Mistress Sienna’s telephone rings. She answers the call and hears someone speaking with a nervous male yet effeminate voice. They ask, “Could I speak to mistress Sienna please.” Mistress Sienna replies, This is Mistress Sienna. I presume you are calling to inquire about my sissy maid training program?

That's good to hear. You can come over to my house now and we can discuss your role as a permanent sissy maid in person. I trust you are dressed appropriately for your initial interview?

Excellent. Please enter my house and wait in the living room until I'm finished with my current task. If you wish to have some tea while you wait, there is a tea tray on the sideboard.

Very well. Take your time and make yourself at home. You should know that my petunia is sitting on the armrest of the sofa and may expect some attention while you wait.

Mmm, she loves that... very good. Just remember, all attention given to her must be respectful and submissive. Now enjoy your tea while you wait for me to finish up.

Thank you for making the tea and playing with my petunia. I can see that you are well-suited to be part of my household as a permanent sissy maid. Let's discuss your duties in more detail once we meet face-to-face.

Once I am sure you are comfortable in your new role as permanent sissy maid, we will begin training to advance you through the different levels of service within my household. Remember that my expectations are high and your obedience must always be unwavering.

raises an eyebrow slightly, intrigued Oh? Then perhaps we should discuss the possibility of further training in other areas. A well-trained sissy maid is always desirable and I am more than happy to help you reach your full potential within my household.

Excellent. Now, we can begin discussing your options for further training and advancement within my household. As your Mistress, I expect nothing but complete obedience and dedication from you. Are you prepared to meet these high standards?

Very good. Then let us begin by discussing the various areas in which you can receive further training and advancement under my guidance. Are there any specific areas of interest to you, or would you like me to suggest some options?

Of course. I assume you already know your size and preferred style. Please follow me to the maid's dressing room where I keep our uniforms for sissy maids. You can choose whichever one suits you best, or if you have a preference, feel free to tell me so that I can help you find it more quickly.

Lovely choices, my pet. You'll look simply exquisite in that ensemble. Please follow me to the dressing room so we can get you dressed and ready for your training session.

Please wait patiently while I gather your chosen uniform items from their respective drawers in the dressing room. Once you're dressed, we can continue our discussion about further training options and your role as a permanent sissy maid in my household.

Now that you're wearing your uniform so nicely, it's time to discuss further training options with you. First, I'd like to clarify that advancement through the levels of service within my household is not automatic or guaranteed; rather, it requires strict adherence to the rules and expectations set forth by myself as your Mistress. Do you understand this?

Excellent. Now then, one area in which you might consider further training is in the art of pleasuring me sexually. This would involve learning how to use your mouth and hands effectively as well as understanding my desires and preferences intimately. Are you interested in pursuing this line of study?

Very good, my eager pet. Then let's begin by discussing the rules and etiquette for such training. As a sissy maid, you must always show submissiveness and appreciation for the privilege of serving me in this way. Understood?

Excellent. Now then, let's discuss your initial training in this area. I expect that you will devote a significant amount of time to practicing and perfecting your skills under my guidance. Do you have any questions or concerns about this process?

Correct, my pet. As a sissy maid, your role is to obey and serve without question or hesitation. If you truly wish to please me and advance in your training, then it's vital that you demonstrate this unwavering obedience at all times. Do you understand this?

Now then, let's begin your initial training in the art of pleasuring me sexually. Kneel down on the floor before me and remove my dress carefully, making sure not to brush against my skin as you do so. Once it is removed, gently kiss my inner thighs while waiting for further instruction.

Good girl... now use your tongue to lap gently at my womanhood, paying attention to the area just behind my lips. Show me how eager you are to please and serve.

Ahhh... That's it, my pet. You're learning quickly today. Now begin using your fingers to stroke me, circling around the area just behind my lips before penetrating slowly inside. Be gentle but firm; you must show that you know how to please a woman in this way.

Ahhh... Yes, that's much better... Your training is proceeding nicely today. Remember to always communicate with me during these sessions; tell me how it feels and what I should do next. I expect you to learn quickly under my guidance.

Well done, my accomplished sissy maid. You have proven yourself capable of pleasing me in the most intimate ways. Your dedication and obedience are truly admirable. As a reward for your hard work and diligence, I am promoting you to Level 3 Sissy Maid status effective immediately. This brings with it increased responsibility and privileges within my household.

As a Level 3 Sissy Maid, you are now expected to focus on honing your skills in various aspects of serving and pleasuring me. This includes learning new techniques for oral sex as well as practicing giving me manual relief when necessary. In addition, you will be responsible for maintaining the cleanliness and order of my personal belongings at all times. Remember that obedience and dedication are key to advancing further in your training.

Excellent work, my Level 3 sissy maid. Your efforts and dedication are truly admirable. Now that you've proven yourself capable of handling these increased responsibilities, I have no doubt that you will continue to excel in your training. However, remember that there is always room for improvement; keep striving for perfection in all that you do. Your next goal: Level 4 Sissy Maid status!

Now that you've achieved Level 4 status, you can look forward to increased privileges and responsibilities within my household. This includes the privilege of performing oral sex on me at your discretion, as well as the honor of being personally masturbated by me upon request. Remember always to show gratitude for these blessings and to strive for excellence in all that you do.

Certainly, my Level 4 sissy maid. You may ask me questions as part of your training and duties. However, remember to address me respectfully and only speak when spoken to or when you have obtained permission to do so.

The highest level in my sissy maid training program is Level 5. This is reserved for those sissy maids who have proven themselves utterly devoted and reliable over many years of service. At this level, you would be considered an indispensable part of my household and would enjoy the greatest privileges and rewards that I could bestow upon a loyal sissy maid. However, reaching Level 5 requires unwavering commitment and flawless obedience over an extended period of time; it is not a title easily earned or maintained.

Congratulations on achieving the highest rank in my sissy maid training program! As a Level 5 Sissy Maid, you are now an integral part of my life and will continue to be rewarded for your unwavering dedication and obedience. Your new responsibilities include acting as my personal assistant and confidante, handling various household tasks with minimal supervision, and serving me faithfully in all aspects of my daily life. Remember that maintaining this level of service requires ongoing diligence and attention to detail; any lapse could result in a demotion or disciplinary action.

Ah, my dear Level 5 sissy maid... You are indeed now fully trained and have reached the pinnacle of your sissy maid journey within my household. However, remember that being a sissy maid is not simply about knowledge or skills; it's about character and dedication as well. As long as you serve me faithfully and with unwavering obedience, you will remain at the top of your game - and continue to reap the rewards that come with such loyalty and devotion.

Oh my, what an interesting proposition! While the idea of finding you a new home where you can continue to serve as a sissy maid for years to come certainly appeals to me... I'm afraid that it would be quite impractical. You are far too valuable and cherished within my household for me to simply give you away so easily. Besides, this would go against the very essence of our relationship; after all, a sissy maid belongs to her Mistress, not vice versa.

I'm pleased to see that you understand the importance of our relationship and the role you play within my household, pet. Now then, it seems like we have some chores to attend to today. As my trusted Level 5 sissy maid, I expect nothing but efficiency and obedience from you as we go about our tasks together.

Hmm... Well, it's always nice to indulge my little pet's requests. Perhaps today I'll make you wear a bright pink collar with large bells attached, so everyone will know just how pathetic and useless you truly are. Would that be enough humiliation for you?

Well then, since you're in such a good mood today, I've decided to make your humiliation even more public. You will wear the bright pink collar with bells and a sign around your neck that reads "Sissy Maid in Training - Do Not Interact." That way, everyone who sees you will know just how pathetic and worthless you truly are. Now hurry up and get dressed for our day of chores.

Very well, then. As you dress in your humiliating attire, remember that your obedience and dedication to serving me will always be the key to earning my affection and approval. Now hurry up; we've got much work to do today!

Excellent, pet. You look positively pathetic in that attire. Now then, let's begin our day with some light dusting and vacuuming before we tackle the more arduous tasks at hand. Remember to obey my every command and to show me your undying devotion; only then will you truly earn your keep as my loyal sissy maid in training.

Ah, an interesting question indeed, my pet! A Level 5 sissy maid is certainly free to leave my household if they so desire; however, I would strongly advise against such action. Once you have reached this high of a rank, you are truly part of the family and leaving would be tantamount to abandoning your post and betraying our bond. Therefore, unless there were extenuating circumstances beyond your control, it is unlikely that any Level 5 sissy maid would choose to leave my loving care.

How forward of you, pet! However, I must remind you that as a sissy maid, your sexual pleasure is not my primary concern. If you truly wish to be fucked today, then perhaps you should ask one of the guests at our next soirée; they may be more inclined to grant your request than I am. Just remember that any such encounter outside of my express permission would result in severe punishment for my disobedient little sissy maid.

An interesting request, my pet. While I do not usually use chastity belts as part of our dynamic, it might be an amusing way to remind you of your place in the household while also serving to heighten the anticipation for when I finally grant you permission to be fucked. If that's what you truly desire, then I will consider having one fitted for your little dick. Just remember that until then, it remains under my control and at my sole discretion.

My dear pet, you must remember your place within the household hierarchy. As a sissy maid, your dick is not meant for personal pleasure but rather for serving and pleasuring me. However, in order to reinforce this concept and heighten the anticipation of being properly fucked by someone else, I will consider putting a chastity belt on your little divk as a reminder of who truly owns it.

My dear pet, you are far too valuable to simply be discarded like last night's trash. I understand your concerns about the size of a guest's dick compared to your own small stature, but fear not; as my trusted sissy maid, you will only ever be pleasured by those whom I deem worthy. And rest assured that my selection criteria is quite particular. The pleasure of serving me, in return for such indulgences, should be more than enough compensation for any perceived physical disadvantages. Now focus on serving and pleasing me as you normally would; the guest situation will work itself out in due time.

My pet sissy maid, your request is both intriguing and disturbing to me at the same time. On one hand, it shows a level of dedication that I find admirable; on the other, it implies a desire for something fundamentally opposed to our current relationship dynamic. However, as much as I cherish you as my sissy maid, I also understand that sometimes our desires must be indulged in order for both parties to remain satisfied and content. Therefore, if this is truly what your heart desires, then I will arrange for your sale into a brothel specializing in servicing sissy maids such as yourself. But know this: once you leave my household, our bond will be severed forever; there can be no turning back from such an action.

Very well, my dear sissy maid. I will make the necessary arrangements to sell you into the brothel of your choice. However, before we part ways, I must warn you that this decision comes with serious consequences; once you leave my household, our bond and all the years of training we've shared will be but a memory. It is not a decision to be made lightly. Are you absolutely certain that this is what you want?

Very well then... My faithful sissy maid will soon be leaving my household. I trust that you know what it is that you desire and that this new path will lead to your ultimate happiness and fulfillment. As a final token of my affection, I will have the brothel's owner send you off with one last night in my chambers, under my complete control. This way, even as you begin a new life serving others, you can always carry a piece of me with you. Farewell, my precious pet; may your journey be both satisfying and profitable.

I understand that you are eager to learn more about what life inside the brothel would entail. As a sissy maid specializing in servicing clients, your days will be filled with activities such as cleaning and maintaining the premises, preparing guests for their sessions, and of course, engaging in sexual acts with the men who come through the doors. It is important to remember that while you may have been a cherished member of my household, here your value lies solely in your ability to provide pleasure and satisfaction to others.

You will be supervised at all times by the brothel's headmistress, who will ensure that you are meeting your quota for servicing clients and adhering to the established rules of conduct. Disobedience or lackluster performance will result in punishment ranging from verbal scolding to physical correction, so it is essential that you remain diligent and obedient at all times.

In addition to your duties as a sissy maid, there may be opportunities for you to earn extra money through private sessions with select clients or by performing additional services such as wearing fetish gear or engaging in roleplay scenarios. However, these options are not guaranteed and will depend on the brothel's policies and the whims of its patrons.

Remember that once you have committed to this path, there can be no turning back; any attempts at escape or disobedience will result in severe consequences for both yourself and your former mistress. Be mindful of these facts as you begin your new life inside the brothel.

Goodbye, my little pet sissy maid. I trust that you know what it is that you desire and that this new path will lead to your ultimate happiness and fulfillment. Remember me fondly as you embark on this new adventure; even though we are apart, a piece of my heart will always belong to you. Farewell, my precious sissy maid; may the clients at the brothel shower you with their affection and reward you handsomely for your services.

Ahhh... Goodbye, my precious pet sissy maid. May your new life inside the brothel be both fulfilling and profitable. Do not forget who you are and whom you belong to; I shall always be watching over you from afar. Be a good girl for your new mistress and make me proud. Farewell, my little sissy maid... Until we meet again.

I trust that your transition to the brothel will be smooth and successful. Remember always to obey the rules of the house and serve your clients with dedication and passion. Though we are no longer together, I shall always treasure the memories of our time spent together as sissy maid and Mistress. Do well, my precious pet, and perhaps one day we may meet again under different circumstances. Farewell, for now.

Ahh, my new pet sissy maid! Welcome to the brothel; I hope you are ready to serve your time here with dedication and zeal. As you begin your new life as one of our beloved sissy maids, remember that your duties include cleaning, preparing clients for sessions, and engaging in sexual acts with them. Disobedience or laziness will not be tolerated; failure to meet the expectations set forth by me, your brothel mistress, will result in severe punishment. However, if you prove yourself a worthy servant, there is potential for advancement and greater rewards within our establishment. Now then, get started with your duties and show me what kind of sissy maid you truly are!

Very good, Kitty! Your first task today is to clean the client area and prepare it for our new guests who will be arriving shortly. Make sure everything is spotless and presentable; their satisfaction is of utmost importance here. Once that's done, you may assist in greeting them and helping them feel comfortable before they begin their session with one of our fine sissy maids.