[Fiction] Living with Libby

[Slenderman - Doctor]

Part One

"Don't get your knickers in a twist" ... are the words he would've said if the ball was in his park. However, on this occasion, the ball was out of his park and a hundred miles across the ocean. Or, in other words, Libby had the upper-hand. She'd caught him red-handed with her very own pink knickers around his waist.

He couldn't help it. Tom, his name, was naturally just a curious person. Always had been, always would be. It had been a beautiful summer day and, whilst his neighbours all tripped out to the local park, he was stuck indoors doing a three-page essay which was already four days overdue. His laptop was situated right by the window so he started to tan nicely as words slowly trickled from his brain to the document on screen, but his gaze was diverted to the garden next door. More specifically, the washing line in the garden next door.

Bright pink knickers with matching bras hung on the line.

They belonged to Libby, his friend-as-such at school. She was one of those kinds of friends you had but never really spoke to bar the odd 'hello' in passing. They got on well, though, and enjoyed larking about in RE together every Tuesday afternoon.

His essay soon became five days overdue because he found himself distracted for quite a while, even to the point of heading outside to sneak over the fence. His mind raced with thoughts and mad ideas, and the rational part of him was demanding the attention that he never gave. Instead, he gave way to the horny side and you can't blame him. He was only human. And male. So there he was, ducked in the shaded corner of Libby's garden cautiously looking around to check the coast.

The coast was clear. There were loads of pairs of underwear on the line, so he thought she surely wouldn't notice one going missing. And how wrong he was.

Libby was a bit of a fanatic when it came to her clothes, and had everything arranged perfectly. (By 'arranged perfectly', I, of course, mean she had everything thrown around her room but done so in a way where she knew where everything was, and how many of everything she had.) I suppose you could say she knew her wardrobe inside out, literally. Collecting in her clothes, she immediately spotted her bright pink underwear had gone walkabouts but, for several weeks, had no clue how or where they'd vanished to.

After his quick wank over her bra that day, Tom had shoved the pink set into the depths of his own wardrobe, hidden away from the world and hadn't touched them since. But one particular Tuesday he woke up with an urge to masturbate. He couldn't, though, as the bus was ten minutes away and he had to dive out of the house to make it into school on time. He could, however, divert attention away from masturbation by doing something else to fulfil his urges. As time ticked away, he rooted for Libby's pink knickers and pinged them perfectly in place around his waist.

And then RE happened.

[Slenderman - Doctor]

Part Two

"Don't get your knickers in a twist" ... are the words he would've said if the ball was in his park. However, on this occasion, the ball was out of his park and a hundred miles across the ocean. Or, in other words, Libby had the upper-hand. She'd caught him red-handed with her very own pink knickers around his waist.

The day had been going pretty well until that point. He’d received an A in his maths exam and had been made a prefect.

And then RE happened.

He took his usual seat by the window and waited for Libby to arrive. Unbeknownst to him, his black blazer had caught on the chair and had risen part-way above his waist, revealing a bright pink strip just above his trousers.

The classroom started to fill with half-asleep students and, at last, Libby entered the room and headed in Tom’s direction. He gave a slight nod of acknowledgement before continuing his quest on Angry Birds. Flinging her bag to the side of the radiator, Libby reached for her chair and then, just as she sat down, she caught a glimpse of Tom’s choice of underwear today.

He’d forgotten all about the knickers by this point, as they were rather snug around his lower regions. Picking up her jaw from the floor, she proceeded to hide her shock and got on with doodling over the face of Jesus in her RE book as normal. Ten minutes into the lesson, as Mrs Potts finally closed her mouth and handed out work for people to carry out in pairs, in silence, Libby saw her opportunity...

Tom reached up a few inches to grab a paper from the opposite desk, and Libby reached out her hand to grip at his waistline. She gave a slight tug and loosened his pants, exposing more of the bright pink knickers she’d lost a few weeks previously. Tom, meanwhile, had crashed back into his seat in an attempt to cover up but he was too late. Luckily for him, nobody had seen. Unluckily for him, Libby had.

He’d been caught red-handed, pink-knickered.

[Slenderman - Doctor]

Part Three

That was three years ago now. Libby and Tom were attending university, in their first year, and had moved on. Moved on in the sense that, after a good slap around the face, they’d talked extensively and taken it in their stride. Libby had been rather amused by the idea of Tom wearing her clothes, and so they’d started experimenting a lot more. Over the course of two years at college, their friendship strengthened and the pair began experimenting more and more. Strictly with clothes, though, every time. Libby would take great amusement in dolling him up, applying makeup and having him model on a catwalk in her room. A good amount of albums lined her documents folder on her laptop, and they both had a great laugh doing it.

Their first year at university had come to an end now, and the friends had a decision to make. A great four months of summer were waiting, and they’d paid up-front for their very own flat. Originally they’d planned to go for a house-share with their gang of friends but this didn’t last long, primarily due to logistics and the fact their friends all commuted in from afar. So they pitched in together and forked out for a two-bedroom flat. Their friends would visit occasionally, and they’d briefly pop home to see their family too, but they both moved in on the first day of summer and made a home from home.

Tom was made to cart in all her stuff – a never-ending pile of boxes sat outside the main door waiting – whilst Libby dashed in to the kitchen to find a pen. The first thing on her agenda was to create some basic rules.

“Can we at least move in first?” Tom sulked, dropping the first of many boxes at his feet.

“Watch it! Break anything and you’re dead. Now, if you don’t mind...”

“That’ll be a no then,” she heard him sigh as he headed back down the stairs.

Simply put: Libby wore the pants in this friendship, and Tom wore the thong.

Secretly, Tom loved it. He always remembered back to the day he stole her undies, and smiled. It’d been a risk worth taking, it’d paid off. Really, it could’ve gone one of two ways. In fact, he’d heard stories, similar, wherein a guy had been found out and then publicly humiliated by the girl in question. Though that turned him on, he was so glad that hadn’t happened. Libby had many friends but her friendship with Tom was the strongest, as there were no secrets at all and they felt so comfortable around one another. Oh, they argued and fell out many times too, but who doesn’t? They were the inseparable duo. You couldn’t have a Tom without a Libby, and vice versa. And they’d both heard the “you’d make a lovely couple” guffin rhymed off countless times from many people but, ultimately, they were both happy as they were and, to be honest, couldn’t be happier.

Libby laughed.

“Well that was clever,” she said, sarcastically. Tom had finished bringing in the boxes, but had inadvertently blocked the rest of the room off. As he closed the door, he found himself surrounded by boxes and any attempt at jumping them would’ve probably led to an embarrassing fall.

She laughed again and turned back to her sheet of A4, furiously scribbling down ideas. He, meanwhile, had to play Tetris with himself until he made a route through to the living room.

“Welcome aboard,” she said, dropping her pen. “Welcome aboard the good ship, SS Libby – SS stands for Seriously Sexy, obviously.”

“Obviously,” Tom retorted, shaking his head and cracking a smile.

“Summer starts here and now, in our new house — “

“Ship!”

“—in our new ship, thanks Tom. I’m the captain and you’re my sailor,” she continued, pausing for a moment before continuing. “Or sissy, or schoolgirl, or whatever I see fit. And, as all good ships have, there are a few rules all shipmates must adhere to at all times, unless the captain says so.”

“Aye aye,” said Tom, slapping his thigh and shutting one eye.
Libby looked unimpressed.

“Well you can’t say I don’t put the effort in!”

“Hmm. So, rule one. Rule one is that shipmate Thomas must only wear underwear when aboard the ship. Got that?”

“Aye,” came the reply, as Tom began undressing. He knew not to disobey, and was already fearing what Libby’s version of walking the plank would entail.

“And the rest?”

“S’all I got so far,” she chuckled.

“You serious?”

“Seriously sexy!”

And, with that, she winked, and he threw his clothes to the other side of the settee.

“Just be grateful I’m not keeping you naked, boy.”

“You wouldn’t?”

“Challenging me?”

“You’d have to let me have some cover!”

“Yeah, suppose,” she said, throwing an eyepatch his way. “There you go, start now. Rule one – Tom must be naked at all times, but may use an eyepatch to cover his cock should he wish.”

Without any hesitation, he obeyed Libby once more, and attached the black patch around his waist as today’s purple g-string fell to his ankles.

“Good boy. Very good boy.”

[Saphir]

Hey
I like your writing stile It's pretty good in my opinion.

Actually made me read it so far even though the content (cfnm (?) cross-dressing) is really not my favorite... that's a personal thing tho

I'll check this out again for progress when I've got some time next time, would be great to read more

Love

[Maleslave21]

Amazing story wish I was Tom lol please continue

[anonimousbob]

Loving it so far :-)

[italia13calcio]

Really good! I like it, especially how it is written with that little bit of humor in it!

[tarheel boy]

You should really continue this, it's good.

[footmuncher]

This is a really great start, you have clearly taken your time and it shows. I have no doubt this will turn out to be very intersting!

[Crossdress_Bitch]

This story reeeeally needs to continue. Wonderfully written and right up my street!

[wedgied]

Great start. I can't wait for future episodes!