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Chapter 76 by lew54321 lew54321

Who do you make her roleplay as?

All eyes on Sis

“Considering how you were so interested in Sarah when you did your questions just now, let’s have you take on her as a role” you declared, getting only an uneasy reaction from Mom.

“How would I act like her, do you want me to call you ‘brother’ or something like that” she asked, still not sure what you were getting at.

“Oh no it's much more simple than that. You know that Sarah and I have our deal right? All I want you to do is act out what it would usually look like, at least at the start anyway.” you explained, getting a nod from Mom before she realised what that would entail.

“You want me to take off my panties right now?!” she asked with a look of shock, momentarily bringing one of her hands down to cover her mound before reconsidering and moving it back up to cover her bountiful chest. She still attempted to hide herself from your view by turning side-on, but that only let you ogle her ass that had been hidden away from you.

“Of course I want you to. Plus you have to hand them to me to keep, exactly like Sarah’s deal. Otherwise it wouldn’t be a roleplay would it?” you stated, unable to hide the grin on your face.

Mom stared at you for a while, not believing you would really make her stand naked in front of her own son. Eventually, the staring contest you had ended up in with her ended when she shied away from your gaze and she looked down at the only piece of clothing she was still wearing to protect her modesty. Although hesitant, it really showed how far she had come in the past couple of days, when she didn’t even consider disobeying you as an option.

Before she could make up her mind, you decided to throw in just one more thing to up her embarrassment.

“By the way, you should probably lock the door before we go any further. Wouldn’t want Sarah or Lucy walking in on us, would we? Maybe even dad if you got really unlucky, that would be a hard one to explain” you teased, causing Mom to blush even more before she quickly turned to the door and fastened the bolt as tightly as she could.

Maybe she found it easier to not face you but she stayed standing at the door with her back against you as she reached down towards her hips. You were disappointed that you couldn't see her now bare chest, but the view you got in return felt like it was one hundred times better. Mom hooked her thumbs into her underwear and lowered them down from her ass before slowly dropping them past her thighs and calves to her ankles. The way she bent at the waist to keep a hold of them as they neared the floor almost felt like she wanted to show off everything that had been hidden from your sight until that very moment.

Her pussy came into view between her thighs as she bent over and she did nothing to hide it from your view. You thought it couldn’t get any better until she bent all the way over to pick them up, letting you see every inch of her backside in full display. Unfortunately it didn’t last long as she stood back up straight and turned around with a blush on her face. As if now noticing her indecency, she attempted to cover herself from the front with one hand cupping her pussy while her other arm attempted to hold her chest.

Remembering the other part of the deal, she tossed her panties in your general direction and carried on standing in the centre of your room. Whether she threw them to avoid the embarrassment of directly handing them to you or if she was worried about getting closer to you, you still weren’t going to let her get away that easily.

“Good, now that you’ve given me these, I’m gonna have to do a full-body inspection to make sure you aren’t wearing anything else” you said, with both of you fully knowing it was just an excuse.

“And this is something you do with Sarah?” Mom asked in return.

“Oh no that parts over. This is just something special for you” you replied standing up from where you were sat on the bed to get closer to Mom. At first, it looked like she was going to back away but surprisingly she remained standing in the middle of the room as you got closer.

“Alright stop covering yourself with your arms. We wouldn’t want you hiding anything away now would we?” you ordered with a grin. Mom gave you a defiant look before doing as you asked and slowly raising her hands and joining them together on the back of her neck.

Taking a step back, you gave her a look up and down as if examining your prize that she was up close. With you fully clothed and her stood without a shred of clothing to wear, it amplified the feeling of power you felt you had over her. It took all your willpower not to reach out and start groping her but you managed to hold back your impulses knowing that you'd be able to fulfil your wishes shortly. After taking in the full frontal view, you left her standing there and slowly circled around her, placing your index finger against her skin and caressing her as you walked around her.

Once directly behind her, you switched from using just your finger to now using both hands to caress her back, slowly inching your way closer and closer to her ass. With the temptation becoming too strong, you cupped each of her cheeks and carried on groping before getting a firm grip and holding them apart to look at your prize that had been hidden away. Mom flinched as she realised where you were staring and couldn’t help but nervously make a comment.

“I-Is that really necessary?” she asked, with a hint of unease coming through in her voice.

“Of course it is. We can stop now if you want but that only means your next punishment will be even harsher and will come even sooner than before” you explained, getting closer to her so you could whisper into her ear, causing her to shiver when your breath hit her skin.

Mom didn’t know how to reply to that and kept quiet as you took the opportunity to bring your groin against her ass and tried to nestle yourself into her crack. With the close quarters, you took your hands away from her rear and brought them up and around to her chest. As much as you enjoyed playing with her butt, her tits were still what always drew your attention and no matter how hard you tried, you always felt yourself drawn to grope them now that you had the power to do so. You cupped and fondled them to your heart's content, hearing Mom's breathing get louder as you started to circle her nipples with a light touch.

“H-How much longer are you going to… keep going for?”Mom asked, with the words getting hitched in her throat as you started to heavily concentrate on playing with her nipples, alternating between rolling them between your fingers and circling them with your thumbs.

You avoided answering her question and carried on your **** of her more sensitive areas, slowly ramping up your aggressiveness as the time ticked by. Mom started to breathe heavier and heavier as you continued, occasionally letting out an involuntary moan or sigh that made her realise the situation she was in before succumbing to the same pleasure all over again. Her moans were getting louder and you knew that she would be getting close to cumming soon. You hadn’t even gone anywhere near her pussy but it seemed like her tits would be sensitive enough to push her over the edge if you let her.

Just as she was nearing her tipping point, you reluctantly tore your fingers away from her, hopefully leaving Mom more worked up than you were.

“Is it over?” Mom asked, with a hint of dissatisfaction in her voice that both of you picked up on before she scrambled to correct herself.

“I mean, good I’m glad you're done” she added.

“Well now that I’ve had some fun, I think you're ready for the next bit” you declared. Mom looked like she wanted to argue a point for herself but gave up as quickly as the thought appeared in her head. You had a few plans lingering in your head of what to do next but one particular option stood out the most.

What’s the punishment you have in mind?

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