[M] Confessions of a crossdresser…

I have been a secret crossdresser for over 20 years.

Nobody in my life knows this.

I live in a large, American city with fairly progressive friends. But I can’t imagine a situation where I can even “come out” to them. Crossdressing is misunderstood. Honestly, I can’t even pretend to understand what drives my obsession. I imagine most people stopped reading this after the first few lines–because even in a place that caters to a little of everything, it just seems weird to most. I get it.

There are people who will defend gay and trans rights who are judgmental toward crossdressers. “It’s just a fetish” is the typical response. Different than not comforming to the gender you were born.

And they’re probably right. But that doesn’t make it any more common among the fetish community. If you crossdress, you’re expected to be a sissy or a submissive. But I’m neither of those things. If anything, I’m dominant.

To be clear, I don’t desire to be a woman. I have no interest in hormones or transitions. I don’t want to be the female in a relationship and I consider myself straight–although I have had sexual encounters with men out of a need to indulge my desire. So maybe that makes me bisexual? But the circumstances are very specific. There are people online who say they dress because it feels natural, but that’s not the case for me. I dress because it makes me feel sexy. I dress because it makes me rock hard. Nothing else comes close.

My longterm relationships–and I’ve had several since high school–almost always fail because deep down I feel like I can’t commit to someone to doesn’t understand and accept this part of me. But I’ve never tried to tell anyone because I fear being humiliated.

I have, at times, tried to find people online who would understand.

The first time was in college. Of course, it was a fellow crossdresser. We met through online personals.

At that point I’d been dressing discreetly for years. It started one night when I was staying at a friend’s house. I was sleeping in their guest room and his mother kept extra clothes in the closet. I have no idea what compelled me to put on her church dress, but I was aroused by the idea and even more excited when I wore it. I jacked myself off in the guest bed wearing her pink floral dress.

I spent a lot more time hanging out with that friend after that. Even as we were growing apart. It was all about going to bed and then trying on his mother’s blouses and skirts for hours. The silkier the better. One day his mother was wearing a thin white blouse around the house. She’d worn a sweater over it to work. I could see every detail of her bra and became obsessed with trying one one.

I started sneaking into drawers to try on panties and bras and slips. Anything silky and pretty. I borrowed them from friend’s mothers and sisters. My own aunts. The majority of bras were boring, white utilitarian things. Sometimes black.

The most memorable thing I wore was a black, ankle length negligee with a tight lace bodice and full satin skirt.

I never went through someone’s laundry because I wasn’t interested in the scent of a woman. It was about the clothes for me. And I never stole anything–I always put back what I tried on. I understand that it’s still an invasion of privacy and fortunately it’s not something I did for long, but for some reason I still feel morally superior to thieves or people who are getting off to a woman by stealing her things.

In my first serious relationship, I started taking my girlfriend’s panties. She had no idea about my fetish. She just throught it was fun exploration. No different than trying anal or buying sex toys. The first time was after school. I fucked her in a park and pocketed her panties. She thought it was sexy going home to her uptight parents with the wind blowing up her skirt.

But her panties were too small for me to wear. The closet we got was one night in her parents’ bedroom. They were out and we were kissing and petting and I suggested wearing a pair of her mom’s panties. She got out a pair. Black satin bikini cut with a floral pattern. I fucked her doggie style in front of a mirror with the panties pushed to the side. It was amazing, but just wearing panties isn’t crossdressing. At least not to the degree I craved.

And so after things ended I tried the online thing. I was in college at that point. I had a roommate, so it’s not like I could get my own clothes or dress on my own. I didn’t even have a place to borrow them any more.

Of course I couldn’t find a woman who was interested in meeting. So I settled for someone who shared my interests. I was picky. It wasn’t hard to find people who were curious, but I wanted someone hairless and feminine. I’ve never been attracted to men. But I thought that maybe with someone passable I could experiment a little.

I went to the house when the missus was away. My new friend had a trunk full of clothes hidden in their basement. It wasn’t stuff I would have picked for myself, but I made do and put on a short pink nightie and short robe with panties. And then I got a blowjob from a complete stranger who was ten years older than me and wearing a cheap leather skirt and sheer black top with stockings, heels, and a bad wig.

I loved it in the moment. Sitting on the couch with my head back. Gasping. Wearing panties.

My friend was worried that I would get weird after an orgasm and wanted to delay play, but I had insisted. And I did freak out and feel weird. I changed quickly and left and never went back. I wouldn’t meet another person for play until I was in my late 20s.

After college and out on my own I was finally able to start my own wardrobe. I spent to much of my first pay check on a black slip, several cheap pairs of satin panties, a purple nightie and robe set, and a very expensive bra and panty set with a matching garter belt and a few pairs of stockings. I ordered them from a department store catalog. Nobody ever saw me wear them. It was just for me.

In my mid-twenties I got involved with a switch–a woman who was into the BDSM scene and played both roles. She was dominant with women and worked in a dungeon, but submissive with men. She was a tall, European woman with a big ass and a 36DD bra. I knew I could wear her clothes. She didn’t bat an eye the first time I wanted to wear her panties. They were lace boy shorts. I got rigid in front of her and she pulled them down and sucked my cock, then told me to keep the panties.

It got to the point that I’d also wear her bra and a corset during sex. My favorite panties were a stretch satin zebra print. They were so silky smooth. She’d take them off and give me a panty hand job.

But I never wore more than her underwear. And it was only during sex. I wasn’t living my life in panties or even sneaking out of the house with them under my jeans. And so I wasn’t completely satisfied.

After her, things got wilder. Craigslist and fetlife played a role. I’ve fucked women and crossdresser and even trans. But only in lingerie. I’ve never gotten what I really wanted—to spend more time fully dressed with a partner. Recently I’ve contemplated being with a dom woman or even a man if I can just be fully dressed.

I’d be happy to share if anyone cares or if it would help someone else feel less alone.

Source: reddit.com/r/gonewildstories/comments/ad1e99/m_confessions_of_a_crossdresser