Ms.Smith

Rushing through the moving crowd John desperately began begging for anyone to "guide" him to the pool. A lot of people feigned ignorance, giving him responses like "You're such a pervert John." or "Seriously John? You're really that **** for a hand job." Others just straight up told him that they wanted to see him fail the challenge so he'd have to crawl the way back. Running out of time and all out of options John decided his best bet would be to ask someone who didn't know about the dare. Sadly that meant having to ask Megan's mother.

She was absent during the game and doesn't know about any of the commands he has to do. The only problem is if he out right told her about it the odds are she would deny him like everyone else had. John decided he had to get her to lead him without directly asking her, but how? John thought about all the times she had lead him by the dick before, and they all seemed to have one detail in common. She was always very angry with him.

John had to quickly decide which was worse, an angry Ms.Smith or crawling the whole walk back from the pool. It didn't take him much time at all to decide the crawl would be infinitely more humiliating. With that he made his way to Megan's mother who was standing by the front door counting off the final guests leaving her house.

Ok i'm just going to have to piss her off, seems like I'm a natural at that... John thought to himself as he approached tho woman by the door, only for his mother's voice to suddenly invade his mind. "If I hear one more bad thing about you i'll make sure you go to school with a red behind every day, understand John?!

Shit I can't make her too angry or she'll mouth off about me to my mom. I'm going to have to be careful about this... John needed to come up with a plan that would get her mad enough to give him an "escort" but not mad enough to cause a scene.

Feeling a tap on her shoulder Ms.Smith turned around to see a collard nude boy standing behind her.

"Ms.Smith, I-I really don't feel like going to the pool. Can't I just stay here until you guys get back?" John asked doing his best to sound **** and anxious. While John was talking he made sure to shift his weight to the tips of his bare feet while also moving his thighs ever so slightly forward. This left his 5.16 in. erect cock jutted out in a noticeably tempting way.

"No! Of course you can't Mr.Doe! This is my daughters party and if she wants you to go to the pool, you'll go to the pool." Ms.Smith responded, surprised that John would even think that was ever an option for today. John noticed that while Ms.Smith was talking her eyes had made a few quick glances down to the bare cock presenting itself before her.

Perfect I've got her right where I want here, now just to real it in... John thought to himself as he began slowly moving his hips back and forth, giving his dick a smooth hypnotic motion.

"Please Ms.Smith! I'm sure Megan will find a way to have fun without me, I promise I won't get into any trouble." John asked again the same tone a child would use to bother their parents.

"Mr.Doe! You are going to that pool! It is a part of your punishment now stop asking and get in line we're leaving." Ms.Smith said as she moved past him towards the front of the group.

Fuck gotta act fast or she'll get away!

"NO!" John announced stopping Ms.Smith in her tracks. Slowly turning around she looked him dead in the eyes.

"What did you just say..." The words were venomous, piercing right into John's soul. He knew he was on thin ice, but if he could just push her a little bit more...

"I said I'm not going! Why would I? All Megan is going to do is humiliate me anyway!" This wasn't entirely a false statement, making it easy for John to sound genuinely angry. It seemed to work at least somewhat as Ms.Smith turned back around and marched her way over to him.

"You are going to go John, there is no arguing about it!" Ms.Smith said leaning right into John's face.

"Why should I, huh? Why would anyone want to be paraded around naked in a public place with a group of horny teenagers?!" John spat back, pushing his face closer to the older woman's as well.

"That is part of your punishment young man! You humiliated my daughter and ruined her life when you stole all those panties, so i'm going to make sure the same happens to you tenfold! So get in line or so help me..."

"Fucking make me bitch!" John responded sharply, only to turn pale as soon as he registered what he had just said. Ms.Smith's jaw dropped and her hand suddenly returned around John's 5.16 in. shaft with a hard tug forward.

"WE ARE GOING TO THE POOL AND THEN YOU'RE GOING TO GET ON THE PHONE AND REPEAT WHAT YOU JUST SAID TO YOUR MOTHER!" Ms.Smith shouted catching the attention of the group who were now staring at the pair making their way to the front.

"No, OUCH! Please don't call my mom, OUCH! I promise I'll gAHHH! Please stop pulling my penis so hard Ms.Smith, I'm sorry!" John begged with tears in his eyes as he was pulled along. The party guests once again began laughing as John was dragged cock first through them to the front of the line.

"That boy just can't stop getting into trouble can he?" A girl next to Megan said in slight disbelief.

"Ahhh.. no he can't, and that's why I love him." Megan said with a smile as she moved her phone to record her mother dragging her teary eyed "best friend".

The walk to the pool should take no longer than twenty minutes, but to John every five minutes that passed felt like an hour. Megan's mother was showing him no mercy with her grip, and always giving him sharp tugs whenever he so much as fell slightly out of pace with her. Any protest that John made were always met by silence or sharp stares. Of course the humiliation didn't just end with being dragged around by his best friends mother. John could could clearly hear soft whispers and laughter coming from the group behind him.

Arriving at the gates to the pool John held his breath. Hopefully over the course of the walk Ms.Smith had settled down and would allow him to go without a call to his mother. Stopping at the gate Ms.Smith called everyone to gather around her. As the circle of party guests formed around them John felt the humiliation of being handled by the cock burning up.

"Before we go into the pool everyone I have something special I'd like for you all to see." Ms.Smith said giving John a quick look straight into his eyes. "As you could all tell John here is in a little bit of trouble, and is due for a call with his mother. I thought it would be fun if you all listened in..."

"WAIT WHAT?!" John yelled in surprise as cheers of approval came from the group. "Please Ms.Smith i'm sorry, don't make me do this." John tried begging one last time.

"Nope I don't want to hear it John." Ms.Smith shot down John before returning her focus to the group. "Now everyone be quite, and could Megan please come join me."

Megan was practically bouncing with joy as she emerged from the crowd. "Yes mom? How can I be a help to you?" Megan said in a very happy singsongy tone with a big smile. She made sure to give John a quick look in the eyes as a physical way of saying "i'm really enjoying the humiliation you're being put through right now."

"Sweetie could you please hold John while I call his mother?" Ms.Smith asked, not that she even needed a response as Megan's smooth hands quickly replaced her mothers around John's cock.

"Don't worry mom, i'll make sure he doesn't run off anywhere..." Megan responded as her hand began to idly move up and down the nude boy's shaft.

Pulling out her phone Ms.Smith began to tap away, releasing a loud ~beep~ with every number she hit, however before she could finish a voice from the group of guests shouted out "Wait a second Ms.Smith!"

Looking up from the phone Ms.Smith watched as Therisa May emerged out from the front row of party guests. Running up to the older woman Therisa held out her hand and presented a cylindrical speaker.

"You should hook up to my Bluetooth speaker... You know, so the people in the back can hear..." The nerdy girl said in a shy voice. The exchange left a lot of people a bit shocked, Ms.Smith included. Therisa didn't seem like the type of girl to get off to something like this, but here she was actively playing a part in making John's humiliation even worse.

You've got to be fucking kidding me. John thought to himself as Ms.Smith grabbed the speaker from her hands and began trying to pair it to her phone.

"Thank you Therisa, i'm sure the people in the back will be very thankful." Ms.Smith said in an approving tone, sending Therisa back into the group. Returning to her phone she finished dialing John's mother's number, except this time the loud beeps of her hitting the dial pad numbers were amplified out the small speaker.

Pressing the final digit, Ms.Smith held the phone up to her head as a few rings exited the Bluetooth. Before long the familiar voice of Ms.Doe echoed out of the speaker with a simple "Hello?"

"Hello Ms.Doe, it's Megan's mother speaking. I regret to inform you your son has gotten into a little bit of trouble again..." Ms.Smith said in a stern disappointed mother voice.

"Oh my god what did that boy do this time?!" John's mother's tinny voice projected through the speaker in an angry tone.

"Well unfortunately John had decided to use some inappropriate language against me, and while I'd love to tell you more about what he said i'm sure you'd prefer to hear it from John himself..." Ms.Smith said as she leaned into John and held the phone in front of his mouth.

"John please call your mother exactly what you called me..." As if on queue Megan gave John a quick tug on the dick sending him stumbling closer to the phone.

For a brief moment John paused, unable to bring himself to repeat what he said earlier because he knew the storm of anger it would bring out of his mother. As soon as that brief moment turned into a noticeable pause however Ms.Doe's voice returned from the speaker.

"Well go on then John, i'm sure whatever you called Ms.Smith you'll have no problem calling your mother... right?" Ms.Doe said as she began to grow annoyed at her son's hesitance to do what he was ordered.

Giving a nervous gulp John opened his mouth. "Mom... You're a fucking bitch."

"EXCUSE ME?!" Ms.Doe gasped, setting off a round of snickers from the party guests who was trying their best to remain discreet.

"Mr.Doe that is not language you should be using AT ALL! Let alone to the person who has invited you into their house!" John's mothers voice boomed through the loudspeaker. "When you get home i'm going to make sure your firm ass is as red as the sun! I swear I'm going to go buy a paddle for you if you keep this up!"

"Please mom don't spank me again!" John suddenly interjected as his hands instinctively moved to cover his naked butt.

"Oh stop pretending like you're not asking for John! I saw what you did after the spanking I gave you this morning! You ran back into your room and began rubbing your hard cock against your pillow!" Ms.Doe's voice boomed to the crowd who lost it and began laughing aloud.

"YOU SAW THAT?!" John shouted as his face turned dark red.

"Yes I saw that! I see everything you do in your room there are cameras everywhere in the house! That's a part of being in N.A.K.E.D!"

John didn't even know how to respond, he simply stood there mouth wide open as his mother began to speak again.

"You know what John it seems to me that your getting off to this whole N.A.K.E.D situation. I saw how your dick got hard as soon as we walked out into public, and don't think for a second I didn't notice your cock getting especially hard when I started spanking you in front of those cheerleaders! I think you even enjoyed it when I spun you around and gave those cheerleaders a little show by spanking your cock around!" Ms.Doe announced, sending the crowd into a hysterical laughing fit. At this point even Megan and let go of John's cock as she fell over laughing.

"THAT'S NOT TRUE! I'M NOT GETTING OFF TO THIS AT ALL!" John defended himself as he shouted back into the phone, but his defense fell on deaf ears as the group was to busy laughing to hear him.

"I'm not sure I believe that John, in fact I think i'm going to take my name off your release contract until you prove to me you've matured out of this behavior... And whats all that noise I'm hearing?!" Ms.Doe questioned.

Before John could respond Ms.Smith pulled the phone away from him. "Oh sorry did I forget to tell you that I put you on speaker Ms.Doe? Opps, well at least everyone at the party seems to be enjoying those little stories you just told."

"I see, no problem Ms.Smith I'm glad everyone could find some humor from this situation." Ms.Doe responded.

The two mothers continued to speak for a little bit but John didn't bother to pay attention to what they said, he was to busy thinking about what his mother had just said. She's going to take her name off his N.A.K.E.D release contract until he can convince her he's not a pervert. Which will be near impossible with all the shit Megan is making him do.

"Well thank you for talking to him Ms.Doe."Ms.Smith said calmly as everyone at the party seemed to be recovering from their outbursts.

"It's no problem Ms.Smith, I'm so sorry for the trouble he's caused you. Are you sure you don't want me to come pick him up?" Ms.Doe asked in a defeated tone.

"No, no. It's no problem really, besides my daughter is really enjoying her time with him." Ms.Smith said giving her daughter a quick glance to see her wiping tears of laughter from her face.

"Well thank you for dealing with him. Feel free to punish him for this however you see fit." John's mother responded, giving Ms.Smith a nice big smile.

"Don't worry I will Ms.Doe, I'll call you when he's ready to be picked up... or whenever he misbehaves again." With that Ms.Smith clicked the phone and as a cheer rang out from Megan's friends.

"Well I hope you all enjoyed that, feel free to make your way into the pool! Me and John here still have some unsettled business we need to attend to." Ms.Smith announced as her hand returned to its firm grip around John's cock.

As the party guests passed they made sure to give their off comments to John who stood next to Megan's mother as she counted off everyone going in. Before long he was once again alone with both Ms.Smith and Megan who was instructed to stay behind as well.

"Well then Mr.Doe it seems a punishment is in order for your behavior, and Megan here has the perfect idea for you..."