Robin
It’s not that easy to walk on grass and gravel in stiletto heels. It took me a while to be able to navigate in the heels at all, and this terrain wasn’t helping. It was a divided two-lane rural highway, and there was no sidewalk. Walking in heels can really slow you down, too.

But hey, no big deal – only sixty or so miles to go!

Was it only a few hours ago that I was forced into this position?

-o0o-

There was no warning that my new girlfriend, Marian, had a cruel streak, but when it did show up this morning I couldn’t believe she would treat me like this.

Yesterday, Saturday, she took us for a nice ride, sixty, seventy miles from the city, just cruising along country roads and admiring the scenery. We took our time, stopping at nice vistas, did a bit of shopping, had dinner, and in general spent a pleasant day together. By the time we were finished with our meal, she had decided we’d get a motel room for the night. It was a decent place, close to the highway, with a cluster of shops nearby, across a plaza.

Marian was well-to-do compared with me, so it was her car (I didn’t have one) and she paid for the motel.

The big surprise came when I woke up this morning. When I opened my eyes it was to see Marian completely dressed in my clothes, and reading a magazine at the desk.

“Morning,” I said, rubbing my eyes. “Um, what’s going on? Are you wearing my clothes?”

“Morning, Robin. Yes, I am. I decided I wanted to be the Man today. Since your clothes are always a little baggy on you, they fit me pretty well, don’t you think?”

Looking at her sitting there, I had to admit it. “Well, yes, they do. But what am I supposed to wear?”

She laughed. “You’ll wear my clothes, of course.”

I wasn’t very amused. “Whoa there. That doesn’t sound like a good idea. I don’t want to wear your clothes.”

“Well, that’s too bad, since they’re the only clothes available.”

This was perplexing. Why was she acting this way? I knew she had a strong personality, but in the short time we’d known each other, this side of her had not been at all obvious.

“I don’t understand why you’re doing this. If you want to be ‘the man,’ whatever that means, why don’t we just go buy you some men’s clothes?”

“No reason to, when your clothes will work perfectly well. Besides, I want to be The Man in relation to you as my Woman.”

“But, but, I didn’t say I wanted to be ‘The Woman’ today!”

“That’s true, but that’s what I want, and you’ll go along with it, won’t you.”

That was not spoken as a question. And I could feel the ‘or else’ hidden there.

“You’re not leaving me much choice.”

“Nope,” she said, pleased with herself. “Anyhow, it’ll be fun to see what kind of woman you make.”

That didn’t sound like my idea of fun.

“Go take a shower and wash your hair and I’ll help you dress. And use the conditioner.”

I reluctantly got up and went into the bathroom. Strangely the only soap and shampoo in there this morning were for ladies. I went ahead and cleaned up, then came back out with my towel wrapped around my waist, since I didn’t seem to have any choice. It’s not as though I was going to physically fight her for my clothes.

“You need to go back in there and shave your legs,” she told me. “Don’t bother with anything else; I’ve seen your armpits and your smooth face.” She handed me a pink women’s razor and shaving cream, and I went back into the bathroom. As I shaved it started to penetrate that she must have been planning this. Why else would she have brought along a razor and the can?

I didn’t have a whole lot of leg hair, but I was careful not to cut myself. Checking my face there was nothing to shave there, as she had snidely pointed out. I dried off and went back into the room.

She had her clothes laid out on the bed, and supervised while I put them on. She had to help with the bra, and when she brought out these two triangular jelly-like globs of something to put in the cups I knew this had to be pre-planned. I just couldn’t figure out why.

She put the dress over my head and zipped it up. It was a knee-length peasant dress; at least it was on her. On me, it was a bit longer. It had a square neckline and puffy three-quarter sleeves. It fit me fairly well, and I felt ridiculous in it. She went to work on my face with her makeup, and after she dried my hair she combed it into what she called a pixie cut. Lastly, she painted my nails a deep red. This all took quite a while, and I sat there and wondered just what kind of person would force someone to do this. How had I misjudged her this badly? And what else about her didn’t I know?

She put some bangles on my left wrist and a cheap necklace on my neck.

“There! Pretty as a picture!” she said, turning me towards the mirror.

I didn’t agree with her assessment, though I do admit I looked kind of female. That didn’t make me one bit more interested in exposing myself to the public though.

“How long have you been planning this?” I asked. “And why?”

“Actually, it was a spur-of-the-moment thing. When I woke up I decided it would be fun, so I went across the plaza to the Wallymart and bought a few things. Ever since I met you I thought you were too small and pretty to be a guy. Put the heels on.”

Too pretty to be a guy, eh? I don’t think so! As far as I was concerned I was just… a normal-looking guy. Looking down now, I was very surprised to see she fit into my shoes. And, by the way, she sure didn’t look like The Man, or even a man! Even in my clothes—a button-down shirt and khakis—she somehow managed to look like a stylish woman. And for “a man” she sure had done her makeup nicely! There was some kind of hidden agenda here. Anyhow, I got the four-inch heels on, stood up, almost fell down, and for the first time found myself looking straight into her eyes.

She handed me her purse. “Well, come on. Let’s go have breakfast.”

“I can’t go out looking like this!”

“Sure you can! You look wonderful. You’re very pretty.”

“I don’t feel wonderful; I feel ridiculous. And I feel like you’re trying to make a fool of me.” I sat back down on the bed.

Her tone changed. “Oh, is that so? Well, your choices are, either come on out with me, or you can walk home.”

I couldn’t believe this! It was blackmail. Did I even want to be with someone so mean-spirited, and so ‘my way or the highway’? I had no desire to go outside and pretend to be a woman, although it looked like either way I would end up outside. But I did not care for her attitude, not one bit.

I just sat there, looking at her with my best sorrowful, accusing expression.

“Fine. I’ll be over there in that IHOP*. You can join me when you get up the nerve. Oh, and keep your legs together, Missy!”

And with that final jab at my male ego, she walked out.

What a crazy situation! If there was any consolation at all, it was knowing now just what kind of person she was. Is the only reason she first spoke to me because she was planning this? Was it just a game of ‘Let’s humiliate the guy’? Or a bet with someone? I had been too timid to approach her, and she had come over to me at a café and kind of swept me off my feet. That was only about three weeks ago. Man! What a stupid sucker I am.

I stayed there thinking and stewing for a couple hours, playing with the bangles on my wrist until almost eleven o’clock, which was checkout time. I do have to admit I had heard that “too pretty to be a guy” when I was growing up, but I always thought they were just teasing me. By the time I hit my twenties, I was sure I had grown out of it. And yes, I was kind of puny, but what did that have to do with anything? The Three Stooges were short, but that didn’t make them “too pretty!”

By ten thirty I had looked out the window and seen that her car was no longer in the lot. She had gone ahead and abandoned me. I wasn’t sure exactly how I felt about that. Now at least I wouldn’t have to deal with this unattractive side of her personality, but I was stranded with no way to get home.

Checking my wallet, which she had put inside the purse, I saw I had eleven dollars. Not enough to buy men’s clothes, if there even was a store in the plaza that carried them. Not enough for a taxi or an Uber. There wasn’t one person I could think of who I could call to come and get me. And would I want whoever that was to see me like this? NO.

It was now quarter to eleven. Taking a deep breath I put on the lightweight, white cotton jacket and the floppy straw sunhat, picked up the purse and walked out the door.

-o0o-

So here I was now, stumbling along the highway, in a dress and high heels. Taking off the heels was such a temptation, but I really didn’t fancy walking on sharp-looking gravel. I was thankful that the weather was very pleasant today. The gentle breeze was nice, but I discovered it meant I had to keep a hand on the hat to stop it from flying off.

Before too long a car slowed down and the passenger window opened.

“Hey babe, can I give you a lift?”

Without looking at him I said, “No, thank you.”

“You sure? It’s a long way to, well, anywhere.”

“Thank you, but no.”

“Suit yourself.” And he took off.

This happened three more times as I struggled along. All three were men. Two of them were more, ah, insistent than the others. Both of them kept pacing me as I walked, ignoring them to my utmost, until they finally got the message. There was no good I could imagine happening from taking a ride with a guy. Although a guy myself, I had no idea how to deal with male advances from the woman’s side of the issue. Saying, “Beat it,” in my lowest voice probably wouldn’t be the wisest option.

As I stumbled along I started to imagine a situation where I was walking along here just like this, but I was, well, a lot stronger. The guy slows down and asks me if I want a ride. I accept and get in. Then he starts coming on to me, putting his hand on my leg, so I grab his wrist and start to crush the bones! Ha! That would show him! Or maybe some martial arts twisting of his thumb or something. Oh, but then he’d probably ask me—politely?—to get out of his car, so I’d be walking again. Oh well. So much for that daydream.

-o0o-

In maybe two hours I’d probably gone a scant three, maybe four miles, still with nothing in sight other than the highway, grass and trees when another car slowed down. Sighing to myself, I waited for the inevitable.

“Hey, Miss. Can I give you a lift?”

This time it was a woman. I stopped, bent over and looked into her car. Dressed very casually, she looked quite pleasant, and just a few years older than I.

“Thank you! I’d love a ride,” I said, in a soft voice I hoped would disguise who I was. I opened the door and got in the way a woman wearing a dress would get in, sitting down first and pivoting over. I had observed women over the years, after all. I took off the hat.

She gave me a close look and asked, “Where are you headed?”

“Back to the city.”

“Well, I can’t take you that far, but at least to the next business district.”

She looked at me again.

“Listen, how would you like to have lunch with me? You can tell me how a nicely dressed girl like you ended up walking alone on the highway,” she said with a smile.

When she mentioned lunch my stomach ordered me to say yes, reminding me I hadn’t eaten anything today.

“That would be great, and I’ll try and tell you what happened,” I said, wondering just what in the world I would say.

We didn’t speak further. Maybe seven miles further on there was a business district, and she pulled off into the parking lot of a good-sized family restaurant. We went in and were quickly seated.

Putting out her hand, she said, “I’m Jean Bowden.”

I shook it and thought there was no reason not to use my unisex name. “Robin Gray.”

We ordered lunch (I got the cheapest thing on the menu—a tiny salad with a hard-boiled egg in it) and she looked at me expectantly.

“Well, Robin, how did a pretty girl like you get abandoned on the highway?”

Is this how women normally spoke to each other? Just telling perfect strangers they were good-looking? I knew I looked sort of like a woman, but pretty? Nuh-uh. Blushing, I quickly thought about my options here. And, what the heck, what did I have to lose at this point if I told her the truth?

“It’s like this, Jean. You may or may not have noticed that I’m male—”

“I did wonder,” she said.

“—ah, okay, but… my girlfriend… or maybe I should say ex-girlfriend now…and I went for a drive yesterday. She decided we’d stay at a motel overnight since it was getting late. When I woke up this morning she was wearing my clothes! She said she’d decided to ‘be the Man’ today! My only option was to wear her clothes, but I didn’t want to leave the room. So she pretty much deserted me there. I don’t have much money, so I just started walking.”

“She sounds like one crazy bitch,” she remarked. “So you get to ‘take a walk on the wild side’ through no wish of your own.”

I nodded. “I don’t know anyone I could call to come get me, and I wouldn’t want them to see me dressed up like this anyway.”

“Well I think you look very good,” she said.

“Um, thank you?”

“It is a compliment. You look better than some women I know. Have you ever dressed up before?”

I blushed again. Even as a man I didn’t know how to handle personal compliments, which were rare in any case.

“Um, no, never,” I answered her.

Our food was delivered, and we got down to the business of eating, each thinking his or her thoughts, I’m sure. I kept glancing surreptitiously at her. I felt she had a very nice face. Light brown hair in a kind of messy bob. She looked sturdy but feminine.

“Robin, I don’t know what your plans are, but I’d like to help you. Here’s what I can do: I can’t take you back to the city until the end of the week, but I have a good feeling about you. So I’m willing to let you stay at my place until then. Maybe not the best solution, but it’s what I can offer. After all, you are a maiden in distress!”

I ignored that last bit. “Well, that’s very generous of you. I’m not sure what I should do. I didn’t leave the motel with an actual plan, but I had to be out by eleven, so I was. I didn’t think I would be able to walk all the way home—well, especially in these heels!—but I had to go somewhere. Umm, why don’t I shut up and stop babbling.”

Jean giggled about the heels, and maybe about my last comment.

“Do you have a job, Robin?”

“Yes, but it doesn’t pay much. If I don’t come in until Friday, or, that would probably be Monday, I’ll probably be fired, but it’s not as if that would be a terrible loss. I’m sure I could find another low-paying job!”

“Can’t you call them and explain?”

“It’s not that kind of place. You don’t show up, you lose.”

“Okay, so you’ll be staying at my place?”

“Yeah, I guess I will, if you’re sure. Thank you so much!”

We were done with our meal. Reminding me to grab the purse Jean took me into the Ladies room and coached me on how to touch up my lipstick, which I found in the purse. She also saw I was still very nervous and self-conscious—especially in there!—and she gave me a nice little hug.

“You’re doing fine, Robin.”

“Thank you. I feel like a complete idiot.”

“Not at all. You seem to be a natural. It was only the way you moved out on the highway that told me you might not be female.”

-o0o-

We paid and left, and she took me to her home, a small, one-story, single-family house in a residential area not terribly far from the restaurant. She pointed out the kitchen and the bathroom.

“Listen, I’m sorry to leave you alone, but I have some work I need to take care of at the office. Make yourself at home for a few hours, and when I get back we’ll have dinner, okay?”

“Uh, sure. I can’t thank you enough for your kindness.”

She smiled and left. I stood there, having no idea at all what to do with myself. Standing there reminded me of one thing I could do: take off those heels!

It was hard to believe a perfect stranger would just let me stay in her home, alone. I wandered around the place, just to see it, and to see if there was anything to do. There was one good-sized bedroom and a small one she apparently used as an office. It was pretty basic, but it felt comfortable and homey and with a woman’s touch. In the kitchen, I saw she’d left her breakfast dishes, so I washed them. Then I decided I might as well tidy up a little, as a way of saying thank you. It wasn’t hard to find her vacuum, and I vacuumed the carpet.

If I thought that doing these mundane tasks would help me forget about the surreal life I was living today, I was wrong. As I moved the skirt swirled around my legs in a way I found myself enjoying. Every time I reached for something I saw the little three-quarter sleeves with their little ruffles at the end, not to mention the red nails, and thought ‘Is that my arm?’ It was all so odd. As I vacuumed I started to daydream that I was taking care of the house, as if I was Jean’s wife, looking forward to her coming home to me— Hey! Wait a minute!! What was wrong with me?! I shook my head to clear that daydream out of it.

Once I was done cleaning I went into the living room to sit down. There was a little pile of knitting to one side. I didn’t know anyone knit anymore. I found a news magazine to read, watched a little TV, thought once more about this peculiar situation, and, not knowing what else to do, I curled up on the couch and was quickly asleep.

-o0o-

Next thing I knew Jean was gently shaking me.

“Robin, oh Robin.”

I blinked, saw her and remembered where I was. It was dark outside.

“Oh, hi,” I said and stretched. “Did you get done what you needed to get done?”

“Yes, thanks for asking. Sorry it took me so long. Oh, and it was very sweet of you to clean up. I should hire you as my housekeeper.”

“It was the least I could do,” I said and smiled at her.

“Want to help me make dinner?”

“Um, sure.”

I stood up, and without the heels on was surprised to find that Jean was at least four inches taller. Changing height in one day wasn’t something I was used to.

-o0o-

We had a pleasant time preparing a simple meal together, and it felt nicely intimate eating it there with her. I decided I really liked her and thought we were getting along very well. Being with her was helping Marian recede towards the back of my mind.

“So Robin, tell me a little about yourself.”

“There’s really not that much to tell. I grew up in the city, and when I finished high school I started working. My dad told my sister and me that we should be prepared to be on our own when we turned eighteen. He had been on his own at that age, and he thought it was character-building, so everyone should do the same. But really, I don’t think he liked either of us. That was just his way of getting rid of us. Jill—that’s my sister—got married and moved far away to Washington State, while I went from one crappy job to the next. I think she got married only to get away from him.”

“What did your mother say?”

“She died when I was eleven. So Jill and I were close, or at least I thought so, but I just about never hear from her.”

“That’s sad. So how long have you been on your own?”

“Uh, let’s see… I’m twenty-two, so four years now.”

“Your dad sounds kind of tough.”

“Oh, you better believe it! Jill and I did all the housework and cooking, and we’d be in big trouble if it wasn’t done to his satisfaction. And then, when Jill left, I had to do all of it alone. I haven’t been back to that house since I turned eighteen. How in the world does he keep it clean now?”

“And how about your love life, Robin? One girl after another?”

“I know you’re joking, Jean. No, Marian was the first woman to show any interest in me, and now I feel like the only reason she spoke to me was so she could get me into a dress.”

“You could be right, but I’m glad she did. Otherwise, we would never have met, and I am already very glad I met you. You’re a breath of fresh air.”

Smiling at her, I blushed once more. I needed to change the subject.

“What about you, Jean? What’s your story?”

“Well, I grew up in the outer suburbs of the city, the oldest of a family of five girls, went to a good private school and a decent college. My friend, Carole, and I started a business about eight years ago, and it’s doing pretty well if I do say so.”

“Did you ever get married?”

“No, but I came close a few years ago, but as we got serious about each other I realized there was no real spark between us. When we discussed it he admitted he felt the same way, so we broke it off before we made a big mistake.”

“I guess I can understand that. Do you mind if I ask how old you are?”

She smiled. “No, I don’t mind. I’m ten years older than you.”

“Gee, I had no idea. I thought you were maybe twenty-seven tops.”

“That’s sweet of you, Robin. What do you say we watch a little TV before bedtime?”

“Okay, sure.”

-o0o-

When I came to sit down next to her, she commented on my appearance.

“You know, you really do look nice in that dress. Very cute.”

I grabbed the hem and fanned it out. “What? This old thing?” I said, and we both burst out laughing. Somehow I found I didn’t mind when she complimented me, the way I had when Marian did, and I gave her a nice smile. Though that line wasn’t so awfully hilarious, we both found ourselves snickering at it on and off. That created a nice shared sense of intimacy.

I don’t know why I was so tired, having already had a nap, but I found myself falling asleep, with my head gradually leaning on her shoulder.

-o0o-

“Come on, sleepy head. I think it’s time for bed.”

“Oh, sorry. I didn’t mean to fall asleep on you. I’ll just stay here on the sofa.”

She gave me an amused look.

“That’s silly. I have a king-sized bed. I’m sure we could both sleep there without getting in each other’s way,” she said, pulling me to my feet.

She used the bathroom first and then sent me in there with a cotton nightgown and instructions on how to clean the makeup off. I had to ask her to come in and unzip me, as well as unhook the bra. It was embarrassing, but not too embarrassing, since, for some reason, I felt very comfortable with her. She suggested I wash out the panties, and briefly explained the process. Although I was familiar with doing laundry, hand washing wasn’t something I had ever learned.

When I finished I came into the room in the nightgown and got into bed as far from her as I could, so as not to invade her space or make her uncomfortable. She smiled and we said goodnight to each other.

Was I really so non-threatening? Wouldn’t most women make the guy sleep on the sofa?

Did she even see me as a guy?

-o0o-

When the alarm went off in the morning I found myself closer to the middle of the bed, with Jean spooning me, her arm around my stomach. It felt wonderful, but I panicked.

“I’m so sorry, Jean. I didn’t mean to—”

“I’m not,” she interrupted. “I slept really well,” she said in a very cheery way, striking me as a real morning person. That was interesting…she didn’t seem bothered at all about sleeping with me and touching me, a total stranger!

She hopped out of bed and took care of her morning routines, while I waited for the bathroom.

When I was finished she said, “Listen, unless you want to wear your dress again, all I think I can offer you is a skirt and blouse. My pants would all be too long for you.”

Since all of it was women’s clothing I supposed it didn’t really matter which, and I assumed Marian’s dress might need a wash by now. So I opted for the skirt and a long-sleeved blouse, not bothering with the bra. I thought about asking to borrow some money from Jean to buy a shirt and pants, but I felt I didn’t knew her well enough to do that. And I couldn’t even imagine when I’d be able to pay her back.

“What do you think you’ll do today?” she asked.

“I really have no idea. I still can’t think of a way to get home.”

“What if you were to come to the office with me? We might be able to find you something to do there, and it would have to be more interesting than just hanging around here and watching TV.”

Being out in public was certainly not my first choice, but admittedly I was much more used to looking like this now than I was twenty-four hours ago. And really, no one but Jean had figured out what I was. Not those drivers, no one at the restaurant…

“You know, you’re right. Maybe I could do something useful there.”

She asked me to go put the bra on with the fillers, explaining the easiest way to do it. Then she helped me with my hair and makeup. When she was done she smiled.

“There, every inch the professional girl.”

No guy really understands how to respond to compliments like that, so I just smiled.

“Pity our feet aren’t the same size because I’ll bet you’d like to wear something other than those heels!”

“You got that right!”

-o0o-

We had a quick breakfast and then she drove us to her place of business, back a few miles past where the motel was. Her office was some kind of accounting place. Along the way she tried to give me some pointers about female behavior and walking and gestures, but I didn’t think I would remember most of it. We parked at the side of a low, freestanding brick building and went around the front to enter. The place was basically a big room. There were about ten employees, all working at computer stations in cubicles.

Jean took me to her partner, Carole, in a small office off the back of the main room. She struck me as a take-charge kind of woman, in a casual business suit.

“Morning, Carole, this is Robin Gray. I met her yesterday and she’s had some hard luck, so I’m letting her stay with me for a few days. I thought rather than leave her at home with nothing to do, she could hang out here, maybe help out, if that’s no problem.”

Carole looked me over carefully, making me feel self-conscious.

“Of course, Jean. Nice to meet you, Robin,” she said, shaking my hand. “I’m not sure what we have for you here, but would you be willing to do things like make coffee and be a kind of Girl Friday?”

“I’m happy to help out,” I said. “I’ve worked as a barista before,” I added.

Carole laughed. “That’s a little more involved than what I had in mind, but good to know! If we get an espresso machine in the next couple of days, you can be the coffee girl!”

I blushed yet again. Everything and everyone reminded me of my changed status. All those female pronouns really drove home the point…to me, anyway.

“Jean, why don’t you introduce her to our staff. Robin, after that why not wander around a bit and see what we do here. Maybe something will pop up that you can help with.”

“Thank you, Carole. I will.”

One by one Jean introduced me to the mostly female staff and told them I’d be willing to bring them coffee and help out. They all gave me smiles. The couple of men there eyed me in an appraising way I was not used to experiencing. It made me uncomfortable.

After Jean went to work, in her own little office, I wandered around the place. During the morning I got coffee for several of them, fixed a jam in the copier, and actually was able to help one of the women with a little problem in her spreadsheet program. A woman named Joyce showed me where the office supplies were stored, and a couple times I was asked to go there and get something from the stash. I tried to be as polite as possible, and they were all friendly in return, and I found that by the end of the day, I had done something for every woman in the place.

-o0o-

.
Jean
Let me just start by saying I had never been attracted to a woman before. But when I saw a nicely dressed but awkward young lady incongruously picking her way along the side of the highway, trying to hold on to her sun hat, I just knew I had to stop for her. There was something so innocent yet sexy about that picture. To my eye, she moved a little bit like a guy, but I could see the terrain was pretty rough for heels. However, when she got in and took off her hat and I got a good look at her face all I could see was a pretty young woman.

I had a impulse to invite her to lunch, and there she told me her story. I felt bad for her that her “friend” had treated her so poorly. Sounded like that woman had a real agenda. I couldn’t help but notice that even as Robin talked and ate she came across as female, and I could certainly see why that woman had been tempted to try this. Not that I agreed with forcing a guy to do something such as this… but it really made me wonder just how effeminate she—I mean he—was as a male.

When she told me she was a boy—well, a man, I suppose—I felt very intrigued. There was something so feminine about her that just sparked a low flame of arousal in me. How could a man come across like this? Especially one who claimed he had never done it before?

I can’t even talk about her as being a man, and yet, there was something about that little fact that made this whole situation sensually stimulating. It was fascinating.

When we were finished with our meal I took her into the ladies room to touch up her lipstick. The poor thing was so nervous I gave her a little hug and told her she was doing well. I wonder if she enjoyed it as much as I did. My impression was that she was very unused to compliments.

She seemed so helpless, and I could see that for her it really was a difficult situation. I couldn’t help liking her, so I decided to do what I could for her. I took her to my home and dropped her off, then went back to the office to finish up a few important bits of time-sensitive paperwork. (I’m co-owner of an accounting firm, and make a modest living.) This also seemed like a good test of my intuition. If she had a bad character she’d steal something and leave, but I didn’t think that was going to happen.

-o0o-

When I got home and walked in, much later than planned, it was dark inside, which seemed odd. When I turned on the kitchen light I could instantly tell that she had cleaned the place up. That was very kind of her, and, not to be sexist, but it didn’t seem like something the average man would have done. But where was she? Had she gone after all? When I went into the living room there she was, asleep on the couch. She looked so sweet, and so young, curled up there in her peasant dress.

I gently woke her, and she was polite enough to ask about my work. So few people nowadays seem to want to talk about anything but themselves, so that impressed me. And without the heels, when she stood up she only came up to my chin. Could this really be a man?

She helped me fix dinner, which was pleasant, and seemed to know her way around a kitchen. We ate and then chatted about our histories. It didn’t sound as though she had grown up very happily. The tragedy of her mother dying so early… And what kind of father kicks his kids out at eighteen, just ‘because?’

After that, we sat down together to watch TV. Soon she fell asleep against my shoulder. She was pushing buttons I didn’t even know I had. So darned cute!

When I woke her to tell her it was bedtime, she actually offered to sleep on the couch! I almost laughed, as I really couldn’t see someone like her trying to take advantage of me. Just looking at her I didn’t even believe she could be stronger than I am anyway, so I said we would share my big bed.

When I sent her into the bathroom with a nightie I told her how to remove her makeup. In two minutes she opened the door and asked me to help her with the dress and bra, which I was happy to do. I did notice she wasn’t hairy like a man and certainly did not have the broadest shoulders

When she came back out, in the nightie, I could still easily see the girl, even without the makeup and breasts. I admit I was attracted, and it was odd feeling that way about someone who seemed to be a woman. However, I couldn’t deny the way I felt.

It was amusing to see how she got into the bed at the very edge of her side. During the night, as I looked at her over there at the edge of the bed, I developed a real desire to have her close to me, and I managed to slide her over some and spoon her, all without waking her up. The satin sheets made that fairly easy, or else she was a heavy sleeper!

As I said earlier, I had never been attracted to a woman, and yet this small, cute boy was really nothing like a man. I enjoyed being the older and bigger partner for a change when I held her while we were in bed. It was quite a new sensation. I wanted to protect her. And she sure didn’t feel like a man! She smelled like flowers, which is not the usual scent of a man. I slept well!

-o0o-

In the morning I suggested Robin come to the office with me, sure Carole and I could find her something to do. She had no way to get back to the city, and, she said, very little money. Coming in would be better than just hanging out at my house all day. I found a nice blouse and skirt for her; not much else of mine would have fit her, and even these were on the large size. I usually wore pantsuits to the office.

After I did her makeup she really looked good. I knew she was nervous about meeting other people with me, but I assured her she looked very nice and she smiled, and it was a nice smile.

-o0o-

Once she met Carole, my business partner, I introduced her to all the other employees. Not one seemed to have any idea she wasn’t a woman, although I was beginning to think that maybe she really was a woman… inside. The idea of a man/woman mix was rather enchanting.

It wasn’t long before she proved herself useful at the office, and I started scheming how to create a position for her. She had as much as said that her job back home wouldn’t be waiting for her, so why not stay here and work for me? From what I observed, the women all took a real shine to her. Dennis and Craig mostly seemed to ignore her, although I saw Craig’s eyes following her at least once. I have no idea what she was like as a man, but something about her just made you want to be nice to her.

There was something else, too. I could have afforded to buy her men’s clothes, but what would that mean if she showed up at the office as a man the next day? I didn’t want to subject her to possible nasty comments or attitudes. No, better for her to keep her in her women’s things. Better for me, too!

-o0o-

During the week Robin fitted in quite well at the office. Everyone seemed to appreciate the little things she did, and I was pleased. Every so often I had meetings at different locations during the day, and on Tuesday while I was out I went and bought her a dress in her size, another skirt and two blouses. I wanted her to wear things that actually fit her. These were a bit more feminine than the clothes I had been loaning her, but by Wednesday I didn’t think she would have any objections. She would wear whatever I gave her each morning with no complaints. I also picked up a pair of sneakers to give her at least one alternative to the heels, in which she was now a reluctant expert.

On Tuesday and Thursday evening, when we had finished work early enough, I took her to the park near my home and we went for a walk for exercise. I found it very pleasant to share the walk with someone, especially Robin, whose company I was enjoying more and more. She was no intellectual, but she was funny and self-deprecating, and she was filling a hole in my life I had almost forgotten was there.

By Wednesday some of the girls liked her enough to ask her to come with them to lunch, and I’m sure they wanted to grill her. She looked at me, scared, but then said, “I really don’t have the money, sorry.”

“I’ll treat you, Robin,” I said and went with them.

-o0o-

At the restaurant, Rita, one of our accountants, started off the questioning.

“So Robin, tell us your story. Where did you come from?”

“Um, well, I was walking along the highway on Sunday and Jean picked me up. I don’t have the money to get back to the city, so I’m just staying here for a few days.”

“Walking along the highway?” asked Joyce. “Wait. Back up. Why in the world were you doing that?”

“My, um, boyfriend, abandoned me at a motel.”

“What a louse! He didn’t hit you, did he?”

“No, no, nothing like that. We just had a…a disagreement. Then he said he was going to breakfast, and he expected me to join him as if everything was fine and decided. And if I didn’t come with him I could walk home. I just thought, well, if he’s going to act like that, I don’t need to be with him!”

“Good for you, girl!”

I thought Robin was doing really well with this, although I could tell she wasn’t enjoying it.

“Where do you work in the city?” asked Martha.

“Oh, I was just a clerk at an aquarium store. You know, equipment, little fish, stuff like that.”

“Was? Aren’t they holding your job for you until you can get back?”

“Well, um, no, you’re only allowed one unexplained absence, so I’ll be looking for another job, probably, when I get back.”

“Oh, forget about that, Robin. You should stay here, with us!” said Joyce.

“That’s a great idea, Joyce! Jean, you and Carole can come up with something for her, can’t you?”

Robin turned to me with panic in her eyes.

“I’ll have to discuss it with Carole.”

“But, but…”

“No buts, Robin,” said Rita. “We all like you. You should stay here.”

“Absolutely,” said Martha.

I looked at Robin and her eyes were actually brimming with tears! She must be lonelier than I thought. I handed her a tissue, leaned over and whispered, “Just dab at the corners of your eyes.”

“Thank you all. I’m not used to anyone sticking up for me.”

-o0o-

She continued to prove helpful at work, and I discussed with Carole creating a job for her. We finally came up with a kind of Receptionist/Girl Friday position. It wouldn’t pay much, but if my plans worked out that wouldn’t matter.

“When do you want to offer her the job?” Carole asked.

“Let’s see what happens when I take her back to the city on Saturday. My feeling is that she has enjoyed being here. Everyone seems to like her, and I get the impression that she was just tolerated at her other job, which she says will no longer be hers by now.”

“Sounds fine to me, Jean. You can handle it.”

.
Robin
I was able to settle down and enjoy what I was doing at Jean’s office. Each morning she would give me a skirt and blouse to wear, although on Wednesday, for a change, she handed me a dress, and it actually fit me. When I asked, she said she had bought it for me and also gave me a pair of sneakers, for which I was very thankful! For a minute I wondered why she didn’t get me men’s clothes, but by now everyone at the office thought I was female, and coming in as a guy would have been, just… well, bad.

The people at the office were very kind to me, and I kept finding little things to do which kept me more or less busy. It was kind of cool to make up my own job. The two guys mostly ignored me, and I was content with that. I still had no idea how to interact with men as a woman. The one or two times we passed each other I felt very small and very vulnerable. I didn’t recall feeling like that as my normal, male self.

At Jean’s house we got along so well. Twice we went to the park to walk, for exercise, and I really enjoyed that. In my real life, my main exercise was just walking back and forth to work. Walking with someone—someone you liked—was a big improvement on that!

And it was kind of weird, but just about every morning I would wake up and find that Jean was holding me. Don’t get me wrong – I really loved the feeling, but couldn’t figure out how we got so close to each other while asleep.

-o0o-

When we left work at the end of the day on Friday, Carole gave me an envelope with two hundred dollars in it!

“What’s this for, Carole?”

“You’ve been here all week, Robin, helping out. I think you deserve some compensation.”

“I don’t know what to say. Thank you very much, but I was just helping out.”

She smiled and said, “I hope you come back to visit us, Robin. It’s been very nice to have you here.”

I smiled back. Everyone here was so nice to me. But I did have a sort of life back in the city, and it was hard to imagine wearing a dress just to visit. Soon enough, back in the real world, I would have to try and find money for rent. Ugh.

-o0o-

Saturday morning Jean and I were up and had breakfast, and pretty soon we were speeding along toward the city. I was back in Marian’s dress, now clean, and it felt pretty normal by now, having worn skirts all week. The same for the bra. Jean had taught me a little bit about makeup, and I was able to do a halfway decent job of it. During the week I discovered I enjoyed wearing skirts, especially in this nice weather. Still, I did look forward to wearing my own clothes again and going back to being a man. As much as Jean thought everyone saw me as a woman, I didn’t know anything about being female. I do have to admit, though, that I liked how people were treating me; they were much kinder than I was used to. And by now I kind of liked looking nice, and the women at the office would compliment me. I’d never really given a lot of thought to my appearance before.

Jean spoke, bringing my attention back to the present.

“So do you have a plan for what to do if you’ve lost your job?”

“Well, there’s this guy at a tool and die factory who might know of a job there.”

“Robin, I don’t want to discourage you, but you don’t look strong enough to work at a factory. You’re not trained in tool and die-making, are you?”

“No, I’m not. But maybe they’ll have some kind of office position?”

“You never can tell,” she said, looking thoughtful.

We reached the outskirts of the city, and not long after, my neighborhood. When we got to my street and came close to my place my jaw fell open. My small apartment building was a charred ruin. Either there had been a fire or a meteor had hit it. There was yellow “Keep Out” tape all around it. It was so shocking I could hardly think. All my stuff! I mean, not that I had a lot of stuff, or even anything very good, but every single thing I owned was gone!

“Oh my,” said Jean. “This kind of changes things. Did you have renter’s insurance?”

Being in a daze I didn’t hear her and she had to repeat the question.

“Uh, no. My job didn’t pay that well. I mean, I guess I could have afforded it, but…”

“Would you like to see if the building owner was insured, so maybe you could collect some sort of payment? Your security deposit, if nothing else.”

“Well, I do know where the office is that owns the building, but I don’t think it’s a good idea to go in there asking about it as a woman.”

“They know Robin is a man?”

“Oh, I don’t know, Jean,” I said, despondent. “I have no idea what to do now. I literally have nothing.” I leaned over and put my head in my hands.

She put a comforting hand on my back. “That’s not exactly true… you have me. Listen, Robin, don’t worry, I know what to do. We’re going back home, and you’ll stay with me until you decide what to do with yourself. I’ve loved having you as a guest, and I’m pretty sure Carole would be happy to hire you for that helper position. You already know everyone there likes you.”

“Hmm.”

She patted my knee. “You think about it on the way back. It’ll all work out.”

And I did.

My life seemed to be spiraling out of control. A mere week ago all was well. Now I’m kind of living as a woman, and living with a woman I really like but barely know. I have almost no money. Everything I own is gone. And… I just realized that means I don’t own one scrap of men’s clothing. No clothes except the dress I was wearing. No one at the office seemed to think I was a man masquerading as a woman, which was just beyond my comprehension. Why couldn’t they see how obvious it was I was a man?

Well, I should try and think of the positive aspects…ummm…Well, Jean was really nice to me. She was feeding me, giving me a place to stay, and lending me clothes. She seemed totally non-judgmental about me being a man dressed like a woman. And to be honest with myself, I wasn’t actually having a lot of trouble acting like a woman, whatever that actually meant. The things I was doing weren’t much different than they would have been if I were doing them as a man. Yeah, you had to keep your legs closed and not bend over and expose anything… Oh, and I had to try and sound more like a woman. But really, I didn’t think I was acting much different than my usual self.

What else? Oh, the ladies I worked with all treated me well. They were all older than I was, and they always seemed appreciative when I did something for them. I guess I felt like they treated me as a little sister? I felt that the two guys took me more for granted.

They were all really nice yesterday when we all thought I’d go back to my life in the city and that would be that. It wasn’t exactly a party, but someone did bring in a box of cupcakes. I’ve never worked with people before who would go to that kind of trouble for me.

Oh my god! I just realized something else: if I had been home, I might have died in the fire! I can’t say I knew my neighbors, but I hope none of them died because of this.

Anyway, the real question was: did I want to continue for the foreseeable future as a woman? And if I didn’t, what were my options… if any?

-o0o-

Jean left me alone to think while we were driving. I hardly noticed when she turned off into a shopping plaza, only snapping back to reality when the car stopped.

“Where are we?”

“We’re going to get you some sensible shoes.”

“But Jean, I shouldn’t spend money on stuff like that!”

She smiled. “I’ll pay for them. You’ve helped out so much at work that I owe you at least that!”

We went into a big box shoe store and she helped me pick out some nice shoes with a two-inch block heel I could more easily deal with. They were much more comfortable than the stilettos, and my calves and toes said, ‘Ahhhh. Thanks.’

She paid for them and we walked out, with me wearing them. I stopped and turned to her and hugged her, and gave her a kiss on the cheek.

“Thank you very much!”

“My pleasure, honey.”
.

Jean
It was quite a shock when we found that Robin’s building had burned down, and she was devastated. The neighborhood was kind of seedy, and there were other buildings in bad shape. When I suggested trying to get her security deposit back she was afraid they’d have an issue with her showing up as a woman, which I thought was silly, although I didn’t say so.

She was depressed and had no idea what to do, so I brought her back home with me. After a somber lunch, we sat on the couch together and I put my arm around her. She leaned into me and put her head on my shoulder. I was very pleased that she felt comfortable enough to do that, though I’m sure it was mostly because in her distress she was seeking comfort.

“Jean, what am I gonna do? I’ve got no job, no place to live. No men’s clothes… I don’t see how I’ll ever be able to afford to replace anything.”

“You want to know what I really think, honey?”

“Yes.”

“I think you should stay right here with me and go to work with me. I’ve grown very fond of you over the last week, and we get along great together. Plus, you seem happy helping out at work.”

She looked up at me.

“But then I’d have to stay as a woman.”

“Is that so terrible? Is your life so different now? Are you unhappy like this?”

She looked down. “Well, no, it’s not all that different and I have been happy staying with you, but it seems like a big change.”

“If you say it’s not all that different, then maybe the main change is just the clothes. They don’t change who you are, Robin. From what I have observed over the last six days, you very naturally act like a woman. Almost nothing about you suggests anything different.”

“You’re serious? And here I’ve been so confused why no one has guessed about me. When I look in the mirror I still see a guy.”

I turned her face toward me. “And what I see when I look at you is a pretty young woman… whom I like a lot.”

She stared at me, and I leaned over and kissed her gently. She looked at me in a kind of goofy, dazed way, and I tightened my arm around her.

“I would love for you to stay here and be my girl.”

“But, but Jean, I’m not a girl.”

“But honey, you really are; deep inside I can tell there’s a girl in there. A very delightful girl who grows on me every day.”

There was a silence as she digested that.

“Do you really mean that?”

I kissed her again, deeply. “Yes, I really do. I know we haven’t even known each other a whole week, but I already adore you.”

She put her head back down and snuggled into me. God! This girl!

“I feel the same way about you, Jean. You have been so good to me, and I feel very comfortable with you. If you hadn’t picked me up that day…I don’t know what would have become of me.”

.
Marian
I admit that when I first met Robin I thought he was so feminine that I’d eventually have to find out what he looked like dressed up. So I did come on to him, and it was easy to start a relationship, which might have been his first. Yeah, he was a nice guy, but naïve, and totally clueless about how he comes across. He always let me make all the decisions. I feel I’m a very feminine person, but I have to just say I’m more of a man than he is. Anyhow, when the opportunity presented itself, on our long drive, to swap clothes, I jumped at the chance.

We had stopped at a motel for the night. Waking up early the next day I got into his clothes and walked over to the Wallymart across the plaza from the motel. I got some toiletries, a ladies razor, shaving cream, some chicken fillets to fill his bra, a few bangles and a necklace. This was going to be a blast, and I felt sure he would enjoy it too.

When he woke up he balked at putting my clothes on, but I didn’t leave him any choice, so he had to wear them or go naked. He sat still while I did his hair and makeup, and I was not disappointed with the end result. But then he refused to leave the room with me to go eat, which made me angry. I gave him an ultimatum, and when he wouldn’t get up and come with me, I left him in the room. I went and had breakfast, and when he still hadn’t come out I got in my car and started home.

I’d driven about forty-five minutes when my conscience forced me to turn back. I’m not heartless. I really thought the whole swap thing would be a lot of fun. Anyhow, I got back to the motel at 11:45, and found the room empty and someone cleaning it. I expected I’d find him hanging around outside there, or in the motel office, but there was no trace. Having looked in his wallet earlier I knew he didn’t have enough money to get home, so where could he be? I looked around the area for almost a half hour, and then threw my hands up and drove home.

Back in the city, on the way home, I stopped by his grungy little apartment, but there was no answer when I buzzed, and no messages on my phone. Every day I kept expecting to get an angry phone call, but there was nothing. It was as if he’d just vanished. I half wondered if he had hitched a ride with some maniac who found out he was a man and did something awful to him. I wouldn’t wish that on anybody.

Four days after I left him, I read that his apartment building had burned down! There were two unidentified bodies in the rubble, and I really hoped he wasn’t one of them. But I never did hear from him again, so maybe he had died after all. I vowed to be more sensitive to how I treated people in the future.

The End.

*International House of Pancakes (and also known to a select few as I Hate Other People)

Author’s Note: For those who wondered why, when Marian was driving back, she didn’t see Robin walking on the highway, it’s because she wasn’t expecting him to be there, and also because she was not paying attention to that side of the road.