Willy's Upcumming Performance
Posted: Sun Dec 10, 2023 7:45 pm
(This is a collaborative story with DCTreshPender)
"William! William! Wake up William!" I heard as my mother began to shake me in an effort to get me to wake up. My eyes shot open trying to see what the whole commotion was all about, I quickly mumbled,
"...What?" As I turned, wondering what on earth was going on.
"William! We really need to get going, get in the shower and get ready! Remember, we need to pick and get you sized up for your costume!"
Crap yeah! In the upcoming two weeks I was meant to be in the school play. Up on stage in Roman attire. A toga of sorts. The school directed us to a special costume shop that had virtually anything and everything we could need for this play.
"Me and your sister will be downstairs waiting for you to get ready so we can go!"
I forgot that Cassie was tagging along, she started to act like a right pain recently so I hoped that that wasn't something I had to handle later on.
When mother left I quickly made my way to the shower, did my routine and was out. I'd have liked to have spent a bit of time dealing with a certain morning situation but I just didn't have the time. I didn't need someone barging in and asking me to hurry up and witness a different type of performance.
We made our way to the costume store when I had a very unfortunate realization. In my hastiness, I had forgotten the one thing I definitely should not have, my boxers. Yep, I was currently comando underneath my shorts, I just had to hope that there were changing rooms there.
When we got into the store it was instantly clear just how many options there were going to be, it didn't seem to be that big a store, but there were tons to select from. Me and Cassie started to look around as Mom spoke to the 30 or so year old woman manning the desk.
While looking at what options there were, Cassie decided it would be extremely funny to pick up a princess tutu and put it a foot away from my waist as if to suggest it would be a perfect fit for the play. She even gave them to me to hold while she went to grab her phone for a picture to where I instantly put them back on the rack she had found them on to her clear disappointment.
I stuck out my tongue and told her,
“Just because I am to be a ‘fairy’ doesn't mean I am playing a girl!”
She smiled even more stating,
“Oh my apologies O Fairy Godfather, how ever could I have forgotten you were clearly a boy! Perhaps we should get you one in blue?”
To this I slightly flipped her off and sadly was caught by mom who looked at me with squinted eyes and muttered,
“William, behave!”
From behind her the woman manning the till came, holding a bag of what could be described as a couple try on options for the given role I had. She smiled at me and with outstretched arms gave me the see through plastic bag with a bundle of costumes inside and stated.
“There you go young man…Now if you'd like to follow me to the changing rooms I will aid you in trying things on. “
Trying things on? But he had no underwear? Crap, of all days! Perhaps he could talk himself out of it? Perhaps he can talk himself into trying things on by himself. He doesn't want some random woman to see his junk, no way!
The changing rooms were standard looking. A mirror inside to see yourself and a blind of some sort, to keep eyes from peering inside.
“I can do this myself, I don't think I need any help!” I exclaimed in a false sense of confidence as I tried making my way inside.
That was when the woman's hand latched onto my arm and raised her voice in a soothing manner.
“Sir, we were sent costume requirements by your school and I carefully hand picked some of our best costumes for you to try on and for you and your family to decide on the best one. You will only be keeping one of them and because of that I don't want you to pick one you don't know how to put on correctly or at worst damage one of the costumes!”
“William, stop being difficult and just let the woman go with you! What's the issue?!” Mother shouted.
“Yeah Willy, just stop being difficult!” Cassie parroted.
I tried to formulate a reason why I couldn't, why this was going to be embarrassing. I couldn't tell them and in defeat I headed in with the woman in tow, at least she closed the curtain behind us.
The woman wasted no time in getting out the first costume and it was moving way too fast for me! I didn't know how to react or what to say. All I knew is I couldn't strip in front of her.
“Can I try the stuff with my shorts on?” I asked softly.
She looked at me like I was an idiot,
“What of course not, I even need to measure you for a snug fit, those shorts are way too baggy anyways. Now get them off please so we can start!”
I had to come clean, I had to tell her I didn't have any underwear on. That I couldn't go strip my shorts off. I hoped she would understand my plea.
“Oh…. I see… hmmm… No bother, no bother at all. Costumes in such a manner are actually better off and better fitting when the person wearing them has nothing else on underneath, everything will fit smug I assure you!”
With nothing at it, and no where to really hide in the cramped dressing room, I pulled my shorts down slowly. Revealing my bare pubis and slowly but slowly the root of my cock and balls. I took a big breath and quickly rolled them down and stepped out of them. The woman didn't even take her eyes off me and stared probably in confusion about the lack of pubes, but oh well. I quickly try to pry the costume out of her hands but that didn't work as she quickly got on her hands and knees and asked me to raise my foot so she could get the blue tights on. I was covering my crotch but she gave me the matching frilly shirt. I had no choice but to remove my hands, once again exposing myself, and put the shirt on. Even though I couldn't see her eyes on me, I could feel them and it didn't help that she had to add in.
“You are very endowed for a boy your age, but you look way younger there than I would have expected, do you shave? Judging from that red face, I assume you do!” she smirked as I blushed hard. I just wanted this day to end.
After I was snuggly in costume the woman got out her tape and did various measurements if my waist and such. Even tugging at the outfit. I even saw her measure my crotch, I wanted to say something about that but all she said was.
“Hmmm. 4.5 inches… Wow, that might be an issue!” So I guess she was acting somewhat in my best interest?
I wanted to view the mirror before stepping out, to see what condition I am in but I wasn't able to as the woman dragged me out back into the view of my mother and Cassie. I saw their eyes roam over my body which sent a quick shiver up and down my spine. I could even see Cassie stifling a laugh.
“What what do you ladies think? He's a handsome boy, right?” she smiled while giving my shoulder a pat.
“Ok, how about a twirl?”
So I did just that, I gave a spin, a slow spin. I even caught my front in the mirror provided and looked in shock. The tights were indeed tight. I could see my junk, the outline of my dick, my foreskin and both of my balls were in clear view. My mother and sister both saw that. I turned around wide eyed as my sister could no longer contain herself.
“OH MY GOD! HAHA! YOU CAN BASICALLY SEE EVERYTHING! WAIT TILL THE GIRLS IN THE PLAY SEE!”
Mother didn't appreciate Cassie laughing at me but let it slide as she turned to the woman and said.
“That shirt is fine, but the tights look a bit… Constricting… Do you have any other types of bottoms for him?”
I looked down once again and looked in horror as I saw my dick starting to expand. I needed to run back in,so I did, brushing the woman's hand off of my arm and went into hiding before anyone noticed my predicament down below.
Lukcily the woman just took it as a sign that I agreed and laughed and followed me in stating,
“Oh of course, we will be back in a minute!”
Back inside the changing rooms I had a big developing dilema. What to do, I was getting more erect by the second and the woman was now fetching a different type of bottoms for me to wear. I couldnt let her see me in such a state, so I mentioned that I would take these bottoms and that would be that.
“What do you mean? Sir, even your mother agreed with you, I thought you ran into here looking to change into something else, why the full 180?”
I didn't know what to say as she started to roll down the tights. I was frozen. Trying to cover as she removed my hands. I couldn't fight it. I couldn't until…
*Thump*
She, with a lot of resistance finally got the tights down below my semi erection which jumped up slamming the woman in the chin, her lips and her nose before hovering horrizontal, pressing itselt against her nose.
She seemed shocked, I seemed shocked. Time seemed to pause for a full minute before she ignored it and went back down to rolling them off my feet. I was now bare again down there. And rapidly growing. By the time she had gotten out my other bottoms it was standing up, rigid and the head popped out of my foreskin on its own. It looked downright angry, veiny and seemed to bob with the beat of my heart. I was trembling as the woman's eyes looked into my own and a smile appeared along her face.
Before she put the bottoms on she once again pulled out her measuring tape, she brought it up to my cock and measured the length. I let her, what else was I supposed to do? 7.2 inches she read aloud. I wanted to curl up into a ball and run disappear, but that wasn't to happen. She raised my feet and slide up what I assumed were shorts at first. My boner once again nudged her in her face.
When the ‘shorts’ got rolled up, I realised just how bad it was. They weren't shorts. It was a similar kilt to the one that sister held up earlier. I thought it was a tutu but it wasn't. It was clearly more ‘masculine’ but none of that mattered as my skyward erection push it away and was completely visible. If I were soft it wouldn't have been bad, but completely commando and fully erected meant I had no chance.
“Please don't make me go out there like this!” I quietly begged the woman.
She seemed to be in thought, thinking how to proceed. That was when mother came outside asking what was taking so long.
I shook my head at the woman, eyes wide, as if begging her not to say but she couldn't delay it long.
“Oh just a problem!” She returned.
“Problem, so I need to come in there? Is everything ok?”
It was clear she didn't know what to say. If I had a problem, it was clear mother would need to know.
“Your son is… errr…your son is suffering a… Er… You son is suffering an erection, and it's very visible!”
My mother sounded dumbfounded, she didn't know what to say,
“Come out here now William!”
“Mom you are going to make him come outside, didn't you just hear what the woman said?!” Cassie giggled.
I tried to refute but mom just retorted by saying.
“Come out now William or I will make you come out myself!”
I lost the battle and awkwardly stepped out, sealing my fate. My mother and my sisters eyes shot wide open as they looked me up and down. No laughter, no noise, just shock. Cassie had to end up breaking the ice though, because of course she would.
“HAHA, MY BROTHER HAS A MASSIVE COCK!!” This earned her a slight whack from my mother to the back of her head.
I was bombarded with questions, how on earth I was here butt naked and such how I was displaying myself in such a manner infront of random people.
At least the woman stood up for me and told mom that it was actually better to wear the costumes while being bare underneath.
“We will take them all. Every costume you have in that bag we will take it all to excuse for my sons public display.”
I tried to say it wasn't my fault, even my erection had died down at this point.
Safe to say that my drive home was the most silent one I had ever experienced in my life.
"William! William! Wake up William!" I heard as my mother began to shake me in an effort to get me to wake up. My eyes shot open trying to see what the whole commotion was all about, I quickly mumbled,
"...What?" As I turned, wondering what on earth was going on.
"William! We really need to get going, get in the shower and get ready! Remember, we need to pick and get you sized up for your costume!"
Crap yeah! In the upcoming two weeks I was meant to be in the school play. Up on stage in Roman attire. A toga of sorts. The school directed us to a special costume shop that had virtually anything and everything we could need for this play.
"Me and your sister will be downstairs waiting for you to get ready so we can go!"
I forgot that Cassie was tagging along, she started to act like a right pain recently so I hoped that that wasn't something I had to handle later on.
When mother left I quickly made my way to the shower, did my routine and was out. I'd have liked to have spent a bit of time dealing with a certain morning situation but I just didn't have the time. I didn't need someone barging in and asking me to hurry up and witness a different type of performance.
We made our way to the costume store when I had a very unfortunate realization. In my hastiness, I had forgotten the one thing I definitely should not have, my boxers. Yep, I was currently comando underneath my shorts, I just had to hope that there were changing rooms there.
When we got into the store it was instantly clear just how many options there were going to be, it didn't seem to be that big a store, but there were tons to select from. Me and Cassie started to look around as Mom spoke to the 30 or so year old woman manning the desk.
While looking at what options there were, Cassie decided it would be extremely funny to pick up a princess tutu and put it a foot away from my waist as if to suggest it would be a perfect fit for the play. She even gave them to me to hold while she went to grab her phone for a picture to where I instantly put them back on the rack she had found them on to her clear disappointment.
I stuck out my tongue and told her,
“Just because I am to be a ‘fairy’ doesn't mean I am playing a girl!”
She smiled even more stating,
“Oh my apologies O Fairy Godfather, how ever could I have forgotten you were clearly a boy! Perhaps we should get you one in blue?”
To this I slightly flipped her off and sadly was caught by mom who looked at me with squinted eyes and muttered,
“William, behave!”
From behind her the woman manning the till came, holding a bag of what could be described as a couple try on options for the given role I had. She smiled at me and with outstretched arms gave me the see through plastic bag with a bundle of costumes inside and stated.
“There you go young man…Now if you'd like to follow me to the changing rooms I will aid you in trying things on. “
Trying things on? But he had no underwear? Crap, of all days! Perhaps he could talk himself out of it? Perhaps he can talk himself into trying things on by himself. He doesn't want some random woman to see his junk, no way!
The changing rooms were standard looking. A mirror inside to see yourself and a blind of some sort, to keep eyes from peering inside.
“I can do this myself, I don't think I need any help!” I exclaimed in a false sense of confidence as I tried making my way inside.
That was when the woman's hand latched onto my arm and raised her voice in a soothing manner.
“Sir, we were sent costume requirements by your school and I carefully hand picked some of our best costumes for you to try on and for you and your family to decide on the best one. You will only be keeping one of them and because of that I don't want you to pick one you don't know how to put on correctly or at worst damage one of the costumes!”
“William, stop being difficult and just let the woman go with you! What's the issue?!” Mother shouted.
“Yeah Willy, just stop being difficult!” Cassie parroted.
I tried to formulate a reason why I couldn't, why this was going to be embarrassing. I couldn't tell them and in defeat I headed in with the woman in tow, at least she closed the curtain behind us.
The woman wasted no time in getting out the first costume and it was moving way too fast for me! I didn't know how to react or what to say. All I knew is I couldn't strip in front of her.
“Can I try the stuff with my shorts on?” I asked softly.
She looked at me like I was an idiot,
“What of course not, I even need to measure you for a snug fit, those shorts are way too baggy anyways. Now get them off please so we can start!”
I had to come clean, I had to tell her I didn't have any underwear on. That I couldn't go strip my shorts off. I hoped she would understand my plea.
“Oh…. I see… hmmm… No bother, no bother at all. Costumes in such a manner are actually better off and better fitting when the person wearing them has nothing else on underneath, everything will fit smug I assure you!”
With nothing at it, and no where to really hide in the cramped dressing room, I pulled my shorts down slowly. Revealing my bare pubis and slowly but slowly the root of my cock and balls. I took a big breath and quickly rolled them down and stepped out of them. The woman didn't even take her eyes off me and stared probably in confusion about the lack of pubes, but oh well. I quickly try to pry the costume out of her hands but that didn't work as she quickly got on her hands and knees and asked me to raise my foot so she could get the blue tights on. I was covering my crotch but she gave me the matching frilly shirt. I had no choice but to remove my hands, once again exposing myself, and put the shirt on. Even though I couldn't see her eyes on me, I could feel them and it didn't help that she had to add in.
“You are very endowed for a boy your age, but you look way younger there than I would have expected, do you shave? Judging from that red face, I assume you do!” she smirked as I blushed hard. I just wanted this day to end.
After I was snuggly in costume the woman got out her tape and did various measurements if my waist and such. Even tugging at the outfit. I even saw her measure my crotch, I wanted to say something about that but all she said was.
“Hmmm. 4.5 inches… Wow, that might be an issue!” So I guess she was acting somewhat in my best interest?
I wanted to view the mirror before stepping out, to see what condition I am in but I wasn't able to as the woman dragged me out back into the view of my mother and Cassie. I saw their eyes roam over my body which sent a quick shiver up and down my spine. I could even see Cassie stifling a laugh.
“What what do you ladies think? He's a handsome boy, right?” she smiled while giving my shoulder a pat.
“Ok, how about a twirl?”
So I did just that, I gave a spin, a slow spin. I even caught my front in the mirror provided and looked in shock. The tights were indeed tight. I could see my junk, the outline of my dick, my foreskin and both of my balls were in clear view. My mother and sister both saw that. I turned around wide eyed as my sister could no longer contain herself.
“OH MY GOD! HAHA! YOU CAN BASICALLY SEE EVERYTHING! WAIT TILL THE GIRLS IN THE PLAY SEE!”
Mother didn't appreciate Cassie laughing at me but let it slide as she turned to the woman and said.
“That shirt is fine, but the tights look a bit… Constricting… Do you have any other types of bottoms for him?”
I looked down once again and looked in horror as I saw my dick starting to expand. I needed to run back in,so I did, brushing the woman's hand off of my arm and went into hiding before anyone noticed my predicament down below.
Lukcily the woman just took it as a sign that I agreed and laughed and followed me in stating,
“Oh of course, we will be back in a minute!”
Back inside the changing rooms I had a big developing dilema. What to do, I was getting more erect by the second and the woman was now fetching a different type of bottoms for me to wear. I couldnt let her see me in such a state, so I mentioned that I would take these bottoms and that would be that.
“What do you mean? Sir, even your mother agreed with you, I thought you ran into here looking to change into something else, why the full 180?”
I didn't know what to say as she started to roll down the tights. I was frozen. Trying to cover as she removed my hands. I couldn't fight it. I couldn't until…
*Thump*
She, with a lot of resistance finally got the tights down below my semi erection which jumped up slamming the woman in the chin, her lips and her nose before hovering horrizontal, pressing itselt against her nose.
She seemed shocked, I seemed shocked. Time seemed to pause for a full minute before she ignored it and went back down to rolling them off my feet. I was now bare again down there. And rapidly growing. By the time she had gotten out my other bottoms it was standing up, rigid and the head popped out of my foreskin on its own. It looked downright angry, veiny and seemed to bob with the beat of my heart. I was trembling as the woman's eyes looked into my own and a smile appeared along her face.
Before she put the bottoms on she once again pulled out her measuring tape, she brought it up to my cock and measured the length. I let her, what else was I supposed to do? 7.2 inches she read aloud. I wanted to curl up into a ball and run disappear, but that wasn't to happen. She raised my feet and slide up what I assumed were shorts at first. My boner once again nudged her in her face.
When the ‘shorts’ got rolled up, I realised just how bad it was. They weren't shorts. It was a similar kilt to the one that sister held up earlier. I thought it was a tutu but it wasn't. It was clearly more ‘masculine’ but none of that mattered as my skyward erection push it away and was completely visible. If I were soft it wouldn't have been bad, but completely commando and fully erected meant I had no chance.
“Please don't make me go out there like this!” I quietly begged the woman.
She seemed to be in thought, thinking how to proceed. That was when mother came outside asking what was taking so long.
I shook my head at the woman, eyes wide, as if begging her not to say but she couldn't delay it long.
“Oh just a problem!” She returned.
“Problem, so I need to come in there? Is everything ok?”
It was clear she didn't know what to say. If I had a problem, it was clear mother would need to know.
“Your son is… errr…your son is suffering a… Er… You son is suffering an erection, and it's very visible!”
My mother sounded dumbfounded, she didn't know what to say,
“Come out here now William!”
“Mom you are going to make him come outside, didn't you just hear what the woman said?!” Cassie giggled.
I tried to refute but mom just retorted by saying.
“Come out now William or I will make you come out myself!”
I lost the battle and awkwardly stepped out, sealing my fate. My mother and my sisters eyes shot wide open as they looked me up and down. No laughter, no noise, just shock. Cassie had to end up breaking the ice though, because of course she would.
“HAHA, MY BROTHER HAS A MASSIVE COCK!!” This earned her a slight whack from my mother to the back of her head.
I was bombarded with questions, how on earth I was here butt naked and such how I was displaying myself in such a manner infront of random people.
At least the woman stood up for me and told mom that it was actually better to wear the costumes while being bare underneath.
“We will take them all. Every costume you have in that bag we will take it all to excuse for my sons public display.”
I tried to say it wasn't my fault, even my erection had died down at this point.
Safe to say that my drive home was the most silent one I had ever experienced in my life.