We were flying home, 35,000 feet in the air, after what had turned into a traumatic few days for me. It was an uncomfortable flight, sitting between two of my ex-coworkers. I sensed that Gail, my favorite co-worker, wanted to talk to me, but the boss was such a control freak—which was why I found myself in this position—I guess she didn’t dare. What I was fretting about was what I was going to do with myself once we got back home, since I no longer had a job.

You’re probably wondering why I was fired. Me too.

We—that is me and four of my female co-workers along with our supervisor, Ms. Fox—had flown to Chicago for a conference at which we were to give an important presentation to a potential client. Although I was the newest and youngest of the bunch, I still had something to contribute, since I had worked hard on the campaign.

Four days earlier – the trouble begins

When we touched down at O’Hare Airport we all congregated at the baggage carousels, waiting for our suitcases. It had been a full flight on a 747, so there was quite a lot of luggage going by. When I saw mine finally coming along—one of the last—I grabbed it, but thought it was odd that my ID tag had come off. Once everyone had their bags we got a car service to the hotel, right in downtown Chicago on Michigan avenue.

We were all given our own rooms, which was pretty nice of the company. Ms. Fox, who was a bit of a martinet, and always talked about “running a tight ship,” said we would all meet for dinner and discuss our upcoming presentation one more time.

Dragging my suitcase into my room, I flopped onto the bed. Flying, for me, is always an ordeal. There’s never enough room, even if you happen to be short. Even with no room they still let you recline your seats! The guy in the seat in front of me was practically in my lap, and I was able to memorize his bald spot—not that that will do me any good! The noise, the delays, the close quarters, etc., etc… it was all exhausting and practically made me sick. I got in a little nap before it was time to get ready to meet for dinner.

Thinking I’d change to something a bit more formal than my traveling clothes, which were a casual short-sleeved shirt and khakis, I unzipped the suitcase. Then I just stared at the contents, which were definitely not my clothes. It was filled with tops, skirts, dresses and lingerie.

I looked the suitcase over again. It sure looked like mine, even down to a big scuff mark I remembered making a year ago. Carefully digging through the contents, I could find no identification of any kind.

Well, this was just great! I didn’t have money to buy any new clothes; I barely had enough for food as it was. What I was wearing would surely not be acceptable to Ms. Fox.

Looking at the clock, I decided there was enough time to report this to the airline, so I made the call and described what had happened. They told me there was no unclaimed baggage there, but they’d call me if they heard anything. TerRIFFic!

This didn’t seem like it was going to end well for me, knowing Ms. Fox as I did. She always treated me coolly, although I had never been anything but pleasant to her.

Sighing, I went to the sink and tried to smarten myself up a bit, look somewhat less like a person who was rumpled and tired from a plane ride.

-o0o-

We were all on the same floor, and met at the elevator lobby at 6:30. My clothes were noticed immediately by all the women and Ms. Fox. Some of them were wincing, knowing what was probably coming from Ms. Fox.

“Mr. Hallet, I expected something more formal.”

She never, ever called me by my nickname, Matty, or even Matthew, my given name; always Mr. Hallet. (No one ever called her anything but Ms. Fox; I’m not even sure she had a first name.)

“Well, I’m sorry, Ms. Fox, but it turned out the suitcase I got was not mine. I have nothing to change into,” I said, as pleasantly as I could.

She looked at me as if I had grabbed the wrong bag on purpose.

“Is there not something in the bag you got that you could wear? What about our presentation?”

“Uhhh, I’m afraid not. The fact is that the suitcase contains only women’s clothes.”

Her eyebrows went up.

“And why can’t you wear those?”

Stunned, I waited for a response to filter into my brain. “Well, for one thing, I am not a woman, and it wouldn’t be appropriate. For another, even if I was interested I have no idea if they would fit.” Hmm. It was probably a mistake to say that.

“The size seems easy enough to determine. Why don’t we go back to your room and find out?”

That was more of an order than a question, and I automatically obeyed. We all trooped back down the hall to my room. I opened the door, and all the women came inside. The flap was still open on the suitcase, and Ms. Fox went right over to it and began pulling things out. She held a dress up close to me.

“Size fourteen for most of this. That should fit you, Mr. Hallet.”

“Ahhh, Ms. Fox, I’m not going to wear women’s clothing,” I said, not in a belligerent way.

She looked at me icily.

“And why not?”

“I won’t be party to a deception, and I don’t want to look like an idiot. What’s wrong with the clothes I have on? We can just tell the client the truth, that my luggage didn’t make it.”

“That’s not acceptable.” She gave me an appraising look. “You are skinny and not all that manly. It would not be implausible for you to present yourself as a woman. And I don’t see this as a deception; you would simply be wearing different clothes.”

Ignoring the insult, I said, “It may sound simple to you, Ms. Fox, but I’m not willing to make a clown out of myself, especially for something as important as this.”

She looked at me for some time, and then said, “I see. You know, Mr. Hallet, this presentation is a very significant account for the company. It’s hard to imagine you keeping your job if you refuse.”

I swallowed. I did need the job, but not that bad.

“I’m sorry, Ms. Fox, but I won’t wear these clothes and pretend to be a woman.”

The others had just been standing there, uncomfortably observing this back and forth tussle. I couldn’t interpret Gail’s look. We could all see where this was going.

Ms. Fox drew herself up to her full 5’10” and looked down her nose at me. “You can consider yourself fired then. Let’s go, ladies.”

And she led them all out of my room.

-o0o-

So that’s how I lost my job. Now I was in Chicago with three free days to myself and almost no money. I couldn’t think of one person I knew who lived in the area, someone I could call for help. How could something this dumb have happened?! Any appetite I may have had was gone, so I thought I might as well skip dinner and save my money for the rest of my time here. It was a huge relief that the hotel room was already paid for. Otherwise I wouldn’t have been at all surprised if Ms. Fox got me kicked out.

Getting comfortable, I sat on the bed and watched the television for a few hours. As it got later I realized it would make sense to try and clean my t-shirt and underwear in the sink, since I was going to have to keep wearing them.

After that was accomplished to the best of my ability, I got into bed, but just lay there worrying. It hadn’t been easy to find this job, and I did not look forward to another round of resumés and interviews. That had been nightmarish, with some of the looks I got. I didn’t have any disfigurement or anything, but I was young and not terribly tall. They just looked at me like they didn’t believe I’d be able to do the job, even if it was office work.

Around 10 p.m. there was a quiet knock on my door.

“Um, give me a minute,” I called. I hurriedly pulled on my pants and shirt, and went to open the door.

Gail stood there.

“Gail!” I exclaimed, as if I hadn’t seen a friendly face for months. “Please come in,” I said, standing aside for her.

“Matty, I’m sorry about Ms. Fox. She had no right to fire you over this.”

“Yeah, well… Frankly, I don’t think she has ever liked me, though I don’t know why.”

“Oh, that’s easy; she’s a Lesbian of the man-hating variety.”

Why hadn’t that occurred to me?! If I thought about it, she did seem to be equipped with an invisible Man Repeller.

Gail glanced at the suitcase. “You’re sure you don’t want to try these clothes?”

Looking at her to see if she was kidding, I saw nothing but sincerity.

“Umm, no, not my first choice.”

“I didn’t think so. But… what if it meant you’d be able to get your job back?” She looked very hopeful.

“Oh, Gail, I really don’t think Ms. Fox is the kind of person to change her mind because I capitulated after the fact.”

“No, you’re probably right,” she said sadly.

There was a silence.

“Well, you know what, Gail? There must be some reason for this, some cosmic plan in action.”

She looked at me skeptically.

“Hey, I have to tell myself something for it to make sense!”

She smiled a little.

“Good attitude,” she said. “Listen, I just wanted to see you and tell you I’m sorry.”

I smiled back at her.

“Thanks Gail. That means a lot.”

“Good night, Matty.”

She left and I smiled. I’d always liked Gail, and she was very attractive. Maybe if I’d been a little older and financially secure I would have asked her on a date. Aww, who was I kidding? I would have thought about asking her out, but never done it. I would miss working with her.

-o0o-

The next two days I walked my feet off in the downtown area, mostly on Michigan avenue. I stopped in at some of the hotel lounges to rest, and I spent a lot of time at the Art Institute and the library of Roosevelt University. For food I found a little mini market and got a loaf of bread, and peanut butter and jelly for sandwiches, but I felt starved most of the time. My finances were not in the best of shape, and back home I had a lot of items to pay off, which is why I had so little cash on me.

The second day it rained, hard, and I got much wetter than I would have liked. I passed a couple hours in one of the hotel lounges, waiting for the rain to stop, but other than people-watching there really wasn’t anything for me to do there. When the rain tapered off somewhat, I was walking back to my hotel in the late afternoon when a car swerved close to me, literally showering me with filthy water. This was like the icing on the cake of this whole trip. The driver never stopped. I stood there dripping, looking after the car, thinking, ‘This just keeps getting better and better.’

Squishing my way back to the hotel I got some looks as I went through the lobby, doing my impression of a drowned rat. Back in my room I stripped off and took a nice, hot shower. Then, wearing the towel, I tried to wash out my pants and shirt. Wringing the pants out I soon had a painful blister on the webbing of my thumb. Sighing, I draped the clothes over the shower rod and then assessed them. They didn’t look much better than before the washing. Hardly any of the dirt seemed to come out, and there was no way I could afford to have them cleaned. But I was sure they’d look just fantastic once they dried, I sarcastically kidded myself.

When I came out of the bathroom my eye fell on the cursed suitcase. Could there be something unfeminine in there? Slacks? Shorts? Rummaging through it I found nothing resembling pants. I did find a long-sleeved purplish blouse that looked feminine, but not ultra-feminine, along with a pair of panties. Thinking that would be enough to wear until my clothes dried, I put them on, sat on the bed, and put my legs under the covers.

Watching what passes for TV got old after a very short period of time, and I felt antsy, so I got out of bed and started pacing. It was too cool in the room for someone with no pants, and, heaving yet another sigh, I pulled a knee-length skirt out of the suitcase and put it on. I felt totally ridiculous, like I was an adult dressing up for a kids’ Halloween party. Avoiding the big mirror in the room I resumed my pacing, but to my displeasure noticed I was beginning to like the sensation of the skirt lining brushing against my legs. So soft…

About this time there was a soft knock on the door, and I froze.

“Matty? Are you in there?” I heard Gail’s voice.

Was I going to let her see me like this? Wouldn’t it make me look like a hypocrite? But really, what the hell. My life was already in the toilet; what was one more humiliation?

Hiding behind the door I opened it and invited Gail in. Once she got a look at me her face went through several interesting expressions, and she opened her mouth to speak.

“Before you say anything,” I interjected, “I was splashed by a car this afternoon, really filthy water. I wasn’t going to wear a skimpy hotel towel or a sheet until the clothes dried.”

She giggled at that.

“I think you look very nice. I just wanted to see how you were getting along,” she said.

My heart warmed at her caring. “Thanks. I’m doing okay, I guess. I can’t tell you how many times I’ve been up and down Michigan Avenue…. The Art Institute is really nice… Just kind of waiting until it’s time to fly home and start looking for a job.”

She looked surprised. “Aren’t you going to fight Fox to get your job back?”

“Gail, I’m not very good with arguing or defending myself. She probably has some in with the Human Relations department, and could figure some way to get me, like, even more fired than I already am.”

At that moment my stomach made a pretty loud rumble, and her eyebrows went up.

“Have you been getting enough to eat?”

“Uh, yeah. I bought bread and stuff for sandwiches.”

She looked at me skeptically for a while.

“What if I were to take you out to dinner?” she offered.

I was about to jump at the chance for her company, and some decent food, but realized I had nothing I could wear.

“Oh, um, thank you very much, but my clothes still aren’t dry.”

She looked me up and down at that, making me feel…assessed.

“Listen, Matty, I know you probably don’t want to hear this, but I think you could pass as a woman without too much trouble. Those clothes look good on you, and you don’t even have hairy legs.”

As a red-blooded male, this wasn’t something I really wanted to hear. I knew she wasn’t saying it to be mean, but it was just a different way of saying, “you are not manly.” I mean, I knew I was no stud, but I’d be terrified trying to pass myself off as a woman. Somewhere deep inside I just knew it was wrong to put on a woman’s clothes.

“Come on, be brave,” she coaxed. “It’s getting darker outside, so no one is going to be looking at you. And I hate to tell you this, but I’m not even sure your clothes will be dry by tomorrow.”

That hadn’t occurred to me. I sure didn’t want to be stuck in this room all day tomorrow.

“Let me take a look at them, okay?”

I led her into the bathroom, and she looked appalled at the state they were in.

“Matty, you’re going to have to take these to the cleaners. The dirt’s still there, and they’re going to look awful once they do dry.”

Sighing, I said, “Gail, I don’t have the money to have them cleaned; I hardly have any money at all.”

“Okay then,” she said, “I’ll pay for them to be cleaned and you can pay me back when you’re able.”

That didn’t sound too bad, although I had no idea when or where my next paycheck would be coming from.

“But you do realize I won’t be able to take them there and get them back for you, right? The conference doesn’t end until tomorrow afternoon. You would have to go out wearing something from this suitcase.”

Blanching, I felt my stomach drop.

“I, I don’t know if I can do that, Gail.”

She looked at me sympathetically. “Well, if you come to dinner with me now, you can get a feel for how you would do by yourself.”

“Omigod, omigod…” I muttered. I wiped my face with my hand, feeling sick.

She put a hand on my arm.

“Look, let’s see what you look like with some makeup and a different hairdo, okay? Then you can think about if you can do this.”

Against my better judgment I sat down and let her change my hair and put some makeup on me. My hair wasn’t that long, but apparently it was long enough for her to make it look somewhat feminine. When she was done, I didn’t look quite as masculine, and thought it was amazing how much effect just the hairdo had on my appearance. That’s what really sold the illusion. She also dug in the suitcase and brought out a bra, which she helped me on with, me all the time thinking I must be totally nuts to do this. She filled the cups with some knee-highs that were in the suitcase. That helped the illusion too. When she looked me over I saw something flicker in her eyes. I wasn’t sure what it was, but she seemed to be breathing faster.

“So, what do you think?” she eventually asked.

“I think this is a very bad idea, but since it’s kind of an emergency, I’m going to put my total dread aside and go with you.”

She smiled. “Good. I like the way you look. Very…fetching.”

I did not know how to take that remark.

“And just think what might have happened if the woman who owned this suitcase was a size XXXL!”

Rolling my eyes, I said, “Just…please stay close to me.”

Her eyes sparkled.

-o0o-

All I will say about the subsequent walk to the restaurant, the meal and the walk back—other than the fact that it was nerve-wracking—was that I wasn’t questioned, or looked at funny. I really don’t think many people looked at me at all. If they weren’t paying attention to their phones, they were talking with each other, or looking down at their feet as they walked. That gave me a little confidence. And at the restaurant even the waitress didn’t betray any confusion about me. Still, I was incredibly relieved to get back to my room.

“See?” said Gail. “You survived just fine.”

“Just barely, Gail, just barely.”

“I’ll come here early tomorrow to help you get ready,” she said, as she was about to open the door to leave.

“Gail, thank you so much; you’re a life-saver,” I said, stepping forward and giving her a little hug.

She smiled hugely at that and left.

Then it occurred to me I had never hugged her before, and I wasn’t even exactly a huggy person. I would never have presumed to just hug her like that. That was interesting and confusing.

-o0o-

Finally, the last day here arrived! Gail was as good as her word, showing up around 7:15 in the morning. She picked out a different blouse and skirt for me, helped with the makeup and hair, and then gave me money for the cleaning bill. I thanked her profusely.

Calling the front desk for information, I was told there was a dry cleaners several blocks north and one block in, on Erie street, so I put my clothes in a plastic bag and, steeling my nerves, walked over there to drop them off for a rush job.

I’ve always been a good mimic, and speaking as little and as softly as possible I used a very feminine voice at the cleaners. No one questioned me, or looked at me funny. Gail must’ve done an incredible job on me. Still, not wanting to test this appearance any longer than necessary, I quickly walked back to the hotel and wasted time in my room until it was time to go back for the clothes. It was still nerve-wracking to be outside dressed like this, even if no one pointed at me and started laughing.

A few hours later, after having picked up my clothes, I was carefully making my way back to the hotel when who should I see coming toward me but the tall, thin, ramrod form of Ms. Fox. Her eyes widened when she saw me, then she smirked and spoke in a superior tone.

“MISS Hallet, I see you have decided you can be party to a deception.”

I stopped and looked at her as I would at a rude stranger, hoping this would work. At the back of my mind I wondered why she insisted on being called Ms., but used Miss on me.

“I beg your pardon,” I said in outraged tones. “Are you addressing me?” Using my powers of mimicry, I spoke in Ms. Fox’s somewhat unpleasant voice. After I first met her I was able to do a pretty good impression of her. Now, I threw in a slight British upper-class accent.

She was taken aback somewhat. She probably didn’t recognize her own voice coming back at her, but she certainly must have thought it was a real woman’s voice. She looked at me more closely while I tried not to tremble. I kept glaring at her and looking affronted at this accusation. Finally she backed down.

“I… I’m sorry. I thought you were someone else.”

She said this so humbly I could hardly believe it came from her. I just gave her another glare and went on my way. We weren’t so close to the hotel that she would have seen me go inside, thank goodness.

-o0o-

It was great to get back into my own clothes; I felt so much less like a fraud. In spite of Ms. Fox’s attitude, when it was time to leave the other ex-coworkers welcomed me into the car service that took us back to O’Hare. At the airline desk I asked once more about my luggage, but there was no news. That didn’t even make sense! Somewhere there was a woman who had all my clothes, and… what? It was no problem at all for her?

Shaking my head, I checked the suitcase I was stuck with, we eventually boarded and flew back home.

At our home airport I again picked up that same, stupid suitcase. During the flight I’d been hoping aginst hope that somehow the process might reverse itself and that my suitcase would magically reappear. If you’re wondering why I brought it home with me, there were a few things in there I thought I should have cleaned before it got returned.

Saying goodbye to Gail, I thanked her again warmly for all her help, (out of earshot of Ms. Fox, of course) and caught a bus to my apartment. I didn’t know what to do with the suitcase, so I just left it against the wall by the door. When the airline called to tell me they had my own case, then there could be a swap.

The next day I started job-hunting.

-o0o- -o0o- -o0o-

Gail thought to herself that she wasn’t just going to let this matter of the firing go. She liked Matty very much. He was young and pretty, but he was also moldable. Plus, she was sure there was something illegal about being axed like that. She quietly gave a detailed account to HR of the circumstances under which Matthew Hallet was fired. She included the names of the co-workers who had been present, if any corroboration was needed.

Two days later Ms. Fox, to her surprise, was called up to HR. She was summoned to the office of Craig Nolan. ‘A man,’ she noted to herself.

“Please have a seat, Ms. Fox. Now, I understand you fired Matthew Hallet while you were in Chicago?” the man said.

“Yes, I did,” she said, in a smug way.

“Please describe the events that led to this,” he requested.

She looked a little unsure now, but started recounting the story.

“We had arrived at our hotel, and were due for a dinner meeting of our group at a nice restaurant. Mr. Hallet appeared in his casual traveling clothes. I informed him that they would not do, and he told me he had gotten the wrong luggage at the airport.”

Mr. Nolan nodded. “Please continue.”

She shrugged. “I asked if there wasn’t something in that suitcase he could wear, and he said no, it was all women’s clothing. I didn’t see what difference that made. He also said that he didn’t even know what size it all was. We all went to his room, where I determined the sizes, said it should all fit him, and that he would be able to pass as a woman.”

“I see,” said Nolan, with one eyebrow up. So far this jibed exactly with Gail’s story. He tapped a finger on his desk several times, then looked back at her. “Did he agree then?”

“No, he emphatically declined to be what he called a party to a deception. I did not see it as a deception; just someone wearing different clothes. He certainly couldn’t represent our company in his rumpled casual clothes. So when he said no, rather childishly, I thought, I fired him.”

Mr. Nolan looked down at his papers and sighed. Then looked directly at Ms. Fox.

“Ms. Fox, you had no absolutely no authority to fire him for that. It was an unreasonable request on your part to ask someone to portray another gender.”

She didn’t see what the big deal was, and looked perplexed.

“You have put this company in a difficult position. There were many other solutions available, not least including him buying different clothing. He could sue us for wrongful termination, and he would win.”

She was beginning to get a cold feeling in her stomach.

“We will offer him his job back in exchange for not suing us, but this is not the first complaint against you, Ms. Fox. We have stood up for you in the past, because you’re very efficient, but this violation is too serious to pass. We’re… letting you go.”

Ms. Fox was stunned. They were letting her go just because some man didn’t want to wear a dress?

“Your final pay will be deposited in your account by the end of the work day today, Ms. Fox. Please collect any personal items from your work area and you will be escorted from the premises.” Mr. Nolan went back to some paperwork on his desk. She was obviously dismissed.

She unsteadily got up, torn between anger and confusion, and slowly left the office.

-o0o- -o0o- -o0o-

Five discouraging days after getting home I received a phone call from the HR department of my former job. They informed me that my firing had violated some kind of regulations or laws, and that they would be happy to have me back, especially if I agreed not to sue the company for wrongful termination. I was also promised a nice little raise from my former salary.

It all sounded pretty good. Other than Ms. Fox I had enjoyed working there, and it would be nice to see Gail again on a regular basis. I agreed to the terms, and was told to report to HR first thing Monday morning.

-o0o-

My old department welcomed me back very warmly, as if I had been away for months. Gail seemed especially glad to see me, and she gave me flowers as a welcome back present, which was a little embarrassing. Wasn’t it only women who got flowers? But I decided they looked kind of nice on my desk, so I left them. It surprised me to learn that Ms. Fox was no longer with the company. The ladies assured me she had been fired for firing me! That was a surprise. The guy in HR hadn’t mentioned that.

During my first week back I was invited to go to lunch with my little group more than once. They’d always been quietly nice to me, but this was the first lunch invitation I’d gotten. My impression was that before they were afraid of showing me any attention while Ms. Fox was hovering. So maybe they were making up for it?? There wasn’t much I could add to their conversations; after all I was younger, and a man, but Gail kept asking for my opinion on this or that. I enjoyed myself.

-o0o-

And then one evening my doorbell buzzed, and who should it be but Gail! I couldn’t imagine why she’d want to come and see me. But of course I smiled and invited her in.

“I’m glad things worked out so that you got your job back, Matty.”

“Well, me too! I was running pretty low on cash. I’d gone on a couple interviews that week after we got back, and no one was interested. I guess I don’t have enough experience.”

She took a step closer to me. “I missed you that week.”

“Me? I’m just the new guy.”

“New or not, I’ve always liked you,” she said, taking another step closer.

“I’ve, uh, always liked you too, Gail,” I said, a little unsettled by how close she was.

Taking one more step she was now standing so close that I backed up until I was found I was against the wall. She followed and stared into my eyes. I started to feel like I was having trouble breathing. She put a hand on my shoulder.

“I thought you looked very attractive when you were dressed in that skirt and blouse, Matty.”

That was unexpected. “Oh, um, thanks?”

“Tell me, Matty, have you ever had a girlfriend?”

Something about her proximity and her gaze was making my heart beat faster.

“Well, uh, I went out with this girl, Eleanor, during eleventh grade… a few times.”

“But she wasn’t really a girlfriend, was she.”

“Well, sort of?”

It seemed to be getting warmer in the room.

“Would you…like to have a girlfriend?” she asked, moving so close our bodies were now touching, and speaking in what seemed like a very seductive way. I was starting to feel pinned to the wall like an insect.

“Ah, ah, um, well sure, yes,” I answered. Having a beautiful woman so close to me was not something I could say had ever happened before, and it made me very nervous.

“And so would I,” she said, still staring into my eyes.

Oh. She doesn’t like men. That made me feel sad. “I’m uhh… I don’t see how I could help you with that, Gail.”

“You definitely could help, Matty, because you are the kind of girlfriend I would like.”

I heard those words. They did go into my head but they didn’t make a whole lot of sense there. Maybe there was a short circuit in one of my transistors? While my head was trying to deal with the meaning, Gail leaned forward and kissed me on the lips. It was as if electricity passed between us, making my eyes fly wide open in shock.

“What’re you… I mean… you… huh?”

She put her arms around my waist and said, “I really liked the way you looked when you were all dressed up in Chicago. I mean really liked it.”

The idea that a woman would find a man dressed like a woman attractive was a foreign concept to me. I mean, she knew I was a guy, but liked it that I had looked like a woman? You’d think that would mean she was a Lesbian, but if she knew I was… I just didn’t get it, and the confusion was evidently showing on my face.

“Women sometimes like to dress up and look good, not just for men but for ourselves. But Matty, women are not the only people who can look pretty in dresses, and with makeup on. Why shouldn’t a man be able to look pretty too?”

She gave me a couple more kisses, temporarily derailing my thoughts.

“Uh, well, you know, men aren’t really supposed to look pretty.”

“Why not?”

It was hard to think of the answer to that. Didn’t everyone know that men were supposed to be handsome and rugged, and only women were supposed to look pretty, or beautiful?

Gail wasn’t going to wait for me to come with a response. She squeezed me and kissed me and I just melted into her arms. In eleventh grade, Eleanor Ford had once given me a sort of slow peck on the cheek, but that was it. I had liked it, but this was sooooo much better than that. I kind of lost track of my surroundings as she kissed and caressed me. If I had been able to think straight, I would have realized I was in over my head.

Without me being quite aware of it, she had grabbed the rogue suitcase and maneuvered us into the bedroom. While she removed my clothes she continued to kiss me whenever her lips came close to mine. In my state of half-awareness, I assumed this was a prelude to sex.

I was wrong.

She was able to get me to cooperate somehow, in putting on panties and a bra. It was all done slowly and lovingly, making it somehow seem natural. Then she found a yellow summer dress from the suitcase and put it over my head, putting her arms around me to zip it up the back. I didn’t really understand why I was being so complacent, but then, my senses were pretty much on overload. She then gently sat me down on the bed, telling me to stay right there. She went back to the living room and retrieved a bag, out of which she began drawing cosmetics and then applying them, while I bemusedly watched her.

When she had finished her magic, and rearranged my hair, she showed me my face in a small mirror. It sure didn’t look like me!

“There’s my girl,” she cooed.

My wits were starting to reconstitute themselves. What in the world was I doing? Did I really want to be her…girlfriend?

She sat down next to me and put an arm around me, distracting my thoughts. It felt pretty nice to be held. But I felt like I was going to implode.

“Oh, I…I don’t know about this, Gail.”

“Shh,” she said, caressing my cheek. “You’re like the answer to a dream, Matty. I always liked you and the way you acted around all of us at the office. You were always polite, respectful, and you seemed very gentle. And I thought you were kind of cute! But when I saw you in that skirt and blouse… Wow! I was in love!”

Love? This was all news to me. I never had any inkling that Gail had any interest in me at all. After all, she was older, a little taller, a lot more worldly. Maybe I was simply clueless, but it was hard to see what could have been attractive about me.

“And when we went to dinner together that night you looked so good it was hard for me to keep my hands off you,” she said, squeezing me again.

She kissed me, hard, then, and jammed her tongue past my teeth and began massaging my tongue, my teeth, the roof of my mouth.

My emotions were whirling so fast it felt like I might start hovering above the bed. This older woman I liked had taken a big interest in me, although I’m not sure how accurate that is, given what I looked like now. It seemed like… some other Me. No one had ever looked at me the way she was looking at me. I’d never been hugged like this—like I was valuable—and I admit I was loving it. The attention she was giving me was starting to erode my feelings about this being wrong.

“How come, um… how come you never said anything before?”

“What, and incur the wrath of Fox? No, it wouldn’t have been safe for either of us. I’m actually so glad you picked up the wrong suitcase, and things worked out the way they did, since the end result is she’ll no longer be micro-managing us. What a terrible atmosphere she created! But thanks to you sticking up for yourself, we’re free from her restrictions and oppression.”

I thought back to that scene. There I was, standing up for myself, refusing to wear women’s clothes, and now look at me! Funny how things work out sometimes.

She got up and pulled me to my feet. “I want you to see something,” she said, leading me into the bathroom. We stopped in front of the mirror. She had her arm around my waist and had pulled me close. In the mirror I saw two women, one slightly taller—a knockout—holding the shorter woman possessively. Regarding the shorter woman, I kind of liked the way she looked. She was no supermodel, but had a kind of girl-next-door quality I found attractive.

“See her?” asked Gail.

I nodded slowly.

“That’s my girlfriend right there,” she said, waving a hand at the woman in the mirror, and leaning her head against mine. “She looks nice, doesn’t she?”

“Um, yeah, I guess so. She might look a little scared, too.”

“She’ll get over that pretty quickly, I think.”

I looked up at her. “Gail…”

“Yes, my pretty girlfriend?”

For some reason that gave me a little shiver.

“How…how is this supposed to work?”

She led us back into my living room and we sat down on the couch, with her arm still around me.

“It’s simple: you’ll be Matthew at work, and when you get home you’ll be my Matty. We’ll spend lots and lots of time together, really getting to know each other,” she said, sounding very happy. She nuzzled my neck as I sat, trying to think.

It sounded anything but simple to me. I really did want to get to know her; I just wasn’t convinced I wanted to leave my manhood behind in order to do it.

She launched us into another heavy petting session, and the only thing I could think was how wonderful it all felt. I felt very submissive as she ran kisses all over any exposed flesh I had. She was in complete control, and my body responded to her as she played it like a harp.

When she had exhausted herself she just held me, arms wrapped around me, our heads together. We sat contentedly in silence for a while.

“Gail, is the part where I put on women’s clothes really necessary?”

“You don’t like women’s clothes?”

“Oh, no, I mean, they look really great on women. But I’m not a woman.”

“Have you already forgotten how cute you looked in the mirror, Matty?”

“Oh. Uh, no.”

“So what does it matter if you’re not a biological woman? You look so good in skirts and dresses, and it makes me very happy. I wouldn’t be here right now if I hadn’t thought so in Chicago.” She gave me a little extra squeeze.

I had to admit I was glad she was happy, and there was something telling me that I wanted to please her. I made a big effort and dumped all my fears and misgivings right then, just imagining tossing them in a trash can.

Then I squeezed her back, kissed her, and said, “I will be happy to be your girlfriend, Gail.”

She gave me the biggest smile in the world and pulled us together so strongly I thought we might merge.

-o0o-

In a small hunter’s cabin in the Dutch Gap Forest Preserve, in Illinois near the Wisconsin border, an abandoned suitcase with no ID tag sat on the floor. There were some men’s clothes inside, but it would be months before anyone found it. When they did, no one could figure out where it came from. They would donate the lot to the Salvation Army.

The End.