Simon and Aunt Sophia Ch. 04

Note: (This is a continuation of number 3 and really does not work as a standalone.)

Simon gave the two sister's the entire day to talk. He thought it would be easier for them if he wasn't there. They texted they were expecting him back for dinner.

He walked into the apartment and saw Sophia and his mom standing by the door in nothing but their underwear and high heels.

Simon: What is this?

Sophia: I couldn't talk her out of it.

Simon: Talk her out of what?

Sophia: Two sluts if you will have us.

Simon couldn't believe it, after everything she witnessed last night.

Simon: Does she really understand what she is asking?

Sophia: I explained it to her in great detail. She asked a lot of questions.

Simon: Is this really what you want, mom?

Claire: Yes.

Simon: You didn't call me sir?

Claire: Because you have not agreed, so it is not my place to.

Simon: And why are you both in your underwear?

Claire: We thought you might need some inducement.

Simon had to admit she did look sexy. Big voluptuous breasts and an ass he would not object to paddling.

Simon turned to Sophia.

Simon: Is she serious?

Sophia: I would say very determined.

Determined, Simon thought, we will see about that.

Simon: I will agree to this on one condition from both of you or we can just go have a pleasant dinner. If we do this tonight then I will not be escorting two sluts but rather two whores!

Sophia's head shot up. She knew the implications of that.

Claire: I don't know what that means.

Simon: Explain it to her, Sophia.

Sophia: It means he can tell us to have sex with anyone he chooses.

Claire's whole body tightened up. She didn't expect anything like this. Maybe he was just trying to scare her off but she wasn't sure she could find the nerve to go through with that.

Sophia: Yes, sir

Claire: You are agreeing to this?

Sophia: Claire, it is all comes down to trust and I trust him.

Claire: And you can decide to make me have sex with any man?

Simon: Not just any man, anyone, including each other, I should point out.

Claire and Sophia looked at each other.

Sophia: Yes, sir

Claire: I don't know

Simon: Great, get dressed and let's go have dinner.

Claire: Wait! Yes, sir

Simon: Okay, Whore, let's see if you even make it out of this apartment. Pull your panties down to your knees.

Claire was shaking but did as she was told.

Simon: Do you understand the rules about answering questions, whore.

Claire: Yes, sir. I am to answer all questions completely and with absolute truth.

Simon: Good. Last night I noticed you fidgeting in your chair, why?

Claire groaned. He wasn't going to make this easy, why would she expect otherwise, she thought. She remembered his comment before leaving this morning. He noticed.

Claire: Because my vagina felt uncomfortable, sir.

Simon: Whore's don't use the word vagina. Try again.

Claire: Because my.....pussy felt uncomfortable, sir.

Simon: What do you mean by uncomfortable?

Claire: It was getting excited, Sir.

Simon: Do you mean it was getting wet?

Claire: Yes, sir.

Simon: Then say it, whore.

Claire: My pussy was wet, sir.

Simon: Are you wet right now?

Claire: Yes, sir

Simon turned to Sophia.

Simon: I will still call you slut tonight otherwise there may be confusion.

Sophia: Yes, sir.

Simon: Go check and see if the whore is wet, slut.

Sophia walked to Claire and stuck her finger in her pussy. Claire gasped.

Sophia: She is, sir.

Simon: Rub her pussy for her, slut, let's see how long before she cums. Look at me, whore, while the slut plays with your cunt.

Claire looked up at Simon. That last word giving her a jolt. She had no idea why but she didn't want to think about the why's tonight. She was moaning now, maybe she was a whore, she thought.

Claire: May I cum, sir.

Simon: You may cum tonight as often as you like without asking.

Claire: Thank you, sir.

Claire came very hard and sunk to her knees. She came right in front of them from her sister's fingers at her son's direction and she loved every second of it. She couldn't remember ever cumming harder or feeling more humiliated.

Simon picked out their outfits. Sophia was chosen an elegant dress that flowed at the bottom. Claire didn't bring anything to Simon's satisfaction so he picked out one of Sophia's dresses that was two sizes to small, tight and short. Claire felt exposed and ridiculous but she still had a nice figure and had to admit she felt sexy.

Claire could feel the stares as they walked to the table. The men didn't seem to mind but the women let their sentiments known with their sneers. She couldn't blame them, a woman her age wearing a dress like this is... That's when she realized why he made her wear this dress. Not because it is sexy but for her to feel shame and shame she felt. She tried to put her eyes down but Simon wouldn't allow that of course.

Simon: Look at their faces, whore. Feel their judgement just like you tried to do to us when you discovered your sister and I.

Claire: Yes, sir.

Claire scanned the people in the room. She could feel their disgust. She looked at Simon and his cocky ass grin.

Claire: Enjoying yourself, sir?

Simon: Much more than I anticipated, actually.

Claire: I'm glad to be of service.

Simon: You have a lot more servicing to do tonight.

Claire: I am well aware, sir.

Simon: You have no idea, I assure you.

Claire saw the smile on his face and knew he had something bad planned. She had never been more scared in her life nor more excited.

Simon: Give me your panties, whore.

Claire: Can I go to the ladies room to remove them?

Simon: Don't be ridiculous.

Claire sighed, looked around and her slid hands under her dress and wiggled them down as nonchalantly as she could manage. She went to hand them to Simon under the table but Simon put his hand out above the table. She signed and put them in his hand.

Simon noticed how wet they were and smiled at her and brought them to his nose. He handed them to Sophia indicating for her to do the same.

Surprisingly, Claire felt pride in her wet panties and more determined now. She knew he was trying to break her spirit and she could see how much he was enjoying her discomfort. A part of her wanted to please him and another wanted to kick him in the balls but to her absolute astonishment she thought both emotions were exciting.

Simon watched as his mom strutted out of the restaurant like she was a model walking down the runway. He was impressed with her and how the night was going. Let's see how she handles round two, he thought and smiled.

When they returned to the apartment Simon's childhood friend Jeff, that now lived in the area, was waiting for them.

Simon: Hey, glad you could make it on such short notice. You've met both these lovely ladies before. They exchanged pleasantries and headed to the apartment. Once inside Simon addressed the women.

Simon: Whores, you are being very rude. I am sure our guest has been wondering what you are both wearing under your dresses tonight. Have you not, Jeff?

Jeff: Well, that would be nice.

Simon: You see, whores, take off those dresses.

Sophia and Claire slipped out of their dresses and remained still. Simon and Jeff smiled at each other

Simon: Let me explain why my good friend Jeff is here. Before I left for college, Jeff had a summer party at his house. To make a long story short I fucked Jeff's mom's brains out.

Claire gasped, Jeff's mom was a friend of hers. Simon smiled at her.

Simon: Do you have something to say, whore?

Claire: No, sir.

Simon: Anyway, she was very enthusiastic if I recall and Jeff walked in on us. He was not as enthusiastic about the situation as his mother seemed to be and the only way I could get him to forgive me was to promise, if a situation presented itself, to help him fuck this whore here.

Claire eyes shot to Jeff who shrugged.

Jeff: It's true. I was really mad but he told me he would reciprocate if he could and well honestly I've fantasized about fucking you my whole life.

Claire was having trouble staying upright. She was flattered, Jeff was a good looking young man but she has known him since he and Simon were in elementary school for Christ sake. She knew she was in over her head, she couldn't go through with this.

Claire: Sir, I am sorry but I am not sure I can do this.

Simon turned to Jeff and shrugged.

Simon: Don't worry, Claire, you can get dressed and leave. Slut, you will be fucking Jeff tonight in Sophia's place.

Sophia: Yes, sir.

Simon couldn't help but notice how happy Sophia looked at this moment.

Claire: Wait, what?

Simon: I knew there was a chance you wouldn't go through with it so I promised Jeff the slut in your stead, who he has also been dying to fuck since the day I introduced them.

Claire: I can't let her do that!

Simon: It doesn't looks like she minds, Claire. Do you mind, slut?

Sophia': No, sir.

Claire: Wait, hold on. You brought him here for me and if I refuse Sophia will be forced to take my place?

Simon: Yes, Claire.

Claire: I will do it, sir.

Simon: I'm not sure, Claire. I promised him Claire the whore tonight. If you are not one hundred percent that whore tonight then I will still be forced to give him the slut to make up for your lack of commitment.

Claire: I understand, sir.

Simon: Are you sure?

Claire: One hundred percent sure, sir.

Simon: Well, I still feel badly for my friend for your hesitation.

Simon turned to Jeff.

Simon: What if they both sucked your cock and balls together before you fuck the whore, my friend. Does that sound fair?

Jeff smiled and looked Sophia up and down.

Jeff: I think so.

Simon gave Sophia a wink. He knew she has been ready and willing for something like this for awhile now. Sophia gave him a very reassuring smile.

Simon: Wonderful. Whore's why don't you get us something to drink.

Sophia and Claire: Yes, sir.

They walked away slowly and seductively as expected of them. They returned with wine and filled the glasses for the two men

Simon: Jeff, would you like to finish undressing one of them?

Jeff: Sure!

Simon: Great. Stand still, whore's so Jeff can undress one of you. Jeff, whore's love to be fondled so if you see some area you would like to explore. I am sure they will appreciate it. Isn't that right, Whores?

Sophia and Claire: Yes, sir.

Jeff made a beeline for Simon's mom, Sophia is obviously the younger and more beautiful but Jeff had fantasized about Claire so many times he just couldn't wait to get his hands on her.

He got behind her and unclipped her bra and pushed it down from the front getting a big double handful of her large breasts, squeezing. Claire gave him an approving moan.

Simon: I told you how much they like being touched, buddy. Do it for as long as you like. Jeff spent a little more time fondling her breasts while telling her how hot he thought she was and how often he thought about doing this to her.

Claire was getting so turned on listening to Jeff and was enjoying his touch immensely.

He moved in front of her and pulled her panties down. He wanted to be eye level with her pussy. He has day dreamed of seeing it so many times he couldn't believe it was right in front of him.

Simon: Would you like to smell it, Jeff?

Jeff: Sure.

Simon: Whore, ask Jeff to smell your dirty slut cunt.

Claire's mouth was suddenly very dry and she tried to swallow and the thought of saying that was completely humiliating.

Simon: Slut, we may need you to take the whore's place.

Sophia: Yes, sir

Claire: Wait! I can do it.

Claire took a deep breath to steady her nerves.

Claire: Please smell my dirty slut cunt, Jeff.

Jeff stuck his nose right up against Claire's clit and inhaled deeply. Claire felt shockwaves throughout her body.

Simon: Would you like to taste it, Jeff?

Jeff: If she wants me to.

Simon: Whore, do you want Jeff to taste your dirty slut cunt?

Claire wanted it really bad but she still didn't like asking for it like he was making her.

Claire: Yes, please.

Simon: Then ask him properly.

Claire: Please, Jeff.

Simon: Please what?

Claire sighed. There was only one way this night was going to go

Claire: Please eat my dirty slut cunt, Jeff?

Jeff plunged right into Simon's mom's pussy with vigor. Simon walked over to Sophia who looked very neglected at this point and told her to go get him a paddle and then to rub Claire's very erect nipples. Claire started squirming like a bitch in heat, her body quivering. Simon walked up behind her and whispered in her ear.

Simon: You dirty fucking whore, everyone is watching you love having Jeff eat your slutty cunt. Look at your body reacting to his tongue in your cunt. You are a disgusting dirty slut cock loving whore. Tell me what you are, cunt.

Claire was trying to repeat his words but she couldn't remember what to say, her body and mind were exploding together. She felt shockwave after shockwave throughout her body. Jeff started sucking Claire's clit very hard and Simon began paddling her ass. Sophia had to help hold her up as Claire lost all control from the intensity and started cumming and screaming and then squirted her juices into Jeff's eager face. They let her sink onto the floor.

Simon: Slut, why don't you suck Jeff's cock while the whore recovers herself.

Sophia: Yes, sir

Sophia got on her knees and pulled Jeff's cock out and began sucking him off.

Claire eventually was able to sit up.

Simon: Are you done now, whore. Does the slut have to fuck Jeff for you?

Claire was humiliated, exhausted and probably a thousand other emotions at that point and she knew he was trying to make her quit but she was still determined.

Claire: No, sir!

Simon: Well then go help the slut suck Jeff's cock and let him fuck your squirting slut cunt anyway way he chooses for however long he can hold his cum.

Everytime Claire thought this couldn't get any more humiliating Simon found a way to make it so. She knew she squirted in Jeff's face. If she had any hope of finishing this with any dignity she knew it was lost. She really was nothing but a whore now.

Claire: Yes, sir.

Claire gave her son a hateful look and crawled to where Jeff and Sophia were and began sucking his balls while Sophia worked on his shaft. After a few minutes they switched.

Simon: Make sure to look up, whore, while you suck off our guest.

Claire looked up to see the intensity of Jeff's pleasure and his look of satisfaction.

Simon: Jeff whenever you are ready, go ahead and fuck that whore's brains out. That is what you want right, whore?

Claire mumbled her assent and kept sucking.

Jeff decided he wanted her to ride him on the couch so he could play with her glorious breasts.

Simon had Sophia sit on his lap in a chair facing them and played with her pussy. He would make it up to her later in their own bed but for now he just wanted to watch the complete degradation of his own mother. He thought about that for a moment. It was a hard truth that he was enjoying it so much.

Sophia was getting too tired to continue so Jeff had her lay on the floor. He got on top of her. Her pussy was still soaking wet. He just kept pounding and she kept moaning and cumming.

Simon: Jeff why don't you cum in the whore's face? Would you like that, whore?

Claire: Very much, sir.

Simon: Ask him.

Claire: Please, Jeff, cum in my face. Please!

Jeff pulled his cock out of her sopping pussy and positioned himself over Claire's face. His cum started spewing out and Claire stuck out her tongue to try to get some in her mouth. She wanted to know what he tasted like. She had never done anything like that before but it seemed only natural at this point. What had she become, she thought?

Simon suggested Jeff leave her there and get cleaned up. The three of them were talking and laughing about the events of the night while Claire wasn't sure yet if she could move.

Simon: I hope you are not disappointed, Sophia. I decided to make tonight about Claire. I'll make it up to you when we go to bed.

Sophia: Well I have to admit to being majorly jealous of my sister over there.

Simon: Did you hear that, Jeff, we will have to plan something special for Sophia for another time. Maybe just the three of us.

Sophia and Jeff lit up at that thought.

Sophia: You better not be teasing me, mister.

Simon: No tease but I'll probably make you beg for it.

Why don't you help Claire get cleaned up so she can join us.

Sophia: Okay, Let me hurry so I can start the begging right away.

Claire and Sophia rejoined them. Simon regarded her. She seemed to be okay but he was a little worried about her.

Simon: Are you okay, mom?

Claire: Never better. Why do you ask, son?

Simon: Well you didn't lose your sense of humor anyway. Seriously, I didn't plan on being so hard on you. I'm honestly not sure why I did.

Claire: I'm the one that wanted to know what it was like so badly. Be careful what you wish for, I guess.

At that moment there were two questions on Claire's mind, could she ever go back to normal and would Simon ever fuck her with that massive cock of his? The answers were obvious, no way and please yes!