Telling Her

Lee and Susan had just returned to his place from a very pleasant dinner date, and had settled on the couch. After a bit of small talk there was a silence, broken only by Lee fidgeting. Susan started to wonder what was up with him. With his nerves jumping like crazy, Lee took a deep breath and began his little confession.

“Susan, I’ve really enjoyed being with you. You’re fun and interesting, and I think I’m falling for you. But there’s something I really need to tell you before we go any further.”

She looked at him apprehensively. Was this going to be something shocking?

“I have a need to… cross-dress.” There. He actually got it out.

Susan didn’t scream or get angry, but her expression indicated she was not happy about it.

“So…you like to wear women’s clothes? I think that’s kind of creepy.”

He was taken aback a bit. “I don’t know why you’d think that – they’re just clothes.”

“You’re gay, right?”

“What? No! How can you even ask, since we’ve been dating?”

“You must be. There’s no way a man can want to look like a woman without being gay.”

She paused and thought a bit. She was starting to get uncomfortable.

“I think if you want us to keep seeing each other, you’ll have to stop doing it. Actually, even then I’m not sure…this puts a whole new spin on our relationship.”

“Um, I’m sorry, Susan, but it’s not something I can just stop doing. It doesn’t work that way. It’s kind of a built-in thing. Have I acted creepy?”

“No, but now that I know about it, I can’t not think about it.” She thought for another minute, feeling more creeped out each second. “Sorry, I just don’t think I can handle this.”

She stood up and walked out of his life.

The two of them had been introduced by a mutual acquaintance, and had been dating for only a few months. Even so they were already getting serious about each other. There had seemed to be a deep understanding between them, at least Lee thought so. Well, until now. Unfortunately, the very fact of this level of seriousness had brought Lee to the old complication: telling her about his cross-dressing. Several years earlier he had decided that honesty was the best policy and would tell the dates he was getting really serious about that he was a crossdresser. The thought of actually marrying someone and then having her find out about this part of him seemed totally wrong. Even though to him it was just clothing, it felt dishonest, somehow, not to mention it. Susan was only the third woman he had told. The first two had gotten angry and dumped him cold after hearing about it, as if he had been stringing them along for some fiendish plot. But still, he continued to feel it was something they should be aware of if the two of them were going to get have a more consequential relationship.


Lee sat there a while, sadly looking at the space on the couch where Susan had been sitting. While he knew this had been a possible outcome, he had been hoping against hope it wouldn’t happen yet again. As he had told her, it wasn’t something he could just decide not to do, not without consequences. He’d tried stopping before, and it just felt like…like being deprived of something important to his well-being. It was so hard to understand why this was such an issue with so many women. He had truly liked Susan and was feeling very unhappy. He knew he needed to get on with life, but…ouch! It’s not like cross-dressing was his entire life—he was a three-dimensional guy, with likes, interests, etc. But the dressing was also important to him.

He also realized that, once again, he was fortunate, in that there would be no horrible scene later on, during the marriage, when Susan discovered this side of him and had a fit. Suddenly he was happy that they lived across town from each other, so the likelihood of running into her wasn’t too high, especially if he stayed away from the places they went together. As always, he wondered if she would be outing him to people she knew. So far he’d been lucky on that score, but you never knew…


Meanwhile, on the other side of town, Susan hadn’t given Lee a whole lot more thought. She had liked him a lot, but a man dressing up in women’s clothes had a big ICK factor for her, so she just closed that door. Fortunately she hadn’t yet quite given her heart to him.

Strangely, now it seemed as though wherever she turned she was seeing transvestites, on talk shows, soap operas, and some women she saw in shops or on the street, women she looked at more than once. Did they have Adams apples? Wide shoulders? A few of them caught her ogling them and gave her disapproving looks. One raised her eyebrows and looked interested, which caused Susan to hurry away.


Susan made the acquaintance of Hillary, a woman from work. They seemed to hit it off, starting with lunching together, and began to do other things with each other. Meals, movies, shopping. Susan gave her the usual once-over. She had kind of large hands, but otherwise seemed womanly enough, so she stopped thinking about it.

This evening they were at dinner at a restaurant, and had loosened up with some wine. For some reason Susan started to talk about her old boyfriend, and, in a rather disparaging way, how he liked to dress as a woman. Hillary’s face took on a stony expression. She asked Susan what had happened. Susan told her she couldn’t keep going out with him, he must be gay. Hillary asked, “Did the fact that he was dating you, a woman, ever make it into your brain? If he was gay why was he dating you? Are you saying you think that he regarded you as another man?”

To Susan that seemed just a little harsh, but she had somehow never thought of it like that before, even though Lee had basically said the same thing. She had no answer.

“So you dumped him only because he liked to wear women’s clothes? What do the clothes have to do with the person? Was he a terrible person? And if clothes are so important to you, what does it say about you if you wear pants? Or a man’s shirt?”

Susan’s mouth opened again, but nothing came out.

Hillary got to her feet, looked down at Susan, and said, “I had no idea you were so intolerant. You should get to know all sides of any story before you make a judgment.” She paused as if she was going to say something else. But all she said was “Be careful going home.” She left the restaurant.

Susan felt devastated and properly chastised. She really had made a judgment based on nothing at all. Maybe the attitude was drummed into her from church, or just from society’s mores. Men in dresses were jokes, a view enforced in countless movies and TV shows. If it wasn’t supposed to be funny, there had to be something wrong with them to dress like that, such as a disguise to commit a crime. Now that she started to think about it, when there was an obviously gay man on TV, he almost never wore a dress. But, she thought, if it’s only just clothes, pieces of cloth, why are they perceived as wrong or sick? Even if the man didn’t drag it up, with big boobs and overdone makeup and wigs, he was still a joke. The more she thought about it, the more confusing it got.

Once Susan was home, her mind was still filled with the subject. She thought for the first time about how heartless she must have seemed to Lee. She hadn’t tried to find out his motivations. Did he want to be a woman? She was pretty sure he said he wasn’t gay, but she hadn’t paid much attention, thinking she knew better.

Well, Hillary was right. She had no right to judge, and should learn more about all this gender stuff which seemed so prevalent nowadays. She did wonder if her friendship with Hillary was over…

She also wondered if she should contact Lee and apologize, but it had been quite some time, and he had probably moved on.


The next working day she sent Hillary a message asking if they could lunch together, and Hillary replied in the affirmative. At lunch Susan apologized to Hillary and thanked her for opening her eyes to how she had treated the old boyfriend.

“I never even gave him a chance to explain. I just shut him down and walked away. It’s too bad, because I really liked him. It was just that the idea of a man in women’s clothing kind of creeps me out.”

Hillary accepted the apology, and Susan asked her to help educate her about this sort of thing, about which she apparently knew little.

“Should it even matter what sex the person is?” she asked.

“I believe people should be treated as people, and respected for how they present themselves,” said Hillary, “rather than how society expects them to look. I’m sure not everyone agrees with me, but I have seen too many abused and disrespected simply because of either the way they dress or because they don’t identify with their birth gender. You should also be aware that the majority of cross-dressers are heterosexual.”

Hillary recommended some good quality websites for her to read to find out more. Susan did follow up with those sites, educating herself. She couldn’t help but wonder how many people she came across during each day were not what they appeared on the surface, including people closeted away within themselves. She still couldn’t help puzzling about Hillary and her large hands, until she realized that trying to find out Hillary’s birth gender would show she hadn’t learned much. She liked her for who she was.


Lee was starting to have mixed feelings about his love life. He was already thirty, and, being a sensitive man, wasn’t sure he could handle yet another rejection. He knew he would be unable to stop dressing. The idea of having a serious, loving relationship with someone while hiding this part of himself was not something he thought he could do. He had a few more dates, but with no one he found himself super interested in. He started toying with the idea of forgetting about love and only going on casual dates, simply for company. He did meet a woman, Laura, and they hit it off, but there was nothing sexual about their relationship…though he wouldn’t have minded. However, that would have eventually led to another confession and chance to be rejected. So he wasn’t going to push for anything more. They just went out as friends, and actually had some fun.

Though Lee was unaware of it, by a stroke of fate it turned out Laura was friends with some of Susan’s friends, and when a party was organized, Laura asked him to come with her, as her guest.

Susan was also at the party, spotted him and decided to come over and finally say how sorry she was for dumping him. He was pretty startled—and not very pleased—to see her there, but he was polite.

“Lee! I’m surprised but glad to see you here. I’ve been wanting to apologize for the way I treated you,” she said. “I was very ignorant about many things.”

“It’s water under the bridge, Susan,” he said, taking a drink. “How have you been?”

“Oh, pretty good, thanks. And you?”

“Not bad, not bad.”

“Are you seeing anyone?”

“No, not really. I’m here with a friend.”

“You know, I did enjoy our time together, Lee. I don’t suppose you’d be interested in trying again?”

“Nnnnno, I don’t think so.” She may have changed her ways, but he wasn’t going to give her another chance to hurt him.

She looked let down.

Lee, who had had just enough alcohol to loosen up, said, “Don’t look so disappointed. There are plenty of non-crossdressing men in this city. I’m sure you would have a lot to offer them.”

That seemed like a very left-handed compliment to her, but she didn’t feel like starting an argument with him, so instead walked back to one of her friends. Did she think he would jump at the chance to get back together? Maybe she did.

“What was that about?” asked Laura, coming up behind him.

“Oh, just someone who unceremoniously dumped me a couple years ago,” he said, swirling his drink around.

“What’d she want?”

“Actually she apologized to me.”

“Hm! That was nice of her.”

“But she also asked if I wanted to try again. I said no.”

“Are you sure you don’t want to?”

“Yeah, if she could act like that once, she could act like that again. Still, I tried to be polite.”

Lee was unaware that Laura had been close enough to hear the conversation. The “non-crossdressing” comment had piqued her interest somewhat. She didn’t mention it to Lee though. But now she was aware he’d been hurt in the past.


That night, as Lee lay in bed, he wondered if it was worth it to be social at all. He had never felt he was that great at socializing, and though it was nice that Susan had apologized, the whole subject was not one he liked to think about. Her bringing it up had brought back all those feelings which came from being rejected. Why couldn’t it just be a non-issue? For crying out loud, they were only CLOTHES! Maybe being a hermit would be a more ideal lifestyle for him. He could go to work and come home, and maybe go out here and there on his own. It would be fine. No one would be able to hurt him or reject him. He was so tired of having this secret he would need to explain to each woman he got close to. The dread of what her reaction might be didn’t do his nerves any good. So what was the point? No more close relationships!

Deciding to work his way up (or down) to the hermit life, he started hanging out at the library. The idea was to just talk with strangers and maybe casual acquaintances. At the library he’d find a book, then just sit and read, hoping someone would talk to him. But the library was not the best place to be striking up conversations, so it was essentially being alone in a public space. Not one person talked to him there. And he wasn’t extroverted enough to start conversations with strangers.

Next, he tried joining a volleyball team, which met at a local high school. There was camaraderie, yes, but it seemed like mostly what the guys wanted to do was go to bars when the games were over. Lee had no interest in bars, and though he was unaware of it,—and probably would have denied it—he was sending out “leave me alone” vibes, even as he hoped for conversation. So he was not included as he thought he would be. They’d greet him when they all arrived, and say goodbye, and that was about it.

Lee sighed to himself and decided to go Full Hermit. He wanted people contact, but wasn’t exactly sure what type that would be. He had vaguely imagined friendly conversations at coffee shops or something like that. He’d even spent some time at his local coffee shop, and it seemed that all people did there was park themselves at a table and stare at their electronic devices. Since he wasn’t able to bring himself to actually start the conversation, there were none. The two or three things he’d tried just weren’t working out as he had hoped.

The next time Laura called to suggest they do something together, he very politely thanked her and declined, saying he had other commitments. After this happened four times in a row, Laura got the message and stopped calling, although she couldn’t help but wonder what was going on with him. She had the feeling this had something to do with that woman at the party who had apologized to him. The third time he turned her down and said he had to go out, she drove past his place and saw the lights were on. Whatever he was doing, it wasn’t away from home, as he had told her.

He was testing out his new, solitary life. It wasn’t so terrible. After all, there were thousands of people who lived alone and had little contact with others. He did have some people contact, though, at his workplace. He decided that would just have to suffice. At home he dressed up as often as he liked. It wasn’t as if anyone he knew would be coming to the door.

He got a dog, Maggie, for company and to love, and walking the dog got him outside, which was good.

During the next six months he found out some of the downsides of being all alone. When his car needed repairs, and there was no one to pick him up; when he had to take a business trip and needed someone to take care of the dog; when he wasn’t feeling well and there was absolutely no one to turn to. Many of these things could be managed in other ways, like taxis, home deliveries and professional dog-sitting services, or a kennel. So yeah, he was lonely, but he was just tired of the worry and the rejection, and of the whole dating scene. Maggie kept his heart from sealing itself shut, but only just.


A couple of months into Lee’s self-imposed exile, Laura sat at her apartment, thinking about him. She liked him, and he was fun to do things with, even though they didn’t seem to have much chemistry. Thinking back to the conversation she had overheard at the party, it seemed likely he was a crossdresser. Did that bother her? He wasn’t exactly a feminine guy, and trying to imagine him in a dress didn’t work very well. However, she knew enough about cross-dressing to know that someone might easily do it out of need, rather than trying to go out and be accepted as a woman. No doubt that person at the party had dumped him when she found out about the dressing, which was why she felt she had to apologize to him. On balance, Laura didn’t think his dressing would bother her, and it might even spice up their relationship.

Building on that theory, she wondered if he was just tired of dating, because sooner or later his ‘hobby’ would probably come up. That might be why he started turning down her invitations. She wondered if there was something she might do for him…


By the time six months had gone by Lee was kind of depressed. Sure, he could dress up at home all the time—Maggie either didn’t care or had no opinion—but there was no one to share anything with. The hermit life was wearing thin, but he wasn’t really sure how to break out of it now that he was entrenched. He carefully stuck to a routine, so that he wouldn’t just sit on his butt all the time.

Meanwhile, Laura had been dreaming up scenarios to help Lee, and rejecting them one by one. The mere fact that she knew about his dressing would likely be hard for him to accept. How could she let him know it wasn’t a problem for her? If she just showed up at his place and he was dressed, she doubted he would answer the door. No, she’d have to find him outside. She drove by his place often, and finally one day she spotted him near there walking a little dog. He hadn’t had a dog when they had been seeing each other.

Dog walking seemed like a good time to talk to him. Noting the time she drove by a couple more times at the same hour and there he was again, with the dog.

Now that she had the how-to-meet part figured out, she needed to determine what to say when they met. Maybe just a regular conversation.


Laura was walking toward where she expected Lee to appear from. Aaaannd, there he was, with his dog.

“Lee! Hey, how are you?”

“Oh, Laura. Hi,” he said, with a notable lack of enthusiasm.

“And who is this with you?”

“This is Maggie,” he said, looking down at her.

“Hiya Maggie! Aren’t you the cutest thing,” she said, as Maggie started sniffing her.

“Lee, I haven’t seen you in months. Where’ve you been?”

“Oh, I, um, I’ve just been really busy.”

Well that sounded pretty lame, to both of them.

“Let me walk with you a little. I’ve missed you.”


“Why do you sound so surprised?”

“Oh. No reason.”

They started walking again, in the direction Laura had come from.

“Lee, are you okay? You look kind of sad. Talk to me.”

“No, I’m fine. Just haven’t had the opportunity to get out.”

She stopped and looked him in the eye.

“Lee, let me tell you what I think is going on,” she said, as kindly and gently as she could.

He wasn’t sure he was going to like this, but if nothing else, he was polite.

“I think you’ve decided to barricade yourself in your house and not go out because you’re worried about some woman finding out about your cross-dressing.”

Lee’s eyes widened, and he felt the blood rush out of his head. He’d been right; he didn’t like this.

“How…how do you know?”

“When you met that woman at the party—the one who apologized for dumping you—I overheard your conversation. I’m guessing she found out you cross-dressed and dropped you.”

Lee said nothing.

“Just so you know, Lee, I have no problem with cross-dressing.”

Lee’s system was still in shock from her revelation. He wanted to run home and hide. This wasn’t a rejection, but it was as though a part of him had been sliced open so others could look inside, and it brought back the same unpleasant feelings as being rejected. He didn’t really know how to deal with this.

“I…I…I have to go,” he muttered. He turned around and he and the dog were practically running back towards his place.

Laura’s shoulders sagged as she looked after him.

“That poor guy. How could I have said it any differently?”


Back at home Laura wrote a brief snail-mail to Lee.

Dear Lee,
I’m sorry if I upset you. I did really mean it, though, that your, um, hobby doesn’t bother me in the least bit. It might even be fun to share. I find it sad that you’re shutting the world out. You’re a very nice guy and I enjoyed doing things with you.
Please reconsider about the shut-in lifestyle.
Your friend,

She dropped it in a mailbox that same day and hoped for the best.


By the time Lee got the letter he was feeling a little better. It was a kind note, and without the pressure of her being right there, he found he really appreciated the gesture. If he started going out with her again, he might well find himself back in the same conundrum he always faced, but at least with one friend things might not look so bleak. And she sounded as if she might actually want to see him dressed. He wasn’t sure just how ready he was for that, but…

He picked up the phone and started to call her.

The End.

--Frankly I have no idea what this is. The longer I worked on it, the less I knew what it was about. Maybe we can call it a story fragment.

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