Becoming a Sissy Baby Boy – Chapter Two
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.
The End of Becoming a Sissy Baby Boy – Chapter Two.
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