Wee Winky Willy

By Max Swan.

Sitting around drinking some beers by the fire pit in his backyard Will Higgins enjoys the time with his friends Trisha and Luke.  The nineteen-year-old adults have been friends for years since elementary school, and now they’re all unemployed with an ‘I don’t give a fuck’ attitude to life.  Will is a weedy guy, a real ninety-pound weakling with dark hair and blue eyes.  Trisha is a curvy blonde with DD breasts.  She doesn’t have model good looks but is passable as pretty.  While Luke is an ex-football jock, muscular, and popular with the girls his age.  He’s also black.

The three of them have one thing in common–they’re bored.  In fact, most of the time, the three sit around and commiserate about how bad they have it and about how pitiful their lives are now high school is behind them.  The three get along exceptionally well.  There’s a trust between them that made them best friends.  Unfortunately, the three still live at home as the unemployment aide is too small to pay rent.

“Hey, guys, what’s the worst thing that’s ever happened to you?” Trisha asks, her eyes brightening.

“Mom caught me smoking a joint,” Luke said and grimaces.  “Man, did I ever get it.  She threatened to kick me out.  The old man really gave it to me when he got home too.”

“Fuck,” Trisha said, shaking her head.  “I heard about that from my mom.”

“Yeah, they overreacted big time,” Luke said, his face going red.  “It was just weed, for fuck’s sake.”

“Willy?” Trisha asks.  “What’s the worst thing that’s ever happened to you?”

Will blushes.  Something did happen to him recently that he found very humiliating.

Trisha must have sensed his discomfort because she blurts, “Willy, why are you blushing?”

“Cos it was super embarrassing,” the skinny white boy said.

“It must’ve been,” Luke said with a smirk.

“Yeah, it was,” Luke said, wishing he’d never mentioned it.

“Go on.  We won’t tell anyone.  You know you can trust us.  What happened to you?” Trisha asks.

Will trusts his friends, and even though he knows they’ll probably rib him for what happened, he knows they still have his back.

“OK, but you have to promise it stays between us,” Will said, eyeing his friends.

“Sure,” Luke said.

“Fine,” Trish adds.

“Are you sure you wanna hear this?  I mean, it’s kinda personal,” Will said meekly.

Part of him is hoping they’ll let it drop, but another part hopes they want to know.  It’s an excellent opportunity to finally unload this baggage and maybe get their opinions.

“Of course, we wanna know,” Trisha said and smiles.  “No matter what, we’re all friends here, right, Luke?”

“Fuck yeah,” Luke said with a nod.

“It happened a few weeks ago.” Will begins.  “I decided to go for a swim down at Lake Redding.  I thought I was alone, so I decided to go skinny dipping.”

“I see where this is heading,” Trisha said and smiles.

“Anyway, I swam for about an hour and thought I heard some voices, so I got out to find my bathers and towel were gone.”

“Oh, snap,” Luke said and chuckles.  “Someone got you good.”

Will grimaces.  “Yeah, fucking assholes.  Anyway, I had to walk home completely naked.  There wasn’t anyone around, so I felt a little better after a few minutes.  It was a little windy that day and the breeze blowing on my wet skin chilled me a bit, so I was sort of in a hurry.  I didn’t see them until it was too late.”

“Them?” Trisha asks excitedly.

“I was walking with my arms across my chest trying to keep warm when out from nowhere came two girls about my age and a man.  They looked like tourists, a father, and his daughters.  Anyway, one girl cries out, ‘Fucking hell, a naked man,’ as the others laugh.

‘How can you tell it’s a man?’ one asks with a smirk.  ‘He’s practically got no dick.’

They began making fun of me.

‘What’s your name?’ the man asked.

‘Willy,’ I told them.

To which he then shouts, ‘Wee Winky Willy.  That’s you all over, baby dick.’

‘It fits.  Hey, Wee Winky Willy,’ laughed the first girl as she obviously was making a reference to my private parts.

Well, they taunted me and chased after me most of the way home, making crude comments about my privates, calling it tiny and a shrimp dick.  I lost them near Hanson’s Bluff, but I have never felt so humiliated in my life.”

“Damn, Willy.  That was rough,” Luke said and laughs.  “The last time I saw your junk was like when you were twelve.  It has grown, hasn’t it?”

Willy’s face is red.  “Not as much as yours, Luke.  But that’s not the end of it.”

“Oh?” Trisha said wide-eyed.  “Do tell.”

“I decided to go swimming again a couple of days later,” Willy said, trembling.  “As I was walking along the path, they spotted me again.

They chased after me calling out, ‘Hey, Wee Winky Willy.’

They chased me down the path and soon caught me.  The man grabbed me from behind and held my arms while the girls pulled my bathers down to expose me.  Soon a couple of women came up from the lake, and they all took turns mocking my dick as the man restrained me.  They called me pathetic, a baby dick, the smallest they’ve ever seen.  The man wouldn’t let me go, and I had no choice but to endure the humiliation.  It turns out the girls told their friends about me, and they decided to wait to see if I’d show up at the lake again.  I was never so ashamed in my life.”

Trisha and Luke gaze at each other silently.  Luke finally spoke and said, “I certainly understand why you hated that.  It must’ve been fucking horrible.”

There was a moment or two of silence. Then, finally, Trisha notices Willy’s blushing a second time and said sweetly, “Willy, why are you blushing again?”

He just stares into the fire pit.

“Willy?” she said firmly, “Tell us.”

The moment of truth arrived.  Willy decides to go all out and be brutally truthful with his friends.  “Well, if I’m honest, I didn’t really hate it,” he said, feeling his stomach roiling.

“Do you like being naked in front of strangers, is that it?” Luke asks with a smile.  “Do you like it when they mock your little dick?”

His question causes a heavy tension felt by all as they wait for his answer.  “I don’t know.  It’s not that I like to be naked.  It’s hard to explain,” he said, frowning deeply.

Trisha asks, “Is it that you liked to be made fun of?  Was it the humiliation that you liked? All those girls laughing at your lack of manhood?”

Willy shrugs.  Luke and Trisha frown at him, so he tries to explain further.

“I’m not sure, really.  It’s just looking back on it.  I find it was both the worst and the best part of my life so far if that makes any sense.  My best answer is that it was probably a combination of everything.”

“What are the things that came together?” Trisha asks.  “Maybe we can help you sort this out.”

Willy blushes further, knowing he had told them a very private part of himself.  For a moment, he thought about just dropping the whole thing, but he glances into Trisha’s soft blue eyes and sees a caring, intimate gaze that seems to really want to help.

“This might not make sense, but at first, it was OK to be naked because someone took my gear, right?  But then the way those people reacted to my nudity; it wasn’t OK.  It made me feel funny.  Excited and dangerous.”

“Is that all?”

Willy shakes his head.  “No, the humiliation was extreme.  They all had a chance to see my secret places, so to speak.  They mocked me terribly, yet on top of all that, I felt aroused.  I jerk off nonstop, thinking about it.  Remembering what they said to me.  How they looked at my dick.  It makes me so hard.”

He forces a small fake giggle, which obviously signals his discomfort.  Willy isn’t sure how they’re going to take what he just said.  He wants to act like it’s no big deal, to appear strong lest they too make fun of him, but somehow he gets the feeling they aren’t going to do that.

“You’re one hard-ass,” Trisha said and smiles.  “Few people would’ve shared such intimate details with their friends.  I admire you for that.”

Her words take the edge off his fears, and he begins to feel better.

“Damn straight,” Luke adds.  “Sorry to hear you gotta tiny dick, though.  That must suck.”

Willy shrugs at Luke’s comment about his dick.  “It is what it is,” he said softly.

“All we’ve done lately is sit around and complain about how bored we are and how things suck,” Trisha said.  “Well, I have an idea on how we can change that and bring some fun back into our lives.”

Willy’s eyebrows rise.  “Oh?”

“Let’s do something really fucked up,” she said, pausing for emphasis.  “I’ll call it Wee Winky Willy.  Whenever we do this, we’ll recreate that mix of things that happened to you so you can re-experience it.”

“How the fuck are you gonna do that without getting me in trouble with the cops?” Willy asks.

Trisha thought carefully for a few minutes.  “How’s this.  Luke or I will say ‘Wee Winky Willy,’ and then explain what’s expected of you.  Each time will be different, some lasting a few minutes while others may last ages.”

“What if I don’t wanna do it?” Will asks with a shudder.

“You have to do it, just like at the lake.  You’ve got no choice,” Luke said.

Will can’t believe what he’s hearing.  They actually want to put him in situations that mimic his horrible experience at the lake.  “Why do you guys wanna do this?” he asks with a deep frown.

“Because it’ll be fun,” Trisha said excitedly.  “Just think of all the possibilities.  You said yourself you had been unable to recreate that feeling again.  So, why not let us have a go?”

Will has to admit his curiosity has peaked.  He starts to get that funny sensation in the pit of his stomach again.  “So let me make sure I understand this.  When you guys will say, ‘Wee Winky Willy,’ I have to strip naked and stay that way until you tell me otherwise?  No matter where I am and no matter who might see me?”

“Yes, but once you refuse to do what we say, it’ll be over forever.  Neither Luke nor I will ever bring the subject up again, right Luke?” Trisha asks.

“Right,” Luke agrees quickly.

“So, I can refuse if I don’t wanna do it anymore?” Will said.

Trisha nods.  “Once you agree to start, you have to continue until we say stop.  Once you say stop, it’s over for good.”  She stares at Will deep into the eyes.  “Do you agree to our terms?  If you don’t, then we’ll understand and say no more about it.”

Will peers at her, then at Luke.  His pulse quickens as he ponders the idea.  The boy’s torn between the excitement doing it would supply and the painful humiliation he might have to endure.

“I’ll do it,” he said in a hurry before he has time to change his mind.

No sooner had the words left his mouth than his mind begins warning him.  ‘You’ll be sorry,’ he keeps thinking.

“OK, here’s my first Wee Winky Willy,” Luke said.  “Since we’ve been hanging out here the last couple of months, I think you should be naked and stay that way until you leave,” he said with a giggle.

Willy gasps.  “What?”

“Sounds reasonable to me,” Trisha said, grinning.

For the first time it hit home Trisha would see him naked.  Will doesn’t know why it came as a surprise as that’s precisely what we had been talking about.  Somehow the idea of maybe being naked in front of the two of them seems far different from reality.

“Come on, Willy,” Luke said.  “You know we’re both going to be seeing a lot of you naked from now on, so you might as well start getting used to it.  There’s no time like the present.”

Trisha said somewhat coldly, “Or you can refuse, and it’s over before it ever started.”

Will’s heart starts pounding as he slips off his t-shirt.  He just somehow thought he’d have more time to mentally adjust to this before actually doing it.  When he has everything off except his underwear, Will gazes at Trisha one last time.  Her eyes are sparkling.  Trisha had never seen Will naked before, and she’s obviously relishing the thought.  The skinny boy closes his eyes and slips his boxers to the ground and steps out of them.  When he opens his eyes, Will sees they’re both staring at his privates.  He feels weird.  They keep him standing there as they silently stare at his dick.  The tension is almost unbearable.

Trisha smiles, nods her head, and just simply said, “OK, you do have a tiny dick, big deal.  I knew already anyway.”

“You knew?” Will asks with raised eyebrows.

“Yeah, this isn’t a big town, and people talk.”

“Who told you?” Will asks.

“Joanne Petersen did a while ago,” Trisha said.  “You tried to hook up with her at Malcolm’s party, remember.”  Will nods.  “Yeah, so she told me you had a tiny dick, and I see she wasn’t exaggerating.”

“So, how you going, little guy?” Luke asked playfully.  “You think you can do it?”

Trying to sound brave, Will said, “Yes, I think so.”

“Good,” Luke said as he picked up Will’s clothes.  “You won’t need these for a while, so I’ll put them in a safe place.  Come on, Trisha,” he said as they head for the back door of the house.  “We’ll be right back.”

“WAIT.  What about your family.  What if they find me out here like this?” Will asks in a panic.

“Oh, I’m sure you’ll think of something clever to say,” he said with a laugh as they enter the house.

As Will continues to ponder the change in their friendship and what this new dynamic will mean, time passes.  Ten minutes pass, and neither of them returns.  Will can’t leave, so he just sits by the fire and waits.

Finally, he heard footsteps at the back of the house.  The door opens, and he stands to chastise his friends for leaving him so long.  Luke’s mother comes out carrying a washing basket.  Her eyes widen when she sees him standing naked a few feet from her.  When the boy gets over the shock and sees she’s looking at his privates, he quickly covers himself with his hands.

“I’m sorry, Willy,” she said politely with a smirk.  “I didn’t realize you were out here. Um, where’re your clothes?”

“Um, we’re gonna go swimming, and Luke has gone in to get me some bathers to borrow,” he said, trembling all over.

“Luke told me you like going skinny dipping.”

His heart skips a beat at her question.  “Ah, yes, ma’am,” said nervously.

“I woulda thought you were too old for that now,” she said as she places the basket on the ground and takes off a shirt.  She then suddenly stops peers at his hands over his crotch, smiles, then said, “Well, maybe not.  I see one part of you has never grown up.  Am I right?”

“Yes, ma’am,” Will said.

“I don’t think any of Luke’s bathers would be suitable for you.  They’d be…too baggy in the front.”

Will blushes.

“Oh, you don’t need to be embarrassed.  I think it’s good to have a healthy self-image.” She then went back to taking clothes off the line.

“Ah, this would work,” she said and holds a bright pink bikini bottom she just took off the line.  “This belongs to my daughter, but I’m sure she won’t mind you borrowing them.  Try them on and see if they’ll fit.”

Luke’s mom tosses them to him playfully.  He has to move his hands away from his privates to catch them, affording her another unobstructed view.  She stands there patiently as he steps into them and struggles to pull them up.  They’re tight, but he’s resolved to get into them if for no other reason than to cover himself.  Will has to be extra careful when he gets them just below his testicles to avoid hurting himself.  Finally, with a few bends and a couple of small jumps, Will manages to get them on.  Luke’s mom stares at him and laughs.

“I know they’re a bit small for you,” she said apologetically.  “But you seem to fit the front nicely.”

When he glances down, he can’t see the outline of his penis and testicles straining against the tight material.  Still, there’s a smooth curving of the pink fabric, making it appear as if he has no genitals.

Luke’s mom must’ve noticed, too.  She smiles.  “Yes, they suit you nicely.  Have fun outside and be safe.”

After the last of the clothes are in the basket, she turns to leave but not before having one last look at his crotch.  Once she’s gone, Will lets out a sigh of relief and plops on the chair.  His heart races as he recounts in his mind what just occurred.  Suddenly he hears footsteps, and Trisha and Luke appear, both laughing heartily.

Will stands.  “What the fuck guys,” he shouts.  “Luke’s mom just got an eyeful of my cock.”

“I wouldn’t call that thing you’ve got a cock,” Trisha said and smirks.

I thought you were supposed to be naked whenever you’re here?” Luke asks, laughing.

“I was naked when your mom caught me,” Will said in his own defense, to which they both laugh all the more.

“That must’ve been embarrassing,” Trisha said.  She then walked around checking out his pink bikini bottoms.  “Take that thing off,” she orders, still giggling.  “You look like a girl.”

As will struggles to remove the tight bikini bottoms, they laugh loudly at him.  Once it’s off, Luke picks it up and says, “When my little sister hears you had these on, I suspect she’ll never wear them again.  I wonder why mom made you put it on?”

“Maybe she just wanted to see him in it,” Trisha said, giggling.

As Will stands naked before them again, he becomes a little embarrassed.  He shudders to think of what these two are going to put him through after this experience.

Trisha moves around him as if conducting some kind of inspection.  “You know, the fact you have basically no hair anywhere on your body lends itself to some pretty interesting scenarios.”

“What?” Will asks.

“Well, just look at yourself.  You aren’t that tall, and without any hair anywhere, you look a lot younger than you really are.  But the best part…” she said, stopping to stare at his genitals, “is your penis is so small that it just adds to the illusion that you’re a young boy.  You really do look like a prepubescent boy.”

“A prepubescent boy with a small dick,” Luke said and laughs.

“Oh, stop making fun of me.  I can’t help the way I was born,” Will snarls.

He is indeed shorter than they, but he never thought of it as a handicap.

“Trust me.  I’m not making fun of you,” Trisha said and then gives him a soft smile of admiration.  “You better get dressed,” she said, signaling Luke to toss Will his clothes.  “It’s almost time to go home now.  Besides, if Luke’s dad comes out here and sees you like this, he’ll probably whoop your ass.”

“Or die from laughing,” Luke adds, making Will groan.


This is a free sample from ‘Wee Winky Willy’ an SPH novella by Max Swan. Buy the eBook to read this amazing story.


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