Bedwetter Ch. 01

Notes from the author: This story has a number of fetishes at work together. Including female domination, pegging, feminization and diapers so, if that's not your thing you may want to skip. These stories are long but I try to include a bit of character building and setting up future installments so I hope you like to read. With that, enjoy...

It all seems so long ago. One could say a lifetime ago, when I was an entirely different person. I was a man believe it or not, a painfully average man but a man nonetheless. If I was pressed to tell you exactly when the world got flipped upside down for me I suppose I would say it was shortly after I had lost my construction job and with the state of the world these days, it was next to impossible to find anyone working, let alone hiring. I had always been a reliable employee and the kind of guy who never had to depend on anyone but after weeks of phone calls, endless hours driving and application after application, things were getting really grim. I had my girlfriend who never seemed all that worried about me being unemployed, we lived together in our little apartment and she was a nurse so she was capable of handling most of the monthly bills without much of a problem but it really ate away at me having to depend on her. I was grateful for her, she never once complained and even seemed happy to shoulder the financial situation, always saying "don't worry, Baby, Momma's got this."

Things really took a turn when I, a twenty-one year old man, began having nightly "accidents". At first it wasn't all that bad, a little leak on the rare occasion but things quickly deteriorated and soon it had become a nightly ritual to change the sheets. I tried everything you could think of until one night Alli brought home a package of pull-up diapers. I was mortified. She sat me down, took my hand in hers, looked me in the eyes and very calmly told me, "sweetheart, I love you and I know this is hard on you." She was so sweet and understanding, even changing the soaked sheets at three in the morning, she had never so much as raised her voice. When she asked me, "can you please just wear them for me so I can get some sleep?" I just didn't have the heart to fight her. Like she said, it was just for right now, until whatever this problem was went away but, deep down, I had been obsessing over when this would just end and was starting to worry it ever would go away.

That first night, I had stepped out of the steaming shower, towelled off and stepped into our small bedroom where Alli lay, comfortable in her tiny t-shirt and white panties, on our bed. She smiled at me as I stepped into the room, wet and naked under my towel. I smiled back and leaned in to give her a kiss before I stepped away towards my dresser.

"Whatcha doin, Sweetie?" she asked.

"Getting ready for bed," I said as I reached for my drawer full of boxer shorts.

"Baby, remember our talk?" she said softly yet strangely motherly.

I froze inside, sighed and realized that I, a grown man, had to wear a diaper to bed.

"Yes, I remember," I said joyless and ashamed.

She smiled and turned back towards whatever movie she had queued up on the television, a bad Bruce Willis flick if I recall. "They're in the plastic bag in the kitchen," she said with just the slightest touch of cold satisfaction.

I turned without looking at her and made my way down the hall, past the living room and into the less than clean kitchen where I found a gray plastic bag from the pharmacy. I grimaced and pulled the pullups out of the bag, shocked to find that they were girls' pullups.

"Babe, seriously? You got girl ones? I can't wear these," I said as I marched them back into the bedroom, package in hand.

"Sweetie, they didn't have boys ones that would fit you, I'm sorry but I just didn't have time to run all over to find you diapers. Please just wear them for me, you'll thank me when you wake up tomorrow morning in a dry bed."

I stared at the package in my hands. These were literally pull-up diapers for girls, the purple plastic packaging showed a pink diaper with a cutesy cupcake pattern for crying out loud. I just could not believe I was being asked, by my beautiful blonde haired, blue eyed girlfriend, to wear girls' pullups to bed because I had a bed wetting problem. The total lunacy of this situation really began to weigh heavily on me.

"There's no way these are going to fit, Alli." I muttered in one final, desperate protest.

She sat up and pressed against me, her soft breasts against my shoulder, her sweet lips whispered in my ear, "if you wear them to bed I promise I'll make you cum hard tonight."

I grinned and pulled my towel away, leaning towards her to kiss those soft, pink lips but she pulled away and sat back in the bed, a wicked grin on her lips, her eyes locked on mine with a steely, almost predatory, coolness, "diaper first, Babe."

I sucked my teeth, tore open the plastic and removed one of the soft, crinkly and pressed diapers. There's no way this will fit, I thought. I wasn't a big guy by any means, I was sleek with toned shoulders and my arms had gotten firm over the past few years swinging a hammer but still one of the smaller guys on the crew. I stretched it out and hated to admit the soft, cotton interior felt strangely familiar and surprisingly cozy when my hand slid into the pink pull-up to stretch it open.

Alli giggled and watched as I reluctantly stood up and stepped into my ridiculous new sleepwear and gently slid it up my legs. It was snug for sure but it fit and I couldn't help but feel oddly comforted by the moderately thick padding wrapped around me; the soft cotton hugging me between my legs, the gauze-like waist, the plastic sound, that adorable little crinkle, as it slid up my body.

"That's so cute," Alli said, "I never noticed how little body hair you have either, you look adorable!" she giggled.

I rolled my eyes and crawled over her onto my side of the bed, quickly getting under the covers.

"Awww," she teased, "is someone embarrassed?"

I pulled the thick covers and bedsheets over myself and went to my side. I felt Alli give chase after she shut the light off and got underneath the blankets. She was behind me and I swear I could feel her smiling wickedly when I felt her hand gently patting my soft, diapered bottom.

"So cute," she cooed in my ear. Her cold little hands traced around, over my hips where she playfully tugged on my thigh to signal her interest in the front. I hesitated for just a moment before shifting slightly and making a small opening between my legs.

Her hand gently traced along the front of my pull-up, she moved the palm up and down, pressing ever so slightly against my cock which began to swell in the confines of the cotton diaper. Her fingers went to the elastic seam and played with it, easing a finger inside where her smooth fingers would brush against my swelling member, stroking me just barely before slipping out again.

She held me, her breasts against my back, her warm legs behind my own. She would whimper softly in my ear, telling me she wanted me to cum in my pampers like a good boy should...but only when she said so. It was strange to hear her in control. Our sex life had went stale for a while, especially since I had lost my job but perhaps, with her handling the bills and me needing diapers, she felt like the one holding all the cards.

I was straining in my pullups. They were so snug my cock felt trapped inside the soft cotton, it simply throbbed against the plastic and after a while of her teasing, my pullups definitely became sticky with precum. She continued to rub me over the diaper, she was loving every second, every time I squirmed or whimpered or begged her to let me take it out she would just hold me tighter, rub me harder and softly shush me which just made me throb harder and made my diaper all the stickier.

Alli had me at that moment, I was her plaything at that moment. While she would take me even deeper, at that moment, I knew deep down that there had been a major shift in our relationship but before I had time to dwell on it, she reached under the bed and pulled out her pink, vibrating wand massager.

I watched her as she leaned back, the smile on her face was alarming but when she told me to turn over on my hands and knees I didn't question her. I knew in my mind that I didn't like the idea of being in such a position but the throbbing and straining between my legs was unbearable and I knew she had plans of making me explode and so I did as she asked. I was on my elbows and knees feeling vulnerable and out of my element while she shifted and moved behind me, all the while with this look of absolute satisfaction on her face.

"Good boy," she said enthusiastically.

She gave my pampered bottom a swat with her hand, the blow absorbed by the cotton seat of my pullups with a dull thud.

Her hands caressed my padded backside before she ran her hand between my legs and pressed her palm against the bulge in my pampers. The sensation of being so exposed to her, that helpless feeling of submission was so intensely overwhelming and when she told me to spread my legs and "get that cute little tush in the air," I felt myself leak into that soft, cotton padding of that little pink pull-up.

I heard the wand click to life and Alli slid the bulbous wand-head between my legs and against that little bulge she had caressed and teased just moments ago. The vibration of that wand against my diapered cock was so euphoric, she continued to run the wand up and down the outline of my member as well as my taint and even pressing it firmly against my ass while all I could do was squirm, whimper and beg her to make me cum. She would keep the head of the wand firm against my bottom but she would lighten the pressure when she would brush against my aching cock, tormenting me as it kept me on the edge of orgasm, the vibrations, soft enough to keep me leaking in my pullups but just outside the threshold of total meltdown.

When I began pressing my hips down against her vibrating wand when she passed it by, she began swatting my padded bottom, "are you my little diaper slut?" she would ask. "Tell me you want to pump your load into your diaper like a good girl."

I was so lost to her smacking my ass and her vibrator that I simply gave her whatever answer she demanded of me until she finally pressed that wand against my cock and gave me "permission" to cum in my diaper. I came buckets, shooting into my pampers and moaning like a bitch, my ass in the air and my little blonde girlfriend giggling and pressing her vibrator against my cock until finally the orgasm began to fade. I realize now she was preparing me for a very different bedroom dynamic.

I continued to wake up in a full diaper every morning. The little pink pullups really were something, they were swollen and sagging each new day but the sheets were dry and Alli had no more sleep disturbances. Every night she would come home and for the better part of a week she would make me cum in my diaper using her wand until one night she decided to add a new element to the mix.

I had been used to the routine, I would pull on my pullups, get into bed where she would cuddle me and kiss my ears. She was always the big spoon these days, her breasts on my back, her hands groping and rubbing me, making my cock hard and trapping me in my snug, cotton padded prison before she would get me on my knees and drive me howling mad with "Mommy's Magic Wand" (she also had me calling her "Mommy" these past few nights) before she would let me cum in my diaper but this night, after I had gotten into my new favorite position, she gave me a playful slap on the bum and said, "Baby, we're going to try something new, OK?"

I was eagerly anticipating the wand at this point but she told me to trust her and I finally agreed.

She smiled and ran off before returning a moment later with a bottle of lubricant in hand. She rolled the waist of my pullups down just a bit, I was still very much in my pampers only now my bum was exposed and I had a bit more room for my cock to hang between my legs, I could feel my tip on the cotton padding inside my pullups, a small, sticky wet spot had formed from Alli's attention.

"What are you doing?" I asked sheepishly.

"Trust Mommy, Princess," she said as she squirted a liberal amount of clear jelly into her hands before snapping the bottle closed and tossing it into the bedsheets. She rubbed her hands together before she began massaging my cheeks, the warm liquid spread all over my bottom and while I had my suspicions, I certainly wasn't prepared for her finger. I gripped the bedsheets, my eyes widened and my mouth dropped open as she slid a finger deep inside me. It was a bizarre sensation unlike any other I had experienced with her before but it soon became comforting as she began to rub and massage what she would soon be calling my "boi pussy".

She began to really get deep inside my ass, I squealed at first but soon began to whimper and moan as her fingers explored and searched. Her free hand slipped between my legs and into my pampers, there was little room but she took my soft balls in her hand and rubbed them before her small fingers gripped and squeezed my throbbing, constrained cock.

The fingers in my ass slid in and out, she would occasionally add more lubricant, spreading it all over my hole before her fingers slid effortlessly inside me and her fingers probed tirelessly until she found that special spot that made me knees weak. She would turn me into a squirming mess when she would press that spot somewhere behind my coin purse; I could not for the life of me contain my squeaks and noises.

"You like that, Sissy?"

I was taken aback by her calling me that, a sting against my shrinking masculinity but when I hesitated to answer she stopped her fingers and I knew she demanded an answer to her question.

"Yes, Mommy," I said dryly.

"Good Girl."

I instantly felt her press that special spot again and she continued to fondle my cock.

"You like when Mommy fucks your little pussy?"

I could feel myself squirt in her hand when she said that. I knew things were different these days and as good as it felt I felt a wild sting of shame washed over me as I lay on my hands and knees, ass up while my girlfriend milked my cock and buried her fingers in my ass.

My little pink pullups were just barely hanging on but she never let my cock free from it's cotton cage. She quickly stuffed a second, and then third, finger into my rump while her other hand molested my undercarriage; she would palm and rub my ball bag or give just the tip of my aching member a squeeze or tiny strokes using just her thumb and index finger as she made the best with the space in my pampers. Her fingers in my ass had ceased their delicate exploration. She would go deep, her slick fingers buried inside of my ass to the knuckle where she would flick and rub that spot again and again.

In my mind I tried my best to keep my manhood in check, the mental gymnastics and justifications I insisted on telling myself would certainly collapse if I removed any surface level observations I was repeating over and over in my head. I told myself this was normal, it's nothing to be ashamed about, right? I mean, she was my girlfriend and nothing a man and woman do in the bedroom could be construed as "gay" or "weird". Right? But, the fact was, I was a young man, in a pink pullup diaper, on my hands and knees with my girlfriend's fingers stuffed deep in my ass while she teased and milked my cock...and I absolutely loved it. Alli had adapted quickly to her new role in the bedroom. She had little to no desire whatsoever to go back to our former dynamic and seemed to take some sadistic pleasure in having me bent over in front of her while she finger fucked my ass. Her giggles when I buckled under the pressure of her thrusting hand were both arousing and stinging on a primal level; she was no longer the timid little cutie I had fallen for, she was becoming colder and less patient.

"Are you Mommy's diaper wearing Sissy?" It was more factual statement rather than question.

I whimpered and my knees turned to rubber as her fingers pumped and pulled out of my hole. My diaper was slick with precum as she simply refused to bring me to the edge of orgasm; those soft fingers knew just how to play and pull or squeeze, with surgical precision, she held my explosive finish just out of reach as I pressed my face into my pillow trying my best to keep my rubber knees balanced. If my body began to slump, Alli gave my bare ass a slap and, almost with a grunt, she would correct me: "ass up, Princess."

The assault on my ass was relentless and I felt my body ride wave after wave of release yet never crossed the border. She teased me, relishing in my newfound submission, "tell Mommy how much you love having that little ass fucked," she sneered.

I struggled to answer and paid for my pause with another hard spank.

"Sissy, Mommy asked you a question," my mind was spinning from all of these new sensations, the three fingers in my ass, the diaper hugging my thighs and hips, her little strokes, her commanding and lustful words degrading and humiliating me. If her initial question wasn't wounding enough, she added, with a helping of condescension, "You don't want to cum in your pampers tonight?" Her fingers in my pullups, that magical thumb-index combination that I had come to crave and obsess over had suddenly released me and I knew I had to answer.

"Please, Mommy, make me cum in my diaper," I squealed into my pillow.

My cock was rock hard in my pullup, it hung into the crotch of that lovely, soft cotton webbing, an ungodly puddle of precum had already started to soak into the padding and Alli, smiling that evil grin she wore so frequently, began a heavenly rhythm with the three fingers in my ass. She would wiggle those little digits, deeper and deeper until she was knuckle deep and I knew she was about to pounce on that wicked little button tucked up and inside my newly discovered "boi pussy."

When she suddenly pulled away I wasn't entirely sure what was happening. Had I not heard one of her questions? I twisted my head to the side of the pillow, my face had been pressed into a pillow, my body slumped forward, my slick, bare ass blowing in the breeze, the strain and longing for release between my legs and even my hole suddenly so empty. That particular thought hit me. I realized how deep I was around that time but I had no idea just how far things were heading.

Alli hopped back into bed, I saw that smile once again, her eyes were locked on my own, looking down at me from behind, like a lion who just found dinner.

"What's that?" I asked, my eyes now inspecting the black cone-shaped object in her hand.

"You'll see, Sweetie," she beamed, she quickly dug into the sheets to find the clear bottle of lube.

She applied a healthy amount and stroked the rubber come before she looked back at me. "This is your new plug, Baby. You'll be wearing this a lot," she said, emphasizing those final two words.

I didn't reply, I simply buried my face back in my pillow as she rubbed the rubber tip between my cheeks. That sensation was intensely overwhelming, my lubed bum, the rubber tip was a mini-cock and Alli traced it up and down, pressing it just slightly against my eager hole whenever she would pass it. She ran it down my soft taint which welcomed the attention, Alli continued up and under, tracing up and down the shaft of my constrained cock and I could feel the bead of cum form on my tip and melt into the cotton fiber of my pampers. The whole experience, every single variable of my present situation, was so incredibly overpowering but when she finally slid the plug into me, my cock twitched and I felt that wet spot in my diaper grow just a little bit larger.