My boyfriend was a closet cross-dresser

Daisy wasn't shocked when she found out her boyfriend liked to wear women's clothes. In fact she was relaxed about it. Perhaps a little too relaxed... She tells us what it's like when you date a closet cross-dresser.

True Stories

guy in heels

Daisy didn't mind that her boyfriend wore women's clothes

There he was in all his glory. My boyfriend dressed to the nines and covered in make-up. It had been nearly three weeks since he told me he cross-dressed and personally I loved it. But as he reached for the sunset red lipstick the same old concern popped up: when was he going to come out to our friends?

First Date

I met Andy when I was 21. I had been through a bad break up a few months before and was not looking for anything too serious. So when a friend introduced us at a party I was relieved. He was perfect: so friendly and easy to talk to. The long blonde hair and tanned skin were a bonus. We decided to go on a date the following week. When he bought me roses and paid for dinner I couldn’t have been more flattered. I’d almost forgotten what it felt like to be spoiled. But it was his easygoing nature that surprised me the most. He made me feel comfortable and special which can be a hard thing to find. It wasn’t long before we had arranged a second date.

Little hints

My relationship with Andy quickly progressed. He stayed at my house most nights of the week. We had so many things in common, it simply felt right. Then things got even more comfortable than I could have imagined. I jumped out of the shower one morning to find him trying on my hair clips. He laughed when I told him he looked pretty. I just brushed it off as curiosity.

But as these occurrences happened more and more frequently I began to wonder if there was something more to it. A couple of times I even found him trying on my lipstick. I didn’t have a problem with it – I just wanted to know if he was a cross-dresser and if so we could embrace it together.


I decided to be subtle about finding out, as I didn’t want to hurt his feelings. So after a few too many drinks one night I offered to do his make-up. He said he loved the idea. I was surprised how casual it was. It felt so natural words were not needed. So I went upstairs and returned with my arms full of makeup, hairspray and accessories. He looked great when I was finished. Some people might find it hard to deal with but for me I thought it was sexy, especially with the red lip-gloss.

Coming out

The makeovers became a regular night in for Andy and I. I never even gave it a second thought. We had so much fun experimenting with different clothes and styles. It was like going out with my best friend. The only concern was that none of our friends knew. I never thought it would be an issue but when I asked Andy about it he would change the subject and become closed. I nagged for months before I took matters into my own hands and turned to one of my close friends. She wasn’t judgmental at all and she listened with an open mind. But when I told Andy he flipped. He said I had disobeyed him and gone behind his back. He left my house and stopped talking to me for a week. I couldn’t believe how unreasonable he’d been.

The Truth

Andy finally called me after two weeks. He said we needed to talk. I told him I was hurt after such a long time of silence and he apologised. In fact, for the first time in our relationship he was really honest with me. He told me that only his parents knew about his cross-dressing. When he opened up to them they had been very critical and accused him of being gay. Although they were fine now, he worried that his friends would react in a similar way. He thought that boys would respond differently to girls, that’s why he wasn’t shy around me. I finally saw it from his point of view. After all it’s still a very taboo subject even in modern society and people can be very judgmental. I suggested that he tell his best friend, Jack; an understanding guy who he had known for years. He said he was open to the idea but it would just take time.

New Beginnings

Things between Andy and I fizzled out. I think after the whole argument he felt I had been a little pushy. But we stayed in touch and most importantly remained friends. So when I found out that Andy had “come out” I was delighted. He called me up one day with the news that he had told Jack. Not only did Jack understand, but also he threw him a party where everyone had to come in cross-dress to make him feel more comfortable. I knew it would be hard initially and some of his “friends” did make some mean comments but over all people reacted the way I thought they would. With open-minds.

Now Andy is comfortable enough to turn up to parties in makeup and women’s t-shirts. But if I hadn’t given him the push he needed then maybe he would still be sneaking on the hairclips in private. Sometimes you need that emotional charge to get things started.

Photo of guy in heels by Shutterstock

Next Steps

  • Chat about this subject on our Discussion Boards.
  • Need help but confused where to go locally? Download our StepFinder iPhone app to find local support services quickly.


Updated on 29-Sep-2015