Then and Now

If you are reading this, you likely have a story like mine.

(Sorry, this is going to be longer than most of my posts).

As a young boy, I saw a dress and I wanted to try it on. I did, but it didn’t fit.

That desire to dress like a girl/woman has never gone away.

At Halloween, I was always jealous of the boys at my school who came to school dressed as girls. Up to sixth grade, we’d wear costumes to school, and then trick or treat when it got dark. 

I’m still jealous, all these years later.

In eighth grade, I can’t remember how, but I convinced my mom to let me dress as my sister to go trick or treating (my sister was two years older than me). Nothing fancy, but my mom had a wig, and I wore a top and a skirt, some knee socks, and my own tennis shoes. When I knocked next door at our neighbors, my neighbor Mimi thought I was my sister.

I had roughly two hours of happiness, doing something I had wanted to do for seven or eight years. Unlike many others whose stories I’ve read (like Kandi’s, who encountered guilt and shame), I was always ok with wanting to dress. I never felt shame or guilt.

Like many others with older sisters, I was always tempted by her clothes when no one else was around (for others, it was mom’s clothes).

One day during puberty I wanted to try on a pair of my sister’s pantyhose, to see how they felt. Without warning, and without assistance, I had an immediate male reaction. From that day, I’ve realized that dressing is a part of my sexuality. Again, no shame or guilt. It was just part of being me.

I was shy around girls so I was a late bloomer. I dated a little in high school and college, but nothing serious. So it took me a while before I became physically intimate, much less exploring dressing. But I was always wanting to do it, but afraid to buy clothes or broach the subject with the women I dated. I’ve now met others like me, who are older than me, and their wives still don’t know their secret.

I met my (now) wife while traveling in a foreign country (foreign for both of us). We started traveling together, and one night I convinced her to put makeup on me (I can’t remember what I said). About a month later I traveled to Australia, and she put some makeup on me and let me try on some of her clothes. Again, I can’t remember how it happened. I never said the magic words, “I’m a crossdresser”, but at a minimum she had to know I was interested. 

My wife and I put the Long in Long Distance Relationship. Give or take, it’s about 7,500 miles from my hometown to hers. That’s a large part of why it took seven years from meeting to marriage, with breakups during times apart (two of those seven years we didn’t see each other, and when we did see each other, it was generally for a month or two and then a long time apart).

During the separations, I dated. With my most regular girlfriend during the time, I hinted at wanting to dress but she was never accepting, so I didn’t push it. Ironically, one time right before she was going to sit for the November CPA exam, she pretended to hypnotize me so I would take the exam for her. As it was near Halloween, I thought about getting dressed up as her and saying it was because of the hypnosis, but she was so stressed out I don’t think it would have gone over well.

Also in this timeframe I met Renee. We met because she put a personal ad in the weekly free newspaper, and I answered. We dated and were more FWBs than boyfriend/girlfriend (she agrees), but we enjoyed each other’s company (and still do; we message frequently and she loves seeing me dressed, and offers her suggestions).

One day I am sure I pushed the discussion towards dressing up and I said something of the effect that my feet were too big for women’s heels. Renee said no, they weren’t, and to prove it she would buy me a pair. I said if she bought me heels, I would get dressed up, if she would help me.

And to my surprise (and delight) she found a pair of black heels that fit me (later on, she had a roommate who was a crossdresser and we would be out on a date and Renee would tell me she was wearing one of her roommate’s dresses). So the night came and Renee made me up and dressed in in one of her floral suits; bra, panties, pantyhose, the whole nine yards (no wig though). She said I looked better in her clothes than her. 

I occasionally wore her lingerie to bed when we spent the night together and I got dressed one other time with her. Originally I left the heels at her place, but then she met her (now) husband, and we parted as friends, and she gave me the heels.

Those heels were the first item of women’s clothing that was actually mine. I had been too afraid to buy any, figuring the clerks would know my secret. I was even afraid to go into the store with Renee to buy pantyhose for me.

I kept those heels and put them on from time to time, until right before my marriage, when I thought it best I get rid of them.

Meeting Renee and getting her acceptance about dressing still means a great deal to me today (thanks again, Renee).

About eight years into our marriage my desires to dress were still there, but I was more willing to openly discuss it with my wife. I asked for a red dress, and she bought me the one in the picture–my first dress for my birthday. Over the next few years, she would buy me makeup, shoes (the red heels were a gift from my wife), and finally, at my request, a wig for Valentine’s Day one year. She made me up, and let me wear one of her dresses, a red silk dress. From then on, she would buy me something feminine from time to time (generally panties or a nightgown), but I was on my own for dressing up.

I would dress us every so often when my wife and family were gone. In the pre-digital days, I would set up my SLR on the tripod and take pictures with the timer. I still have some of those pictures.

Occasionally I would travel out of town for some reason, and dress in my hotel room. If I got brave, I would go to a closed block of stores and get out and walk for a few minutes, or just drive in the car at night. One time, in 2005, I actually found out about a TG event in the middle of July. I got dressed and went, and found the place. It was hot and I was sweating and extremely nervous. I lasted about 15 minutes, panicked, and left. It was another ten years before I tried going out again, on a Halloween, for about 45 minutes.

Getting braver, I went out the next Halloween for longer, and then had a makeover and a day and a half out in San Francisco (the tail end of a golf trip to Reno).

Then, in October 2016, I came out of the cocoon. I haven’t looked back. The dresses I am wearing (the pictures where I’m sitting) I no longer have. I’ve lost weight and they were donated to a thrift. 

My wife still has the silk dress and I still have the blue dress. I had it taken it because it’s a sentimental favorite. Recently, I put both on to show me, then and now. 

Me thinks I’ve changed for the better.

Sorry about the photo quality!

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