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…

“Mistress? You want me to call you mistress?”

Shelley circled around and carefully looked at every section of my naked body.

“That’s correct, little Jake.”

Her intimidating gaze sharpened at my little soft penis. It bravely stood out for her unspeakable temptation. I looked down and saw just how small it could be. Our eyes locked, and we both knew how tiny it was.

Overwhelmed with intimidation, I quickly realized I wasn’t at my stepmother’s place. In a way, I had the freedom to be myself. I didn’t want anyone examining why I was a little boy between the legs.

I covered my little scared willy with both hands, even though I needed just a finger to do so.

She raised an eyebrow and asked, “Jake, what are you doing?”

I didn’t know what to say, so I stammered, “Nothing. I just don’t want you looking down there.” Due to my shyness, I looked away.

“Why not? I don’t think that is very fair to me. I promised you the opportunity to be yourself. You are a nudist, and I have a big place for you to run around naked.”

I almost thought about telling her the truth, but I couldn’t. Without a second thought, she would tell my stepmother everything.

“Well, I think it would be better if—”

“And what’s the point in covering yourself up?” Her eyes hadn’t left the little space my hands were covering. “I’ve seen your handsome LITTLE body many times.”

Using the term ‘little’ made me recoil, but I responded, “Well, this is a new place for me to be myself.” I gave her an innocent look, “It would be fun to wear clothes. Don’t you think so?”

“Are you sure this is what you want to do?” I nodded, followed by, “Then follow me, Jake.” She smirked and started walking up the stairs, “I have something special for you to wear.”

I submissively followed her but knew I was walking into something I would regret. She led me to her dark bedroom, subtly lit by her opulent chandelier. The entire room seemed inspired by a gothic theme during the Middle Ages.

“Wow,” I said to myself.

Shelley’s taste added a mysterious element. I feared who Shelley was, but it was also a little exciting.

She scrambled through her closet, “Where are you, you little devil?” I couldn’t help but look up at her dress as it rode up her waist. She searched through a pile of clothes until she said, “There it is.” She pulled out a silky black pair of revealing panties and threw them on the bed. “These are perfect. They belong to my daughter.”

“Err, your daughter?”

“Yeah, she’s around your age. She’s going to university right now.” She saw me looking at them with horror and asked, “Aren’t they so cute? And I am certain they will fit you quite nicely, on the count of, you know,” looking at my diligent, sweaty hands.

I picked them up, incidentally, uncovering my little bald penis. She looked right at the tiny one-inch wonder and just maternally smiled. She witnessed my side profile, and it was scandalous. I couldn’t believe this was the alternative to being completely butt naked. And the fact they belonged to her daughter, who was around my age, was mortifying.

“Do I have to? They are quite revealing. Is there anything else I could wear?”

“Sure,” she said as she searched through the closet. She pulled out a see-through nightgown. “How is this?”

I looked at the dress and turned to the panties. I couldn’t imagine myself wearing a dress. I did what, unfortunately, I had to do.

“I’ll just stick to the panties.”

“I thought you would.” She grabbed them and covered my center with them. We looked at my body in the mirror. “See, they will be just perfect for you.”

“I guess so.”

“Aww. You’re so modest. I like that.” I blushed a little and just stood there looking at the panties. “Don’t be so shy. Not after what you did at the barbecue. How could someone like you feel that way?”

“I’ve just never worn panties before.”

“And I’m also guessing you’ve never skinny-dipped in front of a bunch of strangers.”

Did she have to remind me of the worst, most embarrassing day of my life?

“Haha, that is true.”

“You’ll be fine. Anyway, I’ll let you try them on. I’ll be downstairs.”

“Okay, thank you, Shelley.”

She crossed her arms and asked, “You mean?”

“Oh, mistress. Sorry about that.”

“That’s a good boy. I’ll be waiting.”

I waited for her to leave until I looked at the panties again. I couldn’t believe I was going to do this. I slipped them on, feeling shivers across my smooth legs.

I rolled my eyes at the fact they actually were a perfect fit. I looked in the mirror, and I couldn’t detect a single hint of a bulge. It was completely flat. I was like a woman from the waist down—flat, smooth, and feminine. I had a deeper voice and was taller, but that couldn’t prevent anyone from seeing me like a girl right now. And I really couldn’t blame them.

I took a deep breath and walked down the stairs. Shelley was lying down on the couch, waiting for me. I was incredibly embarrassed.

“My, oh my. What do we have here?” She walked up to me and smiled. “You look so adorable. They fit like a glove—even better than my daughter. They were too tight on her.”

There’s no way that was true!

Was she telling the truth? Did they fit me better?

“Well, that’s good then,” I shakily replied.

“Do you want something to drink?”

“Nope, I’m okay for now.”

“Well, let me show you the backyard.”

She held my hand and led me to the back door, leading to a beautiful garden. It was an assortment of colors, flowers, vegetation, and smells. Down a gravel path, we were accepted by a gust of silent wind and a few blue jays until we reached a serene lake.

“Oh, here’s the lake you mentioned.”

She smiled and said, “I’m glad you remember that.”

“It’s beautiful.”

A big tree surrounded the lake. It looked like it came from thousands of years ago.

“Do you want to go in it?”

“I do.”

She opened the gate but stopped me, “But before you do, I need you to confess something. Jake,” she asked.

“Yes?”

She smiled and asked, “Did you really just wear my daughter’s panties to maintain this facade of being a ‘nudist?’”

My face turned white, and my nerves were imploding.

“What do you mean?”

“Jake, don’t lie. It was so obvious you weren’t a nudist at the barbecue.”

“But how?”

“Jake, my boy, your face was bright red the entire time. I don’t think anyone caught on, but I did. I know when a man is genuinely embarrassed—like you are right now.”

I was backed in a corner and had to tell her the truth.

“Okay, it’s true. I’m so embarrassed.”

“Yeah, you are wearing my daughter’s panties. What were you thinking?”

I told her the whole story, and she calmly reflected on everything.

“But, the water jets?”

“I couldn’t help it. It was an amazing feeling.”

“It’s quite pathetic, but I understand. I’ve had some fun with the shower hose.”

“Wow, that’s honest.”

“Hey, don’t judge me. You got off from a water jet. In front of your stepmom.”

“I wasn’t; it’s just.” —

“I’m a woman, Jake. It’s what we do, sometimes.” There was a short silence. “So, your mom doesn’t know you’ve been lying this whole time.”

I looked down and nodded.

“What am I going to do?”

“There’s not much you can do, or she’ll see you like the pervert you are. I don’t have the answer, but it will be fine.”

“Please don’t tell her any of this.”

“I would never. What an awkward conversation to have with an old coworker.”

“Phew. Thank you, mistress.”

“I like it when you call me that. I think it suits me.”

I smiled and said, “It does very much.”

“Now, how about you take off those panties? I’m not your stepmother. You don’t have to worry about being naked in front of a family member. You’ll be safe here.”

“Alright, if that’s okay.”

She kneeled and rubbed the front of the panties. I was a little surprised when she started massaging my buttocks. She grabbed the waistband of the black panties and pulled them. I felt the cool air kiss my body as it came down. I felt really embarrassed that my small private parts bounced inches away from this woman’s face in broad daylight. She could see how tiny and undeveloped I was.

We might have been alone, but the world was observing what little I offered. I know it’s a stereotype, but as a man, I feel I need to be the provider. But what can I provide? I can only offer a two-inch little boner. What was I supposed to do with that? I would have had a boner instantaneously, but after releasing it three times that day, it was challenging to produce an erection, which made me feel more than thankful.

“Awwww. There’s the little tiny ding-a-ling.”

I saw her squarely look in the direction of where my little tiny boy penis was located.

“This is what everyone at the barbecue was having the best day over. It was the source of our entertainment.”

My face turned a little red. I can’t believe she was openly ridiculing my little bald penis. Why couldn’t she get over it? My penis is just tiny! It’s not a big deal.

“Please stop. I’m so embarrassed. I hated that day.”

“Yeah, you weren’t hiding anything that day. We all had a perfect look at what was between your legs, and we all were astonished.”

“Okay, I get it, but can you please stop making fun of—”

“And the fact you came out of the water with a ridiculously tiny little boy boner bobbing around for our enjoyment was the icing on the cake. Most of us couldn’t handle it anymore. It was the funniest thing I’ve seen in my.” —

“Okay. I get it. My penis is really tiny!” I shouted. My face was even redder from the anger rather than the embarrassment. “I’m tired of everyone humiliating me every chance they get. I’m a human being with feelings. And I can’t take it anymore.”

I’ve never been this angry before, but it all just came out.

“Listen, Jake. I understand your anger. You can’t help being born with such a tiny little wee-wee. But I didn’t mean to make you feel bad about your body. Your little pee-pee is so cute.”

“Then why do you keep making fun of it?”

“I’m not. I’m admiring it. I think it’s quite amazing. It’s so small and endearing.”

“That’s it, I’m leaving,” I turned around and dramatically stomped to her house.

She called out to me, “Wait, you can’t leave. You’re naked. Someone will see you, and trust me, you’ll wish you just had my reactions. Some people can be even more cruel.”

I turned around and said, “Fine. I’ll stay.”

“Yay,” and she hopped up and down.

“But can you stop mentioning the size of my penis? It’s super embarrassing.”

“You shouldn’t feel embarrassed about your body. If I said, ‘Wow, your cock is so big,’ would that embarrass you?”

“No, it wouldn’t.”

“Then simple logic would support me saying, ‘Jake, your cock is so small,’ that shouldn’t embarrass you either.”

“But it does. You’re a woman. You could never understand.”

“Maybe not, but damn, you boys prioritize your little playthings too much. I don’t care how big or small your penis is. I’m still going to point it out.”

“But it’s still so humiliating. I just can’t seem to get over having such a small cock. It sucks to be so tiny and incapable.”

She responded sympathetically, “Jake. This is a safe space for you. You are a wonderful boy, but I can’t lie to you. And I shouldn’t feel compelled to lie to protect your feelings. You were honest with me, and I respected that.”

“And thank you for that.”

“I mean, I could lie and say there’s nothing to talk about, but I can’t ignore what anyone would think seeing your naked body.”

“What would they really think?”

“I think many would laugh or be simply shocked that a grown man can be so small. And some people would love it.”

I looked up at her, “Really?”

“Honey, I didn’t just invite you for no reason. I’m fascinated by you.”

“By what?” I asked.

“The truth is, I am simply amazed at how tiny your penis is. It is the smallest cock I’ve ever seen in my life. When I first saw you naked, I couldn’t even comprehend what I was looking at. I could barely see your penis from where I was sitting that day. It was a real puzzle in front of all our eyes.”

“I always thought anyone would laugh at me.”

“Oh, don’t get me wrong. You are an adult man with a mere dot between his legs, and to cover it, you would need a little microscopic laughing emoji. It’s pretty freaking hilarious, but I’m still very intrigued by it.”

“I can’t believe you feel that.”

“Well, I do, darling,” she bent down again and just looked at my little pebble. “I can’t believe you convinced your stepmom that you’re a nudist. I can’t imagine her reaction to seeing her stepson hung like a toddler.” She reached out and actually flicked it with her index finger. “My god, your cock is so tiny,” subsequently covering her mouth and giggling.

“So, I don’t have anything to worry about?”

“Haha, well, I can’t speak for every woman, but you don’t with me.” I sheepishly smiled and embraced what she was saying. At least she came from a place of admiration, not ridicule. “C’mon, then, let’s go to the lake.”

She started quickly stripping, and pretty soon, she was naked with me. She was a mesmerizing woman. She had the most beautiful breasts, long, smooth legs, and a bush covering her vagina. I can’t believe she has more hair than I do.

She ran for the water, and I just watched as her bare butt danced in the open wild for me. I excitedly jumped in right after her. The moment between us felt innocent and magical. We were both naked and playing like children.

“This is so relaxing. I can’t believe you live in a place like this.”

“Well, I like to live a different lifestyle from most people.”

“It’s amazing.”

After swimming in the lake for a while, she invited me to her secret place.

“Jake, I want you to come see this.”

I couldn’t stop looking at her wet body. I hopped out without even thinking I had shrinkage. I was so comfortable I didn’t ponder the little thing between my legs.

“Do you have a towel? It’s a little cold.”

“Don’t worry about that. The wind will dry us off.”

I just nodded in agreement and took off. She didn’t even look at my penis and guided me along a simple path of grass and hydrangeas. We reached a wooden door that led to a secret garden. It was full of even more flowers, and in the center was a hand-made swing.

“My father built this for me when I was a little girl. And I’m so happy to share it with you.”

“What do you want to do?”

She whispered, “You.”

I stepped back and asked, “What do you mean?”

“It only makes sense that where I played as a little girl is where I will take your virginity away from your little boy penis.”

She immediately threw me on the swing and held me down. She started kissing my body.

“Shelley, what are you doing?”

“It’s mistress, and I’m having my way with you.”

I was beyond afraid and needed to make an excuse.

“But mistress, I’ve already had sex before.”

She started cackling.

“Jake! Haha, you can’t make jokes like that.” She looked at my little micropenis and just kept giggling. “It’s obvious you are still a virgin. With a tiny cock like that.” She started kissing the head of my little cock, and I felt powerless. “Wow, the cold did a number on your nether regions. Now you see why I didn’t offer you a towel.”

I couldn’t believe she made me air dry so my boy parts would be smaller than humanly possible.

“But I am telling you the—oh wow.”

At that moment, I could only focus on the pleasure she was feeding my tiny penis. It barely passed her warm lips as she kissed it. She was clearly satisfied with my honest reaction. She then put the entire thing in her mouth, which didn’t take any effort. My one-inch soft cock was swimming in the mouth of an experienced, older woman.

“I’ve never had sex with a man who had such a little itty bitty little micropenis.” She continued to make love to my skinny body, and the hotter it got, the more she degraded me. “Everyone at the barbecue couldn’t stop laughing at your naked body. My jaw physically dropped when those swim trunks hit the floor.” She kissed me on the lips. “I knew I wanted you.”

“Ohhh.” I moaned. “Really?”

“Yes, you were so hot, and I couldn’t believe how tiny your penis was. It felt so tiny in my mouth—even smaller than a grape.” She started sucking me again, and after some time, it finally grew in her mouth. She stopped and looked at my boner. “Now, that’s what I’m talking about. You literally have a micropenis.” She compared it to her pinky. “It’s smaller and thinner than my little pinky finger.”

The euphoria of her beauty made me feel lost. The capability of this woman was alluring. I massaged her bosom and almost passed out from her tenacity to take away my virginity.

I was afraid to say anything, but I murmured through the moans, “You’re beautiful.”

“Mhm,” she said as she bobbed up and down on my little boy boner. “Skinny frame, insanely tiny penis fit for a small boy, tiny little virgin balls, and such a cute face. I can’t believe a man like you physically draws me in so much. You don’t have anything between your legs. I’m using my imagination to suck on your genitals.”

“Keep going, mistress.”

“I think your little pecker is quite adorable. It’s exciting to have this much power over something so small and harmless-looking. It’s so easy to work such a teenie weenie like this. I can enjoy every little inch of you between my big lips and blow up your entire world. You never thought a woman would ever do this for you after she learned about your little secret. Well, that’s over with, honey. You could have the smallest micropenis in the world, and I would still want you.”

And there it was, “It’s happening!” I shouted.

I felt my penis release the anticipated load into this goddess of a woman. After emptying my peanut-sized balls, I collapsed on the swing, unable to move. She swallowed my entire load. With her appetite, she continued to drink every last drop of semen from the little tip of my virgin-free dick.

“How did it feel to lose your virginity, baby cakes?” I could barely form a sentence, so I just moaned. “I’ll take that answer,” she said with satisfaction. I lay there, completely numb. I just lost my virginity to this woman.

I just looked up at the sunsetting sky, the rays beaming down at my face.

“Thank you so much. That was amazing.”

“I’m glad, sweetie.”

She looked at my little penis and giggled, “Wow. If it was tiny before, I can’t believe it now.”

I looked between my legs and saw a puny tiny nub hiding in a turtle shell.

“Wow. That’s tiny. And you love it.”

“Hehe, I do.”

“I can’t believe I’m no longer a virgin.” She got up, so I asked, “Wait. Where are you going? Can we, you know, maybe have penetrative sex?”

She started laughing, “Jake. What did I say about making jokes like that, silly boy?”

“I thought I would try. You can’t blame me, haha.”

“True, but listen, I have to take care of something. But can you meet me back at the house in around 30 minutes?”

“Anything for you, mistress.”

“I always like the sound of that.”

I watched her walk away and was hypnotized by her naked body. The way her big bubble butt jiggled with each step excited me. I’ve never been happier. My little penis was tiny and happy.

With nothing to do, I just walked around the garden. It was a massive space of land she owned. After what felt like 30 minutes, I decided to walk back. I was proud to walk with my little pee-pee bouncing around.

Before I entered her back door, she came out. She was fully clothed and wearing a sparkly dress.

“Jake, wait a second. I want you to enter this way.”

We went to the side of the house, which led to another door.

“Now that you can recognize how small your penis is, let’s boost your confidence.”

“How?”

“You’ll see soon. I’ll meet you inside,” as she walked back.

What’s going on? I thought. I walked up a short ramp and opened the door to complete blackness. I touched what was blocking me, and it felt like fabric.

Why is there fabric here?

I slowly pushed through it and finally was in the house. I was horrified by what I saw.

This couldn’t be happening!

I was standing on a stage with bright lights in front of a loud crowd of 20 older women. My eyes widened to the realization I was completely naked with a very tiny dick exposed to a bunch of strangers.

They had no shame and were cheering and taking photos of my body. On the stage, there was a stripper pole. Both sides of the stage had jumbo screens to magnify the center of my manhood. You could clearly see how tiny my pee-pee was.

They could see every compromising detail. There was no hiding the truth from the women in the back. It looked ridiculous seeing something so big show a close-up of my comically small ding-a-ling.

Mistress was on the stage with a microphone, “Ladies, feast your eyes on your performer tonight. This is Jake. I first saw him at a barbecue, where he skinny-dipped in front of his neighbors. He’s a lovely boy. And if you haven’t already noticed,” she pointed at my cock, “He’s got a very tiny little boy cock.” This caused the audience to spout laughter louder than it should have been. I just stood there as they mocked my absurdly small penis. “And it shouldn’t come to shock any of you, but he’s self-conscious about the little ding-a-ling wiggling between his legs, so take it easy on the little guy tonight.”

Their laughter continued until she prompted them to silence themselves.

“Jake, tell the crowd about yourself.”

She saw I was at a loss for words, and she gave me some encouragement.

“C’mon, Jake. Think about what we talked about today. This is your chance to show off what you can do.”

I felt more comfortable and said, “Well, I’m Jake, and I guess I’m your performer tonight,” I laughed awkwardly.

“You heard it here, folks. Anything else, Jake?”

I knew what she wanted me to say, so I proceeded, “And yes, my penis is really, really, really small, tiny, little, microscopic, mini, puny, and I’ll even go with toddler-sized. It is quite embarrassing, but I’m more than proud to show you fine ladies a good time.”

They cheered and laughed at me.

“Without further ado, The Micro Jake.”

The lights changed to a bright pink, showcasing the pole. I walked up to the pole and started dancing on it. I was shy and didn’t know what to do, but I tried my best. I spun around the pole, twerked for the crowd, and humped the air. I felt confident from the crowd’s supportive screams.

“Shake that little thing.”

“I’m so wet from Jake’s micro member.”

“Good lord, he is so tiny.”

“Even with the jumbo screen, I can barely see it.”

I ground on the pole, and I felt sexy and desirable. I seductively danced down, shaking my hips and wiggling my little cock from side to side. I walked to where the crowd was, and each one took a chance to spank my ass, shove hundred-dollar bills up my butt crack, and flick my little weenie.

Even though the women were having the best time making fun of my little cock, I never felt more alive and authentic. I gave some of the women a lap dance, and each one made it a point to giggle at how small my penis was. They couldn’t get enough out of my shrunken little micropenis.

“Such a tiny little thing between his legs.”

“How is it even possible for a man to be so small?”

“He is so cute. I can’t believe someone like him exists.”

“I now have a fetish for small cocks.”

Each comment may have been embarrassing, but I loved every moment. I ran back to the stage and continued to dance around the pole like a professional. I felt aroused and saw my cock reach the two-inch maximum.

“Oh my god! He’s got a boner.”

“And it’s also super tiny!”

“No wonder he’s so shy.”

“If I had a cock, and it was that small, I wouldn’t want anyone seeing it.”

“Damn, he’s so hot. I love him.”

“Haha, he can’t use the ‘I’m a grower’ excuse.”

I couldn’t believe I had another boner, but there it was, ready to shoot another load. After every single event that happened that day, from meeting Mr. Rogers, showering with my stepmom, losing my virginity, and now performing naked, I couldn’t help myself.

Without even touching myself, I started humping the air, and they all watched streams of white cum fly from my tiny penis and onto the floor. The crowd went completely wild over watching their performer blow his load. The cameras were going crazy. Usually, I would be incredibly humiliated, but I felt empowered to be a sexual deviant.

The music grew quieter, and the mistress walked on the stage.

“That is all the time we have for tonight, folks, but please come again to the next event.”

I took selfies with each audience member, and each one flicked my little penis and took close-ups of my body. After meeting everyone, I had many kiss marks on my face and body. After the last woman left, the mistress slowly clapped for me.

“That was just amazing, Jake. I always knew you had it in you,” and she hugged me.

The door opened to a big, masculine-looking man. He looked a little similar to Mr. Rogers, but he had a more rugged face.

“I guess you are done for the evening.”

“Yep, all thanks to Jake.”

He kissed her, and they both looked right at me and my naked body.

“Wow, this must be Jake. It’s nice to meet you. You know, this gal can’t stop talking about you.” He looked at the micropenis that slept inside me. “But she didn’t do your body justice. She said you had a tiny penis, but I never thought it would be that fucking small. I mean, he’s got no dick.”

“Haha, Kyle. Don’t be rude to our special guest.”

“I’m not complaining if it made us a lot of money tonight.”

“It did. It was our most successful show.”

“Hell yeah. I owe it to this little dude—especially you, little guy,” as he spoke directly to my disappearing groin. He flicked my little penis with his finger and just laughed.

“Well, I should take the little man home. It’s been a long night for him.”

It was nighttime, and my mistress drove me home.

“Jake, I’m so proud of you. You proved how amazing you are to the world tonight.”

“You mean just a couple of women?”

“I think you mean some of the wealthiest women in the state. We host those parties for some raw entertainment for them. They were really into you when I first mentioned your name. I didn’t tell them about your little boyhood because I wanted it to surprise me. And boy, were they surprised.”

“I appreciate you giving me the chance today. I feel like I can take on the world.”

We arrived at my stepmom’s place, and I exited the car. I came to her window.

“Thank you so much again,” and I softly kissed her.

“Don’t get the wrong idea, player. I still need bigger, and Kyle does that for me that your little winky down there could never do. It’s not personal.”

“I’m just happy I had a chance to be with such an amazing woman.”

“Likewise, sweetie. Don’t you and your little weenie get into too much trouble.”

“After tonight, who knows,” and I winked at her. She watched as I walked away with my soft little penis bouncing around in the moonlight. She chuckled and shook her head.

I walked into the house to my stepmother, looking disappointed.

“Jake, it is past midnight. Where have you been?”

“I’ve been with Shelley the whole time. I had an amazing time.”

“I can see that. Next time, you better let me know where you are, or I will smack your little pee-pee off.”

I just laughed and walked away. She looked dismayed by my confidence. I fell onto my bed and immediately fell asleep on the best day I’ve had since I’ve lived here. I can’t imagine what will happen next for me.

 

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.