The Boss’ Baby - Part 14 Desperation

1...2...3…

Jesus, how many times did they do it last night?! I contemplated sorrowfully as I squeezed the contents of the 4th used condom into the tiny bowl.

It had been a week since the dinner that officially turned my life upside down. Where I was forced to watch as my Boss pounded my wife into oblivion. He had been staying over—and sleeping in my marital bed—ever since.

I discarded the remnants of the 4th condom and added it to the pile on the tray of the new high chair I was sitting in. Apparently, in addition to being muscular, athletic, and the Boss of a successful company, Charles was also a carpenter on the side. He took the liberty of building a large, oversized high chair for me to eat all of my ‘meals’ at home in. Anything to further emasculate me in my wife Amy’s eyes. Apparently it was working too, because Amy deemed it necessary that the highchair be painted a bright pink and stamped with flowers.

My meals consisted of mostly pureed foods. I had forgotten what it was like to chew. But my morning breakfast always consisted of the previous night’s ‘leftovers’ from Charles’ escapades with my wife.

“Is your breakfast ready sweetheart?” Amy asked cheerfully as she sipped her morning coffee in nothing but a bathrobe. She didn’t even bother tying it closed, knowing the hint of her nakedness only helped to drive me crazy inside my chastity cage.

“Yes Mommy...” I said dejectedly. She had insisted on me calling her that permanently. Calling her ‘honey’ or even ‘Amy’ was strictly forbidden now.

“Oh! Almost forgot!” She said, reaching between her legs and pulling another used condom from her vagina. “I was keeping this one warm for you!!” She beamed, placing it on the tray.

Charles chuckled behind the newspaper at the table in front of me. Not even sparing me a glance as he flipped the page.

I whimpered as I picked up the 5th rubber sack of jizz, noticing it was knotted. I looked up at Amy, smiling at me expectantly. I knew I had to get the splooge in the bowl, and the only way for me to open the condom was to break it open with my teeth.

I could taste her juices as I bit at the bulbous tip. After a few unsuccessful chews, the reservoir finally popped open. Squirting some of the penis juice out the side of my mouth and down my chin before I could aim it into the almost full bowl.

“Oops! Wooks like the wittle baby needs her bib!” Amy exclaimed in her patronizing Mommy voice.

She reached behind the high chair and pulled out a large, pink bib that read “Little Princess” in big, feminine writing. After she clasped it around my neck she used it to dab the sticky jizz dribbling down my chin and redirect it back to my mouth.

Amy had always despised cum. Never letting me finish in her mouth back when she was giving me blowjobs, even stopping as soon as there was the first hint of pre-cum. So I knew how disgusted she was to handle all of this thick, sticky Charles-spunk. But she had no problem with grabbing a tiny baby spoon, and scooping a gooey helping to feed to me.

“Open up baby!!” She cooed, “here cummmsss the airpwane!!!”

After shovelling every last spoonful of disgusting, salty baby-batter into my mouth, and making sure to catch and refeed every last drop that seeped out the sides, she plopped the spoon down into the empty bowl and reached under the tray between my legs. Pinching my diapered crotch.

“Awww! Someone is SUPER soggy this morning!” She giggled. Poking my saturated pink princess pampers.

“Why don’t you go get your morning spankies from Daddy, then come upstairs and Mommy will change your diaper and get you ready for work!” She smiled. Pinching me playfully on the cheek like I were an infant. Unlocking the tray, and helping me off the chair as if I needed it.

It was hard to decide what had become my least favorite part of my day since my new routine started, but this was definitely up there. Getting down on my hands and knees, and crawling over to the man now fucking my wife, sitting up so that my saggy diaper drooped to the floor and having to say: “Daddy, can i please have my spankies now?” In a pathetic, high-pitched, sissy baby voice.

Charles glanced up from his paper as if noticing me for the first time. He sighed, chuckled, sipped his coffee, then pushed his chair back, already unbuckling his belt.

“You know what to do.” He said firmly as he stood up and pulled his belt through his loops.

I whimpered softly as I bent over the dining table.

The same way I did one week ago when Charles pelted me right in front of my wife. Apparently she had enjoyed it so much she decided to make it a daily thing. She carefully pulled my floppy, drenched diaper down around my calves. I stayed stock still. Last time I flinched too hard and broke the tapes, I got extra swats for it.

I could hear the wind whistle as Charles reared back and snapped the belt across my bare cheeks with a THWACK!

I bit down on my thumb to keep from squealing as the assault began. Amy stayed and watched lash after lash until I was in tears. She rubbed my head softly as if I were nothing more than a disobedient pet receiving its punishment, then gave Charles a long, passionate kiss before heading upstairs. Knowing she’d still be able to hear my squeals from the bedroom.

After my ass and thighs were painted red, Charles tossed the belt on the table and sat down to catch his breath. My only mercy being that he didn’t want to get all sweaty in his suit before work. I sniffled and dabbed my damp eyes, knowing it was appropriate for me to stand up and carefully pull my cold, wet diaper over my flaming hot asscheeks.

“Before you go...” Charles said as I made to go upstairs, “why don’t you take care of something for me.” He reached under the table and unzipped his zipper.

Really? I wanted to say. Now? Have you not cum enough in the past 12 hours?!

But it wasn’t about cumming for him. People in power are in power because they crave it so. They relish any opportunity they can to establish dominance over those they’re superior to. That’s what they get off on.

I thought of how much my life would be different if I was one of those types. An alpha, a power-hungry, dominant, aggressive man that took what he wanted. But instead, I had to take his dick in my mouth, under the table, while he read the paper and finished his breakfast.

“You know...” he said nonchalantly, “your wife sucks better dick than you.”

******

It had been almost a whole month since I'd cum. I was becoming desperate.

Almost all of my daily thoughts centered around something sexual and perverted. And, to my chagrin, my brain often defaulted to the sexual encounters of my wife and Charles.

She had come up to the office almost every day before lunch. Spending an hour or so inside, behind locked doors, while I was forced to wait at my cubicle and imagine what they were doing. At lunch time, Amy would come out, hair disheveled, face flushed, carrying tupperware of whatever pureed slop she had for me that day, then hand me a used condom to frost my lunch with. After spoonfeeding the cummy mush to me, she’d pinch me on the cheek, check my diaper (but never change it) and then head back home.

Because Charles was getting sex regularly, he rarely needed me to please him anymore. Which meant he hadn’t fucked my ass in over a week. I hated how much I was starting to miss it. To crave it. Anything to help release the building pressure in my balls and prostate as I leaked from a good pounding.

I had tried using my fingers. Lubing them up with my saliva and sneaking them into my diaper at my desk or at home in the closet during times I was supposed to be cleaning in my french maid outfit. All it did was make me even hornier.

I remembered seeing in my sissy porn (the same one that landed me in this situation in the first place) that certain girls could achieve what was called a “sissygasm”. Which was where they were able to cum from anal stimulation of their prostate only. I decided to try it using a cucumber. I would have used the big black dildo Amy had bought when she was fantasizing about Charles, but it was tucked away in their room. My room. Or what used to be ours.

I used a little Crisco as lube and hid away in the closet to pound myself with the cucumber. After 20 minutes of shoving it in and out of my hole, I was unsuccessful at achieving anything but a small bit of leakage. When I came out of the closet, Amy and Charles were waiting for me. Arms crossed.

Charles proceeded to blister my ass while Amy shoved the cucumber in my mouth and forced me to eat the entire thing.

I decided my only hope was to find someone around the office to bang me. It made me feel like such a thirsty slut to be hunting for dick to fuck me in my ass.

Obviously if Charles wouldn’t fuck me, my next hope would have to be Dave from IT.

******

I made my way down the hall to his office. It was tucked away in a pretty private corner of the floor. So it was unlikely anyone would hear us moaning.

I knocked on the door. I could hear a rustling and scampering. “Just a minute!” Came his voice.

The blinds of his window creaked open. When he realized it was me, he heaved a sigh.

The door opened. I walked in, but he didn’t even say ‘hi’ or even acknowledge me. Just hurried back to his desk and back in his chair. The screen of his computer illuminating a big, white, rubber dildo sticking straight up off his desk.

“Sorry about that, sir!” He said in a high-pitched voice. But he wasn’t talking to me. He was talking to his screen.

“That’s ok, slut!” Came a gruff voice from the monitor. “Now get that dick back in your mouth!”

“Yes sir!!” Dave squeaked. And started jamming the head of the 8 inch rubber cock into his mouth.

“There’s a good, slut!!” Said the voice, “suck it good! Daddy’s gonna cum soon!”

I moved to the side of Dave’s desk and saw a window on the screen with some big, fat, naked white guy stroking his cock. It took me a second to realize this was who Dave was talking to.

Dave’s eyes were on me while he bobbed up and down on the fake cock while the strange man stroked harder on the screen. “Ohhh yeaaaa! I’m gonna cum from watching you, you little faggot!!” He said.

“What the fuck is this?” I whispered quietly. But apparently it wasn’t quiet enough.

The man on the screen stopped. “Is someone there?!” He asked.

Dave stopped sucking. Glanced at me, then back at the screen as he pulled the cock from his mouth.

“No no it’s just—“ Dave tried to say, but the video feed clicked off, and the fat white guy was replaced with a black screen that read ‘Connection Lost’.

“God DAMN IT!” Dave yelled. Smacking his desk so hard that the dildo swayed back and forth.

“What the fuck, Tom?! That was one of my most important clients!! And he was about to cum!! Now he may never come back!!”

He looked like he was about to cry.

I didn’t know what to say. “I...i’m sorry i...i didn’t know what...”

“What the fuck do you want anyway?!” He asked. Obviously frazzled and frustrated by whatever was going on.

“Well i was hoping that ummm...” but it all sounded so stupid now. Maybe it sounded stupid before?

“You see...i haven’t cum in a while, and i was hoping you could umm...”

“What? You want me to make you cum too?” He asked. Suddenly perking up like a hobo offered crack. “Whatta ya want? A blowjob? I’ve gotten pretty good! I’ll just have to video it if you don’t mind...”

“Well uh...i don’t think that’d work, see...on account of…i’m in chastity and all...” I said, tapping my diapered crotch so that the hard metal could be heard above the crinkle. “So i was hoping maybe you could...fuck my ass instead?”

It was one of the weirdest conversations I'd had in my life. Dave studied me for a second, then laughed.

“Sorry bud...” he said, “but I'm in the same boat.”

He stood up and undid his belt buckle. Dropping his pants down and showing his big, pink, princess diaper. He shuffled forward and peeked the front of his diaper open, allowing me to look inside and see his 7 inch dick tucked tightly in a cage only slightly bigger than mine.

“Stephanie locked me in it after that awful date we had where I molested her.” He said, his voice cracking a bit. “She said the only way for me to get unlocked was to make 30 guys cum.” He wiped away a tear, “i have to show her video evidence of every fucking person i get to jack off for me. Turns out it’s a lot harder than you’d think. I’m only at 18 so far. And you just ruined my chance at 19.”

I didn’t know what to say. All this time Dave had been fighting the same problems I was facing. Well, minus the whole boss-fucking-your-wife thing.

“Well...do you mind if maybe I borrow that dildo for a bit?” I asked sheepishly.

“What? So you can fuck your own ass with it and give it back for me to suck on?!” He asked incredulously. “I don’t think so buddy! You’re gonna have to find dick somewhere else...and I wouldn't recommend the internet or chatrooms...”

******

On my way back down the hall to my cubicle, I passed by a coworker named Brian. I stopped for a second, thought about it, sighed, turned and said: “Hey Brian...”

He did a double-take. Probably wondering why I was speaking to him for maybe the third time in three years. He raised his eyebrows, perplexed.

“Uhh...” I stammered, “You’re gay right?” I asked. Immediately regretting the brashness of my question.

Again he looked confused, but nodded. “Yea...”

“Well...i was just thinking...” I said, sweating, “maybe you and I could....meet in the bathroom some time...” I cringed at my pathetic attempt to proposition him. I hoped he didn’t find it as crude as it felt.

But he did.

“So let me get this straight...” he said after a long while. Stroking his beard and looking at me quizzically. “You think because i’m a gay man, i’m willing to just have sex with any guy that invites me on the wonderful prospect of ‘meeting them in the bathroom’ —of all places??”

He looked like he was about to hit me. Clenching and unclenching his fist. Breathing hard. I squinted and waited for the blow to come. But it never did.

When I peeked one eye open, he was gone.

“Someone’s getting a little horny aren’t they?” said a voice behind me. I turned to see Stephanie, the secretary, smiling wickedly at me.

“I...i...”

“Save it.” She said, “If you really want to be a little slut and beg for cock around the office, I have the perfect prospect for you.”

I hated how pathetic it was that a beautiful woman like her was helping me find dick to satisfy me. Like I was some kind of crackhead desperate for a fix.

“You know Steve, over in Accounting?” She asked.

I shook my head, hoping I wasn’t thinking of the big, fat, balding guy that was always dripping sweat every time he walked over to the water cooler.

“He’s the big, fat, balding guy that’s always dripping sweat every time he walks over to the water cooler.” She said as if reading my thoughts. “He’s also a virgin.” She said with a wink before walking off. Probably headed towards Dave’s office to check on his progress of making 30 men cum.

******

Steve’s cubicle was not exactly as secluded as I would have liked it to have been. But I was too horny to care.

I tapped on the plaster next to the gap that represented his doorway.

“Hey there, Steve is it?” I said. Trying to sound casual.

Steve’s chair screeched under his weight as he turned around.

“Yes?” He said gruffly. His multiple chins furrowing as he tried to decipher who I was and why I was there.

“I’ve got a proposition for you...” I said, hoping I sounded like one of those smooth guys who pick up chicks.

“What is it?” He asked impatiently, wiping the spittle from the side of his mouth and dabbing the sweat from his forehead with the back of his hand.

“Well, I'm just gonna come right out and say it, Steve: word on the street is...you might be a virgin...is that true?” I said. Casually playing with a pen I'd found on his desk.

“Uh...” Steve’s suspicious nature switched to that of mild embarrassment, followed by feigned fortitude, “I guess that is technically true...”

“Well I think I can help you with that, Steve...” I said, trying to sound confident.

He shifted in his chair, which groaned like a banshee under his massive weight. His shirt coming untucked from his wide hanging belly and already saturated with pit stains. I tried to hide my disgust.

“Oh yea?” He asked, chuckling awkwardly. Trying to downplay how excited he was getting. “You got a girl lined up for me?”

“Not exactly, Steve...” I said, continuing to fidget with the pen, “you see, there are other...avenues...you can take. Maybe from someone’s...backdoor...instead.” I said, Hoping he caught my drift.

“I don’t follow.” He said.

I reached out and covered his hairy hand with mine. Trying to sound like one of those thirsty girls at the bar. “I’m talking about me, Steve.”

He snatched his hand away as if I'd burned him.

“Uh...sorry...” he stammered, “I...i’m not into guys. I’m into girls!!!” He exclaimed. As if trying to convince a crowd that wasn’t there.

“But are girls into you?” I asked.

******

30 minutes later the door to the broom closet opened. I honestly didn’t think he’d show up. But there he was.

“Alright...” he said as he closed the door, looking around nervously. “Let’s get this over with...”

He tried to act nonchalant and confident, but I could tell he was actually nervous, and sweating even more than usual.

I smiled and walked up to him, wondering if I should kiss him or something to make this more romantic. Then I realized I'd never kissed a guy before and how weird that would be… so I just got down on my knees to suck his dick instead.

After unbuckling his pants and dropping the massive amount of fabric to the floor, I expected his dick to be ready and poking me in the face. But even with his pants down, I couldn’t see it at all from my vantage point. It was hiding under his flab. He graciously lifted up his tummy as his breathing quickened in anticipation.

Underneath his folds and a forest of unkempt pubic hair was a tiny nub about 3-and-a-half inches long. It was purple and dripping already. I cringed as I closed my eyes, amazed at how far i’d fallen. How low I'd go just to get what I needed. I took his tiny dick into my mouth, feeling like I was sucking on my thumb as my diaper crinkled beneath my slacks.

The goal was to get him lubed up so he could get it in my ass. Though I doubted he needed much to fit into my hole. Unfortunately, after only two sucks with my mouth, he was already cumming.

“Mmmphh!!” I said with his prick still in my mouth. Taking all the cum and swallowing it out of habit. “What the fuck was that?!” I barked after I gulped it down. “You came already?!”

“S-sorry i...” Steve said, turning a deep shade of purple. “J-just keep going...i can get hard again...” he said, sounding more and more pathetic.

I sighed. Wanting to storm out and be on my way. But I was so desperate. So I kept sucking.

Slurping his tiny cock that was now shriveling up to less than an inch.

Finally, after about 10 minutes of licking and sucking his salty balls, his cock started to stiffen. I didn’t waste any more time lubing it up. Just stood up, turned around, and started pulling down my pants with renewed vigor.

“What the fuck is that?!” He asked after seeing my soaking wet diaper that I carefully pulled down.

“Don’t worry about it. Just shut the fuck up and let’s get this over with...” I said, bending over and spreading my asscheeks for him.

He seemed very reluctant. I guess the shock value of it all was finally hitting him. But I didn't give him time to hesitate as I backed my ass up into him, and he snapped out of his reverie to stuff his cock into my hungry hole.

It felt good to have something in there, but I was immediately disappointed by how little he was able to fill me. I’d grown accustomed to having Charles’ python snake its way through my intestines, but Steve’s tiny member left me feeling like I was just getting fingered.

Regardless, I was going to make the best of it. I slowly started building a rhythm, and was surprised how good it was starting to feel as Steve managed to hit my spot. He was helpless, his inexperience showing. I was like the sluttly cheerleader having to show him the ropes.

“There...right there...yes! YES!” I moaned, “oh god! I’m actually close! Please don’t cum yet!”

But just like all those times with me and Amy when she would say the same thing, I felt a warmth start filling my insides. Steve had cum. And I didn't get my orgasm.

“S-sorry...” he said.

******

“So how was your day, baby?” Amy asked as she turned the water off to the tub. She had insisted on bathing me lately. Saying it helps to make me feel like a ‘helpless baby’.

She was absolutely right.

“It was fine...” I said, attempting to entertain myself with a rubber ducky and a toy boat.

I tried not to get turned on as she started rubbing me down with a sudsy loofah. But I was trapped in a constant state of arousal.

“Maybe we should take this off so we can get it clean?” She said, tapping my caged cock. “With how messy your diaper was earlier, there’s probably all kinds of bacteria in there now...”

My heart leaped. Was she finally going to let me cum?! I couldn’t contain my excitement as she pulled the tiny key off of her necklace and slid it into the lock. I felt like a prisoner getting their chains broken as she slid the tubing off, allowing my dick to breathe.

“Now don’t get too excited...” she said as she noticed my instant erection. “You won’t be cumming in the tub today...”

My mind was moving a million miles a minute dissecting her every word. So I won't be cumming in the tub, or I won't be cumming today...? I thought.

I tried to control myself as she sensually rubbed my entire body down with the loofah.

After she drained the water and had me stand up so she could dry me off with a pink unicorn towel, she still hadn’t put my cage back on. She stood up off of the toilet she was sitting on while bathing me, and I couldn’t help but stare longingly at that too.

When was the last time I’d used one of those?! I thought, genuinely unable to remember being able to do something so simple as pee in a toilet and flush it all away without having to wear my warmth around for the next few hours.

“Awww!” Amy cooed, following my gaze, “somewon misses the big girl potty don’t they?!”

I nodded and sniffled.

“Awww...well...why don’t you get in front of it...” she said.

Again my heart leaped. Was I really gonna get to cum and use the potty on the same day? How lucky was I?! I thought as I scurried over in front of it. Feeling like a real man with my cock out standing over a toilet again. But before I knew it she was knocking my legs forward so that my knees buckled.

“Babies like you don’t stand in front of the potty!” She growled. “This is for GROWN UPS!” She barked. “In fact...why don’t you bow down and kiss it! Kiss the toilet and tell it how much you miss it!”

I whimpered as I obeyed her command, placing my lips on the lip of the bowl where the seat was up. Apparently Charles had poor aim, or I did a really poor job of cleaning it yesterday because it was dirtier than I would have liked.

“Look at you! So pathetic! And your fucking dick is STILL hard!” She laughed. “Put it on the toilet!” She commanded.

I was terrified, but after all this,maybe she was gonna finally let me pee, just on my knees like a loser. I placed my hard cock on the lip of the bowl I just kissed. Trying to mentally switch my cock from “horny” mode to “pee” mode.

But Amy slamming the seat down on to my cock switched it immediately to holy-shit-that-fucking-hurt mode.

“I didn’t say ‘pee’!” She yelled. Keeping the seat on my cock. “I want you to fuck it! Fuck the toilet while you tell it how much you miss it!”

You’ve got to be kidding me, I thought. I felt so ridiculous. So humiliated as I started working my dick back and forth in the tiny space between the seat and the bowl. It was not comfortable, but at this point I would take anything.

“Oh...potty...” I whimpered, “how much i’ve missed you! I wish I could use you so bad! Well for...you know...i...oh i just miss using you!” I hated how stupid I sounded as Amy cackled laughing at me, but I could feel myself getting close to cumming.

My excitement building.

Only for it to be ruined abruptly by Amy stomping down on the seat, hard. Pinching my cock painfully.

“Did I fucking say you could cum?!” She hissed while I writhed in pain. “Now let’s get your cage back on, potty-fucker, before you get too excited and spew your wittle load after only 20 seconds!”

******

I spent the next few days in further frustration and agony. Steve and I would keep sneaking away to the broom closet at work, only for him to cum in a measly 30-45 seconds. Not nearly enough time for me to achieve an orgasm or even so much as a few dribbles.

As much as it pained me to admit it, I really missed Charles’ cock up my ass. But he and Amy were so busy doing it with each other that he hadn’t even let me suck his dick in a while.

That didn’t stop them from feeding me the loads though. I was getting so sick of the taste of dick sweat and salty semen from a used condom. But after that night it would all change.

“I’ve got a surprise for you tonight.” Amy said as she changed my diaper when I got home. She had a coy look on her face that I couldn’t tell if it was more sinister or mischievous.

“What is it?” I asked. Trying not to get my hopes up, but my horny brain couldn’t help itself while she wiped me down.

“You’ll see!” She winked, sliding my super soggy diaper out from under me and rolling it up.

“Can I have a hinty hint?” I said, in my toddler voice. Knowing it was more likely to win me points.

“Let’s just say you’ll get a chance to cum in a warm, wet pussy tonight.” She smiled, winking.

I spent the next few hours trying to decipher what that meant. Was she finally going to let me fuck her? Surely not. But that didn’t stop me from picturing it. Remembering how it felt to be inside her. The warmth and wetness of her pussy as I was able to pound her with my fully erect penis.

But my cage snapped me out of my reverie as my cock attempted to get hard again.

Amy and Charles were on the couch cuddling and watching TV when I came in after finishing up the dishes.

“Are you ready for your surprise?” Amy asked, lifting her head off Charles' prominent chest.

I nodded. Quivering under their gaze.

“Okay...” Amy said, climbing off of Charles, “Meet me in the bedroom in 5 minutes.” She said seductively as she sashayed by. Leaving me and Charles in the living room.

I stood there awkwardly for what felt like forever. Unsure what to say. I thought about just leaving the room and waiting in the kitchen. As I turned to go, his voice came.

“I don’t know what she has planned for you.” He said without taking his eyes off the TV “But if she wants you to have sex with her, you will refuse.”

“I...what?” I said in disbelief, “but that’s my wife! I have every right to have sex with her!”

“And you belong to ME now!” He roared. Finally turning his head to me. “And you will do as I say and as I command! Or I will make life MUCH worse for you! Do I make myself clear?!”

I cowered in fear. I wanted to be strong. To stand up for myself. But this man had broken me. I felt a sudden rush of warmth in my diaper. I had just wet myself. I cringed at how pathetic I'd become. I nodded in compliance “y-yes sir...”

******

I knocked on the door to the bedroom.

“Come in” said Amy softly.

The room was dim when I entered. The only light coming from a few dozen candles she had lit. She was laying on the bed in nothing but a fiery red nightgown.

“Hi honey!” She cooed. “Come on in...”

I tiptoed in hesitantly, standing at the edge of the bed and trying to keep my cock from busting through my cage at the sight of her.

“Do you know what tonight is?” She asked.

Rubbing her hands along her half naked body and fiddling with her hair.

“N-no...” I said. Shaking my head.

“It’s our anniversary!” She smiled. A bit taken aback. I couldn’t believe I'd forgotten. With all this stuff going on and my world being upside down, I guess it slipped my mind. “It’s also been exactly one month since you’ve been caged. You’ve gone a whole month without cumming! Like we’d originally planned! Today’s the day you get released!”

She pulled at the chain from around her neck, the tiny key dangling between her voluptuous breasts.

Before I knew it, she had the tiny lock off my cage, and my dick was breathing cool, fresh air.

She giggled at my instant erection.

“Awww! Is somewon ready for their warm wet pussy?!” She teased. Shifting around on the bed so that she was right in front of me. Legs spread. Pussy glistening.

I couldn’t believe this was happening. After all this time Iwas finally going to get to have sex again. How I longed to be in there. But Charles’ threat loomed in the back of my mind.

“I...l’m sorry honey...” I squinted as I forced myself to say it “but i...i can’t...”

She stared incredulously. “Can’t what?”

It ripped my heart out to say it, but I had to:“I can’t have sex with you...”

She stared at me blankly for several seconds, then finally tilted her head back and roared with laughter. “Ohh sweetie! You thought I was going to fuck you?! You thought I was going to let you in MY pussy?! Oh sweetheart...I could never go back to your tiny dick after Charles! You think I got dressed up like this for you?! It’s for HIM!”

She reached behind her back and pulled out something. Plopping it on the bed between her legs. It was one of my soaking wet diapers from earlier, rolled up into a little tunnel with the letters “P-U-S-S-Y” written across it in sharpie.

“THIS is what you’ll be fucking tonight!” She said.

My heart sank. I don’t know why I got my hopes up. I don’t know why I even let myself think I had a chance. But I guess at least I wouldn't have had to turn her down the way Charles intended.

“But there are rules” she said after she managed to stop cackling, “for every hump you make inside that pissy ‘pussy’, you will spend one week in chastity.”

I groaned. Conflicted. It was like every aspect of tonight was a double-edged sword.

“Well?” She asked after what must have been a while. “Do you want to cum? Or should I just put you back into your cage indefinitely?”

I shook my head. Trying to hide my shame as I aimed my 4 inch dick into the small opening at the front. It actually slid in pretty easily. It was still warm and wet from earlier, but it wasn’t exactly pleasant.

Still. I started humping. Trying to make quality strokes. Trying not to think about the weeks that were ticking by with each pathetic hump.

“That’s one month...” Amy said after 4 strokes, “now 2...”

Already, I was up to 10 weeks. I thought I was going to die after being locked for the last 4. How had my life come to this?!

Just then the door creaked open behind me.

“Oh hi, Charles!” Amy smiled genuinely, “Come to watch the show?”

“Just wanted to see what ya’ll were up to...” Charles chuckled, sounding a bit relieved.

“Tom just racked up 3 months in the cage so far...” Amy explained.

Tears streamed down my face at the gravity of the situation. I still was nowhere close to cumming with everything going on.

I stopped.

“What’s the matter Tommy?” Amy asked, “do you not like your pussy?”

I sobbed. Shaking my head no. I hit my knees, and did the only thing I could think of.

“Will...will you let him fuck me instead?” I pleaded. Staring up at my gorgeous wife.

“You want Charles to fuck you in the ass? Instead of fucking your little wet diaper?” She clarified. A bit taken aback.

I nodded pitifully.

They both laughed. Amy pondered. “Hmm..i’ll agree as long as you wear your cage. I don’t want your little dick hanging freely and you getting any ideas. But you will also need to ask Daddy...”

I turned. Accepting my shame. Accepting what my life had now become. And trying to milk any bit of satisfaction I could get from it.

“Daddy...” I said weakly, looking up at his smug fucking face, “will you please...please fuck my ass. Please. I need it... I so desperately need it.”

Again they both laughed at my expense. Charles looked from me to my wife. Then back at me, and nodded. Dropping his pants.

Amy got my dick back in the stupid cage while I took Charles cock in my mouth to serve as lube.

Before I knew it, I was turned around and bent over the bed, my head in Amy’s lap. She stroked my hair like an affectionate mother as Charles pressed the head of his cock to my hole.

Already I could feel the difference between his dick and Steve’s as he pressed inside me. The initial entry was always painful, but after just a few seconds, that pain turned to ecstasy as he filled me up, and started pounding.

My eyes rolled in the back of my head. I buried my head in Amy’s legs to hide my look of pleasure, but Amy lifted me up and stared at my gaping ‘O’ face.

“I can’t believe what a sissy slut you are!” She said, shaking her own head.

I ignored her and just focused on the big, fat dick inside my hole. I don’t remember it ever feeling this good. Steve would have came 3 times by now. Leaving me unsatisfied. But Charles—Daddy—just kept going. Right into my P-spot.

“Ohhh yes!! Daddy!!” I moaned. “Yesss!! YES!!

Ohhhh I'm gonna cum!! Yes! Please! Don’t stop!! YESSSS!!!”

The pressure built from inside. Rising to levels I'd never felt. Then erupted in pure bliss as my dicklet erupted inside my cage. Spewing my sissy goo all over the bed and floor.

“Oh my...” Amy gasped, her eyes wide with disbelief. She probably had never seen anything like this before. “Well...it looks like we won’t be needing to take that cage off in three months, or even 12 months, after all, huh?”