Peter's Wearing Panties and Tights

Story Info
What will happen if his boss finds out?!
3.9k words
4.14
25.7k
14
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
CarrieQ
CarrieQ
159 Followers

Peter was 31 when his troubles began. He lived with his long-term girlfriend in one of those anonymous towns between London and Birmingham that hardly anyone knows about; the kind of place most trains speed through without stopping.

For the few who catch the trains that do stop, his face was familiar, for he worked as a ticket clerk at the station. It was a job he hated, though he stuck at it because it just about paid the mortgage, a matter of some importance since Debbie, his partner of three years, had recently been fired.

Chances are you'd not have noticed Peter in a crowd; he wasn't the type who stands out. His puny frame was topped with mousy hair and he wore the kind of thick-framed spectacles that make a dull face even less remarkable. Drab was the word he brought to mind, especially when wearing his grey uniform.

Sat behind his kiosk, issuing tickets and timetables while counting small change, those few commuters who could be bothered to notice him at all must have figured him a boring nerd...

But they were wrong!

Peter had a fetish for silk panties and patterned tights, and wore them to work whenever he could get away with it, which meant more or less every shift. His only obstacle was Debbie, who knew absolutely nothing of his obsession. He thought it best to keep her in the dark, since Debbie was the kind of woman who can be called conservative, in every sense of the word...

Or so thought Peter!

He kept his extensive lingerie collection in an old chest in the spare bedroom, cunningly camouflaged under a copious pile of trainspotting magazines. Debbie hated everything to do with trains, so he knew she'd never search there; but just to be safe, he kept it padlocked.

Every workday morning, he'd hurry out of the bathroom into the spare room and swap his drab Y-fronts and navy blue cotton socks for a pair of frilly silk panties and patterned tights. He owned examples of every brand you've ever heard of, collected at first by mail order, but as he became bolder, he began journeying to nearby towns on his days off and buying them over the counter.

On the fateful morning I'm about to describe, Peter selected a pair of black, floral opaque fashion tights, which he wore over pink lace panties. Walking to the station, he felt divine. He adored the feel of nylon encasing his legs, and the mildly uncomfortable nip the panties gave his balls in the middle of every stride!

He was looking forward to another day of ad hoc arousal as women passengers pushed their racks right under his nose in an effort to be heard. Peter had perfected the art of feigning deafness, then ogling them at his leisure while appearing to be otherwise occupied, while simultaneously sliding a butt cheek off the edge of his stool in such a way that the panties pulled hard against his bulging cock, while the tights tickled the tip of his tender cherry!

Sometimes, the excitement overwhelmed him and he came in his panties! But he'd been at it so long, he could carry on as if nothing had happened, counting change while covertly leering at a pretty bosom and filling his panties with spurt after spurt of hot cum, with nobody any the wiser!

But on the morning in question, he arrived at the station to a nasty surprise...

Mr Taylor, the Area Manager, was there to meet him!

"Ah, Peter! Good to see you're punctual as always! Come into the office for a moment!"

Reluctantly, Peter followed him into the back office. He didn't like Mr Taylor much, because whenever a bigwig like him condescended to meet a minion, it meant bad news; either a poor performance review, or some irregularity in his paperwork. Mr Taylor wasn't known for wasting his valuable time heaping praise on the hoi polloi!

Stepping into the back office, he was surprised to meet an absolute beast of a man; an alarmingly tall and bulky brute with tanned leather skin and tattoos over every inch of skin that wasn't covered by a white nurse's tunic.

"This is Clarence," Mr Taylor explained condescendingly. "He's here to give you your tetanus shot!"

"W-what?!" gulped Peter.

"You might remember I sent out a memo about this months ago, reminding everyone that it's compulsory, and that I'd arrange a shot for anyone who hadn't filed a vaccination certificate by the end of last week? And as you can see, I'm as good as my word!"

"B-but..."

"No buts, Peter! It's important that everyone has their shot!"

Clarence removed a syringe with a frighteningly fat needle from a sterile wrapper and glared at Peter with wild, manic eyes. "Drop your trousers and bend over!" he commanded sternly.

"N-no! I c-can't!" Peter protested...

But Mr Taylor was fast losing patience!

"Come on now!" he insisted irritably. "There's no need to be shy, we're all men here! It's just a little prick on your arse, that's all; it'll be over in a jiffy. Now take down your trousers!"

"No!" Peter was adamant he wasn't having his preference in underwear examined at close range by the Area Manager, and certainly not in the presence of a boorish oaf like Clarence. But Mr Taylor took another view of the impasse...

"I understand!" he exclaimed in a deeply patronising tone, giving Clarence a knowing wink, "It's yet another case of Trypanophobia; the morbid fear of needles! I thought that's why a normally conscientious fellow like you hadn't complied with my memo. But don't worry, Peter; Clarence here is an expert at dealing with chickens like you, that's why I hired him!"

With a sickening smile, the giant nurse stepped forward and grabbed Peter round the waist. He struggled furiously, but was no match for the far bigger man, who effortlessly bent him over the desk and began yanking down his trousers until...

"WHAT THE FUCK?!"

Clarence abruptly let him go, and Peter felt his face turn crimson while he saw the two men had suddenly turned pale. Each was gawking open mouthed at Peter's buttocks, clad as they were in silk panties and floral patterned tights!

It took Mr Taylor several minutes to recover some of his former composure, and when he did, he was far from amused...

"You'd best clear your locker!" he told Peter.

"B-but why? How can my choice of underwear affect my ability to do my job? Nobody can see it, unless of course,"... (and here he gave Clarence a boldly malevolent glare) "some bastard pulls down my trousers! But how often is that going to happen, eh?"

"That's not the point, and you know it!" Mr Taylor intoned with a weary sigh. "Railways run on rules, and the rulebook states unambiguously that 'the wearing of inappropriate undergarments for the purposes of sexual gratification shall result in instant dismissal.'"

"But I'm not wearing them for sexual gratification!" Peter protested. He suddenly felt terribly sick, cos instant dismissal meant he'd be paid only the hours owed, which wouldn't cover the mortgage! Plus he'd get no reference, so finding another job would be awfully difficult...

He and Debbie would be out on the street!

"If you're not wearing them for pleasure," Clarence enquired slyly, "Then how come they're soaked in cum?"

Peter glanced at his crotch and saw a large damp patch spreading through the panties and tights from the tip of his cherry. He reddened even further, sending his hue into the infrared spectrum. Yet still, he felt determined to fight his corner!

"Th-that's the result of shock!" he insisted. "People get erections when they're hanged; it doesn't prove anything!"

"You're clutching at straws, Peter!" Mr Taylor protested, "Please don't embarrass yourself further by forcing me to have you escorted off the premises!"

But Peter wasn't finished; in fact, he was only getting started...

"As you're so keen on the rulebook," he continued, "You'll know the company is bound to respect every employee's definition of their own gender? Well, I've decided I'm a woman, so if you sack me I'll sue the company for discrimination!"

"Oh, Peter, Peter!" Mr Taylor's head sank into his hands, and he began to look terribly depressed. A long pause ensued before he spoke again, and when he did, he sounded resigned yet resolute...

"Very well!" he conceded, "If you've decided you're a woman, I cannot dismiss you for wearing women's underwear! But I CAN reasonably expect that, starting tomorrow, you'll arrive at work dressed as a woman! That you'll act like a woman and obey all the rules applying to female attire, and that you'll provide timely evidence that you've done all those things the law requires of you in order to become a woman! Do I make myself clear?"

"Y-yes sir!" Peter gulped. He was then sent home for the day, and Mr Taylor exchanged a cynical smile with Clarence.

"Don't you worry sir, you'll not see him again!" the giant nurse predicted.

"I only hope you're right!" prayed Mr Taylor...

But he was not!

**********

Walking home, Mr Taylor's last words rang through Peter's head like a klaxon. His elation at having saved his job quickly dissipated, as he realized that if he didn't arrive at work tomorrow in full compliance with the company's rules regarding female employees' attire, then he'd be no better off than if the instant dismissal had gone ahead!

His first problem was how to tell Debbie...

Reaching home a little before noon, he noticed the bedroom curtains were still drawn, which was no longer unusual. Debbie seemed to have given up looking for a job recently. Most nights, she sat up into the early hours drinking cheap wine while watching crap on TV. She'd become demoralised and thoroughly bad tempered, so this wasn't going to be an easy encounter!

Boldly entering the bedroom, he ignored her protests and flung open the curtains...

"Wake up!" he yelled, "I have something important to tell you!"

"What time is it?" she asked, sounding slightly confused. "And why aren't you at work?"

"It's almost lunchtime, and I'm back from work because I've kind of been fired!"

"WHAT?!"

She sat bolt upright in bed, and after several stutters, Peter managed to blurt out the whole story. To begin with she looked shocked, but her shock soon turned to anger, so that by the time he'd finished, no psychic powers were necessary to guess how much she loathed him...

It was written all over her face!

"Well?" he asked finally.

"Well what?!"

"Well, what do you think we should do?"

"I'm not going to do anything," she seethed, "but you will have to go to work tomorrow dressed as a woman! I'll help you, but only cos I don't want to lose my half of the house! From now on, me and you are finished, and you can sleep in the spare room with all your precious panties and tights! Understand?"

"Y-yes!" he gulped.

Debbie was one of those women who wear a scowl so perfectly, there's never a doubt whether she's in a bad mood, and she left the house with a face like thunder, returning some hours later laden down with shopping bags, but looking none the happier.

She handed Peter a tube of hair removing cream, and ordered him to go in the bathroom and remove all his body hair. While he was busy doing that, she emptied all his drawers, bagging his clean clothes for a charity shop while putting his dirty laundry in the dustbin.

When he finally emerged from the bathroom, Peter didn't have a single hair anywhere, except on his head. Debbie helped him into a 34B plain white cotton bra, which she padded out with some of her own bra fillers.

Then she handed him a pair of natural tan tights...

The look of disappointment on Peter's face was quite something to behold, but Debbie was running short of empathy just then!

"What's the matter, not fancy enough to satisfy your sordid tastes? Well, tough shit! The rulebook says women's tights and stockings must be plain and skin-coloured!"

Peter made no reply, but put them on so expertly that Debbie seethed even more! It made her realize he'd been doing this for years, and the fact she'd not known made her more than livid! Still, a revenge strategy was germinating in her mind! She handed him a panty girdle...

"What's this for?" he asked, sounding bewildered.

"To stop your tights slipping and make sure you don't have a bulge in the wrong place," she explained. "Not that your tiny cock would stick out much!"

"I don't have a tiny cock!" he retorted, sounding seriously miffed.

"Oh, yes you do!" she scowled. "As a matter of fact, you've got the smallest cock I've ever seen! And you don't know how to use it either, though today I've found out why! Well let me tell you, things are gonna change in this house!"

Peter knew that when Debbie got in this kind of mood, there was no point arguing with her, so he put on the panty girdle in silence, then the plain white blouse and grey skirt suit she'd bought, and lastly a pair of black court shoes.

"Well, old Taylor can't argue with that!" she declared, looking grimly satisfied with her own handiwork. "The skirt's no more than an inch above the knee, and the shoes are black with two-inch heels, just like the rulebook stipulates. Now sit by the dresser and we'll sort out your hair and make-up..."

Debbie fetched herself a large glass of wine and began teaching Peter about make-up. "The rulebook says women must wear lipstick and mascara, but cannot wear eyeshadow or blusher," she explained. "I've also got you some eyeliner and foundation cream, which will hopefully hide your stubble, and an eyebrow pencil. Now pay attention, cos you're gonna have to do this yourself at work, and if you fuck up, I'll lose my house!"

Peter spent the rest of the afternoon and most of the evening learning how to apply make-up, while Debbie shaped his eyebrows and fitted him with one of her old wigs, a blonde bob surviving from her student days. Time seemed to fly, until Peter noticed it was fast approaching midnight, and realized he needed to get to bed...

Tomorrow was going to be a huge day!

Without thinking, he walked into the bedroom, but Debbie wasted no time reminding him of the new arrangement...

"Oh no you don't, Peter!"

"Not even just this once?" he pleaded morosely.

"No! I've been dissatisfied with your creepy antics for quite some time, but this is the final straw! You're a lousy lover whose tiny cock cums so quick I hardly know whether it's been inside me, and you have absolutely no idea of foreplay. I'll stay with you for now to protect my investment, but you're not to go in my room ever again, and you're never to touch me, understand?"

"Okay, okay!"

Reluctantly, Peter retired to the spare room, where he found a negligee had been placed atop the narrow spare bed. He undressed and put it on, finding the touch of silk on his freshly epilated skin strangely tantalizing!

Finding it hard to sleep with so much on his mind, he soon began playing with himself, swishing the hem of the negligee every which way against his growing phallus as creamy pre-cum dribbled copiously from his quivering cherry.

Remembering Debbie's cruel taunt, he measured his erection with thumb and forefinger, satisfying himself it was almost four inches long...

"You're not small!" he repeated quietly to himself, over and over, as spasms shot through his legs, sending spurts of hot cum onto the bedsheets!

**********

Peter rose before dawn, feeling surprisingly sprightly considering he'd hardly slept. After the briefest of breakfasts, he carefully dressed himself just as Debbie had instructed, spending far longer than was strictly necessary fitting his wig and applying his make-up.

In the hallway, he found Debbie's old handbag and purse had been left out for him, so he put his make-up inside the bag, transferred the contents of his wallet into the purse, and tentatively walked towards the front door.

There, the biggest of butterflies made him weak-kneed and wobbly! His fingers trembled on the doorknob, and he seriously considered returning to his room, changing into his regular clothes and going to the JobCentre instead! And he might have done it, except he remembered Debbie had disposed of all his male clothing! He had nothing to wear except the women's clothes she'd bought him...

As she'd said, she was going to protect her investment!

Still, the fact there was no going back gave Peter a boost of courage! Boldly, he opened the front door and stepped into a familiar world in an unfamiliar role.

During his first, tentative steps, he was shaking with fear. He tilted his head every which way, just to avoid eye contact with the increasing crowd, which grew exponentially as the town centre loomed closer.

But soon he realized no one was giving him a second glance. The morning rush hour is a time of preoccupation, and a harassed commuter has little time to waste on analysis of his fellow travellers' dress sense.

Peter soon relaxed and began to enjoy his walk to work, perhaps for the first time ever! He enjoyed the morning sun on his back, the click of his heels on the pavements and the gentle breeze teasing his smooth, nylon-clad legs!

Arriving at the station, he felt confident in ways he'd never imagined possible. He strolled straight into the staff room and opened his locker, ready to prepare for his day's labour...

But Dave the Station Master hadn't recognized him!

"Excuse me, miss; but who are you and what are you doing here?" he demanded.

"Can't you see who I am?" he retorted teasingly.

"P-P-PETER?! No! What's happened to you?!"

"Didn't Mr Taylor tell you I'd be presenting as a woman from now on?"

"N-no he did not! He said we'd never see you again, but in the unlikely event... Oh, God! Wait here!"

So saying, Dave fled the room in a terrible flutter!

Mr Taylor was in his office 50 miles away, admiring some photos of the newly restored Flying Scotsman. He'd always thought fondly of the age of steam, a golden era when queers were jailed and women were only allowed to work on the railways during times of war! He was truly dismayed when Dave shattered his peace to tell him that Peter had turned up, dressed as a woman!

"But is he dressed according to the rulebook?" he demanded.

"It looks like he is, sir!"

"You're sure his skirt's not too short? His heels aren't too high? He's not wearing a colourful blouse or too much make-up?"

"No, sir! He seems to be fully in compliance!"

Mr Taylor sighed deeply, wondering what the world was coming to!

"Well in that case, you'd better tell him to start work!" he grumbled bitterly. "But keep an eye on him, Dave! He's sure to slip up, and once he does, he'll be out the door!"

"Yes, sir!"

Peter worked his shift without incident, giving his employers no grounds for complaint...

For such a landmark day it had been remarkably uneventful, but still Peter was very tired when he knocked off, and couldn't wait to get home.

Arriving in his road, he was surprised to see Debbie still hadn't drawn her curtains! Even stranger, when he opened the front door, he was assailed by the pungent smell of cigarette smoke.

Ascending the stairs, he heard raucous laughter coming from Debbie's room, then her voice beckoned him to enter. He tentatively opened the door...

And found her lying in bed with Kyle Jones!

He could hardly believe his eyes! Kyle was the worst of the bullies who'd made his life a living hell at high school and here he was, locked in a passionate embrace with the woman he'd shared the last three years of his life with!

He knew Debbie had often shown bad judgement in her choice of boyfriends, but this guy took the biscuit! An unemployed, illiterate thug who spent half his time in prison!

"Well, fuck me if it ain't true!" Kyle exclaimed gruffly, leering luridly at Peter, "So you are a fucking fruit! I thought maybe Debs was winding me up, but seeing is believing! Take a seat," he added, pointing to an armchair strewn with their hastily discarded underwear.

"No thanks!" Peter replied, turning to go.

CarrieQ
CarrieQ
159 Followers
12