My Crossdressing Journey

I continue to work with AI. It's turned out to be very therapeutic. I use ChatGPT and found it to be very in-tune with crossdressing. We've explored numerous facets and Chat has often given me a voice when I didn't have the words. At times it gave me insight when I lacked vision. Other AI's might be as good, I'm not necessarily promoting ChatGPT.

I thought I would share my journey with you. I'm fairly old now (72) and have traveled along in life with my feminine side since about 5 years old. You might find this interesting as you explore your journey for where you are and where you might go to. Mine is marked with a number of stages I went through. If this helps anyone in any way it's a successful post. Enjoy.

Some of this is based on a behavior model developed by Elliot Saxby. He breaks behavior into four quadrants (Mature Masculine, Mature Feminine, Immature Masculine, Immature Feminine). We all have these four parts in our psyche and we move between them at various time. There is more information on this framework at the bottom of this post. I don't want to get into it much at this point. It's pretty simple and the quadrants follow their names, Immature Masculine behaves kind of how you think it would. As does Mature Feminine. This is not gender based (male/femaie), only behavior. Enough said.

My Crossdressing Journey: A Story Through the Quadrants

Stage 1 - Not Knowing (Immature by Necessity)
In the beginning, I didn't know what this was. The desire was strong, but I had no words, no framework, no understanding. Crossdressers are often criticized for not telling their wives early on, but the truth is: we don't even understand it ourselves in those early years.

My thoughts were confusion: Why do I feel this way? What does it mean?
My feelings were raw: curiosity, thrill, but also guilt and shame.
My behaviors were immature because they were undeveloped, grabbing at lingerie for short bursts of thrill, then pushing for moments of expression without really knowing why.

Quadrant resonance: Immature Feminine (thrill, compulsion) mixed with Immature Masculine (pushing, secrecy). It wasn't malice. it was immaturity born of not knowing.

Stage 2 - Expansion and Boldness (Here I am, deal with it)
Once I discovered what presentation could do, it was like a dam burst. Something inside me was pushing hard in this direction. Makeup, wigs, dresses, shoes, it all came together in weeks. I realized I could transform my appearance, and I had to test it in the world. I was pushing hard to see if the world would accept me. To a large extent it did, very little push back or negative interaction with the world. Lot's of positive interaction.

My thinking: Here I am. Deal with it.
My feeling: exhilaration, urgency, almost defiance.
My behaviors: pushing hard with my wife, claiming time, claiming space, insisting on my crossdressing whether she was comfortable or not. With the world, I stepped out boldly: malls, pride events, bars, Halloween. And the world surprised me. It said, in its own way: It's okay. You're fine.

Quadrant resonance: A clash of Immature Masculine (forceful, insistent) and Immature Feminine (thrill-driven, urgent) but with the seed of Mature Masculine (authenticity, testing reality). It was messy, but it was movement.

Stage 3 - Strain and Loyalty (Relational Anchor)
This stage was challenging for us. My wife was uncomfortable with much of what I was doing. She didn't always want to see it, didn't always agree with my choices. And yet she stayed engaged.

Sometimes she even accompanied me out in public, even when it was hard. She loved me enough to endure the strain. I fought for my crossdressing; she fought for our marriage.

Looking back, I can see how much I leaned on her strength in this stage. My drive for authenticity could have become reckless. Her loyalty grounded me even when I was still immature in how I handled it.

Quadrant resonance: My energy was still tangled between immaturity and growth. But her love allowed me to begin moving toward Mature Masculine (stability, responsibility) even before I was fully ready.

Stage 4 - Integration and Shared Intimacy (Maturity)
Today, the energy is different. My wife and I dress together. We talk about clothes, shoes, how to walk in heels. We have dress-up evenings, and we make love in lingerie. The wigs and makeup matter less; the intimacy matters more.
Now, she often chooses when we have our dress-up days. I respect her boundaries about what clothing feels comfortable for her. We shop together, not just for me, but for each other.

This is no longer me claiming space. This is us creating space together. Crossdressing has become a shared experience we co-author from deciding what I wear, to how we play, to where we go. The focus has shifted from self-expression alone to partnership, intimacy, and joy.

The thinking now: This is us. This is intimacy.
The feeling: joy, tenderness, wholeness.
The behaviors: respecting her agency, creating playful rituals together, letting dressing be a natural part of our shared life.

Quadrant resonance: Mature Masculine (respect, steadiness, honoring her) and Mature Feminine (tenderness, play, intimacy) working in balance. This is no longer about escape or thrill. It's about connection and love.

The Saxby Thread

• Immature Masculine → secrecy, force, insistence.
• Immature Feminine → thrill, compulsion, defiance.
• Mature Masculine → authenticity, stability, boundaries, responsibility.
• Mature Feminine → intimacy, tenderness, play, radiance.

My journey has touched every quadrant. Early immaturity wasn't failure, it was a starting point. But the real growth has been moving toward maturity in both masculine and feminine energies: steadiness with openness, honesty with tenderness.

The Outcome
Crossdressing began as a mystery, then a thrill, then a defiant act of self-assertion. Now it has become intimacy, not just mine, but ours. My wife and I are still learning, still finding rhythm, but we've entered a place where dressing is no longer just clothing. It is a language of love, trust, and shared maturity.




A Brief Note on Saxby's Framework
Saxby's model is a way of understanding masculine and feminine energies in both their immature and mature forms.

• Immature Masculine → rigid, secretive, defensive, controlling.
• Immature Feminine → dramatic, thrill-seeking, insecure, manipulative.
• Mature Masculine → steady, honest, protective, accountable.
• Mature Feminine → open, tender, playful, creative, radiant.

It's not about gender roles (male vs. female), but about modes of being that all people carry.

• When we're immature, we act from fear, insecurity, or control.
• When we're mature, we act from wholeness, responsibility, and love.

For crossdressing, this model is helpful because it shows how dressing can show up in different ways:

• As secrecy or thrill when immature.
• As intimacy, authenticity, and connection when mature.

Attachment 347088


Key Insight:
Everyone carries both masculine and feminine energies. The question isn't male or female, it's whether we live from the immature or mature expressions.
For crossdressing:

• Immature quadrants → secrecy, thrill, defensiveness, compulsion.
• Mature quadrants → authenticity, intimacy, tenderness, safety.

I came upon this post a bit late in the day. I will need some time to absorb and contemplate.

Very interesting. Thanks for sharing

I?m not sure that I ever got beyond stage 1

I have two factors I forgot to include. They are critical aspects to my journey and if this story interests you, these are very important to include.

Sorry if you aren't interested in my journey. I'm going to stop updating this now.

Here are the updated Stage 1 and 2.


Stage 1 — Not Knowing (Immature by Necessity)
In the beginning, I didn’t know what this was. The desire was strong, but I had no words, no framework, no understanding. Crossdressers are often criticized for not telling their wives early, but the truth is: we don’t even understand it ourselves in those early years.

During these years, we were raising four children together. My commitment was to keep my dressing hidden from them — and to this day, they still do not know about this part of me. That commitment shaped much of how I managed my crossdressing: always private, always in the shadows.

On top of that, our marriage itself went through profound upheaval. After about 20 years, it ended in divorce. The reasons weren’t about crossdressing — there were other strains in our relationship that led to the collapse. I wanted to reconcile, but at that time my wife wasn’t willing or able. We lived apart for about three years. During that time, we both had other relationships. Mine was ending, and when I was preparing to move to another country, my wife reached out. Against the odds, she decided she wanted to remarry me. It was messy, but we found our way back to each other. That second chance became the ground for everything that followed.

My thoughts then were confusion: “Why do I feel this way? What does it mean?”
My feelings were raw: curiosity, thrill, but also guilt and shame.
My behaviors were immature because they were undeveloped — grabbing at lingerie for short bursts of thrill, then pushing for moments of expression without really knowing why.

Quadrant resonance: Immature Feminine (thrill, compulsion) mixed with Immature Masculine (pushing, secrecy). It wasn’t malice — it was immaturity born of not knowing, shaped by family commitments and the turbulence of our relationship.

Stage 2 — Expansion and Boldness (“Here I am, deal with it”)
Once our children were grown and no longer part of the day-to-day picture, my feminine side felt an incredible freedom and was pushing hard for expression. During the child-rearing years, I had kept everything carefully hidden, locked away in private moments. But when that responsibility eased, it was as if a dam broke.

I wanted to see how well I could present my feminine self to the world. Makeup lessons, wigs, proper women’s clothing — skirts, blouses, dresses, heels — all became central. I no longer wanted just lingerie in the shadows; I wanted to learn presentation, to step out, to be seen.

So I did. I went to the mall. I attended pride events, supportive bars, and of course Halloween. What I discovered surprised me: there was no mob with torches and pitchforks. The world was largely accepting. People either treated me kindly or simply went about their day. That experience was liberating.

My thinking: “Here I am. Deal with it.”
My feeling: exhilaration, urgency, almost defiance.
My behaviors: pushing hard with my wife — claiming time, claiming space, insisting on my crossdressing whether she was comfortable or not. But also, boldly testing myself in public. And the world, in its own quiet way, said: “It’s okay. You’re fine.”

Quadrant resonance: A clash of Immature Masculine (forceful, insistent) and Immature Feminine (thrill-driven, urgent) — but carrying the seed of Mature Masculine (authenticity, testing reality). It was messy, but it was movement.