Tell Shelley Anne: Dating a Crossdresser

This interview originally ran on TGForum and was reprinted here with Shelley Anne’s permission.

By Shelley Anne Baker

I had been thinking about sharing this story, which is true. I thought, now’s the time because I had permission from the people involved.

A friend of mine, whose real name is Pam, wasn’t shocked when she found out her boyfriend, I’ll call him Luke, was in to crossdressing. In fact, she said she was relaxed when the truth came out.

When he finally exposed himself to her, all glammed up in a dress and makeup, she was all for it. In a way, being so vulnerable with her increased their sexual pleasure. Her main concern was if he was going to come out to their friends.

When  they first became attracted to each other, with her not being aware of Luke’s feminine desires, their relationship progressed surprisingly quickly. They had many things in common. He ended up staying at her house four nights of the week. There’s no other way to describe it other than it just felt right. Eventually, things got even more comfortable. Then, Pam got out of the shower one morning to find him trying on her hair clips. She brushed it off as curiosity.

But as these types of situations happened more and more frequently it became more and more difficult to pretend like there was nothing going on. A couple of times she even found him trying on her lipstick. She didn’t have a problem with it. She just wanted to know if he was a crossdresser or considering it. 

Pam decided to be subtle about finding out since she didn’t know how Luke would react. So, after a few too many drinks one night Pam offered to do his makeup. He said he loved the idea. Pam was surprised how casual it was. It genuinely felt so natural. Before Luke had the chance to change his mind, Pam gathered her makeup, hairspray, and other personal care accessories. Once she worked her magic, Luke looked great. Some people might find it hard to deal with but, personally, Pam said she thought it was sexy, especially with the red lip-gloss.

The makeovers became a regular night in for Luke and Pam. They had loads of fun experimenting with different clothes and styles. Pam said it was like going out with her best friend. The only thing that kept niggling at the back of her mind was that none of their friends knew. While Pam never thought it would be an issue, when she asked Luke about it, he would instantly change the subject and become completely closed off. 

Pam pestered Luke for months before she took matters into her own hands. Eventually, she turned to one of her close friends. She wasn’t judgmental and she listened with an open mind. Perhaps unsurprisingly when she told Luke he flew off the deep end. He felt Pam had betrayed his trust and gone behind his back. He left Pam’s house and stopped talking to her for almost two weeks. At the time, Pam couldn’t believe how unreasonable he’d been.

Luke finally came around after those two weeks. He said they needed to talk. Pam told him she was hurt after he gave her the silent treatment and he apologized for that. In fact, Pam felt like for the first time in their relationship he was open and honest with her. He told her that only his parents knew about his crossdressing. Unfortunately, when he opened up to them, they were quite critical and thought he was gay. Although they gradually came round and embraced him, he was worried that his friends would react in a similar way. 

He figured that boys would respond differently to girls. That’s why he’d told Pam. So, Pam finally saw it from his point of view. She felt terrible for outing him. With hindsight, Pam can fully appreciate that that wasn’t her story to tell. Frankly, as we know, it’s still a very taboo subject which a lot of people don’t understand. That can lead to a lot of unwanted and unsavory opinions. Still, Pam suggested that he tell his best friend, Wayne, an understanding guy who he had known for years. At least then he would have some support. He said he was open to the idea, but it would just take time.

Ultimately, things between Pam and Luke fizzled out. Pam felt after the whole argument Luke felt she had been a little pushy. But they stayed in touch and most importantly remained friends. A few months down the road, Pam found out that Luke had come out and she was delighted. Luke even called her up with the news that he had told Wayne. Not only did Wayne understand, but also, he threw him a party where everyone had to come in crossdress to make him feel more comfortable. Pam thought it would be hard initially, and some of his friends did make some mean comments, but overall people reacted positively and with open minds.

Today, Luke is comfortable enough to show up at parties in makeup and women’s t-shirts.  Pam says the entire situation taught her a lot about gender expression, why men crossdress and letting people come out on their own terms.