You may have read my story, ‘Expanding your wife’s Horizons’. This is the companion to that storty. It is a detailed set of instructions on how to convert your man to a sissy.

Training your Husband to be your Sissy

Explanations: 1. Italics indicate an explanation for why I want you to do the above.

2. Bold print denotes either chapter titles or advice.

As I’ve attended kink events around Australia and New Zealand, I’m amazed at how often women come up to me and ask, “How do I turn my guy/husband/partner into my sissy? I want 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 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 a six-month project. But if your man is, as is described below, it’s going to be more like a two to three 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 starting 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 that he will absolutely resist any attempts to introduce another cock into your relationship. I’ve assumed that your current sex life is probably plain old vanilla ‘cock in vagina’ fucking where he hardly considers your wants or needs. 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 is a 6-pack of beer, a hot tub and a reasonably attractive transgirl! He’ll also be much more willing to let a pretty crossdresser or transgirl suck him off and 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!

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 turned on as possible, grab him forcibly by the hair or back of the neck if he has none.

Then, 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, massage/kiss/stroke his way up both legs, skirting around your pussy area. Then, do the same across your stomach, skipping your breasts and working 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. Next, have him tongue the cleft of your ass, allow him to taste your taint and tongue your rosebud (if it’s something you like having done, make him do it), then down the backs of your legs. Finally, 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 turn on your back and guide him to your breasts. Then, show and tell him how to do it properly.

If you really want to know how having your breasts fondled and caressed properly feels, 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.”

Making him horny.

Try to wake up as late as possible. Then, 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, watch, or clock and say, “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 anyway, right?

Grab him by the cage, he will be excited and trying to go hard, but the cock cage will prevent 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, and try to fan his arousal levels as high as you can with your kisses and touch whilst keeping hold of the cage.

You must remember that 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 that you’re hoping for another session at least as good when you get home.

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 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 huge 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, and you must make him go slowly and gently so that he is turning you on.

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

Ensure you are vocal in your appreciation of what he is doing. Guide him, and show him, not so much verbally, but by guiding with your hands and 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, grab hold of the cock cage and gently play with it.

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

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

Here comes the critical 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 imperative you remain quiet until he either agrees or goes silent.

If he hasn’t answered “Yes”, 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. Instead, 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.

Until he’s caged, every time he asks or tries to initiate something, just sigh and say, “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 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.

Once he has agreed to be 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 soap, and 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 cum!

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 are very central to a man’s psyche.

The area will rash the first few times if you don’t treat it correctly. The itchiness and rash stop 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 cum, you need to get rid of his erection before getting 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, look a little shy, and ask, “Will you shave me down there, too, please?”

Remember that 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, 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, 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 cum until you tell him you’re satiated.

Once he has satisfied your needs, say, “I want you to kneel between my legs and masturbate until you cum on my pussy. I want to feel your cum hitting my clitoris and leaking down my pussy. Being shaved like this, it will be so hot!”

It’s essential 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 cum. 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 resists or 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 and your bull up after sex will be one of the sissy’s main tasks.

Don’t let him take too long, or he’ll be hard again, and you’ll have to repeat the process of getting rid of his erection. Then, while he is still soft, lock him back in the cage. Tell him how sexy it looks, how much you like how he has been ‘looking after you’ sexually, and how much fun it’s been and will be.

Make sure he knows you love 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 tough to keep everything around the cage wholly shaven. So make it a weekly event that you release him from the cage, and have him shave it all correctly (and you if that’s required). Then he has to show you how good a job he’s done (that he’s been a good boy) and masturbate onto your pussy, stomach, or breasts.

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

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

Then he goes straight back into the cage.

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 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 that you don’t ‘make him cum’, not with your hand, mouth, 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 getting you off (even if he has). That you’re not ‘properly satisfied’ and make him watch as you pleasure yourself to a thunderous orgasm (pretend if you have to). Then refuse to let him cum on you as he masturbates because he hasn’t satisfied his end of the bargain. Make him cum on his own stomach. Gather some of his cum 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 cum, spread your legs, touch your pussy and ask if he’d like to try again to get the chance to cum on your breasts? If he will, help and guide him so you can have a good orgasm, then reward him appropriately. If he refuses, don’t let him anywhere near you until the following 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 has had so much fun or cum 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 any more games.

Starting his feminisation.

After a few weeks of this, on a day just after he’s shaved and is about to masturbate, throw him a pair of your knickers. If you’re too small for him to wear your lingerie, buy a pair, especially for him.

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 exceptionally 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.

Then say, “I don’t know what your problem is. It’s going to make me horny, and you’ll get to cum, so why won’t you put them on for me?”

If he won’t put them on, refuse to even let him masturbate, let alone cum on you.

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.

Once he has them on you, you need to exclaim over them. Grab his ass and tell him how hot they make his ass look. Caress all over them. Push your finger up towards his rosebud through the material. Then, pull them out of the crack of his ass and slip your fingers inside the leg opening and caress his ass and entrance to his anus.

Mouth his caged cock through the material. Tell him how hot it’s making you and that you need him to make you cum again. Guide him into a 69 and, as he services you with his mouth, play with his knicker-covered ass. Slide your hands inside and caress his ass and his caged cock. Work a finger toward his anus, touch and stroke the entrance to his anus.

If he protests, go, “Shhh! It’s turning me on, can’t you feel it?” and keep going.

Let him bring you really close to orgasm, then push him off, pull his panties down far enough to take the cock cage off and immediately lie on your back with him between your legs.

Say, “Fuck, this is so hot! I want you to masturbate yourself over the top of the waistband of your knickers whilst I make myself cum. I need to feel your cum splash on my pussy as I pop! Can you cum with me? Cum on my pussy as I orgasm?”

He will, of course, be keen to cum.

Once he’s shot his load, take him by the back of the head and guide his head down to clean you up again.

If he still resists, say, “I think watching and feeling you clean me up will make me cum again. Please, baby, make me cum again? You make me so horny! I need to pop again, please, baby?”

If he does it, you need to cum! So fake it if you have to! Then tell him repeatedly how fucking hot it was, how good it felt and how you hope he’ll do it again.

If he still doesn’t want to use his tongue to clean you, you mustn’t make a big deal of it. Just keep trying every couple of times and tell him how hot the thought of him doing that makes you until he does.

Don’t forget to hand him his cage, so he remembers to put it on.

Starting to teach him his role.

Make this part of your weekly routine but remember, it’s vitally important that it’s not you that makes him cum. He needs to learn that having you give him an orgasm will only be allowed when he’s been a very good boy.

When he gets used to wearing the knickers as part of your weekly play sessions, on a day when he is out, remove all of his boy underwear and replace them with a selection of women’s knickers. Have some frilly ones, some thongs, some boy-cut briefs he can wear for work and any others you think will suit him.

When he complains, simply say, “Your ass is so sexy in your knickers. Please wear them all the time. It’ll make me so horny at work knowing you’re wearing some sexy knickers I chose for you. I’ll probably need you to fuck me as soon as you get home! Please, baby? It will make me happy!”

Silence now is again your best friend.

If he tries to refuse, say, “What’s the big deal? Only you and I will know. It looks sexy, and it turns me on. Don’t you like turning me on?”

If you quietly but stubbornly insist, using the same techniques as before, he will soon give in and agree to wear them.

Every time he ‘gives in’, you need to thank him and reward him for consenting to your needs. For example, let him have an extra orgasm or make him a lovely meal.

Training him to like ass-play.

Now is the time to introduce more and more ass play when he’s servicing your needs. Play with his butt, and slide your fingers into the crevice of his butt. Get him used to you stroking and playing with his taint. Keep sliding your finger toward his anus until he allows you to touch and play with his rosebud. Wet your finger and use it to rim his anus. Slip a little bit of your finger in.

Every time he protests, tell him, “Shhh, it’s turning me and you on. I can tell by how your cock throbs every time I do it.”

But remove your finger for a bit before returning to it again. Start to play with his balls as he masturbates for you. Stroke his taint as you handle his balls. Wet your finger, reach his rosebud, and make the area as moist as possible. Slowly get your man used to having your fingers around his taint and anus and a finger probed a little into his butt.

Obviously, you will need to sit up to do this. Let him rub his cock on your breasts if he’s letting you play with his taint and/or ass, but lean away, so he can’t if he resists your probing fingers. Push him away if he tries to follow you with a curt “No”. Reward him with contact with your breasts once he lets you start playing with his ass again.

Once he allows you to slip a little bit of your finger inside his ass as he masturbates, tell him how horny doing that is making you. Add how slutty it makes you feel and how much you love doing that for him. He will eventually relax and enjoy the sensation.

Once you can tell he is enjoying having his ass fingered (it might take a few sessions), wait until he reaches that point of no return and starts to cum. Then push your finger into his ass as far as you can and hook your finger back towards his balls. Hopefully, your finger will scrape across his prostate. If it does, trust me, he’ll want you to do it repeatedly.

Push the mounds of your breasts firmly around his cock and let him cum on them.

Cum if you can, pretend if you can’t, and say, “Fuck! I came just from doing that! Fuck, doing that is so hot! You have to let me do that again! Oh, baby, I came so hard!”

As usual, make him use his tongue to clean you up but guide his head between your legs again because he’s made you so horny. Again, pretend if you have to. He needs to know that what you’re doing to him, you’re doing not only for him but because it turns you on. Trust me, he loves making you horny enough to cum.

Getting him to do what you want is simply rewarding him when he obeys and ignoring him when he won’t but continuing to fan his sexual arousal.

How to enjoy anal sex.

If you want to try anal or have already experienced it, but it hurt, now is the time to teach him how to service your ass. First, lift your hips up and throw your legs over his shoulders. Then, guide his head lower until his tongue is licking your taint.

Don’t do this unless you are scrupulously clean in that area and around your ‘starfish’!

Use verbal encouragement and constant pressure on his head to encourage him to keep licking there and/or to go further towards your rosebud. Tell him how good it feels and how hot it’s making you.

Remember. Eventually, you’ll want to get him to the stage where he willingly does this for your bulls (prepares your ass to take their dicks).

Make him tongue your ass and lick your taint and rosebud. Roll over onto your stomach and put a pillow under your hips, so your ass is raised. Then he’ll be able to tongue you from your clit, across your vulva and perineum, and all the way to your rosebud. Every time his tongue hits your rosebud, groan in appreciation.

He’ll soon get the hint to concentrate on there. Instruct him to hold your ass cheeks apart, tongue your rosebud, and push his tongue as far into your ass as he can. Encourage him to ‘fuck you in the ass with his tongue’, shoving his tongue as deep as he can, withdrawing it, then repeating. You need to be very verbal about how good it feels. Next, reach between your legs and start to masturbate. Make sure you show by your moans and thrusting hips how much you love what he’s doing.

At this time, he is going to try and fuck you, probably in the ass, but definitely somewhere (he’ll ask you to take the cage off so he can). It’s imperative you don’t let him! No matter how turned on and horny you are, you must resist! Fucking you in the ass is going to be something he never gets to do. It will be reserved for your bulls. His job will be to ensure your ass is ready to receive the 9-inch monster you’re hoping to score with.

Tell him you’re too scared to let him fuck your ass because every time you’ve tried it, it hurts, but that you want to lie on your stomach and finger yourself to orgasm as he rubs his cock along the crack of your ass between the cheeks. Remove the cage and have him tongue your whole crack until it’s sopping wet with saliva, then have him lie on you with his cock between your cheeks and let him hump you. Every time he tries to slip it into your ass or pussy, and he will try, tell him “No” curtly and that you’re going to make him get off and put the cage on if he continues to try.

Tell him you want to feel him cum on your ass as you orgasm (to help him, regularly squeeze your ass cheeks together around his cock), so he needs to wait until he feels and hears you starting to cum. Once you’ve cum, and he’s shot his load, make sure you have him clean you up, but now, as he has been a very good boy, you need to reward him. I’ll leave that up to you. You can let him fuck you or give him a blow job. You choose. Definitely one of those two, though. But, as soon as he cums and cleans you up, he returns to the cage.