Cute sissy boy

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, possible penectomy/castration (haven’t decided yet) spanking, alcohol drinking, and forced incontinence. 

You do NOT have my permission to take my story, but i wholeheartedly encourage you to share it with others! Enjoy!)

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. The idea of being called litte boy, baby boy, and above all, CUTE, are my dreams come true……I'm a bit of a sissy boy i might add. I wish i had a smaller dick then what i have right now, and though ive tried many times with chastity....no go. But diapers make me feel like the cutest and littlest baby of all.

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 love 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 closet 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.”

(Id like to add that he didnt just spank me out of the blue. We had talked about possible punishment scenarios before hand over the phone, and i had agreed to give it a try! Everything in here is consensual. Promise!)

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 pills 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. “You 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 9 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 ago 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, I'd 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 hole, 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 loving 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.

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

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

Showers/baths every day. 

Enemas daily during shower time.

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

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

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

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.

“Your 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 pee 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, removed the rather snug butt plug, 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 immediantly. 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, using all the smallest parts 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 and I 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’s all 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.