Continuing Jake’s Dilemma

By Babydicklover.
Authors Note: 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.

Read Jake’s Dilemma by Willy D. Here.


Continuing Jake’s Dilemma…

It’s been three weeks since my stepmother encountered what I call the skinny dipping incident. I don’t think I can come up with a more horrible moment in my life, and I regret ever swimming naked in that beautiful pool. It’s frustrating because I really enjoyed myself, and my arrogant excitement ruined it. All I had to do was take my swim trunks to the pool if my stepmom showed up. But I didn’t and paid dearly for it.

My stepmom still believes I am a practicing naturist, something I regret ever using as an excuse. I wonder if I told her the truth — how I skinny-dipped because my little penis got off from the warm water jets and how she would react. It might have been better for her to discover her stepson was a little pervert instead of having to prance around completely naked regularly.

I’m sure my stepmom can’t get the naked image of her nude stepson out of her head. Even if I can deduce a plan to get out of this humiliating dilemma, the fact remains: she’s seen my naked body, and I’ll never recover from her knowing how small my penis is. It’s etched in her mind forever, and she will always perceive me as her little boy. All mothers saw this, but my mom had physical evidence to see me as such.

There was no way out of this, and I just needed to accustom myself to this new lifestyle. It wasn’t horrible because I did enjoy being naked. I was slowly getting used to it, but every time I passed by my stepmom, she always mentioned it or giggled every time.

I’ve been in many embarrassing scenarios, like the time she ordered pizza again and requested the delivery from Amy, the girl who saw me naked.

I remember the doorbell of horror rang, and my stepmom said sweetly, “Jake, can you please answer the door? I need to finish cleaning up the backyard.”

I knew she wouldn’t allow me to wear any clothes, but I was determined to get this over with. I walked to the door, completely naked, as my little soft penis bounced around. The door creaked, and I slowly opened it to a smiling Amy looking into my soul. I stood behind it so that she wouldn’t get a good look at my little goods.

She looked startled but amused, “Oh, hey, there, little Jake. How is it going, little guy?”

I did my best to ignore her antics directed at the small size of my penis and continued the conversation.

“I just want the pizza. Here’s your money.”

The exchange was almost complete until my stepmom greeted Amy.

“Oh, hello, Amy. How are you? I hope you are enjoying your summer.”

Like a statue, I did not move from behind the door, but this wasn’t over.

“Well, I’m working for the most part, so it’s OK.”

My stepmom took the pizza, “I’ll take this. Hey, Amy, why don’t you come in for a bit? I’d love to catch up.”

My eyes widened, and I was shocked to my naked core. My imminent fears caused my body to tremble, and it shrunk my baby dick to less than an inch. My stepmom handed me the pizza and threw the door open.

“Oh, Jake, you don’t need to stand behind the door. You know Amy.”

With the pizza in my hands, I couldn’t cover myself — not like my stepmom would have let me do that, regardless. I just needed to swallow my little pride and act like I was unbothered by Amy’s visit. I quickly turned around so Amy only saw my tiny, pale butt, and I walked quickly to the kitchen. Without being discreet, I heard them snicker as my smooth, naked butt jiggled for them. Before, Amy didn’t have a chance to see my naked behind, and it was humiliating knowing this younger girl saw my entire bum.

I felt my cheeks turn red as I placed the pizza in the kitchen. I turned around as Amy and my stepmom sat comfortably, watching me. I turned around, presenting them with my really small, bald dick. It was humiliatingly tiny, and they were getting a good look. Their eyes moved downward to see my little penis. When they saw it, they both squinted. And before I put the pizza down, I was curious about my condition and looked down.

It was pathetically small at less than an inch. It was practically a useless nub deep in my body. I saw a big grin creep on Amy’s face. It took everything in me to avoid covering up my little cock, but I knew if I did, Mom would think I was a sick pervert, and this would be all over.

I heard Amy breathe, “Oh my.” She invited me over with a tinge of seduction in her voice, “Jake, sit near us.”

They both were on the couch, and I deliberately chose to sit in the chair away from it. I was embarrassed knowing this girl had a perfect view of my naked body, and I was happy to cover my ass, but my little, tiny front was wholly exposed.

I sat there awkwardly as they carried out a perfectly normal conversation. I couldn’t believe they quickly had a natural conversation with a naked boy close to them. I saw each one periodically make eye contact with my little penis squished between my even tinier balls. And here’s the thing, if my balls are smaller than my penis, there’s practically nothing there.

They both looked at me, “Hello, earth to Jake.”

I composed myself, “Oh, what?”

Amy giggled, “I was asking you how your summer was.”

“Oh, sorry, my summer is nice. I am not doing too much.”

She smiled at me, “That doesn’t seem true. You seem to enjoy yourself being naked, hehe. This is the second time I’ve seen you naked. You must like it.”

I was startled she would bring up the topic of my nakedness.

I stumbled on my words, “I, uh, yeah, it’s OK, I guess.”

Mom laughed, “Oh, Jake. Don’t be modest.” She looked at Amy, “He loves being naked. He’s a practicing nudist.”

I screeched, “Mom, don’t tell her that.”

“Oh, honey, don’t worry about it. It’s not like she doesn’t have a clue. She’s seen all of you.”

Amy said, “Yeah, Jake. There is nothing to be embarrassed about. I’m not offended by your nudity. I have an 11-year-old brother at home, and he doesn’t look different from you.”

“Yeah, I told him he has nothing to worry about. The truth is, he might be a tad bit embarrassed by his little ding-a-ling.”

My face flushed a new shade of red, and I felt my stomach sink further into my skinny white butt. I couldn’t believe my stepmom had just admitted to Amy how small my penis was and that I was self-conscious about it.

She laughed out loud, “Well, at first, I was quite shocked seeing a naked boy last week, but he is just the cutest. And there’s no reason to be embarrassed by your little ding-a-ling. You are quite a handsome boy, and any girl would be lucky to have you.”

Could they please stop mentioning my ‘little ding-a-ling’ right before me? I wanted this to be over with and lock myself in my room.

“See, Jake, nothing is wrong with your handsome little body, especially your tiny ding-a-ling.”

Amy stood up, “OK, I do need to make more deliveries, but it was great talking to the both of you.”

“OK, please visit again sometime. Jake would love the company.”

She winked at me, “I will definitely keep that in mind. Bye, little Jake.”

She looked at my little penis, giggled, and walked out the door. I heard her raucous laughter as she left.

My mom giggled, too, “Amy is such a kind girl. See, Jake, you don’t need to take it from just me. Amy also thinks there’s nothing wrong with your cute little pee-pee. Now, let’s eat before it gets cold.”

We ate and watched television, and I couldn’t get the thought out of my head; one of my mom’s students had seen me naked twice and was aware of how embarrassed I was by my ridiculously small penis. After I ate, I locked myself in my bedroom, filled with tears. I felt my little dick grow to a stupendous 2.5 inches from the pure humiliation I experienced. I tugged at it with my two fingers until it came all over my chest.

And that incident was only a few days after she first saw me naked. My mom constantly brought up my little penis because she didn’t think it was a problem.

Last week, my mother wanted to go through her photo albums. It was actually lovely to look at old photographs, and then, with horror, I saw where this was going as I saw pictures of the beaches. But they weren’t just any beaches; they were nude beaches in France from when we lived there. I saw photographs of my father with different friends. My father’s size intimated me. If we were both naked, standing side by side, his cock would dwarf mine into nonexistence.

“Oh, wow. I forgot how big your father was.”

Her little comment about my father made me feel bad about my tiny cock because I could have inherited the larger, manlier size of my father’s cock, but left with a very small and bald wee-wee. Mom reminded me of how handsome I was, but no girl would ever desire my little salty peanut, no matter how attractive I was. Then, she reached the section with pictures of me as a naked toddler. I couldn’t believe what I saw. It pained me to admit this, but it was the truth; my little boy penis really didn’t age a day after I turned six.

“Wow. I forgot how adorable you were as a baby boy.”

I doubted how much I had grown, but my stepmom had proof I was still the same size downstairs as a little toddler. Sadly, my little guy looked even bigger when I was a young boy because it was proportional; now, it seemed exceptionally tiny and out of place on a grown man. And even still, with my skinny little body, I didn’t have the most mature appearance. And I could no longer deny I indeed had a slim, six-year-old-sized little pin dick. I just sat there, completely humiliated, as she reminisced and compared my small penis to the ones in the photographs.

She giggled, “Aww, Jake, remember when I laughed at how much fun you were having in the pool? I said you ‘looked exactly as you did when you were six years old — smiling and laughing and running around with your little pee-pee bouncing around.’ It just made me so happy to see you that. You did look happy the other day in the pool, like a little boy. And I know it may have sounded like I said your penis is the same size as when you were a little toddler, but clearly, that isn’t the case.” She looked at my shriveled, little penis and then the photograph, “You’ve grown, most definitely. See…”

She shoved the photograph in my face. The countless small penis reminders defeated me, and I couldn’t help myself but laugh at the sheer ridiculousness of her lie.

“What do you mean, mom? It looks the same.”

“Yeah, that is true; I didn’t want to hurt your feelings. Boys your age can be sensitive about their little parts, and you’ve expressed to me how insecure you feel about your small wee-wee.”

I don’t know why I said that; it was a reflex. But it was horrifying hearing how my little toddler dick hasn’t changed. I could acknowledge it, which was bad enough, but did my mom have to share this with me blatantly? She didn’t have to tell me; I could clearly see I was the same size. I’m the one with the very small thimble for a pee-pee, not her.

She saw my face glow bright red and comforted me, “Aww, no, Jake, honey, as I’ve said, you are lucky to have this body. It is nice, and there is nothing wrong with having a tiny package. Many women prefer small and smooth, anyway.”

Oh my god, not this again.

I couldn’t believe her right now. There was a difference between being small and having what I have. I barely had anything between my legs, and she knew it. I don’t understand why she wanted to keep pointing it out. It was known between us my penis was incredibly tiny.

Every time she giggled, it wasn’t out of innocence; it sounded like amusement. How was she amused by laughing at my very tiny, miniscule penis? Didn’t she feel any empathy for me? She flipped back to an image of my father and stared at his prominent, dangling member.

“Wow, I don’t miss many things about your father, but I do miss his big weenie. He loved being naked, when he would walk around with his big one swaying across his hips.” She saw how I looked uncomfortable, “Oh, never mind, sweetie.”

I stammered, “Mom… umm. It’s fine.”

“No, it’s not. That’s very inappropriate of me. I miss being with someone. Your father did pleasure me in ways I can’t even fathom now. I tingle just thinking about it, oh there I go again.”

I felt like weeping, “I will never be able to make a girl feel that way.”

“Oh honey, that’s not true at all. It’s not about the size or the girth; it’s about how you use it. You could pleasure any woman like your father could do for me.”

I appreciated her trying to make me feel better about my teenie weenie, but it made me feel worse because she and I both knew that wasn’t true. I sat there looking down at my pitiful, tiny weenie as she flipped through the pages.

She gasped at a page, “Oh wow, look at these.”

I saw the pages, and it was her as a young woman, naked, with my father.

“Oh, wow, mom, those are very nice.”

Seeing my mother with her smooth, young body shamefully turned me on. With my naked father, I imagined how much he plainly pleasured her, and pretty soon, my little pecker rose to a very tiny boner.

She turned and said, “Thank you, honey, I can’t believe” —

She looked right at my baby boner with an astounded smile.

“See, yours can grow just fine.”

I looked down, shrieked, and covered my 2.5-inch boner with both hands.

“Mom, I am so sorry.”

“Oh, son, it’s completely natural. You don’t have to cover it.”

I let go, and it sprang up inches from her curious face. Now, she saw it in every precise detail. She saw the short shaft, half the size of her thin pinky. A woman could gain more pleasure from half their pinky than I could ever accomplish.

“I’m curious. What caused this sudden growth? It wasn’t from me. I can’t imagine my sweet boy lusting after his stepmom; I mean, that’s sick.”

I panicked, “No, no, not at all. I was, umm. I honestly thought about being at a nude beach and seeing the girls there. It just got me a little excited, you know, having them see me naked.”

“Oh, you were imagining girls seeing your little thing. Yeah, that’ll do that to a boy like you. If you want to, we can go to a nude beach. It sounds like fun.”

I was praying she was joking, but that probably wouldn’t be the case. I can’t imagine showing random strangers my naked body. My little penis would be so small from the cold breeze.

“I’m going to finish dinner. Why don’t you take care of that?”

“What?” I asked confusingly.

“Oh, I mean, your, hehe, boner. There is nothing wrong with masturbation. It’s normal for a boy your age.”

“Mom, stop talking about it.”

“Oh, Jakey boy, don’t be so antsy about it. It’s part of being a naturist. You may get unplanned boners. This is how you deal with it.”

Without hesitation, she grabbed my little child-sized boner with two fingers and stretched it slowly. I couldn’t believe my stepmom was touching my small erect penis.

“See what I mean?”

“Yes, I do. Thanks. I’m going to go no” —

“Now, you try.”


“I want you to try. You need to know the proper technique, or you could aggravate your little dinky.”

I couldn’t believe I was doing this, but I reluctantly grabbed my hard dicklette and jerked off. She smiled at me as I pleasured myself. I watched my stepmom’s sexy chest, and I couldn’t contain myself. My little penis exploded right in front of my stepmom. Clumps of cum flew from my little wee-wee and landed on my stomach.

I can’t believe my stepmom just saw my little penis cum.

She looked pleased with herself.

“That’s a good boy. I’ll cook dinner, and you can go to your room to clean yourself up. I know you have toilet paper in there for this occasion.”

“Sounds like a plan,” I said.

I ran to my room with my little twinkle bobbing back and forth in tears. I was crying into my pillow, thinking about how good it felt for my stepmom to play with my small penis. I was such a sick boy, and I couldn’t believe the sexual thoughts I had. It grew again and pulsated at the thought of my stepmom watching me play with myself.

I aggressively masturbated, thinking about my naked stepmom and even about going to the nude beach together. She would relentlessly mention the small size of my wee-wee with other girls around, like Amy. I came in a matter of seconds. I cried even harder, knowing I had just cum again to the woman who raised me. I looked down, and it was a little innie, which I covered with my blankets out of shame and humiliation.

With all these humiliating dilemmas, pretty soon, I became desensitized to the tiny dick references my mom would conjure. I actually enjoyed being naked, and I had no problem with it. My stepmom seemed bothered by this and was annoyed with me. I didn’t understand her frustration with me.

I felt self-assured, parading around naked with my little cock wiggling in front of my stepmother like a small boy. I finally felt free and unbothered by my impossibly little wee-wee.

My stepmother told me she wanted a barbecue, and I needed to pick some things up from the local market. I hated wearing clothes now, but I couldn’t walk around exposing my little pinkie in public.

“Jake, make sure you wear clothes. You don’t want the girls seeing your little pee-pee, now do you?”

My mom set me off on a big adventure, going to several stores and buying frozen shrimp, cocktail weenies, baby carrots, and many other items. After two hours, I returned home to several cars in the driveway.

What was going on?

I entered the house with the groceries. Outside, there were several neighbors and family members — including my Aunt Jackie and her husband, Carl. There were a total of 15 people, which was exciting. I loved living in this neighborhood. We lived in a smaller community, so everyone knew one another. I didn’t realize she invited anyone over. As long as I didn’t have to be naked in front of them, this would be fun.

I walked outside, calling for my mom, “Hey, mom. I’m back.”

She walked to me, “Yay, thank you so much, Jakey. You are such a good boy.”

I didn’t understand why she was in a friendlier mood than before. It was probably from the guests she had to be nice to.

“This is great. I’m going to lie all this outside for everyone.”

“Great, I will be right back.”

I sprinted to my room and stripped down. I picked up my swim trunks and put them on. I haven’t worn these in a while. I looked at my naked body in the mirror.

Imagine if everyone saw my insanely small penis? I’m glad that would never happen.

I walked down the hallway to the backyard. My mother already had a beautiful assortment of the snacks I bought. I walked outside. Everyone seemed ecstatic to see me. I was about to jump in before my mom interrupted me.

“Jake, wait, aren’t you forgetting something?”

“I don’t think so,” I claimed.

She gave me a gorgeous, infectious smile, “You are allowed to practice your nudist lifestyle here. You should know that by now, silly boy.”

I looked horrified. What does she mean, certainty not in front of all these people?

She noticed my unbelieving demeanor.

“Oh, I already ran it by them. They don’t mind you being naked,” she reassured me.

All of them nodded in agreement.

My Uncle Carl said, “Yeah, Jake, we don’t mind. Nudity is a beautiful thing.”

Another neighbor, Shelley, an older woman, said, “Yeah, Jake, just get naked. We won’t judge you.”

I glared at my stepmom with a sort of ‘Are you crazy?’ look, but she looked unfazed. She looked at me with an accepting but devious smile. Everyone looked at me patiently, waiting for me to strip naked. The energy in the air was peaceful, but my heart was racing.

What was my stepmom thinking, making me naked in front of everyone?

It was embarrassing enough to be naked with my stepmom, and I was finally over that, but being nude in front of the small neighborhood was mortifying. Not every neighbor was here, but I’m sure the news of Jakey boy’s little bald penis would travel like a widespread disease. And I couldn’t do anything about it. I still had to play the part of an active nudist.

I couldn’t believe I was about to do this, but what choice did I have? I was in too deep to leave now. I grabbed the waistband of my swim trunks and slowly lowered them. As my little privates bounced out in the open, I felt the cool air wrap around me. I knew my little penis was laid-out, and I continued until I was completely naked. I brought them down to my skinny ankles, and I stepped out of them, throwing them on the chaise. I tried to avoid eye contact with anyone.

Frequently, in movies, when a man is naked, they film it from an angle, showing people between the guy’s legs. That’s exactly how this felt. There I was, completely naked, in front of several neighbors and family members, all eyeing my very small penis. The outside was quiet, not even a chirp from the birds — even they knew not to shatter this priceless moment.

All of them looked initially shocked upon seeing my bald baby dick, and some of them found it quite challenging to remain stoic. They tried not to laugh or snicker at my little display, but I heard a few giggles disguised as coughs.

Oh my god, they’ve all seen what little I have between my legs. And some were even laughing. It was over for me.

I felt every innate urge in my body to cover my very tiny penis, but I couldn’t do that. After revealing myself to everyone, I ran for the pool, fully naked. They all watched my little soft penis bounce around until a strong sense of deja vu hit me.

“Jake, aren’t you forgetting something?”

Not this again, the damn suntan lotion.

“Yes, mom. I’m coming.”

“I want you to thank everyone individually for coming today.”

I couldn’t believe my stepmom was making me do this. I walked up to everyone and thanked each person for attending the barbecue. Their eyes were fixed on my little penis as it just stood there looking incredibly tiny and useless. They could see every humiliating detail of how it was a skinny white, mini one-inch excuse for a penis.

“Now, for the suntan lotion.”

I knew better than to argue with her. And I couldn’t stop thinking about what everyone thought about my body. This was the worst day of my life. I turned around, giving the audience a look at my pale little butt, walking with defeat to my stepmom.

Monica, Aunt Jackie’s sister, exclaimed, “Oh my. What a cute derrière,” causing everyone to giggle lightly.

It was embarrassing knowing everyone had a view of my entire bare butt.

She handed me the suntan lotion, “Here, you can do it this time.”

There was a relief knowing I could rub the suntan lotion on myself rather than my stepmother. I didn’t want to pop a very small boner in front of all these people. Everyone was chatting, which made me feel better not to be the center of attention, but everyone was still looking at me.

I rubbed the lotion all over my body, and people couldn’t help but giggle at my naked body. I shivered as I ran my hands down my legs, my arms, my stomach, and my butt.

I was finished when Shelley said, “Wait, Jake, you forgot your little ding-a-ling. You don’t want a burn down there.”

She just said my ding-a-ling was little in front of everyone. Now, the nomenclature was established and accepted. I squeezed out more and gently rubbed my small penis smoothly and sensually. I finally finished before I felt my dick grow, but I jumped in before that could happen. I was grateful to have some cover, but people reminded me how brave I was to be naked in front of everyone.

My Aunt Jackie said, “I admire your confidence. I would be horrified, just horrified, to be naked in front of my family. But it’s great you don’t care about people seeing your little ding-a-ling.”

That term was used several times, making me very self-conscious, like under a microscope. At some point, since I was covered, I didn’t mind being naked. There were five other people in the pool. I didn’t want to be near them, but my Uncle Carl jumped in. He stayed a little close to me, forcing me to move towards the water jets.

Oh no, not the water jets. I can’t be aroused in front of all these people. What am I going to do?

I couldn’t leave because my uncle was in a serious conversation with me about his new truck. I felt the water jet’s warm, intense blasts over my sensitive crotch, and it was too much. I rolled my eyes behind my head as my little boy’s cock grew to a tragic small-scaled boner. I finally moved away from my uncle so I could relax, hoping my boner would go down. I tried my very best until my stepmom called me.

“Jake, can you grill the ribs? Everyone is getting hungry.”

This couldn’t be happening to me. I still had a raging tiny boner.

“Actually, I’m having a good time here. Can’t this wait?”

“Jake, get your naked butt out of there, mister. We have guests.”

Great, I was trapped again, and this time, it would be worse. I swam to the infamous stairs. I picked myself up and climbed. I wanted to cover my small boner desperately, but I couldn’t. There I was, soaking wet, utterly naked, with a hard little baby dick. It sprang to a 45-degree angle, showing everyone how small I genuinely was.

I heard loud gasps and saw mouths open with my peripheral vision as I walked to the grill, with my hard boner barely moving. I swear, in the background, I heard laughter.

And when I turned around, I saw people talking amongst themselves, but some of them gave the small penis symbol or stuck their pinkies out to each other. My little penis was the primary topic of discussion, and I never felt more humiliated. I felt my excited needle erect dick die down. At least one dilemma was resolved.

Shelley came up to me.

“Hey Jake, do you need any help?”

“Nope, I think I’m fine.”

“I want to apologize for saying ‘little ding-a-ling.’ I didn’t mean anything by it. It’s incredibly endearing.”

“That’s OK, I’m happy with my body.”

“What a very good attitude to have.”

I couldn’t help but notice she was staring right at my little mushroom-like crotch.

She whispered, “Jake, boy, you should pull it out or something.”

I looked at her, confused, “What do you mean?”


I saw her gaping eyes positioned towards my crotch. I followed her lead and looked down.

My eyes widened. Oh my god!

I had significant shrinkage, and I practically had no dick. There was nothing there. I quickly touched it and pulled it out, so it was half an inch at least. I looked at Marcus, who smiled at me with a smirk, saying, ‘Yep, I’ve seen the little thing at its smallest, and there’s nothing you can do about it.’

Everyone saw me at my smallest and, quote on quote, biggest.

“I just want to say I think you are courageous to be a practicing nudist and do it in front of everyone.”

“I don’t get it. What’s so brave about what I’m doing?”

“Oh, nothing, it’s just, I’m sure you realize that you know…”


“C’mon boy, you know your dick is super duper tiny. And that little thing has everyone’s attention. We were all talking about it right after you started grilling the ribs. Surely, you know that.”

I couldn’t believe my neighbor openly said my penis was incredibly small and had everyone’s attention.

“Yes, but my stepmom says it’s no big deal.”

“Well, yeah, she is correct, haha. But I think you are fearless in doing that. If my dick were that tiny, I wouldn’t have the confidence to show it off like you are. It’s like a small doorbell.”

I was committed to being a nudist and said, “There is nothing wrong with having a small ding-a-ling. The human body is beautiful.”

She laughed at the absurdity of my defense, “Oh, of course it is, cutie pie.”

My stepmom joined us, “Hey there, how’s my little Jakey Wakey?”

Marcus giggled at her infantilizing and baby-talking to me.

“He is just so cute and short.”

Shelley argued, “But, he’s not exactly short.”

She looked down at me, “Oh, then that’s not what I meant, hehe.”

They both giggled.

“My little man is so cute. Emphasis on little.”

She skipped away, making me feel even more humiliated and emasculated by just admitting to our masculine neighbor how small I was.

She whispered in my ear, “You know if you want a change of pace from your stepmother, you can always come to my place.”

“Oh, that would be” —

“I have a big house and backyard. You haven’t been to it, but it’s also pretty isolated.”

“I don’t know, I think here is OK and” —

“There’s a nice lake you can skinny dip in. All to yourself. We can skinny dip together.”

“I don’t think that is a good idea because” —

“You’ll have a wide open space to run around naked with your little ding-a-ling. Doesn’t that sound fun?”

“Yeah, I guess it—”

“I’d love to watch your tiny pee-pee excitedly jiggle for me as I smoke a cigar with my feet up. You’ll get to be the cutest little boy you truly are. I also have some chores you can do. So, I’ll see you at my place next Saturday?”

Her dominant voice left no room to debate in this agreement, so I gulped, “OK, that sounds good.”

She rubbed my head and winked, “That’s a good boy. Just make sure you bring your adorable little winky.”

Did I accept a date from my neighbor, or was it a fun time to just run around naked? I didn’t know, and I was scared to find out.

“Jake,” my stepmother called. “I need you to serve the snacks.”

“OK, the ribs are basically done.”

I grabbed the assortment and took the tray to everyone. It had baby carrots, grapes, shrimp, and cocktail weenies.

One of the women grabbed the cocktail weenie, “I just love these really small things. So tiny and small, but full of juicy flavor.”

Aunt Jackie responded, “Haha, I’ve never been full from them, though. They just aren’t big enough.”

“I’ll take a very small baby carrot. These are really good.”

I knew exactly what they were referring to, making him even more embarrassed. After serving snacks, I finally swam in the pool peacefully.

My Uncle Carl frowned, “It’s not fair. Why does only Jake get to be naked with his little ding-a-ling? Why don’t I get that privilege?”

“I mean, no one said you couldn’t. Everyone is welcome,” my stepmom responded with enthusiasm.

He stripped himself and shouted, “Hell yeah.”

My mouth was wide open when I saw the hog between his legs. It made me feel even tinier and less significant. He confidently showed his off and had a valid reason to. I did not, and our cocks illustrated the stark contrast between a man and a boy. We both got out of the pool, and the difference between our cocks was astronomical.

My stepmom asked for my help again setting the table.

She told me, “Your Uncle Carl is so big and strong. Don’t worry, Jake, you’ll grow up to be like him.”

That is so stupid and outrageous. I’m finished growing with just a little thimble.

Everyone left the pool and ate while I sat there with my small ding-a-ling displayed. They probably all questioned how I could be so underdeveloped and prepubescent looking. After a few hours of more banter and subtle hints about my teenie weenie status, everyone finally went home.

As we cleaned up, my stepmom asked, “Wasn’t that fun?”

“Yes, that was fun.”

“See, no one cared about your little ding-a-ling. They all thought it was very cute. And great, I’m glad you think so.”

I looked at her with terror, “Why?”

“Because we should host more of these. Next time, I might invite some of my students. They’d love to meet you.”

This couldn’t be happening.

And again, Jake was incredibly humiliated and embarrassed that his little small penis was exposed to several people he knew, and maybe even more shortly because he continued playing the ruse; he was a nudist, and now, he could never escape it. What did his stepmom have planned? And what did his neighbor invite him to? There are too many dilemmas Jake will soon be facing.


The End?


*This story has been edited 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.


  • SphEnjoyer

    Loved the story hope to see what happens to Jake with his neighboor

  • ryan

    I hope you are going to continue Jake’s dilemma?!! You are such an excellent writer!!!

    • Babydicklover

      Absolutely, I will! Stay tuned!

      • Bdlfan

        His mom should invite her co-workers over… (Other teachers, which will of course include Jake’s attractive female teachers, especially the ones that don’t like him, revenge SPH is great.)


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