32A

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Romance between two x-dressers.
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G-String
G-String
52 Followers

I wake up in the middle of the night. I have psyched myself into such a state that I just can't go back to sleep. Thinking back over the years, everything started with a size 32A bra.

It happened on one morning when I just turned 13. In my locked bedroom, I clipped on a flimsy unpadded white cotton bra. I knew that I didn't need to wear one but I had been donning it occasionally since the age of nine, shortly after my mum left dad for another man.

I didn't know what went wrong between my parents. When they were still together so to speak, they were rarely home at the same time. They told me that they had dinner parties to attend, but apparently not together. I had no idea what mum did for a living, but she had lots and lots of very pretty dresses and she surely looked beautiful in them. When she went away, she left some unwanted clothes behind. At the time, I wondered if I was among the unwanted things in her life.

Dad told our amah to throw all mum's things into the bin but I secretly retrieved them, including that bra, and I had kept everything for myself. Her clothes were way too big for me but I secretly tried them at home. The amah caught me once and thought it was hilarious. But I told myself that I must be more careful in the future and I only wore them again behind my locked bedroom door.

I supposed that I shouldn't blame mum for leaving. Right after she disappeared, another woman joined dad in bed and they were soon married. I found out that she wore 34C. To me, she looked really clumsy on top!

Not long after they were married, I got kicked out of the house. I assumed that she considered me a bloody stumbling block. So I ended up living with my grandparents and they spoiled me rotten. Dad came about once or twice a month, sometime with that hateful woman in tow, to bring money and an occasional unwanted toy.

Well, enough of the background shit.

I remembered that it was a very special day, because I planned to wear a bra to school for the first time. I noticed that some girls in my class had started wearing them and I thought that perhaps it was time for me to do the same. Timidly, I clipped it on behind my back and pulled on the school shirt. I added a navy blue cardigan that I wouldn't normally wear. I checked myself in the mirror and I couldn't tell the difference. Good, I didn't want to be conspicuous. Otherwise, it would be most embarrassing.

At the school gate, I took a deep breath instantly feeling the added restraint around my chest. I looked around and nobody seemed to notice the difference. Suddenly, I felt great!

It was double Chinese history for the first morning session, the most boring subject. I sort of slouched over my desk and it was a miracle that I stayed awake. So it came as a relief when the bell chimed for the morning recess. I watched my classmates filed out of the classroom. As the last of them had left, I stretched my arms and yawned, again feeling the pull of the bra-straps.

"Why are you wearing a bra?"

Stunned, I turned and saw Jasmine who was sitting at her desk a column to my left and two rows behind. She sat diagonally opposite to the classroom door from me. No wonder that I had missed her.

"Don't know what you are talking about." I blurted out but felt a heat spreading on my cheeks.

Jasmine got up and walked slowly but menacingly over. Suddenly, she reached out a hand, pulled at the bra-strap that I thought was well hidden under my cardigan and shirt then let it snap back behind my left shoulder with a loud crack. It was a wicked joke that boys played with girls, but how dare she!

"Tell me what it is then, Steven."

I was busted! O.M.G. just imagine what my classmates would say if they found out. I turned beetroot and was worried sick.

"I..."

"Well, is that a bra you're wearing or not?"

A millions things rushed to my head and I didn't know what to say. I guessed that I must have nodded.

"So, aren't you going to tell me why you are wearing a bra?"

I looked up at her but couldn't find the right word.

"How did you find out?" I asked after a long pause.

"Well, first of all, you shouldn't slouch over your desk. The bra hooks showed under the cardigan at your back. Second, you don't normally wear a cardigan and today is not a particularly cold day. So I guessed that you must have put it on for a reason. And now I know that reason."

I was stunned but she continued.

"Don't worry. I checked the others sitting behind you. I don't think that they have noticed it, yet!"

I sighed in relief but then I was seized by an apprehension that Jasmine now held my embarrassing secret.

"You are not going to tell anyone are you? Please, Jasmine!" I begged her.

"Oh, no! I am not going to blackmail you, if that was what you were worrying about. If anything, I might even try to help you."

"I... I don't know what you mean..."

Puzzled, I looked at her. Jasmine was a repeater who joined our class this year. She was a big girl. Well, I didn't really mean big but she was very tall as she was taller than me by about five inches. At the time, she was 5'7" and I later found out that she was 10 months and 12 days older than me. She kept her hair short like, off the ears and off the collar. Even I grew my hair longer that she. She assumed a boyish manner and she didn't seem to have any friends. Came to think of it, if our classmates found out that I wore a bra, I wondered if I would have any friend left. Jasmine and I had been in the same class for almost half a year and we had not once talked to each other, until today. Now I looked closely at her for the first time. She could be quite pretty, but in a cool sort of way.

"Tell me first, do you like wearing girls' things."

I hesitated for a long time then nodded timidly. There was no point denying.

"Well, then perhaps I can give you a bit of help."

The bell chimed all of a sudden.

Jasmine snapped my bra-strap playfully again.

"Ouch! Stop it Jasmine, it hurts."

"Remember, sit up straight and don't slouch! We shall talk again at lunch." With that she walked back to her seat.

I spent the rest of the morning sitting like a ramrod, worrying sick what Jasmine might do with my secret. She could give an announcement to the whole class at any second and land me in the shit. Yet, I didn't go to the toilet to take off the bra. In any case, even if I took it off, I couldn't bear parting with it. It was part of mum's legacy. I had to keep it with me and it was liable to discovery...

Despite my worries, Jasmine did nothing.

The bell chimed for lunch and our classmates left in a hurry, leaving just Jasmine and I behind. I didn't dare to go. Now she had some sort of hold on me and I felt it improper to leave without her permission.

"So, are you going to tell me about it?" Jasmine started in a friendly and encouraging tone.

Red-faced, I told her the story from the retrieval of mum's legacy to being discovered in the ill-fitting dress by the amah and that I had tried some of mum's lipsticks and nail-vanish. Jasmine listened with fascination. To me, it was such an unexpected relief having finally told someone all about it.

"Jasmine, I just want you to know that I'm not a faggot. I... I just like wearing pretty dresses."

"Well, I have some really pretty dresses that should fit you. But what size of shoes do you ware?"

I told her and asked, "But why are you helping me?"

"I have my reasons. And I think you can be quite pretty when dressed up."

I looked at her, my face piping hot.

"Don't worry, I want to be your friend." She smiled.

And I wanted to believe her.

We talked through the whole lunch hour with just the two of us in the classroom and she shared half of her ham and egg sandwich with me.

"Promise that you will wear a bra and perhaps one of your mum's silky drawers tomorrow, will you?"

I looked at her sceptically.

"Don't you trust me? If I wanted to do something to hurt you, I would have done so already." She sounded as though she was pleading with me.

"Alright!" I nodded.

I kept tossing and turning in my bed that night. I was back safely in my sanctum and Jasmine had nothing on me now. If she decided to tell someone the following day, I could always deny it and call her a liar. Yet, I was curious where this was leading us.

Came the following morning, I clipped on an unpadded soft silk bra. I tugged my willy between my legs and wrapped it tightly with a matching pair of knickers until it gave the appearance of a flat crotch. As a result, however, I had to walk with an unnatural sway on the hips to ease the discomfort and I knew that I looked a sissy. I had practised that walk before and it gave me an odd sense of, being feminine. I didn't know why but I decided to put a pair of sponge bra-padding in a plastic bag and hid it among my books in the schoolbag.

I met Jasmine in the classroom. When no body was watching, I turned my back to her and slouched. She gave me a knowing wink in return. I sat in pins and needles the whole morning, pressing my thighs together, feeling the titillating squeeze of the silky underwear. I couldn't remember what was taught during the lessons. When it came to lunch, I could wait no more.

"Jasmine, I kept my side of the bargain. Yesterday, you said you would help me. What have you planned?"

"You'll soon find out."

"C'mon. Just give me a little hint, please!"

"No."

I begged her repeatedly but all she agreed to share with me was her sandwich.

The bell finally chimed at 3:45, and our classmates got up and left. Some of them turned and looked quizzically at Jasmine and I, as we were the only ones still fidgeting with our schoolbags. No doubt some of them would recall that Jasmine and I recently spent recesses and lunches together and would perhaps start wondering what we were up to. We were at that age very sensitive to goings-on between boys and girls! But Jasmine and I! Give me a break and don't be ridiculous! In any case, I was dying in anticipation, to find out what Jasmine had installed for me. When all the others had left, there was a brief awkward silence.

"See you on the 6th floor in five minutes," she said suddenly and walked out of the classroom.

The 6th floor was at the top of the teaching block where our science laboratories were located. It would be deserted at this time of the day. I struggled with myself - should I trust her or should I make a run? But she had done nothing to embarrass me. Well, nothing yet I reminded myself! I deliberated for a good five minutes and I was going crazy in my head. Finally, I made up my mind.

"Psst..."

I looked towards the sound and saw Jasmine poking her head out at the turn of the L-shaped corridor on 6th floor. Gingerly, I walked over to her.

"You surely took your time. I thought you weren't coming." For the first and perhaps the only time, she was angry with me.

"I..."

"You almost chickened out, right?"

I nodded shamefaced.

"C'mon," she waved and headed towards the female toilet.

"Wait Jasmine, where are we going?"

"Don't worry, I checked the whole floor and the floor below. There's no body around."

I thought to myself if I got caught in the girls' room then I would be in deep shit.

"C'mon, I've got something for you to try on." Seeing that I was still hesitating she added, "Don't you want to?"

I checked both directions on the corridor. There was nobody in sight. I nodded and followed her, my heart suddenly galloping. It was the first time I went inside a female toilet and I decided that I liked it better. It was cleaner and smelled fresher. In retrospect, I believed the janitor had just cleaned it up right after school.

She pointed at a cubicle and said, "In there".

When I got inside she said, "Now take off your uniform and I shall give you what's in here." She said as she patted on her schoolbag.

My face was turning red.

"You mean right here, right in front of you!"

"What's the matter? You will still be wearing your underwear. It is not as though I am going to see you starker. Remember, you wanted to try some dresses. I risk getting caught to be here with you."

"But..."

"But what?" She stared impatiently at me.

"I mean, could you at least turn around when I, uh, get undress..."

"You're really shy, aren't you?"

I pleaded with her but she shook her head.

"No. Take it as a form of training. You have to be brave if you are going to try my dresses. Either you do it now or I am leaving."

I sensed that she was getting angry again. I didn't want to upset her, especially not in my predicament. I gulped as I started to pull off my cardigan. I hesitated briefly before I unbuttoned my school shirt and took it off as well.

All I had on top was a pastel pink bra and my cheeks were on fire. I looked uncertainly at Jasmine, expecting mockery but seeing none. She just took my shirt and cardigan and helped folding them up neatly.

Shaking like a leaf, I turned my back to her as I fumbled with the buckle of my leather belt, unzipped my grey flannel and after some further hesitation I removed the last piece of my uniform. I checked myself to make sure that my willy was properly tugged out of sight before turning back to face Jasmine.

By then, I was standing in just mum's pink silk bra and knickers set, my white ankle socks and I had laced up my black leather shoes again. She studied me and her eyes seemed to linger a fraction longer at my flat crotch before checking the rest of me. Then she shook her head.

"No. That won't do. Take those off as well."

Stunned, I protested. "You said I could keep the underwear."

"I mean you should take off your shoes and socks, you silly bugger! They don't match the dress that I've prepared for you."

I grinned nervously and complied. Standing barefooted on the cold tiled floor, I felt queasy and my willy was straining to break cover!

"What happened to your, uh, thing? I was half expecting something sticking out in front." She pointed at my silk kickers.

I told her.

"I see. Now, hand those over and I shall give you your dress and shoes."

I had gone that far there was really no point protesting further. Jasmine took my trousers, shoes and socks and set them aside when she searched inside her schoolbag. My heart thumped as she pulled out a white pleated school dress, a black pair of Dr Martens T-Bar Mary Jane with shiny buckles and a brand new pair of knitted socks, still in its polythene packet.

"Now try them on."

Everyday, I saw girls in that school dress and I never dreamed that I could have a chance to wear it myself. I looked up at Jasmine in disbelief!

"C'mon, hurry up. We haven't got all day here."

"Thanks!" I muttered and stepped into the dress.

In her excitement, Jasmine helped me to zip up at the back. I clipped up the thin white cotton waist belt and thought the dress fit me perfectly.

Next, I took up the polythene packet. It was a pair of white knitted knee socks in crisscross pattern. It was not the regulation white ankle socks but I had seen girls in those with the legs rolled down to ankles in school, only to pull them up after they had left the school perimeters. And I thought girls looked really pretty in them.

"Jasmine, you bought this brand new for me."

"No, you silly bugger! My mum bought it for me but I didn't like it. It's just not my style. Now would you please hurry up?"

I unwrapped the packet and Jasmine threw the packing into a small lidded-bin by the toilet seat. I was so naive at the time that I kept wondering why people put bins in the toilet, just so that girls could discard the wrappings of their pretty socks? As Jasmine was waiting impatiently, I pulled the socks up my calves. Suddenly, I felt so pretty. However, at the same time I also sensed that I was getting an erection and my thingie was feeling really uncomfortable, trapped in the tight pair of knickers. And it would be most embarrassing if my thingie sprang out unexpectedly from its confinement!

"Well, what are you waiting for? Put the shoes on. It's size 37 just as you said and I hope that they fit."

I smoothed the dress under me, as I had seen girls do so often in the classroom and sat on the toilet seat before slipping my stockinged feet into her shoes. They were not new. Jasmine probably wore them until her feet grew too big for them. I buckled up and they felt quit comfortable.

"How do I look?" I asked feeling more excited than embarrassed now.

"Not bad, for a boy..." she said as she gazed down at my flat chest.

"Oh, I forgot these."

I fished out the two sponge pads from my schoolbags and showed them to her.

"Great, let me unzip you at the back and you can put them in."

I gave her a mischievous grin, turned my back to her again as I stuffed the sponge pads inside the silk bra-cups.

"Done, can you zip me up again?"

"Sure, but you'll have to learn doing it all by yourself soon."

I heard the zip coming up and immediately felt a tightening around my 'bosom'. I had no idea but it was such a wonderful feeling! Jasmine fumbled a bit at the nape of my neck that I later discovered was a tiny hook, holding the collar together. When I turned around, Jasmine whistled.

"You look really... attractive. Now, I can't call you Steven any more can I, with those!" She made a gesture with her palms, imitating my bosom that looked more curvy that hers. "Well, I shall call you Cindy. How 'bout that?"

"Cindy sounds fine to me. Thank you, Jasmine. But how do I look really?"

"How 'bout if we go to the changing room by the gym and you can check it out on the full-length mirror there?"

"It's such a drag, having to get changed all over again and again. And what if there was somebody there?"

"Who said you were going to get changed?" She said.

I looked around and suddenly realized that she had put all my clothes away.

"Jasmine, give me back my clothes. I can't go out like this. Please!"

"Of course you can. You look more like a girl than me."

"Don't be ridiculous. Give me back my clothes, oh please!"

"Look yourself in the mirror and tell me that you don't look at least as pretty as any girl in our class."

I checked the mirror abov the hand basin. She was right. Not bad if I were a girl. I fidgeted with my hair. It almost reached the shoulder and covered the ears but the styling was wrong. I combed it a bit with my fingertips but it still didn't look right. Jasmine took a comb and pulled my hair over the forehead and fringed my cheeks.

"How's that?" She smiled encouragingly.

"No, I better get changed."

"I already said no. Now either you come with me or you stay here on your own."

She grabbed both our schoolbags and made for the door. I tried to stop her but she shrugged off my hand and was suddenly gone, leaving me behind.

I panicked, checked my face again in the mirror and immediately dashed out of the girls' room. I was petrified that Jasmine would leave me like this, but she was waiting outside.

"You have thought of everything, haven't you? You planned it and you tricked me."

"What did you say?"

I thought she would be angry but she looked hurt instead.

"Jasmine, I... I'm just scared."

"You still don't trust me?"

I look at her and I finally understood.

"Of course, I trust you. I'm sorry."

She smiled and said, "Let's go then."

Gingerly, I followed closely behind her steps. We took the central staircase cautiously down the floors. As we approached the 1st floor, we saw light from the staff office. We didn't wait around to be discovered but hurried down the stairs. Instantly, I became aware of the bellowing of the dress. It felt kind of strange. I had seen girls pressing down their dresses in the wind and I did the same.

Quietly, we slipped into the female changing room. There was a full-length mirror by the door and I saw Cindy for the first time and Cindy looked really lovely and if I might add, quite attractive in her uniform.

G-String
G-String
52 Followers