Coming out. I’m straight. With a twist.

If you read this entire post, we should be friends. Sorry it’s so long, I didn’t know I had so much to say.

Yes. You read that right. I’m a straight man. I was never gay and I’ll never be gay, I only like women. More specifically, my fiancée who I’m ready to marry next month. But I do have something I think I should come out about to her, and even to my family before I take this step.

This may be not be the place to talk about this and if it isn’t, I’m sorry. It’s something that pretty recently and very quickly took a grasp on my life, and I think that it’s become serious enough now that I can’t ignore it as a “bad habit” anymore like I used to my entire life. Now I’ve come to enjoy it regularly (in private, of course) and I’ve come to a crossroads in my life where I need to decide if I’m gonna continue this, or drop for good. I’m a crossdresser.

That’s actually the first time I’ve admitted it to myself so that’s a start, I guess. For as long as I can remember, I’ve been fascinated by skirts. More to the point, I’ve always been fascinated (not in a good way) that society dictates that only girls and women are allowed to wear them. I never thought that was fair, but I accepted it and never gave it much thought, other than I’m a boy and these pants are made for me. But girls wear them too? AND they get skirts too?! Not fair!!!

Growing up into my adolescence, I discovered that I get aroused by seeing an attractive girl in a short skirt (as probably most straight preteen/teenage boys do), but I also discovered that I get aroused instantaneously by wearing a short skirt. I didn’t know why, but my raging teenage hormones didn’t ask too many questions. I always knew I was attracted to girls, so the thought that it might be because I’m gay (which now as an adult I’ve learned that a guy who crossdresses doesn’t instantly mean he’s gay) was never an issue for me. I’ve never had a question about my sexuality. But the misconception of a straight teenage boy wearing short skirts to get aroused might be a bit misleading to some uneducated adults about sexuality in 2018. Like my Christian parents.

As I grew older, not much else changed. I was a normal guy, wearing normal guy clothes, doing normal guy things, and only occasionally remembering oh yeah, I used to do that. And even more rarely when I’m all alone and an opportunity with a skirt arises did I actually take that opportunity. It was never an issue for me about what I used to do, I was a kid. My hormones were out of control, everyone goes through puberty differently. But I still always found myself taking extra looks at girls wearing skirts on my college campus, or walking down the street or pretty much anywhere else. I just thought that it’s really sexy for girls to wear that, and I’m not a pervert who wants to follow them around and touch them or take pictures of them for myself. I always thought “It’s okay to look, it’s not okay to touch.”. Today I think of it more as “It’s okay to look, it’s not okay to violate.”, as in following and touching and taking pictures etc.

The one day, I couldn’t even tell you why, but I guess just out of morbid curiosity because of all the thoughts that must have been going through my head at the time, I went on eBay and bought myself a skirt. In my name, with my money, it was my property. It was a blue and gold cheerleader skirt, which now that I think about it I most definitely overpaid for, but within a week it arrived and I put it on. Me, not knowing women’s clothing sizes, ordered it a bit too small, but it fit. I looked in the mirror at my new skirt and I thought “Damn. Why am I doing this?” as I twirled around and watched how it moved on me and started to get me tingly. I took pictures of myself wearing it, I took videos of myself wearing it and moving around in it, and I kept it hidden in my room. Always knowing that it was right there for me when I wanted to be weird. I was single at the time, and going to college while working a weekend job and still living with my parents so I had quite a bit of private time. I had it for about a year, when one day my parents took it upon themselves to clean, redecorate, and reorganize my entire room while I was working. The second I opened my door and saw how immaculate everything looked, I went right to where I was hiding my skirt for the past year and sure enough, it was gone. I’ve been caught by my parents. And they weren’t even home to try to smooth talk my way out of it. I had no idea what to do, they hadn’t contacted me all day so I didn’t know if they were mad at me or if they needed to have a serious talk with me or anything. When they got home, they seemed nice enough. “Did you see your room? It took us all day to clean it.” “Oh yeah, it looks great! But why? I was gonna get to it myself eventually.”, I said. I didn’t get any feeling of suspicion or hostility from them, just a flat out “We found a skirt in your room. What was it doing there?”. And this next part is nothing short of miraculous. I’ve never BS’ed my way out of something with my parents like this before and claimed that it was a Halloween costume from my job. The girls were going as football players, and the guys were going as cheerleaders, and they wanted me to be a part of it with them but I didn’t want to, and I was going to give the costume back. They bought it (probably not, but it got me out of trouble), and I went back up to my room and breathed a huge sigh of relief. My skirt was gone, but at least my parents don’t think I’m some freak. And from then, I didn’t buy another piece of women’s clothing. ...until 2018.

Now I’m in a serious relationship, the cheerleading skirt is long gone and I’ve never been happier. But with my new fiancée, my crossdressing focus seems to have shifted to a different article of clothing: panties. One day, she asked me to put hers on while in bed together, and she said that she really liked how my butt looked in them. That was probably the fastest arousal I’ve gotten up until that point. We had sex and then I spent that night in her panties. Of course, I didn’t want her to think I want her to let me try on all of the panties she brought with her from home that weekend, so I took them off the next morning and changed into my boxers. But I really wanted more. Since then, we’ve swapped underwear a few times and thought it was funny, but I loved it wearing her underwear. I loved wearing women’s underwear. So much that... I went out and bought some. For me. I don’t know what it is, but I just wanted to throw out all of my boxers and replace them with silky, lacy bikinis and hipsters. But that would surely get me caught, so I thought two would be enough. I still have them, and I haven’t been caught with them. Yet. Because when I started to wear them regularly, I started to want something else that I hadn’t done in a while. Skirts.

I remember Googling pictures of men in skirts, not to arouse me (because men don’t arouse me), but as reassurance that there are guys out there who not only wear skirts, but have their picture taken wearing a skirt and have it posted on the internet for anyone to see. And that’s when I thought “screw it, I’m buying myself a skirt.” After browsing through everything that a “miniskirt” search returned on Amazon, I settled on a pleated tartan miniskirt for $15. Already impatient, I cut off the legs from a pair of jeans I didn’t wear anymore, and the result was a very uneven, very short denim miniskirt. It looked horrible, but I was (kinda?) wearing a skirt again, only this time with panties on underneath, and that just brought a whole new rush of hormones to me. Two days later my real skirt arrived, and I was so excited. I would wear it as soon as I was alone, I would look at myself in the mirror, and I would even be a little daring and wait until it got dark to put on a hoodie, my skirt, and some shoes to do something outside quickly like take out the garbage, or get something from my car. It was exhilarating to be wearing a skirt outside of the privacy of my home. Today, I wear the skirt every opportunity I can. I bought another one, and I interchange them. I wear it on my drive to work, and I wear it on my drive home from work, because I keep it in my trunk, where I have the only key to open it. Somewhere in that time, it became more than occasional crossdressing. And now, it has become more serious than ever.

Halloween is approaching, and it’s not uncommon to see people already buying Halloween costumes and decorations. So yesterday (literally yesterday as of the posting of this thread), while doing my shopping at Target, I wander into the Halloween section and see a long and sleek blonde wig. I thought why not? I threw it in my basket, I went to the self checkout lane and went home. When I got home, I took a shower, put a clean pair of panties on, put on a tartan skirt, and a T-shirt, before putting on the wig and seeing myself with long, blonde, girly hair for the first time in my entire life. It was unlike anything I’ve ever felt before, and it made me realize that I’m slowly become a true crossdresser. Now I don’t know what to do. I was once just some regular guy, now I’m lying down in bed, pulling down my skirt so my panties aren’t exposed, and on top of that, figuring out what to do about this long hair that keeps getting in my face. It’s a cheaply made wig, but it can be styled. If I knew how to style. But now here I am, girlier than ever, still a guy, still not into BDSM, and most importantly still straight, not knowing what to do. That ugly girl looking back at me in the mirror is starting to affect me. I just don’t know what to do, and I certainly don’t know how to let my loved ones in on it. I don’t want to live a secret life, because getting caught would be horrifying for everyone involved. If anyone could help me, or point me in the direction of someone or something that could help me, I would greatly appreciate it. Thank you so much for reading my story. Now to think about my next move...