Crossdressing — The True And The Torrid.

Fiona Dobson
5 min readSep 4, 2019

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When dressed many of us look for someone to come by and share the intimacy of dressing. As we start our journey this is often a hookup or something like it. After all, anonymity is safe, right? With everything so easily available online, it’s not exactly difficult. And as a crossdresser, having a playmate of either gender is often a fantasy that seems worth pursuing. It can lead to interesting situations — I think we may all have had them. Some are good, and some are horrible.

The problem is, there’s a few social lines being crossed there. Not all of us want to sleep with random

people, of any particular gender. Some of us are revolted by the idea — yeah, really! However, in the excitement of crossdressing, the inhibitions are often released along with so many other boundaries. This is one reason why so many of my good friends have reported feelings of profound guilt and sadness after a liason while dressed.

So, brace yourself, here’s my own take on this. Actually, my crossdressing is very precious to me. Often it’s a private thing. I would only share it with someone extremely close to me that I cared deeply for. I don’t wish to cheapen it with some random scumbag found online. To do so would be to fundamentally misunderstand why I love to crossdress. It would be like taking a beautiful flower and turning it to putrefaction and filth through careless mishandling.

I only chose to share this side of myself with people in which I have a deep sense of connection and love. Yes, it sounds a little out of character, but the truth is that’s why I love it so much. It’s something I have learned to nurture, love and share only with some wonderful and select people.

Contrary to what some people imagine crossdressing to be, I will only participate in it if it is with someone I share deep trust and affection for. And if that trust is broken, it is a tragic thing. The pain that shudders through me on the rare occasions this has happened is a visceral agony that teaches me harshly. I could never enjoy a moment of intimacy in my femme persona with anyone that I didn’t care deeply for and feel profound trust with. They are the dear friends that have made me feel safe, comfortable and even beautiful. I need not fear they would ‘break it’ by doing anything to jeopardise that trust. To cheapen the process is squalid and dirty to me, and something I couldn’t forgive.

So, that pretty much torpedoes the idea that all crossdressers want dick at any cost! I have found the opposite to be true. I can share this side of my life with a few close people, who really get it. They don’t judge me, and they understand that I am opening a precious part of myself to them. They know I don’t do so lightly, and that they are somewhat privileged that it’s something I share with them. If they felt otherwise, I would not want them in my life.

It took me a while to figure this out, but when I did I suddenly found my crossdressing a source of even greater joy, than those first early explorations. It was like a quantum leap forward. The very first time I felt secure enough to enter a bar dressed, along with a dear friend, was such a leap into the abyss that I needed absolute trust in her. Not just a quick drink and ‘let’s do this.’ No. On that day the world changed. If you are at all like me, this kind of trust is not something that comes very easily. It requires you to volunteer yourself to the person you share this with at the most exposed and vulnerable level.

Those first few steps are not something I will ever forget. I could never put myself through such an ordeal with someone that I thought could abuse the trust I placed in them. On a pair of five inch heels, holding the hand of someone I care for, I stepped into a new future that was so uncertain and frightening — and so unfamiliar — and I did so unsteadily with heart pounding. I have seen fear in ways you might be surprised about, and this was more frightening than anything I’d ever done before. I believe the person guiding me knew the scale of those first unsteady steps.

These are not things one can do and enjoy if they are cheapened by distrust and sordid hookups. No, this monumental moment is one that you and a dear friend approach together, frightened and trembling within.

It’s something best done with someone in whom you place deep trust and it becomes a passage into a deeper and more treasured relationship in which both people have shown a sense of connection and bravery that goes beyond simple friendship. It’s nothing less than placing your soul in the hand of the person with whom you have chosen to step those first few terrifying unsteady steps. You’ll know when you find the right person, because you will know you can trust them in anything and any situation, not to hurt you or betray you, intentionally or otherwise.

How can you find someone that won’t abuse that trust? For them to go and do something that breaks that is a loss that could seem cataclysmic, and deeply unkind — so one needs to choose very carefully. However, in choosing someone you really care for, the relationship (which is often outside of marriage) is something that grows more precious and to be treasured over years. Yet, anyone who is worth sharing this experience with is likely aware of the level of trust you are placing with them. It’s hard to find, but it’s there.

These moments of exploration become weigh points that mark the development of the soul. It becomes part of your life that you can hold dear for many years to come. That’s certainly not something you’re going to find on Craigslist, or in some grubby sex club. Such scenes are for those uninterested in acknowledging the vulnerability of being a frail human, or understanding the deep and beautiful joining of two people in trust and shared experience, and the profound connection that results. It’s something you’re going to find deep in your heart with a very special lover who agrees to share space in their soul with you.

As one of my members, I hope you’ll learn to find closeness in connection — not meaningless distance and anonymity in your dressing. The joyously shared timid steps into something beautiful are not something all of us will find. But if you do it’s a truly magnificent gift that with shine within you all your life.

So there it is. Crossdressing — as a part of a closer more loving relationship. Yes, it’s not only possible, it’s probably the most wonderful things you’ll ever experience.

😊

Fiona

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Fiona Dobson
Fiona Dobson

Written by Fiona Dobson

The trans blog you’ll love even if you’ve never tried on your sister’s panties. http://FionaDobson.com

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