Dan The New Girl Ch. 02

Story Info
Lingerie shopping is challenging for new girls... and boys.
2.5k words
4.52
43.6k
23

Part 2 of the 3 part series

Updated 06/08/2023
Created 01/12/2018
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"OK, Dani, take off my knickers, choose a fresh pair from the drawer, and let's get you dressed," said Lucy.

Dan sat up in bed. He was wearing a tight fitting white bra and Lucy's knickers - the ones he had pulled down Lucy's legs before he had plunged his throbbing cock into her wet and inviting cunt. The night before. When he had been a boy.

Now everything had changed. He had been tricked into putting on a bra that had magically and instantly turned him into a girl.

He had been a six foot shy guy. Short hair, broad shoulders, tolerably good looking. A bit uneasy around other guys, always preferred to spend time with girls. Dan has always been straight. He'd never questioned his sexuality, and had been with maybe ten or twenty girls - some long term girlfriends, some short flings, and a few one night stands when he'd been feeling courageous. Like last night. Except... nothing he'd experienced or imagined had ever turned out like this.

Now he was a five foot two pretty little blonde girl. His whole body had changed, and everything felt confusing and new. His vision was flanked by soft wavy blonde hair. He had to flick it aside or push it over his shoulder to stop it getting in the way. And his body was petite, willowy and delicate. He had the body of a lingerie model, simple as that. Slim waist, flat belly, a perfect pair of tits (though he hadn't seen them without a bra on yet), and a cute little butt with gorgeously smooth legs.

He did what he was told. He pulled his knickers down. He felt terribly shy doing it in front of Lucy. And Lucy was staring hard at him. "Now go and choose some knickers from the drawer," she commanded.

Which panties? The selection was bewildering. He could feel Lucy's eyes burning into him, so he made a quick choice. He pulled out a pair of white ones, to match his bra. "Are these OK?" he asked meekly.

"Not the most exciting choice, but they'll do fine. Put them on."

Once they were on, Lucy told him to get dressed. "For now, you can wear my clothes, but we're going shopping as soon as you're decent, so get on with it."

It was all way too intimidating to spend time choosing. He grabbed a pair of jeans and a white blouse.

He put the blouse on first because he was so painfully conscious of his breasts. And Lucy would not stop staring at them. As soon as he started buttoning up the front, he began to relax. The shirt was a little tight around the chest, so for the first time in his life he had to push his boobs together to fasten the buttons between his cleavage. It felt, and looked, so good. In fact... was he starting to feel his pussy getting wet?

"Oh my God, Dani, you've pissed yourself!" said Lucy, laughing.

Dan's quim tightened immediately. Sure enough, he could feel his knickers were soaked. He thought he was getting aroused, but actually he had just let go of some muscle in his vagina that he'd never had before. And, as soon as he had been conscious of this, he had stopped himself. Totally unlike a man! He had stopped in mid flow.

"Go to the bathroom and clean yourself up. You are going to need some serious training, girl, I can see that!"

He could feel his cheeks burning. Fortunately, he'd stopped himself before any piss had run down his inner thighs, but his panties were wet through. He ran to the en suite, shut the door behind him, pulled his knickers down and threw them in the sink. He lifted the seat of the loo and stood in front of it, looking down. Oh. No penis, of course, just a few pubes and the beautiful horizon of his pussy. And now, an undoubtable and urgent need to pee. He pulled the seat down and sat on it like a girl. Immediately he let loose a stream of piss straight down into the bowl. "Good girl," called Lucy from the bedroom. That felt great. Delicious relief, plus a unique tingling feeling in his vagina. He wiped carefully afterwards. From front to back, right? Like a good girl.

When he came out, Lucy had selected some new knickers for him. She held them out in one hand, with the other hand behind her back. "Put these on," she said, "... and then put this on." And she revealed what was in her other hand: a panty liner.

"What? Why?" asked Dan.

"Because I can't trust you not to piss yourself again - even a few drops," said Lucy. She cocked her head slightly. "Oh come on, don't be such a startled lamb. You've got a vagina now, honey, and I can't expect you to know how to use it yet. Every girl wears pads sometimes. I just don't want to... risk my jeans on you."

So, with his knickers between his knees, Lucy showed Dan how to place the pad and wrap the wings around. He felt self-conscious when it was on - especially because of the wings folded over between his legs, but Lucy assured him it was on fine and now he should just forget about it.

Lucy chose some ankle socks and a pair of Converse to complete his outfit. And before long they were ready to go. "Where are we going?" he asked.

"Shopping, dummy. You think we're going to share clothes forever?"

That meant going outside. Where people could see him. Instinctively Dan felt worried about that. Would they know he's not a real girl? He grabbed a little cropped jacket as they left, hoping to be less exposed.

*

The journey to the shopping mall was weird for Dan. He didn't know how to walk. He had no idea what to do with his chest. If he hunched his shoulders to hide his boobs, that felt more safe. But when he did, Lucy poked him in the back and said, "Shoulders back, girl. They're great tits, don't be ashamed of them."

People were looking. They clearly had no idea what was going on inside that little blonde girl's head. But a lot of them knew a great body when they saw one.

"People are staring," he said.

"Yup," she said.

At the mall, they went straight for a department store and took the escalator up to the lingerie department. "Let's get you measured first," said Lucy.

Dan grabbed Lucy's arm and whispered, "But you told me I can't take this bra off. Won't I just turn back to a boy?"

"Oh yes. Good point. That'll be fun. Come on!"

"Nooooo!" Dan suddenly felt ultra-conscious of his body. There's no way he was ready to leave it.

"OK, sweetie, let me explain how this works. You've been wearing that bra for, what, a couple of hours now? For every hour you wear it, you're OK to take it off for ten minutes."

"So I can take it off for twenty minutes and I won't change?"

"Mmm, hmm," she said casually, as if it really didn't matter either way.

Dan quickly did the maths in his head. He'd actually put the bra on less than an hour after he'd woken up that morning, and it was now late afternoon... so that's maybe six hours... so that's maybe sixty minutes he could go braless. But he didn't want to admit that he had been so quick about jumping into Lucy's underwear. He coyly asked if, theoretically, he'd been wearing it for, say, six hours...

"Oh, so you jumped into my lingerie the second you thought you were on your own, huh? You're a cheeky one, aren't you!"

Again, Lucy had made Dan blush to his roots.

"Your safe, sweetie. You can get those babes out and your cleavage will stay smooth and hairless, don't you worry." She stroked her hand along his side, swiftly gave his left tit a little squeeze, and winked.

So Dan queued at the bra fitting room in the lingerie department.

A tall business-like Scandinavian woman picked him up. "Hi, I'd like someone to check my bra size, please?"

"This way." Dan looked at Lucy. She gestured to him to go by himself. Suddenly he was alone in a brightly lit cubicle and his body was the only subject of conversation.

"What is your dress measurement?"

"Uh... I don't know... I think... a 10?"

"You're not a 10. Take your clothes off."

"No, I can't!" squealed Dan, immediately thinking of his pad, let alone getting naked with this stranger.

"Don't be silly."

"No, really... I..."

"Ugh!" the attendant did not attempt to hide her distaste. "You're an 8. Now, take your top off."

He unbuttoned as quickly as he could, fumbling with nervousness.

"Not your bra. Leave that on for now. Lift your arms up."

She pulled a coiled measuring tape from her own breast pocket and unravelled it. It was looped with a clasp at one end so that she could hoop it over his head, and then cinch it up under his boobs where his bra strap lay.

"32..." she said, loosened the tape and placed it carefully around his breasts. She pulled, and it tightened.

She held him with the measuring tape around the fullest part of his breasts. She pulled it again, slightly, like a leash, encouraging a dog to come. It tightened, squeezing, and he drew breath a little. Stepped towards her to keep his balance. He looked up at her, towering over him.

"What size bra were you when you were a boy, hmm? 38A? 40B? I don't know why men don't wear a bra in public more. They're essential, don't you think?"

He was stunned. A silence stretched out between them.

She knew! How did she know?

And then she switched back into ultra-efficient business mode.

She checked the bra he was wearing, putting a couple of fingers under the back strap. Then the same at the front on the shoulder straps, checking the tension. "This bra is just right for you. Perfect fit. What size is this?"

Dan had no idea. "Uh, I don't know."

"You don't know? You're crazy. You put it on this morning and now you don't know the size of the bra you're wearing? Take it off. Let's have a look."

Dan hesitated. "Do I have to??"

"Yes, you do. Take your bra off and give it to me." The attendant held out her hand like a teacher about to confiscate something.

There was nothing for it. Dan reached around behind his back and fumbled for the clasp. He let the strap ping open and shrugged the bra off his shoulders.

For the first time, he had his breasts out and he handed the attendant his bra.

She looked at it. "No label. I see." She looked at him. "You have very nice breasts. I wish mine were more like yours."

Dan looked in the mirror opposite him. He looked amazing. His boobs were perfect. Slightly side set, soft and pert, not at all saggy. They had a slight crease underneath, without being an ugly fold. And his nipples. Oh, they were round and pink like perfect targets. So much bigger than his pointless little boy nipples. Just looking at them made him ache to have them fingered and sucked. They were already puckering slightly and becoming erect just from being mentioned.

"Wait there," said the attendant and slipped out the door.

Dan filled a few moments looking at himself in the mirror. Checking his breasts from various angles. And feeling them. They felt so good in his hands as he gently squeezed and explored them. The nipples were incredibly sensitive. By the time the attendant came back, they were fully erect. Dan dropped his hands to his sides awkwardly, and blushed, again.

"Try these. You are a 32C." The attendant had brought a selection of bras on hangers for him to choose from, all his size.

Lucy called from outside. "How are you doing in there? I'm bored!"

"You can come in," said the attendant.

Dan was in the middle of putting on a grey satin bra with pink detailing as Lucy burst in. He jumped and clutched the bra to his chest to avoid showing his nipples.

"Oh come on, babe, don't be shy!" Lucy laughed. The attendant laughed too. They were both looking at him. "We've all seen it all before."

"Yes," said the attendant, "Just nipples between friends, hmm?"

Dan still felt awkward, and reached behind his back to do up the bra. It was pinching one of his breasts, so he stuck his hand into each of the cups in turn and pulled his boobs into place.

"Let's get this one," he said hurriedly. "But can I have my old bra back please?"

"Ah, of course. I took it with me when I went to make a selection for you. One moment please."

Oh no! thought Dan. You better not have lost the bra that will keep me in this body!

Without thinking about what he was doing, he followed the attendant out into the store. He suddenly found himself in a public place, wearing just jeans and a bra with the price tag dangling under his arm. And sure enough, just outside the fitting room, there were three men, clearly waiting for their partners inside.

So awkward. Dan put his arm across his chest, as all three pairs of eyes bored into him, checking his tits before their civility had a chance to kick in.

"Here you are," said the attendant, handing Dan his original white bra, which had been hanging by a shoulder strap on the Returns rail of all places. He grabbed it and disappeared back into the fitting room.

"Well that was embarrassing," he mumbled to Lucy as they paid for Dan's new lingerie. Lucy had persuaded him to buy a few more items: another bra, a few pairs of knickers, some tights, a pair of hold-ups.

"Oh don't worry about it. It's all part of being a woman. There's far worse to come, believe me babe."

"Let's just get you an LBD and we can go home."

They spent an hour finding Dan the perfect Little Black Dress. He rejected a few choices because they were too revealing, especially the low back one that Lucy selected for him. "I'm not having men staring at my bra strap, and I'm certainly not ready to go braless."

On their way out, a man looked Dan up and down. He didn't look like a perv or a creep, but it was 100% clear what he was thinking. "Hey beautiful, you wanna go to the pictures tonight?"

Dan clutched Lucy's arm. There was no way he was ready for that. He was suddenly glad of the pad he was wearing, as a tiny drop of pee squeezed. He clenched his pelvic muscles tightly and made an involuntary squeak - like a little girl. Lucy laughed. "Don't you worry about him, babes. You're mine." She said it loud enough that the man could hear them. Dan hung tight to Lucy's arm, flinching slightly, and they headed home.

End of part two

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
willowindwillowindalmost 6 years ago
Yes please,

What an interesting fantasy. Well written and almost believable. Please do carry on with the story.

AnonymousAnonymousalmost 6 years ago
Moremoremoremoremoremore NEED MORE!!!

Plz

melinda4cdmelinda4cdabout 6 years ago
more

"Oh don't worry about it. It's all part of being a woman. There's far worse to come, believe me babe."

Sounds ominous, and oh so very promising!!!!

janetjoneslovesyoujanetjoneslovesyouabout 6 years agoAuthor
More, anyone?

Hi - anyone interested in the next part of this story? Let me know with a comment! x

AnonymousAnonymousabout 6 years ago
my fantasy

loving this story , can't wait for more . damn i wish my transition could be this fast, oh well i can dream. loving this loads. thank you.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Transformation of Kerry Young man takes drug that turns him into a woman.in Transgender & Crossdressers
Chimera Medical treatment turns a man into a woman.in Transgender & Crossdressers
Tricked with a Pill Man tricked into taking a pill that turns him into a woman.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Transformation Ch. 01 Transformed into a female, Sara has to adapt to her new life.in Sci-Fi & Fantasy
More Stories