How To Feminize A Reluctant Sub In A Gentle Femdom Relationship

In any female led relationship the controlling dominant female has many things to juggle around. Most likely the running of the household, and making sure the relationship runs smoothly.

While there is also the work of correcting bad male behavior there is also the fun, kink, and humiliation aspects of mistress’ dominance.

BDSM in all its forms has many devotees who like a specific aspect of the lifestyle, from severe canings to men who like being treated like a dog, and publicly humiliated as such.

Personally, my wife and I are more into the gentle femdom aspect of it, rather than any severe, or constant lifestyle choice.

I don’t want to be entirely emasculated.

One aspect though is the practice of the sub being forced into female clothing as a way of diminishing the subs masculinity.

So men are indifferent, some can see the value, some have never tried it, some are nervous, some have a reluctance to the practice but will do it if mistress demands it. Some have a harder resistance but can be teased and coaxed into it with techniques applied by mistress.

Quite frankly, mistress might actively enjoy the practice, for fun, kinks, or likes to lightly humiliate you slightly occasionally.

If the sub really hates it then it could be a good punishment even.

So, in terms of the article what are we talking about here?

Well, what we are not talking about, is the males who love dressing up in female attire, and will do so willingly. We are also not talking about hardcore feminization, there’s no need for piercings and earring wearing, or attending like minded parties where dominant women bring their feminized men.

Essentially what this article is about is a female led relationship where the mistress wants to get the sub more accustomed to learning to live, albeit for a short period of time, in women’s clothing and being treated as such.

Maybe he has expressed a small desire, but stressed he will do it but doesn’t want to, or maybe you find it a bit kinky and want a maid. It could be an area he doesn’t know about but might want to be pushed.

This article is mainly offered in the spirit of pushing over the subs resistance to any feminization, and perhaps making him more comfortable with it.

It’s intended as fun, excitement, pushing boundaries, and the subjugation of your sub to the emasculation you desire and the removal of his male appearance.

What Is Feminization For A Man

Essentially feminization is a style of roleplay that involves taking all the attributes normally associated with females and applying the to a male subservient.

It is typically applied in any female dominance role and isn’t traditionally just cross-dressing, which is the practice of just dressing up like a female.

However, the male submissive will indeed be dressed in female clothing to provide a more visual and real appearance to their ‘transition’ and eventually perhaps the adoption of female behavior.

Feminization nearly always involves distinctly female clothing, not a T-shirt and jeans, as males also wear that. It’s not uncommon for everything to be on the table from undergarments to sexy clothing designed to attract males, and costumes more associated with females.

Quite often, traditionally female affectations are also applied, such as nail polish, lipstick, makeup, and a wig.

A mistress can use a feminized man to perform perhaps the more commonly thought of female tasks, such as kitchen work, and maid like duties.

Sexually speaking the feminized male will be treated as a female, have a female name, have parts of him referred to by their female counterparts and the mistress will take a more masculine attitude to her ‘slut’ or ‘whore’.

Within all that is personal preference and hard limits for both the male and female within the female led relationship.

Why You Might Want To Feminize A Man

At the heart of it is either a desire to be feminized, but need pushing, or at least indifference, and a desire to make the mistress happy in her desires.

Quite frankly he might be really embarrassed about it, but secretly really desire your authority to push him into it. Self deciding to be feminized might feel like he is essentially emasculating himself and he is uncomfortable.

He will need your authority and rule to push through his internal objections, so he can absolve himself of the responsibility of deciding.

As a mistress maybe you want to push this and see how far you can take it.

It can also be used as a humiliation and as a punishment. He may be really uncomfortable and you need to keep pushing his acceptance to provide greater punishment for him or humiliate him as a punishment in and of itself.

As there is quite a wide level of types of feminization, then you can use it as a graded punishment, and remember you can threaten punishment to ensure compliance.

Maybe for forgetting the milk, he can wash up in panties, but for severe infractions like disobedience, he can spring clean the house on the weekend dressed as a french maid.

Quite frankly it can be a fun kink for mistress as well. Perhaps she enjoys his squirming but obedience and wants to push the boundaries a bit.

Do Men Like Feminization

For many submissive men, feminization is often associated with being treated like a female, and even it isn’t as a mistress it is certainly fun and kinky to treat him as such.

Then there is the slightly more punishment aspect to it, and many men enjoy being spanked and paddled to ensure compliance or enduring the humiliation and pain for some infringement.

Nevertheless, reluctance to be feminized can certainly be present and can be a simple as applied nail polish, but can be more psychological and deeper routed. He may just like mistress authority but not the emasculation associated with wearing female attire.

The majority of men in a female-led relationship may not actively like feminization, but under mistress’ insistence will do so albeit with a worry about how far she will push it.

I think I probably fit into that category.

Thus most men, even though they are reluctant, with strong encouragement from mistress will actually perform her required desires in this area.

Why Men Submit To Feminization

At the heart of any female led relationship is the male subs desire to have his mistress as the controlling authority.

He will likely feel that some of the authority he has in the world is derived from his masculinity. Men naturally have more strength, stamina, and assertiveness.

Submitting to feminization is a way to emasculate him, which provides temporary relief for him from any male aspects to his life and stresses. That may indeed by what attracts him to gentle femdom whether he is consciously aware of it or not.

There can also be a powerful sexual driver to his desire. He may enjoy a dominant female, with more masculine traits, and as such must submit to feminization himself as the natural counterbalance.

Engaging in sex as the subservient feminized male might be an outlet for all the pressures on him as a male. 

Frankly, there are a load of reason, some of which you may never need to get to the bottom of, some may be simple and rather more identifiable.

How to Use A Feminized Man

The best way to use your feminized man is to understand why he might be complying with your requests.

In a female led relationship you know your man. Your REAL man, So you will probably know why and what his desires are, so you can use that and work with it.

You should assert his feminization both verbally and physically. You should use the two combined.

You can decide to toy with him and be both sexually suggestive to keep the emasculation going. Additionally placing your own female persona into the mix can add heighten elements.

You could try the caring, loving wife with;

• Superb job on the bathroom cleaning, really done very well
• You really do make superb tea, my dear
• Would you mind fetching my keys, sweet pea
• There you are angel, you look particularly good today, all the boys must love you

Or even suggestive, instructional and forceful

• Walk less like a slut, my dear, more confidence from you
• Wiggle that ass you walk my dear
• There you are maid, I need a cup of coffee now
• Finishing organizing the cupboard and then find me for the next task
• I expect to see your best effort on this, my dear

Or frankly, you can add the kink element.

• Ooooh, sexy ass in that skirt, I should get you a stripper pole
• Holy cow that’s sexy, that’s an ass that needs to see some action
• I’ve dressed you too sexily, you’re making me horny to peg you now
• Are you getting wet in your secret girl’s place?

Frankly, you can use your feminized male in any way you want, up to his limits. You can do it small and often, irregularly, or every now and again, just to keep him on his toes.

You can use him for fun, kink, a humiliation a little, or even as a punishment.

So, How Do You Feminize A Reluctant Man

So, the crux of the matter, if there’s a reluctance you sense or want him to grow his acclimatization to the idea of feminization then there is a small technique that can be used.

This isn’t offered as a step by step guide but a way of thinking about making your man a more feminized version of himself whether he has little desire to do it or not.

If you work through the steps you should get to your ultimate goal of a man that will more happily get into female attire, and be treated as such.

Setting Goals

This is why you define what you want from your feminized man. Every mistress will be different, and as you are dominant in the female led relationship there isn’t necessarily only one.

Housemaid – You want to train a housemaid to emasculate your sub. He will do a lot of chores around the house, from show cleaning, kitchen cleaning, and spring cleaning. These are more traditionally more homely and female tasks. Your sub needs to overcome reluctance to his feminization so you can have a French Maid.

Slut – Your male sub needs to be feminized so he is treated like a slutty female. He will not be dressed in elegant attire, but perhaps clothing more appropriate to a hooker.

Lesbian lover – As a mistress, you need a lesbian lover, and want to transform your sub so that when you have lesbian fetishes he can accommodate you.

Emasculating power – Your male sub has too many masculine issues that cause you problems. As a punishment, he needs to be feminized.

Start Small

If he has a reluctance or low tolerance starting point you need to start small and keep observing his attitude as you increment the steps.

Maybe he would be OK with panties, but a full-on stockings, suspender belt, bra, with matching undies and wig and lipstick is a bit much to start with.

You can grow ever so slowly and maybe get him there, but it may be just too much for him as a starting point.

If he is full-on reluctant in any way but has said he will do small things with regard to feminization to obey you then, then you need to start ever so small in the process.

By starting small, I mean;

Panty carrying – Make him scrunch up a pair of sexy undies in his pocket at all times when you go out.

Panty wearing – On a shopping trip or a visit to the cinema get him to wear sexy panties while he shops or enjoys the film.

Bedtime panties – if he has done a few small transgressions then why not make him wear the panties to bed.

Workwear – Get him to wear them to work and send you photos as proof. Request more than once a day so even if he cheats he has to get in and out of them.

Health walks in panties – Make him walk to a local store in them and get you something.

I’m sure you get the idea, it is to get him to start thinking of the act of wearing panties as your kink and it’s almost pretty small. There’s nothing overly emasculating about any of the ideas for starting small but sounds a bit like a fun link.

His head is starting in the right place.

Techniques To Overcome Reluctance

Before we go on, it’s worth noting some proven techniques for overcoming resistance. He may be very reluctant and considering giving you a ‘hard limit’ or ‘near the limit’ acknowledgment of his discomfort.

If you get a near the limit notification, then consider taking a step back a notch and applying the techniques below.

Create a connection – this is a process for overcoming the isolation and feeling of social distance. When he is starting he may well feel a little bit alone and will react with a ‘near the limit’ as a defense.

You can easily overcome this by almost joining him in the task. Why not put your panties on together, or help him get into them.

You could even take a photo of your underwear at work and send it to him. In small increments, and joining him in the tasks you create a connection where he may not want to drop out or be the first to call ‘timeout’.

Provide choice – Often providing choice can give the illusion of control, as he can take the least bad option for him and it tricks the mind into thinking he actually chose that option.

Choices like

• Red or blue panties to work today
• A healthy walk in panties or shopping in panties
• Sleeping in panties or washing up in panties

You can offer your preferences if you like so if he feels a little recalcitrant he can choose the other option.

Association – This works on the principle of positive reinforcement. What happens if he is uncomfortable wearing panties, then you can make him do it, and connect the panty wearing to an activity he does like.

If he loves Xbox then make him wear them while he is playing a few times, or if he likes watching football, hockey, or a baseball game do something similar.

If his team does well, he gets excited, or if he does well at Xbox then the same thing happens.

Either way, you are connecting desirable behavior with him beginning his feminization.

Shared experience – Similar to creating a connection but this can have a more intimate and sexual element to it, but doesn’t have to. It can also have an element of longevity to it.

When you create a connection like both putting on panties, then you can both go to work, this creates the mental connection, but a shared experience means you are in each other’s company while sharing that connection.

It provides both reassurance and affirms acceptability.

Such as

• Go the cinema with him wearing panties and you not
• Both get into bed for sleep in panties, stockings, and garter belt
• Watch a movie at home both in stockings
• Get him to put on some nail polish for you, then you can put some on him
• Paint your toenails together
• Go skirt shopping for each of you

As a mistress, you can frame this as a kink, and make it spontaneous, but the key is to create a connection that makes it less like a singular experience for him.

Reward – Occasionally there might be a bit of a jump for him in terms of reluctance. He may be OK, with wearing panties, or vacuuming naked for you but does not like the idea of putting on stockings, or a wig, or having his nails done.

At some stage, you may meet his resistance line, and receive a ‘near the limit’ warning.

The idea of offering a reward is that it produces a huge incentive for the sub to overcome any internal resistance and if the reward is desired enough will defocus the mind away from the reluctance and towards the reward.

Unsurprisingly, sexual rewards can often be the most effective.

While you could threaten punishment for noncompliance, your sub could technically get a ‘timeout’ and say that was unfair because you are pushing a hard limit. This is much less likely with a reward he desires.

A reward is much more effective.

Imagine your reluctant sub is having an issue with putting on panties, stockings, and a garter belt. Panties he was OK with as it felt like a small foray, but this is currently feeling a little too far towards a limit.

Now imagine the effect on him if you were asking in the bedroom while lying on the bed and playing with yourself.

Comments like “I really want a man in stockings and panties inside me” might really focus his attention away from his reluctance. Further teasing might produce a real passionate desire in him to actually leap over his resistance, not just step over it.

So try;

• Slip into those panties and I will let you give me oral
• Put that skirt on and I will give you the best BJ ever
• Wear that bra and blouse for shopping and we can make love tonight
• Wear the french maid outfit to clean and I will wear that nurse outfit

I’m sure you get the idea.

Acclimatization – This is a step to get your sub used to and comfortable with a step, that previously might have seen as apprehensive.

Again, let us suppose that putting on stockings and a garter belt was a stumbling block. Through the use of creating a connecting, providing a choice of stockings for him, shared experience, and offering a reward you have managed to get him to try it.

He has been in panties, stockings, and garter belts once or twice.

The last thing you want to do is move straight up towards trying on a bra and blouse, or into a french maid outfit.

Wait out a little on the process of advancing the stages of feminization and definitely no large leaps.

Acclimatization is the process of staying at the same stage and repeating the procedures that work.

You should keep doing more of what works, and not try to upset the imbalance too early.

Put simply, don’t advance to the next stage of appearing more feminine without him being comfortable with the current stage.

TIP – His acclimatization can be tested by removing the connection, choice, shared experience, or reward. If you have only managed to get your sub into panties, garter belt, and stockings by offering rewards, then try removing the reward and seeing if he complies.

Get him performing a chore with the stage of feminization you are at without the techniques applied above. If previously he wouldn’t wear a bra and blouse and only has done so with some rewards, but then does it without the reward, he is growing acclimatized to that stage of feminization.

Go Very Slow

The process of moving from thinking that ‘a man putting on silk panties’ to wearing a french maid outfit and dusting the house isn’t going to happen in a week.

Remember, we are talking about overcoming reluctance here, you do not have a positively willing slave, but think he may like having his boundaries pushed or has expressed that he doesn’t know where the line may be.

So you have to go slow. At each step, he must grow comfortable and acclimatized. He must stop thinking of the step he is at as repugnant, but at least be indifferent to the feminization request.

What I offer below is a small guide to your starting point and a set of steps that make sense in small increments of feminization.

At each step, you should spend some time on, not just see it as a quick point to get to the next one. At each stage, there is the point of your sub being acclimatized to the current step.

It’s not a race.

You can also miss a step, or move a few around, whatever works for you. I offer them as suggestions only.

Nor should you need to start at step 1. Your sub may be more comfortable already with simple things, like wearing panties, and you can move up the steps to where you might want to start.

Perhaps drop back a stage and practice the ‘overcoming reluctance’ techniques I told you about earlier for your self. You might need to be more practiced later on.

Note: These steps aren’t accumulative. We start with something simple like panty wearing, and later on, there is bra wearing. He shouldn’t already be in panties when you try on the bra for him. You can add the steps together as you see fit.

Note 2: If at all possible keep it light-hearted, fun, and kinky as this has a much better effect than anything else. Saying “oooh go on, get that ass into those panties and stockings, it makes mistress so hot” has a good, positive and reaffirming element to it that will more than likely succeed.

The early steps in the below list definitely move in the kink direction, as that is the surest way to get compliance from your sub. You can introduce it later at any stage, but connecting feminization to the libido early on, makes overcoming reluctance much easier.

So, where do you start?

Step 1 – Wearing Panties: probably the best starting point and most men, even very masculine men in a female led relationship do not have a problem with a mistress issuing this type of instruction. It can be a kink and a humiliation that isn’t seen by the sub as particularly emasculating and shouldn’t be an issue.

You can start small, like watching a movie in panties, or doing the washing up in them while you giggle a bit, and progress to more acceptance with shopping, wearing them for a weekend or going to work in them.

The longer the time you can keep him in them, within reason, the more you can assume he is comfortable with the first stage of feminization. Try getting him to wear them to sleep and cuddle up with him in them.

Step 2 – Stockings: from the previous step, you should pay attention to where he is the most comfortable in them and does it without hesitation. If there was resistance early to wearing them to work, now gone, but leaps into them for sleeping and cuddling you in them for the night, then start there.

Use your best judgment.

The next step is to get him into stockings. Typically female and connected to arousal in men, you should purchase a few of his own sets and attempt to get him into them.

Start with short and simple incidents of him wearing them like as a small kink while he washes up, or while you give him oral, or even just while you watch something for half an hour on the TV. Keeping the early stages, simple and kinky eases him into the acceptance. Gradually increase the length he has to be in them and when.

Step 3 – Garter Belt and Stockings: with the addition of the panties at your discretion. We are starting to get into the area of female clothing associated with sexual activity, or elegant attractiveness.

Going from hold-ups to a garter belt and stockings shouldn’t be seen as a huge leap but again, start small and gradually increase the length, and occasions when you want to see him in them.

You might have had him washing up naked for a while, and then insist he does it in the garter belt and suspenders (no panties as you want to see him hard), and then go from there.

Again start small and work up to longer periods of him in them, such as

• Wearing them at the weekend under his trousers
• Wearing them under his trousers on shopping trips
• Cinema trips with him in them, again under trousers
• Performing longer tasks in them, like vacuuming the house

Step 4 – Bra: this can often be a big first step, as it’s a more unusual step. The easiest way to introduce it is in a sexual context. Leaping into wearing a bra while shopping can often be a large and unnerving step.

You can often make it sound casual, or really spontaneous kink you want to see, It’s probably more ideal NOT to do this while he is already in panties, or a garter belt and stockings.

The first bra wearing should be in isolation, but be in a fun and sexual environment. As mistress why not tell him you want to receive some oral pleasure. Tell him to shave and get ready.

While he is doing that you can wave a bra for him and say you want a bit more kink, and he should put this on. With the anticipation of sexual activity on the cards, he may well comply. The threat of you withdrawing the oral may overcome any trepidation he may have.

Once he gets used to having it on while giving you oral, or for a receiving a BJ then you can introduce it for some small task, non sexually related.

Try “I’m trying to decide if I’m horny, do the washing up naked but in a bra while I mull it over”

Start small, withdraw the sexual element, repeat and acclimatize, and then increase the longevity.

Eventually, you can move to him wearing a bra under his sweater while attending the cinema, shopping, or on date night.

Step 5 – Sexy Combo: now might be the time to try a sexy combo. Good to make it light-hearted again, if he is uncomfortable at all, but you should judge that at all times.

Fun and kink, as alluded to before making a sub much more likely to comply.

Try;

• Mistress wants a massage with you in bra, panties, garter belt and stockings
• Get into that sexy gear and I will let you give me oral
• Let’s sleep together tonight in sexy gear
• If you get into a bra, panties, and stockings I will give a BJ right now

After that, you can start with the small chores, again like washing up, vacuuming the hallway, or cleaning the bathroom.

Step 6 – Negligee: nothing too subtle about this one. A negligee is a highly provocative piece of female clothing associated with trying deliberately to look sexy.

So that’s probably a good place to start when you want to see him in one. Have one on yourself maybe and make him sleep in it, or watch a romantic comedy together and both wear one.

Gradually he can start wearing it on his own, like when he is cleaning the bedroom or bathroom.

Step 6 – Heels: not always necessary this one, as most feminized men have no intention whatsoever of letting anyone know it’s a thing they have to do for a mistress, but can be an interesting twist for sure.

They will never go outside in female attire, so have no need for footwear.

Also, not least of which is the fact that men, almost universally, have no experience of at all of the difficulty of learning to walk in heels, which is an interesting thing, as you can use that hook to get him into them.

Try;

• I want you to appreciate how hard it is for me to walk in heels
• It’s something I bought to make doing your chores harder when I feel like it
• Your sub looks funny in them and it amuses me
• I wonder if you can remain upright in them while I give you oral

So you can buy a cheap pair for him and pop them on him while you watch a movie and ask for a few coffees from him, or make him wear them while vacuums the front room. Hopefully, it looks like a trial rather than an act of him growing accustomed to female attire.

Step 7 – Blouse: probably nothing to elaborate, but a simple white blouse which has some obvious feminine touches like frills, or a lower cut should be the order of the day here.

Ridiculously feminine might be a bit over the top but it is entirely up to you.

He can wear it to start as sexy night attire, or while he performs a small chore, but eventually he can wear it under a coat while shopping. Stay with the small kink and funny if you can.

Step – 8 – Skirt: this can be a humiliation piece for him or some garment you want him to wear while he does any feminine chore, like cooking for your amusement. Again, you can do the girly film watching with him in it, or vacuuming even.

You could even give him oral with him wearing it, saying you don’t want him to see.

Start with small times in at as usual like a very small chore before he can get out of it, and increase the time. It’s unlikely he will wear a skirt outside as it can’t really be hidden, so you should probably never try.

Male sure curtains are closed so prying as will never catch a glimpse.

Step 9 – Combo (torso): if he can be made to step into a skirt for short periods of time then a small time in a bra and blouse should be easy.

Again, maybe watch a female orientated film in them, but eventually, you can have him wearing them on shopping trips under a coat or sweater.

You can then combine it with the stockings and suspenders if he will go for it.

Step 10 – Dress: – the dress is a very distinctly feminine piece of attire, but you can have him in the for the traditional short periods of time initially.

For someone reluctantly into feminization, the dress can be a sticking point.

The reason a dress is a top and bottom garment. Before with you have been concentrating on the top half or the bottom half of his frame.

To start with you can again, just get him to put it on for a massive reward, and then take it off immediately, and gradually increase the duration of his time in it.

You could tell him you’ve thought of an interesting humiliation, and keep him in suspense – or a punishment item, and get him acclimatized. Put him in a dress for spankings or something if he likes that activity.

Another idea is to associate the dress with a very specific activity and call it as such.

• Get into your vacuuming dress and do the hallway
• Pop into your laundry dress and get all my blouses done
• Get into that cooking dress and make me a spaghetti
• I see some dirt around, get into your dusting dress

That way it’s a very small humiliation for him.

You can increase the length of the chores, and combine them, so he does the laundry, and then the dusting in the dress.

You can ever so slowly add other elements of the female attire. 

“Let’s have some panties with that dress today shall we”

Step 11 – Outfits for chores: by now you should be able to tell him you are thinking about getting him a small outfit for the female chores he has to perform, and it won’t shock him as it might have.

The simplest form of outfit that fits with chores is a maids outfit. You can pick them up from a lot of places online.

You can put them into it for when he does a feminine associatable chore such as the vacuuming or dusting, as per normal.

It’s quite possible you can add the stockings, panties and garter belt as well.

Step 12 – Affectations: feel free to add perfume, handbags, nail polish, or a wig if he has little reluctance now, but they are not always necessary.

Step 13 – Feminization freedom: at this stage, you probably have a great deal more freedom to put him in female attire and treat him like a maid or a servant than you did at the start.

He has grown used to, over time to getting into unnatural clothing and being treated slowly like a maid, or female.

You can assess the level by which he feels comfortable, he may not want female related clothing and treatment every day but occasionally, and when you want to punish or humiliate him.

Gauge it well and play be his comfort levels where possible.

Repetition

This is key and doesn’t necessarily have to happen in short bursts, but a man putting on a dress for the first time will feel ridiculous.

The shorter you make it, and the rewards you offer for compliance, along with repetition can make him accept it a lot easier.

For example if he was really reluctant, but got a BJ from you every time he did it, it becomes a lot easier down the road because of the different associations.

I’m not saying you should, but I am trying to illustrate the point.

Repetition will help acclimatize the sub to feeling more normal, and less ‘weird’ as he does it more often.

Tease

Teasing your sub can often be a very effective tool during this process. Whether it’s gentle teasing, to telling him he looks sexy in that skirt, can change the atmosphere to light-hearted in an instant.

Remember, this is meant to be satisfying for both of you, and making it fun should be a goal.

Rewards For Progress

When you sense a real stumbling block this can often do the trick to provide that extra push to move towards your goal of feminization.

Positive reinforcement is the effective use of a reward for performing the right behavior.

Negative can work for some subs, such as great threats that overshadow the small embarrassment, but rewards work better from my experience.

You can combine the two, of course, to provide the carrot and the stick. “Put this skirt on and I will let you take me in it right now, don’t and you won’t be allowed your Xbox for a week”

Progress tips

You can offer to drop existing punishments if he’s grounded say, and you sense the opportunity. If he really wants to go out with the boys on Friday but is grounded for a serious infraction, then holding up a dress on a hanger, and saying “vacuum the house in this, and I will let you go out on Friday” produces a very interesting conundrum for him.

Nine times out of ten, he will vacuum the house.

Likewise, you can exchange punishments for feminization compliance. It he is late home and forgets the milk you asked for, you can either get him to walk to get some more or ask for a drink of orange while he is in a skirt instead.

Some Kinky Tips For A Feminized Man

As previously mentioned, keeping the fun and kink into this really does overcome a reluctant subs fear of being feminized, so the best play is to make it mostly predicated on kink, sexy fun, teasing humiliation, and humor.

You can probably think of a few that personally suit your sub and would work, but in the spirit of giving you an idea, you could try these teases and plays;

Strapon penis – When he is in female gear, like panties and stockings, you can refer to his manhood as his ‘strapon penis’. Delivered with a wink and a smile it is disarming and has quite an effect.

Lesbian lover – If he is in sexy gear, like a bra and the matching ensemble, you could always say you’ve wanted a lesbian lover and take him to the bedroom.

Oral practice – Get a penis dildo, or a fake vagina and get him practicing his oral technique in his negligee or stockings and panties.

Conclusion

As you can imagine, the process of feminizing a man is largely a trip inside his head.

Overcoming resistance can often be a matter of small steps, acclimatization, and encouraging words from you.

Maybe he thought he’s fear something he didn’t. You not mocking him, and it being private might be enough, with repetition and small, slow steps to keep him progressing towards your end goal.

You don’t have to sink thousands of dollars into this and get him in Versace dress. Go into thrift stores together, or check out the sale items, and shop together for a dress, a skirt and some heels and blouses in his size.

It should never feel like a chore, or truly forced, and making light of it, and sharing the experience of feminization can often be the key that unlocks your partner’s feminine side.