Who knows? Who suspects? Plus my only outing with my wife.

I have time for one more entry before heading home for some “vacation” (yeah right. The honey-do-list is still very long..haha). It’s a bit longer than normal, but time it was written.

So, who knows?

My wife, the love of my life knows. My sister knows, or at least she knew when we were younger. I don’t know if she thinks I have grown out of it or what. It’s not something we have ever talked about since we grew up. My mom and dad kind of knew. And that’s who knows. Who suspects will follow later.

While I was attending technical college, spending only some weekends and holidays at home, my mom found some articles of girls’ underwear that I had forgotten about between my mattress and the box spring. This came to light as my dad asked me during a drive back from the city what was up. Was I some kind of a panty pincher? Well, as I mentioned in an earlier post, I had been able to do some research and was able to explain, as best I could and understood, that I was a crossdresser. Strangely, I don’t remember the conversation go much further than that. It wasn’t until a couple of years later that they would see my dressed (for the first and last time) on a Halloween evening when I got up the nerve to go pick-up my mom from work. My dad and sister were not yet home when I set out wearing my light grey pinstripe suit with my brunette wig. I didn’t get out of the car, just pulled up outside her work. My mom was surprised but not put off. When we arrived home, dad and sis had also just arrived. Dad was also surprised but complimentary where as my sister was a bit uncomfortable with it. After an hour or so I got changed. I don’t really remember much of any conversation and it was left at that. Due to an overseas six month excursion (that would ultimately lasted two and a half years) I was unable to capitalize on this ice breaker.

We all know we should not have secrets with our significant others. I believe I was fortunate enough to have read the advise that is so often given (to tell your SO) before I met my wife.  I met her shortly after moving down east. We hit it off on our first date. As things got more serious, I knew she was the one I wanted to spend the rest of my life with. I could not keep something like this from her. One evening, I told her that there was something I needed to tell her, that she might not understand, that she may be repulsed by it, but I had to tell her and that I risked losing her in doing so. I was getting so emotional about it, I was near tears. I loved her so much. But this was a part of me and had been since I was little, and was not going to go away. She needed to know. So I just said it, “I’m a crossdresser, I sometimes like to wear the clothes of the opposite sex”. It was done. Out in the open. But rather than being critical, she comforted me and asked some questions. After some time of explaining my past, she asked if I had any pictures. I tentatively showed her a number that I had readily available (older ones that are now scanned and on my flickr page). At first, she could not believe they were of me but was quite impressed. I think it was about two weeks later, after we had talked some more that she asked to see me dressed. I don’t know how I got my make-up on as I was shaking so much. I don’t remember what I wore first, that’s too bad. I changed into many an outfit that evening; she even offered some tips for my hair and make-up. After she moved in, we had a couple of “girls” nights and I even spent a Halloween night dressed as a Star Trek woman, handing out candy to the kids.

One and only outing with my wife.

The one and only time we went out with me dressed was when my wife was invited to a convention in a nearby city (for a whole weekend, links to photos included). After checking in at the hotel, I got changed into my grey skirt outfit and  we went for a walk through the adjoining mall. I normally walk very fast, but this time I was having difficulty keeping up with my wife while wearing my heals. We browsed through a few stores and then walked around a couple of blocks. We even checked out a restaurant that we would return to later that evening. What a fantastic feeling. After changing into something a bit more alluring, we enjoyed a wonderful meal served by a waiter who didn’t show any signs of having read me. We then retired to the hotel piano bar and enjoyed some drinks and music. I had followed my wife into the bar area and afterwards she mentioned she had noticed the men’s eyes, that had been looking at her, turned to look at me. This is something I was completely unaware of as I must have been sailing high on the experience. At one point, my wife leaned over and whispered to me that the guy behind me was looking past his wife, who had her back to me, and staring at my legs. At this point I did the old ‘hand running up and down the leg’ trick which made my wife laugh and almost gag on her drink. Needing to use the washroom and not wanting to push my luck any further, we retired to our room. What a high! The next day I was left alone while my wife was attending the conference. I changed into a simple jeans outfit and headed out to another nearby mall. On the way to the hotel parking lot, unknown to me I passed my wife who was with one of the other attendees walking about during a coffee break. She told me later that I had blended in with everyone else around. Once at the mall I spent some time in the Sears outlet store, chose a few samples to try on and headed to the change rooms. With a moment of fear, I saw that there was a woman handing out a number tag reflecting the number of items one had, before entering the change area. Realizing that stopping and turning now may raise suspicion, I forged ahead….and did not encounter any problems. Nothing looked good on me, oh well. I don’t know if this experience will ever be repeated. Only time will tell.

Who suspects?

Well, there was this one time during my past careers early training that there was a winter festival that involved a womanless pageant. There was a call for volunteers; no one came forward until the last minute…me! I used the excuse that I had done something similar during the past Halloween at my precious location. I didn’t have anything overly “sexy” with me so this is how I looked. As you can see, there were a number of guys who saw me this way…but it was all in good fun. Right? No, I didn’t win. Some other guy had his girlfriend make him up in a sexier outfit…I knew I should have gone shopping..lol.

So I got away with it this time. Next time I stepped out was at Halloween a year later, looking something like this. This caused a bit of a stir later that evening when one of my instructors was slapped across the face by a woman he had felt-up, thinking she was me…lol. I drank quite a bit that night, danced with the wives and girlfriends of the guys as well as a couple of the guys themselves. Thankfully I was dropped off at my apartment, while the others went to party elsewhere. I dread to think how the night would have ended otherwise.

And the last time the same group of guys saw me dressed was during the following years Oktoberfest theme night. As there were no girls among the students, I again decided to have some fun. Oh, fun was had, by most, but a fight did almost break-out when someone got the wrong idea of what was going on (I think the words where along the line of “oh, you are one of THEM types. We have no need of you , you…something, something, something”). Fortunately the situation was quickly resolved by the guys around me (protective bunch they were) and the evening continued without further incident.

So, as you can see, there are a number of guys who have seen me dressed on more than one occasion…so do they suspect? Nobody said anything at the time, but I’m sure there are those who do, including at least two, who, on the occasion of my wedding gave me a card mentioning something about crossdressing and marriage not being compatible. Well guys….18 years and counting. I will attempt to continue to maintain a happy balance within my life (work, play, time away and time at home), of which crossdressing is only a part of my total life experience.

There are times I wish I could again get away from the house while dressed, but reality has a habit of getting in the way. Therefore, I am more than happy to enjoy those rare occurrences when I do have the chance. Wouldn’t be anytime soon though.



  1. Great story and I loved the pictures. Thank you for sharing!

  2. Hi Michelle,
    Some terrific stories. I have looked through your picture archive and it’s really terrific. You’ve obviously put in a lot of practice over the years!
    From this story involving your wife, she seemed to be fine with it from the very start of the relationship, and she seemed to enjoy the evening you spent together in the bar. Why has it never happened again?

    • Thanks Vivienne.
      We live in a small community, that and the job I was in did not allow me to get out locally. I suppose, being frugal newlyweds, we didn’t want to have to drive to the city and get a hotel room for something like this and I think I didn’t want to push my good fortune. A number of times I would dress at home, but then we started a family and as they grew, Michelle time diminished. Priorities.

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