Falling In Love with a Stranger

The other weekend I went out on a ten-mile hike up one of the nearby mountains north of L.A. It was a beautiful slightly chilly day, perfect for strenuous hiking.

Unlike my friend Jeanne, I sweat way too much to go hiking in girl mode, so I was just in boring ol’ boy mode on the trail. As I was starting out, I noticed a young woman, maybe 30 years old, who was hiking alone and wearing this cute dusky peach workout top that was snug and close fitting. I didn’t want to be the creepy guy and stare at her but from the moment I saw her she made an impression. First off, her cute outfit, with her workout top and leggings immediately awakened my fetishism. I wanted so badly to check out what she was wearing but made an effort not to. “Don’t be like that. You’re not here to stare!”

And secondly, she also completely awakened my feelings of gender dysphoria. I had that familiar feeling of wondering what her life was like, and wondering what my life would have been like had I been born with a body like hers. What would it be like if I were a young woman wearing my cute workout wear, going about my life in L.A., and going up a mountain on a solo hike. I admit the whole thing does sound a little creepy when I put it down into words like that. But my main concern was not to stare at her or give her any unwanted attention. She was alone minding her own business and wasn’t there to be bothered with my silly inner thoughts and desires.

The funny thing though is that during the next four-hour hike we kept leapfrogging on the trail, and not on purpose. I really wasn’t trying to follow her, but it always seemed we were just a few hundred yards apart, all the way up the mountain. She would pass and then I would pass, and we would say the casual greetings that you say when you’re on a popular trail. Finally, as it was getting cold near the top, she turned back and as she passed said she was calling it a day since she didn’t have any other layers. And then ironically, there she was again thirty minutes later coming up to the summit just as I was starting to descend. She had hooked up with a hiking group that must have told her that she was so close to the top, why turn back? And to add to the comedy of the whole situation, the route down was poorly marked (the trail was a loop), so after a while I ended up having to tag along with the hiking group too just to find my way back down. It was like I couldn’t get away from her!

So maybe I didn’t really fall in love with her, but I sure was aware of her presence, and to me it felt awkward. We’ve all had that experience where you meet someone that you find so attractive that it’s actually distracting. Sometimes it can even be unpleasant in a “sweet suffering” kind of way. It was like, “I just want to do my stupid hike. I don’t want my emotions and desires and my dysphoria to get all worked up!” But that’s what happened. The funny thing is that I’ll probably remember this woman for the rest of my life because the emotional response, and her attractiveness, was so strong. I just hope I wasn’t perceived as the creepy guy on the trail – that would be utterly mortifying. Who knows if I seemed weird or anxious, but all my inner rumination certainly couldn’t have helped!

I’ve certainly seen other people whom I also remember because they were so attractive, mostly women, but also some crossdressers too. I’ve had this experience several times of being at a bar or club and seeing someone whom I don’t have the courage to approach, and then ending up with their image later burned into my memory – some of them I can remember years, even decades, later.

Part of the difficulty in relaxing around a shockingly attractive person – and of course this is very common – is that I’ve often struggled with feelings of unworthiness, that feeling of being somehow flawed or undeserving deep down inside, even though normally I can carry myself quite well and usually make a good impression on people. But inside, there’s that little voice that says, “No, not quite, not you.” It’s an irrational response – probably only made worse by gender dysphoria and fetishism – but it’s so persistent, like a nagging guest who just keeps revisiting again and again.

So that was my day out hiking. Later that evening I still thought about the young woman, and at one point I did say out loud, “I think I just fell in love.” Strange how things work out. I just wanted to go on my hike and get some exercise and see if my heartbeat felt improved since my hospital visit in December (good news, my pulse did feel much better!) So there’s what I was expecting from the day and there’s what I got – another memory of a cute girl to swoon over, and a day or two with my emotions shaken up like a snow globe – all combined with a good workout – not a bad weekend to be honest.

4 thoughts on “Falling In Love with a Stranger”

  1. What a great story. Thank you for sharing. I think many of us have similar experiences of remembering exceptionally attractive people, and to a lesser extent just “normally” attractive people. I still remember meeting you for the first time and somewhat struggling “with feelings of unworthiness, that feeling of being somehow flawed or undeserving deep down inside, even though normally I can carry myself quite well and usually make a good impression on people, probably only made worse by gender dysphoria and fetishism.” ;)

  2. Hi Miki! Thanks so much for the comment – I appreciate it! It’s good to hear from you. I do think that feeling of judging oneself or feeling that we somehow come up short is something that so many of us can relate to. I hope you’ve been doing well :-)

  3. This reminded me of a time many years ago when I was leading a group of editors interviewing candidates for summer internships. We were on our sixth or seventh interview of the day when this beautiful young Hispanic woman comes in. She is wearing a gray business suit with a red silk blouse (a bow, of course) and, because she is slightly on the heavy side, I hear the swish-swish of her girdle as she introduces herself to me. She has long, flip-style brunette hair, doe eyes, cherry-red lips, and chipmunk cheeks. I smile. She beams. We shake hands. I cannot help but watch as she walks to the far end of the table for the interview. I can feel something stirring down below. As she sits and we start the interview, everything in her manner, her smile, and her laugh has me enthralled. By the end of the interview, I am stiff. Everyone else stands to thank her, but as I do, I realize I will reveal an inappropriate bulge. I quickly knock some paperwork on the floor and say “Damn! Excuse me! It was nice to meet you. But I’ve got to…sorry….” I drop to my knees and pick up the papers. Thankfully, one of the other editors escorts her out, then returns. Another editor says: “What do we think of her?” My brain is frozen. I realize I have no clue about her candidacy. “I’d like to hear from everyone else first,” I say. Fortunately, everyone else had detailed opinions. Unfortunately, she did not make the cut.

  4. This is a charming and honest story.

    We all go through life and have feelings towards a woman we’ve crossed paths with, or maybe have seen photos of an extremely convincing crossdresser, but are left with nothing but a memory many years later.

    I married in my mid-40s after a partly itinerant life and with longstanding struggles between my Christian faith, my crossdressing and poor social conditioning in boys’ schools and at home. Providence has allowed a very imperfect man to latterly have both a wife and a child. An unimaginable and difficult route has allowed me now to openly wear (medical) tights and a kilt at home. My private crossdressing has diminished. Although the frisson never seems to go away.

    If finding love with a woman is what you really want, my personal testimony is not to give up on the idea, and to continue to make the effort.

    You could maybe sign-up to that hiking group in boy mode, just in case the woman reappears one day, or in case someone noted her coordinates. Or another nice woman just might come along. It’s a low-pressure group environment in which to interact. (Hoping of course that there are no bears in the mountains where you are).

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