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I should explain that in this story, words spoken by women are in UPPER CASE.
Upper. As in Superior!
Now read on...
I had finished the first year at University. Originally the plan had been for me to stay with my girl-friend's family while my parents were on their cruise, but we had had a blazing row and it seemed our relationship was over. Fortunately my aunt had plenty of room in her house now that her daughter had moved out to a place of her own.
That's how I came to be staying with her.
"DID YOU THINK I WOULDN'T NOTICE?"
I now realised that the pile of underwear hadn't been left there accidentally.
A trap had been set and I hadn't been able to resist the bait.
As I had walked past her bedroom, I had seen the knickers through the open door. There was a pile of them in various colours.
I knew that she was out of the house, so it was obviously safe just to go into the room to have a closer look. To see what sort of knickers she wore. And to touch them.
They all seemed to be of a similar style. Big knickers. Not tiny bikinis or thongs. In soft, silky nylon. Trimmed with lace or with little frills around the leg-holes.
Of course, it was necessary to lift up the top ones so that I could inspect the pairs beneath.
My cock had started to stiffen. I had wondered what they would feel like to wear. There were about a dozen pairs in the pile.
She wouldn't notice if one pair went missing, would she? I could maybe sneak them into the laundry basket later.
I had better take a pair from the middle of the pile. She might remember which ones were on top.
"ARE YOU WEARING THEM NOW?"
I could feel my cock shrinking, shrivelling down to almost nothing.
Only a few minutes ago it was rock-hard, straining at the front of the lovely pink knickers. Then I had heard her key in the front door and had to quickly put my jeans on and make my way downstairs.
She had gone to her bedroom and quickly returned to accuse me.
I realised that she had only gone upstairs to see if the bait had been taken.
"SHOW ME."
It hadn't been necessary for me to answer. She knew. She stood there frowning, legs apart, arms crossed. A strong woman. Although I was nearly twenty, I realised that she was a more powerful personality that I was.
Nervously I unfastened my jeans and let them drop.
She smirked.
"NOT VERY WELL-ENDOWED, ARE YOU? HARDLY A BULGE."
"NO WONDER YOU WANT TO WEAR PINK KNICKERS. THEY MAKE YOU FEEL EVEN MORE LIKE A GIRL, DO THEY?"
I could feel myself blushing. I almost wanted to deny this.
But I wasn't able to speak the words.
To claim that I did have a proper cock. A cock that was rather large only a short while ago.
To admit that putting the knickers on had caused a huge erection. An unmistakeable bulge.
There was no evidence of this now, under her steely gaze.
"WELL GIRLS DON'T ONLY WEAR KNICKERS. THEY HAVE OTHER ITEMS OF UNDERWEAR AS WELL. COME ON, I'LL SHOW YOU."
"YOU CAN LEAVE YOUR JEANS THERE ON THE FLOOR."
I stepped out of them and followed her up to her bedroom.
Wearing her pink knickers.
She indicated that I was to remove my shirt. Now I was standing there in front of her wearing only a pair of knickers.
She put me into a bra. It didn't really have cups, just a little padding.
It didn't occur to me at the time, but looking back she must have bought it specially for me. The bra would never have fitted her shapely bust.
She must have been confident that the trap would work, that the bait would be taken.
"NOW PULL YOUR STOMACH IN."
I had to pull the waist of my knickers down a little way as she fastened the suspender-belt. Then she pulled the back laces tight and tied them in a bow.
"YOUR SUSPENDERS MUST GO INSIDE YOUR KNICKERS"
I threaded the suspenders down through the leg-holes of my knickers. She was watching me intently. Intimidatingly. There was no increase in the size of the bulge in my knickers.
She showed me how to put the first stocking on and fasten in to the three suspender clasps. Then she let me put the other stocking on myself. She adjusted all the suspenders so that they were taut.
She gave me my shirt to put on. And led me back downstairs.
It was a strange sensation wearing stockings and suspenders. The suspenders pulled on the taut stocking-tops with each step.
There was a little tingling sensation in the end of my cock, but I couldn't feel any swelling.
She was standing at the foot of the stairs now. Watching me descend the stairs. In my knickers and stockings.
I put my jeans back on. I needed to fasten my belt another notch now that my waist had been tightly laced in my suspender-belt.
I guess that had been bought specially for me as well.
"COME ON. WE NEED TO DO SOME SHOPPING."
I didn't try to resist. At least I had my shirt and jeans on. No-one would know I was wearing feminine underwear.
I slipped my feet into my sneakers. They slid in easily as they were encased in nylon stockings.
As we were getting to the front door a caught sight of my reflection in a mirror. My jeans seemed to be the wrong size now. They were bunched round my cinched waist and this made my bottom look bigger. It almost looked like a girl was wearing jeans intended for a boy.
Although I could feel that I was wearing a bra, It didn't alter the shape of my chest. No-one would know.
We went to the supermarket to buy food. I pushed the shopping-trolley while my aunt selected items to buy.
I was still very conscious of the sensations of wearing my underwear. The tight lacing round my waist. The gently insistent grip of my bra straps. the tugging of suspenders on stockings. And the gentle support of my knickers encasing my cock and balls. And sliding on my bum, the silky fabric caressing my bottom.
I was quite enjoying it. But not getting an erection.
Not while I was with her.
We took the shopping back to the car and I thought that we would be returning home. But no. My aunt led me over to a clothes store.
Women's clothes were on the ground floor, and the men's department was on the upper floor. We didn't go up there.
She was looking round various racks of dresses and I assumed (rather naively, now that I think back) that she was looking for something to wear herself.
But then she picked a red dress off a rack and held it up against me.
This was rather a shock. Not just because she might be getting a dress for me.
But there were several other women in the store who could see us.
Who could see that the dress she was looking at was intended for me and not her.
"LET'S GO AND TRY IT ON."
I gasped. Surely she didn't mean it. But I didn't want to attract even more attention by making a fuss. So I followed her across to the fitting rooms.
The assistant looked at my aunt rather questioningly as I was accompanying her, but my aunt just nodded and the woman let us both in. Once inside the changing-room she indicated that I was to remove my jeans and shirt.
She helped me into the dress. It had a long zip at the back. My bra only gave me the slightest hint of a bust. The skirt came just above my knee.
But while I was looking at my reflection my aunt had picked up my shirt and jeans and was already leaving the changing-room.
Not wanting to be left there on my own I quickly put my sneakers on and followed her.
"HE IS GOING TO KEEP IT ON."
The assistant looked a little surprised. Probably most customers didn't do that.
Especially boys.
But she removed the price label from the dress and led us over to a cash till. Fortunately there was no queue.
I was anxious to leave the shopping area as quickly as possible and get back to the car.
But my aunt didn't seem in too much of a hurry. In fact, she took us into a shoe shop.
We were served by an assistant. A girl of about my age. She measured my feet and went to fetch some shoes of the right size. Black ones. With two-and a half each heels. That's what my aunt said I needed.
I very quickly realised how tricky it was to try on shoes in a skirt.
Keeping my legs together. With the salesgirl kneeling in front of me.
She would probably see that I was wearing stockings.
But would she see my knickers?
I tried walking in the shoes. They actually felt quite comfortable and natural to wear. Quite a relief as I didn't want it to be obvious that I had never worn heels before.
I wasn't all that surprised that my aunt asked the girl to wrap my sneakers. I would be wearing the shoes to leave the shop.
We walked slowly back to the car. It was starting to get dark now. Less chance of anyone recognising me.
"DON'T WORRY. EVEN IF SHE DID SEE UP YOUR SKIRT, THERE'S ONLY A TINY BULGE IN YOUR KNICKERS."
Which was more embarrassing? For her to see that I was a boy wearing knickers?
Or for her to see that there was only a tiny bulge in them?
When we got home I had a good look at my reflection in the hall mirror. I liked the way my shoes changed the shape of my legs. And made my bottom more prominent. The dress fitted me well. I liked it. I had the appearance of a rather flat-chested girl.
From the neck down. My head and face still looked rather male.
"WE'LL SORT YOUR HAIR OUT TOMORROW."
She ordered pizza for us both. I think this was just so that I would have to answer the door to accept the delivery. In my dress and heels. I tried to smile sweetly. To look as much like a girl as possible.
Even though I didn't know the delivery guy I didn't want him to think I was a boy in a dress.
She showed me how to use both hands to smooth my dress under my bottom as I sat down to eat. We had some wine. I started to relax a little.
But still no erection. I wasn't feeling that comfortable yet.
We watched television for a while after eating. There wasn't really any conversation.
"GO AND HAVE A RELAXING BATH BEFORE GOING TO BED. AND SHAVE YOUR LEGS WHILE YOU SOAK."
I looked at my stockinged legs. They weren't very hairy, but I could see that they weren't completely hairless. She came with me up to my bedroom and helped me undress. Then she started running a bath, adding some bubble bath. She handed me a lady's razor and left me to it.
I shaved my legs. Then I continued to remove all my pubic hair, also shaving the cheeks of my bottom and between my cheeks. I shaved my underarms and what little hair there was on my chest. I dried myself on a large towel that my aunt had left for me. Before leaving the bathroom I rinsed the remaining foam and bits of hair from the bath.
I went into the bedroom. She was waiting for me. I saw that a short nightie with matching knickers was lying on the bed.
She handed me a glass.
"I DON'T WANT ANY STICKY MESS ANYWHERE. IF YOU ARE GOING TO PLAY WITH YOURSELF, DO IT INTO THIS RECYCLE GLASS. AND THEN SWALLOW IT ALL."
"PEOPLE OF YOUR AGE WHO WEAR SKIRTS SOON GET USED TO THE TASTE."
She smirked and left the room. I finished drying myself and then put on the nightie. By the time I had pulled up my knickers I had a huge erection.
Like the one I had this morning. It seemed a long time ago. So much had happened since.
But my cock had not stiffened at all during the day. My predicament - her presence - had prevented it.
But now I was alone again. With a smooth hairless body. And wearing beautifully soft silky knickers.
I only just got the glass in place before my whole body jerked as I pumped what seemed a large volume of cum into it.
I swallowed obediently. Now I felt very tired. I was soon asleep.
I woke up. Although the curtains were closed I could tell that it was a sunny morning.
My hand reached for my cock, as boys do when they wake up.
When my fingers touched my silky knickers the memories of the day before came flooding back.
How my aunt had got me dressed in girls clothes.
Just because I hadn't been able to resist borrowing a pair of her knickers.
My cock was very hard now and likely to gush at any moment. I got out of bed.
Fortunately the recycle glass was on the bedside table. I managed to get it in place just in time to avoid making a sticky mess.
I put my soft cock back in my knickers and drank the contents of the glass. A strange taste. But one that was already starting to seem familiar.
I could hear my aunt in the kitchen. She was probably laying the table for breakfast. So although I had been tempted to get back into bed, I thought that I had better get shaved and showered. I took off my nightie and knickers, wrapped a towel round my waist, and went to the bathroom.
By the time I returned to the bedroom, my aunt was waiting for me. She handed me a clean pair of pink knickers.
"HERE YOU ARE. PUT THESE ON AND LET'S SEE IF YOU CAN MANAGE THE OTHER ITEMS."
I turned my back to her as I stepped into the knickers and pulled them up. I managed to fasten the suspender-belt and tighten the laces without any problem. Fastening the bra behind my back was more tricky, but I managed it. Then I put on my stockings and fastened them to the suspenders.
It almost seemed part of a normal routine.
She then handed me a burgundy coloured slip. it had broad shoulder straps. I suppose you could say there was room for growth in the bust area. It was just long enough to cover my stocking-tops.
The back zip on the dress was more of a challenge. She had to help me. Obviously more practice needed.
It felt good having a slip under the dress, especially when I put my heels on.
There were now two layers of silky material between my dress and my bottom.
"IN FUTURE YOU MUST WASH YOUR STOCKINGS AND KNICKERS EACH NIGHT, AND HANG THEM UP IN THE BATHROOM TO DRY."
She pointed to a plastic device on the dressing table. It was a bit like a coat-hanger only smaller and with four arms instead of two. At the end of each arm was a clip like a spring clothes-peg. I could see that if you fastened your washed knickers to two diagonally opposite clips and a washed stocking to each of the others it would be perfectly balanced. Very neat. And I guessed the underwear would dry overnight quite easily.
She led the way downstairs. A light breakfast had been prepared. Not much was spoken as we ate.
I was rather nervous at the prospect of going out in public in a skirt and heels in broad daylight. At least we were not in my home town. Hopefully I wouldn't meet anyone who knew me.
It was still quite early and there weren't too many people on the street as we strolled arm-in-arm to the shops. I needed the reassurance of someone to cling on to. Wearing a slip added an extra dimension to the sensations of walking.
That extra layer of silky material seemed to caress my knicker-clad bottom with every step. I was getting used to the feel of suspenders tugging on taut stocking-tops as I walked.
I liked these sensations. It was as if my underwear was constantly reminding me that it was there.
That I was wearing feminine items quite unlike anything a normal boy would wear.
I saw a young woman pushing a pram. It occurred to me that although I too was wearing a skirt, I could not ever give birth. I didn't have the right anatomy.
But then my thoughts progressed to how she had got pregnant. How she must have opened her legs to welcome her partners cock into her body.
And although I didn't have a vagina, I suddenly had a vision of myself in that position. My stockinged knees touching my bra to allow my husband access between my legs, his long hard cock pumping deep into my body...
"COME ON. THIS WAY."
It was a jolt back to reality as we entered the beauty salon. It was clear that my aunt was well-known at the salon. A knowing glance passed between her and the manageress of the salon, who led us to a private area at the rear of the establishment.
"MAKE HIM AS PRETTY AS YOU CAN"
No pretence there then. But the manageress could see that I was a boy in a dress.
She smiled sweetly. "Would you like a drink, dear?" she asked. I nodded. "Hot chocolate OK?"
"Yes, please," I replied. My aunt said she would leave me in capable hands and come and pick me up later. When the lady returned with my drink, my aunt nodded to her and left. I sipped the drink. It was very comforting.
I realise now that there must have been something in it, because I became very sleepy...
I woke up to find that my nails were being manicured. "Did you have a nice sleep, dear?" the lady asked in a friendly voice. "I guess you must have been rather tired. I'm glad you've woken now though, because I need you awake to put your lipstick on. You're more or less finished otherwise."
I looked at my refection in the mirror. Was that really me? Blonde highlights in my hair. Quite a feminine style. Elegant eyebrows. A hint of colour on my eyelids and of rouge on my cheeks. Pink stud earrings - I suddenly could feel that my ears had been pierced. My aunt came back in just as the lady had finished my lips.
"QUITE AN IMPROVEMENT. MUCH MORE GIRLY NOW."
I suppose this was a compliment. But I wasn't sure if she was speaking to me or to the salon lady.
We didn't go straight home. We went back to the main shopping area. There were a lot more people around now. A clock started chiming. It was midday. I must have been in the salon for well over two hours.
We went back to the dress shop. This time my aunt gestured towards the racks of dresses. It seemed I was to choose. I looked at several before picking out a black dress. It was a few inches shorter than the one I was wearing. My aunt seemed to approve and we went to the fitting room to check the size.
On the way to the cash till she picked up a couple of packs of black stockings.
We had some lunch in town. I was quite hungry by this stage. Then we made our way home.
"WHY DON'T YOU GO UPSTAIRS AND CHANGE INTO YOUR LITTLE BLACK DRESS?"
"AND PUT A PAIR OF BLACK STOCKINGS ON."
I went up to my bedroom. I struggled to get the back zip undone on the dress I was wearing. But I was slowly getting better at reaching behind my back.
I removed my tan stockings and put on a black pair. The shiny black stocking-tops showed below the hem of my slip and looked a little tarty.
Before putting on my new dress I went to the bathroom and washed the stockings I had just taken off. Then I hung them up to dry.
I returned to the bedroom and took out the new black dress. It had some labels on that I had to remove. I put it on. I realised that it was quite a lot shorter than the red dress. Much more of my legs were on display. But they were rather nice legs when I had my heels on. I made my way downstairs.
I had only just arrived at the lounge when the front door bell rang.
"COULD YOU SEE WHO THAT IS AT THE DOOR?"
I glanced at the hall mirror for reassurance. Nice hair. Perfect makeup. I smoothed down my skirt to be sure that my stocking-tops were properly covered. Then I opened the front door.
My heart suddenly started pounding. The visitors were my ex-girl-friend and my cousin.
They giggled.
But I realised that they were expecting it to be me opening the door.
And they already knew I would be wearing women's clothes.
I stepped back as they walked in.
"Who's a pretty boy, then?" laughed my ex.
I had been set-up.
I hadn't known that my ex knew my cousin. But obviously this had been planned.
Revenge.
With my aunt as an accomplice.
We were all in the lounge now. I looked nervously at each of the smiling females in turn. We were all wearing dresses.
But there was something noticeably different about one of us. They all had breasts. And I didn't.
Each of them had well-rounded lady lumps and I had a flat chest.
I realised that I really, really wanted tits. Boobies to justify wearing a bra. A well-filled bra to go with my knickers and stockings.
And despite my predicament, I couldn't help myself. I got an erection.
And they noticed.
I could see the way they kept glancing at the front of my skirt.
"SHOW US YOUR KNICKERS, THEN."
For a moment I thought of refusing. But it was obvious that I had an erection anyway. And there were three of them.
Three strong females against a boy in a frock.
I lifted my skirt and the front of my slip. I could feel my throbbing cock pushing against my pretty knickers. I couldn't see it, but they all had a perfect viewpoint.
I could see there was a mixture of amusement and admiration.
My ex was especially pleased with what she saw. She took photos on her mobile phone.
She had planned her revenge and was now milking the situation.
Literally.
She had pulled my knickers down and had a glass in one hand. The other two watched approvingly.
She handed me the glass and tucked my now shrivelled cock back in my knickers.
"GOOD GIRLS SWALLOW."
"OR AT LEAST THAT'S WHAT YOU TOLD ME."
I was a good girl.
Although she insisted I licked the glass clean.
I rearranged my clothes.
Blushing.
Embarrassed.
Two of my female relatives had just been watching my girl-friend tossing me off while I was wearing a dress and women's underwear.
"ARE WE FRIENDS AGAIN NOW?"
I nodded and she gave me a hug. Her breasts pressed against my body. I think she knew the effect they had.
She cupped my lightly padded bra with her hand. She looked across at my aunt, who nodded.
"I looked at silicon falsies on the internet," she said. "Good ones are rather expensive. Only worth spending that amount if they are going to be worn all the time."
The three of them turned to look at me. It was a big decision. A life-changing moment.
It was no use denying that I liked wearing the clothes. They had all seen me. They knew. And they would still know if I refused the offer.
Word might get around.
But deep down I knew that it was what I wanted. And might never get the opportunity again.
And so it was that I acquired a pair of bouncy prosthetic boobies. And a couple of new bras to put them in. To support the extra weight on my chest.
Apart from the bras, my other clothes still fitted. They hadn't been intended for flat-chested people anyway.
And there were several more shopping trips to buy more clothes.
A few short weeks later I went off to university with my girl-friend. We had already planned to share a flat together, so that arrangement didn't need to be changed.
My aunt drove us there and my cousin came too to see us off.
They were all wearing jeans. Tight jeans. No bulges in the crotch area.
I was the only one in a skirt.
I didn't have much of a bulge in the crotch area either. My cock was locked inside a tiny pink plastic chastity device. In case of embarrassing cock-ups in public, my girl-friend had explained. I didn't have to wear it when we were alone in the flat together.
And she had the key. On a thin gold chain around her neck.
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