So you want to be a sissy… (Part 1)

You are a weak boy. You once dreamt of achieving male Alpha status so you could get the attention you crave but have fallen significantly short. You no longer dream of turning the heads of the women you pass on the street: you now dream of being made into a sissy.

You know you can’t compete with most men, so you want to try something different.

You want to feel sexy and feminine. You want a smooth, sultry, and soft body. You want to wear lingerie and women’s clothes. You want to wear makeup and be a man’s bitch. You want to suck as many cocks and please as many men as you can. The problem is, you don’t know where to start. Luckily, I can help.

STEP ONE: Start small.

You are currently fantasizing about being feminized but you’ve never even experimented. How can you know you truly want that? The most common shared female fantasy is to be raped, yet no woman has ever truly wanted to be raped (to be truly raped means sex without your consent so it is impossible to consent to rape).

The simplest way to start is by trying on your girlfriend’s/sister’s/cousin’s/mother’s panties or bra. While highly unethical (and kinda gross in my opinion), it is how most sissies and crossdressers get started.

I do not condone this but I understand most sissies aren’t exactly brave enough to go buy their own lingerie at the store. I also understand a lot of sissies that do this aren’t necessarily attracted to that person, just the lingerie itself.

Another easy way to get started is by buying your lingerie from Amazon. This is the best way to start since you aren’t being a thief or a creep. You also will need to buy your own stuff somewhere down the line so shortcutting here saves some time.

Once you’ve tried it on, you should know if being a sissy is for you. If it is, proceed to step two.

STEP TWO: Mind & Identity.

Now that you’ve confirmed your suspicions, you can begin your transformation. Let’s start with your mind.

You probably already think a lot about cock. You think about having them fill your mouth, jerking them off, and having them stretch your boi pussy. That is a good start, though it is not sufficient.

Cock needs to fill your mind. You need to dream about getting fucked. When your mind begins to wander, it should go to dick. If you’re thirsty, you should want to satiate your thirst with cum.

Your role as a sissy is to please men as best as you can. Sissies are mindless automatons of sorts. Whilst crossdressers retain their free will and individuality, sissies give theirs up. You no longer are to think of your own pleasure for it comes in distant second to all men. The only time when your pleasure should be taken into consideration is of your Dominant allows you to release your cummies (men cum, sissies make cummies). If you orgasm, it should be from having your prostate massaged and pounded by dick.

If your Dominant wants you to eat their ass, you eat their ass. If they want you to suck a cock, a cock you shall suck. If a Dominant wants to leave you tied up in a sauna, expect a sore ass in the morning. (These limits should, of course, be discussed much before they happen)

Another important factor for sissies is a feminine mindset. To be the best sissy you can be, you have to adopt and nurture a feminine persona, especially when it comes time to dress up. You may well work in construction but when it’s time to be a sissy you must abandon all masculine pretense, if only for a session.

Many sissies do this by creating and naming an identity that suits them. A good question to ask when going through this phase is “what is my sissy style?”. Are you a pretty princess? Are you preppy? A diaper brat? An emo gurl? Do you want to wear beautiful dresses? Are you a naughty secretary? Do you just want to be in lingerie?

Once you have that question answered, you’ll have an idea of where to look for inspiration for your particular identity.

Click here for part 2.

Have questions? Comment below or hit me up on Twitter/Instagram!


Enrichen your favorite Patriarch.

6 thoughts on “So you want to be a sissy… (Part 1)

  1. Yes, I want to be a gurl. I also want to have a partner who wants me as a gurl. I want to be the best woman I can possibly be for him/her. If only I could please him/her for the rest of my life, wear dresses and other pretty things and be everything they want from a gurl like me! Oh, pleae let me! Roxanne Lanyon

  2. I love spending most of my life as Joanne, along with being with men. I never new a girl could love the taste of cum as much as I do. I don’t know why I ever wasted my time with women

  3. One day I just know (and hope!) I will be asked to be his wife! Then you will never see a gurl as excited as I will be! Oh, when, when will it happen? email me at

    Your Miss Roxanne Lanyon

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