My First Dress

My First Dress

CHAPTER 1

I don't know if it was the male menopause or simple curiosity, but sometime after I was fifty, I wondered what it was like to wear a dress, and began looking at women with that in mind. I didn't want to be a woman. I didn't think I had been misgendered or wish I didn't have a penis. I was quite happy to have one, though would have preferred if it could operate like it did thirty years ago. I didn't want to have breasts and wear a bra, though my chest showed some signs of going in that direction.

The young women with bare legs well up their thighs. Older women with skirts which went below their knees, which they must feel with every step. Long ones nearly to the floor. Tight skirts. Ballgowns. Of course, women often wear shorts or trousers these days, but I just wondered what it was like to wear dresses instead.

I never tried on my wife's clothes. She rarely wore a dress these days, anyway. She didn't even wear a nightdress, just pyjamas, like me.

So it started when she bought some new pyjamas for both of us (not the same), and I said they weren't comfortable. To tell the truth I'd been having trouble for some time. Quite simply, I didn't have a waist to hold them up, and if I pulled in the cord enough it was uncomfortable. The elastic had gone on my old ones, so I had to hold them up.

"What you need is a nightshirt!" she said, as I rejected the new pyjamas.

"Like Scrooge!" I said, "And a nightcap!"

She laughed.

"No, I've seen them advertised. I think they're quite trendy now. Do you want to try one?"

"Why not?" I said, as I thought 'I'll be wearing a dress!'

"What colour would you like?"

"It doesn't matter. No-one'll see me and I'll be asleep. Anything. Pink if you like!"

We both laughed, and I went back to pulling up the trousers occasionally during the night, and holding them up when I got up for a pee in the morning.

But a few days later, she raised the subject.

"You know I said I'd get you a nightshirt? I said they're getting trendy, which means they're quite expensive. Did you mean what you said, when you said the colour didn't matter?"

"Of course," I said, and she went away.

She came back with a pink dress on a hanger. I don't mean all nylon and frilly. Some cotton combination with a slightly fancy buttons and a printed heart on it. No shape, just straight up and down.

"I used to wear this a few years ago, if you remember."

I didn't, but I nodded.

"Just try it on."

I did. It was entirely comfortable. I walked around.

"It's great," I told her.

It was just above the knees. Covered my bum and more. A perfectly ordinary dress.

That night, when I went for a pee, I sat down to do it. I don't know how to describe it other than a sort of schoolboy glee. I was walking around in a dress, and peeing like a woman! I liked feeling the edge as I moved around.

Of course, it wouldn't do to just have one. I didn't know it but she ordered something online.

A few days later she produced a blue one. Not the same design, but similar material with a pale blue background and little blue flowers.

I put it on.

"It's a miniskirt!" I said laughing, while I thought 'It's a miniskirt!' with delight. Halfway up my thighs, though still decent.

"Oh, I'm sorry!" she said.

"I didn't think. The model must be a lot shorter than you. It's obvious. It's a shame I've washed it, so I can't really return it."

"It still covers my bum. I'll try it and see," I said and pranced around a bit.

Actually, it was a bit difficult keeping my bum covered as I slept, but I was so pleased, though I had to try not to show it.

She apologised for the next one.

"It was on offer and so cheap. Two for the price of one."

It was well past my knees, so if I sat down, I was demurely covered. It was just right as nightwear. And when I got up in the morning and went for breakfast, I liked how I could feel the hem when going up or down stairs. At the weekend I lounged around a bit before getting dressed - that is, changing into jeans.

I started wearing them in sequence, a couple of days each. Until I was wearing the minidress.

"Oh, for heaven's sake!" she said.

"If you're going to wear that, put on some underpants. Or don't sit down."

"There not comfortable overnight," I told her.

"I wear them for going out, but they're too restrictive for lounging around and definitely not sleeping."

A little while later she came back with a packet of women's knickers. They were just plain black, not decorated in any way, but something silky.

"Just try these for size," she told me.

"They might be a bit loose, you not having the right hips, but let's see."

They were wonderful! But tended to slip down, so she bought me a pack of smaller ones.

"Just at home, for comfort."

Why didn't they sell these things for men? I never knew what I was putting up with. (With what I was putting up?)

CHAPTER 2

Now we come to the moment which changed my life.

For the winter she bought me a long knitted acrylic one- effectively a maxi in a light caramel colour. It had no sleeves, so she bought me a navy blue cardigan to wear when reading in bed, which I put on. And some open-toed slippers -really sandals with fur, adjustable with Velcro. I don't like closed slippers because my feet sweat, and I get athlete's foot.

I put them on, and I was the most comfortable I had been in my life! It really wasn't about feeling feminine, just comfortable. My feet were warm enough but not sweaty. My legs were covered, so didn't feel the draught, and I was not too hot. I found the cardigan just right, but took it off later when I was feeling warm.

She looked at me and smiled, then hurried upstairs.

She came down with some fake pearls, and put them round my neck.

I looked in the mirror and laughed.

"I look like a duchess!" I said.

"My husband's turned into an old lady!" she replied.

Yes, with my grey hair, I really did.

The sandals were perfect for home.

"You know, I could wear this all day and every day," I told her, and meant it.

She bought a second one while it was available, for washing.

Another nightdress (quite cheap) was essentially a soft dark grey midi. She bought me some black knee-high socks for warmth in the winter. It also went well with the cardigan.

I started using them as loungewear. That is, changing from my workwear into a dress for the evening, and mooching around in the morning.

For Christmas she bought me a genuine man's nightshirt, in dark green with light check pattern. It looked just like a dress that a woman could wear, just knee-length. (And more than twice the price of any of the women's ones, from some 'traditional' supplier.) I put it into rotation with the others.

For a joke she also gave me some cheap clip-on plastic pearl earrings to pretend to be the duchess with the pearls and the caramel dress.

As I posed, she suddenly said "Ooh, let me do something," and rushed off.

She came back with some makeup and put on lipstick, then darkened my eyebrows and lashes. We had a good laugh pretending to serve dinner to the Duchess and I acted like someone out of Downton Abbey.

That eventually led to something else.

Maybe it was the Yuletide and New Year alcohol, but I actually told her I had wondered what it was like to wear a dress. I liked the nightdress and the daydress because they were comfortable, but it had been interesting to have my curiosity satisfied.

She must have read my thoughts, because I certainly wouldn't have said what she recognized.

"So you wonder what other sorts of dresses might be like?"

I think I blushed.

"Well, maybe. I don't mean we should buy anything else, and I'm certainly not planning to go out in public, pretending to be a woman. This is quite enough. I was actually surprised how comfortable these are, so I don't need anything else."

Maybe I was gabbling a bit.

"Of course not, darling. You were just a bit curious. I don't think you're any the less of a man. Now let's go to bed."

We did, but just to sleep, though I think both of us lay awake for a while.

CHAPTER 3

We'd settled down. I only wore the duchess dress and the man's nightshirt as a day dress in evenings and weekends. The mini was really too short for the night, but the grey midi was ideal, and the others were OK. I liked the feeling when I got out of bed and came downstairs in them, mostly with a dressing gown in the winter, before having breakfast and going off to work. And it was a treat to put on a dress for the evening.

I didn't want to be a woman. The makeup had been for her, not me, but there was something comforting about the way I could just notice the feel of the hem on my legs as I moved about. It was a habit to sweep the skirt to cover my bum as I sat down. I did the same thing getting into bed, sitting on the edge and pivoting, so that my legs remained covered. It was a habit, but something I still noticed with a tiny feeling of satisfaction, I can't explain it better than that.

And of course being careful when I sat on the toilet. I only stood to pee at work.

Wearing a dress was just nice.

It was at the end of February when my better half said "Would you do me a favour?"

Of course, I said yes.

"I know you're not trying to be a woman, but I'd really like to see you as one. Could I get a wig and give you some makeup on Sunday? Just for my amusement?"

"Oh, all right. No problem."

"In fact, I don't mean just the duchess. I'd like to see you in a different on each Sunday for a bit. Is that all right?"

I had no reason to argue.

Over the following weeks we went through all of them. She actually got two wigs (cheap, she said), a brunette and a blonde. She spent a long time with the makeup, but I couldn't argue - it was fun for her. Then I stayed that way until bedtime.

It was strange. When she was putting on my makeup it was rather boring. She didn't like me to talk, and I couldn't see myself in the mirror, but as well as the tedium I felt sense of suppressed excitement, and a feeling of triumph when I saw myself and she admired her handiwork. Not bad at all. I felt a little buzz all day - maybe a bit sexual, but I didn't get hard. Not until bedtime, when my face was clean and the dress off, and we made love. Being dressed as a woman for a day seemed to be the best foreplay for both of us!

I also got a pair of women's shoes (flats) to wear on Sundays, with socks or tights as she thought suitable for the character. After a while, I used them on other days, whenever I wore a dress.

At some point a padded bra was produced to make my Sunday character more realistic. I didn't wear it otherwise.

CHAPTER 3

I think I didn't look bad in the nightdresses, but buying an actual summer dress showed there needed to be a change. We had been having a meal out and a generous Chinese takeaway each week, but these stopped. With further restrictions, I slimmed enough to be able to put on a pencil skirt at Christmas. Fake leather, rather tight on the waist, loose on the hips, but narrowing down to my knees.

I had always wondered how women managed with their legs restricted in this way. Now I found out. On New Year's Day I had another gift - shoes with heels! She'd bought two sizes and we returned one. They were only two inches, but I staggered for a long time before being able to manage in both tight skirt and heels!

Over the next few years, we had great times dressing me up in all sorts of ways. Petticoats were a lot of fun - soft ones, stiff ones, with short dresses and long dresses. Fishnet tights. Stockings and suspenders. Schoolgirl. Sexy maid (joke). Tight dresses (which showed I wasn't a woman!). Long dresses. Even a bit of sexy nightwear (but too silly to wear all day!) Nothing too expensive. And bedtime frolics afterwards.

For the other days it was about comfort. I learned the value of underslips for warmth, hygiene and comfort. Good quality (not cheap) men's nightshirts were quite good as regular day dresses.

Our back garden is quite secluded, so in decent weather I could walk around and enjoy the feel of the dress and the breeze (or sometimes sunshine) on my legs. There were some days when I could go out in the minidress.

I had working dresses for mowing the back lawn and household chores. It seemed a bit of a shame to have to put on jeans to do the front lawn.

By the time we came to retirement, we had a plan. We sold the house and had a holiday in Canada to visit our two sons and their families. Our new house was by the seaside in a place where no-one knew us.

We introduced ourselves as Leslie and Carol (or vice versa), not Mr and Mrs, not 'this is my husband/partner/wife', just our names. Leslie always wore a dress; Carol was mostly in trousers but had a bigger bust. People could think what they liked about us. So far it's been fine. Neighbours and other people we saw regularly never challenged us or seemed offish. Just two older people with age-appropriate clothes and a little makeup. I think I've only once been asked if I was a man. I said yes, and that was the end of it.

Almost the first thing I did was to enrol in ballroom dance classes, to learn the women's steps. Now we regularly go to afternoon dances, mainly patronised by older people. We each have some nice dresses, not the most expensive, but cheap, which have been tailored to fit by a local woman. I have a special bra for each.

We both like twirling around in fancy dresses, and it keeps us fit. There are more women than men, so we often dance together, but it's nice when two gentleman separate us. There's one who takes me quite often now. Nice, but he's not getting anything else from me, apart from a dance.

We still have sexy Sundays, which are more of a laugh than anything else, with outfits I would never go out in! But they still get us ready for lovemaking.

The rest of the time we are just two pensioners who love each other, enjoying retirement. We go out to the beach or a walk round the floral gardens, sometimes to the museum or the cinema. We chat with neighbours, eat ice-cream, and watch the young people having fun.

I can't express how good it is to be out and about in a dress. I just love it.