Interview with a cross dresser

👠 I am a mature guy who cross dresses in his spare time. Having explored the landscape for a few years now and built up quite a collection of women’s outfits, I thought I’d reflect on my journey into the crossdressing scene, in the form of a fake interview. Let’s go…!

Who are you and where are you from?

I am a guy from the U.K., but currently living in Spain.

🤔🧐 Cross Dressing: Why do you do it?

First of all, I love the visual aesthetics of fetish and lingerie on women! I love the feel of the materials on the skin, it’s a completely different effect to wearing casual loose fitting clothing. I love wearing outfits that are designed for the female form but when worn, create tension, tightness and stress points on the body, which is kind of a turn on as a guy and it goes against the design and intended form of the fabric. Also, there’s a naughty element to it all and the risk of being ‘found out’ in an extremely unexplainable outfit!

Also, the taboo nature of the whole thing as it challenges my social norms and I really like dressing up and seeing myself in sexy outfits which are sometimes even too risqué for the bedroom!

How do you think you got interested in cross dressing in the first place?

I think it probably started when I was young and there must have been something which triggered it, but I don’t think it was a predictable way, such as trying on your mum’s heels and being told off! I think it was more to do with just liking fetish and lingerie and wanting to experiment with it in private. Also, the desire to want to get involved with fetish and try new things in the bedroom.

I’ve always been fascinated with the psychology of it all and it probably comes from some experience years ago or some self-ego reflection and the desire to experiment over the course of my sexual adult life.

When did you start actively cross dressing?

The first time I started trying on female clothes was in about 2010. I threw a fancy dress party at my flat and a friend, who got changed in my bedroom, left her sexy fishnet stockings behind when she left. They were part of her costume that night and she forgot about them, and for some reason I kept them! I was already interested in fetishwear and lingerie and also super sexually curious, so it was just another ‘kink in the box’!

One day I decided to try them on, just to see what they would feel like, and they turned me on! They were a striking red colour and felt really good against the skin. Also, they were super feminine and delicate and a bit uncomfortable to wear, but in a sexy way.

What elements of cross dressing do you like the most?

It’s hard to really pin-point specific ones, but probably it is my love for fetish wear and bondage gear, plus the striking visual aesthetic that goes along with cross dressing. Also the ability to try different combinations of lingerie, latex, leather etc…it can get quite creative! It’s also nice to recreate erotic scenes at home and take photos of myself. It’s also a creative pasttime and probably related to wanting to see a female/partner wearing a particular outfit, but without the hassle of having to ask for something so slutty and naughty!

How would you classify yourself in the world of cross dressing?

For me, it is something I currently only do at home, in private. So yeah, I consider myself a cross dresser in private. I think it’s also good to make a distinction between a cross dresser and a transvestite. For me, it is (currently) all about trying on and wearing female clothing in the privacy of my own home. In fact, I am a heterosexual guy with a partner and currently only interested in women.

👗 Outfits: Where do you buy them?

Almost all of my outfits and accessories that I buy are from Shein, AliExpress, Temu etc…but I also own various items, which were purchased in the UK and from Amazon. I have never bought any female garment from a real shop in person, yet!

What were the first few outfits or items that you bought?

I guess they would have been items that I bought for ex’s in the past and I can’t remember exactly. For my own collection, I think it was a lace up black corset. Then quickly after, some lingerie, stockings & suspenders and then some heels. Now I buy clothes regularly, mainly from the internet.

Do you have any specific looks or styles when dressing up?

I like the look that PVC, latex and leather give you, as well as lace lingerie, especially fishnet. Also, skin-tight outfits are better. This said, I tend to have a few classic outfits - the dominatrix look, with mainly shiny black aesthetics and the PVC fetish look. Also the sexy prostitute look. In addition, I love uniforms and like the police woman, school girl, nurse and secretary looks. After that, I generally like anything that looks very feminine and hot. It always amazes me that I can pull-off some of the outfits and look quite convincingly feminine.

FYI - the photos below are not of me, they are some styles that I like

In addition, wearing silicone breast forms really opens up a whole load of feminine possibilities. For example, you can try the more eye-popping combinations, especially with the cleavage and large G-cup sizes. Also, for corsets, bras and dresses, you get insane cleavage and all the outfits really fit well and tight.

How much have you spent on outfits so far?

This is really hard to say, but I would say around €1000 - €2000 probably. Some items cost more than others. I would say most things I buy are between €5 - €30 per item, then there are more expensive items, such as heels or full dresses.

When I first started trying on outfits, I realised that I only needed a few more items to create the perfect fetish scene. You can really be very creative. So I just got addicted and had to complete the transformation from simply dressing in women’s clothes to looking like a fantasy fetish model.

Over the course of a few months I kept purchasing corsets, stockings, suspender belts, thigh high boots, pvc, more heels and various other accessories and bondage gear to complement the look. As I shop around more, I realise that I have only just scratched the surface as to what’s available to buy and there’s a lot of things on my wishlist.

What’s the most expensive item in your collection that you have bought?

I would say a pair of black thigh-high PVC boots. They cost me about €90. In the past I bought some black thigh-high latex boots, which cost €120, but I had to send them back because they were too small. I also spent about €80 on some G-cup silicone breast forms, but I actually sold them because they suffered a rip.

😈 Frequency: How often do you dress up?

It varies to be honest. It can be anything from a few times a week to once every 2 weeks. I would also say that in summer it is less, due to the fact that it is simply too hot to do it in Spain!

Do you cross dress in public?

Not usually, no, but I have worn items under my normal clothes before. It makes the day a lot more interesting, but I would probably be quite embarrassed if somebody noticed. I’m not sure what I would do to be honest!

Do you do it with your partner?

Yes, but usually it is for a particular scene or outfit and a bondage session, rather than just playing dressing up and experimenting with different combinations. She knows that I have the clothing items as she’s seen them and supports me 100%, especially since it takes up a significant space in our bedroom!

Was it difficult to tell your partner?

Yes but I would say that her personality made it easier, since I trust her and she’s very open-minded and easy going. I was quite nervous but I had already told her that I am into kink, fetish and bondage right from the start, so it wasn’t so much of a surprise to her I think. Fortunately, she was very understanding and open, and now is more curious about it all and super supportive. I know that this is not always the case with some relationships and so I suppose I am very lucky.

Have you taken any photos while dressed up?

Yes, lots! I do it for myself, to see how different outfits look together and also so I can go back through and see which combinations worked the best. I have a Fetlife profile and I occasionally put photos on there. Also, it can take a long time to put yourself in the exact outfit that you want, so it is also good to have a souvenir after all the hard work!

👠 Heels: How many pairs do you own?

I have lost count, but maybe 20-30 and I hope to expand my collection once I move house. I could happily buy more and more and I’m sure by next year I will have doubled my collection! I also own different styles, so stilettos, courtroom heels, ankle boots, knee high and thigh high, all with a heel.

How do you choose the correct shoe size and fittings?

Update: I have since written a post about this here.

This requires quite a bit of estimation and luck, since there appears to not be an international standard for shoe sizes, but I have measured my feet precisely and it also depends on the style of heels. For example, with knee or thigh high boots, I find that you need to be very specific about the sizing, since if you can’t get your feet in, they simply won’t fit or zip-up. Sometimes, you can get your feet in and the shoe size feels correct, but you can’t zip up over the ankle, especially for heels designed for women.

With others I have, such as the courtroom or stiletto heels, there is more room for error. Also, you need to consider a lot the width of your feet, since women’s feet can generally be thinner, but feet come in a lot of shapes and sizes. Also, if the heel is open, such as open at the toe, there is also a bit more flexibility on the sizing.

My feet are EU 45-46 and as a rule I go for one size above, or occasionally two for boots, but I measure in centimeters, since it is easier to guarantee that the shoes will be a certain size. I also account for my own feet being different sizes (which apparently is very common) so I take the largest foot size. Having said this, I can fit into a size EU45, but they are not comfortable to walk in.

Actually when I bought my thigh high boots, I chose a shop on AliExpress which allowed custom measurements and even then the shoe size was fine, but I couldn’t zip them up over the ankle, so I had to request another pair, which they kindly made at a reduced cost.

What heel height do you normally prefer to walk in?

When I started my collection, I began with a modest 12cm heel. Sometimes they are measured in inches, so the height is not always standard. For the next few pairs I went straight to the ‘top shelf’ and took an 18cm (7 inch) pair and a 15cm pair (6 inch). I find that I can comfortably walk in 12cm heels but 15cm heels are more of a challenge. The 18cm one’s are very difficult to walk in and even standing up in them for 5 minutes can be intense. It gets easier, but I don’t wear them often enough to train my feet. In future I will probably buy some lockable ballet heels, which are super high, but they are currently on the wishlist!

💃 Session: What would a typical cross dressing scene or session look like?

It depends really on my mood. Sometimes it is to try on newly purchased items, or sometimes just for the fun of dressing up. Sometimes I have a spare few hours and it helps to take my mind off other things, such as work. I suppose it is just indulging in any activity from which you derive pleasure and relaxation, such as gaming or reading or shopping, or whatever.

More recently, I try to go for striking looks and I like to create new combinations. It’s nice to be able to test new outfit combinations, especially since I have a lot of outfits to combine. Each time I am finding new styles, which I had never realised would look good, for example fishnets over latex. It’s like being able to create your own porn scene - as filthy as you want!

I also have a lot of fetishes so it allows me to keep connected with my fetish collection and bondage gear and understand what I like and dislike.

Sometimes I like to try fetish outfits or scenes that I have seen in the past, on women in clubs for example, where they have been dressed up in fetish gear or sexy lingerie and I have really enjoyed the visual aesthetic at the time, so now I can recreate these fantasies in private, without needing to explain myself to anybody. It’s quite addictive though, as women have so many outfits and you can just keep buying more and more items!

Is there any item that you always wear when dressing up?

Yes, heels. No look is complete without them. I usually put them on near the end, to complete the look. Also, some fake breast forms, since visually it’s very feminine and bras and tops fit much better.

🧠 Discovery: Have you discovered anything that has changed you as a person?

Yes definitely. I have become more in touch with gender identity and my inner perception of my own gender.

I have also discovered that there’s literally thousands, or probably millions of people out there online who love to cross dress. Just on Fetlife alone, I have seen and spoken to many and all are humble and polite. You can tell that with some people they are just starting out and they are nervous or embarrassed, then there’s others who openly dress in public or who are MtF or openly transvestites.

I have also been to events and told people that I am a cross dresser and they are interested and very supportive - possibly also a little surprised but generally positive about it. The city where I live is very open minded though, so that also helps.

What have you learned from cross dressing?

I have learned that it is something that I participate in behind closed doors and I (currently) don’t have the intention to walk around in public dressed as a woman. Probably it’s a side of me that most, if not all of my friends would be surprised to discover, although I am usually fairly confident and open about my kinks if people were to ask me.

I have also learned that I love to pair crossdressing with bondage or self bondage (hence this website!). For instance, I take the role of a bottom and like to be restrained while wearing female outfits.

Do you secretly identify as a female or have a female name when in character?

Well, I don’t have a female name or alter ego just yet but this might happen over time. If I had to choose, it would be something like Charisma or Carmen…but I am still in the experimentation stages at the moment.

I also don’t identify as a woman but it is a nice fantasy for the future and I would like to explore being a woman for longer periods of time, but only with other cross dressers or TV’s.

🙂 Conclusion

So there you have it! If you can relate to any of this, please get in touch and share your story, I would be interested to hear it 😉