How to Advise Our Male Bestie to Crossdress: An MTF Beginner Guide

When Tony Curtis starred alongside Marilyn Monroe in the 1959 film ‘Some Like It Hot’ and won Oscars for the best costume design, all knew crossdressing was here to stay. Fast forward to 2024, our male bestie may also ‘like it hot.’

The irreplaceable moments that friends may bring are something our male bestie may want forever. As our male bestie delves to crossdress, we are their guiding force. Trying out fashion hauls together is a plus, including being safe in public spaces as a crossdresser is also crucial to MTF safety.

Give support for crossdressing. By being an advisory friend, our male bestie can navigate public spaces with accurate discernment for safety. By being an advisory friend, our male best friend may proudly reign in public settings. Keep reading to find out how to advise our cross-dressing male best friend.

The significance of friendship and support

Here are a few reasons why friendship and support is important for our male bestie during crossdressing;

• Happiness and Stress Reduction

Having an ally in our corner as our crossdress will bring more happiness and stress reduction. As friends, we are likely to share our pains and joy. When we laugh together at how hideous that outfit looks, we feel happy sharing fashion idiosyncrasies.

In the same way, we get to appreciate our uniqueness as crossdressing besties. Our best friend will most likely enjoy the happiness and stress reduction that we bring into life as a friend. We will also enjoy the benefits and vice versa.

• Sense of Belonging and Purpose

As our male best friend begins the journey to MTF space, knowing we are with them during this time can create a sense of belonging and purpose. For instance, our best friend will most likely feel the fashion choices chosen are suitable during a crossdresser moment.

Further, when we have friendship and support, our self-esteem increases. When our self-esteem increases, we feel more inclined to participate in our purpose-crossdressing. Nobody enjoys being left out, so being a friend to our male best friend is priceless.

• Education and Growth Perspective

As our male best friend leans into crossdressing more, we also learn more about it. For instance, we know to protect them from bullying or harassment in public spaces. We find ourselves learning about inclusive and diverse laws for Trans people, for instance.

Additionally, the open-mindedness offers a growth perspective. In the future, we get to work with other like-minded individuals. This gives room for growth in our personal and professional life. We are able to tap more into the diversity of the world without judgment of another.

• Emotional Support

We do know that Trans people are more likely to suffer from anxiety and depression compared to the rest of the population. Well, according to the National Health Institute, Trans people need emotional support, which is why bestie support is an integral aspect in crossdressing for our male bestie.

Helping our bestie crossdress by being our male bestie’s personal advisor comes with its therapeutic effect. Our male bestie needs to know that we are there to help them get up when the going gets tough. It is us and our male bestie against the world as our perfect crossdressing duo!

Understanding the difference between crossdressing, gender identity, and sexual orientation

Before we give our bestie nuggets of wisdom on how to crossdress, we help them understand the different terms in this journey.

• Crossdressing

Cross dressing refers to the act of wearing opposite-gender clothes. If our MTF bestie likes wearing fishnet stockings, or lingerie, then it is crossdressing. If we have another female bestie who likes wearing boy suits and any male attire, then it is also crossdressing.

• Gender identity

How our bestie feels, whether as a male, female, both, or neither, is their gender identity. For instance, our male bestie may have their sex assigned at birth as female. However, our bestie may feel like a male. The male identity is their gender identity.

In this case, one’s gender identity may align with the sex identified at birth. For example, if we are assigned male at birth, we can identify as male (MTF). We may also identify as female even if we are assigned male at birth. Gender identity, thus, is a personal affair.

• Sexual Orientation

If one is sexually, emotionally, or romantically attracted to someone, that refers to one’s sexual orientation. For instance, our MTF bestie is sexually attracted to females as a lesbian. If our male bestie is attracted to men, then their sexual orientation is gay. One’s sexual orientation is not dependent on gender.

Tips for Helping with preferred looks and style

We are always eager to help our male bestie uncover their preferred looks and style in the cross-dressing moment by;

• Help Declutter Closet

Scientifically decluttering has been proven to give the room more abundance. As a trusted friend, it is our job to help our bestie sort through the avalanche of clothes. Become a cloth connoisseur. Give honest feedback on what needs to go and what can stay.

It is okay to hang in the emotional moment of reminiscing over beloved pieces that we have to let go of. However, if that handbag is not chic anymore, we let it go. Remove old and not-so-flaunting clothes, and give room for an exciting journey in exploring crossdressing styles.

• Set a style theme

There are loads of MTF aesthetics to pick from. As a result, before choosing, help our bestie set a style intention. What this means is that it helps our male bestie to determine a crossdressing style. Will it be glamorous or haute couture? Minimalistic or flamboyant or bohemian crossdressing attire?

The goal is to ensure that our bestie has style goals or a more successful crossdresser transition. Setting themes helps us save time since we already know which style ticks our fancy and which does not.

• Create an Inspiration Style Board

An inspirational style board is a board that showcases outfits, color palettes, patterns and textures theme in the style. Help our bestie crossdress using this board which can be digitally made or manually.

These are meant to spark our style imagination. Additionally, style boards help our bestie steer back in the direction of our crossdress-styling goals.

• Provide Help with Style Research on the Latest Trend

We want our bestie to stand out and feel effortlessly chic in the crossdress event. Hence, take this time to check out the latest runway wear, magazine trends, and influencer-trending crossdressing styles.

Compile our style research into broad categories of color, statement pieces, silhouettes, accessories, and fabrics. Our bestie will be a step ahead in crossdressing, all thanks to our fashion research and selections.

• Encourage Crossdress Style Risks

Our best friend needs one of the many things all people need in this life courage to take risks. Crossdressing our bestie by encouraging our male bestie to take cross-dressing risks is an important advisory role.

We are not afraid to push our besties beyond comfort zones so we can try bold, edgy, vibrant, and flamboyant crossdress styles.

Create capsule wardrobes the same way we would go for street style. The thrill of crossdressing is in the risk, so tell, egg on, and show our bestie what could possibly be if we simply tried taking fashion risks.

• Regular Wardrobe Assessment

If a best friend does not encourage us to throw away that already worn-out sequin bag, is it really for us? In this case, it is our job to help our male best friend review our wardrobe. Rarely worn pieces can be revamped or donated.

We bring in the bold and trending as we crossdress. Further, an organized closet will inspire both of us to be creative. We are our male best friend crossdressing personal stylist if vintage works well with them, the same way that polka dress can replace the body con dress.

How to Create a Supportive Environment for Our Bestie

A supportive environment for our male best friend who wants to crossdress should look like this;

• Educate others on Trans Interaction

The basis of any supportive environment for anyone is respect in interaction. As a result, at school, educate other willing peers on how to refer to male crossdressers by a pronoun. Educate our and our best friend’s environment on the language that transgender people use.

In this case, consider taking a one-on-one approach or having a small group to share Trans knowledge. Be willing to carefully consider other questions that others ask regarding crossdressing and gender identity.

As such, before divulging personal information about our best friend, such as the birth name, run it by our male bestie first.

• Shun down backhanded compliments or stereotypes.

Supporting our best friend will look like shunning backhanded compliments. This includes shunning my stereotypes about MTF people in general. For instance, comments such as ‘I’d date her even though she is transgender’ are something that our best friend would not like to know.

In any case, quickly shunning down stereotypes about crossdressing creates an environment where our best friend can be their most authentic self. This is because support creates authenticity.

• Be Outspoken

Being outspoken creates a supportive environment for our male best friend. When we speak about transgender rights, it encourages acceptance in spaces such as workplaces or schools.

Being outspoken also means supporting our best friend by calling out Transphobic bullies. This includes making complaints to people in authority regarding Trans bullying.

• Policy Research Efforts

Knowledge is power. Indeed, our best friend will need our knowledge about the laws regarding transgender people in the areas where we live.

Learn about inclusive policies when we use public services such as the washroom, libraries, healthcare, and schools.

The goal is to educate others to know that these laws are in place to protect Trans people, thus providing a much-needed supportive environment.

• Be Ourselves

Being ourselves is the ultimate way to create a supportive environment for our best friend. If we are not a crossdresser, we do not try to crossdress to fit in to please our best friend.

Being ourselves creates a warm environment where our male best friend can be authentic during crossdressing too. Remember, we are the advisors, so we set the pace!

Tips for our friends on how to confidently present themselves in public

These public eye tips will help our best friends present themselves confidently;

• Maintain Eye contact

We do know that maintaining eye contact makes us more resistant to persuasion. This is because the most confident people are not easily persuaded.

The psychological explanation is that maintaining eye contact makes us more connected with the audience as it improves our concentration on the topic.

Eye contact also makes us a good listener. So, the next time we are in public, dear bestie, make eye contact. It is not intimidating, but it is just enough to show others and ourselves that we are present and in tune- the epitome of public confidence.

• Do not Emulate others.

The trick is to develop our style and demeanor in public as a way to let our authenticity shine. It is OK to be inspired by cross-dressing influencers and celebrities. However, we may fall into the comparison trap if we try to emulate mannerisms and dressing choices in public.

Our best friend may have a resting bitch face which others may not like. Our male bestie may want to dress flamboyantly to a party, although it is their beginner crossdressing journey. We allow it because this is the most authentic self, and the public self needs it.

• Re-Write Inner Monologue

So our best friend enters a crowded place and suddenly starts feeling out of fashion. One hack is to pay attention to the things we narrate to ourselves. We advise our male best friends to talk to themselves with respect and compassion about crossdressing.

Bearing in mind the negative phrases and training ourselves to replace these with positive thoughts will ensure that we present ourselves positively.

• Expand Our Fashion Confines

Piece by piece, expanding our comfort in fashion will help us to navigate the public. Start with baby steps. For instance, we can begin with a single bolder piece, like block heels. Slowly, we can expand to include silhouettes for a more daring experience.

Remember that getting confident in public as we crossdress is like a muscle. We have to train it by getting out of our comfort zone. The more we stretch our fashion possibilities as a crossdresser, the more we own the public space confidently.

• Ditch “Flattering” for Authentic

If our style is a loose-fitting dress that does not ‘flatter’ our body shape, we go for it. The idea that our male bestie should wear something flattering at the expense of comfort is dreadful for us as a crossdresser. Remember, our job is not to look picture-perfect in our feminine attire.

Our job is to ‘dress for ourselves.’ After all, what is the point of wearing a flattering backless dress that makes us uncomfortable as we interact with others? True confidence will come from our style, which differs from what flatters our body, especially in public as a crossdresser.

• Be Warm and Cordial

Bestie, remember, the world is our ball, and we are the players. We own the public space that we are in. Speak cordially to acquaintances.

Ask questions and be genuinely interested in what others have to say. Remember, most people love to talk about themselves. Give them the space and enjoy being present.

How to celebrate their journey and milestone

As our male best friend is now comfortable crossdressing celebrate MTF crossdressing journey and milestone by;

• Participate in Crossdressing Competitions

Nothing will remind us two how far we have come like participating in contests. Contests such as best crossdresser legs contests are a fun way to celebrate our crossdressing journey with our best friend. These competitions are fun and will make our two bonds as crossdressers.

• Give back

Give back to the society that has been supportive of us in our crossdressing journey. Giving back opens doors for more cross-dressing opportunities. Donate to crossdressing events together. Be part of advocacy groups for Trans communities.

• Attend Pride Month Events

We crossdress our way into the Trans community by being part of the broader pride march events. Pride month allows us to connect with other diverse individuals in the Trans community. This way, we can support ourselves with pride.

• Celebrate a Friend Day!

Every day is a best friend day. But do we know something else that cements the best friend trope? It is celebrating the National BestFriend Day. Take a day off every year on the 10th of October.

This day we get to celebrate with our male best friend how far we have come. Today we crossdress just the two of us. We have fun in our own right!

Offering Emotional and Mental Support

Offer emotional and mental support to our male bestie in the following ways;

• Understand Our Bestie’s crossdressing identity.

Understanding our best friend’s needs as we crossdress means that we show the utmost respect for our friend’s personhood. Showing respect may look like not assuming we know our male best friend’s every need.

Instead, it should include asking them how to support this journey. We help our male best friend find out where we lie on the spectrum. This can be as a transgender person, as a cisgender, or as a non-binary.

• Respect Pronouns

Our male best friend needs to feel their identity is valid. As a result, it would be an insult to refer to our male bestie, who is crossdressing as a masculine pronoun. Our aim should be to make them feel emotionally supported in their identity.

Call and refer to our male bestie with the proper pronoun and watch them beam with a smile. Always remember that our best friend may use different pronouns during the transition. As a result, being on board is a way to provide emotional support.

• A haven to crossdress

Considering that a good number of crossdressers remain closeted, it can be relieving for our male best friend to have a place to stay and crossdress. Giving someone privacy from the prying eyes of judgemental people during crossdresser is a thoughtful gesture.

Strategies for dealing with potential challenges or adverse reactions

Even as our male best friend has our back, we may have to navigate murky waters of adverse responses by;

• Keeping a low profile as a camouflage

Appearance is the ticketway to public access. Hence, our male best friend should strive to blend in instead of being overtly crossdressing.

Remember that we are just getting started, best friend; hence, crossdress with age-appropriate clothing. This includes cloth length, fit, and accessories.

Avoid overly revealing clothes unless we are in a secure and safe place free of harassment. Keeping a low profile also means walking confidently.

Burying our face in our phone makes our male bestie a potential prey-never a good look.

• Nighttime Walks Could Use Some Company

Danger lurks in the night, and as a beginner crossdresser and best friend, we are not an exception. If our male bestie needs to walk at night, have some company.

Also, walk where our male bestie can see other people. Use our environment to check what’s happening behind or beside us.

Use window stores or car reflections to watch out for reflections of anyone acting suspiciously behind or beside our male bestie.

If we suspect someone might be following, confidently cross the street and change direction. If someone is following us, contact a friend or emergency police.

• Walk in Well-Lit areas.

Though not to demonize the dark, dear best friend, a well-light public area is our arsenal as a crossdresser. Walk on well, lit streets. The key is to always pay attention to our surroundings. Look out for hidden cars or people in dark areas and avoid these areas. We are better off safe than sorry.

• Emergency Exits and Routes

If we are in a bar or club, be aware of exits and emergency exits. Being aware of our surroundings means avoiding being excessively intoxicated with alcohol, as it can hinder our nervous system response to a threat as a crossdresser.

When in the club, look out for what we consume. Never leave our drink unattended. Remember, if someone feels off, chances are something is off, and it is best to move to the nearest group or security.

• Own an alert weaponry.

Yes, at this moment in time, we are our own whistle-blowers. When alone and feeling unsafe, a whistle is a way to alert others in our vicinity that something is off. If we think we are in danger, we blow our whistle as loud as we can to attract help.

A pepper spray is another essential weapon to deter ill-intentioned people towards our male bestie. We always check with our state laws on weapon use in public.

Conclusion

We know how it goes: If we cannot help ourselves, help another person. Our solution may be right there. That is why male besties are a must in 2024 during crossdressing. Being the beacon of light and hope for happiness, happiness, company, and a sense of belonging are things our male best friend needs during crossdressing.

We will be surprised by how authentic and confident our best friend is in crossdressing the public with our advisory information. Always ensure your bestie’s safety by keeping in touch as often as possible. We want our bestie to shine during crossdressing sessions, fails, and successes, so we bring ourselves boldly to the task and lift a hand.