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My Tall Mistresses Pt 04

My Tall Mistresses Pt 04

by anpinx
19 min read
3.18 (4800 views)
adultfiction

Be aware! 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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Given what happened, it took me time that night to fall asleep.

I was gently woken up the next morning by Sandra, "It's time to get up! This is your first day as a nonvirgin boy."

Quickly, I get up and start preparing breakfast for everybody. Both Sandra and Michelle are in a good mood.

Before leaving, Michelle asks Sandra, "Can I have Timmy's chastity key? I will be back from work early today, I can unlock him so that he can get a good shower."

"Sure," says Sandra, "but make sure he doesn't do dirty things." Then she looks at me, smiles, and leaves saying goodbye. Soon after, Michelle comes to me, lowers herself to my height, and kisses me on the cheek before leaving too.

I spend the morning cleaning the bathroom and bedroom. The apartment is small, so I get to finish early. I think that I need to get out of the apartment, even for a walk, but given that I only have kids' clothes, I really cannot. I need to find a way to get decent clothes.

Not long after lunch, Michelle comes back. She doesn't look tired. On the contrary, she looks full of energy. She tells me: "Timmy, I am going to take a shower now. Why don't you come and keep me company in the bathroom? I'd also need some help to put the cream on my legs."

"Sure," I reply.

She removes her clothes and gives them to me. As always, I get hypnotized by her stunning body. Her curves are perfectly proportioned to her height. We don't talk much while she showers, I don't just stay doing nothing but instead, I get her clothes to wash and prepare a new towel for her.

When she gets out of the shower, she drips some water to the floor. "Would you mind drying the floor for me? Then, come to the bedroom so that you can help me spread the cream on my body," she tells me with a gentle smile.

I obey. I had just cleaned the bathroom in the morning and I wanted it to stay clean and tidy. When I finally reached to the bedroom I suddenly noticed that she looked taller the normal: she's wearing heels.

"These heels will make your job easier," Michelle points out.

Besides the heels, she was wearing only a thong. "You can spread the cream on my legs and buttocks, I will do it on my arms," Michelle explains.

If when barefoot our height difference was extreme, the heels made it ridiculous: my head could barely reach her belly button. However, this allows me to spread the cream on her legs without actually bending at all.

As soon as I begin with the body cream, Michelle starts a conversation: "Timmy, how is it going with the chastity cage? Would you like to have to remove it and take a shower?"

I promptly reply: "Oh yes Mistress, I would love to have a break from it."

'All right, I will unlock you once are done with the cream at one condition."

"What condition?" I ask.

"I will ask you some questions about your feelings, and you must do your best to reply and be completely open to me. If you lie in your replies I might decide to not unlock you."

"I will reply honestly to your questions," I reply with a growing desire to have a break from the chastity cage.

"All right, all right. First question: how does it feel to not be a virgin anymore?" Michelle asks.

"Well, if I have to be honest, I have been with girls before..."

"Did they penetrate you?" She asks with an alarming tone.

"No no, I..."

"Then it was Sandra who took your virginity. How does it make you feel? And how does it make you feel with the fact that it was her to take it?" Michelle's tone becomes more and more serious.

I try to say, "It was not what I really wanted. As a man, I wanted to..." But Michelle grabs my chin and tells me with no smile on her face: "You are not replying to my question! How do you feel thinking at you losing your virginity in front of me by the hands and will of Sandra?"

"Mmh... Humiliated," I reply softly.

Michelle smiles, kisses me on the forehead, and says: "Oh I love when you give up and just speak the truth out. Second question: how does it feel to touch my naked body knowing that you cannot penetrate me because your dicklet is too tiny?"

Usually, it's Sandra who talks like this to me. However, while Sandra just enjoys humiliating me, Michelle gives me the impression that she really feels pleasure in seeing me full of humiliation. Anyway, now that Sandra is not present, I don't want to give up on this. I reply: "I can penetrate you, it's just that yesterday..."

Michelle doesn't let me finish the sentence. "Take off from these kid's clothes. Now!" she orders.

I obey. I remove my T-shirt and pants. She pulls down the front of my undies revealing my caged penis. "This tiny dick cannot penetrate me, no matter how hard you try. Do you understand? You are genetically not developed to penetrate me. Let's cut out all this man's pride bullshit. I want you to describe your feelings when you realize that your desire for penetration cannot be satisfied because you are too small."

Her tone, her height, all is intimidating.

"I feel helpless and impotent..." is all I can say.

She smiles again and puts my dick back to my undies. Then we start again with the body cream. It takes me quite some effort to spread it on her buttocks as my hands are small.

"Timmy, even if I would like you to be always honest with me, I love seeing your defense mechanism falls every time. Last question: given our size and strength difference, do you ever feel in danger in my presence? Do you feel like I could hurt you?" Michelle asks.

I didn't expect such a question. Both she and Sandra have indeed been lifting me up and moving me at their will with no effort, but in a real fight, I think I might have a chance. I reply: "Well... I would never fight you. But I don't feel in danger because I believe I would be able to fight you back if necessary."

"So you think you could fight me?"

"... Yes..." I reply sensing that something bad was coming.

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Michelle quickly bends her knees and inserts her hands in my undies from below my ass. Then she pulls the undies up until they form a wedgie. Looking at me in the eyes, she lifts me up. I was basically hanging midair from my undies. Michelle walks and sticks me to the wall, then asks me: "Do you really think you could fight me? Do you want to challenge me?"

"No no, Michelle, I would never challenge you, but please put me down now." I try reply.

"What about this wedgie? Why don't you react and fight me back? Or maybe you like it?"

I don't know what to say.

"Is it because your pride is getting one more time crushed by the evidence of our difference in size and strength?"

"Yes Michelle," I reply looking down.

"So, do you admit you cannot fight me?"

"I guess you are too strong for me, Michelle."

"Very well. And how does it make you feel to think that I am in such a power position that I can do whatever I want with you, and you don't have the strength to stop me?" Michelle asks me with a very serious tone.

"I am not scared because I deeply trust you." I find a smart answer.

"Ahah... If you believe that you can flatter me like that, you are wrong. Your head is smaller than my boob. I can do whatever I want with you!" She says a bit laughing while letting me down. As soon as I touch the floor I instantly take some steps away from her.

"Come here, I will give your dicklet a little bit of freedom." She takes the key and unlocks my chastity cage. She does it while still not wearing anything besides her thong. Her huge breasts have always had a hypnotic effect on me. She tells me smiling: "Take a good shower and keep yourself shaved below your head. Tonight we will have some of Sandra's teammates as guests, so be prepared!"

I am confused. What does she mean? She's about to leave the room when I ask "Prepared to what?"

"You must be all nice and clean as we will introduce you to our guests. You will be our friend, nothing more. Well... It's more up to Sandra how she wants to introduce you." A shiver runs down my spine. Michelle continues: "Anyway, don't worry too much. Now, stop staring at my boobs and go to shower! And no nasty things in the shower or you can only imagine what will happen." Then she leaves the room.

I obey. I shower and shave everywhere, even if I was still quite smooth. I realize that all the clothes I had were still only the ones that Sandra bought me. I put on a pair of undies with cute dinosaurs figures on them and I go to Michelle and ask: "How am I supposed to get dressed tonight?"

"With the clothes that you have. You know you wouldn't fit in any of our dresses." She replies quickly.

"But these are not clothes for an adult m..." I stop talking as her piercing look crosses me.

"You will wear the clothes that fit you. If you fit in these, that's what you are going to wear. Understood?"

"But they are not even elegant," I complain.

"Understood?" She repeats.

"Okay..." I say while giving up. I return to the bedroom but she follows me. I just feel my undies being pulled from the back and hear Sandra saying: "Where are you going? Aren't you forgetting anything?"

I was hoping she would forget. "Can we put it back tomorrow? I would like to be... ehm... free for tonight."

"Nope." He cuts short. She pulls the front of my undies down and she locks me up again. The key was now in a little chain that she put around her neck. "Now every time you stare at my boobs, you will see the chain. So that you remember who owns the power here." She kisses me on the cheek and leaves.

I get dressed in the best clothes available. Not long after, Sandra comes back home. First thing, she greets Michelle, then she comes and looks for me.

"Hi Timmy! Sorry for yesterday night. I hope you had fun after all. Tonight, two of my teammates are coming over for some drinks. We will order some food. Please behave and try to be polite with everyone!"

"Hi, Sand.. Mistress! Yes, Michelle told me everything, I will be happy to meet your teammates." I say.

"Ahah... you don't have to call me Mistress outside the bed unless you want to!" She says laughing. "I think my friends would find it funny, but better not overdo it and just call me by my name tonight. Ok?"

"Ok!" I replied happily. At the same time, I feel that Sandra is not being herself. Maybe she's stressed about her friends coming over.

About 30 minutes after I heard the doorbell ringing. "Oh Timmy, please open the door and let them in!" Sandra asks.

I go to the door and open. I find myself in front of two young, tall, and gorgeous girls, probably as tall as Sandra. "Hello! Welcome! Please come in." I say thinking that I could have realized before that the teammates of Sandra would have probably been as tall as her given that they play volleyball professionally.

"Hello! Who are you?" Says the first girl smiling down at me. "I didn't know it was a pajama party..." Whispers the second girl, probably alluding to my clothing.

"I am Timothy, and I am a friend of Sandra and Michelle," I say shyly,

"Nice to meet you Thimoty, my name is Rebecca, and she's Emma." Says the first girl. She has long, curly brown hair, big green eyes, and a gorgeous smile.

"Hi, nice to meet you!" Emma follows. She has long, straight and red hair and brown eyes. I notice that both of them were pretty muscolar. Also, the fact that Emma was wearing leggings made her legs look particularly long.

"Hi, Emma! Hi Rebecca! Welcome!" Says Sandra.

"Hi, girls!" Follows Michelle, making me think that it was not the first time they met.

After a bit of chit-chatting, we move to the living room, Emma and Sandra sitting on the sofa, the rest of us sitting on three chairs. Quite soon the conversation converges to me.

"How did you meet Sandra and Michelle?" Asks Emma.

"We met in a pub after work." Michelle anticipates me.

"Oh, nice! And what do you do for a living?" Asks again Emma

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"He is really good at cooking. So we decided to hire him to cook for us." Again Michelle replies for me.

"That's sweet!" Emma replies. "And do you live here as well?"

In a fraction of a second, I look at Sandra, she is just observing, but I see in her eyes no intention to intervene in the conversation. I am thinking about what I should reply, but Michelle again replies for me: "Yes, he lives with us for now until he finds a better accommodation."

"Oh! My dad is renting our studio flat not so far from here. If you are interested, I can bring you to see it." says Rebecca.

"Thank you, that would be nice," I reply trying to not show too much interest. I look at Michelle and I see a slight sign of annoyance on her face.

"And how is it to live with two gorgeous women like Sanrda and Michelle?" Says Rebecca with an entertained tone. "Oh, they are the best hosts!" I reply.

"He is a good guest as well. And if we have any disagreement, we just sort it out in peace" Sandra adds, "Right Timmy?" I nod. For the first time she calls me Timmy in front of Emma and Rebecca. I see indeed that Rebecca makes a half laugh when she hears it.

"And where do you sleep? Isn't there only one bedroom in this apartment?" Rebecca keeps asking. I am about to reply that I sleep on the sofa in the living room, but Michelle anticipates me one more time: "He sleeps in the bedroom with us."

"Whaat?" Rebecca and Emma are both surprised and entertained. Sandra looks as if she is holding back a laugh. "You are such a lucky boy to sleep in the same room with these two stunning girls at your age! This is a dream for anyone of your age!"

It is clear that they think I am way younger than what I am. I want to change the subject but I am out of ideas for diverging the conversation. Then Sandra intervenes. "Ahah no no no. He looks young but he's older than all of us!"

"Really? I thought you were 20 years old or something" speaks Emma.

"Ehm... no..." I mumble.

"Ahah don't look at him like that! This little boy has a lot of resources that you could never imagine!"

"Oh, you are a boy full of mysteries! Are you good only at cooking or are you good at something else as well?" Rebecca asks. I don't understand her question, so I take time to reply.

"Oooh you can't imagine Rebecca! Well... as you know me and Michelle are not interested luckily, otherwise we would have to face the competition! Timmy?"

"Well... I..." I mumble again.

"Oh Sandra stop joking with us. I don't buy a single word of this. I bet he's 20 years old and... he's still a virgin." Emma intervenes.

"He is not a virgin." Michelle talks. Her tone is serious and she is clearly annoyed by where the conversation is going. But Sandra, on the other hand, is having fun: "No no no, he's not a virgin at all! Right Timmy?" Then she looks at me. "Oh no, I am not a virgin at all! I might look young eh eh... but I am older and therefore more experienced than all of you girls!" I realize that I probably went too far. I hear Emma and Sandra laughing. Rebecca too, but at the same time I see her staring at me intrigued. Michelle, on the other hand, has an angry face.

Then, Sandra adds: "His dick is made of steel." This made my blood run cold.

"Ahaha com'on! I told you don't buy!" Emma exclamates.

"Eehh you never know what surprise you can ever find!" I dare to say. Michelle is looking at me furious.

"Michelle, would you please help me show Emma that Timmy's dick is as hard as steel?" Sandra asks.

I am paralyzed. I cannot predict what is going to happen. Emma and Rebecca look shocked as well by the words of Sandra. Michelle gets up and walks towards me. I see her angry face while she walks around my chair. I try to say: "Michelle... I..." But she grabs me from below the armpits and lifts me from the chair. With a kick, she moves the chair from below me, so that I am just there hanging in the air with her holding me.

"Michelle... please..." I complain, but I am still unsure of how to behave in this situation. "Timmy, you talked already. Now you have to meet the expectations."

Sandra comes close to me, this time with her usual wicked smile I got to know too well in the past days. "I will show you now."

She opens my pants from the front and pulls them down all the way to my feet, exposing my undies with dinosaurs. I hear the girls laughing. Only Michelle stays serious. Rebecca gets closer and tries to touch the undies but Sandra stops her: "No no Rebecca, you can watch but you can't touch."

"Ahahah all right! Sorry! I just love these undies." She says laughing while sitting back. "Oh sure there is a dick made of steel there inside," says ironically Emma.

"Oh Emma, you are wrong again! Silence please..." Sandra snaps her index finger on my undies above my chastity cage. The noise of her nail against the metal below the cage makes a metallic sound that silences everyone. "I told you, Emma," Sandra concludes smiling.

Michelle puts me down. She looks at Sandra, this time not with an angry face. She looks as if she was surprised as well by what Sandra did. She probably thought Sandra was going to take my undies down to humiliate me, and she was up for it.

As soon as I am free, I pull my pants up. There is silence in the room, so to lighten the mood I say: "Eheh... I am full of surprises." Then I leave the room and go to the kitchen pretending to do something. I hear the girls chatting but I cannot hear them clearly as their voice tone is low. When I come back, they all look at me.

Rebecca asks me with a serious tone: "What do you have between your legs?"

"Ehm... Nothing." I reply. "That's accurate!" Sandra adds making everyone laugh.

"Can I see what does he have inside his undies?" Rebecca asks directly to Michelle. Michelle looks at her, taking time to reply, then finally she says: "Ok you can but on one condition: I will let him fight you off."

The words of Michelle seem to please Rebecca and gets up all of a sudden. "Fight her! Show me how strong you are and don't let her touch you there!" Michelle yells at me. Sandra and Emma are ready to watch the show.

I put my hands in front and said: "Hey wait a second..." But Rebecca is already on me. She bends down, wraps her arms around me, and lifts me so that I lay on her shoulder. With one hand she holds me still on her, with the other hand she takes off my shoes. Then she puts me down again saying: "Shoes are off."

She wants to undress me, and I am ready to fight. She comes again a me but this time she directly grabs my t-shirt. I grab her wrists to stop her from pulling my t-shirt up, but then she looks at me smiling and, as she lifts up her hands, she lifts me up as well in mid-air. I try to hold still but soon I get tired and I let go. As I fall down, Rebecca keeps her hands up, and so my t-shirt slips off of me. "T-shirt is off." She adds while trowing it far on the floor.

I cannot allow myself to get undressed against my will by this girl younger than me I had just met. I decide now to run away but as I am at my second step, I feel her pulling my pants and me back towards her. She is completely over me with all her body. Looking up, I can see her hair and her face looking down. Her long arms go down to unbutton my pants and, even if I try to stop her, she is too strong and I cannot do much. She then turns me around so that she can look at me in the face, still with her hands on my pants.

She looks at me and says: "Are you ready? Five... Four..."

I understand she wants to pull my pants down.

"Tree..."

I try to stop her but all of a sudden my pants are already down.

"Hahah you didn't expect that! You thought I was going down to one." Rebecca laughs. Sandra and Emma are laughing loudly too. Michelle, on the other hand, is looking at us with her mouth open, trying to not miss any moment of what is happening. "Fight Timmy! Fight harder!" I hear Sandra saying.

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