Becoming a Sissy Baby Boy – Chapter Six
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….”
The End of Becoming a Sissy Baby Boy – Chapter Six.
The story originally came from: https://www.dailydiapers.com/content/stories.html
If you want to read more stories about ABDL boys you can find a list here: Diaper Boys – Index