My Diaper Valentine Pt. 01

"Moscow Mule please. What are we having?"

Spinning around to face him, she grinned, "Steak, lobster and baked potatoes. The perfect Valentines Day dinner. And I made brownies for dessert." Opening some cabinets and a trip to the fridge, she set out some bottles of alcohol, ginger beer and a lime. It took her only a few moments to prepare the moscow mule and set it in front of the boy, "Drink up. I hope it's to your liking."

Ash took a sip and besides being a little more stiff than he would like, the drink was delicious. Madeline made herself a martini and got started cooking. With the alcohol flowing, the conversation flowed as well. Ash marveled at her culinary skill as they talked a broad range of subjects and topics. Trading stories and learning more about each other.

Ash was two and a half moscow mules deep by the time they finished dinner and definitely feeling a little tipsy. He plopped the final bite of his brownie into his mouth and leaned back in his chair, staring at the beautiful woman across the table, "Madeline, that was amazing. I've never had food like that before, even from a restaurant. I've had an amazing night but I can't hold back my curiosity any more; what was up with the stuff you bought earlier? I thought I was in a YouTube prank video or something."

Still staring at one another, Ash watched her smile change. In that instant, he knew why older women were sometimes called cougars; he felt like prey. Her smile was predatory.

"Lets play a game," she ignored him, "You ask a question, then I ask a question. No lying."

Filled with alcohol, Ash shifted uncomfortably in his seat, "Umm...ok I guess. Were you trying to prank me earlier at the store?"

"No sweetheart, the icecream and popcorn were all for my lonesone self if you declined my date or didn't show. The other...items were if you DID accept my date." Her voice was sweet but her smile and gaze made the young boy gulp.

"What do you mean-"

"Ah Ah Ah!" She cut him off, "One question, then it's my turn. You agreed." Ash slowly nodded his head as she continued, "My turn; did you wear a diaper here tonight?"

He felt his face flush with heat and turned more red than the lobster they just ate, "I-I've got no clue what you're talking about!" Ash said, a little too defensively.

Madeline stood up from the table, maintaining her gaze she spoke softly, "Don't lie to me, Ash. I've been lied to and had my heart broken more times than I can count. I know your secret. Why do you think I chose you? Why do you think I asked you out?"

"I..." he paused and hung his head in defeat. She knew his secret. Even if he tried to lie, his body language had already told the truth. He took a deep breath, "No, I didn't wear a diaper out tonight."

"Good boy, thank you for telling me the truth." Sexually inexperienced though he was, Ash could detect the sexual tension building. Her voice dripped with lust as she dragged a single long, pink fingernail across the dining table and slowly approached him, "Such a good boy." Her manicured hand gently landed on his head and lifted it to meet her gaze, "Your turn, sweetheart."

"How?" A lone word was all he could muster. Between him still sitting down and her heels, she towered over him. He tried to shrink into his chair as her presence dominated him. He wanted to curl up and die.

"I'd like to think it was fate," she replied. A less predatory smile flashing across her face for an instant, "I only stopped in to get some icecream and popcorn after my run. No date on Valentines day; I figured I'd just stay in and watch a movie..." Her eyes betrayed a pang of sadness, "But I walked past you. You were crouching down to the bottom shelf and your shirt was riding up. I saw the pink pull-up waistband; I'd recognize it anywhere. I couldn't see your face or anything so I got the idea to ask you for help with the laxatives. And when you stood up...you were so cute, so flustered. I knew instantly I had to have you."

Ash was on the verge of tears. This sort of exposure was too much. He was feeling a whirlwind of emotions and the alcohol wasn't helping. He broke her gaze to look for his napkin and wipe his blurry eyes, "You recognized my pull-up? So you're into diapers too?

"Yes, sweetheart. Or rather, I'm into cute boys who wear diapers. I prefer to be the mommy."

"What about the condoms and laxatives then? You just wanted to embarrass me?"

Before she could answer, Ash's stomach let out an audible gurgle and he doubled over, clutching it. A wicked smile lit up her face and she grabbed the boy's ponytail, wrenching his head back up to meet her gaze once again.

"You want answers? You submit to me right now. Call me Mommy, right now, I make your dreams come true. If you say no, I'll take you back home no questions asked and you'll never see or hear from me again."

Ash sat and contemplated the offer. It seemed like minutes passed, the silence only broken by more gurgling from his stomach, until he finally squeaked out, "Yes, Mommy."

Madeline's grip on his ponytail softened and she pulled the sitting boy into a soft hug, his head resting against her toned tummy, "Good boy, good boy," she cooed as she stroked his long hair, "The laxatives I can already hear working; they were in the brownies..." Ash tilted his head up through the embrace, barely able to make eye contact with his new mommy because of her breasts, his face painted with distress. She broke the embrace as she took a step back and continued, "And the condoms are for me."

Even todays rollercoaster of emotions and events couldn't prepare Ash for what happened next. His new mommy pulled her dress up and his mouth dropped open as he stared, nearly eye level, at a rapidly growing bulge in her panties.

"This is what I meant by the heartbreaks...I'm a futanari. My whole life I've been treated like...like I'm just a walking cock looking for a fuck. Like I don't have feelings of my own just because I'm a futa. I'm sorry for deceiving you, Ash, I'm sorry for trapping you in my crazy plan. I'll take you home if you want...it just felt like fate when I saw you; I've never had someone to be with on Valentines Day. Never had a special connection with someone..." Madeline quietly tapered off, displaying weakness for the first time all day. The pain and sadness was plain on her face and it looked like it was her turn on the verge of tears.

Confliction tore through the boy's mind. The first and most obvious thought being, "I'm not gay." but he quickly brushed that aside; Madeline was a goddess of unequivocal beauty. She transcended normal sexuality. And besides, futanari's have vaginas right? What's the big deal. Nobody would ever know except him.

Ash couldn't deny the aspect of fate. The date was a fantastic experience leading up to this moment. They had talked and laughed throughout the whole night, getting along famously. He felt like this deeper view into her heart only served to draw them closer; a fellow kindred spirit battling loneliness and searching for acceptance. He wanted to try. He wanted to stay. He wanted a Mommy.

Breaking the silence once again, the boy spoke quietly, but confidently, "No, Mommy, I want to stay, but...I might have an accident soon." His stomach was in turmoil and he gripped his midsection. Ash had always been curous about messing his diapers but never tried, for a multitude of reasons. But now...he was trapped in her web.

"Oh Ash, you're a good boy. My beautiful darling boy," she sniffled and wiped her eyes, "You wait here. I'll be right back."

Madeline momentarily disappeared and returned with a speed that was truly impressive considering the heels she was still wearing. She returned with a large, fluffy, pink Megamax diaper in one hand and a changing mat in the other. She flashed him that smile and knelt down on the hard floor. She spoke as she unfurled the mat and fluffed out the diaper.

"Ok Ash, we can discuss limits and kinks later but this is non-negotiable. I know it's not fair for me to start our relationship by secretly giving you laxatives, but you need to learn that Mommy knows best." Her tone was sweet but had an underlying edge that Ash didn't want to test, "You're going to give up control tonight and be a good boy for me. And tomorrow we can start fresh." She punctuated the end of her speech by gently patting the open diaper.

Ash nervously stood up and reached to undo the buttons of his shirt before he paused, "Mommy...I'm a virgin. I've never gotten undressed for anybody before."

His beautiful Mommy stood up and approached him. She, exaggeratedly, tapped her chin. Faking a pensive gesture, and spoke, "Hmmmm, I wonder if my sweet boy is embarrassed being the only one getting undressed."

She reached for the straps of her dress and slid them down either shoulder as she wiggled. The crimson dress fell to the floor, revealing the most breathtaking sight of the young boy's life. Her breasts were spectacular. Double D's with only a hint of sagginess that betrayed her age. Her pink areolas occupied a perfect ratio of not-too-large-not-too-small, and her nipples stood proud like a pair of pencil erasers.

His eyes drifted down her body, drinking in the view. She looked like a Greek statue; as if she was chiselled from marble. She had defined muscles everywhere with the slightest layer of motherly pudge smoothing everything out. His eyes came to rest on her crotch. Her black lace panties contained a monster, but just barely. It looked to be twice the size of his own cock in every metric. It strained against the silken garment, a large wet spot visible where the tip appeared to be. Her tall heels helped enhance her legs and butt in a way that had Ash's mouth watering. She embodied perfection. Ash was petrified by her beauty, his hands freezing before he had unfastened a single button.

She leaned down and whispered in his ear as she gently slapped his hands away, "Let me help, sweetheart." Madeline deftly unbuttoned his shirt and paused after she removed his shirt, "How about I get a little closer." She kicked off her heels and knelt down in front of the boy. Her manicured hands danced across the front of his belt and pants. The belt buckle clattered as it hit the floor, breaking the trance his goddess had him in. He didn't even notice that his own cock was rock hard until now.

"Fucking beautiful, Ash, Oh my God." Madeline nuzzled her face against the significantly smaller package in his boxers, while her hands explored him. Her nails tickled his toned legs before she reached back to grab a handful of his bubble butt. She moaned as she molested his ass and removed his underwear, his freed cock springing straight ahead. Ash was breathless with anticipation.

His stomach was still doing flips but Madeline's teasing and groping provided him a sensory experience that had him about to explode. Ash let out a gasp and a cute mewling whine as his Mommy moved a hand to his cock, gently pulled back his foreskin and took his leaking tip in her mouth. The virgin boy shut his eyes in pleasure, savoring the feeling despite the brevity of the act. Her mouth was only on him for a few seconds before she pulled back, licking her lips, and whispered to him.

"Just a quick taste, my sweet, now lay down for me."

Ash did as he was told. He had never tried the Megamax diapers before and they blew him away. It felt like he was laying on a cloud. He was so distracted by the luxury of his new diaper that he didn't notice the icepack that had materialized in his Mommy's hand, "Ahh!" He gave a quick yelp as the ice touched his crotch, his eyes darting to his Mommy. She wore a wolfish grin.

"I'm sorry sweetheart, I know its cold, but I was never going to get you taped up with you so excited."

Ash whimpered as his, now soft, cock was enclosed the the fluffy padding. Another jolt of pain shot through his stomach, his eyes begging for relief as he admired how skillfully Madeline got him changed. She easily lifted his butt and legs and positioned him as she saw fit, not needing to ask the uncomfortable boy to help at all. The sound of the tapes and crinkling diaper seemed to echo around the cavernous kitchen as, adding to the chorus of gurgling coming from Ash's stomach.

"There we go, all set!" She said as the final tape was applied, "Let me help you up, sweetheart."

She stood and grabbed his hands, easily helping him to his feet. Ash had obviously noticed their size difference, her being taller and stronger than him, but standing before her wearing only a pink diaper made him feel even smaller. She had gotten him changed without even needing his assistance.

The gorgeous futanari removed her panties and sat back down in her chair, fixated on the submissive boy. The desire was plain on her face as one hand began to stroke her impressive member. She was uncut and totally hairless. Over nine inches of girthy futa cock pointed directly at the boy. Her large balls looked like two jumbo eggs, gently swaying as she slowly masturbated. In contrast to the rest of her tanned body, her crotch was much paler, "Tan lines." He thought, with her cock and balls a rosy pink with arousal. Pre-cum was leaking out, making her fingers visibly slick as she stroked.

"Use it."

It was a simple command. She whispered it with an authority that Ash dared not disobey, despite this being the most humiliating experience of his life. He was rock hard in his diaper and it took a minute of focusing before he managed to obey. His bladder released first; a faint hiss joining the sound of his Mommy's rhythmic stroking. That was the easy part. Ash grunted as he squatted slightly and released a few muffled farts. He bore down even more, not wanting to disappoint his Mommy.

"Aaahhhh!" He groaned with relief as his mess exploded into the diaper, "Oh fuck..." It was a lot. The extra strength laxatives had done their job well and Ash felt like he was unloading days of waste into the pink diaper.

"Yes! That's it, good boy!" Madeline moaned the encouragement as her hand picked up speed; she was nearing the edge.

Ash was disgusted. Partly because of the smell that immediately filled the room. Partly because of the huge amount of soft, semi-solid shit that flooded his diaper and seemed to coat his whole ass and groin. But mostly because it was the most pleasurable experience of his life. He couldn't believe the ecstasy he was in. The warm, slippery mess felt delightful as he straightened back up and moved a hand to his behind, cupping the sagging diaper. His Mommy broke him free from his introspection, "Come here, sweetheart, kneel."

Ash started to protest, "But-"

"I said kneel. Now." She gave him a look that made him afraid of the consequences of being told a third time. He quickly waddled the few feet between them and gingerly knelt down. Waves of pleasure rushed over him as he distinctively felt some of the mess squelch up the front of the diaper, making contact with his cock and balls.

"Tongue out."

He didn't hesitate for this command and stuck his tongue out as far as possible. His Mommy stood and towered over him as she grabbed his ponytail to hold him in position.

"FUCK! Yes, Ash, YES! She screamed as she climaxed, the massive futa-cock erupting onto the kneeling boy's face. Truthfully, she was aiming for his open mouth but she ended up coating his whole face, with more than a few spurts landing in his hair. Ash dared not to close his mouth or move, quickly accepting his role as a cum receptacle. To Ash, it felt like like she was cumming for minutes until she finally collapsed back into her chair, panting, "Holy fuck, baby...you're a quick learner; go ahead and swallow."

Permission granted, he gulped down the mouthful of cum; it wasn't as bad as he expected. It was viscous and warm but the flavor wasn't totally unpleasant. If it was from his Mommy then he would learn to love it. Nearly blinded by the sticky coating, he heard that angelic giggle as she spoke.

"I'm sorry, sweetheart, I didn't mean to make you such a mess. At least not anymore than you already were. I'll get you cleaned up in the shower."

Ash started to rise, but before he could actually stand she hooked her hands underneath his arms and effortlessly lifted him. Once again, he was blown away by their physical differences. She carried him with one hand on his butt, squishing his diaper and intentionally spreading the mess around.

It had been quite a wild day for the petite boy and being carried by his Mommy helped him slip into a deep sub-space. He held onto her, nuzzling his face into her chest, and let out tiny whimpers as his most sensitive parts grinded against her flat tummy with every step. Despite everything that had just happened, it wasn't a sexual act for Ash. He just wanted to be close to her; this was his first time actually touching his Mommy. He closed his eyes and savored the feeling of her smooth, warm skin against his own.

She carried him into the master bathroom and gently put him down in the giant walk-in shower. Madeline turned to rummage through the vanity and Ash took the opportunity to scan the room. The shower alone was practically the size of his whole apartment bathroom. It had a natural stone floor with multiple jets, shower heads and other implements spaced along the walls. There was a massive jacuzzi tub in one corner. He could the see toilet through an open door on the other end of the room, "Probably won't get to use that." he mused to himself.

He looked back to his goddess, bent over in her search, and the sight made him realize how painful aroused he was. Mere feet away was the most perfect ass he had ever seen. Her tanned cheeks looked pillowy soft and where they met in the middle was a sliver of pale flesh where her thong had rested when she tanned. This view allowed him the tiniest peek at her vagina and he swore he could see it glistening from where stood.

His Mommy finally turned back to him, holding what appeared to be a bar of soap, wash cloth and a couple trash bags. She stepped into the shower, smiling sweetly, and spoke, "Kneel." Ash didn't hesitate this time. Instantly coming face to face with her monster cock. After all he had been through, it didn't surprise him when the golden stream hit his torso.

"Aaahhhh, good boy, good boy." She quietly whispered as she relieved herself on the motionless submissive. Taking hold of her cock, she hosed him down. Adjusting her aim from his torso to his beautiful cum-covered face. Ash closed his eyes but didn't recoil, even opening his mouth to provide a better target. Similar to his own mess in his diaper, her piss was a warm and pleasant experience. It was mostly clear and tasted faintly salty as he swallowed a mouthful. She shook the last droplets onto his waiting tongue as her stream tapered to an end and helped the boy to his feet once again.

"You've been such a good boy, let me take care of you now." She whispered into his ear and gave it a few nibbling kisses before she knelt down in front of him. Her practiced hands unfastened the diaper and it fell to the floor with a wet, dull thud.

Despite all the events of the night, Ash was truly unprepared for what happened next. Without hesitation, Madeline swallowed the entire length of his sludge-covered prick. Her pink nails reaching around behind and digging, almost painfully, into either of his his cheeks. Totally unphased by the layer of shit coating his ass and groin, she pressed against his butt, trying to force him even deeper down her throat. The virginal boy had endured a marathon of stimulation throughout the night and feeling Madeline's mouth again was all he needed to push him over the edge. He came almost instantly, screaming, "MOMMY!" as his hips bucked and he blasted his comparatively insignificant load in her mouth.

Searing white pleasure overloaded his senses and his knees threatened to buckle, being held up more by her iron grip than his own legs. She continued sucking well after his orgasm subsided. Her mouth massaging every drop out him that she could. Ash's chest heaved as he panted, trying to recover from the total sensory overload. Almost unaware of his Mommy standing back up and reaching for his throat with a shitty hand.