It All Started In A Bra In New Orleans


It All Started In A Bra In New Orleans

By Ricky

"All the gals are guys" hollered the barker. I was young and naive and didn't quite understand.

It all started when I was young and ignorant of all the possible foibles of mankind

Well, don't most things? After all, when you're old and ignorant, like I am today, you have already done most of your most egregiously dim things already. Well, there are always new even more genuinely stupid things to do, just check the The Darwin Awards if you have any doubts; but, barring Alzheimer's, you're much less likely to do too many more foolish things as you get older.

Anyway, back in the 1982 I was all of twenty-two, single, somewhat sheltered, and a field tech running around the country fixing industrial equipment. No commitments, plenty of spending money, see the world and have fun after a day's work. Back then, there was actually some differences between the big cities. Malls were in their infancy; business was mostly local, the chains had yet to grab every niche they could glom on to. It was fun to go out and explore a new city and find out what was there to amuse a bored road tech who, oddly enough, didn't drink, smoke or gamble.

OK, you're shocked. Get over it, I do have my vices; just not those particular ones, and my preferred pastime was acquired a while later. I have to say I didn't really have any sexy vices so I must have come across as pretty dull and boring at the time. I was a 22 year old boy whose 2 year associates degree had lost some of its luster - what would be called a techie or a geek in a few years.

Mostly I visited local attractions or read a good book in the motel. If I wasn't reading I was writing, I kept a journal just like my English teachers had urged me to do, but until a warm spring evening in New Orleans you would have been bored silly reading it.

That all changed when my company was considering buying a very expensive piece of test equipment and I was picked to visit the supplier in New Orleans to see just what it could do. Even at the tender age of twenty-two I had learned that the glossy tri-fold brochure was no substitute for actually using a piece of equipment to see if the claims were real or some adman's fantasy.

At that point I had been on the road for a good three years; I was used to traveling, living in motels, wandering around strange cities, all that sort of stuff. Just another road trip, even if I was flying this time. Test the product, offer an opinion, and head for home and back to work.

It didn't quite work out like that.

What I didn't consider was this time I was the customer, not the outside expert riding in on his white horse to slay the dragon that had taken up residence in the assembly line. Customers, like dragons, are a whole different species. As the tech I had to defer to the customer, no matter how far from reality their expectations might be, and keep him happy so we would be called back again the next time the dragon awoke. But this time I was the customer - they were determined to defer to me! If I told my boss that the product was a good one, my boss was going to buy a whole bunch of them, making a significant difference to the seller's bottom line.

I'm not about to provide any details about the product, unless you're an electrical engineer or technician the words would be so much gobbledygook, meaningless noises that would overwhelm your brain without leaving you any more informed than you are now. Techies, like trannies, have their own lexicon. Would you attempt to explain some of our jargon to someone who never heard that some men like to dress up as women?

I didn't think so.

You could say I was taken aback when I walked in their front door. The receptionist acted like I was some oriental potentate or something, she practically bowed before me as she led me to the CEO. The CEO beamed and greeted me like his long lost brother returning from a mission to the darkest depths of the Amazon, miraculously alive despite great and perilous adventures. The Chief Engineer soon joined us, enquiring as to my health, (I was twenty-two - of course it was good) my family; (I bunked with mom & dad the few times I was home and they were just fine the last time I saw them); how my journey went, (well, it was my first time on an airplane, so I had something new to talk about); and what did I think of New Orleans? (I hadn't seen much beyond the airport and the drive to their plant in the suburbs.)

The Chief Engineer jovially assured me they would take care of that little oversight that very evening. I was escorted on a tour of the facility, just an introduction as the day was getting late and the serious work would begin in the morning. When we reached one of the labs I was introduced to Josh, a curly haired redhead about my own age, who was poring over the guts of some piece of equipment on his bench and muttering things that I was probably better off not hearing clearly. The Chief Engineer introduced us and told me that Josh would be my guide to the fleshpots of New Orleans that evening.

Yeah, he actually said 'fleshpots.' I had never actually heard the word spoken outside of my Sunday School classes, when 'The Fleshpots of Egypt' were carefully and chastely described and we were strictly warned about venturing anywhere near such dens of iniquity.

I told you I had lived a sheltered life. I hadn't even seen an X-rated film at that time. You'll be relieved to know, I hope, that while I had not witnessed another couple doing the deed, I had participated in a session or two that had most definitely not not been filmed. If you aren't relieved, then I certainly was.

So anyway, the whole fleshpot thing had caused my attention to drift a moment, but I returned to reality as Josh was offering to pick me up at my motel and show me the wonders of Bourbon Street. Now that drew my attention; I would love to see the sights of the legendary avenue and spend an evening listening to hot Dixieland Jazz in the legendary home of the music. I returned to my motel, showered and shaved and excitedly waited for Josh to pick me up.

I really did have to shave - my ethnic heritage endowed me with a very dark and fast growing beard. By five in the afternoon I looked like your typical movie mobster with a foreboding beard shadow. I would have let the thing grow, but back in 1982, a lot of customers didn't trust anyone with a beard. Stupid, I know, but that's the way it was.

The evening was warm and most of the people I had seen on the streets were wearing T-shirts and shorts, so I followed suit. Josh arrived promptly as six, along with his girlfriend Brooke. Now I have nothing against Josh, but Brooke was a whole lot more interesting to look at. A few inches under Josh's six feet and a whole lot rounder in all the right places, her long, black hair and dusky skin made this Northern boy take notice. She was generously endowed, both in figure and bustline, making her a delectable package. Too bad she was taken.

I was a little bit jealous of Josh's car, a nice, almost new Chevy Citation. I had driven a hatchback Nova (what Chevy called the Citation before they changed the name) before I started driving my company van, so I had a nice little nostalgic kick talking to Josh about the car. I didn't even own a car back then, as the company supplied me with a vehicle.

It didn't take long to notice Brooke was getting bored with the car talk, so I asked about where we were going and was treated to a glowing description of a place that served the best seafood this side of anywhere. I've always loved seafood, but until I started my travels and had fresh-caught seafood a few blocks from the port in a few cities, I had no idea of just how good really fresh seafood could be. I figured New Orleans was almost on the Gulf, so it had to have some really good treats in store.

I've forgotten the name of the place where we ate, 1982 was a long time ago, but I still haven't forgotten my first taste of shrimp Creole done right. The peppers, onion and celery were still a little bit crunchy, the sauce seasoned perfectly and just hot enough to let you know you were near Cajun country, and the shrimp popped as you chewed them. I could get used to being a customer and getting the red carpet treatment!

Josh and Brooke turned out to be great fun to be with, smart, funny and just as cynical as me. We agreed the hu-hah over the planets aligning was so much crap, (1982 was just one of many years when the crazies told us it was going to be the End Of The World) agreed the Argentineans were nuts to claim the Falklands, and worried about the crazies in the Middle East invading each other. Sadly, you could change a few names and have much the same conversation today. We agreed the world was going to hell in a handbasket, although how we would all fit into a handbasket was a complete mystery, so we decided to cruise Bourbon Street. Now that was more like it!

We left the car parked where it was and walked a few blocks to the famed home of Jazz - where I was mightily disappointed! The entire street seemed to be composed of rock bars, T-shirt emporiums and girly shows. We walked several blocks and didn't find any Jazz anywhere. Man, the Tourist Bureau ought to be fined or something - talk about false advertising!

Speaking of advertising, every girlie show had a barker outside. We were loudly and clearly informed of the wonders to be had inside each establishment:

"Nude girls! Totally nude! Nothing left! No g-strings! No pasties! Nude, completely nude!"

"C'mon gents! Come inside to see the most beautiful women in the city disrobe for your pleasure! See Carol, with her amazing appendages. Feast your eyes on Luscious Lucy with not a single hair below her eyebrows. They don't start out nude, but they do get there as you watch!"

"We have the most exotic women on the planet for your pleasure! Tall, tawny, titillating, tantalizing. They dance just for you! Feast your eyes on these beauties as they slowly remove those hot and unnecessary clothes before your very eyes!"

Sure, just for me. I may have been a bit sheltered, but I knew it was a lot more interesting to have a woman undress for you if no one else was around. I, for one, would find it hard to get in the mood amongst a crowd of slobbering sex fiends.

Being from Ohio, where the state's patriarchal legislature had only recently been dragged kicking and screaming into the modern world of legal birth control, such displays were rather shocking. After all, it had only been five years since the Supreme Court had legalized birth control for unmarried women. There were a lot of places that wouldn't even sell Playboy, or if they did hid it under the counter and made you feel like a pervert if you asked for it. If there were any strip shows back home, they were in sleazy industrial districts where only the depraved would go, or at least that's what many would have you believe.

So here I was, listening to these blatant come-ons, jostling people and thinking everybody in New Orleans must have been trying to find a vacant spot to stand on Bourbon Street. As we walked together, holding hands to avoid being separated, I began to notice some nasty glances aimed at us. Once again, I must plead a sheltered life - I had no idea people would object to two white men holding the hands of a dark skinned woman. No one threw any bombs or burned any crosses, but there was no doubt that our little trio of skin colors offended not a few people. I was just about to suggest we leave for someplace less crowded when the cry of a barker pierced the air.

"All the girls are guys! Every one of these beautiful ladies are men but you'd never know it. We have the sexiest, the steamiest, the slinkiest she-males on the planet, and they will show you everything they've got! All the girls are guys!"

Before I could make my suggestion Brooke got a strange look on her face. "This I gotta see! I love drag queens - what do they have that I don't have?"

"A prick," Josh replied succinctly. "For which I find myself very glad."

"I don't need one, darling. You can loan me yours whenever the occasion warrants. Let's go in!"

"You OK with that, Jay?" After all, I was the Customer, whose opinion ruled.

"Sure, why not? They don't do this kind of thing in Akron."

Drag Queens? I told you I was a bit sheltered.

"Too damn cold to strip up there!" Brooke replied.

"We do have heaters up in the frozen north, you know."

"I would think all the hot bodies would make such things redundant," chimed in Josh.

With that we entered the Bourbon Pub Parade, a place that is still in business today, believe it or not. Quite frankly, at the time I just didn't believe it. Even though the clientele was clearly on the gay side of things, entering with a beautiful woman on our arms did wonders for finding a table to sit at in the crowded pub. Maybe they figured we were a threesome, maybe they were just being polite to a lady, but in only a few minutes we were seated right by the stage, which was empty for the moment.

Remember, this was in 1982, the whole 'ladies drink white wine at a bar' thing hadn't yet made the scene. We ordered two drafts for Josh and Brooke, an iced tea for me and a basket of chicken wings, a treat that was just starting to be a national craze. Even though we had feasted on seafood only a short time before, the wings disappeared along with the drafts, so we ordered another round just as the lights went down and a bodiless voice introduced the first act. When the spot came up it revealed a passable looking woman in a rather exaggerated outfit, which she mechanically began to remove to a thumping beat and screaming rock music.

As promised, the girl was a guy, and had nothing on by the time he/she was finished. I was rather embarrassed for the poor stripper, who was obviously putting in his/her time and must have done this a thousand times before and was plainly bored with the whole deal. Not so the audience, who cheered and called out lewd remarks with gusto.

I must admit that seeing large breasts on a body with a penis was pretty weird. I was close enough that I could see them clearly, and they looked natural. Not that I've had a great deal of time to study the real thing closely, but I was not a complete novice in playing with a willing woman's breasts.

There were a couple of more acts, all with loud, thumping music and mechanical dance moves that really weren't all that enticing to me. In fact, I rather pitied the poor souls who had to demean themselves for a living. Not my cup of tea.

Once again the bodiless voice spoke from the darkness, introducing "Kissable Kate, the most provocative exotic dancer to ever grace the stage of the Bourbon Pub." To my untutored eye, Kissable Kate certainly lived up to her name. She was swathed in gauzy green froth, had copper red hair that rose serenely above her, sinuous, slim arms that moved with exotic grace and moves that would make a Greek Siren jealous. Unlike her bored and mechanical predecessors, she was magnificent.


It was impossible to think of this feminine wonder as anything other than 'she'. Could the barker have been lying?

"Josh! Put you tongue back in unless you intend to use it," laughed Brooke.

"You interested?"

"What do you have in mind?"

"Something that I couldn't do with Kissable Kate. Later, dear."

"You'd better!"

And what would I do later? I have to admit that my reaction was hardly suitable to lusting after a normal man, but this sure wasn't a normal man! I couldn't help myself, I lusted and drooled along with the rest of the crowd as Kate slowly and sensuously disrobed. No thumping rock music this time, but ethereal harps giving the whole act an otherworldly quality. Kate could dance, and dance well. As she slowly stripped, removing each piece of clothing seemed to be the natural and necessary thing to do; an inevitable consequence of the dance, not the mechanical act expected by the crowd.

She was down to bra and g-string, leaving no doubt that Kate had a small but obvious penis, but the figure and the full boobs were nothing like you find on a man's body. By this time the sight of a cock on a woman's body was almost normal. Well, normal for this place.

Off came her bra, which she flung with casual abandon to land on my head. The crowd loved it, and I had to appreciate the whole thing even if I was blushing bright red. Good thing the stage lighting was rather red so it didn't show too clearly. With a sheepish grin I removed the bra and nodded my appreciation at Kate, who gracefully acknowledged me while continuing her dance. In due time the g-string came off and the act ended, to the thunderous applause of the crowd. The lights went up and the show was over.

"Looks like you got the booby prize, Jay!" Brooke laughed.

"So I did. Tell me, what am I supposed to do with a used bra?"

"Use it?"

"Fling it to someone else if you don't want it." Josh offered.

"Use it? I hardly have the body to do so." At six foot one and 220, the notion was just plain silly.

"Neither did Kissable Kate, but she must have found a doctor to fix that." Brooke grinned.

"Oh boy did she!" Josh leered.

"Down boy! You'll get your treats later."

"Woof! Pant! Slobber!"

Before the conversation could go further downhill, I felt a soft hand caress my neck.

"Looks like you're tonight's victim. You enjoy your little present?"

It was Kissable Kate, enveloped in an almost modest green dressing gown. Not strangely, I found myself speechless. My early childhood training kicked in and I stood to greet the lady (give me a break here!). Up close and personal she was much smaller than her robust stage presence - she barely came up to my shoulder. If I hadn't just seen her naked I would never have guessed this delectable package was anything but all girl.

"Having fun, big boy? You look a bit out of your element."

"You might say that…"

"Well I might. I've seen these two jokers in here before. They delight in introducing strangers to the drag scene."

"Do they now…" Brooke had the grace to look a little sheepish.

"They do. Brookie and I go back a ways. She's a troublemaker of the first water."

"So it seems. It's been an educational experience, I'll grant, but…"

"C'mon, Jay. You were drooling with the best of them. Don't deny it!"

"Guilty as charged, your honor!"

"Sorry - Jay is it? - but we don't allow guilt on the premises. Good fun, a little titillation, a lot of skin and lots of booze. Drink up, folks, it keeps the management happy."

I raised my glass of tea. "Then a health to you and your crew, long may they dance! I know a wholesaler who can supply you with bras by the gross for flinging."

"Already got one. Keep it, bucko, it's part of the show."

"I'll treasure it always."

"Wear it in good health. Come back and see me sometime…"

With that, Kissable Kate went to schmooze with other customers and we decided to leave. Tomorrow was a workday and I had come down here to test their equipment, not meet strange women. Very strange women!

I settled in at the motel, but I dreamed of Kissable Kate for much of the night. Just how did she manage to look like that? Surgery, of course, but… I eventually drifted off to sleep again, my mind spinning.


The tests went well, and my boss was pleased that I gave the equipment my seal of approval. We got done early, so I returned to my motel room and took a nap. I was awakened by the phone, my boss was calling to tell me my next call was in New York City. He assured me I wouldn't need much more than basic tools, since my van was back in Ohio, and I could do the work and be home in the next day or two.
Yeah, sure! Never believe the boss - or anyone else! - when they tell you they have a simple job for you. The immediate problem was I had only one more day's clean clothes, so I changed into my next day's clothes and spent an hour or two in the Laundromat. I don't know why I did it, but I threw Kissable Kate's bra in with my underwear, which left me with a freshly washed bra staring me in the face when I packed my clothes for departure for the next morning.

So, you have probably guessed I had to try it on; it wouldn't be much of a crossdressing story if I didn't, what? Sadly, I'm a big guy and Kate was considerably smaller, no way it was going to fit. I filed the whole episode in the great ideas that didn't work file and went to sleep.


For once the boss was right, the job did turn out to be simple, but fate wasn't done with me yet. A big installation in New Jersey came through that day, and guess who got elected to head up the job, being a couple of hour's drive away? Me, of course. So I piled into my rented Honda and made my way to Jersey.

If you haven't been to New Jersey, chances are you think refineries, pipelines and dirty industry. I'll forgive you, that's what so many movies and TV shows present as New Jersey. The truth is there's a whole lot of green and open space in the state once you get away from the New York City area, and that's where I ended up. In a suburban town that shall remain nameless, we were installing a large electronic monitoring system. (For you acronym geeks that's a SCADA system. Supervisory Control And Data Acquisition.) This involved miles of wires and great gobs of sensors for temperature, pressure and the like, as well as cameras and control panels. I really like installation jobs, they are fun and you aren't under the gun to get the damn assembly line running because they're losing umpty-million dollars every hour the thing is down.

The problem was my van was back in Ohio, as were my clothes. I was only supposed to be gone for a couple of days, but Mr Murphy is always ready to throw his two cents in. The cost of flying me back to Ohio from New York City at short notice was considerable; so the company sprung for a week's worth of work clothes and underwear rather than fly me home. One of the other techs assigned to the job would bring my truck next week, meanwhile I could survey the job, count the inventory to see that it was all still there and do the preliminary work.

So I settled into yet another motel and went downtown to the department store there.

Ah, 1982! Walmart was still a small Midwest chain, Two Guys had just declared bankruptcy and big box stores were not really part of the retail scene in any big way. I rode up to the third floor and found the work clothes section. The helpful clerk insisted on measuring me to be sure I got the right size, even if I already knew it; you just don't get such personal service any more in the big box stores these days. With my sizes newly in mind I bought what I needed for a week or so, but on my way out I passed a great, honking sign:


Buy one - Get one FREE!

Really? A great deal, but what did I need with a bra? Hell, I already had one in my suitcase.

But it didn't fit.

And I knew my chest size, didn't I? I had yet to learn about the sizes of women's clothing and their frequent and astounding discrepancy from what should have been properly described technical specs.

It was fortunate this particular department store was rather conservative. In the early eighties ordinary women were just starting to demand sexy lingerie; the plain, white, utilitarian bra was about to become passé. It was my good luck the sign was above a rack of boxes of simple, white bras - I'm not sure what I would have done if I had to choose color, lace and all that sort of thing instead of finding a box that had the right number on it. Well, two boxes - I wasn't going to turn the sale down.

Naturally, I was rather nervous, but the sales lady simply rang them up with a funny look so I added them to the work clothes in my shopping bag and left the store just like I bought bras for myself every day of the week. My per diem was rather generous, more than covering the bras if I ate cheap, so I had a burger at a drive-in. As opposed to today's drive through, at a drive in you parked your car, ordered and a young lady brought your meal out to you and you ate it in your car while sitting there.

My stomach full, I returned to the motel and rather sheepishly tried the bra on. It took some fooling around with the straps, but the thing fit, and it actually felt comfortable. I didn't really want to do it, but eventually I had to look in the mirror. The slightly naughty, slightly feminine feeling vanished as the mirror revealed a gorilla with a buzz cut in a bra.

OK, I'm a hairy bugger, maybe not actually gorilla class, but my arms, legs and face are adorned with thick, dark hair. Blame my Sicilian ancestors, but up until that moment I really didn't care how much hair my body possessed. There was no way around it - I looked just plain silly.

Like any good problem solver, I had a solution: I closed my eyes. The damn bra felt strange but - , surprisingly somehow - good. Lacking any other ideas, I put on my pajamas and spent the rest of the night reading. It was interesting, I would even say pleasant, to emerge from my reading and feel the bra caressing my body. How must Kate feel with real breasts to fill her bra? Pretty weird stuff to be thinking about, but I was surprised at how natural it felt to wear a bra. When I got interested in something I completely forgot about the bra, but when my attention wandered it was an oddly pleasant experience, so I kept it on when I turned out the lights.


And so it went; after a day of getting dirty on the job I came back, showered and shaved and put my bra on my clean body and lounged around the motel room for the evening. Not that shaving helped much, I have a heavy, dark beard and no amount of shaving would give me that rosy-cheeked glow Kate had displayed, let alone her body. I kept thinking vaguely of how Kate must have felt when she discovered how good it was to wear women's clothes. Except the only women's clothes I had were three bras, one of which didn't fit.

We didn't work Sunday, so I spent a few hours in the Laundromat washing the week's clothes - naturally including my bras. It was fortunate that I had idly read the care label one evening when I was bored - I had no idea that you shouldn't put your bra in the dryer. That presented a problem for me, as I had to wait for the rest of my clothes to dry before I could take my wet bras home to the motel room. They didn't seem to take offense at being wet for an hour or so before I could hang them up to dry, however.

Laundry done, I had time to kill, so I found myself once more downtown at the department store and in the ladies wear section. Since I was wearing my bra to sleep in, I had decided a nightgown was a reasonable thing to add to my collection.

Reasonable, you ask? How could a gorilla wearing a bra and a nightgown be reasonable? I guess you haven't been following politics lately if you can ask that question. I have to contend that a guy wearing a bra and nightgown to bed is pretty reasonable compared to what has been happening in politics lately. Perhaps I'm recalling these events in an attempt to escape the current reality? I'm pretty sure I use dressing up to escape from the crap I face in real life, that makes crossdressing seem pretty reasonable to me.

What was unreasonable was how hard it was to find a nightgown that would fit me. In 1982, retailers were just beginning to realize that there were a lot of American women who didn't wear a size six and look like a model. If you were lucky you could find some larger clothes in the women's section, but they were inevitably in dark colors or - shudder - silver print on black fabric. The larger clothes section - plus size was not yet a popular euphemism - was the fashion equivalent of a small table by the kitchen door in a restaurant; crammed in the back under bad lighting.

The color scheme was a bit better in the nightwear department - I guess the fashion mavens thought black was just too slinky for a large woman to wear in bed - so they were forced to use something more colorful. I wish I still had that nightgown, it stands as a beacon in my mind, the point where I realized that wearing women's clothes was something I wanted to do. It was pink with a blue ribbon below the bust and lace on the neckline and sleeves. It was a satiny nylon, a fabric I had never had much contact with, and felt wonderful! That first night it made it rather hard to fall asleep, but when I woke in the morning I was once again very aware of what I was wearing.

When you're doing a major install job you work long hours - ten or twelve hour days are pretty much normal. It doesn't leave much time for relaxing when you finish dinner and get back to the motel, especially when you have to spend half an hour in the shower to remove the grease and grime from your body. I found it very pleasurable to don my feminine finery with my body squeaky clean and lay in bed reading or sometimes watching TV. The room had a color TV, but the two colors seemed to be red and green. I didn't complain much as I seldom watched anything but Star Trek or MASH reruns. 1982 was the last year for Barney Miller and I just sort of gave up on television after it went off the air.

If I wasn't reading or watching TV I would catch sight of myself in the mirror, which rather shattered the illusion I had built up from the feel of the nightgown. I was a big guy; no way I was going to replace Kissing Kate on the stage even if I had the surgery. Boobs that big on my body would have required a wheelbarrow, not a bra. But the interesting feeling of the bra and the differently interesting feeling of the nightdress were beginning to make me want more. I liked the feel of women's clothes compared with the ordinary-ness of my usual man's clothing. I wanted to experiment more.

I had to wonder about that. If I had something to stuff my bra with, would it help the illusion? I tried what I had at hand, socks and underwear and such, but all I got was lumpy boobs that weren't even vaguely convincing. I resolved to give up on getting haircuts, just as I gave up looking in the mirror.

A couple of weeks into the job some snafu happened and the parts we needed for the next stage of the installation didn't arrive on time, so everybody had the weekend off. If you've ever worked construction, you'll know that a weekend off leads to just one thing: booze and broads. The fleshpots of New York City (there's that word again!) were only a short drive away and a dozen or so of us decided to make the pilgrimage.

You might remember that I wasn't a drinker, so why was I going with a bunch of boys determined to get drunk on their asses and try to get lucky? MADD, of course. Mothers Against Drunk Driving had been founded a couple of years before and people were finally becoming aware of the problem. Since I didn't drink, I got dragooned into driving the crew bus so the rest of the boys could get shitfaced drunk and get home safely. The construction company was pretty definite about anybody driving the company vehicle while drunk and nobody wanted to risk their jobs - at least while sober.

So sometime around noon we all bundled into the van and headed for the Big Apple. Sal was familiar with the place, so I followed his directions to some bar whose name I've forgotten. Since I didn't relish spending the rest of the day watching them get drunk we agreed that we would meet up no later than midnight - be there or find your own way home.

I had my own agenda. Even though the Stonewall Riots had happened when I was a kid, I had at least heard of them and knew there was a gay scene in the Big Apple. I wasn't really sure where I was going - I certainly wasn't going to ask Sal where to find a gay bar - so I found Stonewall on a map, paid an arm and a leg to park the van (hint: Don't drive in New York City if you can avoid it!) and started walking. I was glad my van had arrived from Ohio, I kept one pair of 'civvies' in my traveling suitcase, so I didn't look like a disreputable construction worker for my quest.

It was an interesting afternoon, especially for someone who wasn't all that familiar with the bar scene, let alone the gay bar scene. I spent a bit of time gawking at the scenery before I settled down to seriously finding a gay bar. Really, it wasn't all that hard, even in the late afternoon. My biggest problem was that, as a teetotaler, I couldn't just go up to the bar, order a shot, and casually ask "Is this a gay club?" Turns out it wasn't necessary to be so crass, a good look at the clientele let me know I was walking into a gay bar pretty clearly.

Once again I must plead the ignorance of my sheltered upbringing - I had yet to learn there is a difference between being gay and being a crossdresser. For that matter, the very term 'gay' wasn't very common back then. I was going to learn a lot before the day was over.

So I sat at the bar nursing a Coke, pretending to be waiting for a friend, and listened to the general conversation. I was a bit surprised that there was very little to differentiate it from conversation in any other place that didn't cater to the gay lifestyle. People are people, no matter who they like to find in their bed, I suppose. I moved around to listen to other conversations and it was on my third try - I was going to have a problem sleeping tonight with all that caffeine in my system - when I heard someone mention the drag show at the Pyramid Club on Avenue A.

Move over Sherlock Holmes! I managed to get the information I wanted without getting drunk or mugged in New York City. One of the things I learned that day was how to handle being hit on by another man without getting in some very deep trouble.

I had my doubts when I found the place - it looked like a dive with some very formidable bars over the windows and doors - this certainly wasn't some glitzy club like the Bourbon Pub. What the hell? I had to wait until Midnight to pick up the crew, so I shrugged my shoulders and went on in. It was still early so the place was relatively quiet, but I had found the right place; drag was the order of the day. Or, more accurately, the night. There were even several who, like me, would never be taken for a woman no matter what we wore, but they didn't seem to care - this was their place.

So I went up to the bar and ordered yet another coke - I didn't think the barkeep would be pleased if I asked for water - and sat down at a table. It didn't take long before I had company.

"Want some company, stranger?"

"I'm straight, but if you're still interested sit yourself down." I may not be a drinker, but in my line of work I've seen plenty of women handle come-ons in bars where the rest of the guys liked to hang out.

"Ooooh! One of those!"

Amazing how much sarcasm you can put into one little word like 'Ooooh.'

"An aspiring drag queen, though." I actually thought that you had to be a drag queen if you wanted to wear women's clothes. I had a lot to learn.

"Well, lordie-be! A new guppy in the big puddle. Child, I do believe you have aspirations even bigger than your body."

Why is it that so many drag queens talk like they're from the South even if they're in the Big Apple? Kissable Kate wasn't anywhere near that bad.

"Well, as Oscar Wilde said, 'The only way to get rid of temptation is to yield to it.' "

"Oh my god! A literary guppy that quotes Wilde. How appropriate!"

"Well, I don't intend to go to jail for wearing a dress, but I do admire the man."

"Honey, jail is always a risk if you want to dress up. Not like it used to be, but there are some cops who purely hate us."

"Hey - I'm from Ohio. I know I have to stay indoors if I want to dress up. I just need to learn how."

"We call that 'being in the closet.' I'd recommend a largish walk-in closet in your case."

"Do me a favor, will you?"


"Stick your tongue out."


"Stick your tongue out."

I rather enjoyed her bemused expression, but she stuck her tongue out at me.

"Nope, I was sure it was forked like a snake after that last remark."

"Why you…"

"Careful, darling. A lady of culture wouldn't say what you're about to say."

"Then I have a quote for you, darling. 'Persons appear to us according to the light we throw upon them from our own minds.' Laura Ingalls Wilder. No relation to Wilde, I imagine."

"This poor boy from the sticks hereby acknowledges your erudition and enlightened perception. Can I buy you a drink?"

"Honey child, you said the right words!"

It was an enlightening conversation. Miss Darla, as she styled herself, took me under her wing and just about blew my mind with her matter-of-fact approach to what I soon learned was properly called crossdressing. No guilt for this babe, her attitude boiled down to "If they don't like it, fuck 'em." Then she tittered and said "Excuse me, that wasn't very ladylike," with a wicked grin. By the time I had to leave to pick up the guys my head was spinning with all the information and all the people I had met. But the most important part was the card for Lee's Mardi Gras Boutique that was safely lodged in my wallet.

Arriving at our rendezvous, such thoughts were driven from my mind as I helped load several very sorry specimens into the van, hoping that there wouldn't be any unfortunate reactions to the alcohol that my fellow workers had loaded themselves with. I was damned if I was going to clean up the van if anyone did spew! I'll never understand the urge to get shitfaced drunk and behave like a fool.


I was frustrated after work all week, it was just too late to go the NYC after our long days, so I pulled some strings and told some lies to get Saturday off. Saturday morning passed slowly, if I had learned one thing in my conversations with Miss Darla it was that the drag scene was a nighttime activity. I didn't think the store would be open too early if their customers were sleeping off the night before.

I pored over my maps to locate 400 West 14th Street and set off. I eventually arrived, after numerous wrong turns, in a run-down area that looked more like a warehouse district than one dedicated to retail. After finding a place to park, an adventure in itself, I tried in vain to find the entrance. Turns out the place was in the loft and you had to go up an elevator to find it - an unmarked elevator. The place must have been fairly well known to the locals, because a woman passing by noticed my confusion and told me "If you're looking for Lee's just go up the elevator." It sure looked like a freight elevator to me, but I did as I was told.

I've always compared entering Lees to the point in The Wizard of Oz where the film goes from black-and-white to color. The place was amazing, rack after rack of dresses to fit any occasion and any figure. Bras, panties, girdles, corsets, you-name-it, because I certainly couldn't put a name to some of the exotic undergarments that met my eye.

The customers were just as confusing as the merchandise. At the sales counter was a very old woman - I guessed about eighty - in powder blue short shorts, a magenta top that revealed far too much of what had to be real cleavage and five inch sequined heels. Other than her breasts she had no figure to speak of, and her voice was somewhere in that uncertain range between a normal male and female register. She sounded like she was gargling gravel as she spoke, and her volume was such that no one had to pretend they weren't listening.

Several of the customers were stereotypically gay, several more were men and women who wouldn't attract any particular attention if you met them on the street, and two over in corner had short crew cuts and a posture that just screamed Marines! To this day I don't quite know what I was expecting, but this certainly wasn't it.

My confusion must have shown, soon one of the salespeople came over and asked if he could help me. At least this particular salesperson was dressed in unambiguous male style as long as you ignored the long purple hair. Ignoring it was hard to do in 1982, these days I don't even blink at green or fuchsia or whatever hair.

I managed to stammer out that I was a novice crossdresser (I had learned the correct term from Miss Darla) and needed help in finding all the things I needed to have to try to look like a woman. Not that I was so succinct, but the man must have been used to men like me who were not too sure of what they wanted. I'm sure he was also experienced to recognize a big sale when he saw one.

He gently guided me through the array of bras, breast forms, waist cinchers, gaffs, corsets and all the other undergarments we crossdressers know and love - and real women usually despise. Who else but a crossdresser would subject themselves to being squeezed and stretched for beauty? Oh - just forget I asked that question, will you? Hand me that issue of Cosmo and I'll shut up.

I have to say that my first professional bra fitting was a unique experience. Will - we were soon on a first name basis - suggested an appropriate bra and then went on to describe the kinds of breast forms that would work for me. The selection wasn't as extensive as today's high-tech silicone marvels, but the forms were the right shape, as pliable as a real breast and sure looked real under a sweater. Will didn't even laugh at me when I displayed the results - he was a very good salesman.

I still remember my amazement that the breast forms had real-looking nipples. Back then many women would have been scandalized to have their nipples show through their bra, at least those women who weren't burning them. Look, I worked with a bunch of low-brow guys who were all too ready to watch a naked babe burn her bra, even if bra-burning turned out to be an urban legend.

Before I go any further I need to give you a little aside. I was single, twenty-two, earning good money, on the road ten out of twelve months, had the company buying my meals and paying my rent and providing me with a vehicle. I didn't smoke or drink, two very expensive habits, and more fortunately no drugs of any sort had ever entered my deeply country experience. I had a very tidy savings account. This is important, as the merchandise at Lees was pretty pricy; crossdressers were mostly closeted and didn't want anyone to know what they were doing, so a good businessman could charge a premium for discretion and hard-to-find items.

I left the place with two big bags of just about everything a novice crossdresser could want. I arrived back at the motel about the time the rest of the crew took off to booze it up, leaving me alone to try on my new clothes.

There was only one problem, that damned mirror. I'm a big, hairy guy - not someone who could do a quick change, put on a bra, and go out dancing as a woman with no one noticing. Shaving your legs is a real pain, especially if you're as hairy as I am. I had to change the blade on my razor twice, then I ran out of shaving cream as I carefully shaved my chest, having to finish the job with soap. You don't know what nervous is until you have a blade that damned close to your nipples!

I spent a very entertaining evening trying on all the clothes, becoming breathless in the waist cincher, feeling like a blimp with the padded girdle that gave me some semblance of hips and feeling my wonderful new breast forms bounce in my bra every time I moved.

I tried the gaff, but it was so uncomfortable I soon removed it. After abandoning the gaff I was very happy that Will had steered me away from spandex and other tight fitting garments toward looser, more comfortable fashions. At that young age I still equated 'tight and sexy' with 'feminine,' managing to blithely ignore how my mother and sister dressed. Typical snot-nosed kid, ignoring the good example set by his family.

I learned other lessons that night. Will was right again when he told me that the five inch heels weren't my best choice. Wobbling around on two inch heels, I wondered how anyone could wear some of the sexy shoes I saw at Lee's and still remain vertical. The other lesson was one from Count Dracula: Stay away from mirrors! no matter how good it felt to be dressed as a woman I didn't look like one. My hair was too short and my face too masculine, my beard was too dark. I wondered if Miss Darla could offer me any practical advice, but I just wasn't up to another drive to the city to find out. Besides, I'd have to take off my new clothes if I went out, and I had bought several outfits despite the significant cost.

And despite the experimentation and the lack of knowledge and the strange fit of some of the clothing overall - it was very - er - nice.

When I had finally settled on what I was going to wear I settled back with one of the books on crossdressing I had bought. I was amazed - people had actually written books about men who wore women's clothes. That's where I met Virginia Prince, the grande dame of crossdressing. I had copies of Understanding Cross-Dressing, The Transvestite and His Wife, and Transvestia. I lay on the motel bed, holding the book above my new breasts, reading avidly until I couldn't stay awake any longer. I slept soundly after changing my silicone forms for the much lighter foam ones and putting on a pair of baby-dolls.

In the morning, hunger drove me to remove my finery so I could go out to eat, but I made sure to lay in lunch supplies on the way back and spent the rest of the day reading, changing my outfits every so often just because I wanted to feel what they all felt like.

These days we would call it information overload, but at that point I was desperately trying to absorb all I was learning. I could hardly believe there were enough men like me that there were actually arguments about what to call ourselves, each with subtle (or not so subtle) shades of meaning. Crossdressers, transvestites, transgenderists, she-males, drag queens, en femme/en drab, TS, TG, not to mention several names that never caught on and I just don't remember anymore.

That first weekend, and the weeks to follow, were a magical time. I can't begin to tell you how wonderful it felt to wear those clothes, to indulge in such feminine fantasies. I'm a big guy and I'd never really thought much about my body or the clothes I wore. Being big helped when something on a job was resisting our efforts to move it, the work clothes I usually wore protected me and kept me warm; it was just something that I had come to accept as normal.

But being big conflicted with something that brought me pleasure - and wearing women's clothes was that pleasure. For a time I fantasized about being of a size to be able to pass and have adventures like I read about in the magazines, but eventually I came to enjoy dressing up in private and just enjoy being who I was. Accepting that that person had what many would call perverted tastes took a bit longer, but eventually I realized that if I had to have a compulsion, crossdressing was a pretty decent one.

No, let me rephrase that: it's a damned pleasurable one! A couple of more visits to the Pyramid Club helped immensely, the 'fuck it all - I don't care who thinks I'm outrageous!' attitude of many of its denizens started to rub off on me.

Sometime about mid-week I learned another lesson; when you shave your legs it doesn't take long for the stubble to appear. Stubble is sharp! It grabs the inside of your pants when you bend your knees and is a major pain, and you don't want to think about what happens around your crotch! I soon developed the practice of shaving my legs every other day. I sure hadn't thought of anything like this when I bought that first bra.

It wasn't until I the job was over that I realized I had to find some way to travel with all this stuff in my van. I wanted it all, but it just wouldn't fit and someone was bound to ask questions about all the suitcases. I sure couldn't store this stuff with Mom and Dad when I was traveling! At twenty-two you don't spend much time thinking ahead, so for the next couple of years I ended up renting a small storage locker and agonizing over what I was going to take with me on the next trip.

I also opened a Post Office Box and eagerly sent in my application to the Society for the Second Self. I had found them in my reading and was thrilled to become a part of an actual group of crossdressers. It was frustrating to wait for several weeks before I could get to the box for an answer, and even more frustrating to write a letter to someone interesting on the membership list and have to wait for an answer and then wait some more to get to the PO box. It worked, but I wished there was a better (or at least faster) way.


So life settled into a pattern - work all day, come back to the motel and dress to the nines, sleep and repeat. Every once in a while, when the motel room grew too confining I would wander the stores and buy more clothes or shoes - not that I needed them - but I wanted them! Take a short break at home, try to stuff my storage locker with the older clothes and take the newer ones with me, then off on the road again.

About a year after I discovered crossdressing I went through another life-changing experience: I bought a Radio Shack Model 100. I had been noticing how computers were starting to take over in the industrial control world, not to mention the normal world, and I wanted in. The old Model 100 - I still have it in my basement, it's hard to let go of an old friend - gave me entrance to the world of Bulletin Boards and e-mail, giving me an answer to the agonizing slowness of postal mail. As primitive as the Model 100 was with a small text only screen and 300 baud telephone connection, it was my gateway into meeting others who shared my interest in crossdressing in real time.

Sitting there at my computer I could weave a fantasy about being a beautiful woman, or an international femme fatale or just even just a normal woman who could walk through the streets without comment. Spending so much of my time in out-of-the-way places there was no way I could leave the room - an ordinary stranger would stand out, let alone a large woman with a beard shadow. How do you think I started writing stuff like this? I developed a very rich fantasy life.


1985, my twenty-fifth birthday rolled around. Two days after I celebrated it alone in my motel room with a cupcake, a candle and a new dress, the boss gave me a call; my life was about to change again. When the phone rang I was wearing a cherry red blouse, white lace skirt, four inch heels, half a dozen jangly bracelets and a gold necklace with a stone where my cleavage should have been. His voice abruptly jarred me out of my happy, feminine fog, but by the time he finished offering me a promotion and a substantial raise, I forgave him.

After years on the road the company had noticed and decided I should be the one to take over running the office in upstate New York. That meant a stable lifestyle in one place with only occasional trips out of town. Besides the professional challenge it meant I could have a closet full of clothes instead of a suitcase, and house to run around in instead of a motel room. It also meant I could get that IBM Personal Computer I was lusting after but couldn't get because I had no place to put it. The gods seemed to be smiling upon me.

The next few weeks were certainly hectic; finding a place to live in a strange city, attending training sessions for my new position, turning in the keys for my service van and picking up the keys to my new Ford Mustang. All this was done in the winter, a really stupid time to move. I also found out that no matter how cool the Mustang looks, it's a real pig in the snow. Hey - I was twenty-five and had more money than I knew what to do with, of course I bought a sexy car. The boxes of clothes from my storage room barely fit into the thing, but I got them all across the country and installed in the spare room of my house.

It felt funny to go shopping for male clothes - suits and stuff like that - appropriate to my new position. I found it more than a little ironic that I had to wear a suit to support my feminine personality. What sane person would want to take off a tie in order to put on a waist cincher? Life is strange!

In a continuing irony, I was so busy the first few months that I hardly had time for dressing up at all. Being on salary sounds nice, but it can mean you spend an awful lot of hours on the job, especially if you're new at it. It was early May before I got things under control and started having a personal life again. Having discovered there was a Tri-Ess chapter in town, I finally had enough time to contact them and join the local chapter.

Since the only crossdressers I had actually met were drag queens, I really didn't know what to expect. I had an interview with the membership chair, who was known as Sally, at a nice little coffee shop on the 'artsy strip' of the town. Sally told me she would be wearing a green sweater and black skirt but she needn't have bothered. She was the only woman in the place wearing a skirt. Since I had discovered crossdressing I had realized that women's slacks outnumbered skirts by about ten to one. My own mother didn't wear skirts very often, how was it she ended up with a son who actually wanted to wear skirts?

If Sally was taken aback by the large, hairy man who wanted to join her group she concealed it well; as I was later to find out, many of my sisters were much like me - utterly unable to pass. She greeted me graciously and, in a voice that made me a bit jealous, welcomed me to the group. We talked for close to an hour over coffee and pastries as I talked about how I came to want to dress. She, in turn, told me about the group and want they did and what they expected. Mostly they socialized at member's homes, occasionally there was an outing to a local club that was friendly to crossdressers. Many of the meetings had someone to talk about fashion, makeup or other things our mothers never taught us about being a woman, but mostly they were about just having a place to relax in a skirt. Having a pleasant conversation was high on their agenda.

"Even someone like me who isn't going to fool anyone?" I asked.

"Especially someone like you. The whole idea is to have a welcoming place where you can be all you can be, even if the damned army stole our slogan."

"Well, I've let my hair grow in and sometimes try to think what it would be like to walk around in a skirt with my hair blowing in the wind, but I'm never going to convince anyone I'm female."

"Never say never. We can help in many ways."

"I sure could use some help with makeup. The couple of times I've tried were disasters."

"That part's easy, come to the next meeting and I'm sure you'll find someone to help."

"Don't be too sure about it being easy - I suspect I'll be quite a challenge."

"We all were; just look at it as another way to make friends and find who you really are."

"I've always liked optimists, Sally."


Once again the irony in my life was prominent. In moving to a new city I hadn't had the time to make any new friends in the flurry of a new job and the isolation of winter. Now that things were settling down and the weather was breaking I was making new friends because of my desire to dress as a woman. The advice columnists (one of my other vices) always say to find friends who share a common interest. Go to church, concerts, book clubs - whatever kind of things matter to you in your life. Somehow I don't think Dear Abby would have thought of a crossdresser's club in this context, although in her later years she was very kind to those of us who crossdressed.

That first meeting was stressful. Naturally I went in my normal relaxed male clothes. (I wasn't dumb enough to wear the suit I had to wear for customers!) I really wasn't sure what to expect, but I followed the directions to the house, getting lost only twice because I still wasn't too familiar with the city. It was an otherwise unremarkable suburban place, although it was pretty large. Lots of room for a meeting, I guess. I was greeted at the front door by a casually dressed woman - at least I thought it was a woman. I was still new enough to speculate endlessly.

"You must be Jay, welcome! Come in and meet the gang."

"Thanks, I appreciate you offering your home for this."

"Oh, it's not mine, I just got dragooned into being the greeter. This is Sally and Alice's place. I'm Janice by the way. I'm with Tiana and I'm the GG of the pair."

Well, that mystery was solved. I didn't realize then how rare it was for a crossdresser to have an accepting partner.

"Nice to meet you, and thank you for greeting, then."

"Of course. These meetings tend to be rather free-form sometimes. If you like us you'll probably end up doing all kinds of odd jobs to keep the place running."

"Thanks for the warning. Is there a good hiding place when they start asking?"

"Well, since most of the sisters are still in the closet those closets may all be too full to do you any good."


"This is a support group. If the closet is full enough then nobody can fall down."

"An interesting philosophy. I'm new to this and can use all the support I can get."

"That's why we're here. I think you'll find us an accommodating group. The action is down the hall this way."

There were maybe twenty or so people gathered in the recreation room, I was introduced and promptly forgot half the names - pretty much normal for me in a crowd. They were a well-mixed group in age, demeanor and interests. I was pleased to see several women with my body type in the group, chatting away and seemingly unconcerned that they were obviously men in dresses. There were several who just had to be actual females, GGs as the jargon had it, and several I wasn't sure about. Why is it that we just can't rest until we have identified and categorized anyone we meet as male of female? Genetic? Cultural? Crossdressers should know better, but hey - we're human.

Since I got the promotion I have had to attend several gatherings of people who haven't got a single thing in common except a work connection. They are often strained as you desperately search for something to talk about besides the specs on the latest gizmo. Conversations start and fade off repeatedly until you finally hit something that interests the person you are talking with. Meeting with my sisters was much like those gatherings at first. Oddly enough, what appeared to be the oldest woman in the room and I hit it off.

"Hi, I'm Sonia, welcome to the group."

"Thanks, I'm Jay. This is my first time meeting any of my sisters."

It was still trying to think of these people as 'sisters.' My only sister is fifteen. She was a surprise to my folks, but then having me as a sister would be a considerably bigger surprise to my family.

"Then welcome. Would I be wrong to think you're feeling a little bit out of place?"

"I see you have a gift for understatement."

"At my age you either learn or end up looking like some street person mumbling to themselves over a bottle in a brown paper bag."

"I would find that a hard image to associate with you, Sonia."

"I do a bit of acting, I played that role some years ago and it was great fun. Ratty old cardigan, disreputable skirt, hair knotted and looking like old socks. I loved it!"

"I would have thought Hepburn rather than a street person."

"And you seem to have a gift for flattery! Since I retired I find it harder to resume my former role as Stan than to live my life as Sonia. It's much more satisfying."

Well - that answered that question.

"You play the part well. I just wish I could do so convincingly."

"A challenge, but nothing's impossible. Not a leading lady, but a character actor can have great fun with her role."

"I'd be a character, all right!"

"My father always stressed how essential it was to build character, usually when he had a job for us that we didn't want to do."

"I've shared the experience."

"And there's no reason you couldn't share the experience of letting your feminine side see the light of day, or at least the light of the incandescent bulbs in this room."

"I'll need a bit more work on my presentation before that happens."

"Why, you're in luck, my dear. As our sister you have access to all the help you could need. Some makeup tips, coaching on how to move - the world will not end if you let your feminine self come out among friends."

"Funny you should say that. On the way over I was hearing how the world was going to end. Some preacher in Arkansas is saying that Armageddon will start in Alaska on June 8th."

"I heard the same report on NPR. Arnold Murray, wasn't it? If I remember right he told us the world would end back in '81, too, and he blew it. Not a very good track record, but I don't mind him being wrong about the end of the world. When you hit seventy-three you lose count of how many times the world was going to end. Well, if you want a front row seat, at least June is a good time to visit Alaska. I suppose that as many Eskimo women tend to be of the larger persuasion you might just fit right in."

"I'll pass. Winter here is cold enough for me."

"But it does have its advantages - I used to underdress when the weather got cold and nobody would notice."


"Of course. Panties, bra, stockings - who can tell under a down jacket?"

"I never thought of that!"

"That's what your sisters are for, lots of helpful advice available."

"You ever get caught?"

"Never. People see what they expect to see. Of course I never tried it during the summer when a sweat-soaked shirt would be too revealing.

"I'll have to try that this fall, too bad summer is coming."

"Summer has other advantages, most of them not connected to crossdressing."

"Like no more snow. I suppose it's a good tradeoff."

"It certainly is. Fortunately, I'm long retired and can dress any way I want and not worry about losing my job or such."

"What about your wife?" I had noticed her wedding band.

"That's her over by the fireplace. She still thinks I'm crazy but after fifty-five years she tells me it's too much trouble to trade me in on a new model."

"Wow! I guess twenty-five isn't quite as old as I was thinking on my last birthday. Those landmark years get you to thinking."

"About what?"

"Well, getting married, having kids, what will I do for the rest of my life?"

"So what's stopping you, other than finding a woman who thinks crossdressing is OK?"

"Mostly finding a woman, period. Up until a few months ago I was constantly on the road. I loved it; I'm a bit of a loner, but when you know you won't be staying anywhere very long it makes it hard to form a relationship."

"I suppose so. So what happened to change your wandering ways?"

"A promotion - I'm running the local office for my company and don't have to travel anywhere near as much. That's one reason why I'm here, I'd like to put down some roots and meet people."

"Well, welcome to our little group, but if you're interested in meeting women this may not be the happiest of hunting grounds."

"No kidding! I'm not just hunting for women, I'm working on the loner thing, too. I've been dressing up in motel rooms for a few years now, but if I'm going to be in one place it's good to know people who share my interest."

"Then I won't continue to monopolize you. Let me introduce you to some of your sisters."

We found a group talking about the Removatron, which was supposed to permanently remove hair where you didn't want it - a subject dear to most crossdressers. A couple of my sisters had tried it, but it didn't really work. In fact, the Federal Trade commission had just sued to stop them advertising it as permanent hair removal. I had seen ads for the thing and wondered if it was worth the money - good thing I hadn't bought it!

Rather to my surprise, other than that nobody talked much about crossdressing. It wasn't until much later that I figured out there is only so much to say about it, after years of being a crossdresser you run out of things to say about the subject. What we did talk about was things like how Route 66 had just been declared defunct, much to the dismay of several car fanatics in the group.

Some guy named Gorbachov had just become the leader of Russia and we all speculated on just what that meant. The Terry Anderson kidnapping was in the news, which led to an extended discussion of terrorism and what we should do about it. If any of us had realized just how much the subject would affect us in the future we would have been outraged.

There was plenty of outrage on the subject of New Coke. Now there was a subject I had a strong opinion on, having drunk a whole lot of Coke at bars with the other guys on the job. How could they mess with an American Icon? The new stuff tasted like Pepsi. What were they thinking?

Amazing what you can get excited about, isn't it? Some of the participants were more excited than a Baptist condemning gays and crossdressers. I guess we all have our sore spots.

As the evening came to an end I found myself with Sonia once again.

"I hope you enjoyed the evening, Jay."

"I certainly did. I'll be sure to come again the next time."

"Perhaps you'll be comfortable enough to dress for the occasion?"

"Now that was the $64,000 question!" I fell back on one of my dad's favorite expressions quite naturally. "I don't know if my makeup skills are good enough even for a group like this, Sonia."

"That's no problem, Jay. Come over some weekend and we can help, can't we Amanda?" Her wife had joined us.

"I suppose we could, or we could call in our expert."


"Our granddaughter, who worked her way through college in a salon. She's often willing to lend a hand with our sisters."

"I wouldn't want to be any trouble."

"Nonsense, what are sisters for?"

"I hope you won't ask my sister that - you might not like the answer."

"She doesn't approve?"

"She doesn't know. Actually, we get along pretty well, but she's only fifteen - she was a surprise to all of us."

"And you don't want to be a surprise to her, I gather?"

"Or anyone else - it took a long time to get the nerve to come here."

"You and everyone else here, Jay. Crossdressing is still something that most people don't understand, and what they don't understand they fear."

"Well, I don't understand it, but thankfully the only fear on my part is getting caught, which is not really a problem since I live alone."

"No romantic interests?" Amanda asked.

"Nope - until a short time ago I was on the road most of the time and there was no opportunity to develop a relationship. Maybe now I'm stationary I can do something about that and make my mother happy."

"Looking for grandchildren, eh?"

"Well, not that blatant, but she was very pleased that I was going to 'settle down.' "

"Be careful what you reveal around Amanda; she's a dedicated matchmaker."


"It's true! Now we happen to have this granddaughter..."

"Don't listen to her, Jay! If there's a matchmaker in the family I'm married to her. And our granddaughter is not going to be up on an auction block, my dear. Have some couth!"

"I'm afraid uncouth is all I can manage."

"Obviously! Seriously, if you want to learn about makeup come over and join us for lunch on Sunday. We'd love to have you."

"Thank you, I appreciate it, eligible granddaughter or no."

We exchanged information and the date was set.


I pulled up in the long driveway of a lovely house in the country. This in itself was a small miracle, as I had almost pulled a u-turn several times on the way. Despite Sonia and Amanda's gracious invitation, I was leery of having anyone see me in a dress under any circumstances. I darn well knew I was too big and too masculine to ever look like a woman. I hadn't felt this nervous since the first time I screwed up my courage to ask Cindy for a date in junior high. Believe me, that's a standard of nervousness that's hard to beat.

On the other hand, Cindy had said 'yes' and we had a good time. I just hoped today would work out as well. And having a change of clothes in the car felt like a risk too far - however, er, interesting it might be to get makeup tips from an expert.

I was spared the nervousness of ringing the bell and waiting for an answer as there were several people relaxing on the front porch. Sonia, in her role as the gracious hostess, introduced me to her son Chuck and her granddaughter Marissa, who looked to be about my age. Odd to have a friend with a granddaughter my age.

Now I was feeling like I was crashing a family party. At least I had a new thing to worry about so I could worry less about being a man in a dress. I wonder if Kissable Kate had any idea what she was unleashing?

The feeling of being an intruder passed quickly as I settled down in a wicker chair with a glass of iced tea and a plate of cookies within convenient reach. I wasn't sure what to expect, but what I got was a lively and interesting conversation about just about anything but crossdressing.

I was quite taken by Marissa, who smiled and laughed and wasn't afraid to express her own opinions, something that was just starting to be accepted in that era, at least by those of my generation. I had never bought into the 'little woman' crap, but I had noticed a whole lot of people in the industrial world sure did expect women to be seen and not heard, unless it involved sex.

When I thought about it, which wasn't often, women's lib sounded like a good idea to me. Looking back, it's kind of ironic that my desire to dress in women's clothes led me to become friends with an ardent women's libber. Did wearing a bra make me a men's libber? One more thing to be confused about.

My musing was interrupted when Marissa asked "So Jay, Granny Sonia tells me she's volunteered my services as a makeup artist. Are you crazy enough to trust me to make you a painted lady?"

"Marissa, I don't think anybody could make me look like a lady."

"Ah! A challenge! Break out the hot rollers and the implements of destruction! My friend, you're going to be amazed."

"And you're going to be disappointed."

"No negativity! There will be only one male in the group and he wouldn't think of commenting on a woman's appearance, would he, dad?"

"Heaven forefend."

"There, it's settled. You did bring your clothes?"

"In the car."

"Well, they aren't doing you any good there, sweetie. Go get them and I'll show you to your room."

"My room?"

"Well, unless you want to do a strip show on the porch?"

"I don't think I'll ever be exhibitionist enough for that."

"Aw darn! I wanted to watch!"

"With your father watching, too?"

"She's on her own. It's your problem, Jay." offered Chuck.

"It's not going to be pretty, young woman."

"Nope, but that's my part in the deal. When I get done you'll be radiant. Go get your clothes."

The playful badinage helped a good deal in easing my nervousness. I had never had anyone see me dressed up before, and I knew I was nowhere near womanly perfection. I was installed in the guest room with instructions to shave closely and holler when I was dressed.

I gave my face a close shave, (legs and arms had been shorn before I came) then dressed. By the time I was done I felt a little like Charlie Brown in his snowsuit - padded bra, padded girdle with nylons attached and waist cincher underneath my long-sleeved, high-necked blouse and full, ankle length skirt and two inch heels. If you didn't look at my face the results weren't so bad.

I had chosen the outfit carefully. Despite Will's advice at Lee's Boutique, I had tried Spandex outfits - this was the eighties when Spandex was the rage - but decided my body just wasn't compatible with Spandex, no matter how much padding I wore. Tight fashions were for women who were half my weight and I looked just plain silly wearing anything form-fitting.

With some trepidation I opened the door to call for Marissa, but she was standing in the hall waiting.

"I love the outfit! You have great taste. Oh, what do I call you when you're dressed up?"

"I haven't really thought about it."

"Jane? It's close to your male name."

"Why not?"

"So Jane it is. Jane darling, sit yourself down and let's get started. Relax, honey!"

"That's easy for you to say."

"First time's a bit scary, isn't it?"

"You've got that right."

"First time Granny conned me into doing makeup for one of her friends I was pretty scared, too."

"So we're both petrified."

"Not me, I'm used to this now. You, on the other hand, are like a block of marble. Relax!"

I felt her hands on my shoulders and her thumbs dug into the tense muscles of my neck and back. I was in heaven! I was in love! I was distracted from my embarrassment as she kneaded my muscles.


I didn't mean to moan, but it felt so damn good!

"You like that, huh?"

"Marry me! I'll be your slave if you keep doing that."

"I tried that once, it didn't work out."


Her fingers had found a sweet spot and all my tension just drained like water from a bathtub. It's hard to remain coherent when someone is rubbing your back, so I shut up and simply enjoyed the experience. I have to admit I tensed up a bit when her fingers reached the band of my bra, but Marissa just kept up her ministrations without a pause. At last she ran her fingers through my hair, saying "Feel better now, Jane?"

"Thank you, my lovely lady. I had no idea how tense I was until you started. Well, I knew I was tense but..."

"It's not so easy to let someone see you dressed up, is it?"

"You've got that right! Especially when you're a big, hairy dude like me. I know the whole idea of dressing up is just silly, but I love it."

"I never could figure out why a man would want to wear a bra, but Granny seems to love it. I suppose it's better than having to fend off some guy who wants to take my bra off."

"Well, if I ever figure out why I want to do it, you'll be the first to know."

"I won't hold my breath, honey. You're not my first by a long shot and none of the crossdressers I've met could give me a logical reason. Don't sweat it, Jane - just go with the flow. Now, let's turn you into a painted lady."

"My mother warned me about them... and now I'm about to become one."

"And my mother crawled into a bottle and became one of the painted ladies your mother warned you about. There are many different kinds of painted ladies out there, Jane."

"I'm sorry to hear that."

"You live with what life hands you."

"So you do. I'm no more sure why life handed me the urge to dress up than I know why life hands some people the need to drink. I count myself lucky that I never started with the booze.."

"Really? You're my kind of... person, I guess."

"Yeah, dressed like this it is a bit hard to get the right word, ain't it?"

"You're a pretty good looking guy, and here I am trying to hide that."

"You take what life hands you, right?"

"Right. Right now I'm going to hand you this apron to keep the makeup off your pretty clothes. You certainly have good taste in your wardrobe."

"With an unspoken 'not like some I've met' somewhere in there?"

"Uh, yeah."

"Don't worry, I've visited a few trans bars in The City - You can learn a lot about what not to wear in those places. Someone with my body has no business in a miniskirt - male or female. I've decided that full, ankle length skirts suit me."

"They certainly do. I wouldn't mind wearing that one myself."

"Came from a little shop on Monroe Avenue called Polk-a-dots. Sick sense of humor but it doesn't Madison to me."

"Stop that! If I laugh too hard you're going to have beard cover up your nose."

"Good thing I trimmed my nose hairs."

"Will you stop that! Makeup is serious business, you need to have the right attitude."

"What other attitude could I adopt when a gorilla wants to wear a bra?"

"You're impossible!"

"I know, but I like dressing up anyway."

"Stop talking, Jane. I'm trying to hide your mustache."


"I said stop talking! Good grief! Don't nod your head either!"

So I sat there and tried to disengage my motor mouth. I talk when I'm nervous. So I closed my eyes and let Marissa work on me. I certainly enjoyed the experience, men don't get to go through the kind of personal service a woman gets at a salon. Believe me, it's something special. That is until Marissa started doing something with a very soft brush.

"That tickles!"

"Whine, whine, whine."

"I'm not whining, I'm laughing."

"Don't touch your face!"

"But it itches!"

Look, you're the one who wanted to experience your femininity. Suck it up, Jane - you can't touch your face until you take your makeup off tonight when you get ready for bed."

"You're kidding!"

"They don't talk about stuff like that in those silly stories that Grams reads, do they?"

"Well, I do like the ones where the fairy godmother waves her wand and poof! the victim is a perfect woman without any effort."

"Fantasy, my dear, pure fantasy."

"I know, that's what makes it so much fun."

"Yeah, you bums get to play and do the fun parts while we real women have to take the whole package - cramps, low pay, drooling jerks at bars, that kind of shit."

"Sounds pretty grim when you put it like that. So why do you do things like my makeup if we're such dilettante wanna-be women?"

"Cause I'm a masochist. Besides, it gives me a chance to carp an a new target each time and I'd do most anything for Grams and Amanda; they pretty much saved my life."


"I told you my mother was an alcoholic?"

"I remember. I had an uncle with the same problem."

"Then you have some idea. I was ten when Mom really lost it and dad just couldn't figure out how to handle it. He was crazy in love with her but the addiction took over her life. In and out of rehab, promises broken within days, fights, the whole works. A ten-year-old doesn't know what to do with such drama."

"Mmmm..." When in doubt make encouraging noises.

"I ended up staying with my grandparents, but I didn't know about Sonia back then. I was in pretty bad shape, like most kids I was certain it was my fault that my parents were fighting."

Marissa had stopped doing whatever she was doing to my face as she told her story, so I opened my eyes. She was standing in front of me with her eyes closed, perhaps projecting her memories onto the backs of her eyelids. What happened next seemed perfectly natural as I put my arm around her and drew her to me. Without any thought on either of our parts she was sitting on my lap and I was holding her closely. Some small part of my brain registered that she was pressing my silicone breasts into my chest, but that was far down in my thoughts as I tried to comfort a woman in distress.

I suppose if I had not been trying to become Jane I would have reacted as the protective male, but that wasn't what happened. The fact that I had been born male and she had been born female was utterly irrelevant; we were two human beings facing hard and painful memories. My only thought was to comfort Marissa as another human being, perhaps as a sister, but not as a caveman protector of the weak woman. Not by a long shot!

I simply held her, trying to soothe the tense muscles of her back as she had soothed mine, just letting the tears leak down her face as she recovered herself.

"I can't imagine how hard that was," I said as she began to sniff and dab her eyes. "No child deserves to have that happen to them, but I can only say you seem to have found the inner strength to cope with your adversity and become a formidable young woman. That has to count for something."

"Thank you, I usually don't break down and bawl my eyes out with strangers."

"It's rather a first for me, too. You're very comfortable to have on a lap, even if you're digging my garters into my thigh."

"I knew it! Only a crossdresser would be wearing garters! Girdle or garter belt?"

"A very well padded girdle, which puts a good deal of unwanted padding between us. We'll have to do this some time when I'm not dressed up."

"Are you a witch or something? You must have cast a spell because I have never sat on a strange - uh - person's lap like this."

"And you can't get much stranger than me. I suppose at some point we'll have to finish with the makeup lesson and go join the rest of the family."

"I guess you're right. Good thing I'm not wearing any makeup or I'd have to do some repairs on me."

"Speaking of which, just how does a woman who doesn't need makeup become an expert in makeup for crossdressers?"

"Because I needed a flexible job when I was going to college and I had a friend whose mother ran a salon. I'd gotten over the 'shovel it on with a trowel' stage of teenage makeup and was pretty good at it, if I do say so myself. I got better with her help. Once Grams let me in on the family secret she started inviting me to help you poor , benighted men who hadn't a clue about makeup. I love a challenge."

"And I'm here to give you one. So what did you major in at college?"


"You're an architect? Very cool."

"I think so, but this discussion isn't getting you ready for your adoring public."

"But it is getting you back to the lovely lady who I first met."

"Thank you, Jane. You've been lovely."

"This may be an odd time to say it, but I'd like to get to know you better - as Jay."

"I think I'd like that. I haven't been on a date in quite a while, having my own marriage go sour kind of put me off such things."

"I suppose it would. When you're ready give me a call."

"No need for a call - what are you doing next Saturday?"

"I think I have a date with you."

"It's a deal. Now let's finish your makeup before Grams starts to think we're using this bedroom for more than a makeup lesson."

"Jane would not think about that - but Jay will when he shows up."

"Pig!" she stood up, leaving my lap empty. "Now let me see your face."

The rest of the day progressed happily as I was welcomed into their family. It didn't take long for me to lose my shyness at being dressed up around others; it was what we would now call a "safe space." The conversation ranged all over the place, but obviously returned to crossdressing numerous times. I learned how Chuck learned his father was also Sylvia and how Marissa became aware of her grandfather's love of women's clothes. Those stories deserve their own telling, so I won't set them down here.

I received occasional gentle reminders as to how to behave like a woman as well as dress like one - something that I hadn't really tried to learn as I only dressed up alone in motel rooms or in my own home. One lesson I had learned on my own was how to eat without dropping food on my bosom - I didn't embarrass myself in front of my mentors.

Being a Sunday, we broke up shortly after dinner, those of us who weren't retired had to be awake on Monday morning.

Feeling a little like a schoolkid passing a note in class, Marissa and I exchanged phone numbers on slips of paper while her father and grandparents watched with a grin. As we parted, Sylvia said quietly, "Told you I had an eligible granddaughter."

What could I say to that? In fact, I was feeling so comfortable I decided to take a chance and drive back home without changing. It felt wonderful to actually walk outdoors as Jane. Since it was dark, I knew I could safely drive into my garage and close the door before I got out of the car. Yes, I was nervous, but I drove carefully below the speed limit and didn't do anything to attract attention. I made it home with no problems.


It felt kind of weird going on a date. Face it, I was, in the latest terminology for the time, a geek. I spent most of my life working or reading; lately the reading was done in women's clothes, but no matter what I wore I was a geek. I could count only three dates in the past five years, all of them unsuccessful and all of them at the behest of well-meaning friends who hadn't a clue about who might be compatible with my quirky personality.

This date was as quirky as my personality: I had met her hanging out with her family with me in women's clothes and she had sat on my lap crying her eyes out as I held her. Not exactly your Hallmark Theatre romantic plot. Nonetheless, we had spent many hours on the phone with each other over the week.

Those conversations had been a bit stilted at first, but as we got to know each other and exchanged the funny stories from our past, we felt more and more at ease with each other. On the phone. Face to face is a bit more problematic.

All right, I was just plain scared. This woman knew my secrets and didn't seem to care. I knew some of her secrets, but they didn't seem to be such a big deal. Yet we both were - put it this way - it's hard to let go of secrets.

So, where were we going to go? Eliminating bars was easy - neither one of were drinkers. I liked that part, dating a woman who needed booze to enjoy herself always seemed absurd to me. I'd done it a few times, just because I was in the distinct minority when it came to booze. Hard to find many non-drinkers when your friends set you up with a blind date.

Music? I wasn't too much into the pop music scene. Sure there was almost always a radio playing in the job - I could recognize the usual playlist but I'd be hopeless in identifying the band. Marissa was into classical music. I was game to give it a try but there wasn't anything happening that weekend. So much for music.

Movies - now there were some possibilities. When you spend a great deal of time in motel rooms you start to go cabin-crazy. One thing you can always find in any city is a movie theater. Not like you can now with 453 theaters in one building, but there was never a problem finding something to watch if you set your standards low enough or were utterly unwilling to stare at the motel wall one more minute. I could even talk intelligently about quite a few movies.

There had been a great deal of hype about something called Back to the Future. I'd seen Michael J Fox before and liked his performances, so that's what we decided to do.

Dinner and a movie - perfectly normal for a date, right? Well, I have to say I felt like a clueless teenager even though I was a quarter of a century old. That makes me sound more mature than saying 'twenty-five years.' The whole angst thing was back in full force: Do I hold her hand? Should I kiss her? Will I slop soup on my tie? (Yes, I wore a tie but I wished it was a bra! They're both constricting but a bra feels so much better!) I wondered if she had similar misgivings.

Despite my jitters the date went well. I was glad that I had sprung for the Mustang, taking a woman out on your first date in a beat up panel van full of tools and parts is less than romantic. In no time we were chatting easily and enjoying the food. During the exciting parts in the movie my hand found hers and stayed there for quite a while. Yeah, just like when I was a teenager, but much more relaxed. And I did kiss her goodbye, or was it she that kissed me? Anyway, it was a pretty good kiss, and lasted quite a long time. I had the urge to, as the old cliché goes, invite her to 'see my etchings,' but good sense prevailed and we mutually decided to take it slow.

We grew closer over the summer, picnicking in the park, visiting with her grandparents, sometimes as Jane, sometimes not. Her father became just plain Chuck, and I got the feeling he approved of me. Poor man - he must have been desperate. I even spent a day fishing with Chuck and without Marissa. I'd never been fishing but I caught a pike that was delicious for dinner.

Marissa and I grew closer throughout the summer, hanging on to the telephone like teenagers for many evenings. When our schedules coincided there were evenings with Jay; Jane sometimes spent weekends with Marissa and her family. I was becoming more and more sure I had found the woman who I wanted to spend my life with.

It was getting on to fall when we were sitting around on Sonia's front porch again, just shooting the breeze and relaxing. The leaves were just starting to turn and we were speculating as to when the peak color would arrive.

"Two weeks, for sure!" said Marissa with conviction in her voice.

"Could be, but I'd put my money on closer to three." Amanda's voice held equal conviction.

"Two weeks. Has anyone got dibs on the cottage that weekend?" asked Marissa

"Not that I remember," replied Sonia.

"Then Jane, you're invited to join me to be in the most beautiful place in the world for the fall color."

"Jane... or Jay?"

"Jane, silly. You need to be feeling relaxed and content to enjoy the color. That happens when you're Jane - don't think I haven't noticed."

"The girl knows of what she speaks, Jane," offered Amanda.

"That's Columbus Day. You're all mine for three days, lady. And nights."

Nights? Not that I hadn't been considering the possibility, but to ask in front of her father and grandparents?

"Chuck, does that mean I need to have 'The Talk' with you before I answer?"

"What makes you think I would have any influence over what my daughter does?"

"Damned straight, Daddy."

"I suppose I should have realized that by now," I replied. "You don't happen to own a shotgun, do you Chuck?"

"You'll be relieved to know I don't."

"You can borrow mine if you need it, Jane." Amanda offered.

"Stay out of this, Grandma. I have designs on Jane that require an unpunctured skin."

"She's all yours, Jane," Chuck shook his head. "And the best of luck to you. I haven't been able to civilize her in all these years."

"Who says I want her civilized?"

"See why I like her, Daddy? We think the same way"

"You have my blessing, Jane. And my sympathy."



I had a brand new problem to solve. Having lived life on the road for years I was a past master at packing a suitcase. A pile of jeans - check. A pile of shirts - check. A pile of underwear - check. Socks - check. Up until a couple of years ago I added a pair of PJs.

A while back that last item had morphed to a nightgown. Packing had grown more complex in deciding what blouses, skirts and dresses I wanted, but that part was certainly fun. Even if the suitcase was full, a couple of bras didn't take up much room. Twenty minutes and I was done.

There was one underlying assumption to my usual work and travel packing: normally no one was going to see me in my dresses and skirts, so if they weren't a perfect match, who cared? In packing for the weekend that assumption was shot to hell. Even if Marissa had seen me as Jane many times before, I wanted to make my best impression on her for our weekend together.

Like she was going to see my underwear for the first time, at least if her rather broad hints were a harbinger of what was to come. I had developed the habit of sleeping wearing a bra with foam inserts - how was that going to fly with her in bed with me? If what usually happens when a man and a woman spend their first night in bed together did actually happen, I didn't think we wanted to be worried about clothes.

But what happens afterward, when you actually sleep? Deep questions with no clear answers.

Then there was the weather - which can change without warning in the fall. As a guy I'd just throw on a sweatshirt if it got cooler, but the fashionable Jane needed several outfits for warm and cool weather. Plus a suitable coat if we went outdoors when the weather was cool. I had to go shopping for that item, outdoors was never a concern for Jane before.

Which brought up another problem - there was no way Jane could go into a store and purchase just the one item like Jay could. Add a couple of skirts (50% off) and a blouse (70% off!) to that warmer coat. Did I really need that scarf? It just went so well with the blouse - really it did!

In the end it took a couple of hours of dithering and the suitcase that usually lasted me a week or two when I was traveling was just as full for my three days as Jane. I was never going to be able to twit my sister about how much crap she brought with her for a visit unless I admitted my hypocrisy to myself. Twitting your sister is an inalienable right, isn't it? It says so in the Constitution or the Bible or somewhere, I'm sure of it!

So by the time I went to bed on Thursday night my suitcase was safely in the trunk of my car, so I could get away early on Friday; being the boss has some advantages. I could take off early on occasion and I didn't have to explain to anyone. I don't know how Marissa managed to get off at noon, but she did and I picked her up at the office. She lives close enough to work that she takes the bus - no need to worry about her car over the weekend.

I found her at her desk and she greeted me with a kiss in front of god and everybody. That may be a repetitious sentence, I've learned that most Architects consider themselves to be Godlike in their majesty. Just don't tell Marissa I said that.

One nice thing about living in a small city is that, barring rush hour, you can go from downtown to the woods in half an hour or less. Even though the cabin was an hour's drive away, it took longer to get there because we went shopping. No, not that kind of shopping - grocery shopping. A weekend alone without food would be pretty lame.

"I hope you realize I'm going to test your skills as a cook this weekend, Jay."


"Letter grades, with points for extra credit work."

"Unless it's dessert I'm in trouble. I can think of a few interesting things to do with a can of whipped cream."

"Be serious!"

"Like I said, I'm in trouble. It's only been a few months since I started to make my own food. The company used to pay for my meals until I got promoted. I've been studying cookbooks."

"You have?"

"Sure - they're no worse than a shop manual. The only problem is that, like most shop manuals, they make assumptions about what you already know when they start to explain things. There is a lot I don't know, but I'm learning. I even have a few jars of spices that I can kind of use."

"Amazing. I would never have guessed you had it in you."

"Sarcastic today, aren't you?"

"Why should today be any different?"

"Well, I could think of a few things..."


"Anyway, did you know that spices were so expensive in the 17th century that were considered proper courting gifts for a man to give a woman?"

"Let's head over to the baking aisle, I have something to add to my list."

"Role reversal?"

"Only until we get to the cabin, Jane.

After a pleasant drive I was directed down a gravel road leading to a dirt road leading to a driveway in the woods, where we found a lovely, secluded log cabin. Marissa unlocked the door and gave me the cook's tour. Not that it took long, there was one main room - what we'd now refer to as 'open concept' with living room/dining room/kitchen - a spare bedroom and what was emphatically referred to as our bedroom.

I hate to disappoint those of you who can't wait for the romantic interests in a story to end up in bed together, but throughout our courtship we had not so much as spent the night together. Disappointing, I know, but this was a relationship that developed slowly - neither one of us was going to rush things and blow it. Marissa had told me about the disastrous marriage in her past. She thought the failure came largely from two teenagers falling in lust, diving into bed together and mistaking good sex for true love.

Hey - I was a Sensitive New Age Guy, or maybe Gal, at least I tried to be. While I would be willing to place a substantial bet that any time a man and a woman were alone together for more than a couple of minutes they would at least have the word 'sex' float across their minds - and I mean both of them - for us building a relationship came first. For us, that meant building two relationships, one with Jay and one with Jane.

Not that our relationship was entirely chaste. Kissing, cuddling, hand holding - even the occasional bit of groping - were certainly involved, but as a SNAG with a woman who had been hurt in the past I let her set the pace. Marissa had clearly made her decision.

Which left me with a problem. She had unequivocally told me the weekend would spent with Jane, and I was perfectly happy to do so, but I wasn't sure I wanted to be Jane in bed with Marissa. What's a Sensitive New Age Guy/Gal to do? Ask her, of course.

"Our bedroom? Are you referring to Jay or Jane?"

"I like to sleep in the nude, other than that I'm spending the weekend with Jane, remember? Get dressed while I put away the groceries."

Ask and you shall be answered!

"Can we go to bed early?" I asked.

"We'll see."

"There was a time that getting sent to bed early was a punishment." I offered.

"Punishment? Don't look in the small closet - it's full of my whips and chains. I wanted them to be a surprise."

"They won't do a bit of good if I'm wearing that padded corset. I won't feel a thing."

"That's funny you should say that - I was intending to feel your thing..."

"I think things are getting out of hand!"

"I rather envisioned things in my hand... and other places."

"Keep this up and not only won't I get dressed, but I'm going to undress you."

"Jay, you'll have to work on making credible threats. That one is pretty lame."

"Incredible! She doubts my credibility. I find that hard to credit!"


Sorry to stop the dialog, but since I was kissing her she was in no position to respond. It was a couple of hours later that Jane was finally able to get dressed.


Have you ever spent a perfect evening? I'm not going to quibble over how you want to define 'perfect,' suffice it to say that fall evening was as close as I've ever come. No - as close as we have ever come. Freshly showered (and shaved on my part) after our romp in bed, we helped each other dress.

If you haven't tried it, I highly recommend the experience. For one thing, having someone else snap your bra together makes the whole process much easier. Surprisingly, I felt absolutely no embarrassment getting dressed while Marissa watched, the trust we had been building over the summer actually let me enjoy the intimacy of having my lover help me transform into as much of a woman as I could become.

We spent a happily domestic time preparing and eating dinner, then watched the sun set before starting a fire in the fireplace and cuddling close while we watched it burn. Sometimes we simply watched the fire without speaking, sometimes we made listless comments about inane things, sometimes we got serious and talked about our future. Companionable talk, like that of old lovers, despite the newness of our becoming lovers. Our slow and easy approach to each other had some great advantages; our lovemaking was more a confirmation of our relationship than the frenzied beginning of something new.

As the evening bore on the fire died and the chill of autumn penetrated the cabin. After a particularly long period of silence, Marissa turned to me and murmured "I'm chilly - let's go to bed."

"Sounds good to me. Are you still planning to sleep in the raw?"

"I've got my love to keep me warm."

"Poetic, but what happens when you get up to pee in the middle of the night? We both can't fit on the toilet."

"Jane, you're thinking like a man. Stop it!"

"Only romantic thoughts, eh? How do you make peeing in the middle of the night romantic?"

"By not mentioning it, darling."

"OK. Can a flannel nightgown be considered romantic?"

"With you inside it, it would work."

"I could appreciate you inside a flannel nightgown, too."

"I could appreciate you inside me, darling."

"You're not making me feel very feminine at this moment."

"I wasn't intending to. Nightgowns can wait - it's time for bed.

"Make up your mind. First you disparage me for thinking like a man, then you command me to think like a man."

"Come to bed and I'll explain it all to you."


In the years to follow I often remembered that perfect weekend when life stressed me almost to the breaking point. Merissa was right, the peak of the fall color was waiting outside the log cabin in the woods. From the moment we woke wrapped in soft, flannel nightgowns we couldn't have asked for a better day. Strangely, getting dressed as a woman with my lover helping seemed as natural as anything I had done. After years of ignoring mirrors showing my intractably male body covered with feminine clothes, I simply put them on like they were meant for me. Maybe they were, even if the rest of the world might disagree. Marissa accepted Jane - no, cherished is a better word.

Being a cool morning, I opted for a warm, cable-knit sweater and a heavy tweed skirt that would be at home in a tale set in an English Manor. The stout hiking boots might not have been the first choice as a fashion accessory, but since we had planned a day tramping in the woods they were perfectly suited to the day's activities.

I was a bit jealous of Marissa, who hardly needed any makeup to complete her more American-flavored jeans-and-sweatshirt outfit, but I was stuck with using beard cover and the works, if only to satisfy myself that I was suitably turned out as a woman.

After a hearty breakfast, we were ready to set out. Looking me over before departing, a look of dissatisfaction crossed Marissa's face.

"Wait here a minute - I have something that needs doing before we set out." With that she disappeared into our bedroom.

Five minutes later she reappeared, wearing a skirt and sweater similar to my own.

"I can't stand it!" she complained. "You're going to make me dress like a proper woman so I can keep up with you!"

"I'm hardly a proper woman."

"But you make me want to get all regressive and wear skirts and crap like that. I'll be drummed out of the feminist society."

"So long as you keep on the beat that outfit would look great for Irish dancing. They use lots of drums, you know."

"Hmpff! Take a hike!"

"That's what we were supposed to do, sweetheart. Lets go."

Not to repeat myself, but in the years since I had discovered the joys of women's clothing, dressing up had been a solitary activity. First in the confines of a motel room, later my horizons expanded to a house when I was promoted. Still later socializing with the crossdresser's group and visiting with Marissa and her family let me experience living as a woman in more expanded circumstances. Now, with the woman I was coming to love and the woods surrounding me, I was free in the world without a care.

There was beauty surrounding me and sensual pleasure within me. I could feel the long, tweed skirt swishing around my calves as I walked. My breasts, admittedly my imitation breasts, were bouncing and swaying in my bra as I negotiated the small dips and rises of the trail. My hand was firmly clasped in Marissa's, at least on the sections of the trail wide enough to let us walk side-by-side.

After a mile or so we found a grove of ancient oak trees that looked over the side of a hill. The ground below our feet was littered with acorns, crunching as we walked. From the seat that some kind person had installed there we sat and contemplated the view of the neighboring farms in the valley below. We watched in silent contemplation as a tractor methodically circled a field of corn, cutting off the stalks and spraying a golden cloud of fodder for some patient cow into the wagon behind the tractor.

A peace fell upon us, surrounding us and filling us with awe and wonder at the beauty of nature. After a long period of silence, Marissa turned to me.

"I know that the man is supposed to ask this question, but I can't see any men around her right now. Jane, will you marry me?"


"Ouch? Was the question that painful?"

"No, I just got hit with an acorn. That sucker hurts." I reached up and removed the offending fruit of the oak from my hair. "Isn't it romantic being in the woods?"

For some reason Marissa thought my being attacked by squirrel food was hilarious.

"If I tell you 'yes' will you stop laughing at me?" I asked with a grin.

"Of course!"


"That was the right answer!"

The dialog stopped once more as we kissed and cuddled and spooned. Nice old-fashioned word, that: spooned; it went with the outfit I was wearing. Hell, it went with the mood we were in. It was delightful.

"So, when?" I asked.


"Not unless you want to be an instant widow. My mother would kill me if she wasn't invited."

"Fortunately, I have no idea how to find my mother. It's not very charitable, but I don't want the old sot at my wedding."

"From what you've said, I have to agree. Do you think Sonia would be willing to take off her dress and be my best man? After all, it's her fault I met you."


"I misspoke - her good offices, I mean."

"Better. You're fast on your feet, lady."

"I'm not wearing heels."

"Good thing I'm not either - you'd be punctured. One bride or two?"

"You'd marry the Bride of Frankenstein?"

"Well, if we put a couple of bolts on a choker it would hide your Adam's apple."

"And Halloween is coming up. If we scheduled it for then..."

"And that would let Sonia be your matron of honor and she wouldn't have to be a he. It's been ages since I've seen Gramps."

"We'd need a werewolf choir to howl during the ceremony."

"I'll howl if we take this much further."

"Just when we had a plan! Oh well, much as my fantasy life would appreciate it, there should be only one bride. The focus should be on you."

"You can still wear a bra under your tux if you want to."

"Why not - why should you have all the fun?"

"For the life of me I can't figure out why you would want to wear a bra. There are times when I just can't wait to get the thing off me."

"Funny, there are times when I can't wait to take your bra off, too."

"So - what are you waiting for?"

"I do have to peel off several layers of foundation garments, you know."

Good thing it had turned into a warm day. Making love on a park bench in the woods was a pleasurable experience, despite being attacked by errant acorns every so often. My makeup was a total loss, though. A very good thing we didn't meet anyone on the way back.


You'll be happy to know we did get married a couple of months later - not on Halloween and minus the fanciful costuming. It's sometimes hard to think I was ever so naïve as that young fellow who walked unknowing into a tranny bar in New Orleans. Who would have thought just how much it would change my life?

Marissa is one of those treasures among woman who understands my need to crossdress and supports me fully. When the kids came along Jane was far less in evidence, but when you're raising kids you don't have a lot of spare time to yourself for relaxing, anyway. Thank heavens for grandparents who actually want to take the little monsters away for a weekend!

You can't hide much from the kids, so they figured it out long before we thought they would. They were cool with my dressing when it finally came out - we seem to have raised them right.

Now that they're grown and off on their own, Jane has more time, often out at the cabin in the woods where Marissa and I spent that first, glorious weekend together. Sonia and Amanda gifted us with the cabin before they passed on and we are going to be grandparents ourselves shortly.

I have the occasional flash of not-quite-jealousy that I cannot pass as the convincing woman Sonia was, but life has been good for us. Heck, I'm even thinking of getting my ears pierced when I retire.

Once again, my thanks to Alys for her editing - and this time she came up with the title when I couldn't.

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