How to Make a Sissy

Training your Husband to be your Sissy

As I've attended kink events around both Australia and New Zealand I'm often amazed at how often a woman or women will come up to me and ask "How do I turn my guy/husband/partner into my sissy? I would like to play with other males but all he wants to do is watch me with other women."

I think it's probably because I usually have a collared and trained sissy or transgirl on a leash with me.

The sissies, especially, get a lot of interest from the woman because they are more obviously a male that has been feminised.

Now boys, before you all go racing out to buy a pair of frilly knickers, the women, usually, don't want to fuck sissybois. They just love the idea of owning a subjugated male whose sole job is to fluff their "bulls" and to then use their tongues to clean the bull's cum out of their pussies and ass and off their faces after they've been used like the sluts they secretly yearn to be.

So, ladies, this is how to do it. But beware because it more often leads to complications than not! And know that if you're going to do this you're committing yourself to at least 6 month project. But if your man is, as is described below, it's going to be more like a 2 -- 3 year project!

I have assumed here that you're not already in a D/s (Domination/submission) relationship with your man and that you haven't already 'played' with another woman (willingly or just because you wanted to keep your man with you and happy)

If you're already in a D/s relationship with you as the submissive partner, good luck breaking him out of that! He's already getting everything he desires and he won't give that up easily. It's not impossible though as it's widely held that virtually no one is 100% dominant or 100% submissive, we all have, to some degree, switch desires and capabilities within us.

I'm also using, as my start point, a 'worst case scenario' for you. Your man is 100% straight and has no interest in doing anything with another male. He has believed, until now, that he's the dominant partner and will resist being turned into the less powerful one and will absolutely resist any attempts to introduce another cock into your relationship. Your current sex life is probably plain old vanilla 'cock in vagina' fucking where he hardly considers your wants or needs at all. He thinks a quick tweak of your tits and rub of your puss means you're good to go.

There's a pretty good chance he's actually a whole lot more submissive and willing to be dominated than you would believe. As I've observed many times in the past. Submissive men are a lot like dog shit on a Parisian street. You can't help but stand on some every time you turn around! If he is most of these steps won't be needed. You'll be able to tell by how readily he accepts being locked into the cage and feminised and how soon he accepts you bringing another cock into your relationship. I'd still recommend starting with a transgirl or crossdresser, though, because he's much less likely to get freaked out! (After all the only difference between a straight man and a bisexual man in a 6 pack of beer, a hot tub and a reasonably attractive transgirl!) It's also that he'll be much more willing to let a pretty crossdresser or transgirl suck him off and to go down on her than a masculine man the first couple of times. Most men are sluts and, as long as they're getting their rocks off regularly, they don't care whom it's with!

1. Getting him started on his journey.

Buy your man a chastity device (cock cage). One that is lockable, make sure the key is well hidden. Then, on a Friday night, induce some sex play and, as you go down on him, say you want to try something a little kinky then lock him into the cage. Now tease him mercilessly. Kiss and stroke all of his erogenous zones. Neck, nipples, perineum, spine, backs of knees, etc. Create as heightened a sense of arousal in him as you possibly can. As soon as he is as turned on as you can possibly make him grab him forcibly by the hair, or back of the neck if he has none , look directly into his eyes and say firmly "I'm not going to let you out until you have satisfied me completely."

Then lie back. You must not allow him to go directly to your breasts or pussy. He will try to, trust me! He must start at your feet and massage/kiss/stroke his way up both legs, skirt around your whole pussy area, and do the same across your stomach, skip your breasts and work on both of your arms. You must then roll over and make him kiss the nape of your neck and trail kisses down your spine. Have him tongue the cleft of your ass, allow him to taste your taint and tongue your rose bud (if it's something you like having done, make him do it) then down the backs of your legs. Have him softly lick the backs of your knees.

Once he has completed the tour of your erogenous zones, and only after he has toured them all.

You must get him used to serving your needs primarily before considering his.

And no matter how turned on you are, you will then turn on to your back and guide him to your breasts. Show and tell him how to do it properly.

If you really want to know how having your breasts fondled and caressed properly feels like get another woman to do it!

Voice your approval as he learns how to caress, suck and fondle them the way you like. Once you are as close as you can get to orgasm without popping guide his head down to your pussy. Once again, you will need to show him what you want. Tell him what you want/need.

You're training him to obey your voice and service all of your wants and needs primarily.

Show your appreciation as loudly as you dare when he does it well. Guide and show him when it's not quite right (be careful to offer no criticism though).

As soon as you orgasm, or are satisfied, if you're multi-orgasmic, immediately roll over and go to sleep.

Pretend if you have to!

He will probably protest but pop an eye open, throw a hand over him and say something like "My God, baby, that was so good! You've completely worn me out. I'll take care of you in the morning, I promise."

1. Making him horny.

As soon as you wake, try to be as late as possible, get out of bed. Shower, get dressed, do your make up and go out for most of the day. He will probably follow you out hoping you will 'take care of him as promised' but look at your phone or watch or clock and go "Fuck! I'm late!" When he asks where you're going sigh and say something like "I really don't know why I bother telling you anything because you never remember! I'm meeting the girls (or your parents, or you've got a work thing) for brunch, remember?"

It doesn't matter that it's not true because he probably would have forgotten any way, right? 

Grab him by the cage, he will be excited and trying to go hard, but the cock cage will be preventing it, pull on it tightly enough to be slightly painful and say "You were so good last night, lover, I hope you can give me a repeat performance this afternoon?" Kiss him passionately, try to fan his arousal levels as high as you can with your kisses and touch whilst keeping hold of the cage.

You have to remember men are very cock centred in their arousal.

Press your breasts against his chest or arms, kiss him again, let go of the cage and walk out.

If he wants out of the cage give him a mischievous smile and say "No, you'll just have a wank as soon as I go, I know you! And I want at least as good a performance when I get back as I got last night!"

You must go out until at least mid-afternoon but send him regular, but irregularly spaced, texts telling him you're thinking about how good the sex was last night and how much of a stud he was and how you're hoping for another session at least as good when you get home.

1. Getting him to wear his cage all the time.

When you get home grab him by the hand and lead him straight to the bedroom. Drop your clothes to the floor just as quickly as you can, climb up on the bed, spread your legs, touch your pussy and say "Hurry up, baby, I need you right now!"

Make him strip naked, except for the cock cage, of course, before letting him up on the bed.

He'll probably want you to take off the cage. Say "Not till after you've done me first!" Give him a really big smile and pat the bed beside you.

This time allow him to go straight to your breasts, you're turned on, remember? You don't 'need' him to warm you up this time. He must start at your breasts, though, and you must make him go slowly and gently so that he is actually turning you on.

Remember, you are teaching him that your needs come first.

Make sure you are vocal in your appreciation of what he is doing, guide him, show him, not so much verbally, but by guiding with your hands and by moaning loudly when he gets it right. Once you are ready guide him down to your pussy and have him tongue you to another orgasm (or multiple orgasms) until you are satisfied.

Once you're done pull him up so his head is on the pillow with you, snuggle your naked body as close to him as you can to him, grab hold of the cock cage and gently play with it.

By now his balls will be aching and he will badly need to come.

Kiss him and praise his love making generously. Tell him how good he was and how good he made you feel.

Here comes the key part (because you need him to stay caged).

Pull a little more insistently on the cock cage and say something like "I think this has really helped. It seems to have made you much more enthusiastic and conscientious about looking after me first and not just looking after your own needs. If I promise to look after you too, will you leave it on for me?"

You must now wait! Men are like steam engines! They can't do anything without a whole lot of huffing and puffing. He will voice some protest but it's vital you remain quiet until he either agrees or goes silent. If he hasn't answered "yes", simply look him in the eyes as adoringly as you can, and say "Please?" He will still likely say no, but you must not relent. Just pout and say "Please, baby, I really like being like this with you."

If he still says no, don't insist, you'll just make him angry. Release him from the cage.

You'll probably have to let him fuck you to keep up your end of the bargain. But don't allow him to touch you sexually again until he agrees to be caged. Every time he asks or tries to initiate something just sigh and say something like "I don't think you care about my needs at all, only about your own."

Men really hate feeling like they've disappointed the woman they love.

Over the following days, at least a couple of times during every night, fondle him to hardness but when he turns to you and tries to initiate something shrug him off with an annoyed grunt as if he's woken you up.

After a few days he will, more than likely, put the cage on himself. If he doesn't ask him to put it on for you again. He'll huff and puff again, but you need to remain silent, if he doesn't acquiesce say "Won't you do this one little thing for me? It feels so good, for me, when you're in this and looking after me first." And look at him fetchingly. If he masturbates don't say anything just look disappointed.

Keep this up and he will fold and agree if for no other reason than that he knows he's not getting any until he has.

1. Once he has agreed to being caged voluntarily, and has gotten used to wearing it, you can move onto the next stage: Sissifying him.

You start by grabbing the cock cage and saying "All this pubic hair must make wearing this really uncomfortable. Let me shave it off for you!" Don't let him say no. Just drag him by the cock cage into the shower, turn the taps on, take off the cage, grab his razor, lather him up with some soap, and begin to shave the area. Make sure you are teasing and playing with him, take him in your mouth and say "It'll be easier if you're hard cos everything will be out of the way!"

Do not let him come!

Make sure his whole jockey brief area is well shaved. Remove all the hair from around his cock, balls, perineum and ass. Tell him, very vocally, how good it looks and how sexy you find it, that it's turning you on and that his cock looks so much bigger shaved like this!

Cock ego and envy is very central to a man's psyche.

The area will rash the first few times if you don't treat it properly. It's the itchiness and rash that stops most men from wanting to repeat the process. To prevent this, baby powder works well, so does baby oil. Put it on for him over the next few days, until it's time for him to shave the area again. Use it as another way to keep his arousal levels high.

As he is now as hard as a rock, and aching to come, you need to get rid of his erection before you can get the cage back on. So lead him back to the bed. If you're not already shaved around your pussy area bite your lower lip and look a little shy and ask "Will you shave me down there too, please?"

Keep in mind you are trying to teach him to obey your every whim and command.

Send him to get a towel (for under your bottom), a hand mirror (so you can see if he's got everything), his razor, some shaving foam, a facecloth and a bowl of warm water. Get him to shave you clean. Allow him, in fact, encourage him, to play with your clit and pussy and to slip his finger inside you. Luxuriate in the attention and let yourself get really turned on so he can feel the wetness and heat coming from your pussy.

Obviously if you're already shaved or waxed or lasered down there you can skip this part.

As soon as he's finished guide his tongue back onto your pussy. Tell him you want to see him masturbating as he eats your pussy but he's not to come until you tell him you're satiated. Once he has satisfied your needs say something like "I want you to kneel between my legs and masturbate until you come on my pussy. I want to feel your come hitting my labia and leaking down my pussy, being shaved like this, it will be so hot!"

It's very important that you don't allow him vaginal sex until he is ready to become your sissy cock slave.

Trust me, it won't take him long to come. Tell him how hot that was to watch and feel. Place your hand on the back of his head and see if he will let you guide him down to use his tongue to clean you up. If he doesn't resist or he seems willing but a little hesitant say "Use your tongue to clean me up, baby! That would be so hot!"

Do not insist though, he needs to think he is a willing participant in his sissification. If he doesn't want to lick you clean you still need to make him clean you up. Send him to get a wet warm washer.

Cleaning you, as well as your bull up, after sex will be one of the sissy's main tasks.

Don't let him take too long though or he'll be hard again and you'll have to repeat the process of getting rid of his erection. While he is still soft lock him back in the cage. Tell him how sexy it looks and how much you like how he has been 'looking after you' sexually and how much fun it's been and is going to be. Make sure he knows how much you like how his cock and balls look shaved and in the cage (so horny making) and how you expect him to keep the area clean shaven now. If you'd like to remain 'bare' down there make shaving you part of the weekly duties he has to perform to be allowed to get his reward.

If he presents unshaven refuse to even allow him to touch you until he's cleaned himself up.

It's very difficult to keep everything around the cage completely shaven so make it a weekly event that you release him from the cage, have him shave it all properly (and you if that's required), show you how good a job he's done (that he's been a good boy) and then masturbate onto your pussy or stomach or breasts.

Never onto your face, no matter how much you like it! And never let him come on your ass because you want him to get used to showing you what he's doing.

There will be things that he will never be allowed to do, like coming on your face or fucking you in the ass, because they are reserved for your bulls. He needs to eventually learn that the reason you have to take a bull is because he in inadequate for your needs.

Then he goes straight back into the cage.

1. Keeping him in a constant state of frustrated arousal.

This once a week masturbation is the only relief you will allow him. Make sure you tease and play with him every chance you get so he's in a constant state of frustrated arousal. Keep telling him that you will 'look after him, too'. But that having him so attentive makes you so horny and feels so good that you want him to stay that way a little longer. Say "Think about how good it's going to be, for both of us, when I finally let you fuck me!"

It's also vitally important, for now, that you don't 'make him come', not with your hand or mouth or pussy or ass. His role is to satisfy you, then, if he's been a really good boy and satiated you completely, you will allow him to get himself off.

Every so often you will need to pretend he hasn't done a very good job at getting you off (even if he has). That you're not 'properly satisfied' and make him watch as you pleasure yourself to a very loud orgasm (pretend if you have to). Then refuse to let him come on you as he masturbates because he hasn't satisfied his end of the bargain. Make him come on his own stomach. Gather some of his come on your fingers and see if he will lick it off for you, wipe it on his nipples, if he won't.

After he has come, spread your legs, touch your pussy and ask if he'd like to try again to get the chance to come on your breasts? If he will help and guide him so that you can have a really good orgasm and reward him appropriately. If he refuses don't let him anywhere near you until the next week.

He will, of course, be trying to insist on actually fucking you (putting his dick in your vagina). In turn try to insist that he doesn't because "I want to keep exploring what we're doing together because I don't think either of us have had so much fun or come as hard as we have these last few weeks!"

You may need, from time to time, to break the 'no penetrative sex' rule to keep him from rebelling and refusing to play anymore games.

1. Starting his feminisation.

After a few weeks of this, and on a day just after he's shaved and is about to masturbate, throw him a pair of your knickers, or a pair you've bought specially for him if he is too much bigger than you to wear yours, and say "Put these on for me, lover? I think they will look so sexy that I will probably get really horny, and you know what happens then!" and smile.

It works especially well if it's a pair you've worn and been aroused in, ask him to sniff them first and then put them on.

He will most likely protest "I'm not a pooftah", he'll say. Reply "I know you're not, silly!" Touch your pussy or cup your breasts. "You've shown me that very well lately! I just think it will look as sexy as hell!"

As before you now need to remain silent. If he refuses shrug and tell him to put the cage back on. Say "I don't know what your problem is. It's going to make me horny and you're going to get to come, so why won't you put them on for me?"

Refuse to let him even masturbate, let alone, come on you, if he won't put them on.

Use the same process as before. He'll cave even quicker than the previous time.

Always make him lock himself back into the cage so he knows he's doing it voluntarily.