My Tall Mistresses Pt. 03

This is a fictional story with fictional adult characters and an intense level of humiliation. Comments and suggestions for future chapters are welcome.

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I slept all night. I didn't hear when they came to sleep, nor when they woke up before me in the morning. I was woken up by Michelle gently patting my butt and saying, "Good morning Timmy, it's time to wake up!"

I quickly get dressed and go to run the coffee machine. I served two coffees to Sandra and Michelle who were waiting for it. Michelle drinks it quickly, then she leaves for work, not after kissing my cheek and saying, "Have a nice day, see you in the evening! Behave at home!"

On the other hand, Sandra takes more time to get ready as her training doesn't start before one hour. She makes sure to instruct me properly on how to clean the bathroom, then she finally leaves.

Once I am alone at home, I start cleaning the whole apartment, making sure to do a great job. I am a hard worker, and in about three hours I am done already. With all the time I have left, I think I could go out for a walk, but I don't have any other clothes than the embarrassing kids' T-shirts and pants that Sandra bought me. So I decided to stay home and watch TV.

I got the time to make some considerations about Sandra and Michelle. I like Michelle and her perfect body. Also, I love her caring manners, when she is not angry. On the other hand, Sandra intrigues me for her manipulating personality and her wicked way of treating me. I have the feeling that she takes pleasure in humiliating me.

Not long after, Sandra comes back home from her training. I get the impression that she has been working out a lot. First thing, she controls all over the apartment that I have been cleaning properly, but luckily the job I have done doesn't disappoint her.

"You did a good job," she says, "I am going to take a shower now. Come to the bathroom so that we can talk while I am at it."

Intrigued, I follow her to the shower. All I can think is that I will see her naked. She removes her sports clothes while I am there in the room, staring at her. While I enjoy watching the show, I can distinguish two separate feelings. First, I am confused about why she wants me to watch her taking her clothes off. Second, I feel a strong sense of inferiority by seeing how long and tonic her legs are compared to mine.

Before removing the bra and panties, she walks close to me. All I can do is notice that her buttocks reach my chest. I am all hypnotized by her stunning body. She orders, "Hey... Turn around, it's not time now to see anything more." But she doesn't give me time to do so because she just grabs my shoulders and turns my body by 180 degrees.

She enters into the shower cabinet that is non-transparent, then she communicates to me, "I am in, you can turn back again," and I do so. Then I finally got to know what she wanted to talk about.

"You know... The previous two tiny men that Michelle brought home left as soon as I told them they would never get to penetrate her. That was all they cared about. So, I was wondering, why are you still here? Why don't you just leave if you know you cannot penetrate Michelle?" Sandra asks.

I take 5 seconds to think of a clever reply. I say, "I like Michelle, she is one of the most beautiful women I ever met. I want to be honest with you Sandra: if one day she will ask me to have sex with her, and I mean to penetrate her, I will do it. But if she doesn't ask me, I respect your rule and I will never propose or ask her to do so. On the other hand, I would be glad to have any other sexual activity with her."

I think she is intrigued by my reply, and indeed she says, "Any other sexual activity? Good. That's more or less what I was hoping for. And about you penetrating her, I don't worry much about it, with your tiny penis you wouldn't be able to do so."

I don't agree with what she says, but I don't reply. She continues,

"I have one more question for you. If you end up doing any sexual activity with Michelle, would you mind me joining you?"

I reply promptly, "Of course not."

"Good, looking forward to having some fun then!" Sandra says happily. However, her tone, leaves me with a weird feeling, as if she is playing some sort of game with me. Also, all this talking drives my mind, and my dick gets hard. I regret I didn't masturbate myself when I was alone at home, now that I am all horny, I don't care about the main rule of the apartment anymore, and I really feel like masturbating.

After she is done from the shower, I pass her a towel and she goes to the bedroom to get dressed. I seize the opportunity and decide that it's my turn to take a shower. As soon as I am in the cabinet, I start touching myself. With all the accumulated arousal, I reach the climax in a few seconds and I am just enjoying the long-awaited moment.

Naturally, I lift my head to the ceiling and I see her. I thought I was safe in the shower cabinet but I was wrong. Sandra is tall enough to stick her head in from the top of the cabinet, and she is looking at me. I see her eyes, and I see a phone too, with the back camera pointing down to me.

I am paralyzed in panic. Michelle told me about this rule since the beginning and I already failed to respect it. I thought to apologize to Sandra and beg her to not tell Michelle, but she doesn't give me time to do so. She leaves the room saying with a happy tone, "I am going out now, I need to buy something, I will be back." Before leaving the apartment, she adds with a more aggressive tone "Make sure you clean the shower again," then I hear the door closing.

I get out of the shower. I sense it will not be an easy evening for me, given what I did. I get dressed and I obey by cleaning again the shower. I feel a huge sense of guilt and I am ready to apologize to both Michelle and Sandra. I try to think about what to say and plan a speech to help my situation.

One hour later, Michelle comes back from work. She looks tired but very happy to see me. The first thing she does is to put her hands under my armpits and lift me up. Then, she puts one hand under my buttocks and gives me a deep kiss that, as the day before, completely hypnotizes me. After her kiss, I feel so light that I try to mumble something but I cannot say anything. She carries me to the sofa and, like the first day, she gives me takes out one boob from her neckline, and I start sucking.

I am thinking of confessing that I broke the rule, but I see her so happy that I don't dare to ruin that moment. While we are on the sofa, alternating kisses to boob-sucking, Sandra comes back home.

Michelle greets her from the sofa, but she doesn't reply. She walks straight to us and says to me, "You haven't told her. So, I will," then she looks at Michelle and announces, "He came in the shower, in our shower. This pervert masturbated and jerked off in our shower."

I am petrified. Michelle looks at me and asks, "Is it true what is she saying?"

At that moment I am still lying down on her legs, completely vulnerable. I try to reply but Sandra doesn't give me time to do so. She takes her phone out and plays the recording of me in the shower in front of us.

Michelle, with an energic move, pushes me away from her and the sofa. Then, she looks at Sandra and says, "We cannot trust Timmy. I am sorry Sandra, I am going to kick him out of this apartment now."

Sandra, however, reacts as if she was already prepared for this, and says, "No Michelle. I agree that we cannot trust him, but we don't need to kick him out."

Michelle stays silent and listens.

"I went to our favorite sexy shop and bought this one." Sandra takes out from a bag she had in her hand a small pink object. At that moment, I don't understand what it is, but Michelle has the look of someone who does. Sandra continues,

"I was worried I wouldn't be able to find one small enough for his size, but luckily, they had one exceptionally small. Of course, he still needs to be punished."

With an impressive synchronization, they grab me from the ground and remove my clothes in a split second. I am not in a position to fight, so I let them do it. At that moment, I still didn't understand what is the device that Sandra bought.

I am there standing naked with them around me when Sandra asks, "Are you proud of what you did in the shower?"

"No... " I reply softly.

"Are you ready to pay the consequences of your actions? Or do you want to leave right now?" Sandra asks while Michelle is listening with her hands on her hips and an angry face.

I don't want to leave, also I am all naked and I couldn't go out like that. I reply, "I am deeply sorry for what I did. Tomorrow I will work double the time to pay you back."

Sandra laughs at my reply. She says with a stricter tone, "Don't let me repeat myself again. Are you ready to pay the consequences of your actions? Make sure you reply honestly, there is no going back."

"Yes," I reply looking down to the floor.

I see the arms of Michelle appearing between my legs, then she lifts me. She holds me with her arms under my knees, with my legs spread open and my penis in the air. Sandra is in front of me, and says, "This is a chastity device. You will wear it all the time. It will stop your erections so that we are sure you cannot masturbate. It comes with a hole so that you can still pee while wearing it. However, hygiene is very important, so every few days, you will get to remove it to clean it and clean yourself."

I start to panic, I try to free myself from Michelle's grappling but I don't manage. With my hands, I cover my penis. Sandra looks at me and orders, "Remove your hands from that tiny shrimp."

I don't obey, but Michelle, with her hands who are free, grabs my wrists and spreads again her arms, spreading both my arms and legs. My humiliation when Sandra locks my penis is huge. I think about the fact Michelle is holding me in that position, and about Sandra that is looking at me with a satisfied smile on her face. I see the key that just locked the device going into Sandra's pocket.

Michelle finally puts me down and says, "Now, you are allowed to touch yourself as much as you want."

"I hope it's thigh enough, otherwise I really don't know what to buy," adds Sandra entertained.

I take my panties and put them on. I am about to take my pants too when I feel a force pulling me back and preventing me from walking. It's Michelle. With one hand, she grabbed my panties and pulled me towards the sofa. I fall on her legs, this time not on my back but on my stomach. With one leg, she secures my legs on one side, and with the other hand, she pushes my chest down to the other side. My ass is all vulnerable in the air.

Michelle pulls the back of my panties like a tanga in between my buttocks. Then, I felt the first spank. Then the second, and so on. I am good at holding any reaction, but after the 20th, I start making sounds, then I start screaming.

"Good... good..." says Sandra, "Leave him to me before you make him cry. It's my turn."

Michelle easily lifts me and put me on top of Sandra who in the meantime sat on the sofa. Then, she starts spanking me too.

Her spanks hurt way more, both because she is probably hitting harder, and because my skin is already all red and hurt. What is worse, while spanking, Sandra humiliates me with her talking.

"Look at this one. Just yesterday he was saying to me that he was a man and that he could not accept being treated like a baby by someone younger than him. And now look at him: wearing a chastity device and getting spanked and punished by two young girls."

Despite the pain, the humiliation causes me an erection, but the cage I am wearing blocks it. At some point, the pain in my ass is too much and some tears come out from my eyes while I yell, "Stop please, it hurts too much".

Sandra stops, she releases her hold on me and I quickly run to the bedroom, to the bed. I hear Michelle's steps but Sandra says, "Leave him for now. He needs time to digest all this."

I want to cry, I had the feeling that things were going well this morning, but I was wrong. I take courage and go back to the living room. I tell them, "Give me the key now. I am going to show you what I can do. Give me the key now." I still have tears in my eyes, but I speak with a firm tone.

Michelle just ignores me. Sandra laughs, "Ahahaha and what can you do? With that tiny shrimp? I told you, there is no coming back from this. Better you get used to it."

I am petrified. She continues, "Look, your body will just adapt to it, don't worry. You will see soon that you will not feel like masturbating anymore. And we don't have to worry about it anymore too. So, why remove it?"

"But I..." I try to say but Michelle interrupts me, "I had enough of you. Go back to the bedroom or I'll spank you more."

Sandra agrees, "Go back to your room Timmy, think about what you did and about your new situation. Ah... As owners of the key that unlocks your tiny penis, from now on, you must refer to us as your MISTRESSES."

I ran back to the bedroom. I lay desperate on the bed until I fell asleep.

I wake up due to some noise I hear in the room. It's Sandra and Michelle. They are on the big bed. Michelle is lying down on her back, with her legs spread open in the air. Sandra is on her knees in the middle of Michelle's legs. She is completely naked except for a belt I see that goes around her hips. I clear my sleepy eyes and I try to look better. Sandra is wearing a strapon and she is fucking Michelle that, at the same time, is moaning loudly, and that's what woke me up.

I am paralyzed. It was like they didn't care that I was sleeping there. Or maybe, they wanted me to look at them. I am intimidated by these huge bodies moving and sweating, 'Would I ever be able to hold on to their rhythms?' I ask myself.

Sandra has a statuesque body, proportionate forms, and long straight black hairs that undulate as she moves. On the other hand, Michelle's curves bounce with rhythm. I get horny in a split second. My dick trembles to be freed and cannot grow inside the cage. I try to touch it but it's pointless as the plastic of the device completely covers it.

I am looking at them hopelessly when, while they change position, I encounter the sight of Sandra. She looks at me for a second, then informs Michelle, "Timmy-tiny-dick woke up."

"Poor baby, we have been a little bit mean with our punishment before," says Michelle turning her face towards me, with a completely different tone compared to the last time she talked to me.

"You are staring at us, Timmy, it's not nice." Sandra points out.

I take my gaze away and say, "I'm sorry Sandra."

"Maybe you wanted to say, 'I'm sorry MISTRESS', ...," remarks Sandra.

"I will not call you like that," I say firmly. I am all horny but I cannot withstand the humiliation anymore.

"Why not? Are you still convinced that you are a man? Do you think that you are at our level?" asks Sandra. Michelle is looking at me. Her face betrays a feeling of pity towards me.

"Sandra, you are being too harsh on him," Michelle takes my side, for one time. But this does not make things better for me. Indeed, Sandra is always full of ideas to further humiliate me.

"All right, all right. I admit I am being too mean to him. But, Timmy, you are so small... It comes naturally to treat you like a hopeless baby. Anyway, I think we should give you a chance to prove us wrong. I am going to unlock your tiny shrimp now and you can do whatever you want with us. Whatever you manage to do."

I was waiting for a chance like this one. "Can I have sex with Michelle?" I ask Sandra promptly, Michelle looks entertained.

"Well well... you know I don't like what you asked. But given your situation, I will allow you to try at two conditions."

"What conditions?" I wonder.

"First, if you fail in doing your job, I will lock you again and you will have to call both of us Mistress."

"Ok that I can do," I reply, thinking that, anyway, I am already locked up.

"Second, if you fail in doing your job, you will have sex with me."

I am confused by this second condition. What does that mean? I think about our small talk in the bathroom, maybe she really wants to have sex with me? Is there a quibble in this deal? She gives me no time to think. "What is your decision? Do you want to stay in bed looking at us? Or do you want to try your best with Michelle?"

I reply, "OK, get this cage off of me."

I see Sandra is not pleased by the way I order her to free me, but she doesn't react. She gets the key from the pocket of her pants on the floor, then she unlocks my penis.

As soon as my dick is free, I remove my panties and it starts to get hard. In the meantime, Michelle gets on her knee in a dog-style position. Her huge vagina is right in front of me. She turns her head and says with a smile, "Whenever you want, Timmy."

Quickly, I realize I have to stand on the bed if I want to reach her, so I do so. The more I look at our differences in size, her leg against my leg, her big black butt against my small waistline, the harder my dick gets. Sandra is looking at us with a huge smile on her face, but I don't pay attention to her. I grab my dick and I try to penetrate Michelle.

A cold shiver runs down my back when I realize two things. First, despite my blows, Michelle's body does not move an inch: she stays still as if I am doing nothing. Also, differently from when she was getting fucked by Sandra, she doesn't make a single sound. Second, my dick penetrates between her buttocks, but it is not long enough to reach her huge vagina.

My embarrassment is huge, but I try to continue. Michelle does not make a single sound. I see Sandra getting close laughing, she looks toward my dick and says,

"I told you, Timmy, you did not believe me. Again, you only need some evidence to believe it yourself. I hope you will start trusting me more."

I am confused, I stop blowing on Michelle's butt, and she sits on the bed.

"You tiny shrimp is not long enough to reach Michelle's big vagina. And, even if you could reach it, she would not feel you because it's too tiny," says Sandra with a teaching tone. Then she takes a breath, and continues,

"I knew this would happen since the first time I saw your dicklet. If you had trusted me, you would have avoided this shameful situation. Did you think I was joking? You cannot physically penetrate Michelle."

"Wait... She didn't open her legs properly... We can try another position..." I try to say but Michelle interrupts me, "No Timmy. You had your chance and you failed."

"Another position? This time Timmy you must trust me: it will not work. You are genetically unable to fuck Michelle." concludes Sandra.

My dick gets small and floppy because of all the humiliation. With her usual wicked smile, Sandra locks it again, and this time I offer no resistance.

"Now, your Mistress Sandra is going to have sex with you," says Sandra, "Come here little Timmy!"

I don't move, I am confused. How can we have sex after she locked me up and, especially, after it was clear to everybody that I cannot penetrate big women?

Sandra picks me up from my armpits and throws me to the middle of the bed. I fall on the back. She grabs my heels and pushes them so that my knees are close to my head and my butt is all exposed in the air. Then, Michelle grabs my heels and holds me firmly, making sure I cannot move from that position.

"I feel sorry for you and the humiliation that you are experiencing Timmy, and I want to be nice to you. I will use a lot of lube so that it will not hurt," says Sandra.

I start to understand her intentions, she wants to fuck me with her strapon. I cannot allow this. I remind myself that she is just a young girl and I am an adult man. "This will not happen," I say to them and myself.