exactly what has caused so much shame and humiliation in the damn front.

“Yes, Mom,” I muttered.

I turned around and walked to them as they stood by the sidewalk.

“Sorry for Jake’s behavior. He’s a little shy so that I wouldn’t blame him.”

He looked at my stepmom and said, “Oh, I understand. I have a seven-year-old cousin I babysit. He is also shy, so it’s no big deal to me. He reminds me of Jake, in a way. He’s always running around naked. He’s just the cutest thing.”

“Sounds like my little Jake.”

I could feel my little bald penis bouncing and wiggling around. It was a blessing they were looking at each other. I finally approached them, and they both looked right at me. She innocently smiled. How could she think this was a normal interaction?

Predictably, Mr. Rogers looked directly down at what I didn’t want anyone ever to see. He was focused on my little, tiny, skinny, less than an inch (due to the modest cold) ding-a-ling. My ridiculously small pee-pee may be extremely microscopic, but it was always the first thing people noticed. It would be a dream for someone to avoid seeing it. My cock, which would be more appropriate for a little boy, has been through enough.

His eyes widened, clearly shocked and dismayed by what he was seeing. He couldn’t stop looking at the little guy attached to my legs. He was genuinely curious how a grown man could be so small where it mattered. Eventually, my face turned red from this embarrassment. He finally avoided my male anatomy and coughed to regain composure.

He stuck out his hand and claimed, “It’s nice to meet you, Jake.”

“Likewise,” and I shook his big hands. Half of his entire pinky finger was thicker and longer than when my little penis was fully hard.

There was an awkward silence until my stepmom blurted out, “Now, you can see why Jake may have been just a LITTLE shy.”

I was surprised my stepmom would say that to a stranger. At this point, actually, I’m not even surprised. She was just naïve and didn’t realize how embarrassing this was for me. She didn’t understand what it was like to have a tiny penis. It was awful and beyond uncomfortable.

“Mom!” I shouted.

“Jake, it’s fine. I can definitely see why,” as his gaze veered away from my unfortunate, tiny private parts. I couldn’t believe these two were openly discussing the size of my penis right in front of me. Mr. Rogers noticed the redness in my face. “Oh no, Jake. I’m sorry. Please don’t feel bad at all. There is no shame in being a nudist.”

“Really?” I asked.

I thought he was going to poke fun at what was poking out at him like a little minnow.

“Of course, buddy. I admire you for showing your body to the world. I think you have amazing confidence.”

I was about to thank him until she interrupted him by saying, “Yes, I always tell him he is an adorable boy. Any girl would be lucky to have him and his little pee-pee.”

My face turned even redder. She just admitted to this neighbor that my penis was really tiny. It was blatantly obvious, and he clearly already knew that. Did she have to acknowledge it right in front of him?

He saw I wasn’t amused. He didn’t even crack a smile. He rolled his eyes and said, “Well, he may be smaller than most boys, but I think he looks great.” I dumbfoundedly looked at him. He noticed and reacted by smiling. “Don’t worry what anyone thinks about you, Jake. If anyone messes with you, have them see me.”

I actually felt very comforted by Mr. Rogers. He didn’t even play along with my stepmom’s comments. I felt protected by him. He was the only one who didn’t feel the need to humiliate what I was packing. I was liberated.

“I also really like the smooth look you got there.” I laughed and thanked him. I wasn’t even bothered that he was carefully looking at my little penis. “You must shave it then.”

“Oh no, Jake doesn’t shave at all. He doesn’t grow any hair down there.” She looked at Mr. Rogers with discomfort.

“Well, I like it,” and he winked at me.

“Well, thanks for visiting, Mr. Rogers.” My stepmom said with a hint of sarcasm.

He leered at my little penis and said, “It was wonderful meeting you, Jake.”

He pulled me in for a suggestive hug. I never felt more safe and desired. He walked away, and I felt attractive, but not in a mocking way.

My stepmom screeched, “C’mon Jake. Get you and your little thing back to work. There’s tons to do,” as she pulled my ear.

After a few uneventful hours, we were finally done with everything. A few neighbors saw my naked body, but none of them said anything. I was grateful no one made it a big deal because the hard work and cold weather caused my penis to shrink inside me physically. It was like that the entire time. I couldn’t stop thinking about Mr. Rogers. He made me feel good about myself. I’ve never felt that way about my body before. It was always the source of humiliation for me.

We entered the house, and I asked if we were done. She nodded, and that was my cue to take a shower. I turned it on and almost immediately felt the water run down my sweaty body. I was lost in my thoughts in the steamy water until my completely naked stepmother entered the shower with me.

“Mom, what are you doing?” I shrieked.

“Well, Jakey, what’s the point in wasting water? We are both filthy.”

The shower wasn’t built for two people, so our bodies rubbed against each other. The way her body felt against mine was magical. I couldn’t think about anything else.

“Jake, let me wash your back for you.”

I didn’t question her; I just let her slowly do that. Chills ran through my body each time she touched me with her soft hands. She was so attractive, and I felt terrible for viscerally reacting this way.

I looked down and saw my little penis wake up from a shrunken slumber. It was around two inches, which was the hardest I could get. The way my back felt as she prudently rubbed it was heavenly. She finally reached my milky white butt and inserted the soap bar into it. She wasn’t aggressive or anything, but it was a strange stimulation. I’ve never had something placed in me that far.

She handed me the soap bar, “Okay, Jake. My turn. Do me.”

“Wait, what?”

“Haha, silly boy. Wash my back now.”

“Oh, right. Sorry.”

She turned around, and my mouth dropped, seeing her full-figured bubble butt. As I said before, it was abnormally large compared to the rest of her body. But I am not complaining. I gently massaged her back and started washing it. I was so lost in cleaning my stepmother that I forgot to try and control the blood rushing to my tiny pee-pee.

“Jake, you haven’t even finished my back. Why are you washing my bum?”

Oh my goodness!

Since our bodies were touching each other, she felt my little hard wee-wee brush against her butt crack. I was mortified and couldn’t say anything.

“Oh, I’m sorry, so sorry. I didn’t mean to.”

I backed up a little so the wall held my back.

“Haha, don’t worry about it, honey.”

I couldn’t take it anymore. The way the water dripped down her beautiful body. I didn’t have control over myself anymore. Without even touching myself, my little tiny cock exploded.

“Mmmph.”

She heard my moan and asked, “Jake, are you okay?”

“Yes,” I said. I was a little out of breath. I just wanted to collapse on the floor.

I was surprised by how much came out, but I couldn’t believe what had happened. Some of it landed on my mother’s backside. I could see my clear juices running down her back and seeping into her ample butt. I quickly washed it away without her noticing.

She finished showering, and she turned around. Despite my recent deliverance, I still had a very small boner. It wouldn’t go down. She looked right at it and smirked.

“Make sure you wash your cute little winky.” She grabbed my little teeny boner with two fingers. “Like this, Jake.”

She rubbed a little bit of soap on her hands, and she gently massaged my erect penis. I gasped, which caused her to snicker. After exiting the shower, I felt soothed by her absence. I can’t believe I just came on my stepmother.

I fell to the floor and sat there in disbelief. I can’t believe I just showered with her. It was horrifying but also a little exciting. Even though she caused the most humiliation I’ve ever experienced in my life, she was still a very sexy woman. And I’m a young boy. I can’t help myself. I blame the hormones.

After a few minutes of reflecting on everything, I realized my boner wouldn’t go down. I grabbed it with two fingers and finished myself with the sensual feeling of her touch. The way she handled my penis made me go crazy. In seconds, more flew out and landed on the walls.

I couldn’t understand why I was so turned on. I still had a little boner, and it got smaller every time. Now, it was around 1.5 inches. I decided to think about Mr. Rogers. He was such a wonderful man, making me feel a little desirable. I thought about him looking at my tiny little ding-a-ling.

The fact he looked at it shockingly caused me to erupt in another explosion. I didn’t find him attractive, or did I? I love women, but I’m not sure how I feel right now. It felt good thinking about his powerful body touching mine as he stared at my little penis, tingling and ready for his warm mouth.

I’ve liked women all my life, which was a new feeling. I needed to relax. My boner finally disappeared, and I presented a very small half-inch dicklette that you could barely see. I was a little dry but needed comfort food to relax my mind. I heard nothing and walked into the family room, which led to the kitchen.

When I entered the family room, I was startled to see my clothed mother and her friend Shelley here. Shelley was that woman who invited me to her place at the infamous barbecue. I was charmed by the tight black dress she wore with crimson lipstick.

“Hi, Jake,” Shelley said.

“Oh, hello.”

My stepmom looked at me with disappointment, and Shelley unashamedly looked at my little, skinny shrunken penis. What was she doing here?

“Jake, Shelley came by because you haven’t visited her place yet. She was worried.”

I can’t believe she showed up like this. I just wanted to avoid it entirely.

“I’m really sorry, ma’am. I just forgot.”

“You should have told me, Jake.” She looked at Shelley. “Don’t blame my little forgetful boy here. I had him working hard all day in the front yard.”

“Awww. Jake was working hard? But he’s such a fragile little flower. That is just so cute. And I’m not upset with him. I was just a little worried, that’s all. He seemed enthusiastic about seeing my place last week.”

Yeah, it was the only way to make you stop talking about my little dick right in front of me at the barbecue.

“Well, I am a little busy today,” I said.

“Doing what, Jake? I have nothing else for you to do, and you are all nice and clean.” She tapped Shelley and said, “He just showered, if you couldn’t tell.”

“Ahh, so that’s why he’s all wet, and umm, well” —

“Tiny,” my stepmom shouted.

They both giggled, and I felt embarrassed.

“Mom, don’t say that.”

“Oh, relax, Jake. Shelley has seen that cute little body of yours.”

“Oh, Jake, don’t mind your Mom. She’s just teasing you. We gals are aware little boy parts shrink when they are cold. It’s nothing personal. It’s just how men are built.”

“I’m not embarrassed at all. Why would I be? I’m a proud nudist.”

I held my hips with stature. They both just looked at my little tiny cock as it snuggly slept between my two peanuts for balls.

“That’s a good boy. Since you aren’t busy, Shelley can give you a ride to her place.”

Can anyone take a hint?!

“Well, actually, I was going to see Mr. Rogers.”

“You aren’t skipping out on your duties at Shelley’s place. You can see that weirdo later.”

I don’t know why my stepmom didn’t want me to see Mr. Rogers.

“Alright, let me just go put some clothes on.”

“Jake, that won’t be necessary.”

She couldn’t have been serious. I would be completely naked for the entire day at someone else’s place. I didn’t argue and just agreed.

“Well then, let’s go cutie.” Shelley playfully said.

She opened the door, and there were way more people outside this time. I walked outside to a few neighbors looking right at me across the street. I looked behind at my stepmom, who smirked as she closed the door. There was no turning back now. I was fully naked, and I was going to stay that way.

The neighbors were giggling and talking to each other, but I couldn’t hear what they were saying, so I pretended to ignore them as I walked to her car. Two mothers, Candy and Tina, were watching their kids play.

Candy shouted, “What the hell? The boy is naked!”

She laughed and said, “Relax. That must be Jake.”

“Who is Jake?”

“He is like the neighborhood nudist. There was apparently a barbecue last week, and he skinny-dipped. Tons of the neighbors were there. Everyone’s been talking about it. God, you are so out of the loop.

They watched the car drive away.

“Alright. Well, that solves that mystery. What about, you know, where is his penis?”

She burst out laughing, “That’s the other mystery, honey.”

“I’m not making fun of him. I really couldn’t find his penis.”

“Haha, it’s there. You have to look really closely to see it. We are too far away to see it. He has an awfully tiny little pee-pee. That’s what people are talking about. They couldn’t believe how tiny his dick was when he skinny-dipped. He actually popped a boner, and it was probably smaller than my pinky.”

“Wow. I couldn’t even see it from here. What a shame.” They watched the car drive away. “I’m surprised he’s so shameless.”

“I know. And Tina squished her thumb and index finger.

“Haha, yes, his winky sure is really small. I can’t believe he’s an adult. My four-year-old son is probably bigger than him.”

“Poor boy. Apparently, he’s going to university in the fall.”

“Well, good for him. He’s rather cute. I’d go for him if it weren’t for his tiny little pecker.”

“Damn, you shameless homewrecker. You must miss your hubby if you actually considered Jake.”

“Well, I haven’t seen him since he was stationed in South America. I need to get some.”

“Yeah, and Jake can perfectly do that for you. Have fun with his little baby carrot.”

“Shut up. I won’t mess with Jake. He’s too tiny to do anything memorable down there.”

They both giggled and wiggled their pinkies.

I just sat in the car as Shelley drove in silence. I felt completely awkward and powerless, knowing this woman controlled everything. She drove me, so she had to take me back. I had no clothes and couldn’t ask anyone else for a ride back. I wasn’t up for explaining why I was naked. And I’m sure they would find the opportunity to make fun of my little penis.

The only one who made me feel better about it was Mr. Rogers. I smiled, thinking about him. I looked down at my little penis squished between my legs. It looked tired and pitiful. Could Mr. Rogers have liked my body? I couldn’t believe how small and childlike my teeny weenie looked. I had a penis fit for a little boy. And everyone knew it.

“You must be so excited to see my place. I can’t wait for you to see it. You’ll have a chance to look over every inch of my palace.”

I felt slightly embarrassed over her “inch” comment, but I was intrigued to see this palace she mentioned.

“A palace?”

“Yes, Jake, I am quite wealthy.”

“Wow. I’ll have to see it to believe it.”

“Yes, Jake. I told you it would be nice for you to be somewhere else. You are always at home. Your Mom can’t be that fun.”

“Haha, well, it’s quite interesting living with her. That’s all I will say.”

“I promised you a big place where you can run around naked with your little ding-a-ling bouncing around. And I don’t ever break my promises.”

“That’s nice, I guess. Thanks. Honestly, I’ve always wanted to live in a mansion or a big house. My Mom’s place is nice, but I could always live in a bigger place, haha.”

“We all want bigger, Jake,” and she glanced at my uncovered micropenis. “So, you’re going to university in the fall, right? Your mother told me.”

“Yes. It’s very close, but I don’t know what I’ll study yet.”

“That’s okay. This stuff takes time to figure out.”

After a few minutes of surface-level conversations about my life, we arrived at her place. It was a beautiful place. Was this woman a millionaire or something? And the next house was far away. We were in isolation here. I was keen and terrified of that fact.

I stepped out of the car, completely distracted by the beautiful site rather than being concerned with my naked body. She walked me in, and I couldn’t help but feel grateful to see her place. It was magnificent.

“Wow, ma’am, your place is gorgeous.”

“Jake, you won’t be calling me that anymore here.”

“What can I call you then?”

“Mistress.” She domineeringly stated.

“Mistress?” I asked with a fearful shake in my voice.

“That’s right.”

She kicked the door behind her and locked it. As she walked to me, she smirked at my naked body. She just looked down at my very tiny little penis.

 

To Be Continued…

 

*This story has been edited with AI to fix spelling, punctuation, formatting errors, & basic grammar, but the narrative and plot have remained the same. Even with the limited editing done here, it doesn’t mean any possible major flaws in this story were fixed (That’s the author’s job). The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech. This story was submitted directly to this website. Thank you so much for sharing your story with us.