My Crossdressing Story: How Did I Get Here?

I feel that every crossdresser that I talk to has a similar but unique story on how they got started with crossdressing. We are similar to snowflakes in my opinion, from far away we all may look the same, but when you get a closer look we are all unique in our stories.

For some, crossdressing is just a fetish for them, and they love engaging in sexual acts while dressed up and feeling sexy! For others, it is a way to relieve anxiety and get away from day-to-day stress.

Personally though, I feel stuck in between those two categories of crossdressers. I very much enjoy escaping for a few hours to be Catie and not think about my bills or other responsibilities, but at the same time I love to feel attractive when wearing feminine clothes which triggers me to be aroused by how sexy I feel.

As a straight identifying & married man, this can be very confusing as it takes mountains of courage to admit either one of these things. The reason why you crossdress changes how people see you as a crossdresser as well.

For example, someone might be completely on-board and understand that you just like to put on a dress or paint your nails to relax and get away from things. They might see it as harmless, but that same person might not accept you if it was a fetish for you and vice versa.

The point of all this is to say, the only person that you truly need to accept you, is you. It is your ‘reason why’ and you should never feel shame for being vulnerable and open about your feelings and experiences. Only you know everything you’ve been through to make you the person you are inside and out so they do not have the adequate knowledge or experience to judge in that way.

ANYWAY, let me get off my soapbox for a moment and get into the details. I have been crossdressing on and off for 20 years and I have had MANY ups and downs to get me to where I am today with crossdressing.

This is my story.

Early Days

When I think back to when I first remember crossdressing, I always struggle to remember the age I was and what triggered it. For simplicity sake, I tend to give the age of 10 as when I started crossdressing even though I think it was probably earlier than that.

The first memory I have of crossdressing was more around the age of 5 or 6 when my brother and I imagined that I was the mother of a doll that my younger sister had. I took a blanket and wrapped it around my waist to look like a skirt. It was a small and harmless moment, but I think back to it every time I get asked about when I started.

When I actually started to crossdress though, it began with wearing my mom and sister’s panties. It was the most obvious difference that I noticed between boy’s clothes and girl’s clothes initially. I honestly don’t even remember how it made me feel, but I think at the very least it made me more curious to try on other “female clothing”.

I also remember trying on night gowns of my mom and swimsuits of hers. All of this I kept secret because it was clear to me that boys shouldn’t wear girls clothes.

I do not remember being caught at a young age. I feel like I generally hid all my activities well early on and solely did it out of curiosity about what it would feel like to wear girly clothes. I obviously enjoyed it enough to continue, but I really still don’t understand why I started trying it in the first place.

Teenage Years

When I became a teenager, I can remember a lot more vividly the situations and details of my crossdressing. At this point I was not just trying on my mom and sister’s clothes, I also had girl cousins that I would wear their panties. Side note: I want to apologize to every single person that I “borrowed” panties and clothing from. It is something that happens much too often with crossdressing and I truly feel sorry for taking your clothes.

That type of situation is also how I remember first being caught by my parents. I remember that one day after coming back from hanging out with my cousins, my mom found a pair of my cousin’s panties that I had taken home in my backpack. She sat me down and asked me why I had them and I admitted to her why because she threatened that if I wasn’t honest, she would force me to tell my cousin that I took them.

In our talk, we discussed if this was just a phase or not. I quickly said that it was just a phase and not to think about it too much. Fast forward to being caught in similar situations at least 5 more times, my mom was not convinced that it was just a phase.

She asked me the questions that I think all crossdressers get asked: “Do you want to be a girl?” or “Do you like boys?” I obviously said no to both questions and I was being truthful. I never have wanted to be a girl, but it is hard to explain that as a crossdressing teenager.

So instead, she let me sign up for sports which is something she hadn’t let me do in the past. Looking back on this, it was definitely something that she thought would distract me and stop my crossdressing.

Which it actually did because my later years of high school were less focused on crossdressing and more focused on sports and getting into college. I still had some “borrowed” panties, but it consumed much less of my time than when I didn’t have any other things to focus on. I didn’t really dress up at all the last few years of high school.

College

When I reached college, I was ready to crossdress more. I felt like the last 4 years in high school pushed all of the urges to dress to the back of my mind, but they were ready to come out! In addition to that, seeing college girls in their party outfits and makeup definitely caused me to be triggered to crossdress more often. When I see a woman wearing something that makes them look beautiful or sexy, it makes me wonder how I would look in it.

I continued to “borrow” from girls, but this time I would find stuff left out in the laundry room and take it from there if nobody was around. Again ladies, I am so sorry! I also had a girlfriend from high school that I had finally come out to and she was somewhat interested in my crossdressing. She would let me put on her panties and also any clothes that fit me. This is when I started getting the sexual aspect of crossdressing.

I enjoyed being seen by someone. I enjoyed her smacking my butt and letting me wear panties while we had sex. It was great until it got to the point where I think I became too obsessed with it. She was the first person that I had ever come out to and accepted me for it and I think I took it too far and focused too much on it. We eventually broke up and I continued to dress in private throughout college.

Adulthood

After graduating college I finally started making money to begin buying my own feminine clothes! I also got my first wig and began experimenting more with makeup and accessories. Seeing myself fully dressed in a wig for the first time was a wonderful feeling. I wouldn’t say euphoric because I don’t want it to be confused with gender dysphoria, but I felt attractive. I was even somewhat passable at the time which many crossdressers strive for!

At this point I had really dove deeper into the fetish category. I would find myself crossdressing in my room at night and next thing I know I am aroused and pleasuring myself. It felt so taboo that it was exhilarating, but I also felt a lot of shame from this and found myself purging my clothes every few months.

It was a very up and down time with crossdressing for me. I felt the most attractive I have ever felt as a crossdresser (dare I say, as a person), but I felt the most shame I have ever felt as well.

I got married to a wife who is accepting now. I will give more details in another post on how she and I have progressed since we have been together, but it is safe to say that I have made plenty of mistakes. But through those mistakes, I have learned and grown so much as a person that I cannot believe how far I have come since the beginning.

Currently, we are working to explore my feminine side together. We have gone to get our eyebrows shaped up together, and eyebrow threading isn’t bad by the way if you have never tried it! We have also discussed dressing up in front of her and even talked about trying out pegging as well.

To Wrap It Up

As I said in the beginning, we are all snowflakes in the crossdressing community. I have learned from others to be open and vulnerable about my thoughts and feelings.

My anxiety and stress have gone so far down in the last year or so because of this advice. I have also come into my own style and obsessions with femininity. I love a pretty dress with a pair of heels. I love wearing press-on nails and seeing my painted toenails. And I love thongs! They are my favorite go-to style of panties.

I hope that if anyone who is struggling with their crossdressing identity reads my story, they can relate to me in some ways, but also look at themselves and be true to how you feel inside. Find a therapist or community to talk to about your feelings and connect on a personal level.

Understand that it is probably not “just a phase” and the sooner you can accept yourself, the sooner you’ll find happiness. Last but not least, I wish you all success in discovering all of the uniqueness with your personal crossdressing stories!