My Diaper Valentine Pt. 01

*Author notes* Quick warning to any readers, this story is focused around Futanari and diaper fetish and elements of Scat/Piss/Enema play. I've read hundreds of stories on Literotica over the years but none of them have hit everything at once for me. I'm hoping this can be that story for others with tastes similar to mine. The story dragged on a lot more than I thought and there is still lots more for me to write. I decided to close it out and have this be a chapter 1. This is my second story ever, and as always, I read and appreciate all feedback.

No clue if they will ever read this personally, but big shoutout to fellow Literotica author Grimbous for being an inspiration.

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The 22 year old femboy stood at the top of the tower, nervously looking down the length of the water slide. The tower was tall. In fact, it was so tall that he could feel it gently swaying with the breeze. He glanced behind him to see how badly he was holding up the line and, curiously, there was no one behind him. Not even a lifeguard. "Whatever, I've been up here long enough, lets do this!" he thought, psyching himself up as he stepped to the edge of the slide. He sat down and felt the warm water wash over his legs and crotch. He took a deep breath and propelled himself down over the edge. He screamed as he rocketed down the slide and finally splashed into the pool at the bottom.

The instant he hit the pool of water, Ash bolted upright in his bed, "Ugh, fuck man, a dream? Really? I'm fucking soaked!" he cursed. Throwing off his his covers he looked down at his overfilled, pink, goodnite pull-up. "This is what I fucking get for using all my diapers on my vacation days."

Taking half a week off work into a weekend has its perks; like, spending the whole time in diapers, eating pizza and drinking beer. It also has its cons; like, using all your diapers and getting your bladder used to going whenever you want.

He checked his phone and groaned; 10 minutes before his alarm for work. Rolling out of bed, he pulled his wet sheets and covers off and took them to the washer. He was fortunate enough to have a washer and dryer in his small studio apartment, but working at a local Walgreens didn't leave him room for many luxuries, like expensive diapers. He had been able to buy some with his Christmas bonus, but now in February, his supply was gone.

With the sheets in the washer, he opened up his box of tide pods and; empty. "Uuuuggghhh. Could this morning get any fucking worse?" he groaned, "I guess im doing laundry after work." He tore the waistband of his pull-up and rolled it up, careful to not drip pee everywhere, and dropped it in the trash on his way to the bathroom. Turning on the shower, he stared at himself in the mirror while he brushed his hair and waited for the water to warm up.

He was pretty much what you would call 'peak femboy performance'. About 5'4" tall, with petite features and fair skin, he was very pale thanks to lots of time indoors. His natural blonde hair was long and thick, usually pulled into a high ponytail. He had bright green eyes and naturally long eyelashes that his old female classmates had told him they would kill for. Below those long lashes, he kept his whole body hairless, including his small cock and balls.

His penis was uncut and just barely over four inches hard; he felt it was the biggest, or perhaps smallest, reason he was still a virgin. He was thin, around 140 pounds, and in shape from lots of cardio. Spending time on the stair stepper and stationary bike at his apartment gym every day had given him a perky bubble butt and toned legs that constantly got him looks on his walk to work.

His feminine appearance and petite frame didn't provide him much confidence, romantically, even though he had accepted it; he was straight. And despite living in a progressive and accepting city, he hadn't found a girl interested in a crossdressing, diaper-wearing femboy.

He had a crush on a coworker but she had already had a boyfriend. Being a homebody-gamer type, he didn't have too much of a social life. With the coworker Ash was crushing on unavailable, he had pretty much checked out of dating. Yeah he had a tinder account but it wasn't worth the trouble; he was content to explore his kinks alone.

With the shower finally hot, he hopped in to get clean and finish his morning routine. He brushed his hair once he got out of the shower and started to get dressed, pausing when he grabbed some boxers, "It's gonna be a rough day and I wet the bed last night, I should probably wear a pull-up today. Just in case." He thought.

Ash preferred to wear the girls pull-ups because he liked the designs and they just felt more comfortable on his girlish figure. He slid another pink pull-up up his smooth legs and couldn't help but get a little excited at the thought of his naughty secret for the day.

Not wanting to be late, Ash grabbed one of his favorite metal band tees and some loose fitting jeans to, hopefully, obscure any telltale signs of his padded state. He slipped on his sneakers, threw his hair into a messy, high ponytail, grabbed his Walgreens vest uniform and was out the door. He lived pretty close to work and his morning walk was usually his favorite part of the day. Unfortunately, the fresh air didn't do anything for his sour mood, which got even more sour as he walked into the Walgreens store he worked at.

"Happy Valentines Day, Ash!" His coworker shouted at him.

"Oh shit, Happy Valentines Day, Brooke, sorry I didn't even realize." Replied Ash, "I guess I'm still trying to get back to normal from my stay-cation. Didn't even know what day it is."

"Mhmm, I can tell from how you walked in. You look a little sulky. What's wrong? No flowers or chocolates today?" she teased.

Brooke. She was his work crush. About an inch or 2 shorter than Ash in actual height, her small, natural afro made her a little bit 'taller' than him. She was curvy in all the right places with a very bubbly personality. Her perpetual smile showing off her perfect teeth which contrasted with her dark chocolate skin.

"Nah, just having a really rough morning today. Why? Do you have some chocolate for me?" He teased back with a small grin. Brooke always brought his mood up.

"You wish! Well I hate to make it worse, but Matt called in sick like 5 minutes ago so it's just us two all day until the evening-close shift comes in. Fucking asshole."

"That figures. He probably drank himself sick last night. Nothing we can do though, I'm gonna get started on shit." Ash shrugged and clocked in, "I'll let you handle the register while I clean and stock and whatnot. Not really in a people mood."

"No problem, Ash!" Giving him another smile.

He couldn't help but sigh inwardly, "Single and working with my crush on Valentines Day. And I thought I was already having a rough day." He thought. Despite the terrible morning, seeing Brooke had cheered him up a bit. And getting to work even helped him clear his head and drift into autopilot. He didn't even realize it was lunchtime when he heard Brooke shout at him from across the store.

"Hey Ash! I'm gonna run out on lunch real quick, can you watch the register? You want anything?"

Getting up from his current task of stocking some shelves Ash shouted back, "No thanks, I'm good. I'll cover the register!"

A couple minutes after Brooke left, Ash had checked out the only customer in the store and was just idly hanging out by the register, surrounded by Valentines themed candies, chocolates and cheap stuffed animals, "This is partly why I didn't want to be up here." He muttered. Annoyed by all the Valentines merchandise, he left the register to continue his original task.

He was acutely aware of another customer entering the store because they walked past him a couple times, but he ignored them and kept stocking until he heard a voice ask for help.

"Excuse me sweetheart, could you help me find an item?"

"Sure, ma'am, what do you need help..."

Ash froze in his response as he turned to face the customer. He was a deer caught in the headlights. The customer was an older woman, about early 30's, in full athletic gear. She was undeniably gorgeous. Ash felt like a Hollywood movie star had entered his store.

She stood a few inches taller than him and had a light sheen of sweat covering where her clothes showed off her flawless, smooth, tanned skin. She had the body of an athlete, like an Olympic pole-vaulter. Her large breasts were gravity-defyingly perky in her sports bra. A long, platinum blonde french braid ran down her back touching her beautiful ass. She wore a loose tanktop, loose running shorts, a fanny pack and a light warmup jacket wrapped around her waist. Her nails were all painted a bright pink that matched her lipstick.

Her smile was divine. A beautiful ray of sunshine that blasted away his negative mood. "Like Helen of Troy," he mused, "Whole wars could be fought for this woman." He could feel her beautiful blue eyes staring at him, waiting for his response, "Umm, uhh, what item exactly, ma'am?"

"I'm having trouble finding the laxatives."

Ash felt himself blush just hearing this Goddess ask about such an item, trying to maintain his composure, "Umm, y-yes, please follow me." He managed to stammer out. She let out an angelic giggle as he turned and led her a few aisles over. Trying to remain professional, Ash stopped in front of the laxatives and asked, "Is that all I can help you with ma'am?"

She reached out and plucked a small bottle of liquid, extra-strength laxatives and placed it in the handbasket she was carrying, "Yes, that's all, sweetheart. But nobody was at the register when I walked in, do you mind checking me out?" She beamed innocently, as if she was naive of the double meaning.

"Of course, ma'am" said Ash.

They turned to walk to the register and, due to their positions in the aisle, Ash was behind her. The jacket around her waist blocked most of her ass, but he got a better look at her long, shapely legs. She got to the register first and unloaded her basket on the counter, while Ash took the long way around.

When he got there, he took one look at her items and turned beet red yet again. He shot her an incredulous look as he began scanning her purchases; the laxatives, 2 pints of Ben & Jerry's ice cream, extra large magnum condoms, vasoline and a bag of cheddar popcorn. "Is she serious? Is this a joke?" His thoughts were interrupted by her instigating some friendly small-talk

"Valentines Day, any big plans when you get off work?"

"Ah, um, no ma'am. No plans tonight."

"Me neither. Maybe you'd like to be my Valentine?" She asked.

He gave her the same look, his face the definition of 'Are you serious?' Her smile was still beaming, but something had subtly changed. Instead of innocence, it was now...mischievous. It took Ash a few seconds to really even process the question and, deciding it was just a playful joke, he chose a friendly response, "Sure, I'd love to be your Valentine." as he bagged her few items.

"Wonderful, what time do you get off?"

Once again, Ash was taken aback, "Excuse me ma'am?"

"What time does your shift end? If we're going to be Valentines then we have to have a date, silly." She giggled back to the stunned boy.

"I, umm..." Ash took a deep breath to collect himself, he'd never felt so nervous all of a sudden, "4:30. I thought you were joking, I've never been on a date before. I don't even know your name."

"Madeline. Nice to meet you, Ash," she said, looking at his name tag, "The pleasure is all mine getting to be your first date. How about dinner at my place, I can cook a mean steak." Madeline said, with a wink.

Still more confused than anything, Ash nodded back, dumbly, "Nice to meet you too, Madeline, that sounds great but I don't have a car. I'd have to Uber and-"

"Nonsense." said the platinum haired beauty, cutting him off, "I can pick you up, no trouble. Here's my card with my phone number. Just send me a message when you get off work and get changed. I need to get home and freshen up after my run; I've got a hot date tonight." She slid a business card across the counter and flashed him a mischievous smile once again.

"Can't wait for tonight, Ash, you've made my Valentines day." Madeline collected her bags and blew him a kiss before walking out the door.

Only moments later, Brooke returned from her munch break. Instantly noticing the boy's dazed demeanor, the first thing she said was, "You ok, Ash? You look like you've seen a ghost."

"Yeah yeah, fine. I've got a date tonight. I think I might get murdered but that would be an improvement over this morning." he shrugged.

"WHAT? A DATE?" She yelled at him as she rushed over to the register, "I've been gone for like 30 minutes and you've got a date? Spill it, Ash!"

"I'm still not really sure, myself. A customer came in and while I rang her up she asked me out since she didn't have any Valentines Day plans," he replied, blushing at Brooke's enthusiasm, "I think you actually passed her right as you walked back in."

"HER? Ash she was gorgeous! You're a lucky boy." Her shocked expression quickly transformed into a big grin as she started a little dance and in a sing-song voice, "Ash has got a date! Ash has got a date! K-I-S-S-I-N-G!"

Her energy was infectious and he couldn't help but smile for the first time today, "Okay okay, enough. Just take the register back. I need to go to the bathroom and I didn't even finish what I was stocking yet."

Brooke stuck her tongue out at him playfully as Ash turned and headed for the employee bathroom. He locked the door and stepped up to the urinal to pee and his temporarily high spirits deflated; he saw his pink pull-up. Getting to work had helped distract him but seeing his pull-up only reinforced his unhealthy thoughts, "She was just teasing me. She wouldn't actually want to date me. A beautiful woman like her would laugh me out of our date if she knew what I really liked."

Ash left the bathroom and got back work. He was totally engrossed in his own thoughts for the rest of the day, losing track of time, until he felt a tap on his shoulder.

"Time to go, Ash, don't be late for your date. Good luck!" Said his bubbly coworker.

Brooke might've teased him earlier but she was a good friend. He thanked her and bought some laundry pods, a small bunch of roses and some chocolates on his way out of the store.

"Deep breaths, deep breaths. You can do this." The blonde femboy was sitting on his bed vibrating with nervous energy. He had been staring at Madeline's card for over 10 minutes. He had gotten cleaned up and dressed in his best, and only, formal outfit. His favorite normal underwear; a pair of black silk boxers. No pull-up tonight. Some nice dress shoes, a green patterned button down shirt and a nice pair of khaki's that hugged his bubble butt a little too well. All were gifts from an Aunt over Christmas; Ash was just too broke to go somewhere he needed to dress up for. Until tonight.

"Fuck it." he muttered and typed out a quick message, hitting send instantly so he wouldn't chicken out for any longer; it was already 5:50.

"Hey Madeline, it's Ash. I'm off work and ready. You said you could pick me up, right?"

It took only a couple minutes for his phone to buzz, "Yes! Oh, I'm so excited, Ash, I was worried I scared you off earlier by being so forward. Just send me your address and I'll be right over."

He texted back his address and tried to calm the maelstrom of butterflies in his stomach as his message sat on read. He took a shot of some cheap vodka he had in an attempt to calm his nerves and he waited. It was a little over 30 minutes when his phone buzzed again, "Here" with a heart emoji. Ash walked outside, locked his door and took a deep breath as he turned towards the parking lot.

Nearing the lot, a vehicle blinked its lights at him. In the dusk it was difficult to tell what it was, but as he got closer he saw that it was a brand new Mercedes G-Wagon. "Holy shit," he muttered as be stepped towards the passenger door, "Her car is worth more than everything I own."

He opened door and there she was. Even in the poor lighting of the car interior, she was the definition of class, elegance and beauty. Her beautiful platinum hair was a carefully set nest of braids. She wore a deep crimson dress that highlighted every curve and feature of her well-defined body. She had on a light amount of makeup besides some red lipstick that matched her dress. A few gold bracelets and a pair a red heels completed her outfit. Ash tried not to stare at her breasts as he climbed into the car; they were just as large and perky without a sports bra. She flashed him a perfect smile, brighter than the sun, as she welcomed him, "Hey there, hot stuff, you dress up well! Are those for me?"

"Y-yes" was all he could stutter out as her beauty mesmerized him.

"How sweet, thank you! You can put them in the back."

He was a nervous wreck as he shut the door and buckled himself in. Ash managed to relax and loosen up as they drove and talked, his mind reassuring himself, "This is real. This is really happening." Despite how out-of-his-league he felt she was, Madeline was incredibly amicable. Her friendly demeanor quickly melted away the nervous boy's jitters, and Ash was soon laughing and joking with her as they idly chatted through the evening traffic.

They had drove about 30 minutes from Ash's apartment, into the suburbs, when they arrived at the entrance of a gated community Ash had only heard about; he was too broke to have any business around here. Madeline pressed a button on a small remote and the large, hugely ornate gate creaked open.

Ash couldn't help but gawk at the inpressive entrance. "Wow, Madeline. I've never seen anything like this neighborhood before. What do you do to live in a place like this?"

"Did you not read my business card, sweetie?" she giggled at him, "I'm a doctor. A psychiatrist. I'm blessed that my family is rather wealthy and connected. I only take high profile clients like CEO's, local celebrities and executives. And I only take a minimum amount of clients to keep my license. It honestly bores me now. I'd much prefer to be doing something simple like a personal trainer."

"I see..." was the only response she got as Ash stared at all the mansions, mouth wide open, as they slowly drove into the neighborhood. The car eventually pulled into the driveway of, yet another, opulent home and came to a stop inside of a high-ceilinged four car garage.

"Here we are, home sweet home," Madeline said as she turned to her bewildered date. Ash met her eyes as her smile beamed at him, "Let's go inside. I'm starving!"

She reached for her door handle and Ash cried out, a little too loudly, "Wait! I got it!" He scrambled to hop out of the vehicle and ran over to her side of the car, opening the driver door and offering his hand, "Please, allow me, madam."

She took his hand and stepped out, giggling, "What a gentleman, thank you, sir." She led the way inside the house and, once again, Ash was stunned. The home looked like something he had only seen in movies. Beautiful, rich hardwoods floors. Expensive art decorated the walls. High vaulted ceilings with sparkling crystal chandeliers. He was practically spinning in circles taking it all in. He could see a dimly lit study with filled bookcases dominating entire walls of the room. A living room area with the margest TV he'd ever seen outside of a movie theatre.

"Wow, Madeline, this is something else." he said breathlessly.

"I can give you the grand tour later, if you'd like, come keep me company while I start dinner. Do you have a drink of choice?"

He followed her angelic voice into a kitchen that would rival Micheline starred restaurant kitchens and took a seat on a bar stool opposite the counter where she was washing her hands with her back turned.