“Oh my god, I never know how to answer that question. I mean, I never was any good at trying to figure stuff like that out — what difference does it make after all? I mean, who really cares, except for you of course. I didn’t mean to offend you, I hope you didn’t take it the wrong way. But really, does it really matter? I don’t see how it does. I really don’t.

“But these days I am so distracted this kind of stuff throws me for a real loop. It really does. I just cannot stop my head long enough to get a grip on even the simplest, little bitty thing. I just can’t do it. It is totally and completely beyond me.

“Like this morning. I get out of bed and go to the bathroom and do my thing and then get ready for the shower. Now I like to exfoliate my skin every three days. Can I remember if today is the third day? Are you kidding? Of course not. I don’t have a clue. Not a clue. So anyway, I decided I’d skip it for today because that stuff’s so expensive and I get dressed and brush my hair and wouldn’t you know it, I hit a big tangle and almost yank this huge clump of hair out of my head. Now look at this — I don’t have all that much to spare. So I have to stop what I’m doing and untangle this mess and then it’s time for my nails and I can’t decide for the life of me what color polish to wear today.

“Now you wouldn’t think that this would be a big deal, would you? Time was, nail polish meant red and that was that. But that was before. Now I have almost a whole box full of the stuff and there’s bottles in there I haven’t used in a dog’s age but it’s still there and now I’ve got to match the color to what I’m wearing and what I’m doing and how I’m feeling and oh my god what’s a girl to do? I guess I’m supposed to flutter my eyelashes when I say something like that, aren’t I. I’m sorry, I’m still new at this. So anyway, I completely freeze up when confronted with having to pick out my nail polish. My brain, puny as it is, just decides it is going to shut it’s damn self down and it felt like I was standing there in front of my vanity for five hours or something waiting to decide what color nail polish I was going to wear. Ridiculous, I know, but that’s the way I am.

“So anyway, finally, I just reach in and grab something and it turned out to be OK because it was kind of a light, neutral beige that sort of goes with almost everything I have that I’d wear out in the daytime. But that just goes to show you, doesn’t it? I just can’t make a decision.

“Well, there was this one decision I made, but I can’t get into that right now.

“You know, my wife used to do all that sort of stuff for us. She always knew exactly what she wanted and how things were supposed to be done. ‘There’s always a right way to do something’ she’d say.

“Now she’s gone and I can’t even figure out what kind of nail polish to wear. You’d think I was a blonde or something.

“I guess I should have expected her to leave, but I didn’t. Sort of came out of the clear blue sky. One minute she’s there and the next minute she isn’t and that’s all th-th-that’s all folks. I guess I shouldn’t talk about it like that but I can’t get too serious about it because it still hurts. Oh boy does it still hurt.

“I still love her. But I don’t think she understands that.

“What I don’t understand is how she could leave me. I mean, just because this shirt buttons one way and another shirt buttons another way, what’s the BFD? I mean really, I don’t understand. Is it that big a deal that I like pants that don’t have a pocket on the butt? No, it isn’t. I don’t think so anyway. We’re talking about pieces of cloth, sometimes they’re arranged this way sometimes they’re arranged that way but we’re still talking about pieces of cloth, right? What’s the big deal? Am I wrong? Tell me if I’m wrong.

“I’m not wrong. Doesn’t seem to matter though.

“There was this one time we had to go to a funeral. It was late in June and it was hot. Really hot. You could see the heat rising from the pavement in waves. This was the funeral of the husband of a friend of hers and I didn’t want to go but we had to so we both got dressed in our funeral clothes and went to the church and graveyard and the get-together at a neighbor’s house afterwards. I must have sweated off about five pounds in my suit, but sometimes a man’s gotta do what a man’s gotta do — so I did.

“So anyway, we get home around five in the afternoon and it’s still hot. We head upstairs to the bedroom to change and she looks out the window and sees the guy across the street, sitting on his steps with his shirt off sucking down a Bud Lite. ‘You guys have it made’ she says to me. ‘I would love to take my shirt off when it’s hot but I can’t because I’d have every man for miles oogling me. Maybe even I’d get attacked or raped and he’d get off because I was asking for it. And you want to be a woman. Jesus.’

“Now I never said I wanted to be a woman. I don’t. I just like the clothes and I’d told her that before but it didn’t seem to sink in. But that wasn’t the point right then. ‘Honey,’ I said to her. ‘I’ve just spent that last four hours in a dark, lined, long sleeved suit over a starched, fully buttoned shirt and a tie. I’ve sweated like a pig and felt like I was trapped in a gabardine sauna. I have on socks and heavy black shoes. You’re wearing a little cotton dress and sandals and you look great. So don’t tell me you feel cheated ‘cause you can’t take off your shirt. Not until you’ve worn a suit in weather like this.

“That seemed like a pretty convincing argument to me. Not her, though. She just flung one of her sandals at me and stomped downstairs. Damn thing came within a couple of inches of hitting me, too.

“If she flung both shoes, I prob’ly woulda kept them. Aww, I’m just kidding. We didn’t even wear the same size. Ha ha ha, isn’t that just too funny. I’m being sarcastic, in case you can’t tell.

“We argued a lot in those days. We talked, we discussed, we fought, we considered, we rationalized, we blew up, we calmed down. We went to the library, we went to counseling, we surfed the web. Mostly, we drifted apart.

“You see, it all started when this friend of mine called me up. His divorce just became final and he wanted to blow off some steam and celebrate, so he called me. We did up the town right, but it felt sort of sad and hollow to me. I got home around three in the morning but as drunk as I was, I just couldn’t get to sleep. There was too much going on in this itty bitty brain and I stayed awake all night.

“When she woke up, I needed to talk. We had a good marriage, we really did. But I couldn’t keep my secret secret any more, if you know what I mean. If our marriage was really together, then being completely open could only make it better, right? How could being honest hurt anything if we both loved each other? It couldn’t, right? Aren’t I right here?

“What I couldn’t take was knowing that we weren’t being honest with each other, especially with me being the one doing the deceiving. I just couldn’t do that anymore. So I said, ‘Honey, can we talk about something.’ And I told her all about me. Actually, it was probably way more than she wanted to know or I wanted to tell, but once my mouth started working it got hard to stop. I have that problem, can’t you tell? And when I wound down, she didn’t say a word, which surprised the heck out me. I don’t know what I expected, but I didn’t expect her to hug me and sob quietly into my shoulder. It confused me in a big way, but I got used to being confused pretty quick.

“For a couple of weeks it seemed like everything was wonderful. I couldn’t imagine life being any better. We even spent an afternoon shopping together, although I saw her blanche white when I asked one of the salesgirls for directions to the dressing room so I could try on a skirt. I guess she was embarrassed or something, I don’t know. I wound up buying a blouse and she paid for it, but she made damn sure that the cashier didn’t know the blouse was mine.

“Those were the happiest days of my life. In my wildest imagination, I couldn’t have asked for anything more.

“There was this one day, I’ll tell you the truth, I’ll never, ever forget. It wasn’t even the whole day, it was just a moment…but this moment said it all. I’ll never feel like that again, but…Jesus Christ I still cry just thinking about it.

“I had this skirt I bought a couple of years ago. It was long, almost down to my ankles and I’m a tall girl, if you haven’t guessed. It was a patchwork skirt, mostly black with patches that were sorta floral and a combination of dark neutral colors, ivory and green, which has always been my favorite color. There was just something about the way it draped around my calves and flowed when I walked that was so nice. I loved that skirt, long before I talked to my wife. I’d purged a couple of times in the last few years but I always held on to this skirt.

“So anyway, this one time, I’m out shopping with her at this mall and she pops into a hardware store to pick up some bulbs for the light fixture we have on the porch and I pop into this clothing store and I see a display of sweaters marked down 50% because it’s February and they’re getting ready for spring. I see a bulky ribbed long-sleeved mock turtleneck in black in my size and I buy it. It’s the very first time I ever bought anything in a women’s store for myself when shopping with my wife, but by this time I didn’t think she’d mind and it all seemed so totally natural. I really and truly didn’t think twice about it. Just bought the damn sweater.

“So I’m still not quite sure how she’s going to take things, so I’m very careful. One step at a time, you know. Like, up to this point, I haven’t worn a skirt or dress in front of her. I’ve worn girls’ pants and tops and once even worn nail polish, but I haven’t tried makeup or skirts yet. At least not in front of her. I’ve been wearing skirts and makeup for 30 years, but, you know…

“So anyway, this one Saturday she decides she’s going shopping with a couple of friends and she’ll be out for most of the afternoon. As soon as she’s gone I zap myself upstairs, strip out of my boy clothes and put on undies, black tights and a camisole.

“About a month earlier I screwed up my courage enough to get a full makeover at the Estee Lauder counter at the local department store, so I had a complete set of tools to play with. I shaved again, started with the foundation and then tried as much as possible to duplicate what Marguerita did with me back then. The foundation and blush wasn’t too hard. The eyeshadow took a couple of tries. The goddamn eyeliner took forever because I just could not get that right. I kept wiping my eyes clean and starting over but after about 45 fucking minutes I got it right.

“When I finally got my eyes and lips and cheeks and everything else the way I wanted, I carefully combed my hair as neatly as I could and stepped away from the mirror, being as careful NOT to look at myself as I could. I didn’t want to spoil the total effect.

“So I went back into the bedroom and pulled on my skirt. Boy, I loved that skirt. Everytime I put it on I got a little thrill. Then I grabbed that sweater and pulled it on, being supercareful not to muss my makeup. The only thing left was shoes. I didn’t have too many shoes (shoes are expensive, you know. I don’t want to spend a fortune on something I’m only going to wear a couple of times) but I did have a pair of ankle boots in black that worked well with this skirt. So I dug the boots out of the closet and put them on.

“Just had a couple more things. I loosened my watchband so my watch hung like a bracelet. Then I grabbed one of my wife’s necklaces. Up to that point I had never, ever worn anything of hers. Really. I always had my own things. But for some reason, I thought it was important to wear something of hers right then. Back then, I don’t know why I did it. It was a total impulse. Now, I think I know. I think it’s because I know that she and I are really made for each other and I’m not complete without her. I know that sounds hokey and I know, given everything that’s happened, you’d have trouble believing it’s true, but it’s true goddamn it. It really, really is. At least now I know it’s true. Then, it was just some sort of instinct in the back of my head.

“So this instinct tells me I need to wear a necklace. My wife has great taste in jewelry (lousy taste in clothes, but that’s another story altogether). The first one I grab hangs a little lower than I’d like it to, so I take another. This one is made of yellow, amber and brown beads on a thick-ish chocolate brown strand with silver owls every couple of inches. I always liked it on her and thought it might look nice on me.

“Then I stepped in front of the mirror.

“One thing you gotta know is that I was gonna be 45 in two weeks. Now I’ve read all about mid-life crises and all that bullshit, but I never believed in it. Not a single fucking word. But one thing I do know is that this particular day I walked into a goddamn crisis and I don’t know if it was midlife or what. I just know it blew my life fucking apart.

“Because when I looked into the mirror, I liked what I saw.

“That’s all it took.

“For the previous 45 years, I’d looked in the mirror thousands of times. Millions maybe, and I’d never really liked the image looking back at me. I don’t know why — I never thought about it for the longest time. I just know that when I looked at that person with the black patchwork quilt skirt, bulky black sweater, amber necklace, honey ginger lipstick and plum eyeshadow in the mirror that I LOVED the person I saw. There was nothing rational about it. It was a totally emotional response but that didn’t matter. I LOVED that reflection. Then my rational mind kicked in and recognized that I was responding to that mirror image in a way that I had never responded to a mirror image before and ‘Oh boy, we’re in trouble now,’ it said. And every other synapse in my body replied ‘Fuck you, we like it.’

“For minutes I was mesmerized in this state. Not once in my entire life had I looked in a mirror and really and truly liked the person looking back at me and now I did. Except that now, the person looking back at me did not look like a man was supposed to look. My brain knew that I supposed to make something of it all, but my heart just kept responding to the image that my eyes saw.

“Then my wife’s face floated into the background of the image in front of me. I saw that image say ‘You goddamn fucking son of a bitch. Fucking goddamn faggot.’

“It took a couple of seconds for my brain to register that she wasn’t a figment of my imagination but was real flesh and blood.

“I remember that she reached out and grabbed my necklace — her necklace — and ripped it from my throat. Then she flung it into space. As she did it, she kept screaming at me. Vile, horrible things. I don’t remember a lot of it, but there are some things I just can’t forget. I can’t forget that she said I made her sick. I can’t forget that she said I made her feel dirty and sordid. I can’t forget the expression on her face.

“I also can’t forget that image in the mirror. And I can’t forget how I felt when I saw it.

“Anyway, we fought for about an hour or so before running out of steam. I slept on the couch that night and at a motel for a couple more nights that week. I came back and we were on and off for about three months. You know, we’d have four or five good days, then a fight, then a week of sulking, then a make up and a good week and then it would start all over again. She finally left.

“I think she made up her mind to leave when I told her that it wasn’t that I couldn’t stop dressing, but that I didn’t want to.

“I miss her every single day.

“But sometimes a girl’s just gotta do what a girl’s just gotta do, right? I mean, there comes a time when you have to do what YOU think is right. I just wish it didn’t take me 45 years to figure that out.

“Oh well, what the hell, isn’t that what they say?

“I’m sorry — I got carried away. What did you ask me?”

The bagger just stared at me with gaping eyes. “Paper or plastic?”

Connie

My name is Connie, which is short for Consuelo Sulllivan. I know, you don’t have to tell me that Consuelo Sullivan is a pretty weird name, but I can’t help it that my mother’s best friend for about a million years was a woman named Consuelo Dias or that my mother (whose name was Mary Dunleavy) was much more argumentative than my father, Mickey Sullivan. So 27 years ago, it became Consuelo Mary Sullivan. My mother died when I was about 6 and I remember her, but not very well. My father was a nice enough guy, but he didn’t understand his daughters all that well and his response to not understanding them was to ignore them as much as possible. So I grew up with a father I saw once in a while, his mother, his three sisters, my mother’s mother, my two sisters and Consuelo Dias. Mostly though, I grew up on my own.

When it was time to go to college, I wanted to go as far away as I could and to go to a big city and I wound up in Boston. I got an apartment with about a half-dozen roommates and it wasn’t long before I was Ms. Punkette. I got grades that were just about as good as I had to. When I was notified that I was going to graduate, I cleaned up my act for a couple of weeks, bought a dress and invited my father to my graduation ceremony. To my absolute amazement, he accepted. He came, we went out to dinner afterwards and when he got into a cab to go back to the airport, that was the last I ever saw of any member of my family.

For the next six years, I didn’t do much of anything worthwhile. I did some publicity for some rock bands (sang with a couple), worked in a pet store, was a bike messenger, a tour guide, a waitress in a diner, a waitress in a clam shack and a security guard. I must have passed out about 12 million flyers on street corners. The longest I ever held a single job was 7 months as a shipper/receiver in a bookstore. I never missed a rent payment, but I missed a lot of meals (I made up for it though, with lots and lots of Big Macs and Doritos).

So there I was, sitting by myself on Christmas Eve, watching TV and having my Christmas dinner of instant soup, BBQ Fritos and Bud Lite when I felt my life change. Of course the show I was watching was It’s a Wonderful Life, which I always thought was hokey as hell but watching It’s a Wonderful Life on Christmas Eve was as much a Christmas tradition as anything else I had. I was near the end of the show when all of Jimmy Stewart’s friends show up with money to help him out and the happy ending just oozes all over the screen and all of a sudden I felt absolutely, totally, miserable. I knew right then and there that this would never happen to me. I would always be sitting in my apartment (never a house, that would be impossible), sipping on instant soup watching It’s a Wonderful Life by myself every Christmas Eve from now on. I didn’t cry (I never cry) but I went to bed (alone of course) and when I got up the next morning I got dressed, took the subway downtown and spent the entire day just walking around the city thinking about how miserable I was.

By the time I got on the subway to get back home, I had decided that this had all got to go. I didn’t know what I was going to do, but it was going to be something different. And the first thing I had to do was to find a job that paid more than I was making now, which was $6 an hour for 20 hours a week. On the way to my apartment, I stopped in at an ATM and checked my balance - $461.37. God, I was pathetic.

Arthur

When I was 6 years old, my best friends were my next door neighbor, Lisa and another girl, Betty, who lived around the corner. We went to school together, played together all the time and just generally hung out together. We’d been friends since before we started going to school and it just seemed natural that we’d spend time together. One day while we were on the swings at the playground, I pushed Lisa higher and higher and then started saying something that I’d heard some of the other boys saying:

“I see England, I see France
“I see a little girl’s underpants.”

I giggled, but Lisa, after braking to a stop, asked my what was so funny about a little girl’s underpants. All I knew was that is was supposed to be funny, so I kept giggling but Lisa didn’t seem to think it was all that funny.

“So let me see your underpants,” she said.

Well, OK, I said to myself. So I unzipped my pants and pulled them down. “I don’t see anything funny about your underpants,” she said, and started swinging again, but this time not so high. When we got home, Lisa told Betty about the song I sang and how she saw my underpants and didn’t think they were very funny at all. Betty suggested that maybe it was just that it was girls underpants that were funny, so she went in the house and brought out a pair of hers that had little pictures of Disney’s Beauty and the Beast all over them. She handed them to me.

“What am I supposed to do with these?” I asked her.

“Put them on,” Betty said. “Then we’ll see what’s so funny about a little girl’s underpants.” Betty and Lisa were both giggling pretty hard by now. So I went behind the bushes beside the garage and took off my pants and my underpants and put on Betty’s underpants and then pulled my pants back on and went back to the girls.

“So let’s see ‘em,” Lisa said.

So I pulled down my pants just enough to show them and the girls both started laughing really hard. I didn’t know what was so funny, though, because I thought they felt really nice. Then Lisa said that it wasn’t fair that I was wearing pants because they couldn’t see my underpants when we were on the swings or were playing around. Then Betty in the house and got a dress for me to put on. I went behind the bushes again and put it on and then came back out and we played together for another hour or so before Betty’s mom called her in for supper. She looked at me funny when I knocked at the door a couple of minutes later to give Betty back her dress. I didn’t give her back the underpants because I couldn’t find mine and because I kind of liked them.

My mother didn’t say anything when I got undressed for bed that night and was wearing girl’s underpants. And I didn’t think anything about it when she started signing me up for afterschool activities. Soon I was playing soccer on Mondays and Wednesdays, piano on Thursdays and was in a book club that met every Tuesday at the library. That year I saw less and less of Lisa and Betty and I started making friends with some of the boys at school, I never met friends I liked as much as Lisa and Betty. And I never forgot that afternoon I wore Betty’s underpants and dress.

I don’t know whether I was genetically predisposed to be a crossdresser or that afternoon with Betty and Lisa set me off, but I can’t remember a time when I wasn’t fascinated by girl’s clothes. When I was 8, I was in a Christmas pageant as an elf and our teacher decided that we all had to wear red tights. Most of the boys were embarrassed and I pretended to be but I loved it. I can remember spending hours with the Sears catalog, not looking for toys but gazing at the underwear ads. When I was 11 I began raiding the dirty clothes hamper to try on my mother’s panties and it wasn’t long before I was trying on pantyhose, girdles, bras and eventually skirts and dresses. At that time my mom’s stuff was a little big but by the time I was 14 it was fitting pretty well and when I was 16 it was getting a little small.

The thing was, I just couldn’t get up enough courage to go into a store and buy something. Once or twice I steeled myself and marched right into a department store but I could not bring myself to actually tell a salesperson what I was doing. There was even one time when I grabbed a couple of pairs of panties and a nightgown in a discount department store (no salespeople to ask embarrassing questions!). When I approached the cash register and saw the teenage girls ringing and the customers waiting in line I panicked and dumped my stuff in a candy display and walked out of there as fast as I could.

I went away to a large state college in the middle of nowhere and tried as hard as I could to put this out of my mind. One night, long after most people had gone to bed, I was doing my laundry and I noticed that one of the dryers still had clothes in it. I peeked and it was a girl’s load! I made sure that nobody was looking, reached in, grabbed a pair of panties and stuffed them in my pocket. Eventually, I buried them with my own things and one day when I was in the dorm room by myself, tried them on. They were only a little too small but I felt like I was walking on air while wearing them. I stole a few more pair over the next few weeks and wore them as much as I could but a very close call one afternoon put an end to that real quick.

I graduated from college, moved to Boston, got a nice job playing with computers for a law firm and found my own apartment in a nice area. I told one girlfriend about my “interest” and she let me try on a couple of her things while we were making love but she was so much smaller than I was that it didn’t work and I looked and felt ridiculous. Another time I told a different girlfriend and almost immediately the frost machine kicked in and it became obvious that this was our last date.

After I’d been working with this company for a couple of years, I worked out a way for them to integrate this research database they’d been using with their own local network. This allowed the attorneys who were computer literate to save a tremendous amount of time on their research while allowing them to lay off a couple of clerical workers. I felt bad for the girls who were let go, but I got a $5,000 bonus, a raise and a new title out of it, so I didn’t feel bad for long.

The first thing I decided to do with my money was to pay off my credit card. The second thing was to buy a dress. And everything that went with it.

Connie

The first thing I had to do was get some clothes to do interviews. I didn’t own a single dress. I owned exactly one skirt and it was a shapeless India print that I wore on very hot days with a tank top. Everything else was jeans and sweats and T’s, with some leather & stud club wear. I washed the teal color out of my hair, removed the studs from my nose, looked for my neatest pair of jeans and my cleanest sweatshirt and headed off to the mall (gag!) to buy some clothes for interviews, whatever that meant.

It was like landing on a foreign planet.

I was in sort of a daze. I just wandered around for about a half-hour and then went into one of the department stores. I poked around the racks, wondering what people wore to job interviews. I saw some racks of middle-aged looking clothes and was pawing through them ($89.99 for a skirt!) when a saleswoman sidled up to me. “Can I help you find anything?” she asked?

I blushed, and then blurted out that I was looking for an outfit or two I could wear on a job interview. She smirked just a bit, and said “You might have more luck in the women’s department on the third floor. We only go up to size 12 here.”

I could have died. Not only was I badly dressed, now I was officially fat. I slunk out of there as inconspicuously as my grossly overweight and badly dressed body would let me and while I thought about going upstairs, I also thought that any store that was charging $89 for on skirt wasn’t the kind of store that wanted me as a customer. So I circled around the mall a couple of times and then went to the Burger King in the food court. Ordered a large chocolate milkshake and a large fries (it was too early for lunch, so I skipped the Whopper) and sat down to think. If I started with the $461.37 that I owned and then deducted the amount I would owe for rent in two weeks and added the amount I would earn at the convenience store where I worked nights, I figured that I could afford about $60 on an outfit if I limited myself to one meal a day.

So the department store wasn’t going to be where I started.

The sale rack at the fat lady shop (it was named Laura Brown’s Shop for Women) was where I started. I noticed that on the window it said “sizes 14 and up” and remembering what the bitch at the department store said, I figured this is where I belonged. This black woman with tits that went out to here and a butt that went out equally far in the other direction smiled at me and asked, “Can I help you find something?”

Man, this is what I was dreading. How can you not know the answer to this question? But I didn’t, so I swallowed hard and told her that I needed something to wear on a job interview but didn’t have a whole lot to spend.

“I know what that’s like, honey,” she said. “ Follow me,” and she waddled to the back of the store where the clearance items were kept. “We have a couple of things back here that could do you proud!” She riffled through the skirts on a these big circular racks and her hands landed on a bunch of khaki skirts that didn’t look too bad and then she asked me what size I was.

“Ummm, I’m not sure,” I mumbled, trying to be as nonchalant as possible. With that, she scooped up an armful (well, four) and said, “why don’t you try them on and see which one fits best.”

So I did and that’s how I found out I was a 16. As I was in the dressing room, trying to remember how to zip something that zipped on the side, my own personal salesperson was busy getting me a pale blue shirt and a skinny belt to give to me when I finally figured out which skirt I was going to buy. I accepted her stuff without a second thought (not that I even possessed a first thought at this point) and headed toward the register to pay for everything.

“Hold on a second, honey,” she said as she touched my elbow. “If you gon’ be wearing a skirt, you gon’ be needing something for your legs. You can’t wear socks with a skirt. You have something at home?” When it was obvious to her that I didn’t own a single pair of pantyhose, she reached for a package. When she saw my face begin to gag, she reached for a pair of knee-hi’s. “You can get away with these,” she said. “Don’t forget to shave, though,” and then she allowed me to go to the register.

The whole thing came to $64.96 and as I paid for everything, I figured that my shake and fries would have to be today’s dinner. As everything was being rung up, I saw a pad of job applications on the counter, so I filled it out and left it behind, paid for my interview uniform and headed home.

On the way out the door, my shopping bag caught on a security device attached to a velvet dress. As I swung my arm forward, the bag pulled the tag with it, until the rack was just about to topple over on to my back. As I turned around to see what was happening, the bag twisted the rack in the other direction and I kind of twisted with it to grab it and right it before it fell over. Except I slipped and fell flat on my butt, underneath the rack of velvet dresses that fell on top of my. When I tried to get up, I pushed the rack to the side and it caught the underside of a table full of sweaters, which when tipped all fell to the floor. I finally got up and began to try straightening everything up before anyone noticed, but my own personal salesperson and another woman in her 30s had reached the front of the store by that time. With their biggest, widest, most sincerest smiles, they told me not to worry and that everything was alright.

I hadn’t been that embarrassed since I wet my panties in the second grade. I went straight home with every intention of going to bed. It was 11:20 am.

Arthur

OK, I had decided to buy some clothes. So I jumped in my car drove to the mall, parked, took the elevator up the level where the stores began, stepped out of the elevator and froze. Solid. Like a statue.

What the hell and I doing, I asked myself. I was standing in a shopping mall with a flush credit card burning a hole in my pocket and visions that ranged from Madonna to Buffy the Vampire Slayer dancing in my head (my face on all of them of course) but no idea what to do next.

I suppose the thing to do was just to plunge ahead. So I did. I was closest to Macy’s, so I marched right in and there was the Intimate Apparel department staring me right in the face. What did I do? I charged right in!

And found myself in a veritable sea of panties. Row upon row of chrome stands with hundreds of panties hanging from them. White panties, black panties, leopard print panties, floral panties. Skimpy, lacy panties, big balloony panties. Nylon panties, cotton panties, silk panties, lycra panties. Sheer panties and opaque panties. Panties that cost 4/$10 and panties that cost $22.99. I was overwhelmed, so I did the logical thing. I froze solid again.

Until I heard some ask “Can I help you with something?” A girl who couldn’t have been a day over 17 was smiling at me. I must have blushed as red as the panties one rack over, two racks back, second tier on the left.

“Uhh, no. no thanks.” I spun around to leave and as I left I caught my sleeve on a rack of Wonderbras that I pulled crashing to the floor, right on a main aisle. I started to right it and a dozen or so slid off their perches and scattered to the floor. I didn’t know whether to bolt or cry, but that lovely young 17 year old came to my rescue. “I’ll take care of these sir. Don’t worry about it.”

I mumbled a thank you and slunk out. I began to think this wasn’t going to work.

Certain that everyone in the mall had seen me and was whispering that I was the man in the panty section who tried to steal a rack of bras, I went as inconspicuously as possible to the food court where I ordered a Coke and fries at Burger King and sat down at the most remote table I could find. I had to think about this.

The only thing was, no thoughts would come. Part of me knew that this was a thing that I had to do and the other part of was shouting that this was stupid and wrong and I didn’t know what I was doing. It was sort of a psychological pinball. In a little while, though, staring at the almost empty Coke and the congealed fries got to be a little old, so I got up, walked around the mall a couple more times trying to figure out what to do and then gave up and headed to my car.

I’d deal with this later.

Connie

Like I said earlier, I got home a little after 11. I got out of those clothes and sat on the edge of my bed in my underwear. I knew that I had to get dressed, get out and start looking for work but it just seemed so hard.

A little after noon (I knew it was after noon because Jerry Springer was over and there wasn’t anything else on until 1) the phone rang.

“Hello, this is Angela Hartford from Laura Brown’s. Can I speak to Consuelo please?”

Oh…my…god. I must have broken something when I tipped over the rack. Or they think I stole something. I’m going to die.

“That’s me,” I said in my smallest, most demure voice. It must have sounded like Minnie Mouse, or at least I hoped it did.

“Hi Consuelo. I’m the manager and I received your application. I’d like to set up a time for an interview.”

There was a long pause as I totally reoriented my brain. After squeaking out an “OK,” Ms. Hartford asked me if tomorrow morning at 10 would be too soon. I said that would be fine and we thanked each other and hung up. I wanted to have something to celebrate my first interview, but that would have involved leaving my apartment to buy something and that would have involved going to an ATM and getting some cash, which at this time of the month I didn’t dare do. So I satisfied myself by punching the air with my fist, dancing around the bed and waiting for Ricki Lake to come on.

Turns out the interview wasn’t much of anything, which means they must have been so desperate for help they would have hired a chimpanzee if it could fill out an application. Ms. Hartford and I chatted for about a half-hour and the only question that sounded like it was important was “Can you work weekends?” When I told her I could, I almost saw her putting my name on the schedule.

At the end of the half-hour, she asked, “When could you start?”

“Right now, if you want,” I answered.

“I don’t see any problem there,” and with that, she gave me a bunch of forms to fill out and I joined the ranks of the employed.

Arthur

When I got back home I sat in my car in my driveway for a long time but I didn’t find any answers there either. I fired up my computer and started surfing, looking to see if I could find a size chart or something. I went to LL Bean’s, Land’s End, JC Penny’s and about a half-dozen others, found what I was looking for on some of them and printed them out. Compared them all and found that I was a 14,16 or 20, depending on whether I was measuring my chest, waist or hips. The best I could do with a bra was a 40A and I couldn’t find a 40A in anyone’s on-line catalog. As for panties or pantyhose, forget it. I couldn’t make heads or tails out of anything.

Well, that weekend I went out shopping again, this time to a different mall, one with stores a little further down on the price scale. Well, it didn’t make any difference. As soon as I entered the women’s department, I shrunk up inside and was convinced that everyone’s eyes were on the freak in the dress department. The first store I went in was a discount department store and there were just too many people around and I quickly walked out.

The second store was an off-price store and it was a little crowded, too, but this time I figured it was time to, um, do it or get off the pot, so to speak. So I wandered around the store a while, picked up a pair of men’s jeans so I’d have something to drape over my arm and sort of sidled into the women’s section. I kept my eyes constantly looking around from side to side to see if anyone was going to freak out over me and at the same time tried to keep my head down so nobody would see me. I finally found the women’s size dresses (that was confusing as hell — aren’t all of these things for women? Why did they call the big & tall section the women’s section? And what in the world are missy sizes?) and then found the size 20s. I figured that I’d rather have something a little big than a little small.

I quickly flipped through the dresses and thought to myself that is was no wonder that these dresses were in a bargain store. There were a couple, though, that didn’t look too horrible and I grabbed one and headed to the register. Paid for it without the sky falling in and without being struck by lightning. I was almost home free. Just had shoes, stockings and underwear to go. Oh my god, I thought, I am going to die before this day was through.

Connie

The first few days I worked I spent most of my time unpacking boxes, putting clothes on racks and getting them ready for sale. It seemed like there was always something to open, unpack, hang up or pick up. I couldn’t believe how tired I was at the end of the day, but then again, I hadn’t really worked steady for a long time. I’m not sure I liked being a member of the working class.

On Saturday, I was going to spend my first day on the sales floor, so Friday afternoon Bettye (that’s how she spelled it — don’t ask me), the black girl with the big butt who helped me pick out my first skirt earlier in the week showed me how to run the register and helped me around the floor. It was so complicated. Codes for this and codes for that it seemed like I spent about 15 minutes on every sale just trying to figure out how to ring up everything up and what was on sale and what wasn’t and so on. What a pain in the butt!

Anyway, about half an hour before I was supposed to go home, this guy comes to my register and he’s got about a dozen pairs of panties in his hands and he sort of dumps them on the counter and looks down at his shoes. And I got to tell you, the guy’s sweating like a pig. I mumble a sort-of half-assed hello and begin to ring them up. Now a couple of customers ago, there was this woman who bought a bunch of panties and while ringing up the sale Bettye showed me that the cotton ones were on sale, buy two get two free. The nylon ones were 4 for $25 and the fancy nylon ones were free when you bought a matching bra or 3 for $25. Bettye and I were able to sell this woman a bra and two extra pair of cotton panties because of the different sales and she got a good deal. After all, she walked away with more underwear than I had back at my apartment.

But with this guy, it was like he grabbed the first two handfuls he touched. He had 6 pairs of cotton panties (which meant he was entitled to two more free), 3 pairs of nylon (which meant he had to pay the full price of $9 each) and one fancy pair but without the bra. I probably should have told him about all the specials, but he made me feel weird so I just rang up him to get him out of there. Gave me the willies.

After he left the store, Bettye looked at me. “What is your problem girl?”

“That was a guy,” I said.

“And so what?” she replied. “There are lots of guys who shop here.”

My jaw must have dropped because I knew my mouth was open but I knew that nothing was coming out.

“Well, I don’t know about lots of guys, but there are definitely some. Some of them are obviously pervs. They head straight to the underwear and run their hands all over stuff and you can almost hear them panting.”

I must have made a face because Bettye snorted back a laugh.

“Don’t laugh. Most of the guys who shop here are pretty cool. They know what they like and they don’t bother anyone. If some guy wants to wear panties instead of jockey shorts, who am I to say anything. I’ll just ring ‘em up and maybe suggest a bra to go with.” Bettye smiled and I smiled back but I still thought it was a little weird.

No, it wasn’t a little weird. It was a lot weird. I mean, I am a girl and have been one for 27 years and in all that time I never once gave any thought to my underwear other than knowing I supposed to wear clean ones in case I was in an accident. Not only that, I never once ever thought about wearing boy’s underwear. I mean, just how strange is that?

I know there are guys who do this — I remember seeing the news one day when Dennis Rodman was on in a wedding dress and there’s RuPaul and I’ve seen some of these transvestites (I guess that’s what you call ‘em) on Jerry Springer but you don’t think of people like that just walking around, y’know? It gave me the shakes.

Arthur

I don’t know how I did it, but I got through the rest of the day I picked up a pair of high heels at a discount shoe store, the biggest pair of pantyhose I could find at the drugstore and a three pack of cotton panties at the supermarket. The bra was the hardest part. I couldn’t figure out for the life of me how I was going to buy a bra. I just knew in the bottom of my heart that as soon as I gave a bra to a cashier to ring up, that bells would start clanging and a huge neon sign would drop from the ceiling that said “PERVERT.”

I decided that I could probably get away with it at Wal-Mart if I was smart. I hate Wal-Mart. I hate being in Wal-Mart, I hate Wal-Mart’s merchandise, I hate what Wal-Mart has done to the American economy. I just hate Wal-Mart, but I figured that if there was any place in the world that I could be guaranteed to be faceless it would be Wal-Mart. So I drove over to the nearest Wal-Mart I knew about (I was spending a lot of time driving around). This time I couldn’t pick up any clothes to disguise my true purpose (I wouldn’t be caught dead in Wal-Mart’s clothes, but I grabbed a ream of computer paper, a big bag of Doritos, and some trash bags before heading over the ladies clothing department.

What I wanted to get was one of those bras in a box, because I knew that I couldn’t bear fingering the ones on a hanger looking for my size or walking through the store with a bra hanging from my hand. So I sort of circled around the intimates department, waiting for the customers to thin out, then headed right to the bra rack. I was looking for a 40A but didn’t see one right away. I probably could have found a 40B if I was willing to spend some time pawing through the rack but my heart was beating louder than the cannons in the 1812 Overture and I had to get out of there, so I grabbed the first 40 I found (it was a D) and headed towards the register.

This was going to be the hard part — getting through the register. My hands were sweating so much I thought I’d soak through the computer paper but eventually I made it to the front of the line where this cute 18ish girl was ringing up sales. It was now or never. I clumsily dumped everything on the counter and the bra skidded off the trash bag box and slid off on her side. She picked it up, scanned it and stuck it in a bag and that was that.

And I was still alive.

After I got home I couldn’t wait to put everything on. I ripped apart bags, tore size tickets off, cut off tags and generally made a mess of my apartment. When I got dressed and looked in the mirror, I probably should have been disappointed.

The panties were a little small. OK, they were a lot small. The waistband wouldn’t pull up past my butt and they felt as if they were just about to fall off. They couldn’t fall off, though, because the leg openings were so tight that circulation to my thighs probably had stopped. The bra was OK around the chest but it looked stupid with all that unfilled material in the cup. So I filled it with socks, but do you have any idea how lumpy a D-cup filled with rolled up socks looks? The pantyhose were OK, except that I caught my toenail when putting them on and that started a run that went nearly the entire length of the hose.

All that was OK, though, because you couldn’t see any of it. The dress I bought was so huge, that I could have fit a friend or two in it without too many hassles. The shoes, on the other hand, were not only as undersized as the panties, they were really cheap (and I split the seam on the heel trying to put them on) and way too dressy for this dress.

And not of it mattered a bit, because I felt pretty. As far as I was concerned, the person staring back at me from the mirror was stunningly beautiful and I was high as a kite. Eventually, I came down from my high and when I did I began to recognize some of the, shall we say, flaws in my appearance. I also recognized that I really liked myself this way.

Where could I go from here?

Connie

Over the next few weeks, I got pretty good at my job. I learned everything about the registers, stocking clothes, keeping the place clean and organized. I even did a little selling on the floor, although I didn’t think I knew enough about the merchandise to actually help a customer. For crying out loud, I didn’t know enough to dress myself all that well. Bettye was a big help to me and most of the other girls in the shop helped me out from time to time but it didn’t take long before I started getting tired of having to ask somebody else if I looked OK.

It was one thing when I dressed deliberately ugly, but after spending a couple of weeks as a responsible adult, that just didn’t seem to cut it much for me anymore. It was something else altogether when I looked ugly by mistake. After this one particular day when Angela suggested that I stay in the backroom working stock I decided I couldn’t let this go any further.

I started coming in early and staying late after punching out to try on outfits, check sizes and see what worked and what didn’t. Some of the other girls thought I was crazy — after eight hours working in the store, they just wanted to get home. I didn’t have all that much waiting at home, and being embarrassed by wearing stupid clothes was something I just couldn’t handle again.

I never used to think that clothes meant a thing, but there was this one time when I saw myself in a dressing room mirror in an outfit from the store and I said to myself “Wow.” I looked damn good and I felt even better.

The first time I helped a customer put together an outfit that looked just right I felt almost as good. That was a lot better than schlepping boxes around or ringing registers. The harder and longer I worked, the better I got at it. It turns out that in the long run, the kinds of customers I was best with were women a little older than me who wanted to add just a little bit of spice to a classic look. I had trouble with younger customers because I wasn’t always real good at figuring out where the dividing line between sexy and trashy was. I also thought customers just looking for “good value” or older customers who always bought the same thing were kinda boring. I looked for ladies with some room on their credit cards and a taste for looking good.

Men still made me uncomfortable. Every once in a while we’d get some guy in the store but I’d try to find some work to do somewhere else. Some of the other girls would tease me about it, but I could put up with that. I mean, there were some guys who were buying gifts and they were fun to help. They seemed so cute and seemed so helpless and more often than not they didn’t care what things cost so I could sell them anything in the store. But guys who were there for themselves — they gave the creeps.

Now one Saturday, I spent about 45 minutes helping this guy buy a sweater that must have been for his wife or girlfriend or something and finally sold him a really pretty, soft grey fuzzy cowl-neck sweater that sold for $115. After I rang up the sale and the guy left the store, I bragged about it a little with Bettye. She just smiled at me.

“I thought you didn’t like selling to guys,” she said.

“This guy was cool. He was buying a present for his wife.”

“You think so, huh?” Bettye sort of chuckled. “A couple of weeks ago he bought more than $200 for himself — tried the stuff on an everything. He tell you this was for someone else?”

“Ummm, no.” I was getting a little red.

“Well then honey, you just had your first CD!”

“CD?” I asked.

“Crossdresser. That guy is going to look great in that sweater, but you probably should have tried to sell him those new black skirts we got in last Thursday, too. Would have gone great with it”

“Oh stop it.”

“Seriously. And I tell you what, honey,” Bettye wagged her finger in my face. “You better lose this hang-up you have. We’ll sell whatever we have to whoever wants it and we don’t want to get in any trouble from anybody ‘cause someone got a thing about men.”

I sputtered a little, but Bettye spoke up again. “I’ll tell you what. The next guy who comes in the store, you help him. And I’ll be watching you girl — you better help him the way he should be helped.”

I made a little noise, but I knew that I’d have to get over this hump, too.

And right then, this guy walked up behind us and cleared his throat.

Arthur

I never wanted to take off that dress, but eventually I did and as I put everything away I started to think how nice it would be to get some things that fit the way they should. Right now, the only thing I had that was the right size was the pantyhose and I’d ruined those. So I started to think about how to go about this. I couldn’t just walk up to a clerk in a store and say, “Excuse me, can you help my find a dress? I don’t know what size I wear.”

Or could I?

Here’s a brainstorm — I could come up with a cover story. So I thought for a bit about what kind of story I could tell and came up with this. I lost a bet and the penalty was to spend the day in drag. That could happen. Who could I lose the bet to? A buddy? No, I don’t think that would work. My girlfriend! Then I could get the lingerie, too. I lost a bet to my girlfriend.

What kind of a bet? That would be a little harder, but I decided to make it on a sports event. A football game. No, she beat me at tennis. That’s much better. That would do it.

As soon as the plan came together in my head, I just had to figure out where and when and I just couldn’t wait. I decided to go to the mall and just walk around until I got the courage to walk into a store. I felt like the Little Engine That Could. Can I do this?

“I know I can I know I can I know I can.”

I’m going to do this.

Late Saturday afternoon, close to dinnertime, I drove to the mall psyching myself up all the way. I parked the car, took the escalator up to the main floor and it deposited me in front of Macy’s. I took a deep breath and decided this wasn’t the place. The first store clockwise was a greeting card shop and then I saw Laura Brown’s.

Instinctively, I knew it was now or never. I inhaled deeply and then walked slowly not stopping until I almost bumped into two salesgirls who were talking to each other near the cash register.

Connie

The guy who cleared his throat also almost bumped into us. He looked really nervous, but nice. He was about my height (I’m 5’8”) and like me, a little on the chunky side without being fat (really — I’m not fat, it’s just that sometimes my thighs and boobs make me look that way).

Bettye grinned at me. “I’m going on break. See you in a bit.” And with that, I had my first guy customer.

“Hi. Can I help you with something?” I asked as brightly as I could.

He cleared his throat again. “Yes, I guess so. Promise you won’t laugh?”

I nodded.

“OK.” He took a deep breath. “I lost a bet with my girlfriend and I have to spend all day tomorrow in drag. And I really hope that you won’t think I’m weird and can help me out.” He exhaled and looked at me.

Now I’m not the world’s most perceptive person, but I know bullshit when I hear it and there wasn’t the slightest hint of truth in what he just said. But I did remember what Bettye said to me so if this guy wanted to get some stuff that was his business and it was my business to help him. “So here goes,” I said to myself. To him, I said, “I won’t laugh. Actually, I think it’s kinda cute.”

I could swear he blushed a little.

“So what are you looking for?” I asked.

A brief moment of panic zipped across his face. “Actually, I don’t think I really thought about it. It was just hard enough coming in here. I don’t know what I want. Whatever you suggest will be fine, I guess.”

“Well, OK. We’ll see about that. My name is Connie. What’s yours?”

“Arthur.” I was pretty sure that was his real name, too, because he answered too quickly to have thought about giving me a fake name and nobody would willingly pick a name like Arthur.

“Alright then Arthur, let’s get started. You said you’re doing this for a bet, right?”

He nodded.

“So do you want to play this for laughs or do you want to do it straight?”

Arthur looked a little confused, so I had to clarify things for him.

“Do you want to camp it up and get something really sexy or maybe something real conservative that will embarrass you as little as possible like maybe a tailored pants suit or do you want to get something that looks nice and stylish or something frilly or what? I’m trying to figure out which direction to go here.”

He thought for a second or two and then blurted “No pants.” Then after another second or two, “My girlfriend wouldn’t like that. I guess I just want something nice that won’t make me look too silly.”

“Is that how your girlfriend wants you to play it?” My throat caught a little on the word “girlfriend.”

“I guess so.”

“OK. Next question. Do you want underwear too?”

He must have blushed about 12 shades of red as he stared down to the floor and nodded. This was getting to be fun. I pretended not to be able to figure out his response.

“I’m sorry, Arthur, was that a yes or a no?”

“Yes”

“Good. What kind?”

He looked at me utterly confused. “What kind?” Actually, the look he gave me really did look confused — he wasn’t hiding something, he really didn’t know what I was asking.

“Well, I mean a couple of things. Are you looking for a camisole and half-slip, a full slip, bra, girdle…” I let my voice trail off.

“I guess a bra and…” Now it was his turn to trail off, but I wasn’t going to let him off the hook, so I just smiled and waited. Finally, he almost whispered “panties.” Then he paused a bit and looked away and added “and a slip or half-slip if what you pick out for me needs it.” Which told me that he had done some studying on the subject, even if he was working real hard to pretend he hadn’t.

“That’s no problem, we’ll take care of it.” Now for the zinger. “Now, once you tell me your sizes, we’ll be able to get right to work.”

“My sizes? I don’t know my sizes, I’ve never bought women’s clothes before.”

I noticed that he didn’t say he hadn’t worn women’s clothes, just that he hadn’t bought them. Cute. I was about to start having some fun with him again, but there was something in his face that stopped me. This guy wasn’t at all like the sleazy pervert I thought a guy who wore women’s clothes would be. He actually seemed embarrassed to be here, but almost as embarrassed that he didn’t know his size as he was over being here in the first place. I mean, he really seemed like Joe Average, except that I’d never had to figure out what size skirt Joe Average wore before.

My disdain was turning (a little) to pity.

“Don’t worry, I can take care of it.” I said. “Why don’t you follow me to a dressing room.” I noticed a flash of terror passing over his face. “Relax, Arthur, everything’s going to be fine. I’ll get you all dolled up and won’t charge you an arm and a leg, either.” With that, I led him down to the dressing room that would be the most private and left to find my tape measure.

Arthur

Immediately after blurting out my story I knew it sounded as phony as a three dollar bill and part of my brain was urging my feet to run out of there as fast as they could go. The other part of my brain was telling me that if I’d already made this much of a jackass out of myself, how much worse could it be? In the end, I couldn’t refute that kind of logic, so I didn’t run away.

I don’t know what I expected. Maybe I was thinking that once I whipped out my trusty (HA!) cover story that I’d waltz out of the store looking like, I don’t know, Jennifer Aniston? (although Jennifer Love Hewitt is more my color and type). What I didn’t expect was to receive the third degree from a saleswoman but once I spent two seconds thinking about it I knew I she was just doing her job.

The “she” in question was the salesgirl who was wearing one of those carved plastic name badges that said “Connie.” She was almost as tall as me (but I’m not all that tall, to tell you the truth) but a little on the chunky side. Not fat, but her hips and thighs were plenty rounded and she was pretty generously endowed up top, if you know what I mean.

The thing I noticed most about Connie, though, was her face. She had a wild head of untamed reddish-brown hair that framed face and it was a big, warm, friendly face. Big red lips (and I don’t think she was wearing lipstick, prominent, fleshy cheeks and bright blue eyes and a smile that just couldn’t quit. Every once in a while I got the feeling that she wanted to let loose with a huge guffaw but was working too hard at keeping herself reined in.

So she’s asking me all these questions and I’m trying like hell not to let on how turned on I am or how embarrassed I am. And then she tells me to hit the dressing room and I almost freaked! It never occurred to me that I’d have to try anything on. I thought they’d just know what size I’d wear. There is no way in a million years that I’d be able to actually put something on in a store. In a goddamn public store! What if someone saw me? Connie’s going to know that I’m actually wearing this stuff! What if someone freaked because they saw a man in the dressing room? This was going way too far but Connie didn’t seem to be fazed as she led me to the back of the store, opened the door and indicated that I go inside.

Instant paranoic meltdown. If I could have pulled the floor over my head and disappeared, I would have. I must have been sitting in gallons of sweat and my hands were shaking, but when Connie came back with a tape measure, she didn’t seem to notice. She asked me to raise my arms and she wrapped the tape measure around my chest, then dropped it an inch or two and did it again. Then she measured my waist and then wrapped the tape measure around my butt.

“A perfect 42-38-40,” she giggled. “I’ll be right back. Don’t go anywhere” And she went off towards the front of the store.

I knew the outfit I wanted and I prayed that she’d bring it back to my dressing room. They had it displayed on a mannequin just inside the window. It was a two piece dress in a rich, dark, red with black, abstract floral pattern constructed out of thin, delicate lines. It has elbow length sleeves, a V-neck that didn’t plunge too deeply and a notched collar but it was the gorgeous color and the way the full, calf-length, bias cut skirt draped across the mannequin’s legs that set my heart to quivering.

It wasn’t what she came back with.

“I thought you might like something like this. It’s a skirt set, but it’s not real frilly and it’ll be easy to wear.” Connie gave me the skirt and top. “Try these on and let me know.”

It was a navy blue knit two piece dress with three-quarter sleeves and a scoop neck. The skirt was probably supposed to be a couple of inches below the knee and all in all, it was pretty boring. Now I’m saying that it’s boring. At the time, I was tingling with excitement.

So I closed the door to the dressing room, took off my pants and shirt and put on the skirt and top. Wasn’t all that hard at all. Right.

I avoided looking in the mirror until I was dressed because I wanted my first glimpse to be, I don’t know, ceremonial. Everything felt like it more or less fit, so I slowly turned around to face the mirror.

I don’t know what I expected. Well, yes I do. I expected to be dazzled by a radiant feminine beauty staring back at me. That, or for the sky to open up and a bolt of lightning to strike me dead for wearing a dress in a public (well, sort of public) place. I didn’t expect to see me, wearing a dress that looked lumpy.

Lumpy was exactly the right word for it. It was a clingy sort of knit, and since I didn’t have anything upstairs to push things out a bit, the top hugged every curve and line I had, including a little run around my less than A-cup, the beginnings of what would become a pot belly if I wasn’t careful and love handles that I didn’t remember having. All that was pretty bad, but it wasn’t as bad as the bulge between my legs or the fact that the skirt showed every line of my bunched up boxers. The hairy legs covered by white athletic socks sticking out from the skirt didn’t help either.

Connie knocked once, saying “Knock knock.”

I gave her an absent-minded “Yes,” as I continued to pick out flaws in my appearance.

She interpreted that “yes” as permission to enter and opened the door. I panicked, but there wasn’t much I could do besides stand as rigid as a rock and blush. She grasped my shoulder and turned me around to face her. “Well,” she murmured, almost to herself, “I think we have the size right but this won’t work at all.” She raised her voice a little and looked me in the face. “What do you think?”

“It’s OK” I lied.

“We can do better than this, though. Seriously.”

“Whatever you say.” I tried to grin but it must have looked as weird as the rest of me. “You’re the expert.” That got a bit of a giggle out of her.

“Well, if you don’t mind, I’d like to try something else. Y’know what else?” She paused thoughtfully. “I think we probably ought to get the underwear done first. It’s hard to get a good fit with what you have on now.” Her giggle got a little louder.

My blush got a little deeper. I managed to eke out an “OK.”

“Alright, let me see what I can do. Do you have any preferences?” She was loving this, I could tell.

“Uh, no. Just a bra and, uh, uh, underwear.”

“No problem. Just wait here. Oh, by the way, you’re an 16, same as me,” and with that she headed off towards the lingerie section. I, in the meantime, shut the door as quickly as I could and huddled in the corner, waiting for her to come back.

Connie

This was turning out to be as much fun as I’d had in a long, long time. This guy Arthur was a nice enough guy, I guess, but it was so easy to push his buttons.

When I went to get a dress for him, I was trying to think of something as embarrassing as possible, something really femmy or maybe a tight miniskirt, but I didn’t want him to think I was playing him. Then I thought I could have some fun if I got him something boring and really ugly, so I got the two piece navy knit — something some big mama might think would make her look sharp. The thing was, when I put it on him, he looked so disappointed it (almost) broke my little heart. He looked really sad and I felt like I was being cruel and I didn’t like that feeling one bit. I mean, when you think about it, what was he doing that was all that wrong?

So anyway, I’d have to put a little more thought into this. Or maybe less thought. Maybe I should just pretend he’s like an everyday customer and not a guy. Yeah, like that’s going to happen, I thought. Then this other voice came right back and said why the hell not? These conversations with myself were getting a little weird.

By this time, I’d made it to the lingerie department and had to decide to do something. He did look to be about the same size as me, which meant he probably was going to wear a size 8 panty or maybe even a 7, because while his waist was about my size, his butt sure wasn’t. I’d measured his chest earlier and knew he’d wear a 40 bra (and at that, one of those little voices in my head giggled that they don’t wear 40 AA’s). I hadn’t asked him if he was going to stuff his bra and I couldn’t really think of a diplomatic way to ask.

I also hadn’t asked him how much he had to spend. I didn’t know whether he wanted something really nice or just something cheap.

After seeing the look on his face when he tried on that ugly dress, I decided to go with nice. I also heard something in the back of my mind that said I needed to make it up to him for picking that dress.

There was this one matching set that was really, really pretty. I mean, it was so nice even I’d thought about getting some for myself. I hadn’t, because (a) they were way too expensive for my bank account, even with my employee discount, (b) all my life I’d only thought about underwear in functional terms and the idea of pretty underwear seemed a bit strange to me and (c) who was going to see them — it wasn’t as if I had a hot social life.

The bra had stretch straps with some understated scalloped edging on the sides and back. The top half of the cups were translucent with a tulip pattern embroidered in lace. There was a tiny tulip in the middle where the two underwires met. The panties had the same tulip-embroidery on translucent material rising in a V from the crotch along the leg with the tulip motif continued in a tone-on-tone pattern all over. A little tulip at the center on the waistband added just the right accent. The bra was $26.95, the panties $15, buy two get one free and we had them in white, black, red, burgundy and purple. I picked the white for him as a symbol of his (probable) virginity (that voice giggled again) and brought them over to his dressing room. I guess I wondered what he had been doing all this time.

Arthur

After the salesgirl left I didn’t have a clue what I supposed to do next. Was I supposed to get back into my clothes, say in this dress, take the dress off and stay in my underwear or what? What had I gotten myself into? I decided to do nothing.

“Knock knock,” I heard her say and I opened the door. I could swear she smiled for just a second when she saw I was still in the knit dress.

“Why don’t you put these on. You could try the panties on over your boxers, but I don’t think that would work very well, but I’m pretty sure these will be OK. Do you need some help with the bra?”

I blushed very deeply and shook my head violently to indicate no.

“Alright, then. After you put these on, you could try this dress again and see if it makes any difference having the right underclothes.” She started to walk away. “Oh, by the way, I didn’t know what you wanted to do about the cup on the bra. I got a C cup for you, because if you plan on stuffing it a C cup would look about right on someone your size. If you didn’t want to stuff, I could go look for a smaller cup.”

“No, this will be fine,” and I took the bra and panties from her. We stood in awkward silence for a moment, then she started to pull the door shut.

“OK, then. Holler if you need anything and I’ll go look for a different outfit.”

Right. Like I was going to holler for anything. I peeled off the dress and then slipped off my boxers and I can’t tell you how strange I felt being naked in a women’s dressing room in a store in a mall. Connie was right, the panties did fit just right. A little snug around the legs, but they hugged my ass just right and I just loved the way I looked in them. They were so pretty.

I put the bra on backwards, hooked it up, slid it around the right way and then slipped my arms through. It fit right, too, except for the cups. I could probably stick a pair of socks or two in them when I got home, but I wasn’t really thinking of that right now. Right now, I was staring in the mirror at this guy who was wearing the absolute prettiest matched panty/bra set I’d ever seen and that guy was me! Damn! This is fun!

I pulled the knit dress back on and it did look better without my wrinkled boxers underneath it and with a little forward motion up top, but it still wasn’t the image I had in my head. Just the same, though, I could get used to this. I was beginning to convince myself that this is what I wanted.

Then Connie did her “Knock knock” thing again.

Connie

So what could I pull together for this guy (and why did I care so much, all of a sudden)? I mean, I could probably wrap him up with what he had now, make my commission and never see him again and everything would be cool but that just didn’t seem right. I actually wanted to get the right thing for Arthur and I couldn’t quite figure out what that was.

Pants were out of the question, as were mini-skirts, shorts, dressy dresses, career separates and a good deal of our basics. I was having a hard time coming up with something and then my eyes landed on our window. There, I saw the perfect outfit for him. It was a dark red two piece dress that would have come almost to my ankles, with a very pretty, very subtle black floral pattern. It was soft and feminine without being frilly and I remember that even I took a second look at it when Lisanne, our receiver, unpacked it. I even remember thinking that with Arthur’s finely chiseled features and dark coloring that it would look good on him, although I can’t for the life of me imagine that a dress would ever look good on a man.

I almost ran over to the rack and checked for sizes — 14, 18, 24, 26 — no 16. For a second I thought about showing Arthur a 14 and an 18 and seeing which worked best, but then I had a hunch and checked the mannequin in the window. BINGO! A 16! So I stripped the mannequin as quickly as I could (stabbing myself with hidden pins a couple of times in the process), shook the dust off the dress, regained my breath and brought the dress over to Artie (I’m sorry — I just can’t call someone Arthur without thinking of an aardvark).

“Knock, knock,” I said and opened the door to give him the dress. The expression on his face was totally priceless.

Arthur

She brought me THE DRESS. This was the dress I saw in the window that I almost drooled over. Of all the things in that entire store that I wanted to wear, she brought me exactly the right thing. I almost fainted. I did, I really almost fainted.

Then I remembered that I wasn’t supposed to like this and this was all for a lost bet and as fast as I could I tried to get hold of myself. I have no idea how well I did at it and I have no idea what Connie must have thought about my reaction to the dress. I felt like I was drenched in sweat and my heart was hammering but I mustered up every bit of nonchalantless (I know there’s no such word but I it’s the only way I can describe it) and took the dress from her.

“OK,” I said. “I’ll try this one too.” I tried to heave a tired sigh, but it probably sounded more like hyperactive panting. The expression on Connie’s face as she closed the door was pretty bizarre. I couldn’t tell if she was amused, amazed, shocked or even a little scared. To tell you the truth, though, I didn’t care a bit. I just wanted to see how I looked in that dress.

As soon as the door closed, I almost ripped that navy monstrosity off me, flinging it in the corner. I lifted the top over my head and allowed it to float over my body and without even glancing in the mirror (I didn’t want to spoil my first look) I pulled the skirt up around my waist, adjusting it just so. Then I turned around and faced the mirror.

And I loved what I saw.

Whoever made that dress, made it for me. It draped over my body in the most languorous, sensual way possible. The deep, dark red color was perfect for me and the subtle black decorative lines mirrored the subtle, dark lines of my eyes, brows and lips. I was transfixed and the longer I looked at that mirror, the better I liked it.

Forget no makeup. Forget short hair. Forget the athletic socks. This person in the mirror just looked so right. When I slipped off my socks, I almost swooned as it made what was already perfect better. For the first time in my life, I didn’t feel like a freak. I felt like this is the way I should look.

Connie

I didn’t know what was taking so long inside the dressing room. After clearing my throat a couple of times, I thought I ought to do or say something, so I asked “Everything alright in there?”

He didn’t respond for a beat or two, then squeaked out an “Uhh, yes. Everything’s fine.”

“How does it fit?”

I heard him clear his throat. “Fine.”

“Does it look OK?”

A little more throat clearing, then a low, soft, “Yes.”

“Can I see?”

Another pause. “Do you have to?” he asked.

That was a good question. He was the customer. If he’s satisfied, why should I care? I did care, though. There was something about him that piqued my curiosity and I also wanted to know if my take on the dress was right. “No, you don’t have to, but I’d like to see how you look anyway.”

Another pause that stretched into a few seconds and then he slowly opened the door.

I gotta tell you, I was amazed. Shocked almost. As the door was opening, I was steeling myself to keep from giggling, but when I finally saw Arthur in that red dress giggling was the furthest thing from my mind. He looked good. He really and truly looked good in that dress.

Now I know he would have looked better if the bit of leg that peeked from under the hem was shaved and a different hair style would have improved things, too, but even with all of that he looked good. The color was right, the fabric was right, it hung on him right and it fit just right.

Most of all, though, it was the expression in his face that got me. He knew how good he looked in that dress and it was like a revelation to him. He was positively radiant.

I have never, ever seen a customer react that way to anything I selected. To tell you the truth, I was as confused at that moment as much as I’d ever been. I thought I would have been a little, I don’t know, either irritated or smug at having just helped a pervert but his reaction to the dress took the winds right out of that sail. I should have been pleased that I helped a customer find what she (she? he?) wanted, but that wasn’t quite what I was feeling either.

I was jealous.

I was jealous of him. Not once in my life had I ever felt really good because I looked good and here was a guy (a fucking GUY!) standing in front of me in a dress I sort of liked but couldn’t afford who looked a hell of a lot better than I did and knew it. I was jealous and as soon as I recognized the fact that I was jealous I nearly freaked but then brought myself under control real fast before I let things get out of control. This was something I’d have to deal with later. Much later, I hoped.

“Not too bad, is it? What do you think?” After all that, all I could manage was something stupid like that, but what was I supposed to say — “That dress is you!” Ugh!

He smiled to himself for just a moment. “I think it’ll be OK. I can go with this.”

“You sure?” I asked. “I can show you some more,” and I laughed, as if letting him in on a joke.

“No, this is OK.”

“Alright.” I didn’t know where to go with this. “Why don’t you get dressed and I’ll ring you up. You can leave the other outfit there, I’ll take care of it.” I paused for a moment. “You don’t really need a slip with that, but what about pantyhose?”

“Pantyhose? I guess so.”

“What shade?”

“I don’t have any idea.” He was almost whispering by now. “Whatever you think is best.”

“Alright, I can take care of it. I’ll meet you at the register.”

On the way back to the register, I picked up a pair of suntan, nude toe pantyhose in a size I thought would fit. I remembered that they were on sale, 3/$15 and on a hunch I added two more, one in nude and one in coffee. Riding that same hunch, I added a couple of pairs of panties, one in red, one in black. They were buy two get one free. I wanted to see what would happen.

Arthur

I did not want to take that dress off, but I knew I’d have to. Off it came, carefully and lovingly and gently placed back on the hangers. I slipped off the panties, unhooked the bra and put my “real” clothes back on. What a comedown, but I knew I’d done the right thing. I couldn’t wait to get home.

As I came out of the dressing room, a mother and daughter were browsing the clearance rack nearby and gave the man with the dress, bra and panties draped over his arm a strange look, but I hardly noticed. I headed to the checkout, where Connie was fussing with something beside the register.

“All set, I guess,” as I laid my things on the counter. “I have to thank you for this. You were really helpful and I really appreciate that you didn’t get all weird or anything,”

I thought I saw her smile to herself. “No problem at all. That’s what we’re here for.” She straightened out my purchases and then added a couple of things on top.

“The panties are on sale, buy two get one free. That’s a really good deal, so I picked out another couple pairs for you. And these pantyhose are on sale, so I got three pairs for you. You don’t need to buy them all, but it’s such a good deal I thought you might want some extras.”

Another moment of truth. This was supposed to be the losing payoff in a bet, so why would I need more than one of anything? On the other hand, it was a good deal and why shouldn’t I have a couple extra panties? On the other hand, if I bought them, it would be like telling Connie that I liked this stuff and wanted to wear it. On the other hand (how many hands did I have?) there was something about her I trusted.

“Go ahead,” I said. “I’ll take them.”

This time when she smiled, it wasn’t just to herself. She looked so pretty when she smiled.

Connie rang up the sale, processed my Visa, carefully folded up my new wardrobe and bagged it all. She was chattering amiably all the time, but I don’t think I heard a word she said. I couldn’t focus on anything besides getting back to my apartment.

Finally, she handed me the bag. “I hope your, uh, girlfriend likes the dress. You do look good in it.” Her smile was warm, affectionate and genuine.

“Thanks. You really were a big help.” I wanted to say something else, but nothing intelligent would come out. I just smiled and nodded and started to leave.

Connie

He was so grateful. He made me feel as if I had done him a huge favor and when I thought about it, all I did was help him with an outfit. No biggie.

Yeah, right. In my mind, Arthur had traveled the distance from a panting pervert to a really cute puppy in a very short while. Was I confused? Not at all. Almost everyday I select panties and a bra for a guy and then try to get him to talk to me (and ask me out? maybe?). Happens all the time.

As he started to leave, I wanted to say something, but “have a nice day” or “thank you come again” didn’t quite cut it. So I just blurted “See ya,” except my voice sorta broke and it came out as a question.

He tilted his head, smiled, blushed a little and nodded. I couldn’t figure out what that might have meant. Then he was gone.

Arthur

All the way home my mind was whipping from one thought to another. I thought of the dress, of me in it, of me in a dressing room in a store, of the bra and panties, of just being in a woman’s store.

I also thought of Connie.

And when I got home, before I started to change into my new clothes, I called the florist and sent a dozen roses to Connie at the store. I had the card signed “Thank you so very very much. See ya. Arthur.”

John looked in the mirror and sighed heavily. “It’s never perfect,” he said to himself. He has lost nearly 20 pounds in the last five months, but it looked like everything came from his waist – which was great. Everyone wants a trim waist, right? The thing is, none of the weight loss seemed to come from his chest and he was a little flabbier than he would have liked. As he looked into the mirror, two perky nipples looked back, supported by two soft mounds that were clearly visible under his T-shirt.

His hand absently rubbed his chest, feeling the soft flesh that had once been firm. He was not happy with the unexpected side effect of breasts. They jiggled a little when he walked.

Rachel snuck up behind him, gave a big hug and then pinched his nipples. Her eyes had lit up with mischief as she when she noticed John quiver at her touch. She had been merciless recently in her jests about her husband’s newfound "cleavage." At first, she just tweaked his nipples or occasionally cupped his breasts. She was delighted as his weight loss – he was healthier and looked a LOT better. But while John was worried about his emerging breasts, Rachel was thinking they had a new plaything. Tonight, she was feeling particularly mischievous.

“You know what – you need a bra!” she said. You have manboobs. Titties! My John’s has titties,” she squealed while tweaking his nipples some more.

“I do not,” John said, brushing her away. He couldn’t help but feel the electricity coming from his breasts or the erect nipples poking through his shirt.

“Do too, honeybunch,” she replied. “I bet you have a pair that are as big as mine.”

“Stop it!” John commanded, getting uncomfortable with how this conversation was going.

“Stop what – this?” Rachel said as she ticked his nipple with her left hand and then caressed his crotch with her right. “It doesn’t feel to me like you want me to stop.”

John stepped away, but Rachel stepped with him, cupping his boobs and giving him a deep kiss. “We need to get you a pretty bra to support those gorgeous boobs sweetie. They are too pretty to let them go unadorned.” She nibbled his neck while caressing his boobs. “Just imagine how sexy you’ll feel with those beautiful boobies lifted with a sexy bra so I can do this –“and she dipped down and put one of his breasts in her mouth and bit gently then sucked hard.

John shivered with excitement but again took a step back. His brain was telling him that men don’t get off by having their tits sucked but his breasts and his cock were telling him something else. He stepped back again but now his back was against the wall.

She started kissing his neck. In between kisses she murmured “We’ll get you a beautiful, sexy, hot bra for those beautiful, pretty boobs. You will love how you look, how you feel…”

“No!” he blurted. “We’re not going to get me a bra.”

She continued nuzzling him, “I understand, sweetheart. I understand. You’d feel nervous shopping for something so feminine, so luxurious, so lovely. I’ll get one for you, something special just for you, for your beautiful boobies.”

John was getting excited, moaning “oh yes yes” as Rachel’s caressing and kissing progressed.

“We can go out tomorrow night and get you our own beautiful, sexy, bra. Won’t that be wonderful.” She started biting his nipple again while rubbing his crotch.

“Oh yes,” John gasped. “yes. Wait, what?” Something didn’t quite register for John.

“You said you wanted to go out with me tomorrow to buy a bra. Didn’t you just say that?”

“Yes. No. I don’t want to go out with you to buy a bra.”

“That’s so sweet – you want to do this by yourself!” Rachel beamed. “That’s so sweet – I can’t wait to see what you get.”

John was completely confused by this point. He was totally turned on and didn’t understand what Rachel was saying to him. He leaned into her but this time she stepped back. “So it’s settled! tomorrow after work you’ll get yourself a bra and we’ll pick this back up.”

As John began to object, Rachel said “you aren’t afraid to buy a bra are you?” There’s nothing to be scared of,” she purred. “I buy them all the time.” She smiled at him mischievously and stepped gently out of the room, leaving John to figure out what just happened.

Before going to bed, Rachel reminded John of his commitment. She mentioned it again at breakfast and again as he kissed him goodbye as he headed off to work. John thought a couple of times about how he might get out of this, but he didn’t want to seem scared. At least that’s what he told himself. In the back of his head he also wondered where this was going.

That evening, John pulled into the parking lot at Target, thinking that a large, impersonal store like Target would probably be the safest place for him to go. He walked past the greeting cards, kitchen appliances, pet supplies, and shoes before reaching the clothing section in the back. He looked for lingerie and walked towards that department, trying to be as inconspicuous as possible.

Once inside the lingerie section, John's eyes were immediately drawn to the vast array of underwear. The racks of bras and panties stretched out before him, a kaleidoscope of lace, satin, and mesh. He swallowed hard, trying to ignore the heat rising to his cheeks. There were so many sizes, so many styles, and so much more variety than he could have ever imagined. He felt like a fish out of water, his eyes scanning over the garments – some delicate, some looking like they could protect Fort Knox - with a mix of curiosity and trepidation.

Finally, he mustered the courage to grab a half-dozen bras that he thought might fit. The fabric was surprisingly soft, and he couldn't help but feel a strange thrill as his fingers brushed over the smooth material. He hurriedly dropped them into his basket and sneaked into a dressing room, his heart pounding in his chest. John took a deep breath to calm his nerves before he began to try them on.

The first bra was a simple, white, sports-style number, which seemed like a good starting point. He struggled with the clasp, fumbling like an awkward teenager. Rachel's giggles played in his head, and he scowled, determined to get it right. After a few frustrating moments, he managed to fasten it around his chest, the cups enveloping his newfound breasts. He stared at his reflection, the unmistakable outline of the bra visible under his shirt. The sight of it made him feel both ridiculous and oddly aroused, a sensation that was entirely new to him.

The bra was snug, almost tight, but there was way too much material around his boobs, creating a puffiness that made him look like a pigeon. He sighed, adjusting the straps and cups, trying to find a way to make it work. The fabric felt foreign against his skin, the wires digging slightly into his flesh. Yet, there was something about the way it hugged his body that sent a thrill through him, a feeling of being both confined and supported that he hadn't anticipated.

With a new sense of determination, John took the white bra off and reached for a black lace number he had brought into the dressing room. He slipped it on, the cool material caressing his skin. The lace was a stark contrast to the plainness of the first one, and the way it hugged his body was more intimate, more alluring. But when he looked in the mirror, he saw that the cups were still too large. There was no hint of John’s actual breasts buried in the fabric of the cups.

He kept trying bras on but none of them fit properly. Sometimes the bra as too small around and he felt strangled as he fastened it. If the bra came close to fitting around, the cups were always too big. He dropped this group of bras off at the unattended service desk and picked up a few more to try on. He found one that fit reasonably well but it looked like something you’d wear at the gym, and it was the opposite of sexy.

He tried on the last of this second group of bras. As he began to hook up the lacy contraption, he heard the giggling of two teenage girls as they entered the dressing area. The sound of their chatter grew closer, and he realized with a sinking feeling that they had picked the cubicle right beside his. His hands paused mid-motion, the bra half-off, as he listened to them gush about their finds, their excited squeals piercing the thin walls of the dressing room cubicles.

He hurriedly pulled his shirt back on, his face flaming red as he tried to calm his racing heart. The last thing he needed was to be caught in this compromising situation. He could just imagine Rachel's reaction, her laughter echoing through the house as she recounted the story to anyone who would listen. The thought of her amusement at his expense was too much to bear. He tried to hide his bras as he stepped out of the cubicle. He dropped them off at the now attended service desk, blushing furiously.

As he left the store, John's eyes darted around searching for the nearest exit. The clerk at the service desk offered a knowing smile, which only served to increase his discomfort. He fast-walked towards the exit and without a backward glance, left the store, the cool air of the mall washing over him like a wave of relief. The bustle of shoppers and the cacophony of sounds provided a welcome distraction from his humiliation.

Taking a deep breath, he steeled himself. He couldn't just give up. Rachel's words echoed in his mind, a siren's call of challenge. He squared his shoulders and started walking towards the opposite end of the mall. Maybe Macy's, with its reputation for professionalism and a wider range of sizes, seemed like a safer bet. His heart pounded in his chest with every step, his thoughts racing. “I think I do need some help,” he thought. “Maybe Macy’s.”

As he approached Macy's, he took in the grandeur of the storefront, the opulent displays of perfume, makeup, and handbags welcoming shoppers into this paradise of luxury. A beacon of hope shimmered in his eyes as he walked toward the escalator to see that “intimate apparel” was on the third floor. When he reached the third floor, he scanned the racks of elegant lingerie, feeling like he had stumbled into a different world, one where he wasn't quite sure of the rules.

John approached the counter where a stylish, middle-aged woman with a knowing smile and a name tag that read "Adele" greeted him. She was tall-ish, with short, straight hair and a figure that suggested she knew the secrets of good undergarments. Her white blouse was just transparent enough to show the lace of her bra. He took a deep breath and decided to ask for help. "Can you help me - I need a bra," he mumbled, trying to sound nonchalant.

Adele's smile faltered for a moment before she schooled her features into a professional mask. She had seen it all in her years of working in lingerie, but a man buying a bra was definitely unusual. She eyed him up and down, her thoughts racing. Was he buying something for a partner? A cross-dresser? A pervert? She cleared her throat, "Ah, yes, can you give me a little more information?" she trailed off, trying not to let her judgment show.

John blushed deeper, feeling the weight of Adele's gaze. He cleared his throat "For me," he said firmly, meeting her eyes. "My wife thinks I need one."

Adele's expression remained skeptical. She had heard every excuse in the book, and she was pretty sure that 'my wife wants me to wear a bra' was a new one. She shifted her weight.

"And what size would you be looking for, sir?" she asked coolly, raising an eyebrow.

John's cheeks burned hotter. He had no idea. He had never had to deal with this before. "I'm not sure," he mumbled. He was sure that every customer and employee in the store was staring at the weirdo trying to buy a bra for himself. "Can you help me?"

Adele's gaze hardened. "I can certainly try sir, but I don’t have any experience fitting men.” She looked around uncomfortably.

“I don't think I can take you into the women's fitting room," she said quietly, her voice low but not exactly apologetic. "But I can measure you, and then you can take the measurements home and order online. It's usually more accurate anyway."

John nodded, his throat tight. He hadn't thought this through. Being measured in the middle of the store was not what he had in mind. “You may be right,” he said, “but I’d really like to bring it home tonight. Is there anything we can do?”

Adele was not comfortable. “I suppose I can try to find you a couple of possibilities and you can try them on in the men’s dressing room.”

"Okay, let's get this over with," John murmured, his voice barely audible.

Adele looked at him calmly. She had seen people in all sorts of uncomfortable situations in her line of work, but John's predicament was unique. She took out the measuring tape with a gentle nod, her movements deliberate and calm, as if to reassure him that this was nothing out of the ordinary. "Don't worry, we're going to find you something that fits perfectly," she said, her voice trying to be soothing.

But as soon as Adele took out her measuring tape, John had second thoughts. He looked around, convinced that the other shoppers were all staring at him (although in reality there were all more concerned with their own shopping experience than his). The whispers and giggles of the teenagers from Target seemed to echo through the mall, and he felt his heart racing again. What if someone he knew saw him? What would they think? He took a step back, his eyes darting around the store as if searching for an escape.

"Are you okay, sir?" Adele asked, her voice a gentle prompt that brought him back to reality.

John swallowed hard, his Adam's apple bobbing in his throat. "I-I think I've changed my mind," he stuttered, taking another step back from the counter. The tape measure was still poised in Adele's hand, a silent witness to his indecision.

Her expression didn't change, but he could see a hint of disappointment in her eyes. "If you're sure," she said, placing the tape back on the counter with a sigh of relief. "But if you ever decide to give it a try, I'm here to help."

John nodded, mumbling a hasty thanks before he turned and practically sprinted out of Macy's. The mall’s air conditioning hit him like a slap in the face, and he realized that he was sweating. He continued walking for a bit to calm down and then sat in a bench near a fountain.

And that's when he saw it. A small, store with a sign that read 'La Jolie Fille’. The window was dressed with the most exquisite set of lingerie he had ever seen. The delicate lace and soft, pastel colors made his heart flutter with a mix of anxiety and excitement. He found himself drawn to it, as if the very essence of the store was whispering sweet nothings of acceptance and understanding into his ear.

Taking a deep breath, John gently pushed open the door. The bell chimed softly, and the scent of high-quality fabrics and faint hints of exotic oils filled the air. It was a stark contrast to the bright lights and cacophony of the mall outside. The walls were lined with rows of dainty lingerie, each piece more alluring than the last. His eyes widened, and his heart raced faster as he stepped into the sanctuary of La Jolie Fille.

The store was smaller and cozier than Macy's, with plush velvet chairs and warm lighting that cast a seductive glow over everything. The merchandise was displayed on tables, with sections dedicated to every style, color, and size imaginable. The sight was welcoming and strangely comforting. Perhaps here, amidst these delicate garments, he could find something that made him feel less like an outcast and more like a man who knew what he wanted.

A young woman with bright blue eyes framed by wire-rimmed glasses looked up from the counter as he entered. Her name tag read 'Kaylie', and she had a youthful smile that seemed to hold a just a hint of mischief. She looked at John with curiosity, not judgment, and he felt his shoulders relax slightly. "Hi there," she greeted, her voice lilting and friendly. "What can I help you with today?"

John took a moment to gather his thoughts before speaking. "I, uh, need a bra," he finally managed to say. The words felt strange on his tongue, but there was something about her demeanor that made it easier to admit his situation.

Kaylie's eyes widened in surprise, but she quickly composed herself. "Okay, no problem," she said, stepping out from behind the counter. "Let's find you something awesome.
“Can you tell me a little more about what you want?”

Her words echoed Adele's from Macy's, but John felt a different vibe here. The small store was intimate, and the way she said it made him feel like he wasn't the first man to walk through these doors in search of a bra. They moved a little further away from the store’s window and closer to a curtained dressing room.

“I’m looking for myself and I’ve never bought a bra before,” John said.

“That is so cool,” she said. “We need to get you something you’ll love.” She opened up the curtain to the dressing room. There were a pair of plush chairs, a couple of full length mirrors, and four dressing cubicles behind thick, velvet curtains.

"So, what's your name?" Kaylie asked, her eyes sparkling with curiosity.

"John," he replied, his voice a little shakier than he would have liked.

"Well, John," Kaylie began, her eyes scanning the selection of bras before her. "My name is Kaylie. Do you have any idea what size you might be or what you might be looking for?"

John felt the weight of the question, his mind racing as he tried to come up with an answer that wouldn't betray his complete lack of knowledge on the subject. "Uh, not really," he admitted, his voice thick with nerves. "I've never had to do this before."

Kaylie nodded understandingly. "That's perfectly okay," she said with a wink. "I'll be your personal bra whisperer tonight." She took his measurements with a gentle touch, her eyes never leaving his in the mirror as she wrapped the tape around his chest and back. The intimacy of the moment washed over him, and he felt a strange mix of excitement and vulnerability. She wrote down the numbers on a small piece of paper and handed it to him. "These are your measurements. You are somewhere around a 38B, 40B or 40A, depending on the bra, but lots of my clients are between sizes. We just need to find something that makes you look good and feel great."

Her words were like a balm to his bruised ego. "Thank you," he murmured, taking the paper from her with trembling fingers.

“Any special type you are looking for?”

“I’d like something nice.” John said, without thinking about it too much. “Not everyday, a little sexy, but not too sexy. I don’t anything, ummm…”

“I understand,” Kaylie smiled. “Sexy but not slutty. Do I have that right?”

“I think so,” John smiled back. “That sounds right.”
“Well make yourself comfortable. There’s some coffee, tea, and water on the table and I’ll be right back with some things to try on.”

Kaylie's eyes twinkled as she returned to the dressing room, her slender fingers caressing the fabrics as she made her selection. "How about we start with something simple, but still sexy?" she suggested, holding up a black bra with delicate lace detailing and a red rose pattern on the cups. "This one is classic, and it'll give you the support you need without being too overwhelming."

John nodded, feeling a flutter in his stomach as she handed it to him. He took it into a cubicle, his palms sweaty. He had never been so nervous to put on a piece of clothing before. He slipped the bra out of its protective tissue, the fabric feeling cool and smooth against his skin as he tried to mimic the way Rachel had put hers on so many times. He couldn’t quite figure out how to do it on himself.

"Do you need any help?" Kaylie's voice was soft, almost a whisper, from outside the changing room.

John's heart skipped a beat, and his hands paused in their fumbling. "Yeah, I think I do," he called back, feeling a strange thrill at the idea of her seeing him in such a vulnerable state.

Kaylie stepped behind the curtain, her movements graceful and unassuming. She took the bra from his trembling hands, and John felt the warmth of her body against his as she approached. Her touch was gentle as she reached around him to grasp the hooks, her breasts brushing lightly against his back. The intimacy of the moment was not lost on him.

She hooked up the back. "Now put your arms through the straps," she instructed, her voice low and soothing. John complied, feeling the smooth satin slide over his skin as he lifted his arms. The cups of the bra rested against his chest, the material whispering sweet promises of support. Kaylie adjusted the straps to provide a little more lift.

"Good," she murmured, her eyes meeting his in the mirror. "Now bend over and reach inside the cup with your hand and scoop your girls into the cup."

John felt his face flush at the casual way she talked about his breasts, but he obeyed, bending at the waist and reaching into the bra. He watched in the mirror as she leaned over, her own breasts swaying slightly in her tight-fitting top. Her movements were graceful and confident, a stark contrast to his own clumsiness.

He did as instructed.

"There you go," she said, her voice gentle as she adjusted the cups. "Now stand up straight and show me what you've got."

When John stood up, the bra feeling surprisingly natural against his skin. The cups fit snugly around his breasts, pushing them up and together in a way that made his nipples tingle. He couldn't help but glance down at his reflection, the sight of his breasts in the mirror making sending waves of excitement through his body..

Kaylie stepped back, her eyes appraising him with a critical eye. "Looks good," she said with a nod. "But let's make sure." She reached around him again, her hand brushing against his side as she adjusted the straps again. The bra tightened, and John gasped as his breasts were lifted even higher. The sensation was incredible, the fabric hugging his skin in a way that was both confining and liberating.

"Perfect," she proclaimed.

John's eyes widened in the mirror. The cups held his breasts in a way that was both comfortable and surprisingly erotic. He had never felt so... feminine before, and the sensation was intoxicating.

"Kaylie?" The voice from outside the curtain was deeper, more authoritative. It was Beverly, the store manager, a sweet, older woman with a warm smile. John’s heart skipped a beat, his hand flying to his chest as if to protect his newfound secret.

"I'm with a customer," Kaylie replied, not missing a beat. She stepped back and gave John a knowing look in the mirror. "Be with you in a second, Bev."

John's heart pounded as he realized Beverly may have seen him in the mirror. He was about to apologize, to explain, to do anything to get out of this situation, when he heard a second set of footsteps approaching the curtain. Beverly's warm, motherly voice was unmistakable. "Is everything OK in here, sweetie?" she asked brightly.

Kaylie stepped aside, and Beverly's eyes took in the sight of John in the bra. She paused for a moment, her smile never wavering. "Oh my," she said with a gentle laugh, "I see Kaylie found you something that suits you quite well."

John felt his face turn scarlet, but he couldn't bring himself to look away from the mirror. The way the bra framed his chest, lifting his breasts and pushing them together, was surprisingly appealing and in a strange way, he was starting to feel eager to show off.

"We have some beautiful matching panties," Beverly suggested, her eyes twinkling with mischief. "They'll complete the look, and I promise you, your wife will absolutely love it."

John felt a surge of excitement at the thought of Rachel's reaction. He had come into the store with a sense of dread and embarrassment, but now, with the encouragement of the two women, he felt a strange sense of liberation. He nodded eagerly. "Yes, I'd like to see them."

Kaylie's eyes sparkled as she stepped out of the changing room, leaving John to finish adjusting the bra. "I knew it!" she exclaimed, her voice carrying a hint of victory. "Beverly, John's a perfect fit for a 40B. Can you grab a couple of pairs of matching panties so we can check the size?"

Beverly nodded, a knowing smile playing on her lips. "I'll be right back," she said, disappearing into salesfloor.

John took a deep breath, trying to calm his racing heart. He couldn't believe he was actually considering buying a bra and matching panties. The thought of Rachel seeing him in them sent a thrill through his body, and he found himself excited at the thought of seeing her reaction.

When Beverly returned with the delicate, lacy panties, John felt his cheeks heat up even more. He had never seen anything so intimate and beautiful.

"Let's see," Beverly said, her eyes scanning the options. "I think these will look lovely on you." She held up a pair that matched the black satin bra perfectly. The black satin material was almost adorned with roses, with tiny bows adorning the edges.

Kaylie took the panties from Beverly and handed them to John with a wink. "Why don't you try these on?" she suggested. “These look like the right size."

“Okay, I’ll try them on," he murmured, his voice thick with nerves.

Kaylie and Bev left John by himself in the dressing cubicle. He took off his shoes and socks and was beginning to take off his pants, when he heard Bev say "I'm sorry, doll but we have to think of hygiene. We usually ask our ladies to try panties on OVER their underwear, just to make sure everything is safe for all our customers. You understand, don’t you hon?

"But you can't put these panties on over your boxers, now, can you?" Beverly said, her voice a gentle reminder of the reality of the situation.

“But I can put a panti-liner on these panties for you so you can try them on. They aren’t terribly sexy but we do have to be careful.” She reached through the curtain to give John the panties.

John's cheeks burned as he took the panties from Bev through the curtain and stared at the panti-liner now attached to the delicate black panties. He took a deep breath and stepped out of his jeans and boxer, then stepped into the panties. He felt like he was in a trance as he slid the silky material up his legs, feeling the coolness of the air kiss his skin.

The panties slid into place, the panti-liner providing a surprisingly snug fit against his now bare skin. He looked up at the mirror gently nodded approvingly. The lace hugged his new curves in a way that was both thrilling and terrifying. Rachel's words echoed in his mind, and he could almost feel her eyes on him, her smile a mix of amusement and arousal.

"How do they feel?" Beverly asked, her voice kind.

Kaylie asked “can we see?”

John felt his cheeks redden even further. "They feel... good," he managed to say, his voice a little too high. He stepped out, carefully pulling the curtain closed behind him so nobody saw his men’s clothes in a heap on the floor. Curiously, he was more embarrassed by his jeans, boxers, and dirty socks than he was standing in front of Kaylie and Beverly in a bra and panties.

Beverly stepped closer, her eyes scanning him from top to bottom. "Turn around for us, darling," she instructed, her voice gentle but firm. "We need to make sure the fit is just right."

John complied, feeling the panties hug his ass as he slowly spun around. Looking at the mirror, he was grateful for both his newfound svelte waist and his soft and sexy manboobs.

Beverly nodded approvingly, a hint of a smile playing on her lips. "They look absolutely divine on you," she said. Absolutely lovely.

In the meantime, Kaylie had brought in a few more sets from the sales floor. She asked John if he wanted to try anything else. The three of them pawed through the different sets until Kaylie said “You know what? I don’t think anything beats that first outfit – the black and rose one. I’d go with that.”

“I think so too,” John added.

Beverly nodded in approval. “So let’s do it. Let’s get going and ring these up.

"Do you want to wear them home?" Kaylie asked but John didn’t answer right away. The idea of leaving the store wearing a bra and panties, whether they could be seen under his clothes or not, both thrilling and terrifying. He had never felt so exposed or as excited.

"I... I think I'd like that," he stammered, his voice barely a whisper. Then he giggled. “I think I will.”

Kaylie's eyes sparkled with excitement. "Good choice," she said, her voice a soft purr. "They're going to make you feel so beautiful."

"Alright," Beverly said with a knowing smile. "Let's make sure everything looks perfect before you go." She stepped closer, her eyes scanning John's body. "Kaylie, can you get some scissors to snip off all the tags?"

Kaylie nodded and disappeared behind the curtain, returning with a small pair of scissors. Beverly carefully snipped away the tags from the bra and panties.

John got dressed in the rest of his clothes while Bev and Kaylie rang up the sale. When everything was taken care of, Kaylie pecked him on the cheek.

"Thank you," he murmured, his voice thick with emotion. He couldn't believe the journey he had just been on, from the embarrassment of admitting his need for a bra to the exhilaration of purchasing lingerie that made him feel desirable.

When he got to his car, he was still breathing heavily, his mind racing with the memories of the past hour. He ran his hands over his bra-covered breasts. The thought of Rachel seeing him in the bra and panties made his stomach flutter with a mix of anxiety and excitement. The ride home was just a blur.

Walking into the house, John could feel Rachel's eyes on him before she even said a word. She was sitting on the couch, flipping through a magazine, but the moment he walked in, she looked up. "Well, what did you get?" she asked, her tone light and teasing.

John felt a rush of nerves. "I got what I needed," he said, trying to sound nonchalant. She raised an eyebrow when she saw the La Jolie Fille bag (which now contained a rumpled pair of boxers) and smiled as John walked through the room towards the master bathroom.

He slipped out of his clothes, washed his face, and combed his hair. He removed the panti-liner, tossing it away. He soundlessly walked downstairs to the kitchen where he poured a couple of glasses of wine before sliding into the doorway of the living room.

“Well,” he said. “What do you think? Did I do OK?”

Rachel was struck dumb for a moment. There he was in a beautiful black and rose bra with breasts almost filled his cups, highlighted by his pert nipples pointing right at her. Beautiful! And she wasn’t expecting the panties. His butt was so cute in those panties she was almost jealous.

That silent moment was only a moment, though. “OK? Oh My God you are fabulous.” She sprung off the couch towards her smiling husband, who barely had time to place down the wineglasses before she hugged him madly.

Needless to say, they had a very exciting night that night. Before dawn, they both agreed that they had to visit La Jolie Fille together.

INTRODUCTION
My great idea was born on a lazy Sunday night when my husband and I were curled up on the couch watching a rerun of Law and Order: Special Victims Unit. It was one of the early episodes, before Olivia became a star and she still looked like a real dyke. My husband, Jack, was clearly lusting after her. This wasn’t a real surprise, because he often gets the hots for women on TV and I make no apologies for fantasizing about any number of guys on my living room screen. What struck me, though, was how many of the women Jack seemed to like were, well, butch.

So I decided to play with him a little bit, stroking his hair, caressing his chest, tweaking his nipples — nothing below the waist. He starts squirming so I get a little bolder, nibbling his ear, running my fingers along his thigh. It didn’t take long before he began to respond and pretty soon we’re upstairs, forgetting all about Olivia and whatever case she was working. I made sure I took the lead, only this time did a couple of things he wasn’t expecting, like pushing him down on the bed and covering his mouth with my pussy, or lying on top of him and spending several minutes sucking and kissing his nipples.

Pretty soon, I was on top with him inside me, but he was moaning “fuck me, fuck me,” so I did. I rode him hard until I came -- hard. And when I did, I quivered like crazy which made him explode in me. We just lie there together for a few minutes, until his cum dribbled out of me all over his cock and hair. I grabbed my panties from the bed and tossed them at his face, telling him laughingly to clean up.

Now every once in a while we had done a little crossdressing to spice things up. After all, Jack looked really cute in my panties, even if they were a size too small and you should see him in my pale green baby doll nightie! But what happened next was pretty different. This was the last day of my period and the pantiliner in the panties had a little staining. When Jack began to clean himself up, he got hard as a rock almost right away. It was amazing! We went at it all over again right away, but I couldn’t let all this slip away. Someday, somehow, this was going to be useful.

THE FOUNDATION
Jack’s birthday is in early December. After a Labor Day weekend that involved way too much barbecue and way too much beer for the both of us, I suggested that we both needed to go on a diet. Jack agreed, but didn’t seem all that enthusiastic. I upped the stakes a little by making it into a contest. Whoever won, or lost the most weight between now and December 1, would be entitled to a no holds barred shopping spree at Macy’s. Whoever lost, would have to wear an item of apparel chosen by the winner, no questions asked.

It was soon clear, however, that Jack wasn’t taking this at all seriously. I managed to peel off a good ten pounds by Thanksgiving and if Jack was weighing himself, he was doing it when I wasn’t around and there didn’t seem to be a whole lot of changing to his waistline. On December 1, we had our weigh-in and, as I expected I would, I won. I just smiled and waved my Macy’s credit card. He then asked my timidly what his penalty was going to be.

“I’ve given this a great deal of thought,” I said smugly. “I think since you’ve turned into such a little tubby, that you really need a girdle, and I’ll really need to help you pick it out.” You should have seen the expression on his face. He wasn’t really all that tubby. He’s about five-ten and fairly well built, but he has been adding a little more around his middle than he should have. But when he learned he’d have to wear a girdle to settle his bet — that was priceless.

So that Saturday was his birthday rolled around, I suggested (without mentioning his birthday) that we go out for the day. I told him we were going to do a little shopping and have a nice lunch, and that may have gotten him to thinking that a birthday surprise of some sort was in order. Neither of us was wearing anything fancy — I had a denim skirt that may have been a bit shorter than usual, tights, a sweater and flats. He wore his navy blue sweater with silver horizontal stripes and light colored chinos. Perfect.

We drove into town and parked. When I said shopping earlier, I know he probably thought mall but the town shopping center was better for what I had in mind. After leaving the car, I led the way down the street to the non-descript storefront of Celeste’s Foundations. It was an old-fashioned bra and girdle shop, the kind that they usually don’t have anymore, but Celeste’s had been doing business here for a couple of generations and was still live and kicking. The window was full of bras, girdles, nightgowns and swimsuits on dusty mannequins, signs from breast form and bridal wear manufacturers.

I saw Jack’s face reflected in the window. He was a mixture of confusion and fear. I leaned over in his year and whispered, “Your first birthday present is the girdle I promised. There will be more later.”

There weren’t any other customers in the shop just then and a girl in her 20s looked up and asked if we needed some help. She was dressed similar to me, except that her skirt was much shorter, her sweater much tighter and I didn’t have a streak of lime green in my hair or a stud in my nose.

I stepped to the counter and said “Yes, please. My husband Jack, here, is a crossdresser and I want to show Jackie that getting dressed up involves more than putting on pretty panties. I think I want to teach him a little lesson, you see.”

Well Jack was about to die. I’m sure he thought that I’d buy the girdle, he’d slink around in the background and that we’d leave. I, on the other hand, wanted to have some fun.

“So,” I continued, “at the minimum we’re looking for a really firm girdle and we’ll see what happens from there.”

The salesgirl smiled. “No problem,” she said. “My mom, who runs this place, is out on some errands but she’ll be back soon. In the meantime, I can get us started. Do you have any specific idea of what you want?”

“Jack, honey,” I said sweetly, “what did you want?”

He blushed furiously and mumbled “a girdle.”

“There’s lots of different kinds,” the salesgirl smiled. “I’ll give you some options to think about.” She scurried about behind the counter and pulled out four different panty girdles in different designs and colors and laid them across the counter. “Something like this?” she asked me.

I turned to Jack. “Jack, which one would you like?” He picked a fairly plain white one, just like I knew he would.

“Do you know your size?”

“Miss, I think you need to measure him, don’t you?” I suggested.

“No problem. By the way, my name is Addie.” She walked out from behind the counter with a cloth tape measure and measured my Jack.

“There’s always a question with men because they’re built differently. If we use the waist measurement, he’s a 2XL. If we use the hip measurement, he’s a large.”

“Hmmm.” I looked puzzled. “Jack, why don’t you try on a large?” The look he gave me could have drilled a hole through concrete. “Addie, it’s OK to try them on, right?”

“No problem. Just keep your underwear on.” She led Jack to a dressing room at the back. They had a row of four of them, all with swinging doors that were open at the top and bottom. She opened the door of the one closest to the counter and ushered him inside with the girdle. “Let me know if you need any help.”

I watched through the bottom of the swinging door as Jack took off his shoes, dropped his pants and pulled on his girdle. When I was sure it was on, I went over to the dressing room. “Honey, let me see,” I said as I opened the door. I was sure that Addie could see as well. “Well this is a real problem, isn’t it?”

Jack had worn boxers, which were all bunched up and poking through the leg holes. “This won’t do at all. Addie, can you get him a pair of panties? Put them on the bill.”

She returned with a sampling of panties of various cuts and styles, all pretty. “No, I think something plainer is called for. Just something ordinary.” She returned with a pair that was white, undecorated and 100% polyester. “These will be fine” I said as I handed them to Jack. “Put these on underneath honey.”

He did as he was told and I gave him a minute to two for the girdle and then opened the door again. “This still doesn’t look right. Addie, can you come here a minute? What do you think?” I looked at Jack. “Hold up your shirt, honey, I can’t see the waistline.”

I turned my attention to Addie for a minute. “He’s still got a little paunch right here,” and I rubbed my hand against Jack’s tummy. “And there’s something else that isn’t quite right.”

Addie turned to me and said what I thought was “muffin top.” I looked at her quizzically. “Muffin top,” she repeated, pointing the roll of flab that poked over the waistband. She was right; it did look just like the top of a muffin.

“I think maybe we need something firmer and high-waisted” and she went to fetch what she needed. When she returned, I knew we were beginning to get serious. This girdle had satin panels and all kinds of bars and stays and things all over it, with a large band at the waist. It was also decorated with a tiny, cute satin bow and a floral pattern in the spandex. “Try this sir,” and she handed it to Jack.

He scowled at me but not wanting to make a scene, did what he was told. He pulled to door closed but I could hear him struggling with it a little more. When Addie asked him how he was doing, we heard a gruff “OK.”

I opened the door, turned to Addie and said, “this is an improvement, but it still isn’t right. The tummy is better and the, umm, muffin top is much smaller but it’s still there a little and this is a problem.” I pointed to the crotch where Jack’s pantied “equipment” was spilling out the sides.

I could tell that Addie was really enjoying this by now. “I can see that. This is more complicated than I thought.” She paused for a minute. “This is going to take a little work. I hope you have some time” and she beamed at both me and Jack.

We tried all kinds of things to get that perfect look. We tried a different high-waisted panty girdle with a wider crotch panel, but it didn’t really solve the problem. An open bottom girdle solved that issue, but required stockings to hold it in place and I just didn’t see Jack being very good at attaching stockings to garters. Besides, the open bottom girdle flattened his tush a little more than I wanted. From there, we went to a long-legged girdle which solved the equipment leakage problem but brought the muffin top back.

Every so often a customer would come in the store and Addie would have to leave us. I’d from Jack, leaving him in the dressing room in whatever girdle he’d last tried on. If the opportunity presented itself, I’d try to say something or even open the door so the customer would see or hear him. He was sulking and clearly totally embarrassed, but wasn’t resisting.

I don’t remember why we didn’t like the long-legged girdle with a waist-nipper but we didn’t. Addie had gone to get an all-in-one, when her mom, Celeste, came back in the shop. There were a couple of other customers in the shop at the time. “Good to see you Mom, we’ve been busy this morning. This,” and she held up the all-in-one, “is for the guy in the dressing room. He’s a crossdresser and he and his wife came in this morning to get some help in the shape department.” The other customers looked at the dressing room with amused curiosity.

“That probably won’t fit, Addie,” Celeste said without batting an eye. “He’s probably too tall.” She took the all-in-one from Addie, opened the door and held it against Jack’s mortified body. “We’d never get this to fit.”

“I know what will work, though. Why don’t you help these other ladies and I’ll step in here.” She turned to Jack and introduced herself. “You’re going to need a high-waisted, long legged girdle. How firm do you want to get?” she asked him. I spoke up. “Nice to meet you Celeste. I’m his wife. I think we want something really firm. I want to make sure we control this tummy and maybe give him a little bit of a waist.”

“I’m sure we can help.” When she came out from the back room, she had a long white box and she showed me the contents. It was exactly what she said, a high waisted, long legged panty girdle with lace on the leg cuffs, a stiff front satin panel, tiny bow at the top of the panel and lacy pattern in the material. It also had a series of hook and eyes running up the side covered with a zipper. It was really pretty, but also looked as if it could have been used by the Spanish Inquisition.

“Why don’t you get into this and then I’ll help you hook it up.” She gave him a moment of privacy to take off the old girdle and pull this one up before opening the door to close him up. I couldn’t really see what was going on, but I did hear both Celeste and Jack huffing and puffing every so often. When she was finished, she stepped away from Jack to show me results.

This was great. The high waist extended up to his rib cage and really did pull in his waist. He looked positively darling in the lace and the satin, but there wasn’t a millimeter of jiggle under that monster.

“Celeste, you are a miracle worker. This is almost perfect.” She looked at me inquisitively. “Well, we have a little bit hanging over here,” and I pinched a bit of skin that was pushed over the top of the girdle. “I also wonder if you have anything that would give him a little shape back here,” and I rubbed my hand over his bum.

Celeste answered, “There are only a couple of things that will smooth all over, and we already know he won’t fit into an all-in-one. You could try a corsolette, but then you’d need stockings and a corsolette won’t work with pants. The only other thing I know is a long-line bra.”

“I hadn’t thought of a bra,” I said, “But I’m not against it. Why don’t you measure him.”

Now I could tell by Jack’s reaction that his initial shock had worn off, replaced by some confusion and lots of humiliation — and by the blush that was creeping into his cheeks, I could tell there was some excitement, too. When Celeste took out her tape measure, he lifted his arms without being asked.

“He’s a 42 for band size.” She announced when done. “What about...” and she brushed his breasts.

“Let’s worry about that later,” I said. “Let’s just see how it looks.”

Celeste went off to the stock room and returned with a couple of boxes. “The only long-lines we have in that size have large cups. These are both D’s. One hooks up the back and one is front-close. The one that hooks up the back is prettier, I think.”

She took the bra out of the box, adjusted the straps and turned Jack around. She put his arms through the straps, put the cups in the right
place, pulled tight on the elastic, hooked him up and turned him around.

The effect was stunning. The lace pattern on the bra almost matched the lace on the girdle. The strong, wide waist band of the girdle was reinforced by the bra so that Jack’s waist was reduced by almost 2”. “That’s really nice, Celeste, thank you.” I said. “Thank the nice lady, Jack.”

He mumbled a thank you.

“The problem areas have shifted, though," I said, noting the empty sagging bra cups. Also, now that Jack had a little bit of a waist, his lack of hips and bum was becoming more noticeable.

Addie, who had been helping other customers for the last several minutes, gave her mother two boxes and said "it seems to me that you could either wait for him to grow into them or try these." The boxes contained breast forms that the shop carries for mastectomy patients. "These are D's to match the size of the bra."

Her mother took the forms out of the boxes and placed them in Jack’s bra, being very careful to adjust them just so. When she was done, she stepped back and looked, like an artist looking at almost finished canvas. “What do you think,” she asked me?

This was getting amazing. From the neck down, there was almost no hint of maleness in Jack. There were wisps of leg and arm hair and a narrow butt, but his large boobs and slimmed waist more than made up for those minor flaws. “Celeste,” I said, “this is really great. You’ve done a wonderful job. You too, Addie.”

"I think so too,” Celeste smiled. “I just thought of one more thing to make him perfect.” She turned to her daughter. “Addie, will you get the padded panty-girdle by Venus? Bring out a large and a medium.”

While Addie was gone, Celeste and I made small talk in front of the open door of the dressing room while Jack tried to make himself as inconspicuous as possible. He wasn’t being very successful, but I could also tell that he was getting seriously turned on by all of this. Addie returned and gave Celeste the boxes. The girdle was an ordinary white panty girdle but it had pads built into the hips and butt. “Since he’s already wearing a firm girdle, a large might be too big. I’d like him to try the medium first.”

She handed Jack the girdle. When he reopened the door, my jaw dropped. It wasn’t nearly as pretty as what he had before, but he must have added 6” to his hips. “That’s IT!” I squeaked, clapping my hands. “That’s exactly the look I wanted. Jack, put your clothes on, I’d love to see how this changes you dressed. Celeste, do you want to start writing up the bill? This is so great.”

Celeste moved towards the cash register to write up the sale. Jack hissed at me. “I can’t go out looking like this!”

“Don’t be ridiculous, you won’t be going out looking like that. You’ll have your sweater and pants on, silly. And your jacket.” I smiled sweetly. “Besides, I have your wallet and keys.” I waved the items I’d swiped while he was in the changing room. With that, I flounced off towards Celeste to pay the bill.

When Jack opened the dressing room door again, his size D boobs severely tested the stretch properties of his sweater while hugging his new waist. He clearly had some trouble zipping his pants, as these men’s khakis were not meant for hips this big. There were clear stretch marks across his now totally flat tummy and not a single bump or bulge where most men have them, if you know what I mean.

Did he look like a runway model — no way, but he didn’t look like a guy either. “Jack, sweetie” I said, “put on your baseball cap. I want to see something.” When he did, I saw what I wanted. His longish, if thinning hair, fell below the cap, which hid the thin spots on top. Standing in front of me was a frumpy, awkward, gawky woman. The beginning of Jack’s fantasy dyke, if you will.

When we stepped out onto the street, Jack tugged his jacket across his boobs and kept his arms tight across his chest. He kept his eyes focused tightly on the ground, so as not to make any eye contact with anyone.

“If you are trying to attract attention,” I said to him, “the best way to do it is to look like someone about to commit a robbery, which is exactly what you are doing. Just be yourself, sweetie.” We walked a couple of blocks and then I took a sudden turn into the Ann Taylor store. Jack quickly followed, petrified about being out on the street with D boobs, without me to protect him.

I told Jack I’d only be a couple of minutes but that I needed a couple of things. I took my time browsing through the racks of clothes for the office, and then took a look at a couple of sales racks. What I was looking for was something for Jack, to spice up his look a little without freaking him out too much. His sweater wasn’t too bad, but those pants were pretty hideous and he could use a little color.

Without taking too long, I picked up a pair of pants on sale. Since they were women’s and had a stretchier fabric, they would accentuate his new hips and butt better than his ugly, lumpy cargo pants. The waist would be lower, but most important, they would be flat in the front, hugging his now smooth crotch. These particular pants were charcoal with a light pinstripe and would work just fine with his sweater. I added a paisley scarf while checking out.

Jack was too concerned about whether anyone noticed him to see what I was doing. That was just OK with me. The cashier rang up the sale, put the pants and the scarf in a bag, and off we went. As we exited the store, I hooked my arm in his, swinging the bag from Ann Taylor, as if prancing in a TV commercial.

We turned right out of the store and headed towards the main intersection of the downtown section. After dawdling in front of a couple of storefronts, I jerked him into a Starbucks and sat him down with my Ann Taylor bag at a table that wasn’t too far from the restrooms. Once he was settled, with his arms firmly crossed across his chest so (he thought) nobody would see his boobs, I went and got us some lattes.

I put the lattes on the table and we started to sip our drinks. We chatted about nothing in particular, but I could tell he was not only nervous as hell but more than a little turned on. He kept fidgeting in his seat and he was having difficulty following what I was talking about. After a couple of minutes, I excused myself to go to the ladies room. After having a pee, I also changed my maxipad (it being that time of the month). I really didn’t need to yet, but I had another wicked thought. I carefully wrapped it up in toilet paper and placed it in the little receptacle next to the toilet paper dispenser.

When I came back to our table, I “accidentally” knocked my latte into Jack’s lap. Well, not into his lap, but all over his legs. He jumped up, forgetting to hide his boobs which were now jiggling all over the place. His pants were soaked with hot latte and I could see him getting angry and out of control.

“Jack honey, don’t get upset.” I said, being the concerned wife. “You can put these on,” and I waved the Ann Taylor bag at him. I saw him scowl and I pulled out the pants. “Look — grey pants — nothing you haven’t worn before and nothing that anyone will notice.” He scowled again.
“Seriously. Tell me what you see”

He waited for a couple of moments, and then said “Grey pants.” He grabbed them and then hesitated.

I knew he wouldn’t know that women’s pants are cut differently and that the way these would hug his butt and his bulge-less crotch would make all the difference in the world. He was sort of clueless in the realm of fashion. But when he hesitated, I also knew he was a bit confused as to what he was supposed to do.

“Umm, I don’t think you should use the men’s room looking like that. Let me check the ladies and make sure the coast is clear.” I knew there was nobody in there but I wanted to stretch this out a bit. I opened the door and made a show of looking around. Of course there was nobody there but I looked relieved. “Everything’s OK sweetie.”

Just before he entered, I leaned into his ear. “By the way, dear, I just changed my maxipad. If you want, it’s the top one in the little metal box next to the toilet paper. Just press it into your panties. You might like the way it feels.”

He seemed to be in the ladies room for a while, which made me smile. If all he was doing was changing his pants, that wouldn’t have taken very long. Pulling down the padded panty, the girdle, and the panties, and then arranging the maxipad would have taken a bit of time. When he finally emerged, he was a even a little more flushed than when he went in. He sat down and then fidgeted for a bit, which made me believe that he used my pad.

“Ummm, did you?” I asked quietly, while looking away. When I turned towards him, it was obvious that he had. I stayed quiet, though, until he nodded.

“Yes.”

“Well let’s get going then,” I brightly announced. We had one more stop in my plans.

We started walking back towards the car, but as we passed the MAC cosmetics store, I dipped into the store, carrying Jack with me. As soon as we entered the store, one of the black-clad aestheticians, armed with an apron full of brushes and pencils, brightly asked if she could help me.

“Not me,” I replied. “My husband,” and I gestured towards Jack, my husband, with size D boobs, a padded butt sticking out to there and wearing pants that clung to his every curve.

“No problem,” she said. “I’m Tonya. What can I do for you,” she beamed at him.

I jumped in. “We’re big fans of ‘What Not to Wear’ and shows like that and we noticed how much difference makeup can really make. So Jacki has been dabbling a bit in girls clothes, and we wanted to see what a little makeup can do.”

“You’re so right, makeup makes so much difference. What kind of look are you looking for?” Tonya wasn’t sure who she should be talking to because Jack was acting a little comatose. She kept switching back and forth between me and him and he was doing everything he could to look invisible

“Jacki sweetie, “ I said, “do you have anything special in mind?”

“Not really, “ he mumbled.

Now I wanted to lay down my big card. “I think something along the lines of a big ol’ bull dyke who has the hots for a cutie and is planning her first date. What do you think?” Now I have no idea what Tonya thought, but I know that Jack pretty much melted into the ground through a combination of embarrassment and lust. Actually, I don’t know how I got through that line myself.

Tonya, on the other hand, seemed to take it all in stride. “I have some ideas,” she said. “First, why don’t you sit down right here and let me get some stuff.” She parked Jack in a tall stool by a mirror and started collecting materials. When she got back, she began by cleaning his face a bit, and then applying a concealer to a couple of problem spots and a foundation to even out the skin tone.

“Now,” she said, “if you’re a dyke you probably aren’t all that used to makeup so you’re probably going to want to go a little further than straight girl would. Is that OK?”

I said yes, before Jack could even think of a response.

With that, she got started. First, she plucked a bunch of eyebrow hairs and then put on a sealer to define what was left. Next, a thick black eyeliner on the top lid and a slightly thinner line on about half of the bottom lids. A smoky grey eyeshadow on the bottom lid with a slightly lighter shade of grey on the upper lid. The blush was a darkish red, darker and more apparent than anything I’ve ever worn but curiously not all that out of place on Jack’s skin tone. This girl knew what she was doing.

Finally, the lipstick, a dark red, almost burgundy, in a thick application. For the clothes Jack was wearing, this was obviously too much, but if Jack were to change into a business suit or a cocktail dress, he would have been positively hot. We wound up buying the foundation, concealer, lipstick and eyeliner, passing on the blush and eyeshadow. When Jack realized that we weren’t going to wash his face before we left the shop, I could see the panic flashing under the artificial color but we were far beyond that.

As we walked back into the sunlight, I have no idea was was going through his mind. But I know what I saw. I saw a tall, gawky, lesbian with too much makeup, a big shapely butt and big, saggy boobs. I also saw the love of my life, looking incredibly nervous and even more incredibly turned on.

I slid up next to him and then pulled his body close to mine. His boobs and mine kind of mashed together. I slid my hand down to his crotch, feeling the maxipad, then rubbing it a couple of times causing him to shiver. Then I slid my hands around to his butt, pulling him even closer to me.

Right out there on the sidewalk, with dozens of folks walking by, I kissed him hard and deep on the mouth, our tits, tummies and “down there” bits all crushing up against each other. Within seconds, I felt him cum, hard, violently, shaking against me. I held him tight until he was done.

“Aren’t you glad you’ve got a maxi,” I grinned. “I’d hate it when I get my panties dirty.”

I could taste his lipstick on my lips.

“Let’s go home,” I said. As we headed back to the parking lot, Jack was walking kind of funny. I couldn’t tell if it was because he was weak from his orgasm, or he was having problems with the cum in his Kotex.

I can pinpoint the day this all started. It was a chilly, Sunday afternoon in early December. A light rain was falling outside and Carol (my wife) and I had built a cozy fire in the fireplace. She was sitting on one of the couch, her legs curled up beneath her reading and sipping a glass of wine and I was sitting at the other watching the Giants begin to give away a 21 point lead to the Eagles.

Carol stood up and stretched, heading toward the kitchen.

"Get me a beer, hon'" I called after her.

"What's the magic word?," she asked with a twinkle.

I just wasn't in the mood for this. I'd had a bad week at work, the weather was making me miserable and the Giants weren't helping. "Just get the beer, alright? I don't feel like playing games."

She brought the beer and gave it to me without saying a word. When I opened it, it exploded all over me. "What the big idea?"

She giggled to herself, "You really should have asked me more politely. I'm not your maid, you know, I'm your wife."

"Yeah, well right about now I think I'd rather have a maid. At least a maid wouldn't go shaking up my beer."

She turned to me. "You're serious, aren't you?"

I didn't replay, but just stared at the tube.

"Look at me when I'm talking to you." I dismissed her pique with a wave.

"OK, have it your way. I have a wager for you. Interested?"

I was, and turned around to face her. "Go ahead. What are you suggesting?"

"You want a maid so much, here's your chance. If the Giants win today, next week I'll be your maid for the game. I'll get a sexy little maid's outfit and I'll serve your every need all through the game, and who knows, maybe after. How's that sound?"

It sounded great. Carol is a beautiful woman and the thought of her in a tight, short maid's outfit was something I'd fantasized about many, many times. On the other hand, it sounded a little bit too good to be true.

"And if they lose?"

"Nothing too drastic. Instead of me reading and you watching the game, we'll rent a long, romantic movie and watch it together while we talk like a couple of long, lost girlfriends." Her eyes twinkled.

That didn't sound too bad. The Giants were playing the Lions next week and that didn't exactly come off as the game of the century. "That's it?" I asked.

"That's it. You just have to dress the part."

"Dress the part?"

"Yes, dear, are you having trouble hearing?," she asked. "My girlfriends don't wear jeans and flannel shirts when visiting." She smiled a great, big smile.

"You want me to wear a dress?"

"A dress, or a nice skirt, or whatever you please. Just no pants."

I thought about this for a minute. The Giants were leading by 21 late in the third quarter. The upside was having an amazing fantasy come true. The downside seemed a little silly, but how bad could it be? If this was a bad bet, I couldn't see it.

"Honey, you got yourself a bet."

Carol leaned over and pecked me on the cheek. "That's nice dear," she smiled. "Let me know how the game comes out." With that, she got up off the couch and headed for the kitchen to begin dinner.

I returned to the game and was a little surprised to see that the Giants lead was down to 14 points during the commercial break between the third and fourth quarters. About four minutes into the quarter, the Eagles returned an interception 63 yards for a touchdown to bring the score to 28-21. On the kickoff, the Giants fumbled and the Eagles recovered. Two plays later it was tied at 28. After the two teams traded unsuccessful drives, the Eagles drove the ball to the Giants 20 where they scored a field goal with less than two minutes left to give them a 31-28 lead. The Giants did nothing in the remaining 90 seconds, giving the Eagles the win.

I sat there stunned. Carol won. No maid. No football next week. And I had to wear a dress. When the news came on after the game, Carol poked her head in the living room. "How did the game end, honey?"

"The Eagles won."

"That's wonderful, honey, we're going to have such fun next week." She was grinning from ear to ear.

"You're serious, aren't you?"

"Absolutely, dear, absolutely. You would have been if you won."

"I guess. Where am I going to get a dress?"

"You know, sweetie, I think that's your problem." I could swear she was smirking as she returned to the kitchen.

**************

I couldn't imagine how I was going to get a dress and thought about little else for the next couple of days. I finally got up my nerve to go to the shopping mall on Wednesday evening, but when I saw one of the neighbors in the atrium I got scared and left. When I got home, Carol noticed that I was a little late. "Doing some shopping dear?," she asked innocently.

I said nothing and ate my dinner in silence.

A couple of times during the week Carol mentioned how much she was looking forward to this Sunday and asked what movie I wanted to see. I just grumped about and refused to get pulled in, and I think that made her even happier.

It was on Saturday that I finally got up the nerve to get my dress, because by then I thought up a plan. I drove out to the mega-discount store a couple of towns over, where no one was likely to recognize me. Once there, I got a shopping cart and picked up some duct tape, some athletic socks, a couple of big bags of potato chips, some windshield washer fluid and one of those big ugly flowery housedresses that zip up the front, the kind my grandmother used to wear all the time. I could play this thing for laughs, couldn't I?

I had to push that damn cart around the store a half-dozen times before I found them, but I did. I picked out the biggest one I could find after I realized I had no idea about sizes, so I got the biggest they had, which was a 28 and quickly jammed it into the cart. When I got to the checkout, the girl rang up the housedress just like everything else, no bells and alarms went off, and she bagged my purchases and I drove home.

******************

On game day, I got dressed as usual, had breakfast, ran a couple of errands and generally puttered around the house. Carol did the same thing, but there was a real bounce in her steps, where I was dragging. She kept looking at me and smiling and it was getting on my nerves.

About ten minutes before kickoff, she asked "Aren't you forgetting something, dear?"

I grumbled and shuffled off to the bedroom where I got the housedress out of my closet. I stripped off the jeans and flannel shirt and put this monstrosity on over my T-shirt and boxers. Zipped that sucker up and then put on a pair of white sweat socks. I glanced in the mirror and from chest level down, I could have been my grandmother.

"Ta Da!" I shouted as leapt into the living room.

Carol just stared at me. "You're kidding."

"Uh, no. You wanted me in a dress. I'm in a dress."

"You missed the whole point," she said quietly. "I wanted a quiet, intimate, warm, lovely, romantic day and you turned this into a joke. A stupid pointless idiotic joke."

Now it was my turn to stare. "But..."

"I thought the clothes thing might be a little fun. Might shake you up a bit and suggest some stuff for later, but...I can't believe you did this. You are such a selfish prick. Take that ridiculous thing off."

I did as she asked. I really didn't know what to say to do, so I just stood there while Carol stared at the fireplace. She abruptly got up and stalked off. About ten minutes later I heard her start the car and drive off. I got dressed again and turned on the game, but my heart wasn't in it. When she came back an hour later, she glanced at me on the couch, beer in hand, Giants on the tube, snorted and walked straight upstairs.

For the rest of the day we didn't speak and sleeping next to her was like sleeping next to an igloo. Our conversation for the next couple of days consisted of "Pass the salt," "Have you seen the paper?" and "Can't you even pick up after yourself?" accompanied by a pair of dirty socks hurled in my direction.

I was in trouble.

*******************

I was in trouble and the only thing I could think of to get me out of it was to turn the clock back a week. Some things were easy. I picked up Dr. Zhivago at Blockbusters, some cheese and crackers at the supermarket, a nice Chardonnay and an expensive champagne at the liquor store and a bundle of wood at the hardware.

Now came the hard part.

***************

I thought that getting the dress would be the right place to start, but I came up against that size thing again. I couldn't just walk into a store and grab something because I had no idea what size a thing to grab. I was going to have to have a salesgirl help me and I just couldn't imagine how I was going to walk into a store and say, "I need a dress - can you tell me what size?"

After thinking about it for a day or so, I decided to tell the truth. I could walk in, look bashful and tell the truth. Then maybe the salesgirl wouldn't think I was a pervert and might actually help me. What did I have to lose except my self-respect?

I traveled to a mall about 20 miles away so that I could be a little surer that no one would recognize me. I thought that it might be easier at one of the big department stores than a smaller store, so I went in to the Macy's and headed for the dress department.

It was about 7pm on a Thursday night and not very crowded but I was a little intimidated as I walked through the women behind the cosmetic counters and past the women browsing through the shoes (I was going to have to get shoes, too!) and the hosiery. I didn't know how I was going to do this, but I knew I had to.

When I came to the dress department walked around it a couple of times and then walked in timidly, looking utterly clueless. A very pretty, very young blonde came up to me and smiled. "Can I help you sir?," she asked.

It was now or never. I cleared my throat. "Yes. I guess so." I looked at her and then looked down. "My wife and I had a bet on last week's Giants game and I lost. Now I have to watch this week's game in drag."

The salesgirl giggled and blushed, but she wasn't blushing nearly as deep as I was.

"I don't have a clue about sizes or anything, so I need all the help I can get." I smiled bashfully.

"OK," she said and giggled again. She pawed through a couple of racks and then looked at me and said, "I'm going to have to get my supervisor, sir. I've never fitted a man before. Do you mind.?"

I blushed and nodded no and tried to make myself as inconspicuous as I could. In a couple of moments, the girl came back with a woman in her mid-40's with a brittle blonde hairdo and a brass nameplate that said Mrs. Kelleher. Mrs. Kelleher smiled at me and simply said, "Yes?"

I told her about the bet and my predicament. She never stopped smiling. "I'm afraid we can't help you, sir." She emphasized the sir. "You need to go the women's department."

I looked confused. "Isn't this the women's department?"

"No sir," she explained, as if talking to a kindergartener. "This is the misses' dress department. The women's department is on the second floor. Or you might try one of the other stores in the mall that caters to larger sizes." She smiled again and walked away. I could hear the girl giggle again from behind a rack of cocktail dresses.

I was unbelievably embarrassed at this point. I slinked out of the store, past the cosmetics ladies and back into the mall. I wandered around the mall a couple of times with my eyes averted until I stopped in front of a store called Laura Brown's - A Shop for Women. A smaller sign in the entry way said clothes for real women in sizes for real women. I hesitated in the door way and then walked in, again trying my best to avoid eye contact with everyone.

After a minute or two, an attractive women in trim tan slacks, white blouse and navy jacket smiled warmly and asked if she could help me. Here we go again, I thought.

"Umm, yes. I know this sounds ridiculous, but I lost a bet to my wife on last week's game and I have to watch this week's game with her in drag." I blushed furiously and looked away.

"Oh my," she said, "you do you a problem. But who knows, you may come to like it."

I just stared at her. I swear her eyes twinkled.

"Do you know what size you are hon'?," she asked gently.

"Umm no. I'll need your help on that."

"That's no problem at all. I'm sure I can help." Did you have any idea of what you wanted?"

Oh my god. My brain just went completely blank My expression must have done the same.

"Well don't worry about it, I'm sure we can pull something together."

She pulled a tape measure out of her jacket pocket and told me to lift my arms. I glanced around and saw that nobody else was in the store, then lifted my arms. She measured me around the chest, then around my waist, then around my hips.

"OK, that's done. Now, do you have any idea of what you want? A dress, suit, skirt and blouse, or pantsuit? Sexy or simple? Color, style?"

Oh my god. I hadn't even though about that. Here I was in a store full of dresses and skirts and things and I didn't have any idea. I just thought of a dress in the abstract. Now I had to pick one out. I almost fainted. "Ummm, no. I dress I guess. Something simple."

"Actually, hon, I'd recommend against a dress for you. The way that most of them fit, to get something nice that fits you here," she explained as she touched my shoulders, "it would be far too blousy for your here" and she moved her hands down to my waist. "I think you might be better off with a skirt and maybe a nice blouse or sweater. Does that sound OK to you?"

I nodded.

"Alright then. And I think you probably would like something comfortable, not too revealing and probably more smart than sexy. Am I right?"

Again I nodded.

She leaned in to whisper to me. "You know, hon, you ought to relax. Wearing a skirt isn't going to kill you and if you're going to go through with this, you might as well try and have some fun doing it."

For some reason, that really loosened me up. I actually smiled back at her. "I guess. You might be right."

"Are you going to shave?"

The question took me by surprise and I reached up to my cheek.

"No dear, your legs. If you're going to shave your legs, you could wear pantyhose and that gives us more to choose from. If you're not, you'll have to wear tights and while that's OK, some outfits just won't look right if you're in tights."

Again, I blanched. "I hadn't even thought about that," I blurted.

"OK, that's not a problem. We'll assume you'll wear tights so you can make up your mind later." She spun around and walked over to the other side of the store, looking around her as she went. I followed slowly, watching her every move. When she turned around again to face me, she held up an outfit and asked brightly, "Well, what do you think?"

The skirt was long and looked soft. It was mostly a dark brown, with a border near the hem that was sort of a paisley with swirls of gold, maroon and dark green. Above it, she held a light tan mock turtleneck sweater. "That looks great," I said, relieved that this process was coming close to an end. I reached for my wallet and headed towards the cash register.

"I think you're going to have to try it on." I just stared at her. "I can only guess at your size, you know. We're not going to know if they fit until you try them." She held them out towards me and nodded to the dressing room. "Give me a shout if you need anything. I'm Catherine."

The dressing room was just a few feet away but it wasn't until I closed the door that I noticed the door not only didn't go to the ceiling, it didn't go to the floor. I wondered if anyone was going to notice my heavy socks and hairy legs under the door. I took off my shoes, jeans and shirt and let them drop on the floor. I stepped into the skirt, but it wouldn't slide up past my butt. Then I noticed a zipper and after undoing it, I had no problems. I pulled on the sweater and everything seemed OK. I looked like hell in the mirror, but what did I expect?

"How are you doing in there hon?" I heard Catherine ask.

"Umm. OK, I guess. It'll work."

"Come out and let me see," she replied.

"That's OK. I'm alright.

"Don't be silly." She opened the door to the dressing room and looked at me critically. I was absolutely mortified, standing there in a skirt with the door wide open for anyone to see (and by now there were about a half-dozen customers scattered about the store in additional to another couple of saleswomen).

"Well the first thing is that we ladies usually wear our zippers in the back." With that, she grabbed the waist of my skirt and yanked it around until the zipper was indeed, in the back. That a couple of her yanks included my boxer shorts thus inducing a shocking rearrangement of things I thought was better left unsaid.

"That's much better," she said. Although I think this skirt is a bit big. It might look better one size smaller. What do you think?" She didn't wait for me to answer, but left to go to the rack for another skirt, leaving the door open. I closed it as quickly as I could but she was back in an instant to open it back up again.

"Here, try this one. Remember, zipper in the back."

I closed the door, unzipped and dropped my skirt to the ground and put the new one on. Zipping up the back was a bit of a contortion, but I managed.
"All set?" Catherine asked. She opened the door just as I was finished pulling up the zipper. "Yes, that's much better."

Then she spun me around and unzipped my skirt. "I think that this would look nicer if you tucked in the sweater," she explained as she smoothed the bottom of the sweater down around my boxers before zipping me up again. "Turn around."

I did as ordered. "Hmmmm. Wait right here." I wondered where she expected me to go, dressed like that.

She came back with a belt and a scarf. The belt was wide with a big brass buckle and the scarf was dark brown with a pattern that was similar to the one on my skirt. She wrapped the belt around me and fastened it in front, then spun the scarf a couple of time around itself and draped it around my neck and over my left shoulder.

"There! You're perfect." I turned around to look at the mirror in the dressing room and I have to admit it wasn't all that bad. The sweater and skirt felt soft next to my body and I liked the way everything sort of flowed gently. At least from the calves to the neck. The legs and head certainly gave the lie to the prettiness of the ensemble and if you looked closely you'd notice that the sweater hung in a straight cylinder when it would have preferred nice breasts and a waist.

I shook myself out of my reverie in time to see Catherine grinning at me. "See, now that isn't so bad is it?"

I smiled shyly back at her. "I guess these will do."

"Not yet," she said. "You'll need some tights, shoes and underwear, maybe some jewelry, if you want to do this right. I'll get your tights while you get dressed." She began to walk away, but turned around. "Unless you want to wear those home?" Again, she smiled broadly as she walked to the hosiery racks.
I just scuttled back into the dressing room to get back into my clothes.

When I brought everything to the counter, Catherine gave me a slim box. "Here are your tights, hon. They're chocolate brown, so they will complement your skirt perfectly."

"Thanks," I mumbled.

"I'd love to see you when you get everything together. I think you'd be a doll," she said as she rang up the sale. The bill came to more than I expected (this wasn't going to be cheap!) and I gave her my credit card. As she was processing the credit card, she said "There's a store about five doors down called Under It All where you can pick up your underwear. I don't think the department stores will have what you need in your size. And there's about a half-dozen shoe stores and I'm sure you'll find something nice at one of them."

She bagged up my outfit. "Here's a credit card application in case you want to open up an account and a 15% off coupon for your next purchase."

My "next" purchase? "Ummm, thanks. You've been very helpful."

"Why thank you! Now you have a nice day, and hon - relax. You're not the first man I've seen in here and you won't be the last." She smiled very graciously at me and I left, not knowing if I was supposed to be relieved or embarrassed.

I turned in the direction of Under It All and walked slowly in the direction, stopping before I reached the door. There were a pair of mannequins, one dressed in a very sexy burgundy bra and panty set and one in a teddy made out of the same burgundy material with some black lace accents. Through the glass I could racks of nightgowns, bras, panties, teddies, slips and god knows what else. The store wasn't empty, either. There was a woman shopping with her teenage daughter, a couple of women in business suits, an older woman by herself and a young mother with a toddler in hand. I also saw a tall, trim, middle-aged woman in a flowery dress who looked to be running the place and a couple of girls in their 20s who were probably the shop assistants.

As I was standing outside the door, losing my nerve, the woman in the flowery dress poked her head outside the shop, glanced at the shopping bag from Laura Brown's that dangled from my hand and said "You must be the gentleman that Catherine just called about. Come in, come in."

I followed her as she walked to the counter at the back. The store was tightly packed and everywhere I went I plowed through wisps of softness. I felt like the proverbial bull in a China closet. A couple of the customers glanced at me but I couldn't tell what they were thinking.

"Now then, how can I help you?"

I told her about the bet and that I'd already purchased a skirt and sweater and that I needed some underwear.

"Do you know what you're looking for, sir?"

I just shook my head. "Not really, no. I guess I'll need a bra and a pair of underwear." I just couldn't bring myself to say the word panties.

"Well that's still alright. You probably don't know your size, right?" I think she considered my blushing nod a sign of agreement. "I didn't think so. Take off your jacket and raise your arms."

I did as I was told and she took a tape measure and measured around my chest. I was glad my back was toward the store because I couldn't imagine what anyone who saw this may have been thinking. "Looks like a 40," she said to herself. Then she raised the tape measure up a couple of inches up and measured again, only this time she just wrinkled her nose and grunted softly.

"Were you planning on having breasts, sir?" she asked.

"I suppose I should."

"Do you have any preferences - small, large?" Although she was trying desperately to keep a straight face, I could see the traces of a smile dancing at the edges of her lips. How could I possibly answer a question like that? I felt like every time I took a breath I was falling deeper and deeper into a hole.

"I don't really know. I hadn't thought about it. I guess I'll go along with whatever you think is best."

"I thought you were going to say something like that," she said, almost to herself. The hint of a smile was working it's way open now, too.

"I need to measure you again," she said as she drew the tape measure around my hips and then again around my waist. "You're a 7 or an 8 in panties." She turned around to one of the shop assistants. "Linda, could you see if we have either "Lace Fantasies" or "Pretty All Day" in a white soft-cup, 40B and 40C and matching panties in 7 and 8 for this gentleman." She turned to me and excused herself. "I'll be back with you in a moment, after I help these ladies." I saw the woman with her teenage daughter doing their best to stare at me without appearing to even look at me. I looked around for a hole I could drop into.

After a couple of minutes, Linda tapped me on the shoulder and spilled an armload of white lace on the counter, arranging it for me. "I couldn't find a 40B in the styles Andrea asked me for, but I picked a few other things out. These are really pretty," she said as she arranged one of the bras over one of the panties. She was right, they were. The panties had a delicate stretch lace V pattern in the front that was repeated around the legs. The bra had a matching pattern on the top half of the cups and I deliciously imagined Carol in an outfit like this. Linda smiled sweetly and said, "I'm sure whoever you're giving these too is going to love them and..."

At that point Andrea returned, picked up the panties and held them in front of my pants to gauge the size. I could see Linda blush a bit and stifle a giggle. "Hmm I still can't tell." She picked up the other pair of the same style in a different style and held those up as well, then shook her head. "Well, anyway, you'll need to try this on to check the size." She handed me the bra and started to steer me to the dressing room.

Well this was going just a bit too far, I thought. It was bad enough that I was going to wear a bra with my wife in the privacy of my own home but in a store, in a mall? No way. I started to object, but Andrea would have none of it. "Don't be silly, the dressing room is private. Use that one on the right," she said as she pushed me towards it with the bra in my hand.

I closed the door behind me and took off my shirt and undershirt. I slipped my arms through the straps as I'd seen Carol do a thousand time but I was darned if I could reach behind me to hook it up. As I struggled, I heard Andrea explain to Linda what was going on.

"That's so cute!" I heard Linda squeal. "So, he's already got, like, a skirt and stuff?" I didn't hear Andrea's reply but Linda must have approved. "Oh wow, that's so neat!"

I decided to cheat. I took the bra off, then turned it around so the hooks were in front of me. I hooked it up, then twisted it back the right way and started to try to get my arms inside the straps again.

"Y'know, though, Andrea, if he's going to wear tights (how did she know that - did the saleslady from Laura Brown's tell them what I bought?) these, like, pretty panties are going to be wasted. And since he's a guy, he doesn't have, like hips or a waist, right? Maybe he'd be better off with these?"

I wish I knew what Linda was showing her, but I was having a devil of a time on my own.

"I think you're right, Linda. These probably would work better. I wonder if he's having a problem in there." I heard her muffle a giggle, too. "Maybe I should check."

She knocked on the door and walked in without waiting for me to answer. "Oh my, you seem to be having some difficulty. Here, let me show you. The first thing, is that you haven't adjusted the straps properly. You're going to need as much length here as you can get." She fiddled with this little buckle-like thing and then pulled the cups down a bit. "That should be easier," she said, as she helped guide my arms through the straps. "Usually, you'd put your arms in first and then hook it up, but I'll bet you hooked it up in front, first, right?"

I just nodded. "I thought so. You'll get better with practice" What did that mean, I thought? She smoothed out the straps, tugged on the cups, tugged on the back, ran her finger around the back. "This fits well here, so I think we have the right size. We don't have this size in a smaller cup, though. What are you going to here?" she asked as she tweaked my empty cup.

"I'll probably just stuff it with something," I mumbled.

"Socks don't work very well," she said. "They get lumpy and they just don't look right. We have mastectomy forms but they get very expensive." I blanched. "What you can do, though, is to buy a pair of knee-highs and fill them with about a cup and a half of birdseed, or you could even do the same thing with a baggie and about the same amount of water. Both will fill these out nicely.

"Stay right here. I'll be right back." She didn't close the door to the dressing room behind her, so I lunged toward the doorknob, just as that teenage girl walked past me towards her own dressing room. I could have died. After a couple of minutes, Andrea knocked. "Are you decent," she said, but she didn't wait for an answer before she came in.

"This is called a waist nipper," she said. "It's a girdle with a high waist. Wear your tights under it and they won't sag, but more important it will give you a little definition here (and she put her hands around my waist) and here (as she placed her hands on my butt). This is an XL and it should fit but I think you should try it on. You'll have to leave your underwear on. Here." She gave me the girdle and left, again without closing the door.

I was out of my league. Not only could I not figure out which end was the front, I couldn't imagine how I could put these on over my boxer shorts. I just held them stupidly until Andrea knocked again and opened the door. "I thought you might have some problems," she explained. "They go on this way," she explained, showing me which way was the front. "Wiggle them up your legs and when you reach the top, pull up the waist. Then hook all these hooks and you're all set. By the way, these will never work with the undies you're wearing now. I brought you some panties. You'll have to buy them but they're on sale and I'll discount them when we ring up the sale. Let me know when you're all set."

The panties were simple, white briefs, for which I was grateful. After she left, I slipped out of my boxers and put on the panties, which seemed to fit like a second skin. Then I slid the girdle up my legs, pulled up the legs and hooked the hooks, just as instructed. It took some effort to attach all those hooks, but when it was all done it didn't feel all that uncomfortable. In fact, I was more than a little excited, and I'm not sure that this wasn't obvious when Andrea came back into the dressing room, this time without knocking.

"I think this is just about perfect," she exclaimed, as she tugged a little on the legs and then ran her fingers around the top band. "Don't you think so?" I nodded mutely. "Oh don't be such a fuddy duddy. This will give you a nice, girlish figure and, who knows, you may enjoy it! Get dressed and bring your things to the counter and we'll ring you up."

As soon as she left, I got out of those things as quickly as I could, which frankly wasn't all that quick as I was still having some problems with these hooks and having the hooks in the back of the bra was an ingeniously torturous device. Eventually, though, I was back in my flannels and jeans and standing in front of Linda at the cash register with my new "treasures."

She took the bra, girdle and panties from me and elaborately folded them while placing them back in their boxes. "Will that be all sir?" she asked.

"Umm, yes."

"Would you like to join our bra and panty club.? Buy 10 panties or 5 bras and get one free?"

I just stared at her.

"It's a promotion we're running right now and I have to ask," she said, with a conspiratorial air. "But it is a really cool deal if you're interested."

"I don't think so," I replied. She rang up the sale and handed my purchases. "Thank you very much and we hope to see you again soon, sir." She positively beamed. I mumbled my thanks and tried to get out of the store as quickly as I could without knocking anything over.

I left the store and took a deep breath. While I felt some relief, I don't know whether I was more relieved that it was over or that I didn't die from embarrassment. I didn't think I could do what I just did, but I did and Catherine, Andrea and Linda were all nice and my essential parts hadn't dropped off when I tried my new skirt or my bra. This may not turn out to be as bad as I thought.

I assessed what I still needed to do. I needed shoes and I needed to do something about my hair and makeup. I didn't remember if Catherine recommended any shoe stores so I just started to circle the mall. The first shoe store I saw was all athletic shoes and the next one had a clerk who looked like Al Bundy leaning on the counter. I just couldn't see asking him for help so I walked on. A few more stores down I saw a store that looked promising. All the shoes in the window were women's, both casual and dress, and both of the clerks were women in their 20s. One had short, black hair and the other longish, brown hair pulled back in a ponytail. There were customers in the store right then.

I went into the store and started looking around, while the two women continued to chat with each other. After what seemed like an eternity, the one with black hair asked "Do you need some help?"

I walked over to the counter. "I think I do. I had a bet with my wife and I have to watch this Sunday's game in drag. Right now," and I raised my two bags, "all I need is shoes."

"Oh really," the black-haired one said, raising an eyebrow. "This could be fun," she remarked to her associate. "Do you know what you're looking for?"

Why did everybody ask that question, I thought to myself. "Uh, no, not exactly. Whatever fits and whatever goes with what I've already got, I guess."

"Can we see?" she asked.

"Sure, I suppose." I gave her the bag from Laura Brown's. She pulled out the skirt and held it up against my waist. I wasn't expecting this. There were no racks to hide me, just a big, wide glass store front that was open to the entire mall. I quickly backed away but she reached out and put her hand on my shoulder.

"I'm sorry, I didn't want to embarrass you. I just wanted to see what we have to work with. OK?"

I nodded.

"That's a pretty skirt and we've got lots of things that will go well with it. What else are you wearing?"

I pulled out the sweater and the brown tights.

"Oh that's very smart. You're gonna look great honey. Don't you think he'll look cute, Suzy?" She asked her partner.

"Absolutely." They were talking to each other as if I weren't even there.

"What do you think - penny loafers might work, or faux alligator loafer, maybe." Suzy picked up a couple of shoes from the display and held them up for my approval. They both looked fine to me, but what did I know?

"They're a little plain, Suzy" the black-haired woman said. "I think an outfit like that needs something with a little more character." She turned to me. "Why don't you have a seat, sir."

As I was doing what I was told, she reached into a little box on the counter. "Take off your socks and these on or we'll never get a proper size." She handed me a couple of little balls of nylon that I found out later were called peds. It took me a second, but I got them on. I felt like an idiot.

By this time, Suzy had gone off to help another customer (who was looking warily at me). My saleswoman squatted down with that contraption they use for measuring foot sizes and after fiddling around a bit told me I was a 9 and that she would be right back and that I should relax (how many times had I heard that today!).

Just as promised, she came back with an armload of shoeboxes. As she tried on shoe after shoe on my feet, she kept chattering away at me and I didn't hear a word. I was frozen with fear that someone I knew would see me trying on women's shoes over ped-covered feet in this glass enclosed shoe store in the middle of a popular mall. She tried on big heels and little heels and shoes with straps and shoes that covered my toes and shoes that didn't cover my toes and some of them fit and some of them didn't but at this point I was dazed.

"So, what do you think?" She was expecting me to make a decision and my mind was absolutely blank. I looked down at my feet and for reasons I'll never understand, like a bolt out of the blue, what I saw made sense. I was wearing (left foot only) a 2" clunky heel with a big brass buckle and an open toe and I liked the way it looked and I liked the way my foot felt in it.

"I think those will be fine, " I squeaked.

"I thought so. These will look really nice with your outfit. They really do go together." She put the other shoe on and told me to stand up. I did, and shook a little when I got upright, but then felt fine. I thought the shoes looked great and my feeling of weirdness completely disappeared, until I saw one of Suzy's customer's grinning at me. I sat down in a hurry and my black-haired saleswoman smiled and said, "Don't worry about anything. You'll never see her again, and besides, you've chosen a really great pair of shoes."

She took off the shoes and put them back in the box and headed back towards the register. I couldn't figure out what to do with the peds, so I put my socks on over them and followed her. After she rang up the sale, she asked "Will there be anything else - ooops - sorry - force of habit," took my credit card and finished up.

I thanked her and as I was leaving, she gave me a wide smile and told me to "have a real good time, OK? By the way, we'd love to have a picture if you're OK with that." I must have blushed a dozen shades of crimson as I walked out, but to tell the truth, I wasn't sure if I was blushing because I was embarrassed or because I was beginning to realize that I starting to like the idea of what I was doing.

The last thing on my list was hair and makeup. I knew that if I went into the local drugstore and bought a bunch of stuff and did it myself that I'd look more like Bozo the Clown than anything else, but I had no idea of what else to do. I knew I needed help but a beauty salon? The idea seemed ridiculous but having already tried on a skirt, a bra and 3" heels how much more ridiculous could I get?

On the ground floor of the mall near the offices and near the parking garage (thus on the way out) was a shop called Rita's, written with big, curly script across the windows. Underneath, in smaller, but equally florid type it said hair - cosmetics - nails. I figured that this was the kind of place I needed, so I went in. Fortunately, there was nobody in the place except for a tall, big-haired redhead sitting in one of the customer chairs and a forty-ish woman with short, black hair sitting behind the cash register sipping coffee and reading Vogue.

I paused in front of the register. "Melpyu?," she said, without looking up. After a second, it dawned on me that this was a contraction of "May I help you?"

"Yes, I hope so." I launched into my sad story. "I've lost a bet with my wife and I have to spend this Sunday with her in drag. I've got the clothes (and I waved my bags at her) but I'm going to need help with my makeup and hair, I guess, but not today, first thing on Sunday. Or right after you open, because you probably don't open until noon. Can you help me out?" I was babbling and she was staring at me but at this point my mouth stopped.

After a couple of seconds, she reached out and took hold of my chin and moved it to the left and then to the right. Then she stood up and ran her fingers through my hair (which is fairly long for a man's but not real long) a couple of times. Then she sat back down and exhaled loudly. "Lemme see what's in the bags." I gave her the bags and she poked around a little, then stared into space for a couple of seconds and turned back to me.

"Y'know, the girls I usually have working Sunday would probably get you arrested but for something like this, I'll come in myself."

Then I exhaled.

"What I want you to do is this," she said to me. "I want you to shave real close as late as you can Sunday morning. And I want you to wear something that ain't too male or too female. Jeans and a T-shirt would be OK, but you ain't gonna look like a girl coming in and you ain't gonna look like a boy going out, so you gotta straddle. And you prob'ly oughta wear a baseball cap or something with a bill that you can pull down over your face when you leave, 'less you think you can be comfortable being seen in eyeshadow 'n shit. You think you can do that?"

"Yes" I replied with more confidence than I really thought.

"Alright, then. We open at noon, but if you came a few minutes early I'd let you in. And honey, one more thing. You forgot jewelry."

****************

I put my purchases in the trunk and drove right home. I was so relieved to find that Carol's car wasn't in the driveway. I hauled the bags upstairs and hid them in the corner of my closet, underneath the luggage. I then poured myself a stiff drink and sat on the back steps, watching the late afternoon sun while ruminating on the day's experiences. I couldn't quite reconcile the embarrassment I felt with the image of my in my new skirt, sweater and shoes, with curves in all the right places. In a way, I couldn't wait for this Sunday to come.

I didn't get any work done on Friday because all I could do was think about those bags lurking in my closet. I left the office as early as I could and headed back to the mall, where I picked up a pair of clip-on earrings, gold colored with an imitation opal in the center and some gold-colored bangles. I marched right into the store, right over to what I wanted, made my selections and brought them right over to the counter. I was so proud of myself.

Carol was in the kitchen when I got home so I had to sneak the bag past her, but she still wasn't talking to me or paying any attention to me, so I didn't have to sneak too hard.

Saturday was awful. I still couldn't quite figure out whether I was terrified of getting all dressed up on Sunday or I couldn't wait to put on my new skirt. I couldn't concentrate on anything else and all day I kept bumping into things and dropping things. I was a mess. The only thing I did successfully all day was make my breasts out of baggies and water, the way the woman at Under It All instructed. I was amazingly precise when doing that.

***************

Finally, Sunday morning arrived. Although I hardly slept a wink, I stayed in bed until Carol went downstairs around 9:30. I went into the bathroom and took a long look in the mirror.

"Here goes," I said to myself and began to shave. I usually use an electric razor but I bought a safety razor for the occasion to get a closer shave. I was extra careful and took a long time and hoped that Rita would approve. As I stood there washing my face, I decided in an impulsive moment to do my legs as well and put the razor and shaving cream in the shower. After wetting down under the hot spray, I foamed my legs, took a deep breath and did it! There were a couple of moments when I felt like a pretzel (ever try to shave the tops of your feet?) but I did it. As I toweled off, I couldn't begin to describe the feelings I got as I rubbed my smooth, now hairless legs.

Back in the bedroom, I got my bags out of the closet and found the tights. I'd watched Carol putting on pantyhose before, so I bundled up each leg in a ball and then sort of rolled them up my legs, then tugged the top up to my waist making sure that it was snug where it ought to be snug. So far, so good.

The girdle was next and I pulled it on over the tights and then spent an agonizing couple of minutes hooking all those damn hooks, but when I was done I glanced in the mirror and to my surprise, I had a waist, I had a butt and I didn't have much in the front. Now it wasn't much of a waist and it wasn't much of a butt, but it was a whole lot more that I had about three minutes ago. The bra was next and I put it on just like Andrea at Under It All had showed me. I didn't put in my baggie/falsies yet. That would come later.

Then I put on my new sweater and a pair of jeans. A big, gray sweatshirt over the sweater, a pair of dingy "white" sweatsocks over the tights, my sneakers, a light jacket and my Giants cap and I fairly streaked out the house to the car. I told Carol as I was leaving that I had a couple of errands but I don't know if she heard me or if she cared.

As I pulled out of the driveway, I realized that I had at least an hour to kill before Rita's opened so I just sort of drove around aimlessly once I got out of my neighborhood. At first, the tightness of the girdle and the bra and the feeling of material hugging the length of my legs was a little disconcerting but not unpleasant. But the more I drove around, the more pleasant it became. I don't know if I could ever get used to having a bra stretching across my chest and over my shoulders, but this rest of this wasn't turning out to be too bad at all. Realizing that made me more confused than ever.

I pulled into the mall parking lot around 11:30 and just sat in my car gathering courage. After a few minutes of deep breathing, I opened the door and marched out towards Rene's. I went straight up to the door and Rene was there to meet me. She grinned a bit and said "I wasn't sure you'd come." She beckoned me towards one of the chairs towards the back.

"Have a seat, hon. My name's Adelle and you're...?" She looked at me expectantly. I looked at her with confusion and then looked at the sign on the window. "I bought this place a couple of years ago and it seemed stupid to replace a perfectly good sign. You still haven't told me your name."

I did and then she tied a bib around my neck and adjusted my head to and fro until she was satisfied. "I want to start with your hair because I want to try something and I won't know if it'll work until you're ready to leave."

I mumbled an "OK."

"I think I might be able to use your own hair so you won't need to wear a wig," and she grabbed a couple of brushes and a comb and started attacking my hair. Attacking was the only work to use. She brushed it this way and that, pulled it up and brushed it down and just did all kinds of things to it. When she was finished, instead of sweeping across my forehead my hair fell in bangs. Instead of being parted on the left and swept back, it fell evenly from a part in the center. She picked up a brush that looked like a vicious drain cleaner and curled the hair that now dropped below my ears around it and then sprayed some stuff on it. When she unwrapped the hair from the brush, it held a little of the curl inwards. She did this all around the bottom.

When she picked up the scissors, I almost panicked. "Don't worry hon, I'm not going to do anything that anyone will see when you comb it back into your boy style." What she wound up doing was evening my bangs and trimming some rebelliously uneven strands from above my collar.

"There," and she showed me her handiwork in the mirror. It was definitely a woman's style and I thought it was fine but that I looked silly in it.

"Great," I said, but I don't think I sounded real enthusiastic.

"I want to see how this holds up while I do everything else. If it's still there when I'm done, I'll show you how to brush it to keep it fresh and you'll be all set. Then, if you want to, you can comb it back to your boy style. Now let's do your nails."

She reached into a small tray and dabbed something on the index finger of my left hand. "This is an adhesive that will hold your nails in place. Your wife will know how to take them off," she explained as she finished with the glue and then placed a long, sculpted piece of plastic over my own nail. It looked to me to stick out about six inches from my fingertip but subconsciously I knew I was exaggerating.

She finished the rest of hands, then spent a few minutes with a nail file sanding, poking and pushing things around until she was satisfied. Then Adelle sat back and took out some nail polish and began to paint. The color was a deep, rich reddish/brown that reminded me of mahogany. When she was finished, I couldn't describe how amazed I was at how they looked or how strange they felt.

"Now keep your hands still so they'll dry properly and I'll get to work on your face. You've already shaved, I hope?" I nodded. "Good."

With that, she started to work. By this time, another couple of her assistants had come in and glanced at us, stifling giggles but not saying anything. I began to wonder how I was going to get out of here since the mall was going to be open.

She applied a creamy kind of thing all over my face, smoothing it out first with her fingers and then with a cotton ball. When she lifted my bangs to cover my forehead and they fall back into place, she smiled.

Some powdery things followed. First one that was applied all over the creamy stuff she just applied, then a couple of different ones just to my cheeks. I just stared off into space. I was afraid to glance at a mirror.

"Now I want you to hold perfectly still," she said as she pulled out the mascara (I knew what this was, because I'd heard Carol call it that when she used it). She leaned in real close and began brushing my eyelashes, upper and lower. Then she reached for a couple more different things and began to brush my eyelids and the area under my eyebrows.

"Your brows are a little thicker than I'd like. You want me to thin them out? They'll probably grow back." My eyes must have registered major alarm, because she shook her head and said "I didn't think so. I'll just try to shape them a little." She took a tiny comb and began to comb my eyebrows.

Then, after she was done with that, she stepped back and looked at me. I was so self-conscious I was sure I was blushing furiously. She touched my chin and moved my head a little this way and that and then spent the next few minutes dabbing and poking at my with various things.

"Blink." I did. "Shake your head." I did.

"Well, I think I did a pretty good job - how 'bout you hon?" She made me look into the mirror and what I saw shocked me. I looked good. I looked very good. Staring back at me was the face that could have belonged to a successful businesswoman. Short, no-nonsense haircut, dark eyes touched with shades of gold and brown and flawless skin with a touch of color on the cheeks. The only thing missing was lipstick (even I knew enough to know that lipstick was missing.

"I didn't put the lipstick on hon, because it would show up too much when you leave. If you pull your cap down low, most of your face will be hidden and folks will probably not notice that you're wearing makeup. Put on the lipstick now and they're gonna know." I silently blessed her. "So what I want you to do is to pay real close attention when I show you what to do and you can put it on yourself when you get home."

She showed me what to do and then gave me the tube. She also showed me what to do with my hair. "After sticking it under that cap and driving home, it's going to need a touch up."

When it came time to pay her, I had the hardest time trying to get my wallet out of my pants with those nails. When I finally succeeded, I realized I didn't know what the tipping conventions were in a place like this. I gave her a big tip anyway.

"You're usually not supposed to tip the owner," she said. "But in this case, I think it's appropriate." She smiled. Have a good time today, hon."

As I opened the door to leave, I heard Adelle call after me. "Hey hon?" I turned around. "Hands in the pockets until you get to your car"

I drove home as fast as I could, making sure to keep my hands on the bottom of the steering wheel. When I got home, I headed straight upstairs, catching a glimpse of Carol sitting on the couch reading a book. I took one of her brushes and brushed my hair back into condition. Then I took out my lipstick and carefully applied it to my lips exactly as Adelle had instructed.

Off came the sweatsocks, the jeans and the sweatshirt (I should have waited to fix my hair, I said to myself). I took my skirt out of the closet and put it on, pulling the belt tight to emphasize my waist. I knotted my scarf and draped it around my neck and over my left shoulder. Next came the earrings and the bracelets.

I started to bend over to get my shoes, but about half way down I thought that bending over wouldn't be very ladylike so I squatted down and then sat on the bed to put them on. As I stood up I didn't know what to expect, but when I straightened up and looked in the mirror, I felt and looked simply wonderful and I was amazed at myself.

A quick check in the mirror made me remember that I forget a couple of very important items and I got my "breasts" from the drawer and put them in place. Readjusted the sweater and the skirt. Rebrushed my hair, squirted on a little of Carol's favorite perfume and then walked down the stairs as quietly as I could.

In the kitchen, I placed the video, two glasses and the bottle of wine on a basket. One last glimpse in the downstairs bathroom mirror and I was ready.

I peeked into the living room and said "Ta da," in as quiet, breathy and romantic a voice as I could muster. Then I swirled into the room, placed the tray gently on the coffee table and spun around in front of Carol.

The expression on her face was priceless. Surprise gave way to shock which gave way to a couple of lonely tears running down her face and then the widest smile I'd seen on her in years. All the money, time and embarrassment of the last few days was worth it just to see the smile on her beautiful face.

"Honey, I love you so much," she said as she stood up and hugged me. Our breasts pushed together and as we kissed and hugged with a deep, loving passion.

"I love you too Carol and I'm so sorry for the way I've acted."

I'd tell you the rest of this story, but there are some things between a husband and a wife that must remain private.

Part One

I couldn’t imagine a more delightful way to spend a Tuesday afternoon.

Outside, it was a cold, dreary late November day. The sun woke up in the morning and then decided not to bother, leaving a gray pallor over just everything. And while it wasn’t raining or snowing, those clouds certainly wanted to do something and the air was just as damp as if it were raining.

Inside, though, I was curled up on my couch, my stockinged feet tucked under me, some Stan Getz on the stereo, a chilled glass on Italian white wine in one hand and a Linda Barnes mystery in the other. I love Linda Barnes’ books. Part of it, of course, is that she’s a great writer whose books are as funny as they are engrossing. Another part of it, though, is that I imagine myself as Barnes’ character, Carlotta Carlyle. I may not have a beautiful shock of thick red hair (my hair is dark brown and a little on the short side) but we share a 6’1” height and size 12 feet. One big difference between us is that I have much better fashion sense than Carlotta.

I guess if I was chasing bad guys all over the place I might settle for jeans, T-shirts and sneaks, too, but I don’t chase bad guys and I wouldn’t be caught dead in jeans, T-shirts and sneaks. Take that Tuesday, for instance. I was wearing a knee-length Stewart plaid jumper over a soft, bulky ivory cowl-necked sweater. I loved that sweater, which looked like Angora but wasn’t and I knew it worked well with the jumper, which I picked up the spring before for $10 at an end of season sale rack at Sears. I usually wore this outfit with black tights but today decided on pantyhose instead. I don’t know why. I’d kicked off my sensible 1” pumps and they were lying beneath me on the floor. I wasn’t wearing much makeup, just some lipstick (as bright red as the red in the plaid!). My earrings were gold-colored with faux opals placed just a bit off-center and I’d borrowed a couple of my wife’s gold bangles and a gold leaf-cluster pin for the jumper. It was the season, after all.

My wife’s bangles and pin, I hear you say?

Yes, my wife’s. I’m a crossdresser, have been as long as I can remember and I take every opportunity I can to indulge. Those opportunities usually take place when Kathleen (that’s her name) is working and I’m not. I’m a librarian at a private school and generally work Monday to Friday, but we get lots more vacation time than most folks. This week, for example, was Thanksgiving week and the school was closed, so I took care of some paperwork and administrative matters on Monday and took the rest of the week off. Since it’s a private school, too, none of the faculty or students live in the area, so I never have to worry about meeting someone from work when I shop. Kathleen, on the other hand, is the assistant manager of the customer service department of one of the last local banks in our area. She works Tuesday through Saturdays.

At the very least, then, I get all day Saturday for myself. I’ll usually go shopping in the morning, maybe pick up something new and cute, maybe something functional, maybe nothing at all. Then I’ll get dressed the way I feel that day, in something romantic, or professional, or casual, or silly. I’ll work around the house a little, then relax with a nice book and some music and around 4 o’clock or so I’ll begin preparing dinner. By 5:30, I’m back upstairs, changing into my boy clothes again before Kathleen gets home. She doesn’t know, you see.

I’ve never told Kathleen about this part of me. I didn’t mean to be deliberately deceptive, but it just never seemed right. I mean, you just can blurt out one day at dinner, “By the way, honey, I’m a crossdresser. Does that bother you and can I borrow your silver strap sandals tonight?” And if I was going to do something like that, I should have done it years ago. Now, after eight years of marriage, there’s not only the crossdressing but the fact that I’ve been hiding it for ten years (we dated for two years before we got married) would be an issue.

Besides, what possible benefit could there be to telling her? On the downside, I could very easily hurt the one woman I’ve ever truly loved. She could leave me. She could become disgusted with me. She could hate me. I don’t think I could bear any of those things. Was there an upside? She could accept me, but then what? I could dress more often and more openly, but what would that mean and would that be worth the risk? All in all, I think I’d prefer to keep Martha (my female alter ego) in the closet with my dresses and lingerie.

Every once in a while I agonized over these thoughts, but those mental torture sessions were growing further and further apart. These days, I was more often than not perfectly content to enjoy a few hours as Martha, like I was doing that Tuesday. The CD-changer had replaced Getz with Anita O’Day. The book was beginning to get complicated. I was dimly aware that it was starting to rain and the wind was picking up. I wasn’t aware at all of the key turning in the front door lock.

“Hi honey, I’m home early. There was a power failure and they… closed… the… bank…” Kathleen’s voice dropped to a hoarse whisper when she saw me.

I don’t know which of us was more shocked. I know that my heart just stopped dead. My brain froze. I couldn’t move. A million thoughts raced through my mind. Should I bolt out of the room? Begin to “confess?” Leave with as much dignity as I could muster? Pretend there was nothing wrong? Cry? Promise I’d never do it again? I wanted to do all of these things and needed to do something but I couldn’t move or speak.

Kathleen was equally paralyzed. Her mouth was open as she stared at me. I could tell that her brain was sending messages to her tongue, but I could also tell that nothing was coming out. Her hands still held the keys in the lock that she had just opened.

It seemed to me that we just looked at each other for hours, but it could only have been a few seconds. The abruptly, Kathleen spun and walked out the door without saying a word. A few seconds later, I heard her car start up and pull out of the driveway.

I was devastated.

I went upstairs and almost ripped my clothes off. I’m usually very careful to pack everything just so when I’m getting ready to dress as a boy again, but that day I just crammed everything into a bag and flung them into my closet. In the bathroom, I rubbed my lips raw trying to get rid of my lipstick. No matter how hard I tried, though, every time I looked in the mirror I saw traces of bright red lipstick mocking me. I didn’t think I’d ever get back to the way I “should” be.

After a while, I gave up. Got into my khakis and a golf shirt and went downstairs to wait. I watched television but I couldn’t tell you what was on. I didn’t know if Kathleen were coming back. I desperately hoped she was, but I had no idea how to act or what to say when she did. A million scenarios danced in my mind, none of them good.

I wondered if I should leave.

I swore to myself that I’d never do it again. Never. A voice in the back of my head kept whispering that I could not possibly “never do it again,” but I tried to shout it down, saying that I had to. I had to put Martha behind me. I had to.

Kathleen came home about an hour later. I was incredibly relieved to hear her car pull up but terrified as to what would happen. As she came in the front door, she avoided looking at me.

“I don’t think I want to talk right now Mark,” she said. “Maybe tomorrow. Right now, I’m just going to fix myself something to eat and go upstairs to read.”

That’s what she did and spent the rest of the afternoon and evening brooding in the living room. I tried to read and tried to watch TV but couldn’t concentrate. I reheated some leftover Chinese chicken but spent more time moving it around my plate than eating it. Finally, a little after midnight, I slipped softly upstairs, undressed and got quietly into bed. I don’t know if Kathleen was sleeping or not, but her back was turned to me and she didn’t stir when I got into bed. I don’t know if I slept that night either, but I don’t remember the sun coming up and I don’t remember Kathleen turning over and placing her hand on my hip. That’s where it was, though, early the next morning right before she stretched, yawned and got up.

I gave her about 15 minutes after she went downstairs before I got up. It seemed to take forever to brush my teeth, shower and dress but it was really only a few minutes before I clomped downstairs in jeans and my most macho flannel shirt. That was kinda funny, too, because when I reached the kitchen, Kathleen was wearing jeans and a flannel shirt over a T-shirt.

“Kathy, I am so sorry about yesterday. I’m…”

“Stop talking Mark,” she said with a smile. “I’m not upset. I’m surprised. I’m a little unhappy, I suppose, that you felt you had to keep your hobby a secret, but I’m not upset.”

I don’t think her words registered with me right then. “You have every right to be mad at me.” I looked at the floor, then at her, then at the floor again. “I’ll stop. I’ll stop. I promise I’ll never dress up again.”

“Don’t be ridiculous, honey, of course you will.”

I must have looked puzzled.

“If you’ve gone as far as I think you have, and what I saw yesterday tells me you have, you’re not about to stop now. Just tell me this honey.” She paused and looked out the window. “Is it the just the clothes, or is there more?”

I was confused. I didn’t know what she meant and my confusion must have been apparent.

“Mark, honey, do you just like to dress up or do you think you’d be happier as a woman?” I heard her voice catch and I realized that my entire future rested on the next few minutes. I’d heard about one’s life passing before one’s eyes. Now I knew what it meant.

I’m 45 years old and to this day I don’t know why I enjoy wearing women’s clothes. I remember being 5 years old and being fascinated by my sister’s Easter dress. I remember a few years later staring at the girdle ads in the Sears catalog. I remember raiding the laundry hamper to try on my mother’s things. I remember the first time I bought my own clothes, terrified that someone I know would see me. Of course nothing fit right that first time but it didn’t matter. I remember the first time I wore panties to work and how I couldn’t concentrate all day. I remember getting the nerve up to approach a sales woman to tell her that I was a crossdresser who’d never had the opportunity to buy my own clothes and ask her help in getting me sized properly. I remember how her smile and reassurance made me feel absolutely wonderful. I remember the first time a salesperson asked if I wanted a gift box and I said “no thanks, it’s for me.” All these images ran through my mind all at once and none of them had THE ANSWER stamped on them. I just opened my mouth, let my heart do the talking and hoped it would come out right.

“Kathy, darling, I love you more than anyone or anything I’ve ever known and I know that you love me too. I don’t want anything to spoil that, ever. I don’t want to be a woman. I really don’t and I don’t think that’s ever been part of it.” Our eyes met for the first time since that moment yesterday afternoon when she came home.

“…But you’re right, I don’t think I could stop. At any rate, I’m pretty sure I couldn’t stop and not go crazy. I don’t know why I like to dress up, but I do. I know I really like feeling pretty. I love, really love wearing soft, pretty clothes. There’s some part of me that feels completed, fulfilled when I’m dressed in something lovely.

“All I can do is hope you don’t hate me and we can work it out, because I can’t imagine living the rest of my life without you.”

“I’m not going anywhere, honey.” Her smile was warm but there was something in her face that was distant. “I loved you yesterday and I’ll love you tomorrow. I don’t understand this at all, and I don’t understand why you couldn’t share this with me 10 years ago, but I’m not sure that matters. It’s still you and me, honey. I promise.”

We both started to cry and then hugged each other.

Part Two

After a couple of minutes, Kathleen broke away. “I have to get to work,” she said, but I noticed she didn’t look at me as she slid out of the kitchen. A few minutes later she came downstairs in her uniform (white blouse, slim navy skirt, matching navy vest, neutral pantyhose and sensible 1” black pumps — she wore this outfit, sometimes without the vest, sometimes with a navy blazer, every Tuesday through Saturday). She gave me a peck on the cheek and hustled out the door.

That left me figuring out what to do with the rest of the day. What to do with the rest of my life. Everything had changed, but I didn’t know what it had changed to. Yesterday, I would have run right upstairs after Kathleen’s car had left the driveway and rummaged through my closet for something pretty, or maybe I would have gotten in my car and done some shopping. Somehow, though, neither one of those alternatives seemed like the right thing to do. I wound up spending the day puttering around the house in a daze, not doing anything or accomplishing anything and feeling the time wasting away.

When Kathleen came home she called my name before opening the door (which she’d never done before) and when she saw me dressed in boy clothes, I could have sworn I saw disappointment on her face. She gave me a quick kiss and went upstairs to change into jeans and a turtleneck. We made small talk for a bit while I finished preparing dinner and continued talking about things of no consequence all through my Pasta Putanesca.

It wasn’t until she was clearing the table that I felt Kathleen get serious. Her back was turned to me when she said “Honey, there’s just a couple of things I want to get straight.”

I felt my stomach drop. “Here it comes,” I thought to myself. To her, I just said, “OK.”

“I don’t pretend to know what’s going on, but first, I want to know, no I need to know if you still love me. Do you? Do you still love me and want to make love to me and live with me and hold me and grow old with me?” She still wasn’t looking at me.

I didn’t hesitate for a second. “Yes. I do. To all of it.” My mind buzzed with other words, but none of them seemed right.

She turned around and looked at me. Her expression was blank but I could tell her mind wasn’t. She looked at for what seemed like hours, but was really only about thirty seconds. “I love you too honey. Still. And I think we can still make this work.

“But there’s one other thing. This is just between us, right?”

I just looked at her, confused, not understanding what she was saying.

“You’re not dressing up with anyone else, or parading around the streets, or hanging around in bars, or anything like that, are you?”

“God no,” I splurted. I must have looked so shocked she believed me, which was a good thing because I was telling the truth. I mean unless you counted the several women’s clothing stores where I was known as a regular customer, I hadn’t shared this part of me with anybody.

Kathleen looked relieved and almost relaxed. She still seemed a little tentative, but the tension that had stood between us for the last 24 hours seemed to be fading. We watched a little TV (no pun intended), listened to a little music, had a couple glasses of wine. Just before we headed to bed, she turned to me and asked “Do you have a nightie?”

“Umm, yes.”

“Why don’t you put it on tonight. I’ll be upstairs in a bit.”

I did just that. Then I turned off the lights and pulled the covers up tight to my neck and waited for her. She came upstairs in about ten minutes, changed into a sleepshirt and sleep panties (panties that had lost their stretch but were fine for sleeping) and crawled into bed beside me. She started caressing my body through my nylon and lace and soon we were making love like we had the second time we’d ever made love.

The first time we were too eager, too hot, too passionate. It was an explosion that left us weak and exhausted and empty. The second time was the next evening and was far more intimate. That time, we played with each other, slowly and lovingly. We explored each other’s and our own bodies with a loving touch that neither of us had ever felt before and by the time the sun came up the next morning, we knew that we’d be spending the rest of our lives together.

This night was almost like that. It was as if we were both new people and though we knew we weren’t, the experiences all felt new and wonderful. The only difference was that we fell asleep a couple hours after midnight (we are in our 40s, after all!). That, and when I woke up, Kathleen was cuddled in a ball on the edge of her side of the bed, as far away from me as she could get. I couldn’t quite figure out what to make of it all.

That morning was Thanksgiving, and we went to her folks for Thanksgiving dinner and had a wonderful time. When we went to bed, I wore a different nightgown and we again made wonderful love together. In the morning, Kathleen made a point of getting dressed and going downstairs ahead of me, which made the task of getting dressed that morning almost momentous. I had permission to wear a wardrobe that I’d kept secret for my entire life, but had no idea what reaction wearing something from that side of closet would bring.

I ended up going right down the middle, sort of. A pair of plain, white, cotton panties. A lacy camisole under a big, blousy poet’s shirt. My regular (i.e., boy’s) jeans. No socks or hose. Penny loafers. I almost trembled when I entered the kitchen, but Kathleen didn’t seem to notice. A peck on the cheek, a cup of coffee and it was as if there was nothing unusual in the world.

That’s how this part of our lives got started and it continued in the same way, more or less. Every once in a while, I’d go a little further but it all seemed so, logical. Soon, I started wearing panties every day and when the novelty of wearing panties wore off it seemed like my wearing panties was the most natural thing in the world. The first time I wore a skirt in front of Kathleen was on a chilly Saturday morning in early December. I came downstairs wearing a long, almost ankle length denim skirt under an Irish fisherman’s sweater and she didn’t blink an eye.

A couple of weeks after that, I took what I thought was a big gamble when I wore the same sweater with a knee length wool plaid skirt, black tights and chunky shoes. It was the first time I’d worn hosiery or women’s shoes in front of Kathleen and the first time I’d worn a skirt that showed off my legs. Again, I entered the kitchen trembling with something between fear and excitement and again, Kathleen didn’t seem fazed at all. “You look cute this morning, honey,” she grinned as she poured my coffee and that was the last notice she paid to what I was wearing.

As the weeks went by, I brought out Martha’s (my alter egos name) wardrobe more and more but the one article I couldn’t bring my self to wear again was a bra. I didn’t need one. Back when my dressing was a secret, I loved wearing bras and I stuffed them with all kinds of things but now that there wasn’t a secret, there was something about putting on a bra that seemed, I don’t know, decadent. I mean, here I was wearing panties and camisoles almost every day, coming home from work and changing from sportcoat and slacks into a blouse and skirt but a bra just didn’t seem right anymore. I had a half-dozen or so in my dresser and my attention was drawn to them everytime I got dressed in the morning but I just couldn’t wear one in front of Kathleen.

Then, one morning, about a week before Christmas, I got dressed in a silk poet’s blouse, denim jumper and tights and headed downstairs. Kathleen already had the paper open and the coffee ready. As she gave me a section of paper, she said, “That’s a really cute outfit, Mark honey, but you’d look a little cuter with something up top.”

I must have looked confused. “Mark, you really need some kind of tits to make an outfit like that work. Don’t you have a bra?”

“Uh, yeah.” I must have blushed a million shades of red. “I just felt a little weird…”

“You’re wearing a jumper and tights, and you’re telling me you’d feel weird wearing a bra?” She smiled. “Don’t be ridiculous.” She put on a schoolteacher’s voice. “Go upstairs and get dressed properly young lady!”

Well, I did, but I still felt a little funny and I certainly wasn’t going to put anything in it. When I came back downstairs she smiled. “That’s a little better. Didn’t you ever put something in it to fill it out?”

“Yesss, sometimes.” I remembered spending hours getting knee-hi’s with bird seed, water balloons and baggies filled with water just right to give me the look I wanted. “I don’t have anything like that anymore. It’s kinda ridiculous, I guess.” I was lying through my teeth.

Those weeks I’d spend some evenings dressed in women’s clothes, and most of the time on weekend mornings I’d dress. If we were going out, I’d change into boy clothes, with panties and sometimes pantyhose or a camisole underneath. Certainly I’d never wear anything that anyone would notice. We’d do our errands on Sundays and go to various stores but neither of us would go near a clothing store or clothing department. The closest we came to acknowledging this new phase of our life in public was in a grocery store. The store had their house brand of pantyhose on sale and Kathleen picked up a half dozen pair for herself. Then she turned to me.

“Do you need any?”

I didn’t. Partly because I still had worn any pantyhose in front of Kathleen (so far, just tights and long skirts — I didn’t want her to see unshaven legs under pantyhose) and partly because I didn’t like cheap pantyhose. But, even though I didn’t, I didn’t think I could let this opportunity pass so I tossed a half dozen in the basket too. She didn’t say anything else until we neared the checkout when she grinned at me and said “I wonder if the cashier will notice these are two different sizes?”

Our life was proceeding normally (well, as normally as a gradually de-closeting crossdresser’s life could be). There were occasional moments of weirdness. While watching Monty Python one night, the “Lumberjack Sketch” came on. It used to be one of our favorite bits but that particular night we both sat in awkward silence. I used to do the laundry most of the time and one week I mixed in a couple pairs of my panties with hers. She didn’t notice until one morning she put on a pair and they almost slid of her hips. Kathleen also told me this story of looking in the car’s rearview mirror just before she went to work on Saturday and noticed in a panic that there was a lipstick smear on her cheek. From me. But apart from those incidents we were very, very careful to go too fast or to get ahead of ourselves.

This all ended on Christmas. I’d gotten Kathleen some lovely presents, the kind I’d gotten throughout our marriage. There was a beautiful stained-glass window hanging, a big, luxurious picture book of English gardens, a big, fluffy sweater and some odds & ends. She got me two gift certificates. The first was from one of the plus-size stores in the local mall. The second was from a foundation/lingerie shop in the same mall and where the amount should have been were the words “one pair of breast forms.” I was speechless.

“I really don’t know what you like, honey, so I got you gift certificates. I hope you don’t mind,” she said as she smiled at me.

I leapt across the couch to give her the biggest kiss I could. I couldn’t believe how much courage it took for her to do this. “Kathy, you couldn’t have given me a present that meant more.”

“If you think you could handle it, I’d like to go with you, too. Is that OK?”

“Of course it is. I’d dreamed about this for years, Kathy, for years.”

Christmas fell on a Sunday that year and I had the week between Christmas and New Year’s off, so on Monday we planned on getting my breasts. As I was getting dressed (boy clothes today — khakis and a sport shirt), Kathleen suggested I wear a bra. I was planning on it, but her suggestion was a sweet one. I put on my prettiest bra, which was a 42C and it really didn’t show under my shirt and coat.

We got to the shop and one of the salesladies brought us to a relatively empty part of the store. She showed us the different kind of breast forms (I didn’t know there were different types) and explained the features and prices. She asked if I had a particular size in mind and after determining that I had a bra with me, sent me off to the most isolated dressing room to try them on. Kathleen didn’t accompany me and I was a little disappointed at that. At any rate, I slipped them into my bra and saw how they all looked and I was electrified. Part of it was pure fear — after all, I was a man in a lingerie shop wearing bra and trying out breast forms. But beside that fear was the feeling I was experiencing by seeing MY breasts under my shirt and knowing that Kathleen was behind it.

Then I wondered if she really was behind it or whether she was just humoring me. Off and on for the past month I had agonized over what this really meant to Kathleen and I had moved oh so carefully, following her lead. Buying me breasts seemed like such a bigger step than we had ever taken before and I could not stop thinking about where it was taking us. On the other hand, I just couldn’t explain how wonderful I felt with the weight of my breast forms filling out my bra. It took a while, but I eventually I stopped thinking, made my choice, repacked everything and came out of the dressing room. Kathleen and the saleswoman met me and they took my purchase to the register and did everything that had to be done. I offered to carry the bag but Kathleen made sure that she carried the bag with the shop’s logo when we entered back into the mall.

When we got home, she said “you gonna try ‘em on?” as if it were no big deal. I bounded upstairs with the bag, took out the breasts and slipped them into my bra and then put on the same jumper, blouse & tights outfit she’d teased me about earlier. Kathleen was absolutely right, this outfit did look so much better now. I discreetly tiptoed downstairs and with a soft “Ta Dah” did a ballet leap into the living room. Kathleen didn’t say anything, but she smiled warmly and gave me a big hug and kiss. When our breasts touched, I went electric and tingled all over. And I know that mine were only silicon, but just the same…

When we went to spend the other gift certificate, it went about the same way. We went to the mall and I was dressed in my boy jeans and a polo shirt (although I was wearing panties, pantyhose and a camisole underneath). When we entered the store the saleswomen looked at me a bit quizzically — not because I was a man but because this was the first time they had seen me with anybody. It also could have been a bit confusing for them because Kathleen could have been shopping for herself, as she’s a plus-size herself. I smiled in a way that told them everything was OK and started right towards the skirt rack.

While we were in the store, Kathleen just sort of poked around aimlessly. Occasionally, she’d check the price tags of a T-shirt or a pair of jeans and when I showed her something, she’d comment. We were there for a while but in all that time I didn’t see her really look at anything for herself. I mentioned that a couple of times and she’d reply “I’m not in the mood,” so I decided not to press it.

Eventually, after going through almost every rack in the store (I really wasn’t interested in outerware or sweatpants, so I left them alone) I settled on a couple of outfits that I really loved. I had them rung up and chatted with the sales women for a bit. As we left, Kathleen took the bag as we hit the mall.

Over the next several weeks, my wardrobe grew dramatically as I actually started to develop a style. With the ability to spend an increasing amount of time dressed at home, I started to see what kinds of clothes looked good on me and what didn’t. Kathleen helped out here, too. At first, she expressed approval with everything I wore but I suspect that this had more to do with psychological approval than it did anything with a fashion perspective. After a while, though, she’d notice something that looked off and say “I think that this might look better if you…” or “We don’t really do it that way. You should probably…”

It was one of those comments that led to her giving me my first makeup lesson. It was late February and the first spring dresses were in and I fell in love with a long, almost ankle length yellow floral print. Big bright pink and red flowers were sprayed across the sunny yellow background, the sleeves were gathered into puffs and the shoulders and the neckline was almost a collar style. I loved it and ran right home to try it on. I kept it on (under an apron, of course) as I made dinner, and met Kathleen at the door with a big hug in my new yellow spring dress.

She could tell I was excited but when I stepped back to show it off, all she did was look at me appraisingly and said “That’s very nice, dear. Very nice.” Then she went upstairs to change. During dinner we chatted but I’d catch her looking at me with a funny look every once in a while. As I was clearing the table, she cleared her throat. “Honey,” she said.

“Uh oh,” I thought to myself. She’s having second thoughts. This is all about to come crashing down on me. “Yes,” I replied, as neutrally as possible.

“That is a really pretty dress. I think you look very nice in it, but there’s something off. Turn around and look at me.”

I did. She looked at me for a couple of minutes and I was getting more and more scared.

“Have you ever worn makeup, honey?” she asked, when she finally broke the silence. My jaw must have dropped but nothing came out. “I mean, I look at you and I see a nice body with big boobs under a beautiful dress, but it still doesn’t look right. I think it’s your face. There’s no makeup.”

“I tried a couple of times a long time ago,” I answered, “but I wasn’t very good at it. It always came out looking either sloppy or slutty.”

“We can fix that, hon,” she said brightly. “Change your clothes, we’re going shopping.”

After I changed (I hated getting out of that dress) we drove to the local strip mall. In the parking lot on the way to the drugstore she whispered to me “we’ll just get some basic, inexpensive stuff this time. After you learn what to do, you can get something nicer.”

We went straight to the makeup aisle and she picked up a whole bunch of stuff. I recognized the lipstick, nail polish and mascara, but I’m not sure I knew what everything else was. As she was going through the racks she kept looking at my face and a couple of times, when she knew nobody was watching, she’d hold something up to me and frown thoughtfully. When she had everything she needed, she told me to wait in the car.

A couple of minutes later she plopped down in the seat next to me and said, “Let’s go home. I have a couple of things to show you.”

When we got home, she told me to get dressed (although I’d been dressing in front of her for nearly three months now, she still hadn’t seen me get dressed) so I got into something simple and told her I was ready. She came upstairs and sat me down on the edge of the bed and proceeded to pull everything out of the drugstore bag and explain to me what it was.

Then, piece by piece, she began working on me. She kept up a running commentary on what she was doing as she rubbed, smeared, dusted and drew on me. I kept up with her for a while, but after a few minutes I just began to bask in her attentions. A couple of times she pulled away to look at me, but then she’d start in again and do a couple more things. Finally, she put down the lipliner (the last piece of the puzzle, I guess), picked up a hairbrush, did a couple of passes through my hair and then stepped away from in front of my face so I could see.

I’ve read enough stories to expect that I should have been dazzled by my reflection. I wasn’t dazzled and I wasn’t shocked by how beautiful I was, but I was amazed by how much difference Kathleen had made in my appearance. It was still me, but it was an enhanced me and I really, really liked what I saw. What I saw looking back at me was a woman. A woman with a funny haircut, but a woman. And in this moment, I understood that everything had changed, again.

Part Three

I don’t know why I crossdress. I don’t know what caused me to put on my first pair of panties. At one time, I thought that my fascination with women’s clothes was merely erotic, but after a time I grew out of that and began to realize it was something deeper. I once thought that it was merely practical, that soft fabrics and skirts were more comfortable and more practical than suits. That didn’t explain the bras and pantyhose, but so be it. I once thought that maybe there were two psychological parts to me that were represented by my external wardrobes, but the more I dressed, the more I understood that there were hundreds of different threads running through me and while some seemed more prominent when I was in a dress, some didn’t and they were all part of the same me. The more I dressed and the more I thought about it, the more I discovered about myself.

There was one thing, however, that was consistently a part of me from the very beginning. I was a man and through it all, I never really wanted to be anything else. Being male was as much a part of who I was as my fascination with architecture, my need to be organized (I may have been psychologically as disorganized as hell but you’d never find anything out of place in my file cabinets or my reference shelves), my need to dress in women’s clothes and my love for Kathleen.

I may have wanted to look and feel like a woman, but I never wanted to be a woman.

And now, looking back at me from my bedroom mirror, was a woman. I was more confused than I had ever been in my entire life.

I think the same thing may have been true with Kathleen, or maybe my reaction was upsetting her a little.

“Like it?” she asked, her voice trembling and her face utterly without expression. “I kept it pretty simple, so you can probably do the same thing yourself next time. The important thing …”

I lost track of her voice as I continued to look into the face in the mirror. I wasn’t entirely sure of what I was seeing. Kathleen wound down after a bit and her silence became loud enough to hear.

“Honey, I don’t know what to say,” I finally managed. “I’ve seen you made up a thousand times but I didn’t know it could make this much of a difference. I look so, different.”

“Now you know all our little secrets, honey.” She was trying to be flip, but she sounded anything but genuine. I don’t know what I heard in her voice, but there was a little fear, a little anger, some disappointment and a lot of confusion in what I heard. I heard all that, but I wasn’t listening. It was like background noise to me as I was far too consumed with trying to cope with what I saw and what I felt. And I knew that it was more important than ever that I come to grips with “this,” whatever “this” was.

Eventually, my heart resumed it’s normal rhythm and we spent the rest of the day doing what we normally did on days that Martha appeared, which was to talk and putter around the house and watch a video or two and not do much of anything constructive. Beneath that calm, my mind was churning and in retrospect, I’m sure Kathleen’s was too although we both did our damnedest to pretend that there was nothing out of the ordinary. We made love that night, but it felt very mechanical to me, as if I was watching myself get excited and I programmed this body of mine to do what it had to. When I came, I was early and spurted all over my nightie. I apologized in a sort of perfunctory way and then rolled over and went to sleep.

A few days later, for no particular reason other than it seemed right, I shaved my legs and armpits. Kathleen smiled when she saw my now-smooth legs under pantyhose for the first time (I hadn’t dared before, preferring tights, long skirts and pants) but she didn’t saw anything. A couple of days after than I shaved my chest and within days after that bleached the hair on my arms. I couldn’t reach my back but I did the best I could, under the circumstances.

My life was becoming ritualized and I felt almost powerless to stop it. I was now wearing panties every day, which was no big deal. I’d come home from work almost immediately after the school day ended which was a change because I used to spend lots of extra time with any kids who wanted to use the library in the afternoon. As soon as I hit the door I’d be taking off my male clothes. I’d almost race to the bedroom to get a bra so I could put on my breasts. Then I’d spent an inordinate amount of time in front of Kathleen’s mirror putting on makeup before selecting a dress or skirt/top combination. I’d started buying lots of jewelry and would add whatever I thought worked with my outfit and only after I was utterly satisfied that I looked absolutely lovely would I go downstairs to begin dinner.

I always got home before Kathleen and I loved to cook so making dinner was never a big thing but I was spending so much time in front of the mirror that I often didn’t get to begin dinner until just before she came in the door. This meant that we were eating a lot of hamburgers, grilled chicken and salads. Not that I did a bad job on any of these, but they were quick and they didn’t get in the way of my fantasy world.

Since we first were married, dinnertime was special for us. I don’t know why, but food and good conversation seemed as intimately connected as we were ourselves. It didn’t matter whether dinner was something I’d prepared after coming home from work, or maybe one of Kathleen’s specialties on the weekend or take out pizza or even an evening out in a restaurant, but this was the time where we talked about what was happening in our lives. Now, though, even that was changing because I was just so bursting with new energy and new experiences that dinner was becoming a monologue. We might talk about something that happened at work (either hers or mine) but sooner or later I’d bring the conversation around to something I did for the first time dressed en femme or some feeling I’d experienced for the first time. One part of me rationalized all this Martha’s introduction to the world but all parts of me failed to recognize that to Kathleen, it was all Mark and Mark was not only monopolizing what had been their special time but he was ignoring Kathleen for Martha. Not only was I beginning to push Kathleen into the background during dinner, but my continuing fascination with Martha’s coming out began to push dinner itself into the background. I never noticed. Kathleen was saddened, and I didn’t notice that, either. It also meant that we didn’t eat out as much as we had, because I insisted on spending as much time as I could as Martha and neither of us could imagine Martha in a restaurant.

Martha was also beginning to put a financial strain on us. As Mark, I never was much of a clotheshorse but I’d always been presentable. Kathleen never spent much on clothes, either, which was fortunate. We both spent lots of money on books, food, music (I’m a jazzaholic, Kathleen a confirmed world music explorer and we both share a love of classical music and Anglo/Celtic folk music) and decorative art. We’ve never been poor, but we’ve also never been more than a paycheck or two beyond the mortgage. Now, with Martha spending every Saturday shopping for clothes and jewelry and experimenting while developing a style of her own, we added an entirely new category of expense we’d never had before. The first time we’d ever bounced a check was that spring when I’d miscalculated how much money we had in the bank and the water & sewer bill didn’t clear. It was written the same day that I paid my credit card $500, which was about half the total (I used to pay my bill in full but we couldn’t afford to do that anymore) I’d racked up on clothes and accessories for Martha in the past three months.

It’s easy to see now, but back then I couldn’t tell that my life was spiraling out of control. I was out of control. This idea of being Martha had taken control of me and while I was still extremely careful outside the house, Mark had pretty much ceased to exist once I got home.

And this was not good. Not at all.

The first tear in the fabric came on a warm night in early May. School wasn’t out yet, but it was winding down. I came home from work a little early, changed into some particularly lovely lingerie and a rayon robe before putting on breasts and makeup. I was absolutely meticulous with my makeup that afternoon and mentally congratulated myself on how beautiful I looked, then slipped into what you would have called a little black dress if it were black and not turquoise, faux pearls and black pumps. I was sophisticated and lovely and late for dinner.

I didn’t even notice that Kathleen had come home and as I dashed by the den on the way to the kitchen. I said hello, blew her a kiss and said breezily “Sorry about not getting dinner started hon. I’ll just whip up something in a jiffy and we’ll be all set.”

“Don’t bother,” Kathleen replied. “I had a big lunch. I’m not real hungry anyway.”

I looked at her. “Are you OK, honey?” I asked.

She didn’t respond for a few moments. Then she looked up at me. “Dear,” she said, “I don’t think you’re playing this role all that terribly accurately. Most women who come home from work take the dress off, wash away the makeup and kick the pumps into the closet.”

She gave a big theatrical sigh and settled a little deeper into the couch. “You might be working just a little too hard at this.”

I was shocked into silence. My brain started spinning in circles, not sure if I should apologize, whip off a witty bon mot, a psychological explanation or begin an argument. The apology seemed like a pretty good bet, although I didn’t have a clue as to why.

“Honey, I’m sorry. I just…”

“No you’re not, dear.” She smiled at me, but the smile looked tired and far too deliberate. “You’re not sorry. You just think that that’s the right thing to say, but it isn’t. It really isn’t.”

I knew it wasn’t but I didn’t know what else to do. I desperately tried to think of something to say but nothing coming from my brain seemed to connect with my tongue, so I remained speechless.

“I know how important this must be to you, dear, but it just isn’t working for me. I’m trying incredibly hard to imagine myself in your mind, but I just can’t do it. I can’t imagine myself coming home from work and willingly putting on a girdle and pantyhose. I can’t. I can’t imagine why anyone in the world would want to wear high heels if they didn’t have to.

“And then my imagination starts to run wild. What are those heels and that dress doing for you? What need are they filling for you that I don’t? Or can’t?” Her voice was gradually rising in pitch and intensity. Then her voice dropped and she looked at me directly.

“Or do they replace me? If you can look like the woman of your dreams yourself, what do you need me for?”

“Kathy, you can’t begin…”

“SHUT THE FUCK UP,” she screamed at me. I was stunned.

“Just…shut…up.” She was quieter now. “I love you Mark, I really do. But I don’t know who Mark is anymore. I don’t even know if you still exist. You are confusing the hell out of me. I know I’m not a lesbian but for months every time I make love I’m making love to someone in a nightgown and lipstick. I wake up in the morning and watch you get out of bed and put on a pair of fucking panties. I come home at night and get a peck on the cheek from someone wearing a dress who has bigger boobs than me. What does that make me?” She was beginning to sob. “What the hell does that make me?”

I started to sit down next to her but she pulled away. “Don’t,” she said. “Don’t touch me.”

For almost five minutes we stood still in awkward, painful silence. Kathleen, huddled in a corner of the couch, trying desperately not to cry as she hugged herself, staring into space. Me, dressed for a cocktail party, staring at her, not daring to move.

Finally, Kathy pulled herself up. “I’m going to bed.” She shook her head a couple of times and then headed upstairs without looking at me.
That night I slept on the couch rolled up in an afghan. When Kathy came down in the morning, I bolted upstairs to take a shower, get rid of my makeup and grab a robe (my male robe) before coming down to make breakfast. Kathy and I were civil to each other and then she left for work and I got dressed for work right after. That evening, we were polite and civil and nobody said a work about our flare-up the night before.

And that’s how it went. On the surfaces, our lives had returned to what they used to be. We went back to all our old habits and rituals and we smiled and were polite and life went on. At first, I stopped dressing completely, but it wasn’t long before I found an excuse (to myself, anyway) to wear panties instead of jockey shorts to work one day, and then another and so on. I never let Kathy see me dressed anymore, but I found occasions to dress anyway, just like I used to.

There were a couple of moments here and there. There was the time I hadn’t finished putting away the laundry when Kathy came upstairs. She saw me folding and putting away panties that obviously weren’t hers, but she went on as if there was nothing out of the ordinary. One afternoon, too, I was feeling particularly guilty about the state of our marriage and loaded (almost) all of my clothes into three or four big Hefty bags and was hauling them down to the car to bring to Goodwill. Kathy walked into the garage just as I was getting ready to put the last bag in the trunk. She asked what I was doing and I told her.

“I wish you wouldn’t,” she said and went into the kitchen. I left those clothes in the car’s trunk for almost two weeks before hauling them back upstairs and putting them away. Again.

Several months went by like this. Spring faded into summer, summer into fall. The coolness between Kathy and I gradually dissipated but I can’t say it was replaced by anything warm. I wanted desperately to move the clock back a year, for Martha to never have left the closet but we both knew that wouldn’t happen and I didn’t know what to do about it. Kathy seemed to have built a cast-iron box around that part of our marriage and while she was obviously and laboriously carrying that box around, she refused to even see that it was there.

Until one day in late October. It was one of those beautifully sunny fall days that occurs all too rarely. Most of the leaves had already fallen and the sunshine just poured through the bare branches to flood the still green grass. I was puttering around the kitchen, brewing a second pot of coffee and doing a little cleaning while Kathy was sitting at the kitchen table pretending to read the paper and letting her coffee get cold. I was putting away the dishes from the dishwasher when I felt her eyes following me around the room. I tried to ignore the feeling for a bit, but I couldn’t. I just turned around and looked at her.

“Yes?” I smiled, but it wasn’t a confident smile.

“This isn’t working, is it?” She was staring at me but I could tell that she wasn’t even looking at me. I was getting a little unnerved. I must have looked bewildered.

“This isn’t working. You, me, your ‘other’ self, any of it.” Finally she broke eye contact. “We are working way too hard to pretend this is a couple of years ago and I never saw you in a dress and you never made love to me in a nightie. I never bought your tits.” Her voice was getting quieter but her eyes were filling with tears.

“No, I never doubted your masculinity,” she almost whispered, with the sarcasm fairly dripping from her tongue. “I never doubted that you were a man and I never doubted that I was all woman for making love to a ‘man’ who was wearing lingerie that was prettier and sexier than anything I owned.”

“Goddamn it,” she said, her voice beginning to rise. “I was married to you for 16 years. I thought I could deal with a husband who occasionally wanted to explore a little but I couldn’t. I couldn’t.” She stared at me again. I was frozen stiff. “I couldn’t.” She started to sob. “Believe it or not, I could handle seeing you in a dress. I really could. I think I know what it means to you and I love you and I need you to be happy. The first time we kissed and you were wearing lipstick I thought it was the sexiest thing.” She giggled through the tears.

“But what I couldn’t take was what this was saying about me. Did this mean I was a lesbian? I don’t want to be a lesbian. I mean, I am who I am and I don’t exactly relish the idea that all of a sudden at 42 I’m supposed to accept that the love of my life has bigger tits and nicer hair than I do? I know they’re fake and I know the plumbing’s still right but now I’m supposed to tell my brain to start fantasizing about, I don’t know, Cindy Crawford instead of Clint Eastwood?”

I felt like I needed to say something, anything, but I also knew that to open my mouth right now would be a mistake. A Serious Mistake.

“But you know what got the most?” She continued. “I couldn’t look at you and see you being a better woman than me.” Her sobs became louder. “I couldn’t stand you being prettier than me.” At this, she completely broke down. “I was never a very pretty girl. I was always too fat. I spent too much time reading and not enough time talking about boys and makeup. I didn’t look anything like the girls in the ads in Seventeen and I knew I never ever would.

“So I never even tried. I read books. I talked with adults. I only bought clothes when I had to and everything I bought was navy or white so I never had to worry about how it would match. I only would think about things that were important. And I carved out my life that way.
“Then I met you and we fell in love and I knew that everything I had been doing was right. You were absolutely the right man for me and I felt it in my bones and I knew that everything I thought about high school that was stupid really was stupid.” She has quieted down a little by now and for the first time since this outburst, she was looking directly at me.

“Then I see you in a dress. And at first, like I always do, I intellectualize it. I go read about crossdressing. I do the research. I try to put myself in your brain and I try to understand. And we talk about it and I tell you it’s OK with me and I even help you out and try to share this with you.

“And then one night all my defenses just fell apart. I couldn’t help it, honey, I just couldn’t. You just looked better than I ever had in my entire life. Your clothes looked beautiful together and on you. You had just finished your makeup and were looking at yourself in the mirror and I went crazy with jealousy because you obviously loved the way you looked and I always hate the way I look. And not only that, but I thought you looked like one of those women in the fashion ads too. You really did look great. And I’m standing out of sight gazing at you and my hair looks like a rat’s nest, I’m not wearing makeup, my blouse is wrinkled and has sweatstains under the pits, I have on one of my seven knee length navy skirts and I’m wearing my grandmother’s shoes. And for a second, I hated you and then I hated myself for hating you and then I got so confused I fell apart.

“What are we going to do, honey?” She was spent. There were no tears left and precious few words. “What are we going to do.?”

I pulled up a chair next to her and hugged her tight. “I don’t know Kathy. All I know right now is that I love you more than I’ve ever loved you or anyone else before. Beyond that I don’t know…I don’t know.”

I was wrong about the tears.

Part Four

Eventually, we both cried ourselves out and talked our way through the rest of the night. We both apologized for things we did and things we didn’t. We talked about things that were silly and things that were serious, but we never talked about my desire to dress in women’s clothes. As the sun came up I knew that we were both committed to making this marriage work and that neither of us had the foggiest idea of how to do it.

Kathy broke our embrace and said she was going to try to get a little sleep. On her way out the kitchen, I blurted “If you want, I’ll promise I’ll never dress again.” I don’t know if I could have backed that up, but I meant it.

“I don’t want that, honey,” And she went upstairs to bed.

I puttered around the kitchen for a while, cleaning up and then stepped out on the porch with a bottle of chilled Chardonnay and a handful of Miles Davis CDs. I know it was 7am, but I figure that since I hadn’t been to bed the rule against drinking before noon didn’t apply. As I sipped the wine and listened to the muted tones of Davis’ trumpet, the chaos whirling around my mind began to settle into patterns. By the time “All Blues” rolled around (the fourth disc on the changer) I knew what I wanted to do and I allowed myself to fall asleep, the morning sun shining on my face, but not shining any brighter than my smile.

The next Sunday, I slept in a little later than usual so Kathy got up before me. After she went downstairs, I showered and shaved (beard, legs and pits) and got dressed — panties and chemise under Gloria Vanderbilt jeans and a sea green polo shirt that L.L. Bean sold only in women’s sizes. I put on boat shoes with no socks and went downstairs, getting ready to appear dressed in women’s clothes in front of Kathy for the first time in months. The only thing was that unless you knew the signature Gloria Vanderbilt stitching on my butt and you looked closely enough to notice that the three buttons on my shirt buttoned the “wrong” way, I don’t think anyone could have noticed.

I poured myself a cup of coffee and popped a couple of English muffins in the toaster and grabbed a part of the paper that Kathy had finished. We made small talk for a while and lapsed into a comfortable silence.

“Do you trust me?” I asked her out of the clear blue sky.

“What? Of course I do.” She looked confused.

“I mean, do you trust me enough to try an experiment, no questions asked?”

“Sure. Yes.” She paused. “You know I do.”

“OK then, it’s settled.” I slammed my coffee cup down on the table like a judge pounding a gavel. “Let’s go.”

“Where?”

“You’ll see,” and I swept the dishes into the sink, threw the papers into the trash (no recycling for this impulsive fool!) grabbed the car keys and held the door open for Kathy. “After you, my sweet.”

Kathy reached for her purse and I knocked it away. “You won’t need that,” I said smartly.

“I’m not going anywhere looking like this,” and I could see her point. She was dressed in a very faded, formerly white Cape Cod sweatshirt, faded navy sweatpants and grayish Keds, but that’s what she always wore on Sunday mornings so I guess I didn’t notice.

“You look just fine dear,” I lied.

“And I haven’t even brushed my hair!”

“You can do that in the car. Let’s go.”

She huffed and began to sit down. “You said you trusted me…”

Having played the trump card, she glowered at me (but I did detect a hint of a smile) and stomped out to the car.

There are four malls in our area. One is anchored by supermarket on the southern edge of town and has a liquor store, dry cleaner and a couple of specialty stores. Another is across the street from a WalMart and has a couple of discount stores, a hardware store, a drug store and a bank. I hardly ever went to those two. The other two malls are on opposite corners of the intersection of the interstate and the turnpike on the eastern edge of town. Those were the big malls. That’s the direction we headed.

We stopped first at the large, enclosed mall. As we headed from the car to the mall, I slid my hand across her back. “Oh good,” I said. “You’re not wearing a bra.”

The look she gave me could have penetrated a two by four at four hundred paces. I just giggled silently.

Our first stop was at Under It All, a store that specialized in foundation garments, swimwear, lingerie, and so on. As we entered, the owner, Loretta, spotted me and waved from across the counter. “Hi Mark, is this Kathy?”

“Yes Loretta and she’s all yours. I don’t think she’s had a properly fitting bra since before we married.” Kathy’s face flushed deeply, but I couldn’t tell whether it was from embarrassment or from being furious at me. “Once you figure out her sized right, I think she’ll need several,” I said to Loretta, as if Kathy wasn’t even there. “A couple with smooth cups for T-shirts, a couple of real pretty ones and some for every day. I’ll look out here for some other things.”

With that, Loretta took Kathy firmly by the elbow and led her to the dressing rooms and I turned to other pursuits. While Loretta and Kathy were occupied, I picked out a half dozen new panties in colors and with trims that Kathy would never have dreamed of picking out for herself. I also picked up a pair of girdles, one long leg and one a regular panty-girdle. I frequently wear a girdle and Kathy and I are only two sizes apart, but my problem is waist and her problems are tummy and thighs. Finally, I added two darling camisoles, one in ivory and one in white.

It took a while, but eventually Kathy emerged from the dressing room with an armload of bras and one set of tags (which meant she was wearing one of her selections). As we were waiting for Linda (one of Loretta’s assistants) to ring up the sale ($285.45, by the way — outrageous!), Kathy whispered in my ear “You were right, but that doesn’t mean that I’m not going to kill you anyway.” Then she saw Linda folding the girdles and placing them in bag. I could almost feel the heat from her glare.

Our next stop was my favorite clothing store, Laura Brown’s. Catherine, the manager, wasn’t working on Sunday but Carmen, the assistant manager was. We greeted each other and I tried to introduce Kathy to Carmen but Kathy was remaining sullenly silent.

I explained to Carmen that Kathy’s employer had a dress code that stipulated navy and white and that Kathy’s wardrobe thus consisted of a bunch of boring straight-line knee-length navy skirts with simple white blouses and maybe a navy vest or two for “variety.” I wanted to get her a couple of outfits that were more stylish and professional, along with a couple of things for the weekend and evenings.

Again, Carmen and I talked as if Kathy weren’t even there and since Kathy refused to do anything but open her eyes wider and wider and she stared at me and blushed, I figured I had no other choice but to keep talking. Carmen steered Kathy around the racks as she talked to me and led us to their career wear section. The first thing she pulled out was a pair of high-waisted, tailored navy pants. She paired this with an ivory rayon blouse with a banded collar and plackets across the breast. After leading Kathy to the dressing cubicle, she picked out a gold chain belt and a matching, collarless jacket to go with the pants.

Kathy was in there a long time and I had to go in after her. I slipped the belt around her waist and put her arms in the jacket (Kathy seemed to be doing a rag-doll imitation) and then almost dragged her out to stand in front of the three-way mirror.

“That looks very sharp on you,” Carmen said. “Very sharp.”

“I’ve always known you looked beautiful,” I whispered in her ear. “I want everybody else to know it too.” I kissed her softly on the neck.

Kathy just stared into the mirror, the anger gone but I wasn’t sure what replaced it. After a minute or so, she started twisting her hips a bit and I could swear I saw her eyes moisten.

“I hope you don’t think we’re finished,” I said to Carmen, as I gently shoved Kathy back towards her cubicle. We were just beginning.

By the time we left, nearly 90 minutes later, Carmen and I had picked out a long, soft navy skirt (matching the jacket) that was nearly ankle length with a muted floral pattern of whites and greys, a dress made of the same material and a slim cut calf-length navy skirt with slits up the side. That skirt made me glad I picked up a girdle for her, and I was sure that eventually, Kathy would see it the same way. We also chose a soft navy cardigan, three white blouses with varying degrees of detailing and three pairs of navy pantyhose and three pairs of black, both of a quality far better than the supermarket stuff Kathy usually bought.

The more she tried on, the more Kathy seemed to relax and when she tried the dress on, I could tell that she was working hard at suppressing a smile. The dress was the last “professional” thing she tried. “That’s enough of this,” she said. Then she amazed us both by grabbing an ankle length, multicolored (it looked like a patchwork quilt, almost) broomstick skirt and trying that on. When she came out, she picked out two more in different patterns and then four solid T-shirts in complementary colors.

Finally, as we headed to the counter to pay, she grabbed a pair of khakis and an olive camp shirt and added them to the pile. “These’ll probably fit. I don’t think I need to try them on.”

As Carmen was ringing up the sale, Kathy took my hand and gave it a squeeze. That gesture alone convinced me I had done the right thing today (and as the bill came to over $600, I needed a little convincing). Right before the amount showed on the register, Kathy returned my kiss on the neck and I was happier than I’d been in months.

Before we left the mall, we also picked up two pairs of new pumps with 1” heels, one in navy and one black, a pair of strappy black sandals with a low heel and a similar pair of flat sandals. Better than your grandmother’s sensible shoes, for sure.

As we left the shoe store, I had to make a couple of changes in our itinerary. Instead of looking around in the big mall, I lead Kathy out to the parking lot where we loaded our purchases into the trunk and headed across the street to M’Lord & M’Lady, a hairdressing salon where I’ve been getting my hair cut for years. It’s a unisex salon and I’ve developed a nice relationship with Tamara and Beth-Anne, the two owners. I’d called ahead to tell them what was going on and after the experiences in Laura Brown’s and Under It All, I don’t know what Kathy expected here. This time, though, I’d told Tamara (who was working this Sunday) that all I wanted was to have Kathy’s hair softened a bit — to have her made prettier without making too many permanent changes. After all, it was one thing to change the clothes, it’s quite another to change the hair. While Tamara was getting her prepped and ready, her manicurist, Kim started working on her nails. It took a while, but when she and Tamara were done and Kathy looked in a mirror, we were both immensely pleased at the subtle, but very noticeable differences.

The drive home seemed to be instantaneous. It’s really about 30 minutes and I know we chatted inanely, but it seemed as if we got home 10 seconds after we left the hair salon. We hustled the bundles into the bedroom and Kathy began to put things away.

I went downstairs, made a big Caesar’s salad (with anchovies) and a couple of gin and tonics and put some Debussy and Ravel in the CD changer. When I went upstairs with the drinks, Kathy was wearing the khakis and camp shirt and the tailored pants hugged every curve of her butt in a most delightful way and I could tell that Kathy loved it as much as I did. I’d never seen her dally in front of a mirror but there she was.

She saw me in the mirror and smiled. “I got a present for you,” and she tossed me a couple of things — one of the broomstick skirts and the black T-shirt. Apparently, when she picked them out, one of the skirts and one of the T’s were in my size. I slid out of my jeans and pulled up the skirt (I loved it, by the way — it was perfect for me) and then pulled off my shirt and replaced it with Kathy’s T-shirt. I stepped back so she could admire me.

She smiled and then rushed forward and hugged me with more passion and strength than any time since we’d been married. The ensuing kiss was delicious beyond words.

Eventually, we took our drinks down to the patio, where we watched the sun set as we ate our salads and talked about nothing at all. We eventually made it to the bedroom, but I have to tell you that the next morning, my skirt, her shirt, her bra and my panties were all found in different rooms.