Chapter 50
by Anonstorywriter
What is my punishment?
Kayla's Third Rule
I had barely understood what was happening before Christopher was on me. He quickly pushed me back towards the bed, sat down, and pulled me over his lap. The fuck was happening?!
“Maddison, I think you’ll find this punishment fairly straightforward. I think you’re gonna love it too, but that’s just the fun part.” His hand was playing with my naked ass as he spoke and I found my hips moving back and forth, enjoying the feel of his hand on my bare skin.
“Technically I'm only supposed to give you one punishment, but I think I'm going to do two small things instead. You see, the first part is a mental punishment, and the second part is a physical punishment. And my guess is you’re gonna be squirming by the time I’m done.” This domineering side of Christopher was new. I can’t say I didn’t like it, I’m pretty sure I’ll be dripping on his leg soon which is pretty hard evidence I actually enjoy it. But at the same time, I was starting to get curious how much of this was him and how much of it was from Kayla. He didn't seem like an extremely natural dominant, but to be fair, I have basically zero experience with this aside from playing with Megan recently and she has been pretty dominant so far. Regardless, his hand left my ass and I felt him pull my head up by my hair. I was staring at his phone while he was navigating to his contact list.
“Kayla and I talked about it, and we don’t think you’ll be able to stop yourself from trying to read our messages or look at pictures and stuff, so we came up with a fun response. Every time you invade our privacy, I’m going to adjust different things on my phone to make it look like Kayla is more and more my real girlfriend. Since this was your first offense, we will start off fairly small.”
I watched as he removed the little heart emoji from my contact name and added a blue one to Kayla’s, whispering in my ear that blue was her favorite color (my pussy twinged that he knew facts like that about her already), and then he changed her name to “Kay”. He only did one more thing, unpinning our conversation from his text messages and pinning her's instead. Now hers would always be at the top and mine wouldn’t.
Let’s be real, that was basically nothing. Looking back on it, I remember thinking, “that’s the punishment?” But believe me, it also drove me crazy as time went on. You’ve made it this far in my story already, so I’m sure you can tell that that won’t be the last time I invade their privacy.
“Now, I know you probably think I need to work on my punishments," (wow, it's like he can read my mind or something) "but I think an easy start is good for you. Plus, I can see how wet you are, and I think the idea that every time Kay texts me I’ll see the little heart will really make you wonder if I’m falling in love with her. You’ll wonder if our texts are really full of love or if we are just teasing you. You’ll start wondering if I prefer her pussy to this soaking wet pussy.”
He shoved two fingers quickly into me, making me gasp in pleasure. He pumped them in and out a few times, before pulling them out before I could really get going.
“I’m also punishing you in a more crude way because I'm curious if being more dominant is something we'll be into, but I still think you’ll love this.” And before I could respond in any way, he let go of my hair and smacked my ass, hard.
“Oh shit!”
He hit me three more times without pausing, and while it was painful, I couldn’t deny there was a pleasure buried in there. I mean, I’m not going to seek out physical punishment all the time, but there was still something so sexy about being dominated like this, about being treated like an inferior. Christopher noticed my pussy leaking on his leg.
“You little slut, you’re enjoying this! I knew it! Maybe I should tell Kay and she can find ways to incorporate it. What do you think about that?”
Fuck, thinking about her punishing me too was a little hot. To be clear, I don't think I'm super into this pain thing, but I do enjoy being dominated like this. So if part of that is the occasional physical pain punishment, I can be into it at least a bit. I was definitely wet for this one. He laughed at me as he hit each of my cheeks two more times. I was biting my lip now to hold in my moans. I’m not going to orgasm from this, but everything that’s happened since I picked up his phone has me so fucking horny right now!
After two final hard smacks, he slowly rubbed my ass in a comforting way. I don’t know if it was red or anything dramatic, but his hands on me felt amazing. I tried to wiggle to entice him to touch my pussy, but he just laughed at me and pulled me off of his lap.
“Oh, no, Maddy, you’re being punished. No matter how turned on you get from your punishment, I’m not going to let you orgasm right now, then you would be encouraged to break the rules more. Nope, I want to leave you a little horny girl. Now come on, it’s time to get dressed, I gotta get back to work. You can masturbate later if you want, I won't stop you from doing that...yet.” He smiled at me as we stood up again.
We talked while getting dressed, normal life stuff, but I was still shocked he left me this horny without shoving his beautiful cock in me. I was tempted to push back and just take it, but I knew I needed to get back to work too.
I wasn’t able to concentrate at all the rest of the day. I was honestly tempted to sneak to the bathroom to relieve the pressure, but I felt like I should just wait for home. I didn't last long after walking in though, I pretty much dashed straight for my room and pulled out the new pair of blue lingerie and masturbated through two orgasms. Fuck, the orgasms I've had since diving into this cuckquean thing have been excellent. I hope they continue to be this good.
The next two days went the same way: difficult to concentrate, constantly watching Kayla as she typed away on her phone clearly talking to Christopher, messaging him myself and wondering if the delays before he responded were because he was talking to her, and of course spending another 30 minutes each day with my head between Megan's thighs. The past two were in the evenings, as it seemed she didn't want to be rushed and enjoyed making me take my time and calling me her good little puppy each time I finished her off.
Friday was the longest day of work ever after Kayla told me she wanted to talk to me before she left for her date with Christopher. She hadn't talked to me about the Wednesday stuff at all yet, so I figured that was going to be the topic of conversation, but I had no idea what she was going to say. I literally couldn't think about anything else at all that day. I ended up leaving an hour early, just eager to be home and talk to Kayla.
She wasn’t home when I arrived. I could hear someone in the shower, but I wasn’t sure if it was Britney or Megan. Other than whoever it was, I was by myself at the apartment. I waited patiently in the living room for Kayla to get home. The shower finally turned off, but I didn’t get up to see who it was when she walked back to her room. About an hour later, Kayla finally arrived. As soon as she walked in, she saw me sitting there and smirked at me. She beckoned me to follow her with her finger and turned to walk to her room. I got up and scurried after her, unable to control myself at this point.
Once we were in her room, she pointed down to the ground, clearly indicating I was to kneel down without having to say a single word. I did just that and watched as she moved about.
“So, little Maddy couldn’t help herself and invaded our privacy…I can’t say I’m surprised. We both know how much you want to witness me stealing your boyfriend right from under your nose.”
She smiled at me from her bathroom as she took her hair down. It looked like she was prepping for her date. She was quiet for a minute after that, straightening her hair just inside the doorway to her bathroom. After a bit she spoke up again.
“Chris, told me you enjoyed your punishment, and even enjoyed the part he added in. I’m glad to hear it.” She smirked at me again. How was she so good at that?! And of course he told her, they were enjoying me spiraling out of control.
“I didn't say it in the message, but there is an additional part to my part of your punishment too. I know you thought me fucking Chris was going to be the punishment, but nope, there is more. Though I'm pretty confident that you'll love my addition even more than his.” She was enjoying drawing this out. Thankfully her carpet was soft, otherwise my knees would probably be hurting by now.
“As you obviously know, I’m going to fuck our boyfriend tonight. Don’t worry, I’ll send him back to you afterwards, but not until he’s fucked me good and hard.”
I couldn’t help but picture it as she spoke. She was done with her hair by now, and was pulling her work dress off. She showed no signs of restraint as she revealed she wasn’t wearing a bra and that she was wearing a sexy lace panty today. She was flashing me and showing no embarrassment. I wish I was that confident with my body…
“And I know how much you are looking forward to it. Don’t deny it, the thought of his dick inside me gets you so wet, doesn’t it?”
“Yes.” My voice was soft, much more submissive than I intended it to be. She picked out a sexy little black dress and laid it out on her bed. She then turned to me.
“So, this one time, I’m going to give you a great treat. But only this one time will you have permission to do it. I will text you before we get home, and if you want you can sneak in my room and hide in the closet. Leave the door cracked and you can watch me fuck our boyfriend for the first time. I’ll even make sure you have a good view. You can choose if you want to do it or not, but I think we both know you’ll be there. I’ll make sure Chris goes to the bathroom afterwards and you can sneak out without him knowing you were here. It’ll be our little secret. How does that sound?”
Fuck me, that sounded so hot. I’m not fighting it right now, I wanted to watch them so fucking bad. “That sounds amazing.”
“Awe, just like the good little cuck I knew you were.” She pulled the dress over her body, still sans bra and only with her lace panties on underneath.
“But remember, this is the only time I’m giving you permission. Also, if you do this, you must be completely naked as you hide in my closet. Don’t bring any clothes with you. You will have to sneak in and out while completely naked. You can play with your little cunt all you want while I fuck Chris, but you will be naked the entire time.”
She leaned back on a cabinet in her room and watched me. She knew how sexy she looked, and she knew I would be there, naked, in her closet when she got home tonight.
“Now, one last part of your punishment is this: if you want me to fuck our boyfriend finally, you need to crawl over here, pull my panties off, kiss my pussy, and ask me to fuck him. Make sure you ask nicely, or I might say no.”
We both knew I would do it. There was almost no hesitation in my body as I bent forward so I was on all fours. I crawled over to Kayla as she spread her legs for me. I stared up her dress, seeing her leer down at me. I reached up and pulled her panties down, noticing her perfectly trimmed hair. I pulled them off her feet, and looked back at the pussy my boyfriend would be fucking tonight. I’m at least used to having my head between a woman’s legs thanks to Megan so I didn’t pause before leaning forward and kissing Kayla‘s clit. Officially the second pussy I've kissed in my life.
“Please fuck our boyfriend tonight. He will love this beautiful pussy and I know you will love his dick too. Please have sex with him.”
“Hmm, that’s much better begging than I honestly expected. It can still be better, but I will happily accept that for your first attempt. Now, if you choose to watch tonight, before you can leave my room, you have to kiss my pussy again and say thank you for fucking our boyfriend. Am I understood?”
“Yes, I won’t forget.”
“Good! You can keep those panties for now, I know you love the little collection of my underwear you keep in your bedside table. Now, I already told you part of the last part of your punishment, but I want to elaborate and make it clear.”
Of course there was more.
“So, let's call this rule number 3: I will go on at least two evening dates with Chris every week. And while I am on any date with Chris I expect you not to text him at all. If you do, there will be consequences. I want his attention on me while we are out, not on you. Tell me you understand.”
“Yes, I understand. I won't message Christopher when he is out with you.”
“Good girl! I knew you would be such a perfect little cuck quean! Now, give your cake a kiss and get out of here, Chris will be here soon.”
I stood and gave Kayla a kiss, surprisingly she shoved her tongue in my mouth. I think she’s just laying her claim as superior to me, but it was unexpected and fucking hot. I left her room and changed into something comfortable for the evening, adding Kayla’s panties to the collection drawer (the one she clearly enjoys that I have). I waited in the living room, where both Megan and Britney were watching some baking show. I barely paid attention as I waited for Christopher to show up.
Eventually he knocked and I got up to open the door. I went to kiss him once the door was opened, but he stopped at a quick peck, winked at me, and said he was here for Kayla. She came out of her room, looking sexy in the black dress from earlier. They kissed right in front of me, long and exaggerated. When they finally pulled apart, she turned and said bye to all of us, winking at me when we made eye contact (Ok, the winking is starting to feel conspiratorial or something). I stood there with my arms folded across my chest as she left with my boyfriend.
This night was going to drag on. I needed to find some way to distract myself, even though I knew that was impossible. Surely there wasn't anything that could get my mind off of my cuckcake fucking my boyfriend tonight while I watch from the closet. Fuck, I think I'll officially become a cuckquean tonight. Right? Watching your boyfriend fuck another woman makes it official, right?
A/N: wow! I can’t believe we’ve made it to 50 chapters already! Thanks everyone who has made it this far! If you’re enjoying the story so far, let me know by hitting the like button, leaving a comment, or sending me a message! All of those are huge encouragements for me to keep going. I have some huge plans for our little cuckquean, including things like more voyeurism, submission, pet play with the roommates, a vacation with the 5 of them, some sneaky/hidden sex stuff, and more! If you have any ideas or requests for our little quean for adventures or punishments, please let me know. I’ll gladly see how I can adapt the story to fit as much as I can. Hope we can make it another 50 chapters! -ASW
How should I distract myself while they are gone?
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Cuckqueaned By Friends
Friends take advantage of a weak-willed girlfriend
Her friends take over her relationship in ways she didn't expect.
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Updated on Feb 8, 2024
by Anonstorywriter
Created on Jan 16, 2022
by Anonstorywriter
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