Are you wondering how to become a sissy?
Well, this has been a highly requested blog post from many of my readers so I am very excited to finally get around to this.
And I’d also love to get some feedback and hopefully help some sissies on their journey!
Alright…so how do you become a sissy?
Well, the first step to becoming a sissy cuckold is your attitude.
You need to WANT it
You want to be feminized…You dream about it. The thought consumes you…
Assuming you meet that requirement, here are 10 different things you can start doing today to become a sissy!
Contents
1. Wear panties
One of the easiest ways to begin your sissy journey is to begin wearing panties.
First of all, panties are MUCH better than any men’s underwear. They are softer, tighter, and just more comfortable overall.
And the best part is, you can wear many different styles and colors.
For example, you can wear thongs, boy shorts, cheeky panties, and much more!
And you can wear awesome colors like pink, purple, red, and other colors that aren’t available with boxers/briefs.
Once you put on your first pair of women’s panties you’ll instantly feel like a sissy. It’s a hard sensation to describe, but when you try it you’ll know what I mean!
P.S. if you want a more in-depth guide to wearing sissy panties, check out this blog post.
And if you want to buy some sissy panties, check out this sissy panty store!
2. Lock it in chastity
Becoming a sissy means giving up your masculine qualities. And what better way to do that then give away your dick?
That’s why men who want to become sissies need to lock it up in chastity!
Locking it up will turn your manhood into a clit…eventually!
After all, if you keep your manhood locked in chastity for long periods of time it is *possible* to shrink it!
Not only that, but you can lock your dick up in some colorful resin cages like purple or hot pink!
And if you are a good sissy, you can match the color of your chastity cage with your panties – color coordination is hot!
Plus, once you are locked in chastity, you will be able to have “sissygasm” – basically cumming in the cage.
It’s like having a real clit! The sensation is incredible – especially if it is induced by your prostate.
Trust me, you don’t want to miss out on that sensation!
3. Eat cum like a slut!
Another way to become a sissy is to start eating cum.
If you don’t have any partners available to play with, start eating your own.
In fact, I personally think that is the easiest way to get your “supply”!
Yeah, you might be disgusted eating your own cum at first, but if you do it consistently, you will learn to love it!
Another tip is to start off with pre-cum. Pre-cum will have a watered down taste, so that will be easier to get your taste buds accustomed to your own cum.
Once you are able to eat your own cum consistently, you will truly become addicted!
And when you start finding partners to play with, you’ll be able to practice your cock sucking sissy skills!
4. Suck cock
One of the classic duties of a sissy is to suck cock!
Obviously you will need practice so buy a dildo for this – ideally a big black one!
Practice makes perfect, right? So, spend 10 or 15 minutes every day sucking cock like a pro.
Also, one thing that is fun to train is your gag reflex. After all, it really changes the blowjob experience!
If you have a Mistress, she can help guide you along this process. In fact, she may even help you suck cock with a strapon!
When you touch the real thing with your sissy lips, you’ll be ready to make the hot stud cum all over your mouth!
Also, be sure to practice putting on lipstick so you look real pretty like a sissy should!
Finally, remember that no one likes teeth with their blowjob!
5. Pee sitting down
One easy step to becoming a sissy is changing your bathroom habits.
And this starts with the toilet!
Sissies need to pee sitting down.
Not only is it more girly, but it’s more practical too! Now, you won’t have stray streams of piss going all over the place and creating a mess.
And the best way to learn how to pee sitting down?
Get locked in chastity!
When you are locked in chastity, it becomes a nightmare to pee standing up. You’ll get pee all over the place and cleaning up is a huge pain in the ass.
But when you are a sissy locked in chastity, peeing sitting down just becomes second nature!
You see, peeing while sitting on the toilet with chastity makes the entire process SO much easier! The pee just drips out of the pee-hole and there’s very little spillage at all!
All you have to do is clean the tip of the cage every time after you use the toilet.
Peeing sitting down has never been easier and more sissy fun!
6. Start wearing heels
Another way to become a sissy is to begin wearing heels.
Obviously, if this is something you haven’t done before it takes a little bit of adjustment.
As a result, I would recommend starting out with smaller heels (1 inch or less). This way you can get used to the feeling of being “taller” and balancing while you are walking.
Once you are more experienced, you can go with larger and higher heels!
Get a large mirror in your home and watch yourself strut like a sissy with your heels on. Record yourself walking and take notes on how to improve your posture!
So, what color heels should you start with?
Well, in my opinion, you can’t go wrong with black or pink!
Oh and stilettos are super hot for sissies! Wearing thin heels like that just screams “sissy boy”!
7. Makeup
If you want to be a sissy you need to wear makeup eventually!
This is one of the easier places to start because you can order a lot of what you need online.
Also, there are a lot of great YouTube tutorials on applying makeup!
You can get your lips done, put on some foundation, and even do your eyelashes!
Becoming a sissy is very exciting and I would have to say putting on makeup is a rite of passage for many sissies.
It’s also great if you have someone (like your Mistress) guide you through the process. It becomes a totally amazing bonding experience!
8. Get your nails done
Getting your nails done is a big part of being a sissy!
Now, if you want to save money, you don’t have to go to a salon and pay someone $50+ to do it. You can do it yourself!
Personally, I think you should go with a sissy color like pink for your first time, but the choice is up to you – purple and baby blue are also great colors in my opinion.
However, pink is just such a great sissy color and you can use it to match your chastity cage, panties, and heels!
Of course, if you can pay for a professional manicure/pedicure, you should definitely experience that! In fact, I think it’s a great bonding experience with your Mistress.
Go to the nail salon together like you’re just one of the girls 🙂
9. Start your wig collection
Wearing a wig is also a great starting point to becoming a good sissy.
The great thing is, a wig allows you to change your style completely! And you can make your clothes/heels match your wig!
You can get a lot of great wigs online. I would start with the major colors first: brunette, blonde, and red.
After you feel comfortable with those colors, you can also try more exotic colors like purple and pink!
Now, in terms of wig length, I would say something around should length hair is a good starting point, but again you should experiment around to see what fits your style and preference.
Over time, you will collect a bunch of sissy wigs so you will know which style you like the most!
10. Color coordinate outfits
Once you are a little bit more experienced with cross-dressing and becoming a sissy a more advanced feat is to coordinate your outfits.
What does this mean? It means matching as many colors as possible for your clothing.
For example, you could go all pink with your chastity cage, panties, skirt, nails, heels, etc.
Imagine being all dressed in pink (including your chastity cage! You’ll be the sluttiest sissy on the entire block!
How To Become A Sissy – Final Thoughts
Overall, becoming a sissy is hard work as it requires you to pick up new habits and skills.
However, it is totally worth it to live out your dreams!
Hopefully these tips help you on your sissy journey.
Readers, do you think I missed anything in this post? Let me know in the comments!
Julie says
Hormone treatment?
James says
I am not sure being a sissy is something you choose. Being a cuckold requires another party to cuckold you. That is a choice left to them. When you go into or accept chastity you have removed the constraints of the relationship from your partner. The simple click of the lock gives your partner the freedom to explore sexual alternatives. And by accepting chastity you have given the control to another.
pathetic_eric says
This is excellent! I do 8 out of the 10 suggested activities. I haven’t purchased a wig nor done make up. I also make sure my ass is plugged… and at nights – I wear a teddy to bed. Thankfully – I have a beautiful woman who supports me!
MyFemdomRules says
Great progress! That’s awesome!!
Louishka says
I do all except the “heels” part. tried so many times, but cant find my balance. Even though my mistress punished me and trained me for a while, but i cant do it. I guess my body type is not built for it.
15 years ago i started wearing tiny G-String panties and since then there is no return.
Perhaps add wearing “Butt Plug” to your list ??
I don’t agree with your final thought about it being hard work. When you have it in your system and when you are naturally into and not forcing yourself to be a sissy, then everything comes with the flow easily
Julie says
Is there any Sissies on Hormone Treatment? I’m thinking of it but need some advice from someone who as tried or is still on them x regards & xxx s Julie