Modern Holes -

"It's fine, you look cute!"

Francis' Mom looked at her son dressed in his rented tux. Black coat and pants, white shirt, cummerbund, and a matching black bow tie, he even had his hair done up in a tight little bun at the back of his head. She could say that he cleaned up well. Her handsome smart little man.

Francis however was fidgeting uncomfortably. This was basically the first time he was dressing up so formally. Nothing seemed to fit just right, too tight if he had to put it into words. He was feeling quite constrained.

Tugging at his neck. "I don't know, this seems a bit much?" The starched white collar was stiff and rubbing against his skin every time he moved his head.

"Come on now, it's prom!" Debra fussed over Francis' clothing. "You really only get to do this the one time. I remember how dashing your father looked in his tuxedo. It was quite the magical time." Her own eyes glossed over in memory back many years to her own time standing in a gym under soft lighting.

"Yeah yeah." Francis really couldn't stop itching and tugging on the suit. "I get it, I'll do my best. Not step on too many toes.

Brought back to the present slightly more forcefully than she would have liked, Debra gave his shoulders one last final dusting. "Yes you will. So, what's your plan for the evening?"

"Drive over, greet her parents, promise to get her home safe, drive to school, dance, come home safe." He recited the outline of his plan for the evening for perhaps the tenth time. Already itching and antsy, he rocked his feet side to side.

"Forgot one thing." She put her hands on Francis' shoulders. Staring into his face and then into his eyes. When they locked onto each other. "Have fun. That's the important part, have fun."

"I will mom." Francis let his face break into a smile.

"Good!" Debra pulled her son into a hug. "Good. Now get out there."

Returning the hug for a beat, Francis picked up his winter coat and slung his arms through the sleeves. It's thick fabric giving the teenager a bit of bulk against the winter chill.

He stepped towards the door and put a hand on the knob but stopped. "Keys?"

"Right right right right." Debra snapped her fingers a couple times and walked back into her room where her purse currently was. She came back quickly with the car keys but paused before handing them over. "Madeline doesn't touch these, right?"

"Absolutely not."

"Good. Have fun, get home safe."

Keys in hand and with a final wave of thanks, Francis stepped out into the deep snow. The light of day was almost done, he had to go pick up Maddie, and then it was time for a party.

-------------

"It's fine, you look beautiful!"

Maddie's mom was hovering around her daughter like a humming bird drinking from a flower. "Tell her she looks beautiful."

"You look beautiful." Came the dutiful response from Mr. Callahan as he sat nearby. His own role in the preparations having long been relegated to short sentences of encouragement. That and his other bit of prepared comedy with a foam dart launcher resting on the nearby table, tradition would not be denied.

"See? He says you're beautiful." Mrs. Callahan fluffed up a particular piece of shawl that was draped over Maddie's shoulders.

Maddie herself was also feeling a bit stuffed right then. Stuffed into a dress, stuffed into her role, and generally stuffed with a snack from earlier to calm her nerves. Snap peas, not candy.

She was wearing a very shiny sequined one piece dress. It's dark green base colour matched well against her pale skin and red hair. It's floor length skirt covered up some high heels that were adding no less than three inches to her height and were already attempting to murder her ankles.

The matching shawl and clutch style purse rounded everything out well. The shawl covered her bare shoulders and was providing a small amount of warmth from the rest of her more exposed ensemble. The clutch had it's own sequins and glittered just as much as Maddie's torso did in the light of her kitchen.

"Thanks Mom, thanks Dad." Maddie fidgeted in place, her face somewhat strained from the effort to squeeze herself into the dress. Her legs moving back and forth, filled with a weird kind of energy. Not nervous energy though, more like excitement.

-------------

Francis' large coat bunched up around his neck when he sat down in his mothers car. The keys still in hand made their way under the wheel and inserted into the ignition.

Giving those keys a twist caused the vehicle to start up with a mild roar. The kind of roar that only a cheap reliable commuter car that was in need of some maintenance could provide.

Francis adjusted the mirrors for his increased height over his mother, put the car into reverse, then pulled back into the street and turned to face Maddie's home. Already he could see the light of her door as it was illuminated in the fading light of day. A target to approach cautiously.

The car now in drive, he pressed down on the accelerator and crunched through the snow at a sedate pace. There was plenty of time to go before the prom started, and he wanted to give himself a minute to settle his sensitive nerves.

Deep breaths now. He pulled the car all the way up the Callahan's driveway as he could. This was the moment of truth.

Stepping back out into the snow, Francis left the car running to build up a bit more heat.

Snow crunched under foot as he approached their front door. He almost slipped on hidden ice with the first step, catching himself with a miniature heart attack. That accident avoided, he regained his balance with the next step and all too soon he stood at the door.

No going back now, Francis rang the doorbell.

-------------

"That must be him~!" Mrs. Callahan announced with a little sing song lilt to her voice as she rushed towards the door.

Maddie's breath hitched in her throat as every part of her stiffened up. What if he hated how she looked? What if she fell down on the ice and hurt herself? What if someone hit their car? What if? What if? What if?

There was a heavy comforting hand that fell upon Maddie's lower back. Her Father had stood up next to her. "It's going to be fine." His voice low and soothing. "He likes you, you like him, tonight's going to be easy."

"Francis! Don't you look handsome! Come in, come in!" Mrs. Callahan ushered the boy inside.

"Thank you Mrs. Callahan, it's nice to see..." Francis' tongue got stuck in his throat as he laid eyes on Maddie.

She was lovely, perfect, beautiful, cute, sexy, all those things rolled up into one. Her dress hugged her figure like he had never seen before. All those hours running had done wonders for the girl and tonight was the night to show it all off.

He was gorgeous, strong, tall, sexy, and right here for her. The coat accentuated his shoulders and what he was doing with his hair really showed off his face. All those hours in the gym had finally put some meat on those bones and tonight she was going to revel in them.

Mrs. Callahan giggled and tugged at Francis' coat. "Take this off, I want a picture."

"Ah! Yes." Broken out of his stupor, Francis shucked off the coat and hung it up.

"Go join him." Mr. Callahan gave his daughter the tiniest of pushes.

Maddie and Mrs. Callahan swapped places. The mother taking up her daughters former spot and wrapping her arms around her husband, the daughter walking up next to her boyfriend and stood close, but not too close.

So Francis and Maddie stood next to each other. Green dress, black tux, and as much teenage awkwardness as their two bodies could handle.

"Oh really get in there!" Mrs. Callahan fluttered her hand towards the two of them. "I'll go get my phone."

The two teens shuffled a little bit closer together. Drawing a frown from Mr. Callahan when Francis put his arm around Maddie's waist, but the goal was accomplished.

"Say cheese!" Mrs. Callahan held the phone with it's camera up to her face. Catching just the perfect moment when the dart smacked Francis in the face.

The photo captured Maddie's surprise and sudden loss of balance paired with Francis' whole body flinch from the little green and blue foam projectile as it was a blurry blob bouncing off to the right. Her shocked face was paired with his squinted eyes and pursed lips.

"Let that be a warning to you." Mr. Callahan gave a dark chuckle. "More where that came from if you don't get her home safely."

"Dad!" Maddie stomped her feet and almost lost her balance again. Shawl slipping off her shoulder and green sequins glinting in the light.

"It's fine Maddie." Francis rubbed the impact point with his finger. "It's fine." He stood up straight once again and wrapped his arm around his girlfriend.

This time, the photo was more normal. Francis stood slightly behind and Maddie slightly in front as the two of them posed for Mrs. Callahan. Front to back and back to front, the two held the pose and each other as the two parents watched and photographed to their hearts content.

They only got away because Maddie complained about getting there on time. Francis in his coat, and Maddie in hers. Hers being a regular black puffy coat because getting a matching green coat for this one event was crazy talk.

When the front door shut, the two of them could finally breath a sigh of relief.

"This was a bad idea." Francis said and offered Maddie his hand for the few steps down.

"Nah, it was a great idea." Maddie took his hand, and together, they walked to Francis' mother's car that would take them to the prom.

*************

"This is a bad idea!" Francis hissed through the mirror hole, standing in his room an hour earlier.

"It's a great idea! I don't know what you're worried about." Maddie replied with a casual nonchalance as she stood in her own room.

They were both getting dressed for the prom that evening. Each in their own way.

Francis was having a hard time doing up the bow tie. He had foolishly decided to be traditional about it and was not using a clip on. The rabbit chasing through the hole was going the wrong way and it kept ending up crooked.

Maddie was just relaxing in her underwear for the moment. Having already tried on the dress a few times before and finding it very confining. Besides, she needed free reign to enact her 'idea' that Francis was stubbornly insisting was 'bad'.

"It'll make the evening fly by." She tried to entice him. "And it'll be our own little secret. I can bet no one else will be doing it!"

Giving up for a moment, Francis let the two ends of the bow tie dangle around his neck. "Maddie. Of course no one else will be 'doing it' because no one else CAN 'do it'." He considered moving to the bathroom because it had a larger mirror to work with.

"Oh come on!" Maddie tried the most childish of huffs she could muster. "I want to, isn't that enough?"

"Not really." Another attempt at the knot.

"I'll suck your dick?"

Halfway through the knotting, another failure, Francis paused to sigh. "That's technically a step down from your proposal."

"I'll suck your dick so you get hard enough for me to keep you inside me?"

Rubbing the spot between his eyes. "You're really set on this huh?"

"You have no idea." Maddie could imagine it now. His hot hard dick filling her vagina and with every step it rubbing against her. That thick cock just keeping her full and stimulated the entire evening. Damn right she was set on doing this.

"OK fine, twist my arm why don't ya?" Francis reached down to his backpack and fished about for the cock ring hole.

"Yessss!" She picked up her own end, already sitting on top of her desk in anticipation of his acquiescence.

Unzipping the dress pants of the rented tuxedo, Francis pulled out his dick and slotted the brightly lit hole over top of his soft member. On the other end, Maddie watched as the little pink worm peaked it's body out of the ground.

Like an early bird for said worm, she licked her lips. Time to manifest destiny, Seize the day, and get that cock.

It was small, tiny, easily swallow-able, travel sized, even cute if Maddie had any strong opinions on it's appearance. Right away she placed it fully into her mouth and started sucking like it was a pacifier. Fun sized though it may be for now, it would soon blossom into it's full raging hard on glory.

The soft member She was sucking on was already growing every so slightly. She lathered most of her attention on the tip while it was still so malleable. Her tongue licking up and down as, with every heart beat, his cock started to lengthen and harden in her mouth.

There was always a sense of power that Maddie felt whenever she did this. The feeling of Francis' dick getting harder and thicker as she sucked on it was not going to stop being a secret joy of hers. Every time she did this it reminded her that he was getting aroused and hard for her. It wasn't because of anyone else, just her.

Francis just knew that this was going to be a terrible idea, but had to admit it had it's perks just right at that moment. Maddie's tongue on his swiftly growing member was always a delight. He wanted to prolong this feeling but at the same time also wanted to revel in it. Splitting the difference here meant making another attempt at the bow tie, but getting distracted easily.

A warm mouth, a wet tongue, and her undivided attention was bringing him to full mast. All too soon his cock started to feel the cool breeze of air as he came to attention and no longer truly fit fully inside of her. Thankfully, she stayed attached at the top and brought up one of her hands to stroke him with soft fingers. It was practically calculated to get him as hard as possible.

So hard that Francis had to stop everything he was doing and lean over onto his desk. He had reached peak stiffness and she was still going. That sloppy wet feeling of suction around his tip, paired with the swift motions of her hand, were driving him to distraction. If she kept this up for much longer then her plans would be impossible without at least a fifteen minute break.

Maddie let off with a little pop of her lips. "Alright there, I think you're ready." Licking up any errant strings of saliva and swallowing the tiny bits of precum that he had produced for her.

With a tiny shudder, Francis set about getting himself ready for Maddie's 'plan' for the evening. A condom was procured from the surprisingly empty bulk pack. He would have to get more soon. His full thick cock was extracted from the cock ring hole. It's slick surface sliding through the silicone ring with ease thanks to the lubrication that she had provided.

Condom on, cock placed back through it's ring. "Do with me what you will woman." He surrendered to her diabolical machinations.

Smiling the smile of complete victory, Maddie was giddy. "That I shall. Get ready for this."

She sat on the edge of her bed, next to her lain out dress, and pulled her panties to the side. Francis' condom covered cock in all of it's alliterative glory was pulsing in her hand. She placed it at her entrance and rubbed the head against her. That fat head pushing against her puffy folds, spreading her a tiny amount just with it's mere presence.

Maddie hummed contentedly as she prodded herself with his dick. Sucking on him to get him hard had already done a little to get her wet. This right now was just finishing the job and helping to spread her juices all over his tip. She used him like a paintbrush to lather on the clear lacquer of her wetness.

Wet and ready, she pressed Francis in. His hard cock spreading her walls with it's thick head. The spreading continued and continued as his hot length made it's way inside. With every inch she felt more and more of the delicious fullness that happened every time she got to enjoy him.

Maddie shut her eyes and fell back onto the bed for a minute as she just continued to work him inside of her. Tiny in and out movements as she slowly worked him deeper and deeper inside. The wetness from her walls spreading it's thin lubrication all over it's favourite invader of the evening.

With a final push, she slotted Francis' cock fully inside of her. That last movement punctuated with a delightful thrill as her own fingers brushed against her clit. The tiny pleasurable spasm it's own little orgasm and a sign of what was to come that evening.

Francis was lost in his own little world as well. He knew that Maddie's vagina was the best one he had ever felt. Every time she had used his dick was just as good as the last time. However, this evening there must have been something a little special as she felt just that bit better than ever before.

Maddie just luxuriated in the feeling of being absolutely full of cock for a minute. Her vagina was stretched to it's limit. She could feel the bump he made, tiny as it was, on her stomach, as it filled her. The way it rolled and moved inside of her as she brought her legs up and down were especially delightful.

But the evening would wait for no woman. So she allowed herself one final calming breath before resetting her panties to their central position. Trapping the other end of the cock ring inside and not allowing it to fall out. There was a weird looking imprint where the hole was, but no one else was going to look at it that night so it would be fine.

Sitting up was a new experience. Francis' hard cock added a little bit of stiffness to her movements that sent a thrill up her spine. Getting to her feet after that didn't have anything to compare with. Her legs coming together caused a wonderful pressure on the dick inside of her. But it was the first few steps that almost set her off.

Francis himself was having a hard time deciding if Maddie was a genius or a moron. The sensations coming from his encased dick were wonderful. The pleasure was unique in it's feeling. Normally Maddie would be using him like a dildo with certain in and out motions. This snug rubbing was less, but it was constant. If she kept this up for too long, he might become numb, or he might lose himself early.

The only thing he could do was focus on the task ahead of him. The bow tie knot would get tied eventually.

With every step Francis' dick rubbed against her walls. Thick as he was, hard as he was, it was absolutely fantastic for Maddie. His warmth radiated into her and she could feel his heart beat with every pulse of his cock.

This distraction on Maddie's mind, she knew that tonight would be a real challenge to keep things steady. But it was a challenge she had invited on herself and a challenge that she would see through. But before she could get to that part of the evening, she had to get dressed.

The green sequins sparkled beautifully in the light as she lifted her dress up. A few months ago she would have turned her nose up at going to prom. A few months ago she would have never expected to have a date to prom. A few months ago she would have never thought of even having a boyfriend. But her she stood with all those things and more having finally happened to her.

Dress up and over Maddie's head. The open zipper providing the necessary clearance over her shoulders and bust. The integrated corset settled around her waist and on her hips. The zipper being it's own difficult thing to pick at and she was not able to get it all the way up.

Well, this is what parents were for.

"Hey Mom! Can you come zip me up?" Maddie called upstairs.

*************

The school looked different at night.

Sure Maddie and Francis had gone by in the dark before. When everything was shut down, the windows dark, and the doors closed. But this was when the school was alive and in the dark. There were a couple of windows lit up that spilled yellow light onto the snow outside. A banner was illuminated and hung over the main entrance that welcomed all the seniors to the winter ball. An attempt to add a little hint of class to the event.