Bedwetter Ch. 02

"Beg me, Slut," Mommy growled.

I felt weak in my knees. I had taken "Sissy Breaker" a handful of times now but every time had felt like the first and I knew I would be a gaping, quivering pile of limbs in no time at all. I gave one final suck before I answered her, "please, Mommy, fuck my boi pussy, I need your big, black cock inside me."

I couldn't see her face but I knew she was wearing that evil grin and suddenly I felt it, her gentle pokes at my rear became increasingly forced as she stretched my ring wide open with that enormous black beast. I squealed and collapsed into my pillow; that initial sting at my entrance, that feeling of being torn open was extremely intense but, as she slowly pressed her hips forward and my massive invader sunk further, I could do nothing more than welcome it's unmistakable presence in my ass while trying to remember to breathe.

"Good Girl," she said softly. "Does that feel good, Baby?"

I knew she wasn't even close to filling my hole but, when that initial shock faded and I could feel every inch and every vein as the slick rubber dildo slid deeper into my ass, I knew I was born to take cock.

"Yes!" I choked as I clinched the bedsheets in my white knuckled fist.

"Your ass is so fucking sexy, Baby," she cooed, sinking her massive cock deeper inside of me, "I love watching my huge cock disappearing into your cute little boi pussy."

The pressure was almost unbearable but, with my face in my pillow, I did my very best to relax and enjoy the ride.

"Almost there, Sweetie," she comforted.

"Yes, Mommy," I cried. My clit had gone totally limp again, cum leaking steadily into my pull-ups; thanks to my cage, my adorable little clit was constantly dribbling cum whenever I was aroused, an endless stream of it was now forming a slick mess in the front of my pampers but when she finally managed to stuff all twelve inches inside of me and I could feel her smooth thighs against my own, I must have shot a bottlecap's worth of milky seed into the cotton pad between my legs.

I squealed as she bottomed out in my ass. There was twelve solid inches lodged in my rear but it felt like thirty. My ring was stretched beyond capacity and my magic button deep inside was in convulsions. Spasms of euphoria went through my body as Mommy let my poor hole adjust to the ridiculously large cock buried between my cheeks.

"It's so big, Mommy!" I cried.

"I know, Sweetheart, you're doing such a good job!" she encouraged. "Mommy is going to pump her little slut full of cum. Would you like that, Honey?"

The thought of her breeding me was delightful. The first time she flooded my ass with that delicious, artificial load was heaven on earth; that sudden explosion deep inside was my definition of satisfaction.

"Yes, Mommy, breed my hole," I whimpered.

"I will, Princess but I need you to suck that big, black cock for me first, OK?" she said sweetly.

"Yes, Mommy."

As Alli began to pull out of me, a slow and methodical procedure, I managed to get up on my elbows. Those first few thrusts with "Sissy Breaker" were truly intense but I knew from experience that she would soon be pounding me with that horse cock and if I wanted to feel her flood my pussy with cum I would need to earn it and that's what I intended to do.

"Look at that pretty, gaping hole," she said approvingly as she finally pulled out of me. I could feel it, my tiny little ring, now stretched wide and open, pulsing and vibrating from the beating Mommy had just laid on it but I knew she was far from finished with me and I had a cock in my face that desperately needed my mouth wrapped around it.

As I took it in my mouth I felt my shrinking boi pussy widen once again as Mommy re-entered me. My eyes widened as I held the black rubber dildo in my lips, I felt "Sissy Breaker" drive right back up my ass, filling me with one, deliberate thrust. I gasped, my tingling clit shot another squirt of cum into my diaper, my lips struggling to keep their tender grip around the shaft of the cock in my face.

She pulled out slowly again but, this time, she stopped before that big, bulbous head came popping out and, with another deep thrust, rammed it back inside me; as she continued to pick up speed I found my lips and tongue working at her pace, sucking while Mommy pounded my bottom, with each deep thrust of the giant sending shockwaves of pleasure throughout my soft body while my pampers grew sticky and wet.

"I love fucking your ass," she grunted as she thrusted and pulled, delivering punishing blows to my packed bottom. My attempts to speak were in vein as my breathing became strained and I gagged on the phallus now stuffed throat.

"Are you ready, Baby?" she asked coyly, she loved the little slut she had created; a once proud man transformed into a needy, cock sucking bitch who never hesitated to bend over and take whatever massive dick she could attach to her strap-on. I had become a total sissy and, for both of us, it had never felt more right.

"Yes, Mommy!" I cried as she buried those twelve inches between my cheeks. I loved it, my little blonde girlfriend fucking me like a whore, the loving tone of her voice when she humiliated and teased me, the role reversal and the submission but, most of all, it was the feeling of being absolutely stuffed full of dick and as I felt the approaching sissygasm in my diaper, with my lips wrapped around another cock I couldn't wait to feel her pump me full of cum.

"Are you going to cum in your pampers, Baby?" she teased; she slowed her rhythm and focused her thrusts, long deep and hard while I pressed myself back to meet her thrusts.

I pulled my mouth off the rubber cock, "yes, Mommy! I'm going to cum in my pampers!"

"Good Girl," she said under labored breath.

The tingle grew to an unbearable pressure in my limp little cock and I knew I was going to explode. I whimpered and absorbed her pounding, her body crashing into my own and then, it happened. I felt it, she hit the switch, slammed the beast deep and my hole filled with that amazing, warm liquid as I felt myself release into my soaked diaper; squirt after mind-numbing squirt as I bellowed, moaned and collapsed once again into my pillow.

Alli gave my ass a spank before unceremoniously slipping the black dick out of my exhausted hole. She spread me open with her hands and giggled as she admired her handiwork, my gaping pussy began to leak her massive load.

"So fucking hot," she said enthusiastically, "I need to film this."

She quickly moved to the nightstand where she retrieved her cellphone as I lay there, face in the pillow, ass in the air. She giggled as she filmed, I could feel her seed running down my taint and pooling in my mess in the cotton webbing of my sticky pullups. She watched every drop dribble from my stretched ring and disappear into the nappy occasionally spreading me open to ensure I was done leaking before tugging my pull-up over my abused rear and crawling up the bed where she kissed me and told me how amazing I was.

"I love you, Baby," she said. "Now let's take a shower."

From the outside looking in, one might think I had gone too far with all of this; I mean, how many men would tolerate a finger in the ass let alone the bed wetting, diapers and having their girlfriend dress them like a porn star before making him bend over and having a fat, black, jelly dildo stuffed in his ass? I suppose it boils down to personal preference but, unlike so many dirty stories and sissy pipe dreams, Alli and I were still very much a couple and, in the shower that day, we laughed and teased one another under the hot water. We washed one another and held each other; I loved kissing those soft, pink lips about as much as I loved taking her cock. While I was no longer the "man" in our relationship, Alli loved when I kissed those soft breasts and teased those beautiful little nipples and, these days, with my own budding chest, she would tease and lick my own which sent those wonderful little shivers through me, like a jolt of electricity. She took great joy in making me squirm, as the steaming water ran down my hairless, soft skin, she would turn me around, pressing her perfect breasts into my back, reaching around me and, with a handful of scented bodywash, stroke my little cock; slowly tugging my tip in a downward motion before massaging my smooth little coinpurse and using her fingers to rub my taint. I loved it, she never jerked me like she had before but rather pressed or rubbed or simply teased and tugged my little clit like I was another girl and I, in turn, would lick her beautiful little slot. She tasted like strawberries and when she came in my mouth she would shake and quiver while forcing my face and tongue deeper inside her.

We laid in bed for a while, Alli had plugged me, caged me and put me in a fresh pull-up; she was shocked how much cum I had pumped into the last one. We watched an old horror movie from the seventies, the kind with rivers of watered down ketchup, bad effects and even worse acting before I made us a couple sandwiches; I did all the cooking these days but it certainly wasn't some domination roleplaying, Alli was a horrendous cook.

"You ready to play dress up with Mommy, Sweetheart?" she asked as she swallowed the last bite of her turkey sandwich.

"Yes! I want to wear pink today!" I giggled.

"You're such an adorable little Sissy Girl, aren't you? I was thinking we could put you in the black dress I got for you," she said in her motherly voice before taking a big gulp from one of her favorite energy drinks.

"Ooo," I had forgotten about that dress. "And the thigh highs?"

"Yes, Princess. We're going to do your hair and makeup too. I want you dolled up when I get home later," she beamed.

"Special occasion?" I asked. She had taught me how to use makeup a handful of times but those were rare; Alli didn't wear tons of makeup, usually she just wore a little mascara and eyeliner unless it was a special evening.

"Tonight you're in for a real pounding, Girly."

We tried a number of adorable little outfits that day; the black dress she purchased for me didn't fit quite right on me so we raided Alli's closet before, ultimately, she decided to put me in the cutest pleated skirt from her college days. It was a light pink, black and white pattern that just looked perfect on me; my little pink pampers just hidden by it's length although, when I bent over even slightly my diaper could not be missed. She put me in a cute white, lace bra that was a little on the snug side but my little breasts looked spectacular and when we added a white, button up shirt that she tied up in a knot above my navel and black thigh highs, the look was just about complete.

Alli added a pair of black heels, a few little accessories including a gold, heart necklace which hung right between my tiny breasts and then she gave me a healthy dousing of pink lilac body spray. Once I was dressed she brought me to the bathroom where she managed to get my short, blonde hair into pigtails; they weren't very long at all but, I had to say, I loved it. Alli say me down on the toilet and started on my makeup; she started with foundation which made my less than perfect skin glow before doing my eyebrows, adding black eyeshadow, eyeliner and mascara before she added the final touch: bubblegum pink lip gloss.

"You can keep this, Baby," she said, handing me the small tube, "in fact, now that I'm looking at you, we're going to have to get you your own stuff."

When she had finished and I clumsily stepped to the mirror, I gasped. Alli had done me up before but, for one reason or another, she hadn't given me the "works" like she had tonight. She wasn't always as enthusiastic about doing my makeup and, often enough, she never did anything with my hair but tonight I was the complete package.

"Oh my God," I whispered.

Alli watched me with a smile as I admired my reflection. I wasn't a super masculine man by any means but with the hair, the makeup and the outfit, honestly, I could pass for a girl easily and that realization had me overwhelmed with possibilities.

"You like?" she said wrapping her arms around me and nuzzling my neck with her nose and lips.

"Baby, I love it!" I was overcome with emotions, I never gave my appearance a lot of thought; sure, I suppose I wanted to look cute but I had never felt impressed when I looked in the mirror, I just looked like a boy in a dress but this was something else entirely and I just couldn't believe the cute girl in the mirror was me.

"I do too, my Love," Alli gushed, "you're such a pretty girl!" she giggled as she made a quick adjustment to my hair.

"Will you take me out some night?" I turned to her and gave her a hug.

"Soon, Sweetheart. Now, all you have to do is keep that diaper dry. Can you do that, Baby? I'll even let you use the toilet if you have to go. I know you want to wear my panties tonight."

I hadn't used a toilet in almost two months. Don't get me wrong, I still had most of my bladder under control but I was getting used to just letting go in my pampers and, on more than one occasion I hadn't even thought about it, it just kind of happened. I wanted to wear panties though, they would look so cute with this outfit and I had one specific pair in mind.

"I think so, Mommy," I bit my lip, "I was getting used to my pullups but I think I can do it."

She kissed me on the cheek, careful not to press top hard in fear of smearing my makeup. "You can do it, Princess."

It was mid-afternoon by this point and Alli had some errands to run, she said it was work related and left it at that and we didn't have the kind of relationship where we questioned one another. She looked amazing, I couldn't help but compare my body to hers; the shape of her legs, her slim body, her heart shaped bum and fit thighs in her black jeans. Her little breasts were barely visible in the big, gray sweater she wore, her long blonde hair tied back in a ponytail and, on her feet, a cute pair of heeled combat boots, shiny and black. It was nice-casual, a look that fit Alli perfectly; she could wear whatever she wanted, she was a size one and looked amazing in anything but she had a darker pallette with grays and blacks and, on occasion, the random, old, beat up heavy metal band shirt.

"I'm all dressed up with nowhere to go," I said sitting on the bed flipping through movies.

Alli had been slowly putting things away and rummaging through the room getting herself ready to head out. She finally grabbed her little military bag, the size of a small purse, an olive canvas first aid bag she used as a handbag on her days off. She sighed in deep thought before looking up at me in my little skirt, pigtails and heels and immediately smiled down at me. "You are so cute, Baby!"

I bit my lip and grinned, "I love you."

"Love you too, Princess," she said as she leaned down to kiss my pink lips. "Keep that diaper dry."

"I will, Mommy," I said sheepishly.

"You're getting such a pounding when I get home," she whispered in my ear before giving it a playful nibble. My pink ring gripped the jeweled plug in my ass and I felt that familiar sensation in my pullups when my caged clit began to drool.

"I'll be back soon, Baby." With that she turned and headed down the hall before I heard the obnoxious storm door bang open and the front door close with a moderate slam.

I must have dozed off for a bit; I had found an old horror movie from the thirties and closed my eyes but I hadn't anticipated actually falling asleep. When I opened my eyes I couldn't help but look down at my body. I was in love with the skirt and how it made my smooth thighs look, especially with the black thigh highs; and the heels were hot, black leather with what I assumed to be three inch heels. I clicked them together like Dorothy in the Wizard of Oz when I heard that unmistakable sound of the storm door. My clit twitched in my cage knowing Alli had big plans for me tonight. There was a pause before I heard Alli's footsteps coming down the hall. When she appeared she wore a wicked grin and I just knew tonight would be special.

"Are you dry, Baby?" she asked, leaning into the bedroom.

I nodded, "yes, I think so. I kind of fell asleep."

There was a look of concern on her face and she stepped into the room and to the bed, "up, Sweetheart. Let me check you."

I slowly sat up and got to my knees. Alli leaned over the bed, raised my skirt and, with her free hand, patted the front of my pampers; when she was satisfied with her inspection of the front she promptly checked my bum. She gave a quick pat and then gave the crinkling diaper a squeeze between her thumb. She wasn't quite satisfied; with a simple movement she bent me over and pulled the back of the gauze waistband.

"Did I go?" I asked meekly.

"A tiny bit but you did fall asleep," she said, more to herself than me.

She released the back of the pull-up and flipped my skirt down. She sat back on her knees and twisted her lips in her own thoughts.

"Ok," she started as she stood from the bed, "pick out a pair and meet me in the living room," she said.

"Are you sure?" I asked a bit self consciously.

She leaned over the bed and kissed my wet, pink lips, "yes, Babygirl." She paused. "And touch up your lips, Ok?"

"Yes, Mommy," I said proudly.

The heels were hard on my ankles and I'm not proud to say my feet have kind of collapsed but I'd be lying if I said I was a natural. I carefully stepped off the bed and immediately sat down. I pulled the pullups down my thighs until they softly hit the floor. I stepped out and clip-clopped my way to Alli's underwear drawer, it was a wonder I had never investigated before but I suppose, until now, I never had a need to because of the pampers. I immediately started looking for a pair I had seen on Alli, a tiny white lace thong that I just know would contain my little pearls and clit without issue. So many options, pink and black, flower patterns and cotton but I finally found what I was looking for.

I carefully stepped into the miniscule thong, knelt down and slipped them on. Incredible. I slipped my tiny, caged package into the tiny triangle of white lace which was even smaller than I had thought but still manageable; it was definitely a possibility for my stainless steel cage to suddenly spill out but that thin fabric between my cheeks and, especially, right up against my pink hole, was just too incredible to even consider another pair. I flipped my skirt up to inspect before fixing myself and, finally, after applying more lip gloss I made my way down the hall, clicking my way awkwardly until I stepped into the living room where I found Alli. And a large, black man sitting on my couch.

"There he is," Alli said gleefully.

I don't think I was capable of looking more surprised. My eyes wide, my mouth slightly open and a total absence of words.

"Honey, didn't I tell you we were having company tonight?" she said watching me with a pleased grin.

It was a moment before I snapped out of it; I had no idea on earth who this man was and the realization that he was the only one other than Alli to see me like this had my head spinning with a flurry of nervous anxiety and total bewilderment. "Yes, that's right, you just never mentioned who," I did my best to act casually. As I stood there looking like a Sissy doing her best slutty schoolgirl look.

"This is Ben," she said with a raised eyebrow, smiling with her eyes. "He's from work, Sweetie."

We awkwardly greeted one another before Alli slid over in the couch to make space for me to sit between the both of them.

"Sit, Baby," she said reassuringly.

While it was awkward at first I never had issues talking to people. We broke the ice, Alli left is for a moment to get us all a glass of wine and not long after I was comfortable. Ben seemed like a sweet guy, he was soft spoken, smart as a whip and, with his broad shoulders, big arms and hands, a handsome guy. We talked about Alli, we chatted about movies and music and just had a lovely conversation while Alli sat quietly drinking her wine. My first glass went down quickly and my second had me with a pleasant buzz; I couldn't help but notice how wonderful Ben smelled, his cologne, his musk that just reminded me of men. I couldn't help but admire that dark skin and the size of his arms but, for some reason, his hands were always drawing my attention. I had long, slender digits and not a hair in sight but Ben's hand was like a baseball glove and his dark hair covered his knuckles and forearms.