This is a true story. Names and place descriptions have been changed to protect the parties involved (especially me!) If you somehow manage to recognize anyone, please keep this story to yourself. I'd like to be welcome back at the places I went. I'd like to especially thank "Jerry" and "Caryn", two delightful people who could almost singlehandedly make you believe in the goodness of humanity.

I went out last night. This was unusual for two reasons. One, my wife didn't want to go with me. We almost always either go out together or stay in together. The other, I've really, really wanted to go out "dressed," as the kids say, and I finally did, after months of self-torment and tribulations. I went out, by myself, wearing high-heeled ultra-suede fabric boots from Payless, a pair of women's Faded Glory jeans, a black camisole top with built-in hidden bra, a purple cardigan sweater and full makeup.

I'm a crossdresser, a middle-aged married guy who, for whatever reason, finds a certain comfort and a certain latent part of himself when he dresses up as a woman. It's an expression of something, I don't know what, that I seem to need to touch, or express, or something, every now and again. Don't expect any great explanation of what that is here. I've been doing it for a few decades, and I'm not sure. I've been seeing a therapist, not specifically about this, for a couple of years, and she says things about a need to mother myself, and other theories she has. All the usual stuff you read on the tg fiction sites on the web. I'm not sure any of the theories make me go "Aha! That's it!" It just is, if you know what I mean. And, I'm just me, and crossdressing seems to be a part of who I am. A mostly secret part, one I've hidden out of necessity, fear, and embarrassment.

Now, don't expect any great drama, comedy, or tragedy in this little note on what I did last night. There isn't any. I'm just scribbling it down so I can remember it some day down the road, or maybe talk about with my analyst. If you're happy with the answer "Nothing happened," you can stop reading now, because, despite the interactions, and some very minor setbacks and revelations, nothing really did.

The evening started as many others. My wife gets home fairly late, and I usually make dinner, although lots of time, I just use the advance time to pick up some groceries and decide what to make, and then wait for her to get home before starting the cooking. Most of my little masterpieces take under an hour, with the majority taking just over half that time. Anyway, so I had a little time on my hands, and decided to get dressed up.

For about the last week, I've been really planning an outing. It started when I skipped my usual Thursday night visit to K_____, a little nightclub in Williamsburg, Brooklyn, with bars on two floors. I had known it to be a fairly open and accepting place, with a heavily lesbian clientele from the neighborhood. Caryn, the bartender at the basement bar, who's straight by the way, struck me as very open and friendly, and I had told her about my crossdressing a few weeks ago, after one day when I had decided to check the place out after my weekly analyst appointment. As luck would have it that day I walked in, she was substituting for someone else on Mondays, not one of her regular days, but my regular analysis day. Since then, I had been visiting every Monday and Thursday, her other weekday night.

I was bolder than I had been before, asking her on our first meeting a little about the bar, and inquiring as to whether they ever got crossdressers in as customers. She said "Oh, yes. Why, every week we even have a karaoke competition in the bar upstairs, hosted by _________," and she mentioned the name of a locally-famous drag performer. I smiled, and confessed to being a crossdresser, but also that I never had the courage to go out.

We talked a bit, on and off for a few weeks. She told me about her boyfriend. I told her about my wife. We talked about previous jobs and schools. She told me what she was doing now, having gone back to school. I brought in a packet of pictures of my crossdressing progress and accomplishments. She was very encouraging, reminding me that life is short and we need to do what we want to do while we have the chance to do it.

Meanwhile, I took a long look at what girls wore to the bar, and on the streets around the neighborhood, and I realized, that if I ever went there crossdressed, in the winter, in a skirt and heels, or worse, a dress, I was going to stand out like a sore thumb, and an exhibitionist. Heck, if a girl dressed like that, she'd stand out, and be, I guess, considered asking for trouble.

They wear jeans. Everyone wears jeans. So, last Thursday, instead of going to see Caryn at the bar, I went shopping for women's jeans. This was after I tried "dressing" with my own bluejeans, and a nice top, and my boots with the heels. It just didn't work with men's jeans. There's a small chain of discount shops, fairly low-end, but they get some nice-enough merchandise now and again, I guess just local to New York City and environs. So, I took a tape measure, put it in my pocket, and walked up to the store, which isn't far from my house, just a few blocks further on from the supermarket. I found a pair of size 16 Tall "Faded Glory" jeans which seemed to have a 34" waist and a high enough "rise" to reach above my belly-button and hide any flab around my normal men's waist.

When I got them home, they were clearly much better than my men's jeans for the purpose, but they were still a bit loose. I hadn't counted on the spandex in the fabric blend to give them that much play around the waist. It wasn't ideal, but I thought it would work. I wore them that night for dinner. My wife, as usual, was mildly amused by my crossdressing, but in a very tolerant and loving way. Saturday, we were passing by the store while taking advantage of the clear weather and walking our errands rather than driving, so we dashed in, and she had a look around while I combed the jeans bin again, finding more or less the same exact jeans in a size 14 Tall. The tape measure indicated the waist would be a little snugger, but still could stretch to meet my own approximately 36" waist.

I repeated the scene again, yesterday morning, going back, finding the same brand, and a size 12 Tall. The 12 fits much better, everywhere except the crotch, where it's a bit uncomfortable, and perhaps too revealing. They might work, though, with the right pair of control-top pantyhose, and a particularly snug pair of non-stretchy silk panties I have, so I'm going to keep them. At $6.99 per pair, I think I can afford to keep all 3 pairs if I have to.

Last evening, I dressed up again, like I had the previous week. I opted to wear the size 14 jeans. Only a little loose, but not uncomfortable in the crotch. My wife got home just as I was wrestling with my Max Factor Lipfinity lipstick. I usually do it last, although I don't know why, other than out of habit after using regular lipstick for so long. It doesn't smudge. Anyway, by the time she got up the stairs, I had gotten it to dry, and put on a quick coat of the gloss before giving her a kiss.

She had noticed the last couple of days that I've been a bit quieter than usual, and a bit glum and pensive. We got through dinner with her only asking me a couple of times "What's wrong," and "Are you mad at me?"

I told her "Nothing," and "No," although the truth was that I was a bit disappointed that she had previously made it quite clear that she wasn't going to go out with me dressed no matter how badly I wanted her to, and I really needed to go out, not that I could tell you why, only that I knew I needed to.

After dinner, I told her I was going out. She said "Oh?", but you could tell she considered it inevitable. I took off my women's boots, put on some black leather sneakers and put the boots in a shopping bag. One from a chain of shops called "Pretty Girl". I dug one of her old handbags out of a bag full of stuff we have set aside to drop off at a charity thrift shop, but hadn't got around to, and put some stuff I thought I'd need in it. As it turned out, I was still unwilling to take my wallet, keys and cellphone out of my pockets, so I squeezed them in my new pants. I had to take 90% of the accumulated junk out of my wallet, so it would fit, but I just went with essentials and one credit card, in case.

"Oh, you have my purse," my wife said as I came to give her a kiss before leaving. Whether or not she forgot she didn't want it anymore, I'm not sure. I had put my long, silky hair, which I had spent about half an hour going over in the afternoon with some magic spray and a straightening iron, into a ponytail, and pulled on a ball cap. I concealed my top and my mostly-fake breasts under a voluminous down-lined coat, with a scarf wrapped around my neck. I dug out some sunglasses to hide my eyes, which I thought might be the most noticeable part of my makeup outside under the high-intensity sodium-vapor streetlights. And, I headed outside into the deserted neighborhood street and made my way to the car.

Looking in the rear-view mirror of the car, as I prepared to pull out of my parking spot, I saw that my makeup was incredibly obvious, and was glad of the dried road splatter all over my windows from the recent snow and road salt, to help conceal me from view of other drivers on my way to my destination. I took off my sunglasses. Driving at night with them was at least suspicious looking, if not performance-impairing. At each red light on the short but interminable trip, I tried to avoid lining up directly with another car's side window, as drivers at red lights will often look around and idly stare at who's in the next car, and I didn't really want that.

A couple of short blocks from the K_____ bar/club/nightspot, maybe a total of 5 or 600 feet, I spotted some available curbside parking next to a mostly windowless brick industrial building. The immediate area was a bit quieter and more visually isolated and, it seemed, darker than the adjacent busy commercial blocks. I judged it an ideal place to fuss around, change my shoes and make my exit from the car, where I would hopefully have a head start on blending in with my surroundings.

No sooner had I locked my door and stepped up on the sidewalk did I realize that my "street reflexes" were in full force. By extreme force of habit, my body wanted to walk like a guy, that guy who never has any trouble on the streets of Brooklyn just from the way he walks and carries himself. That guy who would be trouble if you bothered him, you'd think. No amount of willing myself to loosen up and let the heels set my posture would have any effect. I stopped briefly and tried walking again. I put one heel in front of the other and shifted my weight to the other foot. Nothing. I just couldn't lose that street posture. As soon as I started walking, that purposeful, gravity-laden stride returned. You can't walk in heels that way, let me tell you!

So, I sort of teetered and pogo'ed herkily and jerkily down the street, fighting my muscles and my programming, past the White Castle, past a couple of small apartment buildings, past two construction sites, thinking to myself that I was walking like some completely messed up "crack ho" and conscious of the fact that this walk with these heels was killing my lower back. I had spent countless hours comfortably at home on these very same almost-4" heels, running up and down stairs, gliding around the kitchen preparing meals, walking the rooms and hallways with about the same speed I achieve in my normal male footwear. When I'm home, I'm definitely at home in my heels, and these boots are the easiest to walk in of my various women's shoes, because although they have the highest heel, they feel the most secure with the ankle zipped snugly in.

Blessedly, I reached the front door of the club, grabbed the door and stepped in out of the frigid air. There was a small group of younger people gathered in front of a club employee. My initial thought is that there must be some kind of cover charge or something for whatever was going in the main bar. Didn't matter. I was going downstairs to the other bar, and to do that, I didn't even need to go as far as that group of people. I turned to head down the stairs, took two steps and heard the girl facing that group shout at me to get my attention, "Sir! Sir!!"

This is an inauspicious beginning to my evening, I thought. Okay, I continued, maybe I have to pay a cover charge to go downstairs, too? Besides, this is a predominantly lesbian bar, and if a lesbian couldn't immediately tell who was a girl and who wasn't, well then nobody could, and further besides, she might be less willing to be polite to me.

Anyway, the story was, she had to check everyone's ID for age. I'm not sure I buy that. Nobody had checked my age in a bar since probably before she was born, and if she's bright enough to spot my gender in a darkened bar at 10 paces, why not my age? Oh, well. Submit license. She peers at it and thanks me. Meanwhile, the group in front of me walked out. Maybe she was just rattled at having to chase some underaged patrons away.

I get downstairs and Caryn the bartender is all alone, takes one look at me, even before I get my hat and coat off, and says "Very nice! You did a great job." My evening was picking up.

She liked my makeup. It wasn't that great, and I know it could be better, but I guess she was expecting something much worse. I let my hair down and tried to fluff it out a bit. It doesn't look bad from the front. From the back, that's another story. I could definitely use more hair. I unbuttoned a couple of buttons on my cardigan to reveal what little cleavage I was showing.

I'm out, I'm crossdressed and I'm driving. Drinking, crossdressing and driving, pick any two. I ordered a Perrier. This isn't a very prissy club, it turns out they don't have Perrier, or any fancy sparkling water for that matter. Caryn shows me a bottle of off-brand drinking water. They were even out of Poland Spring, their one and only usual brand of bottled water. I suggested ginger ale instead. She packed a glass with ice, ginger ale, and decorated it with some lemon and lime wedges.

I admired her manicure. The polish looked new. She said, "Oh, I just had this done today. It's been a while since I had my nails done in the salon. It's just a brown. It's a little dark, but I think it looks good with short nails."

My wife hadn't liked the dark-red polish that I had favored before I started dressing openly at home and took me shopping for some slightly brighter colors that she liked better. Caryn and I talked a bit about nail color and length and going to nail salons. That's on my list of things I'd like to do, get my nails done. Ask them to paint them red, too. See the look on their faces and see how they treat me.

We also talked about stuffing bras. She started it, offering a tip out of the blue about how if I wanted, I could wear two bras at once to have a bigger chest. I sat up a bit straighter, pushed out my chest and objected, "They're not that small."

"No, they're not. For the Super Bowl, though, I'm going to wear three bras!" Caryn is a small-framed woman, perfectly nomal and acceptable to my eyes. I guess she needs bigger breasts for professional purposes. Bigger breasts, bigger tips for the bartender. It's a shame, though, if she's selfconscious about her body-image. Her body looks good on her. On the other hand, she's old enough, in her late 20's, that if she was going to get implants, she probably would have already had them, so maybe it's just a work and special-occasion thing.

I don't know what came over me, but I slipped one of the "chicken cutlet" breast enhancers out of my built-in-bra camisole and said "I use these." There wasn't anyone else down there in the downstairs bar but us two.

"Oh, I have those! I love those." She told me she also had gel bras with those built in, as I rearranged myself.

We talked about makeup. She complained she couldn't find a foundation that really matched her skin. I told her about my collection of random foundations I keep buying to try and how I'd like to go for a makeover at the department store some time and let a pro help me. We talked about jeans and how they can enhance a girl's figure. She shared with me how she puts pantyhose under hers, especially in the winter. We chatted a bit more, about what was on the tv, about music, about her school. I enjoy talking with her.

A scruffy-bearded , extremely nerdy man arrived, putting an end to my time with her alone. She seemed to try to chase him away after he asked what was going on downstairs. "Well, tonight, you have your choice of smart or stupid. Upstairs is smart, they're having Trivia Night," a regular weekly competition. "Down here is stupid. We've got the tv on!" She had some silly new show on, on the AFX network. It seemed ignorable to me, and in fact, the two of us had been paying no attention to it at all.

The bearded guy opted for "stupid" and our company, I guess. He sat next to me in front of the tv above the bar. There were other seats within easy viewing distance of the set, and the long bar was empty. I was a bit put off by him sitting right next to me. Sitting next to a tv (although I prefer the term "cd") and watching tv. How ironic. His English was a bit stilted and slightly accented. It reminded me of the Hasidic Jews of Brooklyn, although he wasn't dressed the part, and he was sitting in a bar drinking a whiskey sour. I'm not sure who drinks whiskey sours any more, and he had seemed unsure of his order, didn't have any idea of what whiskey to request when Caryn asked him if he had a preference, and in fact, didn't seem to me if he had ever ordered one before. Was it just a drink he had heard of? Was he in fact a Hasid who was having a wild night out amongst the Goyim? I didn't look at him. Stared into my drink, had Caryn refresh it when it was gone, kept up a little light banter with her.

A very stylish woman showed up, with an impressively stunning hairstyle. She was black and the hairstyle was quite inventive and artistic in a way that only hair-conscious black women seem to seek out. Swept up on one side, or was it clipped short? And swept down over one eye and off to the side. She could have walked off the pages of a fashion magazine. She ordered a massive vodka martini, with Grey Goose vodka. $11 worth. She glanced at me and then stared into her drink, looking up at Caryn now and again and carrying on some light banter.

Caryn continued covering all the bottles on the back bar with little plastic cups, a task she had started before the last customer had arrived. I had asked about it. It seems if you don't do this, any fruitflies in the joint make a beeline for the little pourers and die in the bottles. I had never seen a fruitfly in that bar, but they do have fruit, so it's possible. The downstairs bar closes at 12:30, and she had school the next morning, so she wasn't going to stick around if she didn't have to. There was a bit of time yet, but I thanked her, we exchanged smiles, and I climbed back into my coat and headed back to my car.

It was snowing lightly, and my boots weren't waterproof, a fact I became more conscious of as I noticed the puddles forming in the walkway in the street set up around the building sites as I stepped off the sidewalk. I hadn't noticed that I had had to step off the sidewalk going the other way. I hadn't noticed much of anything, in fact. I walked a little better, but not much. Unlike the trip the other way, I had to pass two oncoming pedestrians, at close quarters. I tipped my head so the bill of my ball cap shielded my face as I passed. I still fought with my center of balance, trying a little more consciously to try to get it aligned somewhere over where my feet were.

My decrepit car was still where I left it. It had been stolen once when it had been a lot newer. It wasn't worth much any more, but I'm never confident that no one would want it. The gearbox is worth far more to a repair shop than the car is. I'm always a bit surprised and gladdened to see it again. I didn't take that for granted any more. I'm also pleased every time it starts. I abandon it for days or a week at a time in between uses, often in a dark, dreary and unprotected parking space somewhere or another. It's been much nicer to me than I have to it. Meanwhile, I had a Metrocard in my wallet in case I had to take a bus or subway home. I was about to change my shoes, when I started thinking about whether I was ready to go home yet.

Less than a quarter mile from my car was another bar I had previously scouted. Jerry, the bartender, would be on tonight. I hadn't seen him in a few months, but he had recognized me before after lapses longer than that. I was last to visit him the week before Halloween, and that Saturday the bar was to have its Halloween party. I got all dressed up that night, but could never leave my house. I took some pictures of my makeup, posing pretty well, I thought. Well enough to deceive most of my chatroom friends into telling me things like "I'm not sure what you were worried about. You could pass! You look good." Well, I don't. It's just a clever pose for 1/100 of a second in front of 1000 watts of light reflecting off a large white sheet hung a few feet from my face. I know a few photographic tricks. I also had to throw away 20 of the 21 photos which caught way more boy than girl.

But, I hadn't left the house that night. And, I hadn't had the courage to face Jerry again, after all my confession to him about my crossdressing and all his questions and encouragement and invitation. I had failed, and I couldn't face hearing again the last thing I had heard from him. "That's a nice dress," he said sarcastically about my jeans and corduroy shirt the last time I had been there. Jerry is a dear. He's a gay man who works in a lesbian bar and watches over the place like a hawk. Strictly speaking, it's not exclusively a lesbian bar. Gay men and straight couples also go there. It's really just a friendly neighborhood bar, but not one for the straight singles.

When I first told Jerry about my crossdressing and asked him if it would be okay if I ever got the courage to come out and visit, he said "Sure!" But, then he got all puzzled. We had previously talked about ourselves and he knew I was married. He had a million questions about crossdressing straight guys. He was embarrassed by the fact he was asking me all these questions, but I reassured him that I understood the puzzlement, and did my best to be as open and informative as I could, given my own limited understanding of what "makes" me do it. On another visit, I brought him some pictures. On another visit, I brought some more pictures and then we involved some of his friends among the women patrons and got some advice on which of my outfits they thought would work the best if I wore it to the bar. Everyone was pretty cool with my crossdressing, and I was pleased and surprised and encouraged. But, I hadn't had the courage. And, I was ashamed of my cowardice.

This was a chance to make up for it, a bit. I determined to go visit Jerry and at least say hello. Walking was out of the question, especially with the sidewalks wet, and I didn't know how much more it would snow. So, I'd drive. Before wrestling out of my high-heeled boots and back into sneakers, I decided to take my usual driving position and see if I might be able to work the pedals. I only need to go 1/4 mile, make two right turns, and park. I decided to brave it. For some reason, my car started running really rough, or acting like something was dragging, or both, after the last traffic light before the bar. I was still terrified by trying to drive with heels on and decided I'd just park, get my visit at the bar in, and then change and deal with it.

There were a few people in the bar. Still a few seats left at the end nearest the door, most of the crowd up the other end. Jerry came down to greet me like he does most people as they walk in. He gave me a puzzled look and then, as I slipped out of my winter gear said "Hey, stranger. Where have you been? Ohhhhh.... Look at you!"

He didn't have Perrier either. A lesbian bar and no Perrier. I've decided to completely revise my view of lesbians. They are evidently not effete, pretentious, afraid of alcohol or on diets, either. In fact, the biggest selling drink there, I know from experience, is beer. On tap, in bottles, or by the case. Jerry confided to me once that some of "his girls" can really drink. He pointed out one very large and rough-looking girl to me that night saying "When she comes in, which is not every night, thank God, she'll drink an entire case by the time she leaves."

Jerry suggested a seltzer and cranberry juice and fixed me an entire pint of the stuff. Then, after we had been chatting a bit, he invited me down the other end of the bar. "Those are my friends, would you like to meet them? Come on. Come with me," he said, picking up my drink, napkin and money and moving it all over to sit next to Sharon, who he introduced me to, and to his serious boyfriend who he's talked about before but I never met, Emilio, and to Yvonne, who is the bartender some other nights of the week, but was there hanging out and just being a customer. It says a lot for a place that you work that you want to hang out even when you're not working, don't you think?

No one said anything about how I was dressed, or my makeup. I smiled, they smiled back. We all shook hands. That was it. In short, our interaction was just like anyone's. Maybe a little friendlier than I'm used to from strangers, now that I think of it. But, I wasn't a complete stranger to Jerry, and his friendliness is infectious, anyway. So, the crossdressing certainly didn't hurt anything, at least.

I had taken a look out the window before I went with Jerry to the other end of the bar, both to look at the progress of the snow, and to look at my car across the street. That was when I noticed that I had a flat tire. That explains the strange "running rough" and "dragging noises" syndrome.

After chatting about food, cooking, and a few other things with Jerry and his friends, I took my leave, explaining about the flat and that I wanted to try to deal with it then so I could get the car home, or at least off that street, so it wouldn't get ticketed for blocking the sweeping machines in the morning. Jerry and Emilio were honestly concerned, but in a way that I found a little stereotypically funny of effeminate men. "Do you have Triple-A? I could call them for you." And, "Have you ever changed a tire??" asked in a most unbelieving voice, as if no one they had ever met ever would have. I really was touched and gratified by their concern, which I took to be a sign of accepted kinship. I assured them I was fine, and that if I wasn't, I'd be back to take off my makeup and butch up the best I could before calling a towtruck.

It turned out the tire was more or less fine. I had stupidly forgotten about the slow leak and not having put any air in it for a few weeks, drove it with hardly any air in it, and it just let go of the rim, letting out the rest of the air on the last corner. Hooking up the electric pump I had in the car didn't quite do the job by itself thanks to the gap between the tire and rim, but taking the weight off by jacking up the wheel did. The tire inflated, and I didn't have to actually do any hard work. Jerry and Emilio came outside so Jerry could put a ladder back in the basement, one of those basements you get to by lifting flat steel doors in the sidewalk over the outside staircase, and shouted "Are you okay? How's it going?" to me across the street. I ran back over, now in my sneakers, assured and thanked them and said goodnight, and then ran back to my car to turn off the pump and put the jack back in the trunk.

I got home okay. Got the exact parking spot I had vacated 3 hours previously, and came in to greet my wife, who was still up, waiting for me, probably concerned, but not saying so. She asked how it went, and if I had fun, and I gave her a capsule summary, maybe talking more about the tire than the outing, but at least acting pleased on both accounts. And she was, too. It was well past her bedtime, and she was asleep by the time I got my makeup off and teeth brushed, and I followed a few minutes later, after putting on my men's flannel pajamas, my little excursion done for the day.

Notes:

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