A Lost Case

Our luggage was looking a bit tired, so we decided to purchase some new. It seemed sensible to get two smaller cases rather than one large suitcase. It would be easier to move and carry. If one of us went away alone, or if two of us went away just for a weekend, one smaller case would be enough.

The only problem was that when we arrived at our holiday destination, only one of the two cases appeared on the luggage carousel at the airport. We made enquiries and were eventually told that the other case had been misdirected. The airline would get it re-routed and it would be delivered to our hotel.

We had each packed our own case in preparation for the trip, and the case that was missing contained all my clothes and toiletries.

We were told that it should arrive before breakfast next morning. We explained the situation when we got to the hotel and after checking in to our room, we explored the city and had a nice dinner. Back at the hotel there was still no sign of the lost case and the receptionist provided me with shaving tackle and a toothbrush. So after a drink at the bar, we settled down in our hotel room for the night.

While I was in the shower next morning, my wife rang Reception to check if the missing luggage had turned up. When I came out of the bathroom after showering and shaving, my wife told me the case still hadn't arrived. She said that the receptionist had advised to buy some new items of clothing and underwear and to make a claim against the airline or our travel insurance.

"Well, dear. I can lend you some of my clean underwear for now and we can go shopping after breakfast. I've probably got a shirt you can wear as well - you spilt a little wine down yours at dinner last night."

She searched through her case and handed me a pair of pink knickers. "I think these will fit you," she said.

As soon as I stepped into the silky knickers, memories of my teenage years flooded back. The times when I'd been alone in the house and had sneaked into my mother's bedroom to try on her underwear. She had had undies like these knickers, soft and cool against the cheeks of my bottom, the feminine fabric enclosing my maleness with illicit sensuousness...

I suddenly realised that my wife was grinning broadly. "I can see you like wearing those," she laughed.

I felt myself blushing. Putting women's underwear on today had had the same effect on my genital region as trying on my mother's knickers all those years ago.

And it was an effect that showed no sign of abating.

My wife handed me a pair of pop-socks and a cream blouse. I put them on in silence. There was no point in trying to refuse them. Not with the obvious and persistent evidence of my arousal.

Fortunately the blouse was a fairly loose fit and not very tailored, so it didn't look outrageously feminine. But the buttons and button holes were on the opposite sides from those on a man's shirt.

And the collar and cuffs were not particularly manly.

There was a little rose motif on the left breast pocket, but this would be hidden by my jacket.

By the time I'd put on my jeans and shoes, my knickers not longer contained a tent-pole, just a sizeable bulge. We went down for breakfast.

It was only when we returned to our room that I remembered that I'd been going to wear my jacket.

We went out shopping. But not to any menswear shops. "I know what sort of knickers you prefer," she laughed.

Not wishing to be seen searching through selections of ladies' underwear, I waited near the store doorway while my wife bought a few things. When she re-joined me she had a shopping bag that seemed to contain more than just a couple of changes of pants.

We dropped off the shopping at the hotel and went off to do the things that we would normally on holiday, seeing the sights, visiting interesting buildings, eating a light lunch, and so on.

Although I was able to forget that I was wearing feminine underwear some of the time, I did keep getting reminders as the silkiness of the knickers caressed my skin...

That evening as we returned to our room after dinner my wife hand kept stroking my bottom.

Once again I was very aware that I was wearing silky pink knickers and by the time we reached the room I had a throbbing erection.

I was soon standing in the middle of the room wearing just my blouse, knickers and pop-socks, while my naked wife stood close to me, fondling my balls through the sensuous fabric of my knickers, her breasts brushing against my body.

A few moments later I was lying on my back on the bed, still wearing the same things, but with my knickers pulled down to mid-thigh. My wife was astride me, totally in control of our love-making.

Finally I exploded inside her. It was as if the pleasure of wearing knickers all day, with the consequent repeated semi-erections, had caused my balls to fill themselves to bursting point and were now pumping themselves dry.

My wife leaned forward, her breasts just in front of my face, as her cunt seemed to squeeze the last juices out of my cock. She kissed me and we lay for a while until my shrinking cock finally slipped out of her.

She got off the bed and stood at the side of it. "Pull your knickers up and come here," she said. "All that stuff you squirted into me is starting to trickle out."

As I knelt in front of her she held my head in place as I dutifully lapped up the love-juices, my lips kissing her labia.

When she was finally satisfied, she let me get up. "Thank you, darling," she said. "That was wonderful."

"And now I've got a little present for you." From the shopping bag she handed me a burgundy nightie and some clean pink knickers.

I took off my other clothes and put on my new things. The nightie was rather like a slip, with broad shoulder straps. It was only just long enough to hide my knickers.

It felt divine and one again I was reminded of my teenage dressing up escapades.

But there was no erection. I was too exhausted.

We got into bed and I was soon drifting off to sleep in her arms. I felt as if she was cuddling me like her daughter.

Or perhaps more like her son dressed up in pretty girlish clothing.

The next morning after I emerged from the shower she informed me that she had checked with Reception and that the suitcase had still not arrived.

"But don't worry, dear. I got you a few new things. Just in case."

As soon as I stepped into my new peach knickers, I knew that they were just as sensuously stimulating as the pink knickers from the day before.

"And look," said my wife. "I got you a bra as well. It's got AA cups, so it won't be noticeable under your shirt."

"But since I know you like wearing knickers, it's a pretty safe bet you'll enjoy wearing a bra as well. Bra and knickers go together, don't they?"

I didn't know what to say. Should I protest that I didn't need a bra? But she knew how much I liked wearing silky knickers.

And to be honest, I quite liked the idea of wearing a bra as well.

But I didn't want to admit this.

I didn't say anything.

She helped me to put the bra on and to adjust the straps and fastenings to ensure a good and comfortable fit. She played with my nipples through the fabric of the bra-cups.

"Bra and Knickers, Bra and Knickers." she whispered with a little giggle.

She handed me a new pair of pop-socks and a white shirt. Well, she said it was a shirt. But it looked rather more like a blouse to me.

And it felt like I was wearing a blouse when I had it on.

But perhaps that was because of the bra.

As there was still no sign of the suitcase we would need to go shopping for more clothes for me.

"I'll have to go on buying women's clothes for you," said my wife. "If we are going to make a claim for all the additional purchases it will look odd if we buy both men's and women's clothes when only one of our cases went missing."

She was watching me as she said this. We both knew that this was rather a weak argument.

But I didn't know what to say. Should I insist on my maleness? Or enjoy the opportunity to wear more women's clothes?

I had hesitated too long. My silence meant that I had accepted her decision.

So the following day, with still no sign of the suitcase, I found myself walking to the shops wearing not just a bra and knickers under my blouse and jeans, but also a suspender belt and stockings.

As we walked around the shopping area, looking in the windows of various clothes stores, we stopped in front of a display of dresses and skirts. My wife pulled me close to her and spoke quietly.

"Wouldn't you like to wear a dress tomorrow?"

She could tell I was startled and an little upset by the suggestion.

"There's no need to worry, darling. We're on holiday here. Nobody knows us. I can do something with your hair."

"Even if somebody realises you're a man in a dress, they won't know who you are or where you live"

"And we're only going to be here for another couple of days anyway."

My initial reluctance faded somewhat. It was true that we were a long way from home. My wife would be with me to support and look after me. I had often wondered all those years ago, what it would be like to go out in a public place wearing a dress. Now perhaps I had a chance...

As I went to the bathroom the next morning, my wife said, "Don't forget to shave your legs. You can use my razor. I've left it out for you."

And although a lady's razor is in many ways the same as a man's razor, I knew it was a lady's razor.

I was using a lady's razor to shave my legs.

To make my legs more feminine.

I wore trousers to go down for breakfast. But wearing a blouse and a full set of female underwear.

Then we went back to the hotel room and my wife helped me on with my new blue dress.

We had deliberately chose a dress with not much shape in order to conceal my lack of bust, hips or slim waist. The hem of the skirt was a few inches above my knees, but quite long enough to cover my stocking-tops. I wore some unisex sandals. My wife quickly did something with my hair to make it look less masculine.

We both examined my appearance in the long mirror on the wardrobe. "You look very pretty, dear," said my wife.

"Nice legs, too. I think you should keep them shaved like that."

As we walked through the hotel lobby, I kept my eyes facing forward. I didn't want the receptionist to recognise me.

But from the corner of my eye I could see that my wife gave her a wave.

We left the hotel and walked along to the museum. It was very strange being out in public and not wearing trousers. I suppose girls and women get used to wearing a skirt from an early age. But I was very aware of the absence of trousers and had the strong feeling that at any moment people would be able to see my knickers and stocking-tops and suspenders.

Especially if my skirt bounced up as I walked, or got moved by a slight breeze.

And if this should happen, not only would I be displaying my pretty pink knickers, but also the tell-tale male bulge in them.

I don't know whether people thought we were a couple of acquaintances, friends, or "an item".

But I noticed how male eyes looked at us. At our legs and busts.

I was a little disappointed that I didn't have more of a bust to ogle. Probably they were watching our bottoms as well. "Don't ever look back," advised my wife.

She gave me a whispered reminder to keep my legs together when we sat down in a café.

I did gain a little more confidence as the day wore on. We went on a boat trip, and once or twice I did have to hold down my skirt as a cheeky sea breeze threatened to display my underwear and reveal my little secret. I was relieved to get back to the hotel without any incident.

Once again I did not look in the direction of the reception desk as we passed through the hotel lobby.

And indeed, once back in the security of the hotel room with no fear of being in public view, the delicious sensation of the freedom of a skirt, the soft silkiness of my knickers, the tautness of my stockings and suspenders, and the gentle but insistent grip of my bra straps all combined to bring my cock to throbbing attention.

And when my wife sat beside me on the edge of the bed, and when she put her hand on my knee, and when I parted my legs to allow her fingers to explore up my skirt, I closed my eyes and imagined my self to be a teenage girl submitting willingly to her horny boyfriend...

My wife treated me to a blow job. We had a little snooze before dressing (conventionally - outwardly at least) for dinner.

I wore my dress again the next day. We went to a shoe shop and I manages to find some shoes to fit me. They only had one and a half inch heels, but I was amazed what a difference they made.

My legs took on a more feminine shape. My bum stuck out more. I had to walk more daintily.

And I was more aware of my stockings tugging at my suspenders with every step.

And swishing as they brushed together.

I began to regret that this was the last day of our holiday. Tomorrow we flew home.

To normality? (I wondered if everything would be quite the same from now on...)

It was quite a squeeze to get all my new clothes into my wife's suitcase next morning, along with all her things as well. I didn't pack all my new things - I was wearing a new blouse, with my bra, suspenders and stockings under my male jacket, jeans and shoes. And a pair of silky knickers, of course.

We went down to Reception and my wife waited on one side with our suitcase while I went and checked out. "Thank you Mr Willis," said the smiling lady receptionist. "See you again soon!"

"Well, maybe," I replied.

The receptionist laughed. "Your wife told me that this visit had brought back many happy memories for you. She thinks you'll be back soon!" She giggled as if she knew a little secret.

"Oh, and by the way, Mr Willis," she went on. "Your other suitcase is here for you. It arrived on your first morning with us, but your wife said you didn't need it."

I saw that she and my wife were smiling. A knowing glance had passed between them.

And I realised that the receptionist had ever-so-slightly emphasised the "Mr" when she had addressed me.

I realised that I wasn't really a "Mister" any more.

My wife couldn't have known in advance that my luggage would go missing. But when that chance event happened she had taken full advantage.

Away from home - and away from family and friends and neighbours - She had taken the opportunity to feminise me.

And I liked it. And she knew that I liked it.

Our relationship was now different. She was now the stronger personality. The boss.

I guessed that feminising activities would progress further.

I was, in terms of my masculinity, a lost case.