He will Obey - Guide and Training

As for style of panties, anything works, but I would recommend something really sissy like full cut. You want as mush silk/satin touching his skin as possible. When we get to man-scaping, this will become apparent what we are trying to do. Make sure to try different styles initially, so he can experience things, full-cut, etc. Keep him guessing, and anticipating.

Later, we will get to his second pair of panties. Sissy's should always wear 2 pair of panties (to be explained later). But a nice thong or G-string feel perfect when he is plugged. A first pair can be used to "contain" (granny panties), with a second ultra-frilly pair on top. Also, first pair can have "rear-access" hole, for Mistress, while second pair are at sissy's ankles, etc.. Lots of scenarios.

After he has become used to being pantied on the weekends, we move to weekdays, under his male clothes. Start slow, maybe 1 day per week. Start with Fridays, as to build anticipation for the weekend. Then the weekend can include ultra-feminine panties like super, frilly, little girl panties. It's hard to be "manly" when wearing Princess panties!!!

When you have him wearing panties like a good boy, s/he'll be so much more submissive and willing to please!

When alone at home, make sure they are super frilly!!!

Wearing panties daily is a must for a sissy so s/he better get used to the feel and look of them!

For work, it doesn't matter if he still wears boxers over his panties for now. You just want him pantied, and not to be exposed. This is YOUR SECRET. This builds intimacy and trust in your relationship.

Once you have your husband used to wearing panties we want to enhance that experience. We want him to be able to completely feel the silk/satin panties against his skin. So now we start suggesting "manscaping" his private areas..... front & rear.

Some are tempted, to use feminine products, but this is up to you.

We are trying to COAX him, encourage him, not scare him. So we must use wisdom here.

But, we do want him clean shaven.

At this point, we are ONLY focused on private areas, nothing else. We are still associating the panties to great nights.

Pantyhose

Even beautiful women, who don't need to wear pantyhose; understand their appeal and affect on the male. Men are visually stimulated, but we are going to continue to have him feel "encased" in feminine

finery (silk/satin).

You want to start imprinting the concept of panties & pantyhose together. Initially, you will need to show off your assets, to get his mind focused on what you want.

You can decide the best way to do that. You should make sure to tease him, rub your smooth legs against him as much as possible. Create a desire.

Then you are ready to add pantyhose to his wardrobe. As with panties, start slowly; on weekends. Move to once a week, eventually daily. We want him ENCASED in femininity.

My husband wears pantyhose to help keep in that butt plug in his pussy and it is very effective.

Soon he will desire them (and you) intensely. Then we can show him, that wearing pantyhose under clothes is awesome; including yourself. Go shopping, pantyhose under his jeans, let him feel it.

Soon, he will want more and more feminization.

Girl's night

By nature, men pay zero attention to their toenails!!!

As always, we start slowly. Friday night home alone. We want to convince him that toenail care is important, because we don't want runs in his pantyhose.

Initially, You want to do his pedicure. All the while being encouraging, coaxing, reassuring. You want to talk as you work, so he learns.

You want to use your pedicure kit (pink preferred). Get him accustomed to the idea.

Clipping, Filing, etc., all as you talk to him.

You want to end with a clear nail hardener, strengthener. Assure him no one will ever know, it's clear!!!

Eventually, we will get to manicure as well; but we have a ways to go first!!! Start slow. Let his mind absorb the changes. Keep it consistent. Check his toes weekly.

Bedtime

Matching nighties is a great start. Different colors. Yours should be black/red (Dominant), his should be feminine colors, like pink, white, etc (submissive). enj

As always, start on a weekend, as this will affect his sleep. You want ultra frilly; lots of material.

We also want to make sure he is wearing it ALL during your fantastic nights together; plus you want to reward him the next morning.

That means crotchless panties (or push them aside), but do NOT remove them. Pantyhose also need to be crotchless. You want lots of silk & satin rubbing him.

You want to be on top of him; make sure he feels all the silky materials rubbing together. Repeat every weekend, and then as much as possible; until it's all he wants to sleep in.

Make sure s/he has a variety to choose from; and you as well. Keep a variety, including robes.

Get him addicted to the feelings. If you continue the loving, encouraging, coaxing approach; he will desire more.

Remember to ALWAYS reward him for wearing his nighties. Make sure you have fantastic nights together, even if just lounging on the couch this doesn't have to be sexual. This can be a time you are having plain conversations.

Below is a list of additional ideas you may wish to explore.

Waist training, we want to ensure he/r can wear it daily, under he/r work clothes.

We start with a wearable waist cincher, that can't be seen under his normal male clothes.

Hook & Eye fasteners are good; as they are involved in many areas of women's clothing.

Some have shoulder straps, which is ok; if they have no breasts.

Different lengths are available. We want he/r cinched Mon-Fri at work.

Different materials are also available. But we want he/r to take the waist cincher off at night.A zipper, over hook & eye closure is sexy. Very good concealment.Make sure it's tight, but not noticeable thru his shirt.

At this point, we need to give he/r a feminine name; an identity. This is a very important aspect of feminization.

Most couples have secret / pet names for each other; it's part of a healthy relationship (a shared secret). We want he/r to have a femme name for many reasons.

As the Mistress (Wife, Girlfriend, S/O), it is largely your choice for names; however, it should be a topic of discussion first. Why? Because we all have a past.

We want to ensure that the name you choose, doesn't have any negative connotations. What I mean by that, is, we need to avoid old girlfriends names, or the name of any girl that may have been unkind to him before.

Once a female name has been chosen, you want to start using it regularly. You want to refer to "her" in the third person. This allows his male persona to disassociate from the feminine side.

You can be at a restaurant, and use "her" name, and have a full discussion; without other people knowing who you are referring to. Again, this is a secret between the two of you.

Make sure to use he/r name during your love-making. Imprint the silk & satin, fantastic nights; to her feminine persona.

I love having my sissy pleasuring me orally. He is to have his full outfit on every night except when we have what we call a brake time ( a night that I need my husband in all aspects) he will service me and I will feel the pleasure of being pleased by a soft delicate sissy. Often I will rip of her wig in pleasure. I don't think of my my sissy being my husband I think of her as my slave during this time. Yes sometimes she will put on a strap on and pleasure me while i humiliate him calling him little dick sissy and so forth.

I need that I enjoy from a woman like my sissy. My sissy sleeps as a sissy every night almost.

We want them to have breasts, and we will make sure to comment on that during love-making later.

Waist cincher

You may want to it him in a waist cincher

The more confining, the better. However make sure you can make love while he/s is wearing it. That means open or snap crotch

access.

Whenever home alone at night, we want he/r in a body shaper of some form.

You will find that encasement is a big fantasy in the crossdressing community.

To be "encased" or trapped in femininity is erotic. Make sure to comment on her breasts, or lack thereof, during love making.

Now that we have he/r in a body shaper, with breast cups; we want to fill in those breasts. We want breast forms, or a full breastplate. I recommend both

They come in foam, gel, etc. We want GEL, so that s/he feels the weight, and they move more realistically.

S/he should wear he/r breast forms to bed nightly, and especially during love making.

You must choose at this stage, what size breasts you want he/r to have.

You can't change he/r bone structure, so he/r rib cage measurement is pretty well set.

But he/r cup size you determine. Bigger is better.

Now that s/he has breast forms, let's get he/r into a bra.

We will start with lots of support, so s/he can feel it.

Like the 18-hour bra that s/he can wear all night.

We will also get he/r training bras that s/he can wear under he/r boi clothes without detection.Bullet bras are a lot of fun for playtime, so get many styles.

Lacy, frilly bras are also fun for softer moods.We will also get he/r sports bras in future steps.Long line bras work well with he/r breast plate.

Face it, men are not in tune with females. They would be okay with wearing the same shirt for a week if they could get away with it. They only shave when they must. This is one of the bonuses of having a sissy as a slave. A sissy is taught appearance is important it's everything. The interesting thing is that men have a fascination with cross dressing however they are terrified of being ridiculed. Pretty sad actually...

Maid service

Many people hire a housekeeper/maid service to come in once a week to help. By having your husband/boyfriend be the maid, we can not only save money, but deepen your relationship by regularly engaging in his cross-dressing needs. As I have stated in my Cross-Dressing Cycles article, it is important to have a regular crossdressing session with your slave.We like to use SISSY MAID SUNDAYS.

Getting started is easy. Start simple, and as the weeks go by, increase the tasks, duration, etc. The Wife (Mistress) needs to create a task list. Starting with simple things like dusting, vacuuming, maybe dishes, laundry, etc. Each week the Mistress should adjust the list; either adding more tasks, or being more specific on tasks. Initially your maid may only need 1-2 hours to complete her tasks, but it should be increased so that eventually it is an all-day thing. The longer s/he is enfemme, the better.

The longer you do this, the more elaborate you can get. Breakfast in bed, maid runs your bubble bath, personal massages, etc. Pampering can be added as a service. All the while this is happening, the maid is learning to be submissive and obey her Mistress. Also, the wife is learning to be more Dominant, and she will see the effects that crossdressing has on her husband.

Some cross-dressers never go past the sissymaid scenario. They find it fulfills most of their desires. Especially when rewarded with strap on/pegging session as a reward for a job well done. For others, like myself, sissymaid is just 1 of dozens of costumes. I like variety and role playing in my crossdressing.  However, the weekly REGULARITY of sissymaid Sundays is vitally important.

If a wife starts doing this, after a few months, she will wonder why she didn't do it earlier. She no longer has to do housework. Her house is cleaned to her exact standards. Her Sundays are freed up ... she can stay home and be pampered, or go out with her girlfriends to come home to a clean house. The choice is hers. A wife should never do any chores ever.

Initially, no particular outfit is required for the Mistress. But as time goes by, and her dominant side arises, she will want to get into costume as well. Leather, Latex, Satin Blouses, etc. She should start gaining confidence in her new found role, and it should show in her outfits.

As time goes by, the maid outfit should be upgraded accordingly. I have spent hundreds of $$ on fitted, pink, satin maids outfit, with locking collar. There are places that specialize in Sissy Maid uniforms.

In addition to Mistress having specific sissy maid uniform requirements; she should also have PERSONAL requirements from her maid. This may include being clean shaven in the private areas, maybe shaven legs, waist reduction (exercise/diet), manicure/pedicure, maybe clear nail polish, etc. Nobody wants an ugly maid; we want a bombshell.

What is the difference technically from a sissy and a cross dresser

For those who practice Femdom, it can be very honorable to be known as a sissy. They are keen on being subservient to their mistress. They may have a mistress who lives with them, and be very proud to obey their Mistress. Being a sissy is about how they experience it on the inside. They usually know from an early age that they sissies, and do not take offense to the term.

They may put on their frilliest pair of pink silk panties, and immediately feel sissy. But, as soon as they take off those frilly, pink, panties, the mood can change. Sissies love to be identified as sissies, and it is up to them, when and how they are identified. There are many who are married in monogamous relationships. They may like to be recognized as a sissy, because they clean house, and dress like a sissy maid.

For instance, some cross dressers may consider themselves a sissy and are fine with the term. However, it is just a fantasy for them. Maybe they don't even act on it in their life. They could have a wife, family, job, and the whole package. They are not sissies in their everyday life. These men have a fantasy of being a submissive sissy, who may take orders from a mistress.

Many sissies sleep in a chastity belt, with a butt plug in a nightie with panties and bras, to ensure they are in the submissive state as long as possible. Such as my sissy. They will do anything to serve their Mistress. More often than not, sissies are bisexual. My husband wasn't but later grew interested in feeling a real cock in his pussy.

Examples to see if he is open to cross dressing.

Tell him to pick a pair of panties from your drawer he is going to wear for the day, he will more than likely pull out a pair that are frilly or thongs. Don't make a big issue on what he pick just keep a mental note of his choice.

Ask him if he ever tried on a pair of panties? If he admits it. There is your answer, he truly desires to cross dressing. Most men that like to cross dressing are not gay. You can guide them down that path easily but normally not. So don't think you are going to lose him. On the contrary by sharing this fetish it will bring you closer in many aspects. For me one of the main reasons I train them to become a sissy slave is rather simple.

This really depends on your situation how much sissy does he need if you are 24/7 then it's every day if it's on occasion then maybe not. It all depends on your situation.

As said before my husband always has some sort of female clothing on, he always wears panties. He has no male underwear at all. I actually had him burn them after we started our journey into our life together in bdsm. I also like to see him in them now. Such a cute little ass that I like to fuck.

I have also removed all of the soap and we only use feminine products in the shower. It actually made life easier. Below are some training ideas

Sissy training ideas

1. Keep Sissy smooth, not just legs and groin, but arm pits and pussyhole too nobody wants a sissy with a hairy hole

2.Toenails must be kept painted at all times preferably with a toe ring as well. Sissy must be made to wear flip flops or similar

3. Buy your sissy a pretty anklet and make them wear it at all times

4. Take their male underwear and lock them in a box leaving sissy with no option but to wear pretty sissy underwear, this works well when sending your sissy to their workplace

5. Lock them in chastity. Do not discuss release at all.

6. Add a cat bell to the chastity lock, the jingling as they walk adds as a reminder and can lead to awkward explanations

7. If you allow your sissy to cum they must swallow their mess. If they cum they must clean. Is a great rule gross at first but it excites me now.

8. Freeze their cum in an ice cube tray and feed it to them when you decide. Add a gag to ensure they swallow rather than dribble

9. Dress them varying outfits and make sissy pose for pictures.

10. Post the pictures to social media sites to expose sissy, ask followers for suggestions

11. Make sissy pose with signs hung around their neck detailing what a sissy whore they are, or their real name and location

12. Dress your sissy and have them serve you

13. Use zip ties to secure heels to your sissy, make her learn to walk properly in them.

14. Make sissy seal their chastity key in an envelope addressed to you. Make them post it. You can make it harder by missing the post code/zip code. Send it by the slowest class possible

15. Make them post multiple keys each one with a condition attached. Examples: Remain locked and repost the key. Must stand in full view in front/back garden for 10mins to earn release etc

16. Make sissy explain in detail what they want and commit to humiliating ideas, edging as you do so makes their imagination run. Lock them back up until they have satisfied their perverted desires.

17. When sissy comes home from work, have their clothes laid out on the doormat, they must change immediately before greeting you

18. Dress your sissy, ensure they are smooth. Make them sit on a chair in front of a full length mirror. Tie their legs together, arms behind their back, chest strapped tight to the chair. Make sure they can't move. Tell them how helpless they are now and you have total control. Sit astride them, whisper in sissy's ear they need to be made to look more pretty. Gag them. Take out a pair of tweezers and explain how a ladies eyebrows should look....start plucking

19. Tie them to a chair in front of an exposed window. Keep the curtains closed to begin if you want or blindfold your sissy as you tease him explaining how people will see how pathetic they are. Open the curtains and walk away leave them there for a suitable length of time

Chores

My sissy cleans the hose every day and is punished if I find flaws.

It has taken a lot of work and a lot of caning but our house has never been so clean and I am happy finally about having people over. And my sissy has made it possible with some incentive lol.

When your sissy cleans don't be afraid to show disappointment and use corrective actions if they don't meet your standards then discipline him.

It does take time to clean be realistic.

We started with the kitchen then the next day was a quick once over of the kitchen then the dining room the third was a quick once over of the kitchen, dining room and then the bathroom and so on until the house was perfect.

He always does his chores in his maid's outfit.

With a butt plug and high heels.

Exercise

Once he is done he goes and changes into his workout attire. Yoga pants and a sports bra with his plug in. And he does his assigned exercises while I watch him to ensure he is putting his best effort forward. We exercise together he really has lost a lot of weight. Funny I could never get him to exercise until I took him as my slave. Most of my friends even comment on him looking so much better. Those who are in the lifestyle often ask to borrow him. I share only to a select few.

Dinner

Once exercise is over he starts dinner. He has several cooking books we use due to my suggestion and then he will remove his outfit and returns naked where he will eat from a dog bowl while I eat from the table.