7 Steps to Make Your Husband Your Sissy

Depending on your husband, turning him into a sissy may range from easy to difficult. Some men may have a hidden desire to be a sissy or a natural lean towards being a submissive. Others may have a macho personality that you may be hoping to tame and may take a lot more work. 

The amount of work it takes doesn’t matter as there’s nothing more satisfying then seeing your husband progress into your sissy. Any amount of work and time will be well worth it when you have a well behaved, subservient husband and, if you so desire, cuckold.

So how do you convince your husband to become a sissy? Here are our 7 steps to make your husband your sissy.

1. Lock Him in a Chastity Cage

The first thing you need to do is to lock him up in a chastity cage if you haven’t already done so. Holding his chastity key will give you the power in the relationship as you will hold control of his penis and orgasms and he will have no choice but to obey. The longer he is locked up, the more willing he will be to do whatever you want. 

However, even with that power, you can’t make him take the jump from man to sissy that quickly. You will still need to progress over the following steps to complete the transition. The cage will make them all much easier though!

2. Wear Panties and Pantyhose

All men have either thought about wearing panties or have worn them before. Convince him to try on a pair one day after sex or when you’re putting laundry away. Start with a pair of briefs, maybe ones that have ruching in the back to really hug his butt. He will feel a little silly and a lot aroused. Dare him to keep wearing them. Make him wear them the next time you have sex, tell him that you know how much he was turned on by it and that it’s okay. Start buying him his own panties and slowly replace his old underwear with them.

Pantyhose will be a little trickier to get him to wear so you will need to be creative. I once dated a man who was an avid runner who was dealing with calf strains. I told him that wearing pantyhose will help apply pressure to his calves to help with his pain. Next thing I know, he keeps complaining about pain and was wearing my pantyhose every night!

3. Call Him Names

Is he being hesitant to wear panties or try something sissy-esque? Tell him, “What are you a sissy? Just try it!” (Enjoy the pun when you do). Or change his name to the girl version of his name (Kyle to Kylie, Jessie to Jessica, etc). 

You can also refer to his caged penis as your penis to make him understand that you’re in control and hold power over him. Eventually, you can even call it his sissy clit.

4. Paint His Nails

Have him join you to get your nails done one day. He will be surprised by how much he likes the leg massages, the massage chairs and the whole experience. Tell the manicurist to give him a clear coat of nail polish. He will be very hesitant at first but tell him that no one will notice and that it helps strengthen your nails (both true).

Once he’s used to his clear coat, convince him to let you paint his toe nails a nice girly color. No one will see his toe nails except for the two of you so why not? Eventually, paint his fingernails for a weekend and slowly expand the time.

5. Wear Bras

Like pantyhose, getting him to wear a bra may be harder to do. One way is by buying him bras (or bralettes may be easier) that match his panties and tell him if he wears the panties that he needs to wear the matching bra.

6. Anal Training

Any good sissy will have a very willing and easily penetrated anus. Back when I was dating, I would always start by sneaking a finger in his butthole while giving him a blow job. He may be discomforted at first but tell him he will like it if he relaxes and keep at it. In my experience, he will soon want you to go deeper and eventually you will be able to pull out some of your sex toys like smaller dildos or butt plugs to use on him. 

Over time, graduate him to wearing butt plugs in his every day life and increase the size of the plugs that he wears. In due time, he will be ready for your strap on and willing let you fuck him.

7. Practice Sucking

Much like his anal training, start by having him suck on your finger. Don’t reference penises or anything, just act like you like it when he sucks your finger. As you start using dildos and sex toys on him, make him first suck them if he wants them used on him. Just like his anal practice, he will graduate to sucking your strap on and eventually maybe even your bull.


Making your husband your sissy won’t happen overnight and may have a lot of resistance. Luckily for you, there are lots of ways to convince him to try these things that he will enjoy. The first of course is the power of the chastity key. Tell him if he tries wearing a bra that he will get unlocked for some fun, tell him if he wears a butt plug all day that you will let him orgasm, etc.

Another fun method that I use is to place bets on his favorite sports teams. If his team wins this game then he gets a reward, if they lose then he needs to wear a dress and clean the kitchen. Find fun ways to convince him to be your sissy and he will learn to love it. Maybe you will even be able to turn him into your sissy maid.

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