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Questions every Mistress needs to ask a sissy

Why Mistress will ask a sissy questions

Listen to me read you this blog about questions for a sissy.sissy questions from Experienced Mistress Olivia 1-800-601-7259

Don’t worry; it won’t be an interrogation (unless you’re into erotic interrogation and being ordered to tell your naughty secrets).  I have some basic questions at the beginning of an encounter with someone with physically male “parts” but presenting en femme.

Basic communication with your Mistress

Here are some general tips to make sure you have your best phone sex ever! Now, for some girly girl specific ideas from a friend who is a delightful sissy!

Sissy Questions

Here are the questions from a caller:
  • Your name – What do you call yourself and why? (That’s her favorite question).
  • Style of play – do you like to be treasured or belittled, commanded or led, indulged or prevented?  (Her second favorite question).
  • Describe your perfect fetish experience?
  • Have you done any “real life” play?  If so, do you want to do more face to face encounters and just need encouragement (or orders)?
  • What do you do to regularly connect to your inner sissy?  (The best example of this is wearing panties every day).
I want you to add to the questions in the comments, or we can talk about this and much more in your call.

Your Experienced Mistress,

Ms Olivia

15 comments to Questions every Mistress needs to ask a sissy

  • princess

    As a denied sissy cuckold in chastity…..i ld ove to be humbled, ordered and controlled….oh, and i do shave and wear panties everyday! Great post 🙂

    • Olivia

      And I know who controls you, princess — your Mistress, Miss Constance, is a dear friend and fucking spot on with what to do with a sissy! 🙂 🙂

  • sal

    Hi Mistress Olivia I am new to this phone calling but I do read everything you put online of all the woman online to me you are the sexiest I am a secret sissy who loves to wear panties stockings and heels I have more female clothing than male I would love to talk to you about this secret of mine how easy can you make this for me I am a shy person would you be able to get back to me and let me know thank you Mistress Olivia enjoy your day

    • Olivia

      Ohhhhhh a shy sissy is a sissy to years to break free !!! Am I right? I know I am. I’m here during the day eastern time. You can tell if I’m on a call by looking at the availability icon on the right side of the home page of this blog. You can also send me an email: olivia AT and I can tell you more about how we can connect. Oh and sweetie, I LOVE that you have more female clothing than male! Good sissy!

      • sal

        Hi Mistress Olivia i sent a question to you on oct 24 i just saw that you responded i found it by mistake i am a secret sissy i love wearing panties heels and stockings im not to good at putting on make up i wish i had somebody to help me you also said you love that i have more female clothing than male also you said i can send you an e mail about how we can connect would you get back to me when you have a free minute and let me know my e mail is thank you Mistress Olivia have a wonderful evening

        • Olivia

          Hi there sissy … secret sissy is a very popular kind of sissy and I can absolutely put you on a sissy training program. Are you able to do calls? I’m asking that because you’re asking for emails. If you need an email training program that’s totally fine as well. My email is olivia AT
          And you can call me at: 1-800-721-1962. Just ask for me 🙂

  • Owen

    To me it feels a bit good to simply be called a sissy. I think it is because that is how I feel and there is a kind of truth that the word conveys for me. In terms of an actual name I am not sure but I do feel like a sissy when women call me things that are slightly feminine or make me question whether they are seeing me as more female than male. Those are simple words like “honey” or “sweetie” or anything that has a slightly feminine feel and that I know they would not use in that way with their boyfriends or other more manly men. I think my perfect fetish experience is when a woman makes me dress for her. I dont know what this does to me exactly but it is incredible. I have this feeling that I have to comply and that I am just an amusement or a doll for her to play with and am zero sexual threat to her. I am like a toy. I have done “real play” though it was not a choice it was more of something sprung upon me by a female friend. She made me dress up. I have had a number of these occurances. To “connect” with my “inner sissy”. I am near bras, panties and slips and also measure myself.

  • Olivia

    Ms Erika and Ms Delia told me you’re in chastity … that’s exactly where you need to be petey cream puff … ~laughs~

  • chrissy

    HI Mistress Olivia,
    I woke up this morning thinking about you and how much I love to wear panties for you. I put on my favorite white silk panties, a lace camisole and high heels. I was so disappointed to find you were not working today. I don’t want to call anyone else. I want to be your sissy girl all the time. I call myself Chrissy because my male name is Chris but it feels much more correct to use the female form of the name. I was never very good at being a boy. I am tiny and feel so good in feminine clothes. As far as play I like to be a subby sissy for my mistress and serve her (you) in any way that pleases her. I like to be humiliated and laughed at for my short comings as a male but also cherished as a sissy – mostly I like to be kept in my submissive place to please mistress. I love all things girly! to connect to my inner sissy I try to wear something feminine everyday- often panties but sometimes I tie a ribbon around my cliffy as a reminder of who I really am.

    Sissy Chrissy

    • Olivia

      Ohhhhh sissy chrissy … that ribbon around your clitty is perfect! I often suggest that because well, it’s visual (obviously) AND sensory … and you do look perfect in your white panties!

  • Dick Breath Sissy JayMe

    To remain in touch with my Inner Sissy I shave like a woman and every day have some makeup on, at least B.B. creme if not foundation & powder on some days. And ALWAYS mascara and at minimum a tinted lip balm, some days lipstick.
    My supervisor at work sells Mary Kay on the side and hosts parties. She once ordered me to sit as her model to demonstrate various items of makeup, for a room full of amused women.
    Of course I wear panties. This has raised attention at the laundromat.

  • Sissy Candy

    My name rather goes back to the time I was trying to find out why being neither comfortable nor able to ‘role play’ being a male nor having any great feeling toward womanhood either, getting in touch with a Mistress where we agreed Candy was a sweet name whose latin origins fit me to a tee.
    For me this neitherness is a core thing as is submissiveness.
    To me it’s really about just being who you are, making the most of it rather than wasting time pretending your something you’re not and this whole thing just is so calming while returning being the ‘sissy’ I was back then.

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