A Dream Holiday

My parents had gone on an extended visit to Australia and had rented out their house for half a year. So during the long summer vacation from college I had gone to stay with my Aunt Carol. She was a reasonably well-off divorcee living on her own in a large house in the leafy suburbs.

When I arrived she seemed very pleased to see me and I guessed she might be a bit lonely and glad of some company for a while. She made a pot of tea, well, not exactly tea - it was some sort of herbal infusion that she explained had health-giving properties. It was different, but quite pleasant. I had a couple of cups.

She showed me to my room. It was close to a bathroom, which she explained would be for my use only, as she had a bathroom attached to her bedroom. It all seemed very amenable and convenient.

The bedroom had a vaguely feminine appearance, but the bed seemed comfortable.

The wardrobe had some dresses, which must have belonged to Aunt Carol's daughter, because they didn't look as they were in my Aunt's style. But there was plenty of room to hang my relatively few shirts. There were some empty drawers for my other stuff.

Although there a couple of drawers with some female undergarments. I guessed that my cousin must use this room occasionally when she visited.

After unpacking I went back downstairs. Aunt Carol was in the kitchen preparing the evening meal. She offered me a glass of fruit juice, explaining that it had added vitamin supplements. I got the idea that she was into all that sort of health-food and hoped that the meals would not be too bizarre.

Nevertheless, I accepted the drink, reflecting that the sort of food I was used to at college was probably not all that healthy.

Besides, Aunt Carol looked pretty fit, so whatever she ate and drank seemed to be good for her.

I needn't have worried about her style of cooking. The meal was delicious and I even quite enjoyed the "healthy" drink that we had with it. I felt quite tired after the long journey from college and decided to have a fairly early night. My aunt gave me a couple of tablets to take before getting into bed. "They will help you get a restful night," she explained. I slept well.

The next morning I felt very refreshed. I went to the bathroom and shaved. Then, as was my habit, I sat on the edge of the chair in the bathroom with a pair of tweezers. I was used to spending 15 minutes each morning using the tweezers to ensure that every single pubic hair was removed as soon as it appeared. I lifted the end of my cock with the fingers of my right hand so that the fingers of my left hand could fondle my silky soft hairless balls.

My balls felt, well, feminine. Of course, I knew that girls didn't have balls. But if they did, they would be smooth little plums, just like these.

Girls had tits, not balls.

And as I glanced at my chest I realised that I DID have tits. They weren't enormous. But they were unmistakable swellings on my chest.

I was sure they hadn't been so noticeable the day before. There was enough flesh to cup each one in my hand.

And my nipples seemed to be larger too. I got into the shower. I gave particular attention to washing my titties with the shower gel. Would they get bigger if I massaged them?

I couldn't help feeling that they were indeed getting larger. When I dried myself on my towel I noticed that my bottom seemed bigger than it used too.

But I concluded that I was just imagining things.

However, when I was back in my room and starting to get dressed I found that my clothes didn't seem to fit me properly. Either my underpants had shrunk or my bottom was definitely a lot bigger.

I did manage to get them on but they were uncomfortably tight.

I also had some difficulty to fasten my shirt. The mounds on my chest stretching the front of my shirt so that a couple of the buttons looked as if they might snap off at any minute. My nipples were very prominent (and I soon discovered) a little tender.

And there was a real problem with my skinny jeans. I did manage to fasten the button at the waist, but there was no way I could close the zip - the fly gaped wide open because the material at hip level was stretched around my nether regions which were definitely much larger than they had been the night before.

Aunt Carol knocked on the door and asked if I was ready for breakfast. I explained that I had a problem with my clothes.

She came in. "Oh, I see what you mean," she said. "Let me see if I have anything that might fit you." She reached in the wardrobe and some of the drawers and handed me a selection of clothes.

"I don't have any trousers, I'm afraid," she said, "but I think this skirt and top will fit you."

I took of my shirt and put on the stretchy pink top. It fitted well and was surprisingly very comfortable. It also showed off my new titties!

She showed no sign of looking away as I unfastened my jeans and took them off.

"Your underwear looks very tight too," said Aunt Carol. "I think you would be better to put on a pair of these knickers."

She handed me a pair of silky white nylon knickers with dainty pink frills around the leg-holes and a tiny pink bow at the front of the waist.

"I know they look a bit girly, but your underpants are obviously far too small. These will be much more comfortable for you. I'll turn round while you change into them."

They weren't just comfortable: the cool soft material felt divine on my ample bottom and my hairless balls. I felt a little tingle in my cock and hoped it would not give me away by demonstrating my pleasure in wearing these lovely knickers.

I stepped into the pale blue skirt It had a button and a short zip at the back, which my Aunt helped me with. It was a perfect fit around my waist, but was rather short, showing at least six inches of leg above my knees.

"Well, not perfect," said Aunt Carol, "but you do look much more comfortable in those clothes. Come and have some breakfast and we'll see what other clothes we can find for you later."

It felt very strange sitting at the breakfast table wearing a short skirt. Strange, but not unpleasant.

There were more health drinks and vitamin pills. I realised that the changes to my body must be caused by something I was eating or drinking.

But for the moment, at least, I was enjoying my new body shape and was happy to keep taking the supplements.

After breakfast I helped Aunt Carol clear away the things. Then she had a good look at me and said, "Well, if we're going to go shopping for you, I think we'll need to improve your appearance a little. I can do something with your hair, but your legs are a bit hairy for wearing a skirt. Why don't you go up to the bathroom, slip your skirt off and shave your legs?"

I complied with this suggestion and returned a little later with hairless legs.

My aunt brushed my hair (which was rather long) and put some clips in to give me a more feminine style. "Now you look more like my niece than my nephew," smiled Aunt Carol. "Are you ready to go to the shops?"

I wasn't sure if I was ready for this. "My legs feel rather cold," I said.

"Hmm," said my aunt, "I suppose you're not used to going around with bare legs, especially now that they're hairless. Come upstairs and I'll get you some stockings to wear."

Once again I slipped off my skirt so that she could fasten a suspender-belt around my waist.

"Now thread the suspenders down inside your knickers," she said. "It's more convenient when you need to go to the loo!"

Once I had done this I put my skirt back on again. I was now practised in manipulating the zip behind my back.

She showed me how to carefully gather the nylon stockings round my thumbs before putting my foot into the toe, and then smoothing the nylons up my legs, finally fastening them to the suspender clasps.

"Now adjust the length of the suspenders so that they are reasonably taut," she explained. "That will prevent you getting wrinkled stockings."

"I think we need to get you some proper shoes, though. Your trainers don't really go with the rest of your outfit but I don't have any shoes your size."

A few minutes later we were in her car driving to a shopping mall. I liked the look of my stockinged legs. My skirt only just covered my stocking-tops, so there was quite a lot of leg visible.

I began to get a bit more nervous, however, as we reached the parking area and I realised that there were a lot of people about.

I think Aunt Carol realised that I was rather apprehensive. We didn't get out of the car immediately after parking. My Aunt gave me a few tips.

"When walking in a skirt you need to take shorter steps. Take your time. Don't rush and remember to walk daintily. Don't make eye contact with any boys or men. Don't look back. Look where you're going and at shop windows."

"Don't just look down at the floor all the time. You need to act confidently, even if you're not really sure of yourself."

"When you sit down, smooth your skirt under your bottom. And be sure to keep your knees together when seated. Make sure the hem of your skirt is pulled down so that you don't show more of your legs than you mean to."

"And don't cross your legs while wearing a short skirt."

"Are you OK to get out now?"

I nodded nervously.

I clung to her arm as we walked across to the shops. As we entered the mall I felt as if everyone was watching me. I remembered Aunt Carol's advice on looking confident and tried to look calm.

Every time we passed a male I could feel their eyes looking at my legs and/or my chest.

I kept checking my reflection in shop windows to reassure myself that my skirt was covering my knickers and stocking-tops.

Our first stop was a shoe-shop. "Now remember to keep your legs together when sitting down and trying shoes on," said my Aunt.

Fortunately we found a pair very quickly, so I didn't have to sit there trying different shoes and at the same time trying to avoid displaying my underwear.

The shoes were a pale cream colour and had one and a half inch heels. "Those heels are quite high enough for now. When you're used to walking in them we could get some higher ones if you like," said Aunt Carol.

I kept them on and carried my trainers in a carrier bag.

"Now remember to walk daintily," said my Aunt. "Short steps and don't drag your heels."

We went into a large department store and Aunt Carol took me straight to the bra department. She addressed one of the assistants, "My niece needs to be fitted with her first bra," she said.

The assistant led us into a changing room and asked me to remove my top. "It's important to be properly measured," she said. Once she had taken some measurements, she left the room.

"I'll only be a couple of minutes," she said. She returned with a white bra, which she proceeded to take out of its package. She helped me to put it on and spent a few moments adjusting the straps. "That's just right." she said. "Is it comfortable?"

I nodded. It was not just comfortable, but also somehow comforting. The straps were not tight, but I could feel they were there. And the cups felt soothing on my slightly tender nipples.

"This is a teen bra," explained the assistant. "It will help you to get used to the sensation of wearing a bra. It is very lightly padded and you can continue to wear it as your bust develops a little further. But as soon as it starts to feel a little small or less comfortable, you need to come back and be measured again."

"If you're not sure whether you are needing a larger size, come in for a size check and we can advise you."

"Thank you," said Aunt Carol. "We'll take it. But I think my niece would also like one that's more padded so that she can buy clothes that will still fit her later."

The assistant went and brought another bra. She helped me remove the teen bra and then fitted the padded bra.

"This will give you the equivalent of an A size," she explained. "I guess you will want to keep this on for the time being if you are going to buy clothes now."

I nodded and put my top back on as my Aunt paid for the two bras. Now I did not only have a comfortable and reassuring bra on, but also I had an even more noticeable bust shape.

We spent a couple of hours doing more shopping. I got a few dresses and skirts, a few blouses and tops, several pairs of silky knickers, a couple of nightwear sets comprising short nightie and matching knickers, some more stockings, another pair of shoes with slightly higher heels, and a lipstick.

Walking back to the car I was much less nervous than I had been when we first arrived, but I was still aware of male eyes watching me and appraising my legs and bust.

Back at the house I gave my Aunt a hug and thanked her for taking me shopping. Then I went up to my room to try on some of my new clothes.

I watched myself in the full-length mirror as I took off my skirt and top. In no time I had a huge erection in my pretty knickers.

Despite other parts of my body being more feminine my cock seems longer and thicker and harder than ever. I pulled my knickers down far enough to release my cock and balls and sat on the bed.

I was surprised how supple I had become. I was able to lick the end of my cock. I pulled back my foreskin and kissed the shiny pink knob-end. My lips enclosed it as my tongue explored the hole in the end and my hand massaged the shaft.

Moments later a shudder jerked my body and a spurt of cum hit the roof of my mouth. I swallowed. My lips eagerly tried to extract every last drop of cum as my erection subsided.

I stood up and pulled up my knickers. The soft cool fabric soothed and supported my tired flaccid cock. It was now so small that there was only a tiny bulge in my knickers.

I felt quite girly with the (almost) smooth outline of my knickers.

And the taste of cum in my mouth.

I put on a skirt and top - some of my new clothes - and went downstairs to my Aunt Carol. "Is there anything you would like me to help you with?" I asked.

She replied that I could help prepare the evening meal, which I was pleased to do. After we had eaten I loaded the dishes into the dishwasher. By now I was feeling quite tired, so I said I would have an early night. I went to my bedroom and undressed, carefully folding my clothes as I took them off - something I would never have done as a boy.

I put on a nightdress and knickers and went to the bathroom. I sat on the loo to pee (as I had become used to) and wiped the end of my cock with toilet tissue when I had finished. I cleaned my teeth and realised that if I had been wearing make-up I would have had to remove it before getting into bed. Tomorrow perhaps?

Back in my room I snuggled into bed and was soon asleep.

The next morning I awoke and was almost immediately aware of the sensation of wearing a nightie and knickers. I got out of bed with a huge erection.

I was very disappointed to discover that I seemed not to be as supple as I had been the day before. I could no longer touch my cock with my tongue.

There was a glass on the table by my bed, so I spurted into that, milking every last drop of cum from my cock. I licked the tip of my middle finger and wiped the traces of cum from my cock, licking my finger and wiping again as my cock rapidly subsided.

Sucking my finger was a poor substitute for sucking a cock. But I could keep dipping my finger in the cum glass and licking it.

Finally I drank what was left in the glass before going for a shave and a shower.

I put on my underwear, stockings and a dress, then slipped on my shoes. I brushed my hair and went downstairs.

"Good morning, dear. You look very pretty!" said my Aunt. "What do you want to do today?"

I asked her to show me how to put on lipstick after breakfast and after we had eaten she did so. "Don't put too much on," she advised. "It should just make your lips a little more noticeable and emphasise the shape of them."

I helped with the housework, cleaning, ironing, and so on. Jobs that I had never considered doing in boy mode. But somehow, wearing a skirt and stockings, and being conscious of wearing a bra, gave me the patience to do what I realised were important tasks that were (in my experience) usually done uncomplainingly by a woman in the household.

By the time we had prepared and eaten our evening meal I was again tired and in need of an early night.

In the bedroom I took off my dress, watching in the full-length mirror as my underwear was revealed. I had left my shoes on and I realised that even the modest height of the heels accented the shape of my legs and bottom.

My cock was thrusting at the front of my knickers, demanding my attention. I tried unsuccessfully to reach it with my mouth and once again had to use my fingers and a glass to relieve the pressure and to consume the cum.

The holiday continued in a similar routine. I would have to deal with an erection every morning and evening.

I wore a dress or a skirt and top every day, always with bra, knickers, suspenders and stockings. I helped my Aunt with household duties. We would go shopping sometimes. I had my hair trimmed and styled a couple of times. I became confident walking around the shops and started to enjoy the sensation of having boys watch me and try to look up my skirt.

But I never went out in public without my Aunt.

And although I tried every day, I could never repeat the trick of putting my lips around my cock and I began to wonder whether it had really happened, even though the memory seemed so real.

The summer days flew by and it was suddenly the last day before I would have to go back to college. As we ate our evening meal, Aunt Carol said "I can see that your are comfortable wearing a skirt and stockings, but you have a long journey tomorrow, and I won't be travelling with you."

"I think you would be better to wear your jeans and boy clothes for the journey. You can take your new girls clothes with you and then decide whether whether you want to wear them at college or not."

"But, don't you remember?" I said. "My jeans don't fit me any more. My boy clothes were so tight that I couldn't fasten them properly and you had to find me some girl's clothes that would fit me..."

My Aunt laughed. "That's not how I remember it," she said.

"After the first night here you came down to breakfast in some of my daughter's clothes. I didn't mind you wearing female clothes but was determined that you should have some clothes of your own that fit you properly and not risk stretching my daughter's things."

As I thought back to that first day in a skirt, I remembered the look that flashed between the assistant in the bra department and my Aunt Carol.

A look that I now realised meant "You want to put this boy in a bra?"

I seemed to remember other exchanges of glances too. There must have been a number of sales assistants, hair stylists, etc that realised that I was not really a girl, but just a girly boy.

I felt a tear forming in my eye. Aunt Carol gave me a hug. "You make a pretty girl," she said, "and you've been such a help around the house. I'll miss you."

I could feel her breasts pressing against me and wished I had breasts of my own.

Up in my bedroom, despite my sadness, the sight of my reflection in the mirror as I undressed and the memory of Aunt Carol's breasts pressing against my body brought my cock to a throbbing erection, which I dealt with in the usual way.

The next morning too, I found that the sensation of wearing my silky nightie and knickers worked its usual magic.

In the bathroom I shaved my face and my legs before showering. Back in the bedroom, I dressed in my teen bra - the one with almost no padding - my suspender-belt and knickers, then carefully put on a pair of stockings. I put my boy shirt and jeans on over my feminine underwear.

They fitted perfectly - or at least as well as they ever had. They felt rather scruffy after the more elegant girls' clothes that I had become used to.