So you want to be a sissy… (Part 3)

This is the final part of a 3-part series. If you haven’t read them:

Click here for part 1
Click here for part 2

You have the mindset of a sissy but you are lacking some critical pieces. These last pieces are crucial for you arising to the top of the sissy slut ranks and properly distinguishing you from a crossdresser. These items will show everyone who encounters your sissy self just how depraved and what a huge cock-hungry whore you really are.

Step Five: Accessorize

What you are missing are a butt plug and a chastity device.

Out of the two, you probably should start with a butt plug. It is the less costly of the two and is more suited for a debutante since you are going to have to become accustomed to having things stretch your ass.


The whole point of the butt plug is to stretch an anus. Anal sex, contrary to depictions in porn, can be very painful. Most people do not play with their asshole nearly enough to attain the asshole that bottom pornstars all seem to have. It will be painful, especially at the beginning. You are, after all, forcing a body part to open and contract in the opposite way it evolved to function. You may even see a bit of blood the first few times, and that is normal. What isn’t normal is a lot of blood, which may mean you have an anal tear and need to be hospitalized.

When exploring and engaging in anal play, be careful and remember the golden rule: You can never use too much lube.

If you are new or are a complete anal virgin, do not start with too big of a plug. You want something that will stretch your asshole and get it ready to have a nice hard cock slide right in, not accidentally rip you apart. I suggest getting a plug made out of silicone since they are easier to clean and you can find them in all kinds of pleasurable (and painful) textures to suit your tastes.

If you already have an impressive collection of various plugs, this would be a good time to buy a vibrating butt plug. What is great about a vibrating plug is that it combines the function of a normal plug with the pleasure of a vibrator. You will get the humiliation you crave and the pleasure you might deserve.

If you want the ultimate in vibrating plugs, check out WeVibe*. They have one (called Ditto) that uses an app and can be used by someone else remotely to mess around with you. Another pretty great feature they have is that you can have the vibrator sync up with music, allowing you to engage in some high-tech debauchery.

Whatever you end up buying for yourself, make sure you properly clean it before and after each use. You’ll want to make sure to use an antimicrobial soap to minimize your chances of getting an infection or some other ailment you’d do best to avoid.


You are not a man, merely male. You aren’t meant to live for your own pleasure. You are a sissy and you are here on this planet to please men. You aren’t even meant to have a normal orgasm.

How does a Master like myself ensure that you never ejaculate ever again?

We just lock you up in a chastity cage.

A chastity cage (sometimes referred to as a chastity device), is the male-equivalent to the infamous “chastity belts” of Medieval fiction. As opposed to the belt, chastity cages are worn exclusively by men. The purpose of a chastity cage is to prevent the wearer from achieving a full erection in a comfortable manner. Your soft clitty should fit pretty snugly in the device so be sure not to get a size that is too big for you. They are restrictive accessories and are not meant to be comfortable. In fact, the whole purpose of the device is to prolong the sexual torment and suffering of the wearer.

Men are cum factories. Our testicles are constantly producing cum and we need to ejaculate on a regular basis to maintain even a base level of sanity. The less often we cum, the more focused we become on cumming. Without a release, we become increasingly horny at even the most mundane of provocations (think Victorian gentlemen becoming aroused at the sight of ankles). After a long time of being turned on and not releasing, you will achieve “blue balls”. Once at this point, even taking a single step will feel like getting kicked in the balls. It is a very painful condition and it can be immediately treated by simply ejaculating.

A chastity device, when combined with a padlock, ensures that you will not cum. You can’t touch your little clitty (a sissy doesn’t have a penis, they have clitties) or play with it. The metal or plastic restricts your clitty from ever attaining an erection but you will still be hard and in pain. It forces you to focus on someone else’s pleasure because the alternative is to wallow in your own misery. Another good reason to focus on your Master/partner/random stranger is that the only way you can cum is by prostate stimulation (via sex toys or a hard fuck).

Much like how fasting can sharpen your mind, not cumming sharpens your libido and dulls your mind (because you will have difficulty focusing on anything but dick). It is not uncommon for sissies that are locked-up to dry-hump pillows as a feeble attempt to get a release due to this overwhelming desire to cum. You will begin to crave more cock than you thought was possible. You may even begin to leave your home all dolled up looking for a hookup at a public restroom since you might get to make cummies in your panties. You will become a dick-crazed slut, it is simply inevitable when locked up.

The single most crucial component for a chastity cage is its lock. You see, it is not enough for you to be wearing a device that prevents you from getting hard (and possibly lets your little clitty wither & shrink away). You need to be unable to escape this torment. You have to be made to endure it even through your vanilla life so that you may be constantly aware of who and what you really are. Once locked in, a proper sissy hands her key over to her Master. Only the Master may decide when and if the sissy should regain her sexual freedom.

It is very possible to find a chastity device for a relatively low price on something like Amazon. I suggest not buying anything cheap though. You are going to be wearing this device for prolonged periods of time. As such, you will want something that will be convenient to clean, that you won’t slip out of easily as well as being durable. As such, I recommend you purchase something from Locked In Lust*. They really have the best quality devices on the market and are sure not to disappoint in their inescapability.

If you’ve made it all the way to this point, you are a truly a sissy.

You now have all the information you will need to begin, complete or refine your transformation. If you are still in need of help beyond this point, you should consider finding a Dominant to submit to. They will ensure you grow and thrive as the slutty cock-whore you always knew you could be.

*I’m not affiliated with either WeVibe or Locked in Lust, they just make high-quality products that are well worth their price.

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


Enrichen your favorite Patriarch.

2 thoughts on “So you want to be a sissy… (Part 3)

  1. As most of us Sissies, I have been in doubt about my real self. Not being able to find a Sissy community, is easy to keep feeling lost and alone. Your article expressed so well how I feel and encourages me to keep realizing I’m in my real path, because at the beginning being true to myself wasn’t easy, but after reading the three parts, I realize I’m on the right way to be happy. I have no Dominant Man in my life right now, it kind scared me to say “yes” to them, being insecure about myself of not being able to please Him really freaks me out! But now I understand some points I have to work to be all Men expects from me. Thank you for writing this articles!! I really appreciate it! ^ ^

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