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I met H* over a decade ago when I started working at the same place as him. I had been 18 for roughly a week. He was a few years older than I was, but not enough to make my parents bat an eye.
I fell for him hard and fast, despite my intentions of not getting serious about a guy, having suffered my first real heartbreak (my boyfriend of two years dumping me for a girl he had assured me for some time was only a "friend") only a month before.
He was confident, just cocky enough for me to find charming, had the sexiest smile, beautiful brown eyes, and made me laugh so effortlessly. My defenses didn’t stand a chance. I was smitten and we were inseparable almost immediately.
Despite him having several years on me, I was the more sexually experienced of the two of us, a fact which seemed to both annoy and relieve him simultaneously. It bothered him that this innocent-looking 18-year-old had seen her share of naked men, but it also released him from feeling like he had to treat me with kid gloves.
Several months into our relationship, maybe six or so, he dropped his first hint to me. After we’d had sex one night, he informed me he was keeping my panties. I was slightly scandalized, having never gone commando in my life, not to mention they were one of my favorite pair. Red and totally sexy.
My hesitation quickly dissipated though, when he made it clear how hot he thought it would be to keep them. He told me that if I played nice he might even wear them for me next time. I stared him straight in the eyes and said “I DARE you.” I thought that I’d just steal them back next time I was over.
He made good on my dare. The next time we had sex, I unzipped his fly and pulled down his jeans to discover my panties on him. I laughed uncontrollably, hardly believing that this macho guy was wearing my silky red panties.
I said “Oh my god! I can’t believe you wore them!”
A flicker of vulnerably was present under his grin, and he asked me “Is it stupid?”
I didn’t have time to process the words before they were even out my mouth.
“God no, it’s HOT!” And I meant it.
He surprised me by wearing them a few more times over the following months. And my positive reaction to it always seemed to please him. He finally worked up the courage to tell me it was a kink of his, and that he wanted me to go shopping with him to purchase pairs of his own.
He slowly confided in me that it went beyond a kink, beyond underwear, and that he wanted to fully dress like a female. He said that I was the first person he had ever told, because he felt like I wouldn’t judge him.
As a female who, unknowingly at the time, pushed against gender-specific clothing boundaries for most of my adolescence (big baggy jeans, boxer shorts, oversize T-shirts, combat boots, wallet on a chain, and a loathing of makeup), I tried to reassure him. I told him there was nothing abnormal about it and that it was as normal as my "tomboy" tendencies growing up. Society was just more accepting of it when it was me dressing the way he was expected to.
But I fully admit that part of me was confused. Why on earth would he want to wear dresses? Heels? Pantyhose? Makeup? It didn’t make sense to me, mainly because those were things I hated about female clothing. I worried too that maybe he didn’t really like girls.
I had a LOT to learn.
So, to educate myself and assuage some of my fears, I got online and started reading. And I learned about so many different types of men that like women’s clothing. Cross-dresser, transgender, and transsexual were terms I came to understand a little better.
And I also realized what a huge deal it was that my publicly presenting hyper-masculine male had told me this secret. It had been a heavy thing for him for so long and I didn’t want it to be anymore. So I threw myself into emotionally supporting him as much as possible, letting him know he had the freedom to be himself with me.
When he asked me to attend a "meeting" with him, I agreed to go. He found a group online that met once a month as a sort of support group for cross-dressers and trans persons who were born male. Partners were welcome to attend, so he brought me with him. We got a hotel room for the evening and I helped him get dressed and did my best to help him with putting on makeup, though I’d only worn it a few times in my life. I dressed myself as professionally as I could, feeling a little nervous and unsure about what to expect.
There were a dozen or so cross-dressers and trans persons there and I felt awkward and uncomfortable, being one of only three cisgender females in the room. But I did my best to appear calm and collected. I held H’s hand and gave him small, reassuring smiles when he looked at me.
There was a transgender male-to-female who at one point in the evening said that she wished for nothing more “than to be a 20-year-old female.” I (who was 19 at the time) took the hint. I wasn’t welcome there and it felt like I was invading someone else’s safe space.
After the meeting, H seemed to feel relieved, even elated. He wanted to do something "daring," so we went through a drive-thru with him still cross-dressed. The teenage kid at the window did a double take and we laughed about it all the way back to our hotel room. He felt better, a little less abnormal. And I was relieved.
A few weeks later, he asked if I’d be willing to go to another meeting and I told him that I didn’t think it was right for me to go. I had felt uncomfortable and got the impression that my presence made it uncomfortable for some of the people there. But I encouraged him to go again.
In the end he never did, but I think that the single meeting helped him to understand he’s not alone. And I can understand how important it is to know that.
We married a few years later and he cross-dresses less and less frequently as the years go by. I think he likes to catch me off guard, because there are never any hints from him. It’s usually a surprise and I kind of like it that way.