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BECOMING A SISSY BABY BOY

 

(warning. This is a long, slow story, not your standard “spurt and go” kinda thing. Later on, there will be elements of  abdl (duh), anal, gay, sissy, cuckold, chastity, public wearing/wetting, spanking, alcohol drinking, and (much later on) pregnation! Enjoy nonetheless!)

 

Chapter one.

 

I’m not exactly what you’d call “manly”. Never have been, never wanna be. I’m not super fit, but not fat. Not super tall, or short. I’m average all around, weighing at 140 to 150 pounds, 5 foot 8, brown short hair and green eyes. But the idea of being called girly, sexy, hot, and above all, CUTE, are my dreams come true…….and then I found diapers.

Long story short, I’ve been wearing them for a long time. A good portion of my 26 years have been in and out of them, hiding when I need to, not when I don’t. But for the longest time, I was searching for someone, ANYONE who could participate in that side of my being. My girlfriend knows about it, but doesn’t really get it, or want a part of it, although she supports it and wants me to find someone as well.

So I started looking for daddy’s and or mommy’s.

A year of searching passed…before James moved into town. We started messaging back and forth, every day, getting a feel for each other’s personalities, quirks, hopes and dreams, fantasies. Mine were to be diapered 24/7 as a big time goal, or at least a bedwetter at second best. And also to be in a chastity cage long enough to learn how to orgasm like a girl (penetration only of course. I’m bi. Sorry, forgot to mention.) His aligned pretty close to that, also not looking for a live relationship, but rather that of a father and son/daughter, wanting someone to care for while still retaining some…*coughs*…SEXY elements. I was down, he was down, my girlfriend was down. In fact she talked with him as well, seeing how protective she was of me. It was funny, watching this 20 year old basically interrogate a 30 year old….in any case…

We decide to meet at a local bar. So local for me in fact, that it was right across the street. He was in town, had the night and next day off, so we planned it all out. I got ready for the evening, putting on my cutest bestest diaper (Littlepawz is my favorite), a pair of baggy jeans over top and a lion king shirt to bring it all together! And so I headed over.

Two drinks in, diaper already wet, I feel a tap on my shoulder. I looked up, mouth full of drink, and I feel my cheeks redden. The man before me, although not your cliché hunk, was HOT. Handsome at second best. Blue eyes, black hair neatly trimmed, some facial hair but not too much, just enough to pronounce the features. Standing somewhere between 5 “8” (cuz he’s taller then me) and 6 feet, his build was obviously larger then mine. But he didn’t scare me….usually bigger guys do that. It was probably his expression…..slightly embarrassed, warm eyes, crows feet at the corners from smiling a lot…and his voice! Like honey….

“Joel??” he asked.

“Um…yeah, hi. James?”

He smiled, the awkwardness vanishing as a smile took his lips.

“Yes! It’s good to finally meet you.” His hand went out and I shook it. The typical “new stranger” getup. You know how it is.

“You as well! Please, sit, I’ll get you a drink. I’m already two in.”

He laughed, sitting down and saying “two? I hope you came prepared for this level of….pampering”

Oh Lord. He’s a puny guy.

“Yeah, I did. Am. Is. All then words.” Things were getting slurry for me. I ordered his drink to the best of my ability, and after it arrived, we talked for awhile. Two more drinks went down my hatch (I don’t drink often, but when I do, I like to down those yummy sweet drinks), and two more wettings followed shortly after. At which point I stood up (slowly) and said.

“Ok….time for a change and then bed….sorry to leave ya like this James…”

His brow furrowed. “Leaving?”

“Yeah….this boy (I jerked a thumb at myself) needs a change badly. And I should probably stop now.” I laughed, finishing off my drink. “I live right over there, so no worries, I’ll get home just fine.”

I could see him thinking to himself before saying “Would you like me to help you change?”

Blushing time. With all this drink in me, I was feeling more submissive, more horny, and more compliant. Although I have to say, even though I don’t drink a lot or even all that often, I still somehow retained my…what do you call it….that line most people cross when drunk and then do dumb stuff? Yeah, I don’t cross it. I fall asleep first. Anyway….

“Oh….um….s-sure…..if you don’t mind the mess…..” my cheeks were on fire.

“I won’t mind, but if it’s TOO messy you might be in for a spanking.” He chuckled. I gulped and said nothing, simply paying my tab and his, much to his chagrine, and leaving a decent sized tip for the barkeep. As we walked, I found myself unable to walk straight, but when he placed a hand on my shoulder he helped manuever me, but let me stay in the lead.

I lead him up to my apartment building, fumbled for the keys before letting us in. I’m not a dirty person mind you, I do my dishes twice a week and usually leave blankets lying on the couch or beside it, maybe a cup or two as well if I’d fallen asleep the night before…..but as luck would have it, tomorrow was dish day so the dishes were piled up. I had had a meal the night before and fallen asleep on the couch, so there was a plate beside the couch with cheese stuck too it.

And my room was no different. I was in need of a new dresser, so clothes were piled up in a corner. But my diaper was clean as a whistle! But just looking at James, I could tell he was tsk tsking me in his mind….

“W-well….um…I know you probably won’t believe me, but you caught me before cleaning day…which is tomorrow.”

“…..” he said nothing, taking me by hand and leading me over to my bed and patting it, wanting me to lay down. I did as he suggested.

He grabbed a diaper off the shelf, a Bambino diaper with Teddy bears on it, and brought it, wipes, and the powder over to the bed. Without asking, he began to undue my pants. I blushed even harder, grabbing my stuffed fox Theese and used his body to hide my face. Within a few moments, my soaked diaper was exposed, with all the cute little pawprints dissapated. Still he said nothing, untapping it and folding it down to reveal my…..”manhood”….I don’t like calling it that. Tis a strange thing. Smallest, I’m at 2 to 2.5 inches. Hardest, closer to 7. When I drink? Total whiskey dick. But his hands and attention we’re waking him up, even just a little.

And STILL he said nothing! I wasn’t sure what to make of it….that is, until his strong hands suddenly rolled me over, and then proceeded to bring his hand down on to my wet asscheeks. THWACK! It stung like a BITCH, and I couldn’t help but cry out in pain and surprise. But I didn’t pull away….I was too deep into my little space and mindset. I gripped Theese, and the first smack was followed by 19 more…..

I felt tears coming to my eyes, but not a drop fell. Once he was done, he took a wipe and began cleaning my privates, as gently as I’m sure his strong hands could. He finally spoke.

“You took that very well, baby boy, you did a good job. Daddy is very VERY proud of you for that. Do you know why you got spanked?”

Through my pain and tear choked throat, I mustered “i-I think so….because my house is messy?”

By now he had turned me back over so we were face to face. Well, face to stuffy face, as Theese was still covering most of mine.

“That’s right. Baby or not, you should clean up after yourself. And at first I thought you might not be into punishment…but look! Someone has gotten a stiffy.”

Sure enough, despite whiskey dick, I was now rock solid. I guess the situation of being manhandled and humiliated by this man had stirred him from his drunken slumber.

“Ill keep that in mind for later. But for now….let’s get you ready for bed, huh?”

He unfolded the diaper, effortlessly lifting my legs and bottom and sliding it under my red bottom. Then he took the powder, plopped some into his hands and began spreading it all over my groin and bottom, not missing a single nook and or cranny. He shook his head at me, saying “Were gonna have to get rid of this hair, baby boy. It’s just gonna cause problems for you in the future.”

I nodded. “Yeah….I’ve been meaning to wax or something…..”

He continued his process, being sure to get everywhere before wiping his hands with a wipe, adding that to the soaked diaper beside us. Lifting the front of the diaper over my now receeding dick, he tapped it into place. A top tab first kinda daddy, I noticed, before he patted my bum. “There we go….dry as a bone and ready for the night!”

He pulled my shirt off, and tossed it into the clothes pile, and then tucked me in. “Do you mind if I sleep on your couch? I probably shouldn’t drive.”

“Y-yeah, that’s fine!” I replied, muffled from my bed covers.

“Alright then ..,…you sleep well baby boy” he kissed my forehead.

“Nighty night….”

I was in heaven. The attention, the care, the change, the words, the MOMENT …..ahh….

I fell asleep quickly, my last thoughts on how the next day would go…..

 

I found myself waking to the feeling of someone messing with my diaper. The first thing I noticed was my headache. Hangovers man. ..I should have drank water……the second thing was hearing James say

“Shhhh….it’s ok baby boy, I’m just giving you a change. You soaked your diapy while you were asleep.”

That’s the other thing about me. Because I’ve been slowly training myself to not qlench my bladder once I’m done peeing, it’s weakened my muscles. Means whenever I go to sleep drunk or exhausted, I can count on a wet diaper when I wake up.

James did the business, my mind going in and out of consciousness. I didn’t even notice that he had finished until he gently shook me till my eyes opened. He had a bottle of milk  in his hand, one of the ones from the cabinet I keep them in, and two pills.

“For your head. I’ll bet it’s pounding right now.” He wasn’t wrong, so I took the bills and washed it down with the milk. I was about to stop drinking until he raised it up, making sure I kept drinking. I drank away, my eyes on his to see if this is what he wanted, and judging by the silent affirmation I was getting, I was right. I drank till it was gone, he kissed my head again saying “Go back to sleep…I’m not far if you need me.”

I didn’t need to be told twice, drifting quickly back into the realm of a dreamless sleep…….

 

When I awoke, the headache had greatly subsided, and I could feel that my diaper was wet again. But I looked around first, getting my bearings. The hell…..my room was clean! All the clothes hung up in the closest, the dresser devoid of any water bottles or dishes….James had been busy. The sunlight was peeking out behind my blackout curtains, telling me that not only had the day arrived, but much of it had already passed. When I see sunlight in my room, it means it’s evening time.

I pulled myself from my bed, holding Theese by his tail and rubbing my eyes, before crinkling my way out into my living room. Clearly, James had not done just my room, but my whole house! And there he sat at my bar, doing what appeared to be some kind of math problems, before he looked up and saw me. His face immedisntly broadened into a smile. “Awwww, you look absolutely adorable!! Your shirt don’t hide shit, baby boy.” He chuckled, and I blushed.

“Shush….I can’t help it. Dis is my house and I can wear whatever I wants!” I couldn’t help a bit of little speech leaking out.

He nodded. “Your right, your right, but I can’t let you live like this. That’s why I cleaned up….and made a list of rules for you to follow. Nothing big, and nothing hard, and I promise if you stick to it, you’ll get rewards. Don’t follow them, and you get punished. No, not spankings (dang, he saw me expression), because those probably won’t work. Something different. I won’t tell you right now….you’ll find out eventually. Now then….” He stood up and came over to me, gently spinning me around.

“Lets get you changed.”

“B-but don’t you have work? I mean, I’m off today, but what abo-“

“Hush sweetheart. Today is about you getting to know me and the kind of things I like to do with my baby boys. And while we’re at it, why don’t you show me the toys you have?” he pushed me gently onto the bed. “No, just point. You lay there.”

I succumbed, and pointed at the top drawer of my dresser which he promptly opened, whistling to himself. “My that’s some fun looking toys. Wasn’t expecting stuff that seem so…vanilla..though.”

He held up one of my dildos, a 13 inch long by 1.5 inch thick. “Yiu can take all of this?”

I nodded. “Only if I’m in the right position…”

He bag to lay them out on the dresser in a row, taking inventory. “Inflatable anal plug, hollow anal plug, metal anal plug with a cute pink jewel (I blushed), big boy toy…” he sat that down with a resounding thud, it’s nine inch by 2.5 inch shaft wobbling slightly. “…I’ll bet you can handle this no problem, right?”

“If I’m warmed up enough I can take it all.”

He was impressed, clearly. But then he pulled out my too-small metal chastity cage. “And this lovely item is for your Prince parts eh? Why aren’t you wearing it?”

“Its too small…..plus I’m a grower, so at my smallest I can pullout of it. There’s a few on the market that works against that, but they’re so expensive…..it’s called The Vice.”

He “ooo”d at that. “Nice name. I’ll look into that. For now though, before your change, I think daddy deserves some playtime…..”

He picked up the long dildo and lube, coming toward me on the bed. My diaper had formed a tent by this point, my dick trying it’s best to be free.

“I can see your already excited for what’s next, eh princess?”

Princess? I’m a prince dammit! But I didn’t day that. “Y-yes sir….b-but I’ve never came from playing with my toys…..I’ve been told that if you can go several days without cumming then your prostate gets bigger and more sensitive…”

“Hence the cage?”

I nodded. He layed down the toy, his hands trailing across the front of my diaper before he slowly, and deliberately, began undoing the tabs. “If we make this a more common thing, I can guarantee we can train you to cum the way you want to……your dicklet useless, and your bottom full” the last tab came undone, my dick springing upward as he folded it down.

“But Daddy needs to feel his baby boys bottom squeezing the juices from his balls…the heat of your body wrapped around him….” His strong hands took hold of my legs, spreading them and lifting them until my rosebud was staring him in the face. He dipped a finger into his mouth, and began teasing my entrance with it, slowly pushing on it. I couldn’t help but moan a little….I’d long realized how much I loved having my ass played with, the sensuality of it, the naughtiness….and here this man was spreading it open with his finger, sliding it in and out of my hot hole. I closed my eyes, gripped my stuffies, and enjoyed the experience, before he said “You know what? Your actually pretty lose down there….I doubt we’ll even need your toy….”

And down came his zipper, and after a moment of adjustment, I laid eyes on (what I considered at the time at least) the most gorgeous dick I’d ever seen. Cleanly trimmed, very slightly bowed upward, is say between 7 and 8 inches long and a solid 2 inches thick….a daddy dick if I ever saw one.

And I WANTED it.

Even if I couldn’t get pleasure from the experience myself, I wanted this man to fill me with his cock, to enjoy my body, as a thankyou for taking care of me since the night before. My legs rubbed together in anticipation, my dick hard as could be, watching him intently has he applied a generous amount of lube to his manhood and then to my bottom. He lined himself up, taking hold of my waist in his hand and said.

“Are you ready baby boy?” I nodded….and he pushed. The head went in like butter, the rest taking a moment or too. I felt every inch as it pushed into my body, the heat of it…and then he was all the way in. I gasped and moaned, my instincts telling me to push this alien intruder from my hole, yet feeling so hot and submissive! Taken like a girl, soon to be fucked like one, and hopefully…bred like one.

Daddy slowly sank down onto me, his breathing heavy in my ear as he said “God DAMN little one, I knew you were gonna feel nice, but not THIS nice….your training is paying off~” his hands began trailing along my body’s curves, along my waist and hips, my legs and inner thighs, while his lips kissed along my neckline. I couldn’t speak, not really, my mind was on all the little sensations of the moment. His hot breath against my skin, the heat of his body, the scratching of his pubic and leg hair against my lower half….but I was thankful for this moment. It meant my body had time to adjust to his cock inside of me. But it didn’t last long, as his hips began to move back and forth, driving his cock in and out slowly. He never went all the way out, stopping at the head before pushing back in. He went slow….at first. And then he got into it, moving faster and faster, his breathing heavier and heavier. Before long, he was thrusting his entire length into me at full speed, his heavy balls smacking into my little ones. This is when things get less fun for me. Sure I was use to having big toys inside of myself….but not moving. My dick grew soft, my body screaming St me to stop….but I didn’t. I wanted this man inside of me. NEEDED his cum. So I steeled myself, held my fox, and let him have his way.

He lasted five minutes before his thrusting slowed, and with a final push to the limit, I could tell by his face he was cumming. Sure enough, I could feel the ropes of cum shooting into me, coating my innards. He lay there a moment, his breathing subsiding, and said “im going to pullout now……close your hold, princess when I do, ok? Don’t wanna stain your bedding…”

“Oh…ok…..”was about all I could manage. He gently slide out, and I squeezed myself shut, uncomfortable as it was, because I wanted to be a good boy. He nodded his approval, noticing my discomfort, and quickly grabbed a fresh diaper and the pink jeweled plug before making his way back over. He gently pushed the plug into me, sliding easily in due to the lubrication, and clearly enjoying the noises I was making as he did. “There we go…..daddy’s cummies get to stay inside of you now. Do you like that?”

“Yes….oh god yes…”

“Ah ah….watch your language….” He began the process of rediapering me smearing the powder all around my privates before deftling taping the diaper in place and rubbing my front. The attention was waking my dick back up…..

“All done. Did you enjoy that?”

“Y-yes sir…” I got a light smack on my thigh.

“Are you lying?”

I looked away. “…yes…it was a bit uncomfortable….”

He nodded and lifted me up into his arms like a child. “I know it was. You just need practice. Now let’s go get some nummies into that tum tum!”

I was living being carried, I felt light as can be though I was sure it was a strain for James. He carried me out and sat me on the barstool, made me a yummy bottle of chocolate milk and said “ok, you drink that up while I make us some tacos. I made you a rule list this morning to help get you in a better place of living, but don’t turn it over yet. You just read through this and see if that’s something you can handle.”

He slid the list over to me, and without one hand holding my bottle to my mouth and sucking, I read it over.

1.       Diapers are your underwear, not exceptions. If you need help getting more, just ask.

2.       Dishes are to be done as you go. If you dirty a plate, you wash that plate before bedtime.

3.       Showers/baths every day.

4.       Enemas daily during shower time.

5.       20 minute anal training after enema. No cumming unless your bottom has a toy inside it.

6.       Three changes per day, unless more are needed. Morning, after work, before bed. Whether the diaper is used or not.

7.       Drink a lot of fluids to keep your bladder full and constantly running. The enemas will help keep your diapers wet, not soiled.

8.       Start a small savings, 25 to 50 out of each paycheck (I’m paid weekly). This is for emergencies only.

I was nodding along. Most of this was my daily routine anyway, give or take a few enemas or changes. By now my bottle was half empty, and the smell of cooking beef had filled the apartment.

“Well? Do you find the rules acceptable?” James asked.

“Yeah! I think I can do this. Been meaning to step up my game anyhow.”

“Good….then starting tomorrow, the rules take effect. And remember…..no breaking them, understood?” he drained the beef, reapplying it to the skillet and setting it on a lower heat. “Im going to be heading home tonight after I tuck you in. But I think we should schedule another time next weekend. Is that alright?”

“Oh hell yeah! I’d love that!” I replied, taking another sip of my bottle. He gave me a disapproving look.

“Yiur enthusiasm is appreciated, but watch your language please. You’re a baby, and babies don’t swear.” He began making me a soft taco with OUT the works. Veggies suck. Bleh. “Ive also noticed you have yet to call me Daddy….that’s ok, I understand. It’s an earned title, not a given one. And I honestly…”he set my plate down in front of me. “…intend to earn it. I’ve spoken with Annie a great deal (my girlfriend) and she agrees with my plans. She knows how much you want this kind of lifestyle, and while she’s not super into it, she wants to support you. So keep that in mind through the week, ok baby boy?” he tossled my hair, taking my now empty bottle and refilling it.

“Yeah….I know she does. I love that girl so much….d-daddy…” he shook his head, handing me back my bottle.

“You should only call me that when you feel comfortable doing so. Go ahead and eat up.” He took the list back from me, and as he did I noticed what looked like another list on the back. He winked as he folded it up and put it in his pocket. “That’s for a later date.”

Oooo, I was SO curious now. But I did as I was bade, eating my yummy taco with lots of cheese and Catalina. James made himself a plate, sitting on the couch and proceeded to watch Stranger Things. I was farther into the show then him. I finished my food, set the plate in the sink and was about to walk off before I remembered the rules. So I washed it real quick, dried it and out it away. He watched me do so and nodded his approval. I was feeling pretty full at this point, tummy full of food and drink, so I got my stuffed foxy and curled up beside him, my head on his lap. I felt the urge to pee, and knowing I was secure in both my diaper and James’s embrace, I let it go, feeling the warm heat spreading across my privates. The plug was still in place, but knew his cum was probably leaking out and into my diaper. The thought was making me hot and ready, my penis growing in size beneath it’s cotton confines, so I reached down and began rubbing the front of my diaper to satisfy myself. James noticed, saying “Are you feeling naughty, sweetheart?”

“Uh huh….” I said, meekly.

“Here….let daddy do it for you…..” he moved my hand away, taking it’s place and rubbing my swollen dick through the diaper. He pulled me into his lap for better positioning, his chest against my back, while his other hand rubbed my tummy. “Go ahead and make your cummies baby boy…..shoot it into your diaper. Daddies got you….”

I was so turned on right now. Manhandled again, pleasured, in little space and being masturbated into an already wet diaper……it took less then 3 minutes before I shuddered, expelling my load into my waiting diaper. But he wasn’t done there, as he reached into the front of my diaper and scooping a glob of my cum up with his fingers, he brought it to my mouth. “Open up….your gonna get used to the taste of cum sooner or later….”

He wanted me to eat my own cum?? I suppose what he said made sense…I was sure he was gonna have his own in my mouth sooner or later, so I gingerly opened my mouth and his cum covered fingers went inside.

“Lick them clean…” I did so, sucking for good measure to make sure I got it all. The flavor was acidic, the taste strange, and I could feel it sort of numbing my lips and throat when I swallowed.

“Good boy!” he patted my padded bottom, positioning me to be more comfortable. “Now let’s cuddle some…”

And cuddle we did, me still sipping on my bottle. The milk did little to get rid of the cum flavors effects, but it did a lot to fill my diaper as the evening went on. A few hours later, two more bottle refills and a season finale, I was sleepy and ready for a change. James heard me yawning, saying “Alright baby boy…..time for nite nites….”

“Nooo….don’t wanna….”

“Shh….I’ve got you. Little boys need their sleep so they can be big boys at work. Come on.” He lifted me up into his arms once again, and I let him, feeling small and helpless as the child I wanted to be. He filled up my bottle with water, rinsing it out and then filled it again, carrying it into the bedroom with us. He layed me down, and went through the diaper change ritual, but I was too tired to even care. My sleep regime was getting to me, having been used to bedtime hours ago and so I was already nodding off when he finished his work and tucked me in, making sure Theese was there beside me. He bent down and kissed my head. “Goodnight little one. I’ll see you next weekend…be s good boy, ok?”

“Ill try.” I gave him a sleep smile. “Nighty night….”

And before he had even shut the door, my world had collapsed.

 

 

I woke up the next morning to my alarm going off. Well, several alarms, as I had several set in case I slept through any. I could feel my diapers embrace around my hips, and still groggy, I pushed my morning pretty into it’s waiting confines. Satisfied my bladder was empty, I went about my morning.

Straight to the coffee machine.

James was gone, and in his absence the place felt lonelier….bigger. But at least it was cleaner. Coffee was brewing, so I had my morning smoke (babies don’t smoke, I know, it’s a bad habit. I’m working on it, alright?!) while it did it’s job. I had to leave for work in an hour, so I took my time to wake up first. Drank a cup of coffee, changed my diaper, and put on my work clothes. Since I work in a hot environment, the plastic backing off my diapers tend to chafe the inside of my thighs, so a tykables onesie under my work clothes seems to fix that problem just fine. But with the pants as small as they are (small guy, small pants. 32x32) they make quite the diaper bulge!

With everything in order, I went to work.

I work as a live hanger for a poultry plant. Not exactly the right job for a baby boy, nor does it fit my MANLY attitude (pffttt…..) but it pays the bills. Also helps keep me in shape.

Work was work. A pain, an annoyance. Got scratched by the turkeys a little, bit no biggie. But all throughout the day I was constantly aware of the diaper, and made sure to use it as I should. It was one of those premium ones from ABuniverse, a Littlepawz one, so it held quite a lot by the time work was over. And my day and mind we’re filled with thoughts of James and the day we had had together….it seemed like a dream. I wanted to see him again as soon as I could. Not just for sexual aspect…..but I absolutely loved the way he was a daddy. It seemed like his thoughts were on caring for me first, and everything after that was just a bonus. Just the way I like it. If I had my way, I’d leave the sex out of my little space. I like to believe that littles don’t need sex, nor should seek it…..but as adults, we crave and lust after that attention and love. So oh well. Just another fantasy.

Driving home was fun, feeling my soggy diapy squishing under my bottom. I found myself rubbing it as I drove, lewd thoughts crossing my mind…..

I got home, and got ready for my shower. James said to have a daily enema….so I did as I was told, doing my best to clean myself out, getting rid of the poopy mess while using a few of my toys to help…..I guess the word would be plungering. Plunging?....the rest out. I dried off, rediapered myself, and got to work on some food. Nothing big….barely healthy….but filling. All the while I was still thinking about James…..and since I had just had some fun in the shower, my thoughts were turning to the more sensual side. My dick was fully awake in it’s plastic encasement, striving for attention, so after my food, and because of the rules set by James, I decided it was playtime. I pulled down my diaper, lubed my biggest toy, and pushed it inside myself. I worked it in and out, getting my ass comfortable with it’s intruder, before pulling my diaper back up to hold it in place. Now my ass was filled with a slippery toy, and every movement caused it to either slip out s little, or slip further in. I was full submissive mode now, moaning from the mixture of feelings I was receiving from this rubbery cock. But I didn’t stop there. I turned my thoughts to the most sexual kind I could, getting my dick as hard as I could, and I began to rub myself through the diaper….before long, I was caught between my front and my back, trying to keep the feelings balanced so I could cum as James had told me to. But with my training so crappy, it was a difficult task. But I managed. I found that pretending the cock was James’s, my horniness stayed stronger for longer, and I was moaning and calling out for him….

“Oh James…..oh god, push that cock inside of me…yes…..make love to your sissy baby boy…..ahh…..I wanna feel your cum shooting inside of me, leaking out of my sissy ass and into my diaper….yes….yes! Yes! Ahh!!”

And as requested, my cum was shot into my awaiting diaper from the thought of this man’s dick making love to me.

Once my sexual high had dimished, I removed the dildo and continued with my evening, washing the dishes like a good boy, and then settling down for bed. I hadn’t wet myself yet, and didn’t want to waste my diaper (them things cost money man!) so off to sleep I went.

And that’s how my week went. Except for Wednesday. I broke a rule there. I was exhausted from work, so after my meal I decided to do those dishes the next day instead. Which I did do! But because of the longer dish washing time, I knew I didn’t have enough time to train as I wanted….so I admit I  didn’t cum with a toy like I was supposed to. But who cares, it was one day. Friday was good though. I did everything as I was supposed to, plus it was payday AND a shorter day! I spent that day doing my bills and making sure my apartment was cleaned up for Jamess visit tomorrow, that way I wouldn’t get spankings again. As much as I think I liked them, I didn’t like seeing him disappointed…..which I found curious. I seem to already consider him a daddy figure, despite only knowing him for s day…..well, less then a day really. No matter. That evening I had more fun with my toy, calling out for him again…this time calling him daddy. I was feeling more submissive then ever, excited as well, for what the next day would bring. But because of work, sleep still came easy…..

 

The next day, I awoke at my usual time. EARLY. That’s my job for ya. So after wetting my nighttime diaper, I went back to sleep for a few hours. I woke back up to the sound of my doorbell ringing. Crap…I’d slept TOO long! I jumped out of bed, ignoring the idea for pants(it had to be James, so oh well) and ran to the door. Sure enough, looking through the peephole, there he stood! Daddy..or at least, the man I WANTED to call daddy. He was dressed rather nicely, dark blue jeans with a white button up shirt tucked neatly into his pants. I quickly opened the door, not caring about my own missing pants, saying “James! Hi hi! I just woke up.” I smiled for him.

He laughed. “Oh did you? Late morning for you isn’t it?” he stepped inside and we walked into the living room.

“Yeah, it’s my day off and I wanted to have lots of energy to spend time with you!”

“Awww, thanks baby cakes. I must day, you look absolutely adorable in just your diaper and t-shirt.” He patted my bottom, definitely noticing my wetness as he gave it a squeeze.

“T-thank you…..” I blushed…..I think I do that hardest when I’m around him.

“Lets get you out of that wet diaper, huh? Don’t want you getting a rash! Have a seat on the couch there a moment and we’ll get right to it.”

The couch? Not the bed? I followed orders anyway. He went over to my tv though, plugging what looked like a USB into the back and turning it on. It loaded up a few files, generic names attached to them. But it had dates. I was confused. He went and got my supplies while he was talking, saying “So! Did you follow the rules I gave you this week?”

“Um…..mostly…..one day I did dishes from the last day cuz I was really tired….and I had a day where I came without a toy…..” I said, looking away. He nodded along, as though he already knew. And with that, he pressed play on my TV remote. Suddenly, a familiar setting was showing. My room! And there I was on the bed, rubbing myself sleepily.

“You didn’t lie, which is good. The punishment would have been worse if you had. But you’ve also omitted some things. I didn’t see many 3 changes per day. Several times you went OVER the 20 minute cum limit…” he nodded at my sudden confusion…and horror. “That’s right. 20 minutes to cum. Go over that, and you were to stop playing with yourself. Now before you get angry and lash out because I was recording you….just know that it wasn’t my idea. Nope, it was Annie’s. Your girlfriend. She knows you have a hard time controlling yourself, and wanted to show me what kinds of things you do in your spare time. Of course SHE also wanted to know. See what kind of guy you were when you were alone. Not much of a surprise as to what you did during the week. Not much to do with so little time on your hands. So baby boy, I apologize for the recording. Now I think it’s time for YOUR apology, and your punishment. Do you accept?”

I found myself in an awkward situation….here I lay, diaper off, getting hard at his dominance and yet feeling so little and ashamed for being outed. I could only mumble a feeble “Y-yes sir……”

“Good….” He sat down, and pulled me over his lap till my bottom was in his face. I couldn’t see him, only hear him. “Now…..say your sorry.”

“….I’m sorry Ja-“ THWACK! The hand lay down into my bottom and I cried out. He wasn’t being as light this time.

“Try again. Apologize for me.”

I hesitated before….”Im sorry da-“THWACK Another sting. Ok, so it wasn’t the name he cared about…..um…..”I apologize for disobeying!”

…….that was the magic word. Cool. “Good boy. Now start counting.”

And the spanking continued. He alternated between my cheeks and my thighs as I counted out each one in painful gasps. He went on for what seemed like forever, and once we reached 25 I wasn’t sure that he was even going to stop….I could feel the tears pushing at the corner of my eyes, struggling to drop down onto the couch below….and sure enough, once we reached 35, I felt them start to roll down my cheeks. I wasn’t sobbing….but I was definitely crying. And though I seemed to enjoy the play aspect of punishment, which is for sure what my dick first thought when he started spanking me….after the 20ith, he went back to being limp from the pain.

50 spankings later, he stops, and turns me around in his lap till he’s holding me and rubbing my back, while I was sniffled and moaned into his shoulder.

“Shhh, shhhh, I got you sweety, I got you….it’s all over now. I’m sorry I had to do that, but it was for your own good…..I know you enjoy light play so I had to get a little harder with you. But it’s all over now……daddy’s reset the playing field. You’re a good boy, I got you….”

We stayed like that for a solid 5 minutes, him just consoling me while I tried to pull myself together. My ass was on fire, my pride broken, my hopes for a fun morning shattered. But he was holding me so close, so tenderly, I felt safe and secure, even though this man had just caused me more pain then I had felt in a long time. He was right….I’d broken the rules. Once I’d stopped sniffling (his shoulder was now a little wet), he pulled picked me up and carried me into my bedroom, laying me down on the bed.

“Ok baby….daddy’s gonna get you ready for the day, alright? I promise to be very gentle with you.”

I nodded my acceptance, and he went into changing mode, but this time taking the bottle of baby lotion that I rarely used, and spreading it across my flaming ass cheeks. I winced at the touched, but then the cool lotion calmed the flames….so nice….. Then he took something out of his pocket. A velvet bag?

“I got this for you and Annie. Whatever happens with us, you and her will still have it. It’s my gift.” He dumped it’s contents out onto the bed, and I saw a shower of pink plastic pieces Cascade across the bed. I recognized it immedisntly. The Vice! The chastity cage I’d been meaning to get…..oh god, I was going to be controlled properly now……usually Mr dick would come to life at seeing this, but I was still too emotional for such things, and he began fitting the cage around my member.

“Judging by your growth and length, small everything might work. We’ll have to see how this does…..” the base ring slipped around my balls and dick, and before I knew it, on went the cage. It looked so massive compared to my dicks current state, but I knew once I got turned on that would change. On went the antipullout piece, and with a quick CLICK……the cage was locked in place. He wiggled it around a little, testing the positioning. “I think this will do. Only Annie have the keys now…..so your playtime is over!” he chuckled, and continued the diapering procedure, getting me into one of my Littlepawz. Once done, he turned me around on the bed and sat down behind me, holding me to his chest, my back to his front, and rubbed my tummy. “Now that that’sall out of the way……I have a proposition for you sweetheart. Thanks to your girlfriend. It was her idea.”

“What was? Is?” I asked, enjoying the tummy rubs.

“Well….she wants you to move in with me. To take care of you, train you as you want, AND get you financially stable and in the positive. Youll want for nothing, but be spending nothing. I’ll take control of your finances, you work, and be a happy baby like you want to be. She says you have some debts, so we’re gonna take care of those, and rebuild your credit up. That way, she and you can have the happy life your both dreaming of! Since she can’t join us yet, this is the perfect time to take care of all your problems. And dreams. Diapered like you want to be. Chaste like you want to be. Constant attention and love. Training. Stress free for….”he thought about it.”….a year? Somewhere in that time frame. Plus, as a bonus….” He winked. “..I can cook! What do you think? No rent required! I make enough to handle living conditions. Your money will go to food, diapers, and debts.”

I thought about it….long and hard. What problems would this cause? What issues? I’m seeing positives…..and very few negatives.  Besides him taking my money…….but if he did as he said he would, I’d be debt free. I could buy my own place later if things went sour, even cancel some bank accounts. And prove he screwed me……..after thinking about it for s solid ten minutes, I pulled his arms around me tighter, and mumbled….

“….ok….let’s do it.”

He hugged me tight and kissed the top of my head. “Then let’s get started….”

And we did. That day was spent packing most of my things into boxes he had brought along in the hopes I’d say yes, and after ordering a uhaul, we loaded it up. The entire time I wore just my diaper and shirt with a pair of tennis shoes….who cared if anyone saw? I wasn’t coming back. And it was a warm day out….plus I enjoyed the looks James kept giving me. By evening time we had most of the house packed away, 3 large bags of trash I didn’t want to bring along, and all my diapers put in separate boxes for easy access. Then we loaded ourselves up and headed out.

Thankfully, the drive wasn’t as far as I feared. Outskirts of town, lots of open fields with nary another house in site. It seemed James liked his privacy…..good, cause I was enjoying the fresh air on my legs.

He pulled into a driveway leading up to a pretty decent looking house. Nothing spectacular, probably 40 years old, but in fairly good shape. Two story,  quaint, and white. Your run of the mill farm house I’d say….without the farm. So far, I was LOVING it. There were even some tall pines trees partially secluding it from the main road, providing more privacy to the dwellers of the home. We pulled up beside the house, and James said “Okie dokie! We’re here! I’ll bet you could use a change after all that work we did, huh?”

He was right. I was nearly leaking…..or maybe I had? After checking….yep, I had. Oh well. It’s a rental. I nodded my comfirmation to him, hugging Theese to my chest.

“Well then, we’ll get your diapers and basic stuff inside, and then we’ll get you changed ok? Come on.” He unbuckled me (I could have done it myself, thanks.) and we got out, getting out the diaper boxes. He took the biggest and heaviest for himself, so I helped open the door for him. We got inside, and WOW……everything looked so nice! Everything was clean, everything was ….old? Antique? Whatever it was, this place was THEMED for SURE. And I liked it. Probably the southern in me. I followed behind him, taking glances at the rooms we walked past. Kitchen, cool. Dining room (do people use those?) Bedroom, his more then likely. Guest bedroom (you could tell by the uglier bedding.) We walked up a flight if steps, into a hallway, and he turned to a closed white door.

“This is your room. I’ve had it set up for awhile, in the hopes I’d find someone like you. It’s definitely not finished, but we can sort that out later…..” he opened it…..and there were pastel colors everywhere. The walls were a light purple, or lavendar, the carpet…that’s not a carpet, sorry. It’s those foam alphabet padding that the letters come out of? Really soft and plushie! There wasn’t much furniture, or anything on the walls, but a adult sized toddler bed sat in the corner. I had a full sized window as well, stretching nearly wall to wall on my left side, with a closet directly next to it on the wall in front of me. It was a decent sized room, large enough to fit my computer setup and some dressers. That would be all I needed.

“Ok….what do you think? I was planning on putting your diapers in the closet there, with a bunch of shelves to kind of display them. Keep you in your little mind set.”

“I had the same idea! And yeah, I love it! I was expecting smaller to be honest.”

He laughed. “theres always the spare bedroom downstairs. That’s smaller if you want!”

I could tell he was teasing me, so I stuck out my tongue at him.

He gave me a look. “Don’t stick out your tongue unless you plan to use it, naughty boy.” He set down my boxes, rummaged through them and got out the changing supplies. “Onto the bed please.”

I happily laid down for him, my soggy diaper on full display from the entire day,  and watched as he went to work. The attention caused my dick to struggle in it’s plastic cage, but it held true to it’s noteriety. “I can see your going to have some issues getting your middle peepee under control…..that’s ok baby boy. That’s what the cage is for.” He winked at me and gave it a nudge….and I moaned from the pressure, pushing my hips slightly in his direction. He just ignored me, finished up the change and then lifted me up into his arms. “Im going to give you a tour of the house before we get settled in for supper. Tomorrow we’ll unpack everything. Ok?”

“Ok!” I kissed his cheek, feeling very little and happy at that moment. He proceeded to walk me around the house, showing it off to me while describing his plans for the future. Those were boring…so I won’t add them in. Suffice to say, this house was well equipped for handling two to three adults, even some extra kids (I suppose I count as one of them? XD maybe half an adult.) Three bedrooms, one of which was being used as storage, kitchen and dining room, two bathrooms (I watched him lock the extra one in front of me. He said it was so I didn’t get any ideas. Phooey on you daddy!) a basement and lots of yard area, including a tire swing! And a lovely maple tree I wanted to climb…..

“And that’s the property. It’s not a mansion, but it does what I need it to.” He said.

“Keeps you dry??”

He tickled my sides, causing me to laugh and squirm in his arms

“Exactly you little cutie! Let’s get some food and then get you into bed.”

“Okie dokie!” and that’s what we did. He made us some hotdogs and french fries, gave me a bottle of yummy milk to drink up, and then we cuddled on his couch watching anime. One Piece of course. I picked it out! The evening was coming to a close though, my eyes were drooping and I was already starting to doze off….but my dick was hard in it’s cage, having been used to getting used in a daily basis. I was too tired to care though, unable to keep a single lewd thought in my mind…so it wasn’t too bad. I felt Jamess arms lifting me up again, and carrying me to my new bedroom. He tucked me in, making sure Theese was snug in my arms and my personal fan was doing it’s job of keeping the air freshener and rotating before kissing my head, and softly saying

“Sleep well, my little one….and the sweetest dreams….”

End chapter one.

 

 

Chapter two:

My first week with James.

 

I woke up before James did, all thanks to my dick straining against the cage. I could already tell that morning wood was gonna suck for awhile….but I also knew that it would get used to the cage and stop doing it. I squirmed for a bit, trying to get comfortable…but alas, with all my attention on my dick, there was no way it was going to  get flaccid without some help. So I got up, my diaper still dry, and decided on a smoke. I left my pants off, but put on my coat, heading outside as quietly as I could. The morning light was just making it’s way over the horizon, a beautiful mixture of blues, purples, and reds. The air was nice, I’d say a good 60 degrees (Fahrenheit) so pants weren’t even needed! By now my dick had (mercifully) gone flaccid, so I let my morning pee out into my diaper. I laid my hand on it as I did, feeling the warmth spread around my crotch. What a wonderful feeling…..I was going to love being diapered everyday. I thought about changing….but I wanted James to do it. Plus these diapers could hold A LOT more….so why bother? I tapped out my cigarette, made sure it was totally out, and headed back inside. Threw the butt into the trashcan, and decided to peek in on James. His door was wide open….I looked in on, and found him laying on his bed in just his boxers, blankets off to the side. Seeing him without his clothes, I got to see his true physicality…..he was muscular, hairless, and delicious looking. No wonder he could pick me up without much issue! And the fact he had a hairless chest? Just like me? Well that meant that bare chest cuddles would be VERY much enjoyable….

With his body layed in front of me, all these thoughts in my mind sent the blood back down to my nether regions. I was horny. And I wanted my daddy. I made my way over to him, trying my best to be quiet (the diapers crinkling made that pretty difficult), and gently teased the boxers around till I found what I wanted. Flaccid, his penis was still a decent size….clearly not a grower like I was. I reached in, gently pulling it out and holding it in my hand. It was hot….thick….and boy did I want it. So with one hand rubbing myself through my diaper, one hand around the base of his manhood, I leaned down and slowly began licking the head. It was salty, and wanting more, I took the entire head into my mouth, rubbing my tongue across it’s form. Within two minutes it had risen, getting more hard as time went by, and still I sucked and played with it. Before long, James began to moan in his sleep, so I increased my playing. I could taste the precum leaking from his head, feel it numbing my tongue much as mine own had. But the taste of his was much better, more sweet…probably because he had a better diet then me.

I suddenly felt him moving, and I made to move back off him, but his hand quickly pressed against the back of my head, holding me in place.

“Someone woke up early…and apparently wanted daddy to wake up in a good mood!” he said.

I looked up at him, smiling around his dick, and then sucked harder, letting his hand press me down a little more. I’m not good at deep throating, so I used my hand to keep myself at a comfortable length, and continued my playing. But with him awake, I could go harder…and get more into it. So I climbed up on to the bed, laying down at his feet, and using both hands down I went to work. Sucking, teasing, drooling and taking it’s length into my mouth, I worked my magic. I wanted to prove my worth, and for the next 5 minutes I did just that. His breathing got heavier, his moans louder, and through them he was talking to me.

“Yeah, baby boy just like that…ahh….suck your daddy’s dick like a good boy…..god yes…ahhh…yes….HERE IT COMES!!”

I felt his dick spasm in my mouth, his cum shooting against the back of my throat…I almost choked. ALMOST. I stayed where I was, sucking the last drops from his dick before crawling up to his face. I opened my mouth, showing him his own semen and then I swallowed it and smiled. He smiled as well, saying “Good boy…..cuddle with daddy for a little bit, huh?”

I happily obliged, curling up beside him so my head was on his smooth muscular chest. His arm wrapped around me, holding me close while I listened to his heart beat slow decrease to normal. When it had settled, he looked over at me, and I up at him. “Hows your cage feel?”

It was uncomfortably tight at the moment. “Im ok.”

He reached down, feeling my wet diaper. “You’ve got room for more. What do you say we get some coffee and breakfast?”

I smiled. “That’s sounds great!”

He nodded, rolled off the bed and I followed him out into the kitchen, where he lifted me up and sat me on the counter. I enjoyed being up this high, watching over his work. He got the coffee going, started on some eggs and bacon (LOVE bacon), and once the coffee was done he asked me how I like it. I told him tepid and black. Sue me, I’m weird. With that, he poured it into a bottle for me (since it wasn’t too hot. Added ice.) and handed it over. So I had my morning coffee while he made us food. But…I hadn’t had an enema yesterday. And the coffee was making my tummy churn.

“Um…….James?”

“Yes?”

I struggled a little to get the words out. “I…have to go…”

“Then go, little one. Your in a diaper for a reason!”

“Not…number one….”

He looked at me with a smile. “Did I stutter?”

Ohh….so he was willing to handle messy diapers too. Well alright then! I got up on the counter, squatting where I was, and gave a little push. The mess mushed it’s way against my bottom, the heat and naughtiness making me blush a little. Once I was done, I say back down on the counter, letting the mess get all over the inside of the diaper. I didn’t want to make this easy for him, heh heh. He watched me do my business, and noticing my little smirk, said, “You may think your clever….but all you did was make my day a little easier. You’ll soon see why. And speaking of that….” He went quickly to the bedroom, and came back out with a familiar piece of paper, handing it to me. Then he went back to cooking.

“Flip it over this time. It’s your new rules.”

I did as he asked, wincing a little at seeing the original rules….which I hadn’t handled so well. On the back, a new list….

·         Diapers 24/7. You do not ask to be changed, nor do you change yourself. Period.

·         Bedtime is at 6 pm, no exceptions. This is both because you’re a baby, and because of your job.

·         You have a weekly allowance of 75 dollars. This should be used for gas and possible a few knock knacks you may want. You can save up if need be. All other bills and finances will be handled by me.

·         Your smoking will be monitored and regulated so as to help you quit.

·         No touching yourself or playing with yourself without my supervision and permission.

 

I sucked on my coffee while I read, the smell of my messy diaper already filling the area around me. I personally was used to the smell…..not my first messy diaper by a long shot. James was finishing breakfast, making both he and I a plate.

“Well?” he asked.

I nodded. “Yeah….I think I can do this…”

“We will see, now won’t we?” he set the plate down for me, getting me some silverware as well. Dippy eggs, bacon and buttered toast. Yum! “We have a list of things to do today, so if you want any playtime when we’re done, you best eat quick. We need to unload the uhaul, take it back, pick up our cars, unpack your stuff…..” he wrinkled his nose at my smell.

“Phew! And DEFINITELY get you changed!” he laughed. I blushed. Nonetheless, I started scarfing down my food, hungry as I was. He watched me as I ate, and it left me feeling like he either didn’t trust my eating methods, or he just couldn’t keep his eyes off my sexy body~ (joking). We finished our food, he out our plates in the dishwasher (yay! Dishwasher! I hate doing them by hand), before he picked me up and carried me to the bathroom. His hands were pressed against my bottom, making the mess spread even more against my body. Setting me down on the bathroom sink, he started warming up the shower.

“Let’s get you cleaned up. Before you know it, this will be a daily thing for you. Messes in the morning.”

“Really?”

“Really really kiddo. All it takes is a change in diet and a little training.” He stood me up, undoing my tabs, and being very careful not to get the mess everywhere he lowered it from my body. Setting it to the side, he had me step into the nice warm water of the shower and began rinsing me off. It felt nice to have the ick washed away from me, not having to do anything but enjoy the experience. And enjoy it I was, that is, until he said….

“Uh oh.”

“What is it?”

He held up the cage around my dick. “Look.”

The cage was failing! My balls had managed to get out….all that was holding it on was the antipullout piece….

“Oh…..I’m sorry….”I said, feeling sad.

“Sorry for what? This is hardly your fault, baby boy. It just means I have to take other options.”

“Like what?”

“Well, I can either modify this one, have a custom one made, get you a Prince Albert, or, well, I guess castration.”

My eyes widened a little. “C-castration?”

He gave me a quizzical look. “I meant it as a joke, but judging by your expression and tone of voice, you don’t seem that much against it……if you like, we could do that, but I war-“

“No no!” I quickly said. “I-I wanna keep them…Annie and I want to have kids.”

“Ahh…that’s your goal, huh? The baby boy wants a baby.” He chuckled to himself. Because I didn’t. Too embarrassed. “Well alright then, I’ll see what I can do. Until I can figure this out, well keep using this one.”

He finished cleaning me up, dried me off, and took me back up to my new room for a change. He didn’t seem to be in much of a hurry, taking his time as he oiled me, powdered me and then securely taped me into my fresh diaper. “There! All clean and ready for a busy day! It’s supposed to be nice out today, so I think a pair of shorts will be good for you, eh?”

I happily nodded, letting him do his thing. Ten minutes later, I was dressed and feeling energetic! And VERY little. I was, however, a little timid when he clipped my paci to my shirt. When I asked why he’d done that, all he said was “It completes the look” with a wink, and then popped it into my mouth.

Unloading the uhaul didn’t take us long. I’m ashamed to say, I don’t own much. I’m a minimalistic kind of guy…..my most expensive things were my tv, my Xbox, and my PC. And I don’t have many clothes to boot….

The drive back to town was short, albeit a little worrisome. I knew better then to hide my paci, and knowing any other passengers in the cars beside us could see me, I found myself shrinking down into my seat. James only laughed whenever he saw me do this, but said nothing in return.

We got our cars and returned the uhaul, and now knowing the way back I easily followed James back to his house. I sipped anxiously from my coffee bottle which he’d refilled before we left, avoiding all contact from any other drivers I may have passed along the way.

Once home, I got to work unpacking my things. Setting up my computer and tv was fun! Everything else….not so much. More often then not I found myself messing with my electronics instead of my other things. And for good reason. PC equals fun. Clothes….not so much.

An hour or two into unpacking (I wasn’t keeping track) James had refilled my bottle twice, and I’d filled my diaper once. Still lots of room for more though! So I kept at it. By noon, my room was nearly done! All my diapers in place, my stuffies lined up on the bed in a neat and (might I say) adorable fashion, PC set entirely up on Jamess WiFi and my tv was perfectly aligned so there would be zero glare from the outside light. I had to say…there was something about seeing my room in such a new light, knowing I would be spending St least the next year in here in diapers and in Jamess care that made me feel….hopeful. Excited even! I happily got onto my computer, fired up Minecraft and joined my favorite abdl server. I was telling everyone about my new place and setup, about an hour later, when James knocked on the door frame, looking in on me.

“Everything in order?”

“Yeah! I was just making sure everything was working. “ I said smiling at him.

“Looks more like you were playing a game.” He replied sarcastically.

“Hey…I did what I was supposed to do…..”

“Yes you did, and a good job at that.” He walked over behind me in my chair, leaning down and feeling my diaper. By now I was near soaked.

“But it’s time for a change. Among other things. You probably wont enjoy this.”

“W-what is it?”

He turned me around, pulling me up to my feet. “Don’t worry, it’s just hair removal. Like you wanted. I’ll make it as painless as I can. Ok?”

I shuffled my feet. “…ok…..”

“Come on. Lay down on the bed for me.”

I did so, and he took off my diaper. After wiping me dry and patting me down, he took off my cage. “Were gonna leave this off for a few hours, but I warn you. If I catch you doing anything naughty, then spankings will be the least if your worries. Understand?”

“Yes sir.” I was being honest. I had no intention of playing with myself, despite my growing horniness at the situation. He left the room, returning shortly with what looked like a box of waxing strips and another bottle of Nair hair removal, as well as other various supplies. I’d tried them both in the past, never really knowing what I was doing. He set them down, opening everything up as he said “Well start with the worst spots first. Get them out if the way. Then we’ll do your legs so you can rest.”

I nodded my affirmation, knowing I was in for some pain. I’d tried one was strip before. One. After that, I couldn’t go through with it. But knowing James…..I knew he would.

He laid a hot wet washcloth across my pubic hairs, let that sit for a few minutes, dried me off and got the first wax strip ready. He gently pressed it against my skin, holding it at the ready as he said “Here we go…brace yourself.”

RRRRIP.

Ow ow ow OW OW OW was all I could think as I gasped in pain, recoiling from his hands as best I could while he held me down.

“FUUUCK” was all I could manage.

“Now now….usually I’d tell you to watch that language, but because of the situation…..I’m allowing it. I’m not going to stop….best to get it over with.”

True to his word, he kept on. Strip after strip, rip after rip, my hair’s were pulled from my groin until barely any we’re left. What WAS left got shaven off with a razor and cream. After that, he moved to my legs, letting my privates alone. Nair cream time. He spread it on as the instructions said to, setting a timer on his phone.

“So….”he asked me. “How did you meet Annie? What draws you two together?”

I felt embarrassed at the moment. Surely this wasn’t the time? “We met on an app…about a game. Like a fan made app. We were roleplaying as the characters.”

“Yes?” he edged me on, now putting some cream on my armpits.

“Well……I liked her attention to detail at first….it made our story more immersive. After our story was done, we just kept talking. I guess I fell in love with her heart. And then her mind. She’s kind, and caring, and tries to help others before herself.” I chuckled “Modt times that means she forgets about herself. So I try to help her too!”

He nodded, checking the patches of cream with a small scrapper to see how well it was working. Satisfied, he continued. “Soundd like mommy material to me.”

I looked at him, all somber. “Yeah….she really could be. But she’s not really into it. She supports me! Big time! And she knows about my fantasies and stuff…but she’s never made an attempt to join, or roleplay with me.”

He shrugged. “She might be scared to. I’ve heard you’ve had some bad times with this side of yourself in the past. Maybe she just doesn’t want to mess it up.”

“Yeah ….I have had some bad times. You could be right.”

 He began wiping off the cream.

“Not that she could mess it up….I’m not hard to deal with. Just…acknowledge me. Call me cute. Pat my butt. Tuck me in…..that’s all I really need. Nothing else.”

“Fate is a mysterious force. Who knows what’s in store?”

He finished wiping away all the cream, and I’m moments I watched my 26 year old body being turned into that of a smooth baby boys…..with a few stretch marks included. Bleh on those.

“There! All done. I’m not going to rediapered you, not yet, but I know you have some pullups you can wear until I do. So put one of those on while I work on this cage of yours.”

“Ok! I’ll just okay some more Minecraft.”

“Good boy. Keep drinking. The more you drink, the more you pee. The more you pee and just go whenever, the weaker and smaller your bladder will get. And that’s the goal!” he took the cage and supplies, walking out if the room.

I stood there in only my shirt, examining myself. Smooth as could be….but my skin was turning red from all the agravation. I’d let James worry about that, taking one of the large pullups I had from the closest and slipping it on. It slid up so easily! Small hips  are a blessing when it comes to these things. And with that, I went back to my game.

About an hour passed before James returned. By now, I had finished my fourth bottle of the day (we switched it to Apple juice when we got home), and had already wet my pullups.

“Ok! I think I might have done something here.” He said. “Ive adjusted some things, made other things more secure, and hopefully….it’ll do the job.”

He felt my wet pullup, and I gasped a little from the attention. “Looks like I came at a good time. Let’s get your security back in place.”

“…fiiiine…..”

I was placed back on the bed and the pullup removed. “No buts. That’s the deal for living here. Hmm….now that’s a problem.”

He was referring to my hardened dick. “I know a sure fire way to get him back in his place….two actually. One you won’t like. The other ILL like a lot more. Pick.”

I was curious….big mistake.

“The first one?”

He gave me a sly smile. “Trying to be a big man huh? Well see.”

He left, and returned shorty with what look like a wet bulgy rag. He then wrapped it around my dick.

A wet rag? What was that going to—OH SHIT…IT WAS FREEZING! I squirmed in place, but his hands held me down.

“This is what you asked for….just give it a minute, it’ll be over soon.”

I whimpered, wanting it off, but he remained firm. It was working though, the blood receeding from my penis and causing it to drop in his hand. Once it was small enough, he quickly went about replacing the cage.

A minute later, I was back in chastity.

“I have to say, you look much more sexy like this! Smooth as a baby, locked up snug, and boy does that boy pussy look clean as a whistle. But just as your not having any playtime, neither am I. I’m saving that for next weekend!” he got my new diaper ready as he talked.

“Whats next weekend? Should I be worried?”

“Oh heavens no! You wanted to train yourself to cum like a sissy boy, or girl, and the best way to do that is to let your prostate become more sensitive over the week. On Saturday, we’re going to see if it’s ready to pop! If it doesn’t, then we try again the next Saturday. Rinse and repeat.”

Oh boy. That meant I could potentially be going without cumming for a long time….very disconcerting. But I’d come to trust James, both from the time we’d spent talking over the phone and  our time spent together in person. So I only nodded, doing my best to enjoy the sensation of being diapered by my daddy.

“I’d like to say, your tasks for the day are NEARLY done and over with! I want to go over your finances with you, and after that we’re good to go and you’ll have the rest of the evening to play before bedtime.” He checked his imaginary watch. “Which is in about 3 hours. So let’s get some food and do our business.”

“Yes! Food!” I was a hungry boy.

 

Ten minutes later we were in the kitchen, making some food. All the while, James was telling me how he was going to take care of my debts and finances. He was going to use his savings to pay off my debts, then use my cars title for a loan. The loan itself would go to supplies for me, diapers, clothes, and other odds and ends. My paycheck would be used to pay off that loan and to pay him back, as well as for groceries. All in all, it didn’t seem like a bad idea. Sure I wouldn’t have any control over my own money, but when everything is being handed to you anyway, who cares? I certainly didn’t

We ate our yummy supper, my bottle filled again, out away iur dishes and then I went back to my game. I had wet my diaper twice again by this time, and I knew with certainty that my pee had to be crystal clear with all this liquid I was drinking. Two hours later, James came in for my bedtime.

“Bedtime sweetheart. Tell your friends it’s time for a change and nite nites!”

I giggled. “Will do.” I sent what he said, my friends all said goodnight, and I put the computer to sleep. Hopped up onto my bed and got myself ready for the change. James got the supplies and changed me, but not before he spent a moment rubbing my tummy and asking.

“Did you have a fun day?”

“Yeah…..I really did!, The morning was fun, the middle bleh, the evening great! Waxing hurt though….”

“I know it did …we won’t have to do that very often though. I’m going to get you one of those hair removal things I’ve seen advertised. See how that works.”

He finished my change and patted my butt.

“But now it’s sleepy time. Work tomorrow!”

“I know…….”

He pulled me into his lap, giving me a hug and rubbing my butt and back. “I know, baby boy, I know….but you’ll come home and have a good time again! Just stay strong for your papa.”

“Ok…..I seepy….” And I was too.

He laid me down on the bedtime, making sure Theese was tucked in beside me, and kissing my head again. “Goodnight my boy.”

I hesitated a moment….and said.

“Nighty night Daddy.”

 

He smiled, a big proud smile, said nothing and turned off the light.

And  then there was darkness…..

 

I wish I could say it was an easy sleep. But sometime in the night, awoke to a rather uncomfortable feeling. My dick was trying to get hard, unable to in it’s cage, but trying nonetheless. I shifted around, trying to think boring thoughts, begging my pain to end…and thankfully it did. It took awhile, but it receded back to it’s sleeping form, giving me the blissful comfort once again. I had to pee anyway, so I let it out, and settled in to go back to sleep…..

 

“Hey….time to wake up, little one.” I felt Jamess hand gently stirring me awake, and I blinked my tired eyes up at him.

“Don’t wanna…” I said sleepily.

“I know you don’t, but you have to buddy. And I want to go to sleep!” he chuckled. He had stayed up all night just to wake me up? I felt guilty….

“Here. I made you some coffee. You drink that while I get you changed. Do you have to go anymore?”

Anymore? Oh right, I’d already wet myself last night. I gave a push to get any left overs out, and sure enough I filled my diaper again. His hand was laid against the front of it, and he smiled as he felt the warmth spread beneath his hand.

“Good boy. Drink this.” He handed me a sippy cup full of coffee, and I happily began drinking it. He got to work changing me, but I was too sleepy to really enjoy the moment. He took no time getting me clean and rediapered, giving me a happy little padded pat on my bottom.

“Ok. Hop up and get dressed, alright? I’ll get you some food before you leave.”

“Ok…..” I made my way out of bed while he went to (I assume) the kitchen to make food. My sippy cup barely left my mouth as I out my work clothes on, onesie as well, and then my boots. I had no idea what time it was, but I was sure I was up earlier then I usually was so James could feed me. I didn’t mind too much.  I needed to eat better anyway. My job was too physical for my regular diet.

I headed downstairs, where I could smell fried eggs and potatoes cooking, and sat on the counter where I could watch. James turned around and saw me, still sipping on my coffee.

“There you are! Was worried for a moment you might have gone back to sleep!”

I shook my head no. “Gotta make dat money somehow.”

“Well said. Let’s get some nummies in your tummies and then I’ll send you off to work. Remember….no changing while your there. Your diaper can hold quite a bit, so just let it do it’s thing. Now, if you have to poo, that is the one and only time I’ll allow you to change. It’s for your health and your workmates noses health.” He chuckled at that. Haha, so funny.

“I don’t think I’ve ever had to poo while I was at work….so I don’t think that’ll be an issue.”

He started scooping the eggs and potatoes into a bowl for me. “That’s good to hear. Here you are. Eat up! Times ticking!”

I did so happily, scarfing into the food as best I could, but making sure I didn’t choke. Long story short, I soon found myself at work, hanging turkeys as I always did. I wanted to tell my friends all about my week and weekend, but…….they were too vanilla. Wouldn’t understand.

By second break I’d already wet myself twice, with several smaller wettings in between. My diaper would have been sagging at my knees if it hadn’t been for my onesie! But I followed the rules, finishing off my day with a third wetting, and headed home. I was leaking by this point, my pants and car seat soaked, when I went inside the house. I felt little, ashamed, yet strangely invigorated from the naughtiness of my situation. Which of course, meant SOMEONE wanted to play. It had been two full days now since I had cum, meaning I was horny as hell.

“James! You home??” I called into the house. A muffle voice from his bedroom replied “In here!”

I walked in there, finding him folding his clothes on the bed. I lifted my shirt to reveal my wet pants. “I leaked….I’m sorry….”

“No! Don’t be sorry, sweet cheeks, that means you obeyed the rules! Well get you changed and your clothes washed. And tomorrow we’ll had a stuffer into your diaper. That ought to help with the leaking.” He began undressing me, right then and there. His hands against my skin was making me hotter, and I moaned uncontrollably at his gentle touch. He kept at his work till I was down to my diaper though, either not noticing my lust or ignoring it. Whatever the case, I soon found myself laid on his bed with my legs up and my bottom being cleaned of all urine. My cage was keeping my penis from growing, and boy was it uncomfortable! I knew from my research that this is how it was supposed to work, as a deterrent. James finished his work with a fancy flourished toss of the wipes into my used diaper, rolling it up and tossing it into a nearby trashcan. I was now entirely naked in front of him. And I didn’t care?

“Bath time baby boy! Youz a stinky boy! Those nasty birdies making you smell like their poopoo….but we’ll show them now won’t we?”

“Yeah!” I giggled. He really is a funny guy….I liked it! He pulled me to my feet and lead me to the bathroom, we’re he began running the water for a nice hot bath. He dumped some bubble bath solution into the water, and I watched entranced as it started filling with bubblegum scented bubbles! Yay! Once it was full and read I was plopped into the water, and he added two rubber duckys and a boat into the water for me to play with. I did so happily, while his hands went to work cleaning me up. He washed my hair, my aching shoulders and back, down my tummy and then onto my groin. My dick wanted some attention too, but alas, the cage would have none of that thank you very much. I couldn’t help but squirm and giggle when he got to my feet….I’m still ticklish. And because of that, I think he spent more time then was needed in them.

Once I was all clean, he drained the tub, and I pretended the drain was a giant whirlpool about to suck my duckies and ship away into the depths! James got a kick out of that, so of course I milked it. All the water gone, I was stood up and dried off with a cute foxy towel! Foxes! Perfect! I have to mention, at this point I’m pretty exhausted from work, so my little side was much closer to the surface. I always get little when I’m tired.

I was placed on the bed and rediapered, the powder smelling so good and helped to make me more comfortable in my headspace. I was in bliss, happy and tired from all the attention I was getting.

“There we are….a clean baby, ready for nummies and bed! How you feeling precious?”

I sighed happily. “I feel….good. Really good!”

He rubbed my tummy. “Abd how’s the cage feeling? Any pain or pinching?”

I thought about it. “No…not really. It gets tough when I try to get hard…but I know that’s normal. It IS making me really horny though….”

“How do you think I feel? I have to see your cute little bottom all smooth and clean, and I want to take it for my own every time I change you! But you have a training schedule now, so Im not allowed to. Just like your not allowed to play with yourself!” he blew a raspberry on my stomach, and it took all I had to not kick him in the face as I squirmed and laughed. Huh….I hadn’t thought about that. Daddy or not, he was still a man with a sexual drive….and to have me at his mercy must be driving him crazy! He certainly had better control then I did….

Before long we were in the kitchen, me only wearing a t-shirt and fuzzy socks. He handed me a sippy cup, saying. “This is a protein shake. As well as a long acting laxative. It’ll do it’s job while you sleep, and you should find the need to poo either once you wake up or during sleep. It’ll help get your body on a routine. Your daily enemas won’t be needed now that your in your cage, and the only time you’ll need one is on Saturday. So drink up!”

“Ok!” a protein shake huh? And laxative? Both will be helpful, I was sure of it. So I drank up while he made food. I loved his cooking…so much better then mine!

After food and my shake, we snuggled in to watch an episode of Stranger Things, me snuggled against his chest with his arm around me. After all the liquids I have been drinking, I had wet the new diaper twice before he said “And now it’s time for bed, baby boy. Big day tomorrow!”

I didn’t want to….I was too comfy. So I didn’t move. Not like that stopped him or anything, as his strong arms lifted me up and carried me to my room. I was changed once more, the shirt removed, and then tucked into bed with a kiss on both my head and Theeses. Theese liked that for sure! I did too of course.

“Goodnight sweetheart. And sweet dreams!”

I smiled at him sleepily. “Goo’night daddy~. I see you soon!”

His smile at my words warmed my heart, and it didn’t take long before I was asleep and dreaming of the days to come.

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