How to Make a Sissy

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You may have read my story, ‘Expanding your wife’s Horizons’. This is the companion to that story. 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!

 

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 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.”

 

2. 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.

 

3. 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.

 

4. 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.

 

5. 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.

 

6. 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.

 

7. 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.

 

8. 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.

 

 

9. 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.

 

He’ll be even keener to please you now as he knows when he does, he will get his prize of actually fucking you or being blown.

 

10. Teaching him more of his role.

 

He now needs to get used to preparing your ass to receive your bull’s cock. Ask him to buy you a series of butt plugs ranging from really small to as big as you think you might like to take.

 

Say to him, “I want you to be able to fuck me in the ass.”

 

Be crude in this situation because he loves to think you’re a ‘dirty’ girl

 

“But you’re too big. Will you help stretch me?”

 

Hand him some lube, your vibrator and the smallest of the plugs. Then lie on your stomach, spread your legs, slide your hands down to your pussy, and start playing with yourself. First, ask him to tongue your clit and vulva and make your taint and ass wet and slippery. Next, ask him for the butt plug and to watch for a moment. Lasciviously suck it and make it as wet as you can (he’ll love the show), then hand it back to him and tell him to be gentle. Have him rub it around your rosebud and gently apply pressure to the entrance.

 

Your ‘starfish’ will dry fairly quickly, so keep getting him to tongue the area when it does. Tell him to lube up the plug as well. When you’re ready, tell him to gently push the plug into your ass.

 

He needs to be in his cage for this because, if he isn’t, he’s going to try and substitute his dick for the plug, and if you’re as turned on as you should be by now, you’ll probably let him!

 

As the plug slides into your ass, it will probably hurt some (even when you’re stretched and used to taking cocks up there, as the head pops through your knot, there is usually a stab of pain). Ask him to stop and clench down on the plug with your ass sphincter.

 

Similar to those Kegel exercises you were meant to do after having your children remember?

 

Then relax your sphincter and give a gentle push, as if you’re trying to push the plug out, then relax and tell him to continue (repeat as necessary). Once it has popped through the knot (it will feel similar to when a man’s cock head pops through), the part of the plug after the widest bit is quite narrow and will sit inside you comfortably. Give yourself time to get used to being ‘filled up’ while continuing to play with your pussy and clit. Use your imagination, if you have to, and pick someone you’d really like to have in your ass and fantasise it’s him.

 

Once the plug feels comfortable, get him to tongue the cleft of your ass and gently pull back and push in on the plug. Make sure it doesn’t slip past the knot until you are used to that feeling (clench down on it with your sphincter if it feels like it’s going to).

 

You’ll probably come to love that sudden intense feeling as the plug, or your bull’s cock, pops through the knot but not immediately.

 

Tell him to increase his push and pull speed as your excitement rises. Ask him to use the vibrator on your clit and pussy as you get close. Use your fingers to guide him because he probably won’t know what he’s doing. As you get to almost ‘that’ point, tell him to turn the vibrator up, push it firmly against the plug, and slide a couple of fingers as deep into your pussy as he can. Continue to play with your clit as you ride the intense feelings as the plug vibrates through the thin wall between your ass and pussy.

 

Once you’re satiated, he needs to be rewarded again. Use whatever method seems appropriate (except for your ass, of course). Be extravagant with your praise. Tell him how good he is to you and that you love how well he has looked after you since he put the cage on.

 

Always make him think it was his idea to be caged.

 

Emphasise what a fantastic lover he is, how much you love him, and how you feel so much closer to him now that he takes care of you first and so well!

 

Hand him his cage.

 

Repeat with the other plugs until you can comfortably take one the size of the cock you think you might like to take up there.

 

11. Continuing his feminisation.

 

As soon as you feel that your man is no longer even really thinking about wearing women’s knickers, except when you’re grabbing his ass and exclaiming how hot he looks, you can add some ‘stay up’ stockings and a butt plug (for him) into the mix.

 

After he has finished in the shower and shaven his genital area clean, hand him a brief thong and a pair of stay-up stockings.

 

Don’t make any fuss about it. Simply say, “Can you wear these for me, please, baby?”

 

He will obviously protest. You should reply, “You have really sexy legs, and they will look even hotter in a pair of stockings!”

 

He’ll want to know why you want him in ‘this shit’.

 

Just say, “Because you’ve been so good to me, I’ve been considering raising the kink level so you can start to have some of your fantasies fulfilled! But I don’t think I can do it. I’m too nervous. So I thought we could play some role-play sex games where we ‘switch roles’.

 

I want you to pretend to be a ‘woman’ so I can see if I can make love to you like that and get more comfortable with these games we’ve been playing together. If it goes well, I’d like to see about finding a female lover for us both to play with. Please help me?”

 

How can he refuse?

 

Help him put the stockings on because he’ll try to put them on like a pair of socks (he won’t roll them up first), so you’ll have to show him.

 

As soon as they are both on, burst out laughing and say, “They look ridiculous with your hairy legs! Come into the shower, and I’ll shave your legs for you.”

 

Start walking towards the shower as if it’s a given that he will follow you.

 

He’ll raise the usual protests “what if the guys at work, or my mates, see it?” Point out that he works in an office (if he does) and wears long trousers all day, so who is going to see? If he works in shorts, point out that manscaping is a huge thing now, and you thought it would be a thrill if he ‘gave it a go’ because you think he will look hot!

 

Then say that after he’s done it, he can tell everyone at work that you fucked him senseless all afternoon and night (because you’re going to), and they will all consider doing it too!

 

If he continues to object, fold your arms under your breasts and give a really disappointed sigh, “Why do you keep resisting me when every time we do something together like this, our sex life gets better, and I learn to love you a little more?”

 

Retake his hand and insist he follows you to the shower.

 

Shave his legs smooth. Keep exclaiming how sexy his legs feel and look now they’re smoother.

 

Once you’ve finished, lean back and say something like, “Fuck you have sexy legs. I can’t wait to see you in the stockings!”

 

At this point, ask if he wants you to go ahead and shave the rest of him because “in for a penny, in for a pound, right?”

 

Hopefully, he will acquiesce, but it doesn’t matter if he doesn’t because you’ll get him there eventually.

 

Take him back to the bedroom, insist on rubbing some moisturiser into his legs and tease him mercilessly. Stroke his dick, play with his balls, finger his ass and constantly croon about how fucking sexy his legs are and how you can’t keep your hands off them. Rub some into his stomach, chest and back if he’s let you shave him all over.

 

The object is to bring him as close as possible to orgasm but not let him over the edge. This is called edging. You’ll need him to do it for long periods, as seen in the following passages.

 

Help him back into the stockings. On the pretence of ‘helping him’ stroke his now smooth legs, keep telling him how much his ‘sexy legs’ are turning you on. Let him feel your pussy so he can feel your arousal. Hand him the thong you’ve chosen for him (the thong needs to be big enough to cover his bulge).

 

You’ll want him in his cock cage, and given you’ve just spent 30 minutes winding him up, he’s going to be as hard as algebra, so tell him you’re just so horny you have to cum now. Say you want him to cum on your tits as you finger yourself to orgasm right now!

 

This is a time to fake it again if you can’t quite get there. You want him cumming as soon as possible and soft enough to fit back into his cage.

 

 

12. More feminisation.

 

Once he has finished and has you clean again, say, “I want you to look as much like a girl as possible. Then I can pretend that I’m making out with another woman. The cage will help smooth the bump (it will, but only because it won’t let him get hard), so I want you to put it back on.

 

Have him climb up on the bed and lie on his back, get him to raise his hands above his head and hold onto the headboard if you’ve got one or the back of the mattress if you don’t. Instruct him that the session is over if he lets go and touches you. Tell him he is to close his eyes and keep them closed.

 

This is, once again, getting him used to obeying you and only wanting to satisfy you, not just getting himself off. And helps move him towards taking the more subservient role you have in mind for him.

 

Now make love to him like you would like to have someone make love to you. Kiss the nape of his neck, blow gently into his ear, and nibble on his lobes. Kiss him gently, then passionately, softly lick the corner of his mouth, trail kisses down the centre of his chest and slowly circle into his nipples. Tease and nip and gently pull them with your teeth. Swirl your tongue around them and softly suck on them.

 

Around now, you will need to remind him he must stay still, keep his eyes closed, and not touch you no matter what!

 

The next thing is to start to talk to him like he is a woman. Tell him how sexy ‘she’ is. How you love her tiny tits and rock-hard nipples. Kiss slowly down his stomach, stroking and gently tweaking his nipples as you go. Trail kisses down to his thong, then kiss where a woman’s pussy would be. Use your tongue to lap at the area as if you were licking a pussy through her knickers.

 

Make sure you use the feminine pronouns whilst talking to him in these situations, as you want him to get to the point where he knows his role is to service cocks, not use his.

 

Tell ‘her’ you can feel how hard her clit is, how wet she is, and how you can feel the heat of her arousal.

 

Move him towards the centre of the bed so you can get into a 69 position.

 

Remind him again that he must keep his hands off you but can lower them if they’re uncomfortable.

 

Lower your pussy onto his mouth and ask ‘her’ to eat you out.

 

Explain to him he needs to pretend he’s a woman and be gentler with his lovemaking like a woman would be.

 

Sit on his face so he can’t see what you’re doing, and reach into your night stand and bring out the massage oil and the smallest of your butt plugs. Lean forward into a classic 69 position, slide the thong strap out of his crack, apply a generous amount of oil to his ass, and gently rub it into his rosebud. Start with your finger, as usual, and slip it into his ass. Mouth his cage through the thong and tell him you’re giving her a fingering while eating her ‘pussy’. Stretch his entrance until you can fit a second finger into him. Then, slowly insert the butt plug.

 

He’ll probably clench down and resist. Tell him to relax and enjoy, as there’s nothing like having your clit licked whilst there is a vibrator inside your pussy. Once the plug is fully inserted, hopefully, deep enough to be resting against his prostate, grab your vibrator and apply it to the base of the plug.

 

Doing this will send extremely pleasurable sensations across his prostate and colon, through the thin wall that separates his prostate from the base of his penis, and into his dick.

 

If you’ve done it right, there's a good chance he’ll cum, even though he is still soft in his cage. This is the start of training him to the point that the only way he can cum is with a cock, preferably the cock of one of your bulls, in his ass and rubbing across his prostate.

 

Make him pleasure you until you are satiated. Let him take off his cage and remove the butt plug, then reward him for being a ‘really good boy’ by letting him have vaginal sex with you. It won’t take him long to cum, properly this time. Make sure he uses his tongue to clean you up.

 

Remember that you’re going to make him clean your cum filled pussy after your bull has had you, so get him used to it now.

 

Once you’re clean, cuddle up with him and raise the fact that even though he tried really hard and you tried your best to imagine him as a woman, it didn’t really work. He’s just too masculine, dressed only in panties and stockings. Wonder, out loud, if he would be prepared to go a few steps further to ‘pretty’ himself up so it would be more convincing? If he doesn’t immediately say “yes”, drop the subject. Make sure he is back in his cock cage and let him sleep.

 

About here, you need to assess where your man is up to in his conversion from ‘Alpha male’ to ‘subservient cocksucker’. You have him, at this point, exactly where you want him to be when your bull arrives. Basically naked, with nothing on but a tiny thong, completely shaved down from head to toe, and in a cock cage!

 

So let’s look at some possibilities

 

He’s raised little to no objections to this point. This would mean he’s quite submissive, and you can start accelerating his transition.

 

He has willingly, or even better yet, enthusiastically gone along with all of the ‘games’ so far. Then you have a natural submissive. It will be pretty easy to convert him into a ‘cocksucking submissive’ as he, pretty much, already lives only to please you.

If your man is in the first category, you can mix and match some of the below to get him more quickly to part 25, where he meets Abby. In this scenario (what you do is slightly different to the suggested actions below), you should ask him to dress in his thong, etc., before ‘she’ arrives but raise no objection if he doesn’t want to.

 

If he is in the second category, you can skip down to part (25l) where Abby comes over the second time.

 

Remember, we’re not trying to create a transgirl here (not sure if that’s even possible). Instead, we’re trying to make a cross, or more accurately, fetish dresser (n. One who dresses in the undergarments customarily associated with the opposite sex to them for the purposes of sexual gratification).

 

 

There is a third category, of course, in which he resists you every step of the way. This means you will have to ‘break him’ into the role. The following instructs you on how to go about breaking him down. It mainly involves stripping away his male persona and force-feminising him completely. Later, he will appreciate that you’ve allowed him to return to some semblance of masculinity.

 

13. More and more feminisation.

 

The next morning fuss over him and tell him how sexy he looks in his stockings and thong with his shaved legs. Rub your hands up and down his legs, cooing over how smooth and wonderful they feel and look. Cup his cage as if you were cupping a woman’s vagina and finger the entrance to his ass. Emphasise how womanly he looks from the waist down and how you wish he had a pussy so you could go down on it because you think you would be able to do it this morning as you’re so horny.

 

Kneel down and mouth his cage to show you think you could.

 

Make him pleasure you with his hands and tongue. Explain that your eyes are closed because you imagine he is a woman servicing your pussy. Cum hard and loud, even if you have to fake it. Get him into a ‘scissor’ position where your pussy is grinding against where his ‘pussy’ would be.

 

Remember that you’re actually grinding against his cock cage. His balls are somewhat vulnerable inside the cage, so you must be careful! Crushed balls is not a pleasurable feeling! You will want to push hard enough so that it occasionally causes him some discomfort but not too much pain. Just to remind him who’s in charge!

 

Tell him you need to cum again and start fingering yourself as you’re scissoring with him. Have an orgasm (pretend if you need to).

 

Gasp to him that it was having a sudden vision that he really was a woman and that he was fucking you with a large strap-on, which popped you over the edge hard.

 

Say, “Fuck, that vision was so fucking hot!”

 

Bite your lip and look nervous. Start to say something and stop. Blush if you can. Start again and stop, then speak softly, “I think it would be so hot if you bought a strap-on slightly bigger than your beautiful cock. Then dressed in your knickers, stockings and cage, and fucked me with it. I think I’d cum so hard I’d have to give you a reward afterwards. Would you do that for me? It might help me decide if I can let a woman do that to me when she makes love to me.”

 

Smile and say, “Wouldn’t that be a great show for you?”

 

Then, look down and away as if embarrassed to be asking.

 

Silence is once again your best friend. Never beg and never berate him if he won’t do it. Instead, use the withdrawal of affection and reward system discussed earlier in this post.

 

Give him time. If he hasn’t bought one after a week, ask if he had thought any more about getting a strap-on as you really wanted to try it with him. Say it makes your pussy throb every time you think about it, which is all the time.

 

You need to ensure that you give him no relief during this time. Even if Saturday comes around, and he’s all freshly shaved down there, tell him to put his cage back on and say that he may have a wank by himself before putting it back on if he wishes. Don’t allow him access to the net, though. Instead, make him come up with his own fantasy to get off. If he does manage to cum insist he tells you what he fantasised about.

 

Hopefully, it won’t have been about your sister.

 

There’ll be a good chance it will be about you with another woman and him joining in. Tell him it’s possible but that he needs to help you overcome your fears first. And that having him shave off all hair below his eyebrows, dress like a woman, and then make love to you like he was one would help ease some of your fears.

 

14. Teaching him his cock is not needed.

 

He will eventually buy the strap-on and give it to you. Make sure you bring the fantasy to life as soon as possible after he has given the strap-on to you. Get into the shower with him when it’s time for him to shave himself down and do it yourself.

 

Use all of your skills to get him as excited as he can be without cumming. It is, of course, impossible to get the cage on if he’s erect, so here’s what you do: Tell him you want to raise the kink to a new level and take him into the bedroom. Using some of your pantyhose, tie him, spreadeagled, to the bed. Blindfold him with one of your scarves and stuff a recently worn pair of your knickers in his mouth

 

Recently worn is best, especially if you were aroused when you wore them because the smell will drive him wild.

 

He won't raise even one objection if you’ve made him horny enough in the shower.

 

Go to the kitchen and get a damp cloth and a teaspoon. Wrap some ice inside the damp cloth and give it a few minutes so it is cold. Next, go to the bathroom and rinse your mouth with a little bit of toothpaste.

 

By the time you get back to the bedroom, he will have started to flag a little but won’t be soft. Take his cock in your hand and begin making him hard. As he reaches hardness, take him in your mouth. Don’t suck. Just mouth him and gently breathe in and out with him in your mouth. The minty freshness of your breath will cool and then warm his cock and bring him instantly close to orgasm.

 

Do not let him cum!

 

As soon as you sense he is close, hold the damp cold cloth against his balls and smack the eye of his penis with the teaspoon really hard! Unless he’s a total sadist, he will go soft immediately.

 

You want him horny but not hard.

 

Place the cock cage on him, then make him as turned on as you possibly can again. Do the same as you did the night you first pretended he was a woman and made love to ‘her’. Keep tormenting him until he groans in pain because his cock is throbbing against the limiting constraints of the cock cage.

 

Ask, “Do you want to cum?”

 

Of course, he will say yes.

 

Then say, “If you dress up as a woman again, put the strap-on on and gently make love to me until I’m satiated, I’ll take your cock cage off and let you fuck me for real, deal?”

 

He will instantly agree. Untie him, take the blindfold off and your knickers out of his mouth, and then hand him the stockings, thong and strap on. As he wrestles with the stockings, hand him a camisole top to wear as well.

 

Don’t say anything. Just indicate he should put it on, too.

 

Once he has all the gear on, help him to put the strap-on on and tighten up the straps. Position it so it’s resting on his cock cage, not his pelvic bone, as it should be.

 

You’ll want this to be a little uncomfortable for him, so he won’t want to do it too often. The goal is to get him used to the idea you’ll want a bigger cock than he has in you before too long. And that he can’t satisfy this urge by getting increasingly bigger strap-ons.

 

Once he is all done up, lie back. You’re going to do as little as possible so that everything is up to him.

 

Tell him, “You need to warm me up with lots of foreplay because that’s what a woman would do, and I want to experience that.”

 

He should be stroking, kissing and licking all of your erogenous zones before he goes close to touching your breasts or pussy.

 

Once he has completed his tour of your erogenous zones, get him to gently massage, stroke and lick your breasts until he can feel your arousal. Then he can use his tongue on your clitoris and vulva to drive you even higher. Finally, he should dip his fingers inside your pussy and gently stretch your pussy with one, then two, then three fingers to prepare you for the larger-sized ‘cock’ he will fuck you with.

 

When you’re ready to be penetrated, ask him to lube the ‘cock’ and gently insert it into you.

You’ll need to lube it as there is no precum to prepare the way, and your own juices probably won’t be enough.

 

Take your time, and make him take his until you are used to the extra girth and length.

 

When you’re ready, whisper huskily into his ear, “Fuck me hard now, you beautiful sexy girl!”

 

Make sure you push back at that ‘cock’ hard enough, sometimes, so that it hurts his balls.

 

Keep calling him by feminine pronouns. “Fuck me, darling girl. My god, you sexy bitch, you’re making me so hot! Etc.” so he believes you are fantasising about him being a woman. Cum hard and loudly at least once, numerous times, if you can.

 

Once you’re fully satisfied, ask him to gently remove the strap-on from your pussy and tell him to take it off. But ensure he remains in his female clothes, including the thong and top.

 

Release him from his cage and get him hard as quickly as possible. Guide him inside of you, then ask him to fuck you hard again. As he fucks you continue to call him by female pronouns. As soon as he cums, cum too.

 

Time to pretend if you have to.

 

Drag him over so he’s lying on his back, and snuggle in as close as you can to him. Play gently with his cock. Stroke his stockinged legs, slide your hand inside his camisole, and stroke his chest. Lavish praise on him. Tell him how good he was, how hard you came, how much you love him and how much you appreciate what he did for you. Call him your sex god and the best lover you’ve ever had.

 

It’s called ‘stroking his ego’, so he’ll want to do you like this again.

 

Don’t even make him clean you up or put on his cock cage. Tell him you want to fall asleep with his cum running out of you to remind you how good a fuck he is.

 

15. Further feminisation.

 

In the morning, he will be hard again and will want to fuck you because he will think things are returning to normal. Don’t let him! Tell him you are too sore from last night (it doesn’t matter if you are or not). Send him off to get a warm wet facecloth.

 

Wash under the covers. If he asks why, say, “Because I don’t want you to see you’ve hurt me by fucking me that hard and well.”

 

Then tell him you want him to cum on your breasts.

 

Don’t help him at all, but let him straddle your torso as he wanks himself off. Once he has cum, gather a little bit on your finger and make a real show of swallowing it. Then make him use his tongue to clean you off.

 

Make him clean his cock and groin area with the same washcloth you used, and put his cage back on.

 

Tell him you feel like some Maccas for breakfast but don’t let him take his female clothing off. Instead, allow him to put something on over the top so the fact he is wearing women’s clothing is hidden and send him to get some.

When he returns with breakfast, emphasise that you expect him to stay clean-shaven from the eyebrows down now, except when he is wearing shorts. Then he can leave the stockings off. He was to wear the stockings, knickers and a camisole top all the time at home because it makes you so horny to think of him as your ‘secret girl’.

 

Explain to him that if he does this, he will be rewarded for making you happy.