Admit it; you like the feel of silk on you. When no one is looking do you like to dress?
Crossdressing

In this blog post, I will be writing from first-hand experiences in Cross Dressing. This will be from my personal journey and my thoughts on the topics below.

1. What is Cross dressing?

Transvestic fetishism more commonly known as Crossdressing is associated with an intense sexual arousal from wearing clothes belonging to the opposite sex. That’s it!

For example, the most common way this process starts is by the boyfriend or husband putting on the wife or girlfriend’s panties. Does this mean you are a Cross Dresser or into crossdressing? absolutely not, but as the desire intensifies and you continue further down that road you tend to cross into that world.

Going from wearing your wife’s panties and you and her thinking it’s very hot and arousing to secretly wearing her bra, dresses, makeup, perfume, etc can be something completely different and even more arousing.

Transgender Community
Create or join a Crossdressing group on WOK

Why Men Love To Cross Dress

Men choose to cross-dress for a handful of reasons. But we have laid out the top 10 reasons for this. Below are just some reasons one might be into it.

  1. Being born with a Gender Dysphoria
    This is when someone has a mismatch between their gender identity and their biological identity.

  2. They are in love with the other gender
    Men will often wear their spouse’s garments when they are not around and this carries over to the excitement he has during sex with her.

  3. Sexual Arousal
    Some will see cross-dressing as a way to express themselves. Knowing they will get an erection when dressing up as a woman is a huge turn-on to the men who do it. Also, the idea of being female in appearance is seen as a turn-on by men who enjoy this hobby.

    Men who cross-dress will oftentimes find it as a way to feel sexy. This is something that is never achieved when dressed as a man because men never say, gee, I feel sexy in my jeans today. In order for a man to feel sexy, he would have to dress as a woman.

  4. Gender Identity Expression
    Gender forever has been Man or Woman and that’s it.

  5. Relaxation
    For many, the process of dressing as a woman relieves stress, anxiety, and even depression. In a way, it can be seen as a treatment for some who are open to it.

  6. The fantasy/idealization of being a women
    Oftentimes dressing as a woman will make you feel like a woman. It will put you in touch with your feminine side. Yes, even men have a feminine side.

  7. To make your spouse happy
    Some women get very turned on by the though of feminizing their spouse even if just for play. If your wife gets really turned on by the idea, then you are more likely to do it in front of her.

  8. Testing the waters as a women
    Every person who has transitioned either from MTW or WTM have dressed up to see how they would feel. You want to know how a bra and panties would feel and if you would like it or not. This often involves changing things in your wardrobe.

    It might start with tossing all your underwear and replacing it with nothing but panties. This is a baby step but something you can wear out and no one would notice. The next steps for most is breasts development thoughts.

Woman Who Loves Cross dressers

So why is it that some women are so attracted to cross-dressers?

Well you just might be surprised at how many women seek to have a relationship with a male who is into crossdressing.

In a survey of over 300 women who were into it we got all kinds of responses but we did notice a trend in the top reasons most women were into having a partner who was open to it.



Here are just a few of the top responses we got.

  • They like that their spouse is very unique
  • They like the fact that their spouse is conscious about what he wears
  • They like that their spouse sees how hard being a woman is
  • The men abandoned their aggressive behavior when dressed up
  • The men are more loyal to their spouse
  • The men are non-threatening

It’s true most women don’t want a spouse who cross-dresses but there is a significant amount of women who accept it and even a percentage of women who demand it. These women, have had this type of relationship in the past and find it very exciting and created a new level of attraction for their spouse.

Women also see this as a win-win. For one they get a new level of attraction to their spouse and another studies have shown that men who are into crossdressing.


The 2nd win is they have a spouse who is as much into it as they are 70x less likely to cheat on their wife vs relationships where men don’t crossdress or do and are afraid to tell their spouse about it.

Tips and Tricks for Cross Dressers

(or anyone wanting to appear more Femme)

A lot of CDs follow me and I see some struggling to put outfits together, style their hair, choose wigs that are flattering or pick the right accessories or shoes to match outfits.

This is for anyone trying to appear more femme presenting. CDs, sissies, Trans, non binary, gender fluid. All are welcome. I just notice these issues most with CDs, and my followers seem to be predominantly CDs.

1. Pick a theme.
If you were going to a costume party and you loved firefighters, superheroes, princesses and animals, you probably wouldn’t wear a costume that consisted of you wearing a super hero mask and cape with a princess dress, over top of an animal onesie and wearing a firefighter helmet and carrying an axe as a prop…would you?

Maybe some of you would, but most of you would pick one of them or maybe two and run with it, because doing them all at once would be confusing and chaotic. So if you like neon colors, animal print, fishnets, hooker boots or heels, bows, etc, don’t add them all together just because they are all your favorite things. Pick something and put together a cohesive outfit.

One of the biggest mistakes I see CDs doing is trying to throw an outfit together of all their favorite items of clothing or accessories and none of them look good together. They may all be great articles of clothing or accessories but they probably don’t all work together.

Less is more, especially if your goal is to pass in public. (I know not everyone’s goal is to pass though.) Otherwise you look like a 5 year old girl that just pulled out her favorite things from her mom’s closet and threw them all together. Absolutely nothing wrong with that look if you just want to be noticed, then you do you.

2. Less it more, when it comes to makeup.
I’m not a huge fan of makeup in general, so take my opinion with a grain of salt, but I think less is more. You know how you can tell a girl is super young when she wears way too much makeup trying to look older? Well the same is true with CDs. I think they wear way too much makeup trying to look feminine, but in the process look more obviously not feminine or a bit clown like. Less is more.

I see a lot of Cross Dressers that wear very outdated makeup as well. Maybe you grew up in the 80s and always wanted to look more feminine, but now it’s 2023 and your neon blue eye shadow, and hot pink lipstick is not only making you look much older than you want to look, but very outdated and you are drawing a lot more unwanted attention to yourself than you had hoped for. Go on instagram and see what the current makeup trends are. They change constantly. Or stick with a more neutral classic look.

Another issue is poor application. If you don’t know what you are doing when it comes to applying makeup, you are in luck. There are a million different tutorial videos online to show you how to do it, or you can ask a trusted friend or family member to help you out.

If you are comfortable enough doing so, I highly recommend getting a professional to give you a makeover at a makeup counter in a department store or at a store like Mac, Sephora or Ulta. They can show you how to properly apply makeup and make recommendations for you that work well with your skin tone.

3. Know what colors work well with your skin tone.
This will help you pick makeup, jewelry and clothing colors that will compliment your skin tone rather than clash with it. It will make it easier for you to find a flattering wardrobe.

Here’s an article to help you figure out if your skin is cool, warm or neutral and which colors work best for you.
https://www.wikihow.com/Choose-Your-Best-Clothing-Colors

4. Fit is more important than style.
Buy clothing that fits you well and compliments your figure. Trends in clothing come and go, but they don’t always flatter every figure. You should emphasize your best features and you can camouflage your trouble areas.

Get familiar with what styles look good on you and what don’t. You are better off sticking to classic styles that flatter your figure and that you feel comfortable and confident in rather than chasing trends that don’t fit or flatter your figure.

If you have a tiny waist, throw on a belt with a boxy dress to give yourself more of an hourglass shape. If you have long lean legs, rock those skirts or shorts that show them off. If you have a nice booty, wear something form fitting that highlights it.

Here you can figure out what body shape you have and how best to dress for your body shape. https://gabriellearruda.com/how-to-dress-better-female-body-shape/

A-Z Primer for Transvesties & Crossdressers

A few years ago I worked with my sub-husband, previously a life-long transvestite, on several sections of his website, The piece below is one of those sections. It is partly helpful, partly humorous. Should any wiseass comment that it is anti-TV/CD/TS, let me tell you that the website containing it has had over 700,000 hits and not a single complaint. Most find it hilarious in places. I hope you do too. Here it is:-

ACCEPTANCE
is the holy grail for all transvestites. Every man who dresses as a woman, whether or not he is a genuine transvestite, has a compulsion to be accepted by the world “for what he is.” He has no need to worry – if he takes time and trouble with his appearance, then he will often – not always – be accepted as a woman; or at least afforded a certain degree of doubt.

Conversely, if he looks like a ridiculous pantomime dame, he will definitely be accepted by people as just that. Either way, there is a definite compulsion amongst transvestites to brave the outside World in their new persona. The best advice is to suppress that compulsion until they are certain they are ready to be seen in public.

ATTRACTION
like beauty, is in the eye of the beholder. Many a plain or ugly person has been considered beautiful by at least one person in their life. Generally, heterosexuals find members of the opposite sex attractive, whilst homosexuals find members of their own sex attractive.

So whom do transvestites find attractive? The answer is they themselves! No matter what they look like, transvestites subconsciously try to look like the sort of women they find most attractive, and therefore wish to emulate in appearance. Perhaps that is why many transvestites adopt the slutty look; an echo of the paradoxical heterosexual desire to date sluts but eventually marry a virgin.

BIRDS-NEST
term given to a wig badly-worn by a transvestite. Often, an aspiring transvestite believes all he has to do to look like a woman is plant a cheap wig on his – often balding – head. The result is a “birds-nest” where the wig is perched on the top of the head, invariably with a parting, leaving the face below looking like an inverted egg. Definitely a practice to be avoided!

BRICKLAYER-IN-A-DRESS
is a term used to describe a man who thinks he is a transvestite solely by virtue of his putting-on one of his wife’s dresses – or worse, one of her nighties. He then takes a photo of himself in what he considers to be an alluring pose and facial expression invariably composed of pursed lips, from which anyone viewing the photo wisely averts their gaze, preferring rather to conjure-up images of the rain-forest as suggested by the aspiring transvestite’s copious growth of chest-hair.

BUM-PADS
these are hilarious, but are surprisingly bought by quite a few transvestites. They are marketed by the specialist transvestite-supply companies as a means of acquiring a female rounded-buttock look. In actuality, they make the transvestite look like a grotesque pantomime dame. Transvestites would do well to remember that the women they seek to emulate in appearance come in all shapes and sizes, as do their bottoms. The sole use for bum-pads is to turn one upside down and sit on it when you have piles.

CROSS-DRESSING
is a term mostly used by Americans to describe what the rest of the world calls transvestism. The normal use of the word “transvestite” relates to a person who dresses fully as a woman, and “cross-dresser” to a fetishistic person who wears articles of women’s clothing such as underwear.

In the U.S. the meaning of the terms are reversed, which makes it easy to see how confusion can arise. Having said that, many American terms and expressions have meanings opposite to the English ones, and so this particular linguistic anomaly is not that unusual.

DRAG
is a name for clothing of the opposite sex, as worn by a transgendered person. For male to female person, it usually involves dresses, skirts, tops, stockings and underwear. Unfortunately, many aspiring transvestites forget that dressing in drag does not in itself make them a transvestite: they have to do whatever they can to actually make themselves at least look female – if not feminine – by the selection of a suitable wig and by acquiring basic make-up skills.

DRAG QUEENS
are usually not transvestites, but homosexuals who dress as women for a living. Rather than emulate women, they take pains to parody them. Ironically, many women find drag-queens very entertaining, not realising that they as women are being viciously parodied by these drag queens who by virtue of their homosexuality feel nothing but contempt and distaste for women. As may be seen: an entirely opposite approach to women than that of genuine transvestites.

ERECTIONS
definitely something that most transvestites want to hide when they’re in drag. Some use tape to secure their genitals between their legs, but a far better way is to wear tight panties and foundation garments. This will usually prevent the transvestite resembling a woman with a tent-pole.

FANTASY
For many, transvestism is a fantasy – a fantasy of feminity. For these people, it will always remain as a sexual quirk. Transvestism is actually a reality – a very strong reality. Those who only feel the need to dress as a woman periodically, in order to obtain sexual satisfaction, are not real transvestites.

Okay – no harm done – good luck to them. But to be a real transvestite, one has to look and feel the part in everyday life. One has to adopt the persona, or alternatively, be adopted by it.

FEMININITY
is a concept largely unknown to many transvestites. It is a common misconception that all one has to do to emulate a woman is to dress as one. The result is a bizarre amalgam of quasi-female appearance and male facial expressions and body posture. No-one seems to tell transvestites that they not only have to look female, they also have to act in a feminine way.

GENDER DISPHORIA
is a much-abused term. It relates to people who feel that they are born in the wrong body. Although there are females who feel this, more often than not it is felt by males. It is true that there are a small number of people to whom this may apply, and gender-reassignment surgery is appropriate.

Unfortunately however, a great number of men who put on one of their wife’s dresses and buy a cheap wig convince themselves that they “were born in the wrong body.” Wrong They are just fetishists who use the concept of gender disphoria in order to justify aberrant behaviour. You can read more on the signs of Gender Disphoria by clicking here.

GENDER REASSIGNMENT SURGERY
is the technical name for having a sex-change. There are only two valid reasons for having this medical procedure. One is that the person genuinely feels that they were born in the wrong body. The other is that they want to be a woman so much, usually for passive sexual purposes, that it presents itself as an option.

For either of these, the results can be very rewarding. The downside is that the side-effects of the hormones needed to partly facilitate a sex-change have the unwelcome result of shortening the life span. Therefore many questions need to be asked by the prospective changer, so that a fully-informed decision can be reached.

HETEROSEXUALITY or HOMOSEXUALITY
Often it is asked whether transvestites are heterosexual or homosexual. Transvestites and transvestite groups spring into defensive mode, and declare that – although they like dressing as women – they are really heterosexual, without a homosexual thought in their heads.

Not necessarily so. If one dresses as a woman, then it follows that the normal, albeit restrained, aggressiveness needed to acquire and maintain an erection when making love to a woman, is absent. The two feelings – that of passive femininity and that of masculinity – cannot exist side-by-side. It follows therefore, that many transvestites are not heterosexual; they are homosexual, or at the very least – bisexual.

HOLD-UPS
are hold-up stockings. These are much better than tights and less trouble than suspenders and stockings. They give the right look, and also leave the transvestite ready for sex when needed, without having to pull off tights.

HUMOUR
it is absolutely essential for a transvestite to have a sense of humour, and above all to have the ability to laugh at herself. It will help her keep her feet on the ground, and to retain a sense of reality which will enable her to make informed decisions about her activities when dressed as a woman.

Many occasions will occur when the make-up turns-out wrong, and the end result is more like Coco the Clown rather than a woman. It is at times like these that a transvestite must be able to laugh at herself.

INSANITY
is a transvestite in full-drag, but whose make-up leaves a lot to be desired, going to a football match and coming-on to a bunch of drunken supporters – especially the losing team. Definitely something to be avoided.

JOBS
for transvestites who insist on wearing drag to work, are few and far between. Many employers are tolerant of the peccadilloes of their staff, but the distracting element of a fork-lift driver in drag is not conducive to peaceful staff relations.

KNICKERS
are essential wearing for transvestites, preferably the tighter the better. Most women’s panties are insubstantial things, so a better alternative is bikini-bottoms as these tend to be tighter and hold the genitals in better.

LIGHTING
is a crucial aspect of transvestism. Few transvestites are in their best light in daylight. Perhaps for that reason some consider themselves creatures of the night. The general rule is that the dimmer the light, the more realistic – or, more correctly, the less unrealistic – one is. Indeed, lighting, or lack of it, is a transvestite’s best friend.

MAKE-UP
is the bane of transvestites’ lives, as the struggle to find just the right sort to mask one’s male features is an arduous one. Often, it is better to take make-up lessons from an expert, who can suggest various alternatives for the individual’s complexion.

NAKEDNESS
literally strips away all the hard-work a transvestite has put into looking like a female. Ironically however, most men who use transvestites prefer them to be naked except for wigs and stockings when they have sex with them.

OLIVE OIL
is a must for transvestites who are desirous of changing their voice to more closely resemble a female one. Women’s voices are softer, with fewer harsh resonances than men. Swallowing a tablespoon of olive oil just prior to talking has the effect of diminishing the harsher resonances and also making the voice much smoother. Try it out – it may taste horrible, but it does work. If the taste is too harsh, add a squirt of lemon juice.

ORAL SEX
is something that transvestites – like men or women – do, or don’t do. The reason it deserves a mention is that a few fundamental issues need to be addressed before doing it for the first time. Firstly, the risk of infection has to be born in mind, although strictly speaking there is far less risk with oral sex than with penetrative sex.

If you’re worried, there are a range of flavoured condoms on the market. A good flavour is banana, although strawberry is a close second. Avoid Lime – it will make you gag. Secondly, whatever you do – don’t bite. Imagine what it feels like if some idiot bites you down there. Ouch! So if you bite someone, you can’t be surprised if they give you a slap.

PENETRATIVE SEX
As to the wisdom of penetrative sex, although anal penetration is the only option open to a transvestite, it is well to remember that it hurts – a lot. If you’re masochistic, okay. If you’re not, decide whether the role-fulfilment that being penetrated affords you, is worth the pain and – in some cases – worth the anal rips that can occur.

QUICK-CHANGE
The art of quick change is essential for transvestites who are likely to have visitors turning up when they are in drag. Having ready a track-suit to slip into in a hurry is a good idea. For the make-up, cleansing wipes or wet-wipes are very good in removing make-up in a hurry. But make sure you check yourself in the mirror before answering the door.

RAPE
is a very real aspect of transvestism, when one engages in meeting men for sex. Only a very small percentage of women victims report rape – a far lesser percentage of transvestites report when they have been raped, out of fear of being exposed to friends and family.

RUBBERS
in these days of virulent sexual diseases are essential if a transvestite allows men to have sex with them. If you don’t care, that is your choice, but be sure to inform the man you’re with at the time, so that he can make an informed decision for himself as to whether or not to have sex with you.

SUBMISSION
is a big part of a transvestite’s persona. The main reason a transvestite wants to dress as a woman is so that he can have passive sex with men. The submissive aspect often doesn’t stop there – it stretches to allowing men to do anything to them, because only in that way can they feel fulfilled in the passive female role they have embraced.

TRANSSEXUAL
someone who feels compelled to turn into a woman – a brave step, for which much courage is needed, considering the risk to general health in later life. Many men are genuinely transsexual, and really do need to change sex for their mental and emotional well-being. There are a great many, however, who want gender reassignment surgery solely in order to indulge their passive sexual predilections.

TRANSVESTITE
a person who is more comfortable when dressed as a woman. Normally, men who dress as women retains a firm grasp of reality, realising that he is not an actual woman – although has does have close contact with his feminine side, which transvestism helps him express.

There is nothing wrong with being a transvestite – it is a thing to be proud of. A transvestite regards himself as a canvass, doing whatever he can to turn himself into his idea of a beautiful woman.

ULTIMATE ACCEPTANCE
is when a transvestite can go shopping in a supermarket without attracting a second glance. To achieve this, he has to literally leave his penchant for dressing like a slut at home, and carefully dress-down, donning the ordinary type of clothing that most women wear every day. Wearing the absolute minimum of make-up is also a good idea.

VANITY
is a danger for transvestites. It is well to remember that just because one thinks one looks good in the mirror, doesn’t necessarily mean that other people will look on you as just a man in drag.

WANNABES
are usually guys who have read somewhere the phrase “born in the wrong body” and adopt it as their own. Essentially, they are just sad individuals who are incapable of sustaining a normal relationship, and who identify themselves with transgender issues whilst doing so behind their wife’s back.

‘X’
marks the spot. Just as women do, transvestites have facial imperfections. These, they try to cover-up with excessive make-up, which leads to totally the wrong effect. A much better alternative is to use concealer sticks, and just dab them on the offending spot or smear. They work really well.

YOUTHFUL LOOKS
are what most transvestites try to attain, often by the use of blonde wigs and clothes normally only worn by teenagers. This is not a good idea, as the effect will be totally unrealistic. It is far better for a transvestite to look and dress his actual age. In that way he will pass much more easily. As it happens, most transvestites look far younger when they are in drag than their actual age anyway.

ZESTFULNESS
is often adopted by transvestites when dressed. Whilst this is not harmful in itself, it does tend to detract from the femininity that is the transvestite’s goal. Most real women don’t walk around in a manic zestful state, unless they are on something they shouldn’t be. Sedateness is a much more realistic goal.

Transgender Community
Create or join a Crossdressing group on WOK

Advice for anyone in a relationship with one who crossdresses

Yesterday morning I received this request from an obviously very caring woman:

“I’m inquiring about crossdressers. A very good friend loves to dress up for me & be my pet…. If you could/would give some suggestions that will help me with my partner to get the fullest out of what he so desires I would be very appreciative. Thanks.”

I struggled with how to respond. What to say? Those who crossdress are so different in motivation, goals, and tastes that it’s difficult to provide general suggestions that would be of much value. We’re as different as snowflakes.

But I pondered this a bit, and I realized that based on my experience (thus reflecting my biases) over the years I’ve learned a few basic things that seem to be true for a great many who cross genders. Rather than confine my response to one person, I thought I’d share my thoughts here.

A QUICK ASIDE ABOUT LABELS

First, I’m loath to label anybody a ‘Cross Dresser’ since it implies an identity. Personally, I prefer confining my assumptions to the behavior of an individual (one who cross dresses) rather than their identity.

The reality of human behavior is far more complex than the overly simplistic models and labels most people use to think about the phenomena of crossing genders. The convienent little boxes like ‘TS’, ‘TV’,’CD’, etc. are fine to think about the world in the general, but wholly inadequate to understand anybody in particular.

For example, I consider myself Bi-gender; not a ‘cross dresser’, a state of existence flatly rejected as legitimate by what I call ‘Star Belly Sneetches’ who desperately need to feel special in their own little box… but I digress.

The Tug Of War: “How big is his conflict?”

The first thing to understand is that beneath that curly wig, a tug of war is often occuring between the forces that drive one to dress and the forces that cry out for them to stop. The degree of that conflict impacts their pursuit of happiness, the quality of their relationships, and other aspects of their lives. Anything that diminishes that conflict is a win.

Let’s look at the common forces at work:

Picture a tug of war team; On the left hand side you have ‘sexuality’ and ‘desire’ and on the other team you have ‘Shame and Fear’.

The ‘Left Hand Side’

Holding the rope on the left hand side is…

  • SEXUALITY – The desire to dress is often coupled with sexual desire but it can also be wholly unrelated. In the former case, some degree of fetishism is almost certainly involved. That is, they’re sexually aroused by wearing the articles of clothing or the idea of approximating in appearance their idea of the ideal woman.

    For others, there is little or no sexual arousal; in that case they’re dressing probably has more to do with their gender identity; in that case they’re probably somewhere along the transgender spectrum (i.e. being a woman vs. just dressing like one).

    NOTE Please be aware that the desire to dress cross gender has no necessary correlation to the gender one feels sexual attraction for. That is, just because a guy wants to look like Marilyn Monroe doesn’t mean he’s suddenly going to want to screw Joe DiMaggio.

    It also doesn’t mean he won’t. I have observed that those who fetishize about being a woman (vs. just dressing like one) often also fetishize doing what they imagine women do. I’m probably a little bit along that line because I do get off on the idea of…. umm… pleasuring guys.
  • DEGREE OF DESIRE – Never ask “Why do you feel like this?” The quest to answer the question is both fruitless and moot. It’s fruitless because the desire arises from a place in our psyche that’s inaccessible. The best we can do is confabulate some sort of story to rationalize the behavior that assuages fears and protect the ego.

    It’s moot because like the urge to copulate, it’s simply there and It’s not going away. What’s helpful is to understand the degree of the the need.. Some questions to ask your partner might be, “How often do you feel like dressing?”, “How does it feel when you haven’t dressed in a long time?”

The ‘Right Hand Side’

Holding the rope on the right hand side is…

  • SHAME – Ask if he’s ever purged (discarded his girl stuff) or feels guilty about his dressing. Many who cross dress feel a deep inner conflict with the religious and social norms they feel their dressing violates. Unfortunately for some, the values and beliefs that fuel shame are often so deeply rooted that it can take a lifetime to tame them. The greater the shame, the greater the conflict (and the dysfunction).
  • FEAR – Is he reluctant to publicly purchase the clothes he covets or venture out beyond the confines of where he feels ‘safe’ dressing? Most who cross dress harbor vague but often intense feelings of fear. Fear of being ‘caught at it’, of what others might think, of what others might do, and sometimes even what they might do. Those who cross dress tend to massively overestimate the potential negative reaction and awareness others to their dressing. As a result, they fail to act to realize their potential.

It’s worth noting that a healthy degree of fear isn’t a bad thing. I’ve seen some people so completely abandon their fear that they choices that put themselves at risk (dressing like a hooker and walking down a deserted street).

The Gotchas: stuff to watch out for

  • HIGH Degree of Desire to dress: At the very high end, be wary of being viewed and treated as a fetish delivery system. Don’t hesitate to communicate your limits and desires. Ironically, guys who finally find a partner who accepts their desire to cross dress can drive them away by overly focusing on their fetish. To be frank, they can be pretty selfish. Help him understand what your needs are and help him find a balance.
  • HIGH Degree of Desire coupled with a high degree of Shame – Guys whose inner conflict between these two forces are prone to depression and sudden harsh choices that may surprise and hurt you. They may retreat, react with anger, or suddenly decide this isn’t ‘right’ for them and cut you off from all communication. The bad news is there isn’t much you can do about this other than brace yourself and watch for signs that it may be occurring.

Opportunities

  • HIGH Degree of Fear – Here’s where you can really help somebody whose happiness is constrained by exaggerated fears (note… virtually everyone I’ve ever met who cross dressed has felt some degree of irraiontal fear about their dressing… at least at some point in their life). The only way to overcome fears is to face them; walk through them, and come out on the otherside with the realization that the fear was unfounded or exaggerated.

    Doing this enough extinguishes the fear. Reducing the fear reduces the conflict and improves the quality of your interactions. Work up slowly but if he’s afraid , ‘order’ him to do something simple, like purchase a pair of panties or some other desired object from walmart or (gasp) Victoria’s Secret.

Frankly, this was the catalyst for me. A very caring domme ‘forced’ me to buy some panties at Victoria’s Secrets. I was terrified. She even required that the girl in the store helping me sign a piece of paper that made it clear that the panties were for ME. I must have walked in front of that store a dozen times before I had the guts to go in. After that, I forced myself to buy shoes, makeup, etc. especially when I was scared. The cool thing is that overcoming these fears translates into confidence in many other areas of my life.

Conclusion

Many who cross dress experience some or all of this. I’m in a weird place where I feel

  • No sexual desire to dress (dressing ceased to be a fetish for me long ago).
  • No ‘great need’ to dress – I don’t feel a clawing desire at all. Rather, for me it’s just about expressing my feminine side. What draws me isn’t the dressing but what I enjoy doing when I dress
  • No Shame – Never had any, so never felt this tug (I got off easy)
  • Some Fear – Yeah, there’s still a little. I’m still surprised a little when I’m dining at a restaurant as Jennifer and nobody gives me a second glance. This is still an area where I need to work on.

It’s hard to make any kind of generalizations about the experience of dressing cross gender; our motivations, goals, and needs are very different but by understanding some of the forces commonly at work, you can better equip yourself to work with them to get the most out of your relationship.

I hope this helps!

Useful Links for Cross Dressers

Fake cross dressing breasts – Wear My Boobs
Reddit forum for CD’s – Reddit
Amazon CD shopping – Amazon
Crossdressing porn – Xhamster
CD and Sissy Porn – Tranny
Apply makeup for CD’s – Makeup YouTube

Crossdressing FAQ’s

How common is cross-dressing?

Without counting Halloween, it is estimated that 5-10% of all men have tried cross-dressing at some point.

Where are the most cross-dressers?

In the US it would be San Francisco, outside of America it would be São Paulo, Brazil.

is cross-dressing illegal?

In the United States, there is no laws saying what you can and can’t wear so if you want to dress up, feel free to and enjoy it.

If you cross dress are you gay?

According to a survey, almost 90% of men who cross-dress are straight.

What is a CD?

The term CD stands for Crossdressing.

Author

  • Jessica Fox

    Jessica is a seasoned blog writer with over 15 years of experience living and exploring a diverse range of kinks. Her passion for writing is matched only by her enthusiasm for the lifestyle, which she brings to life through her engaging and insightful content. Jessica's deep understanding and personal involvement in the kink community have made her a respected voice in the field. Her blog offers a unique blend of personal anecdotes, thoughtful commentary, and practical advice, making it a go-to resource for those interested in learning more about the world of kink from someone who has not only observed but also actively participated in its many facets.

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