Jake’s Final Dilemma

By Babydicklover.


Jake’s Dilemma by Willy D..
Jake’s Dilemma – Mom’s POV by TPK.
Continuing Jake’s Dilemma by Babydicklover
Jake’s Next Dilemma by Babydicklover
Another Dilemma in Jake’s Life by Babydicklover

*****

Jake’s Final Dilemma…

It’s been a month since I saw Shelley. I felt like a completely different person. While I gave her audience the most embarrassing performance of my life, I finally felt confident about my appearance. She sent me the photos from the evening, and it was shocking, to say the least. I gave those women quite the thrill, which made me honored. My penis was pathetically smaller than almost every man’s, and they made sure I knew that, but that didn’t matter to me anymore. I couldn’t change how I was born.

I was in bed naked like I always was nowadays and looked under the covers. Usually, I’d squirm at how small and embarrassing my little penis was. But I was proud of my “Mighty Millimeter Peter.” With everything I’ve been through, I don’t think anything could shake me. I looked at my body in the mirror as I finished my morning routine.

“Damn, that is tiny.” I laughed to myself, the sound hollow in the empty room.

Without a shred of hesitation, I strolled through the living room completely naked, not a care in the world. Today was special — my birthday, and I would make the most of it.

I walked in the backyard to my stepmother, lounging by the pool.

Good morning, Jake,” she greeted me, her eyes immediately dropping to my little soft penis bouncing around as I moved.

“Hi, Mom!” I said, trying to keep my mood light. She smiled subtly but looked back down at her magazine.

“Are we doing anything today?” I asked, hopeful.

She looked confused and said, “Why, it’s not like today is any different than normal.” My face fell, but then she chuckled. “Got you! Happy birthday, sweetie.” A smile crept onto my face as she kissed my forehead. “Happy 19th birthday.”

“Thank you, mom. I’m so happy you remembered.”

“Don’t be silly. And yes, we are doing something. I wanted to take you to this gorgeous beach I’ve been reading about.”

My face lit up, assuming it was a regular beach, but I still preferred the privacy of my backyard for my nudity.

“Awesome! I can’t wait.”

I sat beside her, feeling the warm August sun on my skin, especially on my little cock.

“We’ll leave in about an hour. You should get ready now.”

“C’mon, mom. I just sat down.”

“There’ll be plenty of time to relax, Jakey.”

“Just a few more minutes.” I closed my eyes, enjoying the warm breeze.

I heard her go back inside, leaving me alone. I walked to the pool and started swimming, the water jets providing a comforting massage on my bare buttocks. I turned around, letting the jets vibrate against my nether regions, a loud groan escaping me. I checked if anyone was watching, but I was alone. My mind wandered to those women watching my naked body, their laughter humiliating yet strangely arousing. I could imagine they wanted me.

In my fantasy, each woman would give me a blow job, marveling at my minuscule cock, their passion for my little grape intense, rejecting men with big cocks for my small one. Each time I finished, my penis shrank further, becoming a pathetic little nub incapable of fitting into anyone’s mouth. And there it was, my small penis stretched completely, thrusting with white cum exiting the urethra, mixing with the pool water. I felt a twisted satisfaction.

I hopped out of the pool, my still-hard cock feeling sensitive and tiny, quickly retreating into its shell as I went back inside.

“Hurry up, Jake,” my stepmother said, seeing me soaking wet and shriveled up between the legs. “We have plenty of time to swim later. Get you and your little ding-a-ling ready. I want to beat the traffic.”

Hurriedly, I packed everything I needed. I was happy I could be clothed again, as I hadn’t been in a while. After a suspiciously long drive, we finally reached the beach, but you needed to hike a few miles to get it.

“Mom, why is this such a long hike?” I complained with sweat dripping down my face.

“It isn’t so bad. You’re a young and healthy boy. You can handle it. Besides, you’ll love it when we get there.”

We walked on the long trail past green grass and beautiful flowers. I was very hot and sweaty, but it was a peaceful walk, and we reached our destination before I knew it. As my feet touched the sand, I knew why my stepmother brought me here. There was a nude man in the distance.

“Mom, this is a nude beach!” I shrieked, panic rising.

“So what? You love being nude. This is perfect for you.”

I didn’t want to be nude in public, as anyone could see me. The beach was completely packed, and hardly anyone was nude. I saw a few men and maybe one woman nude.

We dropped our things on the floor and set down our towels. I collapsed on the towel, stretching my body out, hoping my stepmother would drop it.

“Jake, are you not going to get nude? It’s fine. This is a nude beach. No one will care.”

I looked at her, squinting from the sun blasting in my face.

“I don’t know. There’s a lot of people here.”

“I see. And you don’t want them seeing your little ding-a-ling, huh?”

I started to feel self-conscious again being nude with all these clothed strangers. My confidence was slipping.

“Yeah, I don’t think I’m ready to take my nudism that far.”

She smiled and looked at the few nude people in the far-out water.

“Well, I’ll tell you what. I’ll take my top off if you get nude.”

“Wait, why?” I couldn’t believe she wanted me to get nude this much, even to expose her small chest. She was insecure about that area of hers, even though I’ve told her it was lovely many times.

“Because I want you to feel comfortable.”

“Okay.” I agreed to her ridiculous suggestion, but I was dying inside.

I can’t believe I was doing this — to be nude in front of all these people. I was very nervous. I looked at my stepmother, and she took no time because her chest was already wholly exposed. I slowly took my shirt off and removed my swimsuit. Looking around, I slid down my white briefs to my ankles so I was fully naked. My stepmother looked right at my penis, and her eyes were enlarged. I know it was small, but I couldn’t do anything about my dilemma again.

“See, Jake. Don’t you feel good?” I just nodded to her. “No one cares how small and bald your penis is — like they don’t care about my little boobies.”

Her attempt to comfort me didn’t work; it also confirmed what others would be thinking.

“Yeah, but mom, people care more about penis size than breast size.”

“Oh, pish posh, Jakey, that’s just silly. You have a very handsome body. Your little ding-a-ling is very cute.”

It may have sounded silly to her or any woman, but men knew that wasn’t the case. Her entire nipple was bigger than my soft little boy-sized penis. Sure, my hard cock could compete with her nipple by an inch or two, but her pinky finger was still longer and thicker than what I was packing.

I felt humiliated and just wanted to cover up. A few people looked at me but continued their day like it was nothing, which made me feel a little more comfortable. I did receive a few smirks, but they were quickly ignorable. After an hour of feeling the bright sun on my back, two older ladies, Lori and Angela, started conversing with my stepmother.

“Yes, make sure you use the Vitamin C serum if you want it to glow more.”

Their conversation was a complete bore until one of them addressed me.

“So, who is this cute guy?” Is this your husband?” Lori asked.

“Haha, no, that’s my stepson.”

“Oh! Awkward.” Angela laughed.

“It’s his 19th birthday today.”

“Awww. That is so sweet. Happy birthday. He’s quite cute.” Lori said, followed by Angela nodding.

I blushed at their sweet remarks. They felt like a sincere pair of old ladies.

“Really?” I asked them.

“Oh honey, yes. You’re one of the only dudes out here in the nude. You’ve nailed the confidence. I wish I could do that.”

Angela said, “Yeah, you’ve got the cutest bahookie.”

I looked confused, to which Lori explained. “Oh, it’s not exactly a common term here. We are from Scotland. It means the butt.” This made me blush even more to see these women complimenting my smooth bare butt. I was lying on my stomach, so they got a full view of it.

“Well, what’s stopping you ladies from joining me?” I asked them with a smirk.

“We are a little insecure. I can’t imagine being nude.”

“Well, I think you should try it,” I told them.

“If you go to the water with us, we can be slightly covered.”

“It’s a deal. I haven’t even been in the water yet.”

I wanted to avoid going into the cold water because of the inevitable end most men fear. But these ladies seemed very fun, so I didn’t care. They both removed their swimsuits, exposing their old sagging breasts. They untitled and lowered their bottom pieces, leaving them naked.

“Last one’s a rotten egg,” Lori shouted.

They started running, albeit slowly, toward the water. I stood up and chased after them. I zoomed past them and fell into the cold water.

“That feels nice,” I said as I waved them over.

They finally caught up and shivered from the freezing water.

“You know, with it being so hot out, you’d think the water would be warm.”

“You’ll get used to it.” I laughed.

Lori splashed Angela, and sooner than ever, we were in the middle of a splashing fight. I was still swimming in the water, but I got a few splashes on their breasts, which was my target.

“I haven’t played like this since I was a little girl,” Angela uttered.

Angela agreed, and I stood up, looking at the peaceful waves.

“Thank you so much, Jake, for encouraging us to do this. We owe you one.”

“You’re welcome.”

I turned around, presenting my entire front to them. They had little glimpses during the splashing fight, but it was crystal clear now. I looked for my stepmother in the distance, but she wasn’t there. I shrugged and watched the beachgoers.

Lori didn’t want to miss this opportunity, so she looked between my legs and was utterly shocked.

“Wow, yeah. Jake, you are, shall I say, confident.” She stammered from her astonished demeanor.

I didn’t notice her close gaze as I was distracted by the bountiful peace. Lori looked at Angela, her mouth wide open like she had just heard the juiciest gossip ever. Angela looked at my little cold cock. Her face turned bright red, and she felt embarrassed for me.

“Jake, you are, shall I say, confident.” She stammered.

And they both started laughing innocently. I didn’t understand what that meant, so I smiled at them. I held my hands on my hips like a general, and they couldn’t believe how small my penis was. It just wiggled around every time I moved. It was hilarious, but they didn’t want to laugh in my face. They both got closer to each other.

“How is it even possible to have a dick that small?” Lori whispered.

“I don’t know. I feel secondhand embarrassment just looking at it. Poor guy.”

“There isn’t anything there. I know shrinkage is real, but I didn’t know it could make it disappear.” She covered her mouth and chuckled.

Initially feeling sorry for Jake, Angela now joined in as they joked about my little teeny weenie.

“And it’s completely hairless. I wonder if he shaves it.”

“But why?”

“So, you can see it, I guess. You know, so that it won’t hide in the bush.”

“I get that, but it didn’t make any difference — I can hardly see it now.”

“Well, maybe he’s a grower.”

“Any size, and he’ll be a grower since there’s nothing there.”

“It’s there, it’s just incredibly tiny.”

“I think it’s adorable.”

“He’s like a little boy.”

Right? How is he 19? That sucks.”

They stopped whispering, and Lori asked Jake if has ever been with a girl.

“Honestly, I haven’t.”

“I can see that,” Angela whispered.

I’m trying to find the right girl.”

“That will be quite hard,” Lori whispered back.

“Well, I’m sure you’ll find one sooner than you think,” Lori told Jake.

I saw my stepmom sit back down now, but she had her top back on. She waved to me.

I waved back and said, “We should get back.”

And we all walked back. The walk back gave the beachgoers a unique show. Several of them looked surprised as I walked past them. I didn’t notice because I was having a great time. But most people couldn’t help but laugh to themselves.

“Jakey, how was the water?”

“It was very nice.” The two agreed. “And it was pretty cold.”

This caused both of the old ladies to erupt a barrel of laughs. My stepmom knew why they were laughing as she was looking at my little tiny penis now.

“Yes, your stepson is lovely. And his confidence is charming.”

“Aww, yes. He’s a very good boy! I tell him any girl would be lucky to have him.”

“Well, it was nice meeting you two, especially you, little Jake.”

They both quickly put their swimsuit outfits back and walked away laughing loudly. They couldn’t hold it in anymore. In his heart, Jake knew precisely why they were laughing the whole time, but he didn’t want to acknowledge it.

“But anyway, I have a surprise for you.”

She held my hand and walked me to the other side of the beach. A few tables with food and sweets were at the corner of the beach. I recognized a few faces, but I must have been seeing things. The closer we got, the more afraid I became. We got there, and around 100 shouted, “Surprise!”

I couldn’t believe my eyes. Almost everyone I knew was looking right at me. Each person was clothed entirely, so I felt even more exposed. I couldn’t help myself, but I let go of my stepmother’s hand and covered my very small penis with both hands. This caused everyone to laugh sympathetically. I have never felt more embarrassed in my life.

“Mom, what’s going on?”

“Oh, honey. Relax.” She swatted at my hands, making me expose my little penis to this personal audience. “It’s your surprise party. Did you think your 19th was going to be uncelebrated?”

Everyone I knew was here: students from my stepmom’s class, Aunt Jackie holding a video camera with her husband, Shelley, and her husband, the entire neighborhood with Mr. Rogers, distant members of my stepmom’s family, and even my father.

“Jake, don’t just stand there; say something.” My stepmom urged.

“Umm. Hi everyone. It’s nice to see you.” I let out awkwardly.

“Oh, Jake. Sorry, everyone. He’s a little shy about surprises. And to tell you the truth, he’s probably self-conscious about his little ding-a-ling.” Everyone looked down at my almost non-existent penis and started awkwardly laughing. I felt so exposed and embarrassed. Every pair of eyes glued to the little pimple between his thighs. I couldn’t do anything. I was trapped. They tried to act like it was a laughter of silliness, not ridicule, but I knew better. “Haha, yes. He is cute, I know.”

That wasn’t the reason they were entertained. Jake knew it was because he was born with such a small penis. Some were clutching their sides, trying hard to shield their laughter. It felt like a nightmare. Just a few hours ago, I felt confident and relaxed. Now, I felt even more embarrassed than the first time I swam naked in that pool. All this madness stemmed from that ridiculous day — even today, I indulged in my perversion. That was partially why it was even more tiny than usual.

In front of everyone, my little tiny half-inch cock was presented. And my stepmother confirmed I was self-conscious about it. Everyone could have ignored the size, but it was common knowledge now, just like when the neighborhood saw me at that pool party. I don’t know if it was my stepmother’s mission to humiliate me or if she secretly knew about my perverted fantasies and was punishing me. The worst part was it was working perfectly. No matter what, everyone now always would realize I had an impossibly small little bald ding-a-ling. The humiliation was palpable. My tiny little member was not just small; it was so disproportionately tiny that it made the average one feel blessed and endowed.

To interrupt the awkwardness, my father approached me and shook my hand.

“Jake, happy birthday.” He said with a hug.

I hadn’t seen my father in a few years since he decided to stay in France. My stepmother didn’t associate with him but wanted him there for my special day. He looked at my little cock and just smiled.

While I was embarrassed after my father greeted me, so did everyone else. A few of them even got nude. All the men were starkly bigger than me, which made me feel worse. Even the men with smaller cocks dwarfed his size completely. They may have been small but weren’t “Jake” small.

I’ve never seen a man look more content knowing their smaller cock was finally bigger than someone’s. This stung the most even more than any girl’s laughter. Even smaller men, who know how it feels, were more hung and joined in on the teasing. They finally felt free and found solace in their size. They enjoyed the attention off of their little members, each wiggling around as they giggled about Jake’s.

It was a hard reminder of my little condition, but it felt better because everyone was here to celebrate with me. I knew the girls from my mother’s class would spread the news like wildfire, but I tried to ignore the reality of what could come. We were all eating and enjoying each other’s company.

A few of them swam in the water. My father came up to me, this time naked. Like the photos I’ve seen, his cock was huge and swung around. His beautiful body was glistening.

“It is nice to see you, Jake.”

“Yes, Dad, it is.”

“Can I talk to you for a moment?”

I looked at the other guests and smiled.

“Sure, Dad.”

We walked toward the calming water.

“It’s been a while since I’ve last seen you. It’s good to see you are adjusting well with your stepmother.”

“Yeah, it’s been quite a journey.”

He cut to the chase and said the worst thing he could. He looked down at me.

“So, son, honestly, that’s a tiny ass dick.”

I turned bright red and said, “Yes, I know.”

“Aren’t you embarrassed to be parading naked with that little thing?”

I had no other choice but to lie.

“No, not at all. You’re the one who taught me there’s nothing wrong with nudity. I’m just living that down.”

My confidence took him aback.

“Yes, that is true, son. I didn’t say you should be ashamed or anything. I would be embarrassed if I had your size, that’s all.”

“I get it, Dad. Did you just come here to make me feel worse?”

“No, sorry. I’m not saying this right. I just don’t remember the last time I saw you naked. And I was just curious why it was so small when you know…” He swung his big cock back and forth.

“Yes, I’m aware.”

“Jake, I’m proud of you. And honestly, I’m a bit jealous.”

“What? Why?”

“I’m jealous of your… your little penis.”

“What do you mean?”

“When people see me naked, they immediately desire me. I expect to be a big and strong alpha male type, you know? That just isn’t the case for you.”

“And you’re saying that’s a good thing?”

He paused, a chuckle escaping him before he caught himself and turned it into a sigh. “In a twisted way, yes. You’re free from that. No one expects anything from you in that department because, well, let’s face it,” he gestured towards Jake, his laughter mingling with a look of understanding. You’re not exactly the poster boy for that kind of desire.”

I couldn’t believe what my father was saying. He told me no one could ever desire me, which gave me more freedom than any man.

“Dad, that doesn’t make me feel any better.”

“No, not what I meant at all. I’m sorry. It’s just you live without the weight of those expectations. It’s a different kind of freedom. People laugh but do not expect you to be a certain way. You can just be Jake.”

“I want people to desire me.”

“They will. I don’t mean you can’t find love. You will. You don’t have an expectation, that’s all. Trust me, you’re very handsome. You take that from me.” He laughed.

It made sense, but it still hurt my feelings.

“Yeah, that makes sense, dad.”

“Good, son.” And he rubbed my back. We both swam in the water for a few minutes before we returned. His father shared a sympathetic smile, and he felt better just from his father’s warmness. They hugged, and I could feel his huge cock touch my leg.

Aunt Jackie had a camera waiting.

“Aww. Let’s get a photo of the birthday boy and his dad.”

She snapped a photo. She looked directly at my father’s huge cock and then my thimble and just smiled at the black-and-white contrast. It was night and day. She was trying hard not to laugh.

Everything felt better until one of the girls pointed it out.

“Wow! Where is it?”

Everyone turned around and looked at me.

“It disappeared.”

It was quiet for a moment. But then, as that moment stretched into absurdity, laughter erupted—not just chuckles but full-throated guffaws, the kind that makes one’s stomach ache from the sheer hilarity of the scene. Everyone except a few, like Shelley and Mr. Rogers, began laughing louder than ever. Only people like Shelley and Mr. Rogers rolled their eyes at the group’s childish behavior.

I looked down and saw it had disappeared entirely. You could barely see the head. There were no balls, either. It was around a centimeter long. I was so embarrassed. The humiliation wouldn’t end. I turned around and pulled it out. It didn’t accomplish much, but you could see it better now.

After that, when the laughs and jokes died down, everyone wanted a photo with me — even the girls. They had no issue laughing at me but didn’t say why. They didn’t need to. My most precious private areas were public knowledge now. And even worse, one of the girl’s naked breasts rubbed on my bare chest, and my little weenie was hard and ready to explode.

She looked down and let out a little scream. Her laughter echoed, and everyone else saw what the commotion was about. My penis was firm and small. It was about two inches, which was even smaller than usual.

I could have played off I was a grower, but no, I had to sport the smallest boner anyone’s ever seen. I just walked back with my boner sticking straight right out at 45 degrees to my seat. The air was quiet and awkward. Eventually, people started talking again. But that image burned in their minds forever.

Toward the end, my stepmother had a cake for me.

“Make a wish, honey.”

A better year.

I couldn’t wish for a more enormous cock because that was never going to happen. His stepmom suggested they walk along the pier with constant jokes and teasing at his expense when the party was over.

“That sounds fun. Let me just put on my clothes.” I said.

“Jake, you don’t need to. It’s also clothing optional.”

I was stuck again in this whirlwind. I just wanted to wear clothes again. Was that too much to ask? At that point, almost everyone left except my father, stepmother, Aunt Jackie, Shelley, Mr. Rogers, and a few family members. They took a different path that led to a populated boardwalk. He may have seen one nude person out of hundreds. He thought this was a ploy, but the sign read it was “clothing optional.”

They walked along the pier with the giant crowd. Everyone was looking at Jake, shocked at a nude person since not everyone knew it was clothing optional, but that his penis was so small. They watched it bounce innocently around. It would stay innocent because it wouldn’t get any action soon, or so I thought.

After venturing through the laughter, even from kids and their families, teasing, and cameras pointed at my naked body, we reached the edge of the pier where people usually fished. Everyone was talking and having a good time. I would have been with my loved ones if not for the nudity.

Mr. Rogers walked up to me.

“Jake, happy birthday.” He gave me a warm hug. I haven’t had a chance to talk to you.”

“It’s nice to see you again.”

“I know people have been giving you a hard time for your body.”

“Yeah, mister. It’s quite embarrassing.”

I was eavesdropping on your father’s conversation, and I couldn’t help but feel sorry for you.”

“Look, I get it. My cock is just damn small.” I said, my voice filled with aggravation.

“No, because he started by saying you wouldn’t be desired. I got what he was trying to say, but it came out very wrong.”

“It’s true. Isn’t it?”

“No, Jake. As I told you before, I think you’re very attractive. You’ve inspired me.”

I looked up as Mr. Rogers removed his swimsuit. In the darkness, with the help of a few lights nearby, I could see he had a tiny cock too. It was harder to see because he could grow a bush. It was like a little mushroom. It was illuminating for me to know someone so manly, masculine, and powerful had a tiny little dick.

He pointed at it and asked, “Do you get it now? I’m like you, even though you are smaller.” He let out a little giggle, but it was out of a beautiful bond between us. “Like I said, come to me if you need anything. I’m here for you.”

“Your little cock is beautiful, Mr. Rogers.” I finally said after the shock wore off.

He blushed and thanked me.

“And I wouldn’t mind if you came in your birthday suit. I still want you to see my place.”

Jake smirked, and they hugged. Both of our little cocks kissed, and I loved every moment of it.

We walked back together, both in the nude, which did surprise my family. No one said anything because Mr. Rogers isn’t someone you ever want to offend. He got a few smirks, but his manly confidence was alluring, and even some women smiled at him with desire. This showed me I could be desired with a small penis. I just needed to be more like Mr. Rogers. He may not have shown it off at times, but he was still confident in everything he had.

Everyone said goodbye, and my stepmother and I drove home. I received a message from Shelley.

“Jake, I hope you had an amazing birthday. I’m sorry I didn’t get to chat with you. Don’t worry about the others. You know you are adorable.”

“Thank you, Shelley. Maybe I’ll come over soon.”

“I’d love that more than anything. You can put on another show. It was one of my most successful performances.”

We made it back home. I received so many gifts and money. I was still naked on the floor, going through everything, while my stepmom smiled at me on her chair. It was a nice distraction from everything that happened.

“Look, Mr. Rogers gave me a 100-dollar bill.”

“You know, Jake, I think it’s amazing you’ve kept this ruse going for this long,” my stepmother said, her voice dripping with mocking admiration as she looked at me with a knowing grin. My cheeks flushed a deep red, the heat of embarrassment spreading like wildfire under my skin.

“What do you mean?” I stumbled over my words, my voice barely a whisper, choked by the shame of being found out.

“Jake, it’s obvious. Since that day, I’ve known you were getting off on those water jets. The day I forced you into this so-called ‘nudist’ lifestyle, I watched you orgasm in the pool water. Right in front of me! How could you do that?”

I was drowning in nervousness, my guilt palpable. I couldn’t believe she knew this whole time. Her revelation felt like a strategic move to amplify my humiliation.

“I don’t know. But why did you do this to me?” I asked, my voice quivering, trying to sound innocent, but the words came out weak.

“Jake, it’s over. I know the truth,” she declared, her eyes piercing through my façade. I felt like I might vomit right there, my stomach twisting in knots.

“Okay, I’m sorry. The water jets just felt so good.”I tried explaining through the penetrating nerves.

“Look, Jake. I understand. I’ve done some questionable things, too. But right in front of me was where I drew the line.

“But why did you make me stay nude?”

“Because I wanted to punish you. You told a simple lie and have lied to me since you moved here.”

“Well, what was I supposed to say?”

“Like I said. I understand, which is why I’m telling you now because I feel like your punishment is over.”

I stood up, and this time, I was upset.

“My punishment? You were horrible.”

“Yes, I know. She pointed at my legs. “Tsk tsk tsk. Such a tiny little itty baby boy penis.” I couldn’t believe how harsh she was being about my cock. “That is embarrassing — hairless, thin, skinny, short, small, and non-existent balls.” I looked down at it and covered it with both hands. “And now, everyone knows about it. Every single person you know. There’s not much else I can do now.” She smiled, satisfied with her work. “Now that you know that I’ve known about your perversion, I hope you decide to be a better boy.”

I just stood there, holding my crotch. I started crying.

“Oh, Jake. Please don’t cry. This was to punish you. How do you think I felt knowing you lied to me for weeks? You know I hate lying.”

She walked up to me and hugged me. She wiped my tears away.

“I’m so embarrassed!” I shouted.

“I know.” She said empathetically. “I felt terrible at times because of how ruthless I was. But you never stood up and told me the truth. That could have saved you so much trouble.

“I’m so sorry,” I whined through the tears.

“It’s okay. Now, I hope you can be honest with me.”

“Yes, mommy.” I whimpered. I didn’t usually call her that, but I felt like a helpless little boy at that moment. “But I can’t get over it. Everyone knows how small I am.”

“Oh my. What do we have here?” Those eyes of hers widened to the unexpected revelation. Her dominant composure frightens me. I looked down and saw it grow into a two-inch boner. I felt so overwhelmed, and her nice touch turned me on. This wasn’t very pleasant. She knew I was a complete horny mess.

“I’m so sorry. Please let me go to my room.”

“Geez. You are such a pervert.” She knelt and grabbed my little penis with both fingers. She flicked it back and forth with her pinky, eyeing how much smaller it was than that. “I’ve put this little guy through so much. And I know from what you’ve experienced I can expect only good behavior.”

“Yes, mom.”

I tried to leave, but she held me down.

“So small. So tiny. Damn. So…”

I couldn’t handle any more humiliation. I don’t know where she was going with this. But I felt embarrassed because she was, in a way, infatuated with it.

But then the word “Hot” came out of her lips.

And a moment later, my cock was wet and warm. It was enveloped completely. My stepmom was sucking my little dick! The entire thing was quickly in her mouth. I was so ashamed but enjoyed it too much to end it. It felt amazing to have a warm mouth devouring my cock.

“You deserve a reward. You probably won’t ever be naked with any girls, so this is your only chance. My little virgin stepson.”

Little did she know I lost my virginity to Shelley, but I wasn’t about to tell her that.

“Mom, you don’t have to. It’s okay.”

She looked into my eyes.

“Oh, honey. I know that.” She stopped. “But look at this.”

She rubbed the tip of my little penis with her pinky, and a long strand of pre-cum extended out. She licked her finger and continued. I moaned, which I could tell she enjoyed.

She didn’t even have to bob her head back and forth. It was so small she just needed to suck in and out. That wasn’t very comfortable.

“The moment I first saw you naked, I couldn’t believe it. It was so freaking small. I wanted to laugh, but I couldn’t. And when you got out of the pool to try the slide that day. I meant every word when I said you looked like your four-year-old self, laughing and running around naked with your little ding-a-ling jiggling around. Your penis is still the same little boy size, and it will always be that way.”

“I had a feeling you meant that. I was so embarrassed.”

“And the more I humiliated you, the more I was turned on by it.”

“I turned you on?”

“Not you particularly, but the feeling of dominating a man or boy, in your case, with a tiny penis. The fact something so small and private can determine a man’s fate. Why do you think I invited all those people that day for the barbecue? That night, I had to masturbate my clit to how embarrassed you were. You’re not the best actor, hun. I could tell you were embarrassed the whole time. I will give it to you. You were dedicated to your role. I mean, for Pete’s sake, you were butt-ass naked in front of the whole neighborhood.”

“I know,” I mumbled.

“And I saw that little orgasm you had this morning. You should be ashamed. You’re in so much trouble for something so small and insignificant.”

“So, when you said, ‘any girl would be lucky to have me, did you mean that?”

“Well, they’ll be lucky to have someone so loyal because you could never cheat. And, of course, not. I think most girls would laugh at this little tiny thing. All my female students did today. And what about those two older women? They seemed to like you.”

“Yeah, when they just saw my backside. They couldn’t stop laughing at the front.”

“See, my son. There is no shame in knowing the truth — you’ll probably always be single. I mean, Mr. Rogers took a liking to you.”

“Yes, he invited me to his place.”

“His cock is so tiny too!” She blurted out. “Oh, and seeing your father was a turn-on for me. You both are so different. His genes skipped a generation. The head of his soft cock is bigger than your hard dick.”

I could see this was turning my stepmother on. Her degradation became her pleasure. I was horrified with how much she was berating me, but I enjoyed her attention. I was making her happy, even at my expense.

“Yes, I know.”

All of her clothes came off as she gave me a strip tease. There were her little boobies and beautiful bubble butt. I groaned at the site of her smooth, naked body. She started sucking again. She took a few short movements. My cock had never felt better. I wanted this to last forever.

But honestly, with everything that happened, I could feel it coming. This couldn’t be happening. It was way too soon. She only sucked it for around a minute before she started ridiculing me. I could feel it.

“Ahhhh,” I shouted.

I could feel the white-hot semen release from my little boner. She swallowed all of it. She kept sucking until she felt it become a little peanut in her mouth.

“My poor baby. Premature ejaculation with barely anything coming out of those tight little balls. More to add to your humiliating list, Jakey.”

“I just looked down at my little thimble of a nub, feeling more exposed than ever.”

“Oh, baby. There’s nothing wrong with what we did. I’m your stepmother. This is completely natural.” She was so wrong, but I wanted more of her. “I hope you had a beautiful birthday.”

“I did. Thank you.”

We were natural — both fully naked. We looked at each other. She was simply beautiful.

“No more with your naughty behavior. If you ever find yourself with those perverted thoughts, you talk to me. I’ll take care of it.”

“Do you mean?” I asked eagerly.

She nodded with a comforting smile. She may have caused the most humiliation I’ve ever experienced in my life, but she was also the source of the most recent pleasure I’ve ever felt.

I loved my stepmother. Everyone knew I had a very small micropenis. And they constantly reminded me. But she loved me for who I was. And I was finally happy. She was now on my side, embracing her stepson like she always wanted to.

But life isn’t that simple. This may have been the final dilemma of Jake pretending to be a nudist, but he unfortunately found himself in countless embarrassing dilemmas with his stepmother. That’ll have to be another time for another story.

 

The End.

 

*AI has edited this story 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.

2 comments

  • PhillyPhan

    So glad you cameback to this story and are writing again. Your stories are the best ones.

    Reply

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