My First Bra

CHAPTER 1

It was a joke, and a good one. At 60 years old I was not an Adonis, but then I never had been. Middle aged spread. A bit of a beer belly. And yes, I admit, man boobs.

Christmas presents are for children. My wife and I buy what we want or need when we want or need it, providing we can afford it. And I don't try to outguess her with clothes or jewellery. Instead we buy each other small, jokey things.

This Christmas morning, I opened my present to find a bra! A pretty lacey one. An insult! And a laugh!

"Come on," she said, "I'll help you."

It took a bit of adjustment, but it actually fitted! She bought all my clothes because she said I have no taste, and frankly I didn't care much what I wear. She liked me to look smart, and fair enough because she always looked good. And my boobs were actually big enough to fill small cups! I suspected a New Year's resolution to diet was going to be made on my behalf.

There were some knickers as well. It was the funniest thing ever. And it didn't actually feel bad.

We agreed that I would wear it under my clothes for lunch when our daughter and son-in-law came round, with their children of course. I would be in the obligatory Christmas jumper, so it wouldn't show. To complete the joke, my wife would be wearing my underpants.

Lunch was good of course. We acted surprised at the presents our grandchildren had received, and thanked them for the handmade cards and little gifts. But we were so cheerful our daughter asked us what the big joke was. We said we were just happy to see them, which was not untrue.

When the Queen came on television, it was time for them to leave, and us to have our afternoon snooze. Thank heavens we don't have to look after the children. Being grandparents is the best! We can't snooze when we are at work, of course, but it is a Sunday and Christmas tradition after a big lunch and a small drink.

Now we were on our own, we changed into our slobby clothes. She has a sort of track suit and naps on the sofa. I just wear a T-shirt and underpants in bed for a couple of hours.

"Wait a second," she said, and went and brought a nightdress. It was a bit large for her: a rare mistake, and something she should have returned, but sometimes you forget. No sleeves, lots of little blue flowers and a bit of lace. I took off the bra and put on the nightdress, which was just as comfortable as the T-shirt.

I woke up feeling really refreshed and went downstairs to make myself a cup of coffee. She was stirring on the sofa, so I offered her one. I had slightly forgotten I was in a nightdress.

She accepted her drink gratefully.

"You can wear it instead of pyjamas," she remarked. "It's just like a nightshirt, and if it's comfortable it doesn't matter that it has flowers on it."

"Maybe," I said.

On Boxing Day, we were rather at a loose end, so she got me to put on the bra and knickers again. I put on the nightdress. She said she would have liked me to put on a dress, but we knew they would be too small. However, I agreed to put on some tights.

She then spent at least half an hour making me up, while I watched the TV over her shoulder. She had a fun wig which she had rarely worn, but this went on me now. We went to look in the bedroom mirror, and laughed so hard we had to sit on the bed.

When we had recovered, she said "Actually you don't look bad. I might do this again!"

CHAPTER 2

Christmas was followed by the January sales and she came home with bags looking pleased. A cup of coffee, then off to the bedroom to try something on. Eventually she called me, and I was pleased she did.

She had touched up her makeup and hair and was standing in a red set of underwear. Bra, panties, suspender belt and red patterned stockings. She looked great, and I told her honestly that she looked very sexy.

Not bad for 59 and two kids, I thought. I'm a lucky man.

"And these are for you," she responded, pointing to the bed, where another set was laid out.

"No," I said, laughing, but a bit uncomfortable. "Don't be daft!"

"Go on," she wheedled, "just for me. Don't be a spoilsport!"

How could I refuse?

The first problem was that the bra was not big enough for my chest, but she had anticipated that and bought an elastic thing which added an inch or two at the back. The suspender belt had to go under my belly, and I was glad that I didn't have to do up suspenders every day, as they are rather fiddly.

However, I was done, and we looked in the mirror. We smiled, but this time it did not seem funny. Silly, yes, but not funny ha ha. I looked ridiculous, of course. But there was a feeling I couldn't quite put my finger on.

She was also not laughing as she had expected, and looked puzzled.

"You need makeup," she said, so sat me down.

It was a bit boring, but at the same time I wasn't bored. I was sort of relaxed. I don't know. Let's say I was neither annoyed nor amused, but on the positive side of feelings.

In the mirror I could see a ridiculous fat old man in sexy women's underwear and makeup. But I didn't laugh, and I wasn't embarrassed. I sort of felt OK.

"Now the pièce de résistance," she announced, and produced a maternity smock! It was pretty and pink, with plenty of room for my belly.

On it went. Now that WAS funny!

I walked around, sometimes holding my belly, sometimes putting my hand to my back.

"I think you're about 7 months gone," came the comment.

We hugged each other and laughed. We could still act daft!

"If only the kids could see me now," I said, and she collapsed onto the bed giggling.

The humour sort of petered out and we looked at each other non-plussed.

"You can take it off, whenever you like," she said. I said nothing.

"Or keep it on, of course."

I took it off. And undressed completely. And went and washed my face. Fun over: back to normal.

CHAPTER 3

She had another surprise for me that evening. An actual men's nightshirt. Plain blue with no lace, of course. I wore it all that week and it was OK. In the wash it went.

"How was it?" she asked.

"Fine," I said.

"Shall I get you another?"

I hesitated. "No, I don't think so."

"So, back to pyjamas, then?"

"Yes, of course."

That evening the nightdress was on the bed.

"Put it on," she said. "You looked so disappointed when I said pyjamas. If it's comfortable, that's fine. Nobody's going to see."

I slept really well, all that week. But I was also thinking about bras, though I didn't say anything. I couldn't understand why I just thought it would be nice to put on a bra again. I wasn't gay; I didn't want to be a woman. I just thought it would be nice.

But what I thought of as "my" bras had been put away, or perhaps thrown away. I didn't know and I didn't ask.

CHAPTER 4

Sunday morning was time for our weekly lovemaking. Nothing outrageous. We each showered. Foreplay to get me up, plenty of lube, and taking her from behind as she bent over the bed. It had been a while since missionary position was practical with my belly, but we were both happy with what we did.

Afterwards, we cleaned up, and I was going to get dressed, when she said "Do me a favour."

"Of course," I said, mentally wondering about the garden, drains or tidying up some of my mess.

"Put on your red underwear," she said, and produced the set from the sales.

"If you like," I said cautiously, and with her help I did so.

She looked at me carefully. I don't know what she was thinking.

"Makeup?" I asked.

"No," she said. "Just a man in a dress for now," and went and got my maternity smock and the wig.

She looked at me thoughtfully.

"How do you fancy a pub lunch for a change? It would save me cooking."

"Er, yes," I said, "but not like this!"

"Of course not, you silly! Now you just go and relax in your pretty clothes while I get ready, then we'll get you back to your usual man state. Just enjoy the change!"

I think the word 'nonplussed' describes what I felt. I had never really understood what it meant before, and I couldn't define it, but that was me.

So I did relax. I made a cup of tea, watched some TV and reflected that it was definitely better than gardening or the other chores I tended to get on Sunday. I didn't know what was up, but I wouldn't mind doing this every weekend.

She took as long as she usually does and came down in a casual top and slacks, with her hair and makeup done nicely of course. Just fine for Sunday lunch at the pub.

I went to the bedroom to change. I took off the wig and dress, but she stopped me taking off the rest.

"No keep it on. We're going out in the same underwear!"

I started to protest, but she cut me short.

"No-one will know. You'll be wearing a sweater, just like at the Christmas dinner. Go on, do it for me!"

I put on a T-shirt and sweater, my best jeans, and black socks over my stockings.

So in casual weekend clothes we went to the pub, where they do a rather good Sunday lunch. She kept smiling at me, and at one point leaned forward and whispered conspiratorially "I'm wearing sexy red underwear with stockings and suspenders!"

"Me too," I whispered back and felt my face go red.

"When I rub my thighs, I can feel the suspenders," she added in a hoarse sexy whisper.

I didn't answer, but tried it, then hastily put my hands back on the table. This was definitely an experience! I hoped she was getting sufficient amusement out of it, because I wasn't, though there was the thrill of the forbidden.

She was certainly cheerful as we went home, but didn't want to talk about it.

"Nap time," she said.

With well-filled belly I was ready for my Sunday afternoon snooze. She gave me a new nightdress, same as before but with pink flowers. Afterwards, she insisted I wore the bra and panties, but not the stockings and suspenders, and my smock. I guessed that weekend jobs were off the menu, which was good.

What was not so good was taking me to the bathroom to stand on the scales.

She also made me up in what she described as basic domestic style. I didn't wear the wig, but continued until bedtime.

Dinner was just some sandwiches, which was fair enough as we had had a large lunch, and she obviously appreciated not cooking.

Then she explained.

"Now you have an idea of what women often do. Lots of them you will see in quite plain clothes are wearing sexy underwear. You don't know but they do. They may have no-one to see them in it, but they still buy it. We can feel it sometimes: the lace, the nylon, the satin, and we can think about it at any time. It just makes us feel good. I hope you felt something of that."

I muttered in a non-committal way.

"Oh, that's a shame. I must have got things wrong. I've been reading up on the internet about men who like wearing women's clothes, because I thought you did." She paused and looked at me.

"Let's get you out of these silly things, then. I'll get rid of them, and I promise I will never ask you to put on a bra again!"

I don't know what expression I made, but it made her laugh.

"I see! You look like a sad puppy who's had his bone taken away. Oh, poor darling!"

She grabbed me and kissed me and hugged me.

"Let me tell you what I read. Apparently 15% of men do it at some time, so it is hardly unusual. They're mostly not gay. They just like women's clothes, especially underwear, in much the same way women do. They're pretty, they can be a bit silly, they're fun."

"Now so long as you don't run off with another man, it's fine if you want to come home and relax in a bra and a dress. I shall enjoy going out with you sometimes knowing you're wearing stockings and suspenders underneath. Oh yes, I read about this: it's called underdressing. Fair enough, I suppose, for men to do the same as a lot of women. Perhaps there are other couples who wear the same underwear!"

"Well," I said, somewhat hesitantly. "I could try it, if you like."

I really wasn't sure. I had just had this vague feeling. I had never thought about what she had just put in words, but now she had, perhaps it would be nice.

"I expect the novelty will wear off soon enough," I added.

"Probably," she answered with a little laugh. "By the way, did you enjoy your lunch? The food I mean, not just the experience."

"Yes, it's always good there. And the experience was something, too."

"That's good, because we won't be going there again soon. And no more pub lunches at work. Your New Year's Resolution is a diet."

I had expected this, of course, and she was right.

"According to your BMI, you are obese and should lose about 30 pounds, that's a couple of stones or 15 kilograms on our scale. Or 4 babies! But I don't want you too skinny, and I think these ideal weights are a bit mean, so let's say 10 kilograms. That should get you down to the stage where we can get you a nice dress that's not for maternity. But just to encourage you, you can choose some nice item of underwear for every 2.5 kilograms."

"I'll be dieting, of course, so we can be a bit miserable together."

I made the required comments that she did not need to diet, and she snorted and kissed me.

CHAPTER 5

On Monday she gave me a packed lunch, and had obviously contacted someone at work as my colleagues expressed commiseration. I think one of the women was ready to report if I went to the pub with some of the guys, or had something extra at my desk. That evening, I sat down to a rather small portion of mince and pasta with plenty of salad, dressed in my maternity dress and my first bra and knickers. I will draw a veil over the tedium of dieting, other than to say beer was also severely limited.

However, it had the desired effect and eventually the scales showed my first achievement.

"No what shall we get you?" she asked. "How about a nice underslip, or a silky nightdress?"

"A bra," I said immediately.

"Why did I bother to ask? Well, I have had an idea, just come with me."

We went to the spare bedroom, where she had her bras laid out. I didn't realise she had so many -- there were ten! Her idea was simple, but brilliant. Using an elastic extender at the back, I was able to try them all on. It was such a happy time. Of course, the straps needed adjusting, and they were a larger cup size than my man boobs, but the effect in the mirror was marvellous. I got to choose one!

"There's a little bonus," she said, producing a package with a flourish. "It's a sports bra, which I think you could wear in the garden and probably under some of your regular clothes without showing. What do you think?"

I thought she was the best wife in the world. It wasn't as pretty, but it was nice to feel that I had it on. I did a bit more gardening than I had in the past. I even wore it at night sometimes. I didn't dare to wear it to work, but got into the habit of wearing panties there quite often.

At 5 kg I chose another bra, and she presented me with a bonus in the form of a satin nightdress, which looked and felt delicious.

At 7.5 kg my belly was well on the way out, but unfortunately so were my boobs. She remedied this with some silicone bra inserts which made the difference, so that the cups were actually filled.

10 kg was success and disappointment. Everyone said how well I looked and complimented me on sticking to a diet. However, my boobs were now really small. She said that there were many women this size, and I should not complain. She gave me a bra she had bought in AA cup. I was actually pleased that I could feel it directly on my nipples instead of just the silicone.

Then we went out to buy the first real reward. A sexy set in white lace: bra, panties, belt and stockings. The sort of thing a bride might wear. With the belt shortened and the bra extended, it fitted, and my belly did not overhang. In the mirror I looked wonderful!

We went out to a restaurant wearing my suit and a white shirt, with my new set underneath. I hardly noticed the food with the excitement and satisfaction. To be out in public as a man, with stockings and suspenders under my trousers and a bra under my shirt. Just perfect!

When we got home, we started to shed our outer clothes and I said "I hope my bra didn't show. Did it?"

"Maybe," she said. "Just a little..."

That was it: we were fucking on the bed, half-undressed! There was no foreplay, but somehow she had an orgasm, which was something that had not happened for a long time.

Having cleaned up we discussed what had happened and how much we had both enjoyed the evening. At bedtime I put on my nightdress, then took it off again. We slept naked together as we had in the early days of our marriage.

CHAPTER 6

Memory is a funny thing. It is not at all like a recording. It is a story you tell yourself over and over again, changing a little each time. It is perfectly possible to remember things that didn't happen or mix two events together till you are sure they were the same. We each had different recollections and discussed or even argued about it so many times that I am not sure what happened, or if anything happened at all. However, this is how it seems to me.

The aim of the diet (apart from health) was to get me into a dress which was not for maternity wear. I am not sure if this was to please her or me, but it was the plan. As she had better taste and more experience, I left it to her, and looked forward to the surprise.

As it turned out she had three outfits: two dresses and a skirt and top. To be returned if not suitable. The one I liked immediately was a green sleeveless one with a pleated knee-length skirt flaring out. Oddly enough, she had got it by chance in a charity shop when delivering some things. With makeup, wig and underwear, I put it on. This is the point where our recollections don't agree, but as far as I can make out, this is what seemed to happen.

I put on that dress, and immediately felt totally feminine. I was transformed -- I WAS a woman.

But at the same time, I said something like "No, I don't think so. Perhaps someone else would like it, so you should return it."

(This is the point where we disagree most. I think I was quite vague. She insists I spoke in a very definite way as if I was being instructed. "This is not for me. It's for someone else. It needs to go back.")

And my wife said "But it's perfect!"

But in that dress, I sort of understood myself, and dropped my doubts about what I had been doing. It was really all right for me to enjoy bras and other clothes. But I wasn't a woman.

Stupidly, the thought flashed through my mind that if I kept the dress, I would become a woman! And I realised I wanted to feel LIKE a woman, but not BE a woman. And everything seemed right.

So I took it off.

"No not this one."

She was puzzled. "But it seems fine. It's from a charity shop, and they don't do refunds. We can keep it in case you change your mind."

We kept the others, but the next day I donated the green dress back to the shop.

CHAPTER 7

Whatever had happened we were both now clear and contented with my hobby. I was a man who liked women's clothes at home. Especially underwear. And especially bras. And I soon had quite a wardrobe with more bras than my wife! I wasn't gay or transgender, and I didn't want to fool anyone that I was a woman. I liked being like a woman. And it was a bit of a thrill to go out 'underdressed'. I pretty much always wore nice panties even at work, but was cautious with bras.

I persisted with the diet until I lost 15 kg, which pleased my doctor. Of course, a bit returned, but I am determined to keep it down.

Maybe it was an improvement in health, maybe it was the dressing, but we had sex more often, two or three times a week, which we reckoned was not bad at our age.

My man boobs had almost vanished. However, we got some silicone pretend breasts which are very realistic and filled my first bra. (I don't wear that particular bra very often to keep it and the red set in good condition for sentimental reasons.) This became my standard cup size, and the weight was just right, so I had a dozen bras in different styles.