Bedwetter Ch. 02

Story Info
A man adjusts to new routines in his relationship.
11.4k words
4.75
30.2k
27

Part 2 of the 2 part series

Updated 06/10/2023
Created 10/01/2021
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Notes from the Author: this story is the second in a two part (for now) series. It contains themes of female domination, feminization, pegging, diapers, cross-dressing and interracial sex. All characters of above legal age.

On the days Alli had off, it wasn't uncommon for her to spend the day making me try on outfits she had ordered online for me and, generally speaking, pounding my ass as often as she liked and today was no different. As usual, I woke up soaked. My pampers must have weighed five pounds, the warm, damp cotton was ridiculously swollen between my legs but my soggy bottom was even worse; as I laid in bed in my favorite pink babydoll, looking down at the bulging pull-up, I attempted to close my thighs and, while I could cross my feet over one another and touch my knees together, there was just no way my thighs would close with my full diaper. The pink pullup now had a light plum tint, my night time accidents refused to go away but, at this point and since Alli had me in diapers around the clock, I had long since given up; besides, if I'm being entirely honest, sometimes I wouldn't even realize I had gone.

It had been almost two months since I lost my job, another problem I didn't seem particularly worried about these days as Alli, or Mommy as I called her, had pretty much ruled that out as a possibility; "what? With you wearing diapers to work?" she had often reminded me. In public I still went out as "the man", my hair had grown out a bit and my chest was, for some insane reason, developing but it wasn't anything anyone seemed to pick up on. At home I was Mommy's Sissy all day, every day. She dressed me every morning before she left and my outfits were anything but masculine; pink dresses, yellow dresses...dresses, always a dress; Mommy figured, with the pull-ups and my frequent accidents, there was absolutely no point in anything else, plus it was easier to check and change me should the need arise. She had good taste, my clothes were never comically feminine but rather cute and in fashion. She dressed me like her own sister but we both knew I was her pathetic and helpless little Sissy Baby.

Let's see...what else has happened since my last journal entry? Well, I was still plugged every day. Not much has changed there, Mommy loves keeping me squirming and waiting for her but the plugs have changed a bit. First, Mommy had bought a Princess Plug for me, an adorable jeweled plug with a stainless steel body and shiny, pink jewel you would find pressed between my cheeks on any given day and at any given hour but that one would be replaced with a similar plug, the second being a much larger "plug". Going up in size wasn't much of a shock I'm proud to say, Mommy has definitely been training me with bigger, larger and wider toys, always testing my boi pussy and it's limitations and when the latest jeweled plug arrived, it slipped in with little resistance. Oh! I'm now caged as well. Sure, it's a bit of a hassle because Mommy has to clean it every time she changes me but I don't mind at all; Mommy says it doesn't need to get hard these days and, honestly, she's right, I've been having incredible orgasms with her cock buried in my ass or when she lets me ride her Magic Wand. She loves watching me hump away, straddling that bright pink vibrator like a desperate little slut and, as usual, I've always enjoyed riding it until I pump my diaper full of my cum. I've got to say, I've really come a long way since those early days and Alli has really helped me along.

"Baby?" Mommy groaned as she rolled over in bed, her big, black cock suddenly pressing against my swollen, diapered bottom; she had really grown to enjoy wearing that thing, even sleeping in it many nights. I felt a dribble of precum leak from my tiny, caged sissy-clit at just the thought of her using my pretty pussy this morning. I've noticed, since Mommy locked me away, I'm constantly in need; even that big, bulbous plug didn't seem to satisfy me these days.

"Yes, Mommy?" I said sweetly.

"Mommy needs a blowjob," she mumbled sleepily.

She loved to wake up to my warm mouth wrapped around her big cock - amongst other things.

"Yes, Mommy," I answered obediently.

I sat up and threw the covers off, my pink night dress had bunched up over my loaded pampers which wasn't an issue for me, I usually pulled it up around my hips anyway so Mommy could play with my plug while I sucked her. Plus, as she always said, "a sissy should always have her ass up."

I shifted and rolled between her legs, careful not to disturb her before I lifted the covers to find that gorgeous, black cock waiting for me in all it's veiny glory.

"Sissy Breakfast," I giggled as I gripped it's wide base and pulled it into my mouth tenderly. I loved this cock, it was after all my first but, as I lay there, kissing and licking that ebony warrior, I was craving her new one; she had recently bought a larger version which also included a mechanism that would actually pump edible, cum-flavored lube. She called it "Sissy Breaker", a twelve inch, black mammoth of a toy and Mommy loved flooding my ass with that warm, delicious treat. She had really loved "blowing her load" in my face or in my mouth, laughing as my eyes went wide and my throat filled with the artificial cream. While I had yet to try for myself, Alli insisted it tastes just like the real Mccoy.

"Mommy?" I asked, between playful sucks on her rubber dick.

"Yes, Sissy?" she responded hazily.

"I want cum," I said matter-of-factly before her hand went to my head and pressed, my mouth forced to take as much of the thick shaft into my throat before I gagged.

She held me there for a moment, my eyes watering, my mouth drooling around the black phallus, "later, Sweetie, just suck it. I'll give you cum in a bit."

Alli slowly came to life while my mouth worked her cock. She started to move her hips, humping my throat with that wonderful black cock, her hand glued to the back of my head as she worked my throat muscles; we're always working my gag reflex and I can proudly say, I can take more and more. I just wished she could fill my tummy with her delicious seed but that didn't stop me from giving her my best efforts. I loved our sex life, I loved the role reversal, I loved the lingerie and girl-clothes, I loved when she whispered in my ear when we're out in public and she leans in close and tells me how hard she's going to pound my boi pussy; I've even started to love the diapers which had initially started my descent into my new Sissy Life, now I just saw those padded pullups as underwear.

Alli watched me, sleep in her eyes and an expression of indifference as I teased and kissed her mushroom tip. My lips and tongue pulled her into my mouth where I sucked that fat head and lapped my tongue up and down it's length.

"Good, Girl," she said before clearing her throat. "You love sucking Mommy's cock, don't you, Darling?"

I giggled and swallowed her as far as I could. I stretched the muscles in my throat with her girth.

I felt her shifting besides me, as per usual, I was on my knees as I pleasured Mommy and with some clunky movements she positioned her foot between my legs where it found it's way to the front of my pampers and where she began to tease my useless, caged sissy-clit.

"You are soaked, Baby," she said. Her tone neither surprised nor overly concerned. Her foot pressing between my legs where my diaper hung, damp and heavy.

I refused to stop my duties as she wiggled her foot into my loaded, pink pullup, she seemed to be enjoying the fact I was utterly soaked until I felt her suddenly pull her foot away, "Sweetheart, you're leaking. That pull-up needs to go." The pressure she had applied must have forced my wet mess to leak out the elastic legging; it only happened when I had totally filled my pampers.

Alli sat up, pulling the black beast from my mouth to my disappointment; I didn't care about my stupid, wet diaper, I just wanted her cock in my mouth. My little clit throbbed against the stainless steel sheath, the strain was unbearable and my bottom was hungry for her attention. She stepped out of bed, her rubber cock swinging as she slid her robe over her shoulders.

"Come on, Baby, let's get you changed," she beckoned, her voice finally vibrant and awake. She exited the room and made her way to the bathroom; she returned with a fresh pull-up in hand.

Alli tossed the diaper on the bed and got behind me as she did frequently these days. With a careful tug she slid the loaded nappy down my legs, the weight alone made her efforts minimal. "Lift up, Baby," she said; as I raised my knees she pulled the soggy mess off my legs where it landed on the floor with a dull "thump" sound. "Oof," she muttered, "you smell like pee."

I laughed and shook my rump at her, my plug nestled comfortably in my bottom. She gave me a firm spank before scooping up the wet diaper and walking it to the kitchen trash barrel with two fingers. She made a stop in the bathroom and returned with wipes which she used to clean my bum. I had grown to love these tender little moments, I used to be mortified but it's become kind of a playful game for both of us. With a "pop" she pulled my plug out and quickly unlocked and uncaged my shrunken little clit. She gave me another pass with the wipes, paying extra attention to my little pearls and taint, she swiped up my cheeks which were probably packed with last night's lube, before giving my delicate little hole a quick rub and wipe; I wiggled back to meet her touch and she teased me, "yes, Sissy, I know..you want Mommy to breed your little pussy."

She reached between my legs and gently gave my hairless, soft bag a squeeze; a bead of my cum formed on the pink, little tip before drooling and falling to the bedsheets.

"So cute," she smiled. "Your little clit just leaks! And those tiny little balls are the most adorable thing," she remarked approvingly.

Alli, it turns out, had been secretly feeding me estrogen and testosterone blockers which explained the growth in both my chest and behind. Not much, mind you but I did have adorable, tiny breasts now and my nipples were the cutest! Like the pink eraser nubs on a number two pencil. Alli had me on a very meticulous regiment these days; between light shaving, which wasn't much of a chore due to my light body hair which really wasn't too overgrown to begin with, as well as hygiene and getting my skin smooth with scented lotions. My bottom, apparently, was getting rounder and plump according to Mommy but just barely, I suppose I was built like this for a reason. I realize it's all so cliche, like some bad Literotica story but Alli was all I had. I wasn't from the state, my parents had passed before I was a teenager and despite a few guys from my old job, I really didn't have anyone to worry about finding out. I had taken to Alli's changes with enthusiasm, perhaps not at first but we know how it all inevitably started. She made sure to remind me constantly that I would be hers forever; I was her Sissy and she was my doting Mommy and I've never felt happier.

"Lift, Princess," she said sweetly as she wiggled my fresh pull-up up my thighs before a final tug up and over my clean tush. "Don't get comfortable, that plug and your cage are getting a rinse and going right back."

"Yes, Mommy," I said sarcastically.

She pulled my pink babydoll down before giving my padded bottom a swat. "Don't 'yes, Mommy' me, Sissy."

I made breakfast while Alli gave my cage and plug a cleaning in the sink; she was very particular about that, she was organized and very clean when it came to just about everything. Except her car, for some reason, which was loaded with tennis gear, fiber bar wrappers, empty cans of energy drinks, books and paperwork; it was the same car she had driven to college and her vehicle habits hadn't changed either. She stood against the sink, her small, firm breasts just breaching the silk fabric of her robe and when her elbows went up, her hands quickly pulling her long, blonde hair into a ponytail, they were fully exposed, the straps of her strap-on visible around her upper thighs and hips and the big, black dildo that smacked the countertop when her robe lifted with her arms.

"Today, we're going to have a great day," she said with music in her voice. She placed the freshly washed plug onto the counter.

"We always have great days when you're off, Mommy," I said as I pulled out the toast and moved back to the stove where the eggs were just about prepared.

"We do, Sweetheart but today, I'm not letting you cum until tonight, understand?" with a motion she turned off the water, placed my cage beside my plug and dried her hands on a dish towel.

I pouted.

"I promise," she began as she moved to me, her soft lips pressed against mine before heading off to the bathroom, "you will be very happy when the time comes. We can play for a bit but Mommy has an errand to run later, OK?"

"Are you dressing me up today?" I asked curiously.

"We are definitely doing that, Babygirl."

I smiled as I flipped the eggs into our plates.

It was nice to eat breakfast with Alli, so many mornings had her running out the door after a quick shower but today we laughed and joked over our eggs, toast and coffee. Our relationship really hadn't changed dramatically, that connection hadn't anyway. Sure, I was no longer working, our bedroom dynamic was entirely flipped and I was a bed wetter who needed diapers but, at our core, we never really changed.

"I'll make you a deal today," Mommy started. "Do you want to wear big girl panties tonight?" she asked with a grin.

She almost never allowed me to wear panties, mostly because she didn't want me having any accidents in her underwear but, nonetheless, her proposition remained.

"Yes!" I squealed, "I want to wear big girl panties!"

She smirked and crossed her arms on the table, "OK, well, if you can keep your pampers dry while I'm out this afternoon, when I get home, if you're dry," she put an emphasis on those last three words before she continued, "you can pick out and wear any of my panties tonight."

Challenge accepted, I thought to myself. That was certainly going to be a test; these days I didn't have much control of myself. Alli had me diapered every day for months now and while she no longer had to lock the bathroom, I had gotten ridiculously comfortable letting go in my pullups. Overly comfortable. Alli left her plate at the table and, with a wink told me to do the dishes and meet her in the bedroom for my morning pegging. My little clit tingled and l felt myself dribble into my diaper.

I finished the dishes quickly and, still in my adorable, pink babydoll and my fresh pull-up, I bit my lip, crinkled down the hall and stood at the doorway of our bedroom watching Mommy as she finished the swap-out of dildos on her strap-on. Between her legs was the "Sissy Breaker"; twelve inches of bulging veins and black cock that hung low due to it's girth and weight. The mammoth had a long tube, that Alli simply wove through the harness to keep from getting in the way of all that thrusting and spanking, which would pump edible, cum-flavored lubricant when Alli triggered the device with the palm-sized switch on the other end of the tubing; it truly was a modern marvel, one I had personally come to love. Watching her was always breathtaking, that little body, the obnoxiously large cock between her legs, the long, blonde hair and those calculating, almost predatory blue eyes. She gave the log between her legs a playful stroke when she looked up at me, "I think every woman should fuck her man like I fuck you," she said softly, "what about you, Sweetheart?"

"I don't think every man could be so lucky," I smiled.

Her eyebrows raised as she considered my answer.

"I love you, Mommy," I giggled.

"I love you too, Sweetheart," she said sincerely. "Now pull that dress up and bend over."

I squealed in delight and climbed into the bed, over the flannel sheets and began to position myself so Mommy had access to my rump but, before I could slide my pampers down or my pink babydoll up, she gave me a tender spank, "no, Baby," she said firmly, "that side."

She nodded her head to the opposite corner of the bed where I noticed the "Cherry Popper" dildo was suction cupped to the headboard, all eight inches of that wonderful, black dick hung comically over my pillow and I immediately realized what my brilliant girlfriend had planned for me this morning.

"Oh my," I gasped as I crawled over the bed.

She swatted my padded bottom, "that's right, Princess, you're getting spit roasted this morning."

On my hands and knees I crinkled and crawled to my side of the bed until the black beast clinging to the bedroom set stared back at me; I had always enjoyed sucking it when it hung between my girlfriend's legs but the thought of both of my holes being stuffed to capacity simultaneously was overwhelmingly arousing. My limp, little clit, which had been consistently caged and locked away for weeks now, actually began to show signs of life, albeit just barely. I felt that nostalgic rush of blood as it entered my recently liberated cock and while I did miss that golf ball sized plug stuffed in my bottom the unmistakable sensation of the cotton padding cradling my slow-growing bulge was pure ecstasy. If you've never had the pleasure of wearing pullups or diapers before, that security and bizarrely comforting sensation of the cotton-plastic fiber clinging around your hips and undercarriage is bliss; even the strain of one's throbbing cock against that pillow-soft, snug little diaper is simply delicious. That feeling at the tip of my boi clit as it squeezes out bead after bead of cum had my pink ass pussy begging for attention, desperate for a tongue, a finger or, preferably, my girlfriend's massive cock to explore my depths.

Alli made her way beside me on the bed. She was naked once again with the exception of the harness and that behemoth of a cock hanging lifelessly between her legs. She smiled lovingly as she watched me circle my tongue around the head of the dildo above my pillow, lapping and kissing the black cock slowly and deliberately as if I could somehow bring it to life.

"You just love sucking big dicks, don't you, Sissy?" she observed.

I looked into her eyes as I slowly throated the toy, taking as much as I could before I felt my eyes begin to water. With my lips wrapped around the veiny shaft and my semi-erect clit just leaking into my pampers, the realization of how much I loved our new bedroom roles was at the forefront of my thoughts. Before, our sex life was healthy and fun but, as my beautiful girlfriend watched me suck the big, black cock suction cupped to the frame of our bed, we had taken things to an entirely new level of pleasure, adventure and satisfaction; my orgasms, with her collection of dildos pounding my hole, had never been so intense or addictive that my cock being locked away was of zero consequence.

"I love watching you suck cock," she said dreamily.

I pulled the black beauty out of my mouth, my cheeks red with embarrassment, "I love you watching my suck cock," I replied.

"You're the perfect man," she said as she shifted and moved behind me.

"Sissy," I corrected, "I'm the perfect Sissy," I finished. I knew she would soon have that ungodly, cum-shooting black monster stuffed inside me and I ached to feel her stuff that baseball sized cock head into my nimble little fuckhole.

I went back to work on the dick in my face, dragging my tongue down it's length before playfully sucking those beautiful, black balls as Mommy spanked "Sissy Breaker" against my padded rump. I felt her searching the bedsheets for the lubricant before she returned her efforts to me; I felt my diaper being carefully pulled down my bottom and the cold wet lube on my cheeks and crack before her hands began the ritual of preparing me. Her hands groped and spanked my backside as I began bobbing on the cock in my face and then I felt it: that massive tip pressing against me, splitting my cheeks apart with it's sheer size.