Becoming a Sissy Baby Boy – 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…..
The End of Becoming a Sissy Baby Boy – Chapter One.
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