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Interview with Dr. Gwen: A Man’s Journey with Hidden Crossdressing, Secrecy and Anxiety 

It's Saturday, it's Gwen.

This is a fictional interview and has been modified for privacy purposes. It’s a compilation of many discussions with many men over years and formatted for social media consumption.

Dr. Gwen: Welcome, and thank you for being here today. Could you tell me a bit about your experiences with crossdressing and how it has impacted your life? 

Patient: Thank you, Dr. Gwen. I’ve been crossdressing for many years, but I’ve always kept it a secret. It’s something that brings me a lot of joy, but also a lot of anxiety because I can’t share it with anyone, especially my wife. 

Dr. Gwen: That sounds incredibly challenging. How does keeping this secret affect your daily life and relationships?  

Patient: It’s like living a double life. On the outside, I’m fulfilling all the roles expected of me—husband, father, friend—but inside, there’s this part of me that I have to keep hidden. It’s exhausting, constantly worrying about being discovered. It makes it hard to truly connect with others because I’m always holding back. 

Dr. Gwen: I can imagine that would be very isolating. How has this secrecy affected your marriage? 

Patient: It’s definitely taken a toll. Marriage is supposed to be built on trust and openness, but I feel like I’m constantly lying to my wife. It makes me feel guilty and ashamed, and that creates a distance between us. We’re together physically, but emotionally, I feel very alone. 

Dr. Gwen: Society often has rigid views on gender norms. Do you fear judgment from others if they were to find out about your crossdressing? 

Patient: Absolutely. The fear of judgment is huge. I worry about what my wife, family, and friends would think if they knew. This fear stops me from seeking support or expressing my true self, which just reinforces my sense of isolation. 

Dr. Gwen: That must be incredibly tough. In contrast, how do you think a single person with a supportive group of friends might experience loneliness? 

Patient: I think a single person with understanding friends can be more open about who they are. They don’t have to hide, and they can form genuine connections based on acceptance. That kind of support system can really help reduce feelings of loneliness. 

Dr. Gwen: Authentic connections are indeed crucial. How has the need to keep your crossdressing a secret affected your ability to form these connections? 

Patient: It’s been really hard. My interactions are always filtered through the need to maintain my secret. I can’t be fully open with anyone, which means I don’t have those deep, accepting relationships that are so important for emotional well-being. 

Dr. Gwen: It sounds like living this double life takes a significant emotional toll. How has this impacted your mental health? 

Patient: It’s very stressful and anxiety-inducing. The fear of being discovered is always in the back of my mind, even in mundane situations. This constant stress can lead to depression. It’s a deep loneliness that’s different from what a single person with supportive friends might experience. 

Dr. Gwen: Thank you for sharing your story. It’s clear that the loneliness you feel is multifaceted and deeply rooted in the secrecy and societal pressures you face. Is there anything else you’d like to add?  

Patient: Just that I wish more people understood that true companionship and deep connections come from acceptance and authenticity. It’s hard to find that when you’re forced to hide a significant part of who you are. 

Dr. Gwen: Thank you for your openness. Your story highlights the importance of acceptance and the profound impact that living authentically can have on one’s emotional well-being. 

 Dr. Gwen Patrone 

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5 Responses

  1. Gwen,
    Many non-transgender people assume the need to dress is a mental condition , that being the case it possibly could be cured . You raise a very important point once it’s been accepted it’s not a mental illness there is no cure but many of us suffer from mental problems through the total isolation we endure but then could be also apply to people coming to terms with being gay . Also we often overlook the fact that there are almost as many F/M transgender people but I don’t feel they suffer so much from the stigma of crossdressing , I often relate the male situation as wearing a male straightjacket , so much is expected of us to adhere to the male role in society .

    Is it any easier for a single person ? They may not have as many committments but they still need to answer to close family and friends , not forgetting religion which could be the toughest one to crack in some parts of the World .

    Seeking help is often an enormous hurdle to jump because we have to admit so much to oursleves , self denial of what we fear we could be if we seek professional help . Even after that when we may begin to accept labels we still have to convince others of the truth , I truly believe we need to know what makes us tick so we can move forward .

  2. Hi Teresa,
    Such a wonderful and thoughtful reply.
    One that causes me to think and contemplate I love it.

    Being a single crossdresser certainly has less entanglements to consider to be sure and as stated, F2M seems to have less stigma than M2F.

    Gwen

  3. As a crossdresser I know that we have problems with family, friends and society. But nothing beats the ecstasy of feeling feminine.

    Ever since I put on a pair of panties, I wanted to be a girl. My fondest memory as a teenager was the first time I saw myself in a mirror wearing panties. I had never felt more feminine than I did that day. In fact, I felt like I was a girl. and could do things that girls do.

    Today the feeling of a breeze blowing under my skirt and through my hair is something that heightens my feelings of being a girl who looks and feels feminine.

    Soon I feel that contact with my feminine side will happen when I surrender to a man and accept his masculinity within me.

    And then nothing else matters. I will let myself be carried away like a wave in the sea.

    In Portuguese my native language

    Como crossdresser sei que temos aborrecimentos com a família, amigos e sociedade. Mas nada supera o êxtase de sentir-feminina.

    Desde que coloquei um par de calcinhas, eu queria ser uma garota.
    Minha lembrança mais carinhosa da adolescência foi a primeira vez que me vi em um espelho usando uma calcinha.Eu nunca me senti tão feminina quanto naquele dia.
    Na verdade, eu me senti como se fosse uma garota. e poderia fazer coisas que as garotas fazem.

    Hoje a sensação de uma brisa soprando debaixo da minha saia e através do meu cabelo é algo que aumenta meus sentimentos de ser uma garota de aparência e sentimento feminino.

    Em breve sinto que o contato com o meu lado feminino vai acontecer quando me entregar a um homem e aceitar sua masculinidade dentro de mim.

    E aí nada mais importa. Vou me deixar levar como uma onda no mar.

    tammilee.tillison@gmail.com

  4. Hi Dr. Gwen, I really love what you post here. I am single still but otherwise could very easily be the patient described here as all the feelings and questions described here are things I often experience too, so I can just imagine myself in the shoes of the patient. It must be something most transgender and crossdressing people go through, wishing to live authentically. We’re lucky to have you as the Kandi’s land physician.

  5. Gwen,

    A man, who has a need to wear women’s attire for whatever reason never escapes the “What If?” I have already celebrated 3/4 of a century on this planet. I punched my ticket of life and checked off all those boxes of a model citizens. Yes, even a Purple Heart w.Oak Leaf Cluster. I realize I am not immortal. Death comes to all. What will happen to the incomplete image people/family have of me, if my “hidden in plain site” stash is discovered? My wife knows I am a cross dresser and has no idea of the amount of garments I have. She can have a heck of a garage sale. But, if she predeceases me, yikes

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