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Chapter 2
by CupCup
Where shall I be embarrassed?
Dinner Party!
Kaylee had done me the favor of organizing a dinner party with a few of my favorite gals. She had invited over my old teacher Mrs. Peck along with Mrs. Wilson. She had taken care of all the cooking, leaving me to plan out my next humiliation.
I was called down to the dining hall and met with an enormous feast. Mrs. Peck and Mrs. Wilson were both wearing lovely dresses. They appeared to be expecting this to be a formal event. In contrast I was wearing simple jeans and a polo. They didn't seem to mind, but I felt a bit out of place. We all took our seats and began to eat.
Mrs. Peck was the first to speak, "So Kaylee tells me of a new punishment tactic you've been working on?"
I looked confidently up and said, "Yes, it is specifically designed to punish the worst misbehavior of them all: masturbation. I beleive everyone at this table has been guilty of it from time to time and it must be stopped. Not including yourself of course." Mrs. Peck blushed at the mention. "It is a simple way to keep us all honest. If one of us catches another then we are subjected to absolute humiliation.
Mrs. Peck's eyes lit up, "Oh? And just what do you mean by that?"
"Well it is quite simple. Say I catch Kaylee in the act, masturbating like some sort of pervert. I can then bring it up at the next time of my choice. She then immediately has to strip naked and masturbate again."
Mrs. Peck was in disbelief, "Oh my lord! What if you were to bring it up in public?"
I grinned as I said,"That would make it all the more memorable! Hopefully then the pervert will associate the disgusting act with humiliation!"
Mrs. Wilson looked uncomfortable, but Kaylee had a big smile on her face the entire time. Mrs. Peck continued to question, "Have you had any of these punishments so far?"
"Not yet, but I expect this horrible practice has stopped throughout the house since we've implemented this new rule."
Mrs. Peck's eyebrow raised, "So you're saying you haven't... well you know?"
I feigned shock, "Well no of course not! I would never dare to masturbate with such a punishment on the line!"
Kaylee spoke up, "And you wouldn't lie right? If you were lying you would have to jerk off right in front of your old school teacher!"
I stood studdenly, "Of course! I am an honest man and no pervert!"
Kaylee stifled a giggle and pulled out her phone, "Great to hear! Now could the entire table check out this video?" Almost immediately I was met with the audio of myself moaning. Clear as day her video was showing my in my bedroom jerking off roughly as I held a pair of Mrs. Wilson's panties to my face. I was moaning the name "Oh Mrs. Wilson!" over and over. It looked as if she was filming me from out in the hall.
Kaylee had a look of cruel satisfaction, Mrs. Wilson a look of disgust, but Mrs. Peck had a smile from ear to ear. I looked down in shame, "I am so sorry, I didn't think anyone would notice."
Kaylee smiled, "Well come on now! What were all those rules you had?" She turned her phone to video mode and began filming. "You're going to start by getting naked and then what?"
Looking directly into the camera I said, "And then I'm going to masturbate," my eyes darted to Mrs. Peck, "in front of all of you." I started by removing my polo and revealing my chest to the room. As I did Mrs. Wilson looked unimpressed. At this point I think she knew this was all my plan. My cock was already hard by the time I unbuckled my pants and began lowering my zipper. Wearing no underwear, it flopped out for all to see. Mrs. Peck's eyes lit up and she let out a gasp. "Oh my god this is so humiliating." I began to stroke my shaft. "I can't believe my school teacher knows what my penis looks like. She will probably tell all her friends, and maybe some of my old classmates!"
As I continued to stroke I walked my way closer to Mrs. Peck. I knew I wanted to finish on her, but I wanted to see how far I could push it. I came closer to her until I was within arms reach, pumping my shaft right in front of her face. I reached out and pulled one strap of my her dress down her shoulder, letting to top of her breast come into view. Mrs. Wilson rolled her eyes and whispered, "Oh my lord."
Mrs. Peck shot me a devious look, "Oh is that how this is going to go?" I pulled her other strap down, letting her cleavage spill out for all to see. I nodded as if I was unable to speak. I continued jerking off, periodically pretending to brush the head of my penis against her lips. Each time she would make an exaggerated glance at me, "My my you're taking this punishment seriously!" I nodded my head and reached for the top of her dress. It was clear she wasn't wearing a bra.
I slowly reached my hand down to the top of her dress and began to pull. The top of her breast came even more into view and I saw hints of her nipples when suddenly Mrs. Wilson called out, "WAIT!" We all turned to her holding out a phone of her own. "I have something for you all to see as well!"
It was a video, taken in the front hall. It appeared to show Kaylee sitting on the front chair facing the window, completely naked. She had one hand rubbing her crotch and another hand holding a pair of panties to her face. She was moaning the same thing I was, "Mrs. Wilson! Mrs. Wilson!" Kaylee gave a shocked look.
"How did you get that?" She stammered, "I thought everyone was out of the house!"
Mrs. Wilson put her hand on her hip, "Well tomorrow you'll need to clean that chair twice, but for now I think you should join our sir's state of clothing." Kaylee's eyes went wide. She put down her phone that had been recording, but I noticed she didn't turn it off. Propped up by her dinner plate it still had a perfect view of me.
"Well at least its not in front of any teachers I used to know." Kaylee said with a wink to Mrs. Peck. She slowly began to disrobe and I started to stroke my cock again. By the time she was completely naked I was fully erect again. Her blonde bush was wet and she began to rub herself.
Mrs. Peck leaned back in her chair and folded her arms, "This seems to be quite and effective punishment, you both look mortified!"
As Kaylee rubbed and moaned she began to grind her crotch against me. Both our young naked bodies were on display for these two cougars. Kaylee's moans seemed to be getting quicker and I knew she was getting close. I decided to enact my final plan and yelled, "WAIT!" All three women looked at me concerned. "Mrs. Peck can you please look at my phone. Its there on the table." She reached over and unlocked it. "Check through the photos and videos, there should be one from last night." I saw Mrs. Wilson's eyes go wide. I also knew Mrs. Peck would be scrolling through countless naked pictures I had taken of myself earlier this morning. Based on her face she didn't seem to mind. Finally she began to play a video at full volume. It was the sound of Mrs. Wilson moaning. Before we could see the video footage Mrs. Wilson snatched up the phone.
"Yes, yes, I am guilty as well. No need to play the whole thing!" Her dress didnt have straps, so in one quick motion she was able to pull her dress down to her ankles. To no one's surprise she was not wearing a bra or panties. Her thick dark bush was a tangle of beauty. Her nipples were seemingly already hard. In a few quick strides she joined us in view of Mrs. Peck and the camera phone. Almost annoyed, she began to masturbate along with us.
Mrs. Peck grinned and bit her lip. "You must be so embarrassed to be naked in front of these two younger cuties huh?" Mrs. Wilson looked uncomfortable but continued to rub herself. "I can't imagine what it must be like to be so exposed. Every day you talk to them they will no doubt be imagining those large nipples and that hairy pussy!" I saw Mrs. Wilson's face turning red.
I walked around behind Mrs. Wilson and pressed my body against hers, "She's right you know. At this point I don't even know why you both to wear clothes at all. I slipped my cock between her cheeks and pressed myself at the entrance to her pussy. She shifted uncomfortably but did not stop me. With both my free hands I reached around to fondle her breasts. Pinching each enormous nipple at a time I felt her winch. I then guided her toward Mrs. Peck, one step at a time until we were directly in front of her. The entire time Kaylee was rubbing herself, seemingly enjoying the show. I grabbed Mrs. Wilson's hand that wasn't busy and guided it to Mrs. Peck's dress. Using both our hands, I pulled down revealing Mrs. Pecks huge breasts. "They're even bigger than yours! Is someone jealous?" Mrs. Wilson hid her gaze in shame.
Mrs. Peck was loving it, "You look so uncomfortable! HA!" I then took Mrs. Wilson's hand and continued to pull Mrs. Peck's dress until it made it all the way down her waist, leaving her in a small pair of pink panties.
"Wow she even wears panties! Unlike you!" At that I heard Kaylee let out a load moan as she orgasmed. "Now Mrs. Wilson, bent down and take off her panties with your mouth!" As she bent down my cock strained against her pussy. She grabbed both of Mrs. Peck's thighs and she knelt closer and bit the top of her panties. As she did I shoved my cock inside her. She let out a gasp, losing her grip on Mrs. Peck's panties. "No no! You need to take them off silly! Not just touch them!" I could feel the humiliation radiating off Mrs. Wilson as I continued to fuck her.
With each pump I seemed to knock her off balance before she finally got a hold of the panties. With great struggle she worked them down her thighs, revealing Mrs. Peck's beautiful, shaved pussy. At this point I began ramming myself even harder into Mrs. Wilson, causing her face to be shoved into Mrs. Peck's crotch. Kaylee had grabbed her phone and was now standing there naked shoving the camera into Mrs. Wilson's face. "Like that?" She taunted her as I contunued thrusting. Mrs. Wilson let out a moan and I felt her pussy tense up around me. She buckled over as she orgasmed and reached up to grab Mrs. Peck's breasts.
Almsot in unison I finally finished as well, pumping my maid full of hot cum. I let out a long moan and squeezed Mrs. Wilson's breasts tightly. We both collapsed to the ground exhausted.
Mrs. Peck seemed out of breath as well and said "You have GOT to send me that video dear!"
Kaylee tried to collect herself and said, "Can do!" Her hands seemed to be shaking as she clicked the buttons on her phone. "See? Sent."
Mrs. Peck put a hand over her mouth, "Uh sweetie? I think you may have just sent that to ALL contacts!" All four of us turned to look up at the phone and confirm to our horror.
The phone read, "Mass text successfully sent to: ALL CONTACTS."
Mrs. Wilson collapsed again and shuddered, "Oh dear God no."
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