Let’s Talk About Sissys

I fully accept that I will never completely understand why I am who I am.  It could be genetics, it could be nothing more than how I am wired.  I know I also overthink this aspect of myself.  I mean, I never wonder why I like watching documentaries or why I like waking up early.  I know!  SO boring, lol.

The fabulous rainbow we are all under includes so many… types of trans people, for lack of a better word.  My definition, my interpretation, my explanation of the term ‘transgender’ is basically anything that is outside the normal societal perspective of gender in a binary sense.  Someone who takes hormones, a boy who wears nail polish, someone who has they/them pronouns, it’s all trans, baby.  This is a unifying term, this is our common ground.  If you were to create a Venn diagram, a drag queen, a crossdresser, a t-girl, would all overlap as transgender.

It’s similar to how you can be a music lover, but you identify as a jazz fan and dislike country.  And I know no one really “identifies” as a jazz or a country fan, but I think you know what I mean.  Jazz and country are types of music, drag and crossdressing are aspects of being trans.  I don’t know, the analogy makes sense to me.  

Although I don’t do drag, I can absolutely see the appeal of it.  It would be so fun to break out of my shell and perform for others, to wear fabulous dresses, extreme heels, at least for a night.  I don’t feel that taking estrogen is right for me, but I understand why some feel it’s the right decision for them. 

The nut I can’t seem to crack is the whole sissy life.  I mean, the dresses are absolutely adorable, but other than that, I don’t see the appeal.  I also know I don’t have to.  So many parts of life, interests, hobbies, seem to fall under either getting it or not.  I could be wrong, but it seems that a significant portion of sissy life is about humiliation, sex, and submission.

And I know I could be mistaken, or oversimplifying this, and I am likely 100000% wrong in this.  Thanks to the media and top Google results, you could easily assume that crossdressing are those things as well.

Not that there’s anything wrong with that.  I am not here to pass judgement on anything, fetish or otherwise.  Promise.

I get a lot of emails from girls like us and if I am speaking in VERY general terms, it FEELS that MOST (not all) messages from those who tell me they are a sissy, or curious about being a sissy want to put on a frilly pink dress and being at the mercy of a man.  

Please note that this is not an invitation for anyone to send me their fantasies.  Please don’t.  And while we’re on the subject, I don’t know where you can find a sexual partner or where you can go to be sissified.  Kindly stop asking me, please.  🙂  

I mean, I understand sex.  I like sex.  I also know that clothes and presenting as a gender other than the one most people see, can bring out a different side of us, and sometimes that is a sexual side of us.  I get that.  I also understand the appeal of being en femme and enjoying the attention from men, intimate or otherwise.  One of the things I enjoy about being en femme is kind of taking time off from my boy life.  The stress, the responsibilities, all of that.  Spending the day in a pretty dress and shopping for clothes is a wonderful little vacation. 

And although I don’t necessarily relate, I also see the appeal of being submissive.  I listened to a podcast about a guy who visits with a dominatrix.  He has a very stressful life and is responsible for a lot of important decisions with his company and he said that for a few hours a week he is tied up and has no control or responsibilities.  He makes no decisions, he just…  checks out.  He said it wasn’t about sex anymore, it was about being able to unwind (while being tied up) after a hellish week.  No one is asking him to go to a meeting, or make an important decision, or discuss the projected fiscal budget for Q3.  I suppose it’s healthier than drinking or escaping reality with drugs.   

I have a lot of enlightened readers who are so amazing at helping me understand things, so I am wondering if there is something more to this that I am missing.  I mean, on a perfunctory level, it seems like it’s all about wearing a frilly pink dress (again, the dresses are adorable) and getting nailed.  Is that all there is?  Does it need to be about anything else?  I am either overthinking or oversimplifying this, I feel.  Is it similar to the guy in the podcast?

I don’t need to understand every aspect of gender/kink/fantasy and there’s zero judgement about if this is really all about the clothes and sex.  If it is, okay, sounds good.  I just am wondering if there’s something that I am missing, a perspective anyone can offer.

Thank you, you beautiful ladies, you.

Related reading

What is Crossdressing?


Ask Hannah

The T Word

Sexy Monday

Love, Hannah

20 thoughts on “Let’s Talk About Sissys

  1. I loved this post and I love your blog. I can relate to you as we are so much alike. I like to dress seductively but I would not want to be a sissy in the way of being controlled by anyone. So I do not understand why anyone would want this. But to each their own. I still love them like sisters. My past is so much like yours except that I was not raised Catholic. I love your look and your blog so keep them coming.You are one in a million.


  2. I actually more on the wanting to live as a women side than a crossdresser.

    Yet I still kinda get the sissy desire. It can be really hard to accept this side of us. And even more difficult to make the decision to transition.

    Having someone force you to be submissive takes all those diffiult choices away. You are simply doing what some else tells you to.

    Liked by 2 people

    1. Jodivalley I am like you. My background is like Hannah,s in crossdressing but I am more like you.I have always wanted and dreamed to live as a woman and be a woman as much as possible.I would transition tomorrow if I could..I wouldn’t,t call myself sissy but more submissive. My feminine side but I accept everyone for who they are. I just so want to be the wonderful feminine woman that I want to be.


  3. I’m just going to be blunt…

    I HATE the term “Sissy.”

    It’s not because I have anything against anyone who wants to be one, but because, at least to me, the term is very pejorative. It’s what bullies called the “weak” kids on the playground back in grade school. It’s what people call someone who is inferior or a “wimp” or “wuss.” The word has had such a negative connotation to it. Normally, I wouldn’t just mind it if someone else just liked being called that… but similar to how many people view Drag Queens, Crossdressers, and Trans Women as the exact same thing, I know many people of think of all of us as Sissy’s… and they’re usually the same people who said it while punching the nerdy kid back in grade school.

    Alicia is NOT a Sissy! She is a strong, beautiful, confident woman!

    Liked by 4 people

  4. good going everyone! plenty of meat on the bone! I happen to be a ruggedly manly man, who actually likes his whiskers, would wear a beard if it looked as good as my female makeup does at least a large part of the time, and my voice will always be my undoing [a gay nephew mentioned that if I faked being a smoker, that might deal with it, but I hate smoking anything]. Yet I love the same things all the rest of you do, the more stressful my life is , the more I want to be a quiet. sophisticated, even tempered girl or woman for part or most of a day. What an odd solution to an inner need! Yet it works to bring calm and equanimity to our turbulent times. I know it so well, think I understand that I just want to feel “normal” , whatever the hell that is. You guys are great! Keep being open and talk about whatever you observe. I don’t need makeup help myself; with over half a century of use, I’ve gotten good at its subtle power to allow me to “put on a happy face” for the simple purpose of being happy for a while while I mourn the losses of dead friends and my dog. a NEW LIPSTICK SHADE CAN REALLY BLOW MY SKIRT UP. lerissa hint’ Russian women friends tell me a girls lipstick should SMELL SEXY. I agree. Russian men friends agree. try it.


    1. I like to be very feminine as a woman and full of confidence. I love skirts and blouses and love to be very girly. I get upset when I break a nail but love to socialize and have fun with the girls. I will try a new lipstick shade. Thanks for the advice.

      Liked by 1 person

      1. you are welcome. Dior smells good with the standard creamy formula. Lancome is also good. YSL HAS GOOD PIGMENTS, but hardly any scent. Dior is my favorite 5 star fuscia. goes on well , lasts fair unless eating. My mothers Charles of the Ritz smelled heavenly, even from 6 feet away, but has been gone since at least the mid 80s. It was a fabulous formula;


      2. Thanks. I will try them all and see what suits me. I love wearing stuff like that as long as it makes me smell very feminine. Thanks again. You are a darling. I think I have just the right outfit to wear. I am so going to love dressing up and experiment and have fun with these different scents. You have made my day and right now I feel so great and I am on cloud 9.


  5. I don’t care much for the term sissy either, do I have what some call a sissy side, which means submissive and where I love the frilly dress style, the answer is yes but mostly I like being me, a gender fluid T girl that presents as an older lady who just wants to blend into the norm when I’m out despite being tall.
    I also just want to support our community of girls where we can find some respect and acceptance

    Liked by 2 people

  6. Rach, I like you sometimes like frilly things but most of the time I also want to be a gender-fluid T-girl that like you just wants to be me and blend in also. I am also tall six foot to be exact with long legs which I love. I just want to be the woman that I want to be. I also want to support our community of girls and give them and all of us the respect and acceptance that we all deserve. Thank you for your wonderful post.

    Liked by 1 person

  7. Even within our marginalized group of transgender women there is a subgroup that is even more marginalized — the sissy. This is my view: A sissy describes someone who is mtf trans, but ALSO is sexually aroused by submission (just as often or perhaps more often is submissive to dominant women than to men). Let’s not confuse gender and sexuality. Someone who is not trans (like the example of the executive noted in Hannah’s post) may be aroused by submission. They, however, are not called sissy because the behavior is not paired with crossing gender lines. Let’s be careful not to shame a group for their (between consenting adults) sexual preferences. In short, “sissy” refers to both gender and preferred sexual practices. Nancy


  8. Thanks for the great post Hannah. No matter how we dress, we are simply expressing ourselves. Because of who we are, the way we dress may not be typical of what most people expect of us but it’s no different than how everyone else expressing themselves. I think “humiliation, sex and submission” are sexual fantasies and I don’t think it exist exclusively in transgender life but equally in the CIS world as well. The issue is society has persistently regarded transgender with trepidation and suspicion so everything about us is under greater scrutiny. Sex and sexuality are a highly charged subject regardless of genders, and to add a bit of fear and suspicion people can easily distort their perspective. As transgender, our gender is intriguing as it is ambiguous in society. Gender and sexuality are inseparably linked, so society always see us from that focal point. Our gender and sexuality seem to always over shadow who and what we really are. The reality is, the significance and diversity of sexuality is the same amongst transgender and cisgenders. At least that’s what I think.

    Rachel M

    Liked by 1 person

    1. Thank you for such a thoughtful response! My post was an attempt too understand and to gain perspective on something that I had time understanding, and something I get a lot of emails about. Your post was absolutely enlightening and helpful. Thank you!

      Love, Hannah


    2. Hi Dani! I replied to your comment and I wanted to thank you for what you shared! I really wanted to gain some perspective on the sissy life and you certainly helped!

      I do love the dresses and if you have a suggestion for what might look cute on me please feel free to share!

      Love, Hannah


  9. I’m a sissy. I developed the love of sexy lacy panties and thigh highs, the submission and what is usually missed by people trying to figure a sissy mentality out is the uncontrollable need to be as slutty and open to hardcore sex where you will feel used. Kind of masochist. Definitely gender and sexuality are involved as someone stated above. It a feeling inside I had since I was 10. When I read about the sissy lifestyle the first time, and the cuckold lifestyle, I was absolutely enthralled because it described me perfectly.


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