What Happens to Naughty Little Boys

Chapter 1
Jesse

“What Happens to Naughty Little Boys”

-An AR fic by Crash Ichimonji

Note: Both main characters listed here are fictitious versions of real-life people in my life.

They say internet relationships are unhealthy, and that meeting one of those online friends is a risky endeavor: for two reasons, mainly. Firstly, your ?friend’ may actually be a stalking pervert out to knock you out, have their way with you, and then sell your kidneys on the black market. The second, and by far most important reason, is that your friend who you thought was some attractive man/woman may end up being some ugly person with a pasty and flabby complexion.

But, sometimes we get lucky...

My name is Jesse, just Jesse. I don’t trust you people enough to tell you my last name, or the last name of my friend either, so bear with me. I’m a 20 year-old guy who is a first-year freshman at my local community college, I live at home with my mother and high school senior brother, I have a job at a nearby hardware store, and I’ve been single most of my life. Meeting women online as friends is rather easy for me, as I belong to an adult role-playing forum site that has quite a few interesting ladies of different ages (all legal).

One of my friends on this site is a young woman (well, she’s 4 years my senior) named Victoria. From the numerous instant message chats we’ve had, I know quite a few things about her. Firstly, she has dark hair and skin since she’s half-Hispanic, she’s a history major in a university a few hundred miles south of where I live, and she has quite a domineering personality, which makes her rather fun to talk to. We really enjoy each other’s company online whether it’s role-playing or just talking, to the point that I refer to her as my big sister I never had.

As it happened, I was going to head down to her home town for a convention for anime fans like ourselves, so we arranged a meeting-day one day before the con would start. The place: her apartment just a few hundred yards from her college campus. The time: noon.

It was already 1:30 in the afternoon when I finally made it to her home, so needless to say, I was feeling really stupid for being late from making a wrong turn three or so miles back and having to find my way back to where I needed to be originally. I was clad in my black T-shirt, urban camouflage pants, and my black steel-toed boots with my long brown hair in a ponytail in the back. Hell, I even shaved off all of my facial hair to look presentable to my friend as I straightened myself out in front of her home’s door, only to have her open it just as I was about to knock on it.

I was greeted by a young woman a few years older than I was (as well as an inch taller), her body well-toned and shaped. Her hair was cropped short and blacker than coal and her skin was a healthy...ah, hell, sexy shade of bronze. Wearing a tight button-up white T-shirt and hip-hugging denim pants, she was undoubtedly the sexiest woman I had ever seen.

I gulped as I tried to say something to my friend, but then she frowned and closed the door on me. I stood there for a few moments, wondering what to do next, but ended up knocking again, asking,

“Um...Are you Victoria? Because I’m Jesse.”

Her door opened up again, this time she wore an evil grin as she yanked me inside her cozy pad and locked the door behind her. I turned to face her, but was confronted with a tight hug.

“Aaawww....You’re even cuter than I imagined!” she laughed with her mature voice. She finally let go of me and studied me with a grin. I’ve never been the bravest of guys when it came to dealing with women, so I simply stood still as she looked me over. I jumped a little as she smacked my rear hard saying, “You are SO late, you know. Bad boy!” She giggled.

“Heh, sorry, sis,” I laughed back.

“Well, I hope you’re not disappointed with my appearance, because I’m not with yours,” she smiled as she posed sexily before me.

“Not at all, Vicki,” I smiled.

“Good, ?cause I’d have to kill you if you were,” she grinned. Most people would be creeped out if someone said that to them, but since I knew this was Victoria’s sort of personality, it didn’t bother me at all.

“So, nice place you got here,” I said as I looked around her living room and its basic necessities: a couch, a TV, and a coffee table with a couple of books on it. One of the books was leather-bound and displayed writing in golden Gothic text, with the words ?Enchantments for the Promising’ written in Latin (I took 4 years of the language in high school).

“Yeah, it’s not too bad here,” Victoria smiled as she grabbed my arm and gave me the grand tour of her little bachelorette pad. First came the kitchen with all its humble qualities, then her bathroom down the hall from her living room, and then to her bedroom, complete with a queen-sized mattress on the ground.

“Bet it’s comfy sleeping there,” I laughed as I walked up to the bed and felt the silken sheets.

“Care to see for yourself?” my friend asked as she walked up behind me and slid her hand down my stomach to my crotch.

“Um...Well, not really...” I flushed as I tried to get out of her grip, but all that did was make me turn to face her. Her face was almost in line with mine, and had a luring and seductive glow to it. Before I could react, our lips were locked in a tight embrace, my first true kiss. I wanted to pull away, but as I tried, her hands held me tighter to her body, her B cup breasts mashed against my chest and her hands reaching up into my shirt.

“Mmm!” I squirmed, but soon gave in as a soft, hot and moist object invaded my mouth, lapping at my inner lips and tongue. Electricity sparked up my spine as I pressed my tongue to hers and moved my hands across her firm and toned back. We finally broke our kiss to breath, my heart in my throat now in excitement.

“C’mon now, Jesse,” Victoria purred as she pushed me unto her bed and stepped back. “I know this is what you’ve wanted for so long,” she winked as she danced and swayed while taking off her buttoned-up top, one button at a time.

“Well...Yeah...” I blushed in embarrassment as I felt my member rise against my cotton camo pants. “But, I mean, we don’t have to have sex or anything, right? I like you, but I think we should just stay friends, right?”

“Aaaawww...” she cooed as she unfastened the last button and let her shirt drop to the ground, revealing her perky breasts without a bra. “Is little Jesse afraid to pop his cherry? Hehehehehe!” she giggled as she came up to me and tore my shirt off in a quick lift, then pressing her bare upper torso to mine while we kissed again. Our tongues danced together as we continually osculated to one another. Her hands would rub my chest and belly while mine would attend her wonderful bosom, her breasts just the right size and tenderness for me to massage.

“Ooh...You certainly changed your mind...” Victoria gasped as my hands continued to squeeze and grope her slightly swelling chest. I then trailed my kissing to her cheek and then to her jaw-line, slowly moving my lips to her breasts to suckle her now hardened nipples. The salty yet sweet taste of her skin was a major turn on for me while I continued to suck and lightly nibble, occasionally making my partner moan. Remembering good sexual etiquette, I brought my hand over to her lonely breast and began to rub it and pay equal attention to it. I was shocked as I felt her soft hand slip into my pants and rub against my fully erect cock, stroking it up and down with taunting gentleness that was driving me wilder with lust.

“Two can play at that...” I grinned as I brought my free hand into her pants and underneath her silken panties, rubbing her shaved pubic region and inner thighs. After almost a solid minute of fondling each other’s groins, we finally parted to undress completely. When I turned to my friend, she was already crawling toward me with an almost feral intensity in her eyes. I gulped as she bent her head to my stiff member and began to tease me with a repetition of licks and lip-smacks. I was a total virgin, so I never knew what to expect with any stimulation by anything other than my hand.

“Ah!” I cried as my loins burned and shivered at once from all the oral work of my partner. It wasn’t taking too long for pressure to build up in me, and Victoria knew it too, which is why she suddenly stopped just as I was about to cum. I had to catch my breath for a few moments before I could do anything else. “Why...did you...stop?” I asked in between breaths.

“You’re a virgin, remember?” she cooed as she laid back and gave me a good view of her snatch, now dripping wet. “You told me once online that you’re good for one round every hour, right? So, I figured I’d be merciful this one time and let you shoot your load in me...rather than ON me...Heh heh heh heh...”

“Thanks, sis,” I sighed as I realized that I had to return the favor to her (and then some) as I crawled over to her open pussy, hesitantly putting my face to it and lapping at it. Her flavor was certainly unique (but then again, I hadn’t eaten pussy before); it was a mix of a salty and musky flavor with a pinch of sweetness in a tart way. As I began to mouth her labia and inner folds, I suddenly felt her hand force my face deeper into her crotch, vaginal juices smearing across my face.

“Do the licks in long strokes, now,” she commanded to me. “And make sure you pay attention to as much of everywhere as you can, especially my clit.”

“Mm-hm...” I managed to mumble as I did as I was instructed. Soon, I felt her toned thighs clamp around my head and neck, pinning me to her indefinitely, but still allowing me to hear her sigh and even moan from my stimulating. In no time at all, I managed to get the hang of things and had her pussy practically gushing with her nectar. In between licks, I would hum into her womanhood, doing my best to replicate a vibrator, which turned out to give her a little extra pleasure, until she finally climaxed with a slight splash into my face, her legs letting me go to catch my breath.

We both laid there for several seconds, panting from our little oral session. As I wiped my partner’s juices off my face, I suddenly saw her climb above me, ready to straddle me by the cock.

“I think it’s only fair that I do the work this time. That way your memory of losing your virginity can be a good memory,” Victoria winked at me as she slowly slid my member into her, her body quivering in response. Victoria told me she tore her hymen years ago with adult toys, but had never had a man in her before. Her snatch was tighter than I imagined it would be; not to say that I was expecting her to be loose, mind you. Her warm and constricting folds were enough to get me panting already, but she still proceeded with her service to me.

Slowly, she bounced up and down on my shaft, taking her time to drag out the sensations for both of us with each movement.

“Vicki...Ahh...!” I breathed. “Did you...take anything...so I don’t...get you pregnant...?”

“Mm...Yeah...Of course...” she breathed in between bounces. “You’re cute...Ah....But I doubt you want to be a papa at your age,” she grinned. “Besides...you don’t want to get your ?big sister’ pregnant, do you? What would mommy think?” she giggled in between sighs.

“Thanks...” For the next five or so minutes, I was tantalized to the brink of sexual insanity as my partner milked me of my erogenous bliss as much as she could, sharing in the enthralling sensations at the same time. Soon, it was too much for me to take as I gritted my teeth and breathed hoarsely. “Gonna cum!” I cried.

“Hold on...! I’m almost there...!” Victoria whined. “Oh yes!” we both yelled at once as we had managed to synchronize our climaxes. For me, it was the greatest and most satisfying sensation of my life as I tensed and jerked in place from the wonderful electric heat centering at my loins. After my last few aftershocks waned, and Vicki finally slipping into her afterglow, the two of us managed to separate and get under the satin sheets to cuddle.

“Wow...That was indescribable...” I sighed.

“You didn’t do too bad there, Jess-o,” my friend said as she stroked my long and curly brown hair. “You need more experience, grant it, but all in all you managed to give someone as experienced as me a good show,” she then kissed my forehead as we snuggled closer, our legs intertwining. This was something just as wonderful as the sex: embracing one another as more than friends now. Our sweaty and hot bodies clasping one another was blissful in its own right for me, enough to put me at total ease. I shut my eyes, hoping I could stay like this with her forever, until a stream of air blew into my ear to make me shiver with delight.

“Hehehehe!” Victoria laughed as she brought my face to look into hers. “So, do you still think of me as your big sister, hm?”

I couldn’t help but blush heavily from her words. “Yeah, I still do, Vicki.”

“Well, what if I told you that you could be my little brother for a day? You think you’d want to try it out?” she grinned.

“Sure, of course,” I laughed. I had so many kinky thoughts already formulating about what we could do later for role-playing and such.

“Alright then. How tired are you, sweety?” she asked as she stroked my hair again.

“Pretty tired, I’d say,” I answered.

“Alrighty then. We’ll get some sleep for now, but tomorrow you get to be my little brother, ok?” she asked with an insatiable grin.

“Ok then. G’night, sis,” I said as I pecked her lips.

“G’night Jess-o,” she smiled as we closed our eyes and slipped into the peace and tranquility of slumber.

My time asleep went almost completely undisturbed. The one thing that sort of woke me up was Victoria leaving the bed for a moment, probably to go to the bathroom or something, but I didn’t pay any attention as I went back to sleep. The next morning, I awoke to a glorious sunrise of cascading colors, totally recharged with energy to boot. My love-making from yesterday disorientated me a bit still, as when I got out of bed, everything felt a bit awkward in perspective, like everything got a little bigger. I didn’t pay it any notice as I decided to see if Vicki was up. As I looked over to her side of the bed, I saw that she was, and the smell of eggs and toast warmed my taste-buds and got me in a good mood.

As I proceeded to the living room, I passed by a mirror in the bedroom...only to jump right back in front of it to see if my eyes were out of focus or something. I looked in the mirror to see a boy with neck-length hair and a scrawny body, having little muscle-tone or even pubic hair. I couldn’t make a sound for a few seconds, but when I did, it came out in a tenor voice.

“What the hell!?”

I heard footsteps my way, with Victoria coming into the room clad in a large T-shirt with a spatula in one hand.

“What happened to me?!” I panicked as I looked at my friend, hoping she could help out some way...but an almost too pleasant smile crept to her face as she walked up to my naked, prepubescent body and gave me a hug, my head now smushed into her breasts from my lack of height.

“There there, little brother...” she cooed as she released me and ruffled my hair (much to my disliking).

“What did you do to me!? “ I demanded with a frown.

“Isn’t it obvious? I made you into my little brother, just like you wanted.”

“This wasn’t what I had in mind, dammit!”

“Goodness, such vulgar language for a twelve year-old. Watch you mouth, mister,” she waved her finger at me like she really WAS my sister!

“Can it, Vicki,” I humphed with my annoyingly high voice. “Change me back to being 20...now.”

“Nope.”

“Why not?”

“Because the spell only wears off after 24 hours. So, until tomorrow morning, you’ll stay this age at the maximum, got it?”

“What do you mean by ?maximum’?” I eyed her suspiciously, remembering age regression stories I had read online. “How young am I going to get?”

“Depends on how good of a boy you are today, and how well you behave.”

“What?! You sick, controlling bitch!” I spat in anger.

“Excuse me?! What did I say about using adult language, LITTLE brother?” she scowled at me.

“Bite me, you-” but before I could finish, I noticed that Victoria grew taller above me...or rather, I grew shorter! I sunk down about two or three more inches, my body no longer having any noticeable muscle masses, and my penis shriveling shorter while my balls started to go back into my body. “Oh God!” I screamed in my higher voice.

“See, I warned you, Jesse. You should listen to your big sister more often,” she folded her arms across her chest as she looked down on me. “For every time you’re a naughty little boy, you’ll get two years younger.”

“Is there a stopping age?” I asked shakily.

“I actually don’t know,” she laughed. “So I think you should be on your best behavior today, right?” she then grinned at me.

“Okay...” I pouted.

“Now, I think you need to be punished for calling your big sister, who loves you very much, such mean things,” she said with an evil face.

“Wait, what do you-” I asked, but soon she grabbed me by my skinny arm and pulled me to the bed, where she sat on the edge and propped my smaller, weaker form atop her knees. “Wait, no! Look, I’m sorry, Vicki!” I tried to negotiate with her.

“I don’t think you mean it, little Jesse. So I’m going to show you what also happens when you disobey your big sister!” And with a loud and painful smack, she brought her flat palm against my soft and rounded tush.

“Ah! I’m sorry!” I cried out.

“Sorry what?”

-SMACK!-

“AH! I’m sorry, sis!” My eyes began tearing.

“I don’t think you mean it!”

-SMACK!-

“Please! Stop, sis!”

“Tell me that you’re a naughty boy and that you’re sorry for being a little brat!”

“No! You were the one who-”

-SMACK!-

“AH! Ok! Ok! I’m sorry, sis!” I cried like the child I was. “I’m sorry for being a naughty little brat! Please! I’m so sorry, sis!”

I expected another slap, but instead, my new big sister picked me up and sat me on her lap, holding me close to her as I cried into her shirt’s shoulder.

“There there, little brother,” she cooed to me as she rubbed my back soothingly. “It’s going to be alright now. I did that because you need to learn to be a good boy, alright?”

“Yes, Vicki...” I sniffed.

“Good, now, to make you feel better, I made toast and eggs in the kitchen. So, let me get you a night-shirt and some undies to wear, and then you can come into the kitchen to eat breakfast. How’s that sound?”

“Alright...” I sighed as I wiped away my remaining tears. Apparently, Victoria had this planned from the beginning. I knew that because she pulled out a T-shirt too big for me to wear like a normal shirt, and a pair of child-sized briefs with...ugh...Pokemon on them...

“Here you go, little brother,” she smiled as she presented me with my new attire. I reluctantly put the clothing on, being reminded of how small I was with the night-shirt trailing down to my knees, and so I followed my big sister to her kitchen table, taking my seat.

“Thank you, sis,” I said meekly as I sat on my legs to stick up a high enough to eat at the table better.

“Aw, no problem, Jess-o,” my friend smiled back at me as she brought over a plate of two slices of toast with butter in the middle, and a fully-cooked sunny-side up egg. “Now, eat up, because we’ve got a big day ahead of us at the convention.”

“What?” I asked as I began to cut up my egg. “I can’t go like this. I don’t have any clothes that’ll fit me anymore.”

“You don’t, but I do,” my sister grinned as she turned off the stove and headed to her room for a bit. I used that time to eat my breakfast, until she came out with a blue and yellow shirt, khaki shorts, and a pair of little sneakers. “See? I thought ahead!” she chirped as she sat the clothes on her couch and headed over to the kitchen, pouring herself a cup of coffee.

“Can I have some?” I asked as I began eating my toast.

“No, silly,” she ruffled my hair again. “Coffee is for grown-ups.”

“But I am a grown-up!” I responded.

“Check in the mirror lately, little bro?” she smirked at me.

“Uh-! You know what I mean, Vicki.”

“Oh, I see,” she winked at me. “You’re REALLY a 20 year-old in the body of a 10 year-old, I gotcha. Well, I’ll play pretend with you today, little brother, but you still gotta be on your best behavior if you’re gonna want me to get you anything at the convention, ok?”

“Can’t I use my own money?”

“Silly, you’re too young to have a wallet with such big dollar bills in it, so until you grow up, I’m keeping it safe and hidden.”

“Grr....” I sneered as I finished with my plate. “I’m done...”

“Alrighty then,” Victoria smiled as she took my plate and washed it in her sink. “Now, go take a shower to wash off all that stinkiness from yesterday, little man.”

“Alright, sis,” I said as I grabbed my new clothes and headed to the bathroom. There on the counter was a towel and a washcloth, thus providing more evidence that Victoria had thought WAY ahead of time for today. Taking off my current clothes and waiting until the shower warmed up, I grabbed the washcloth and headed into the shower to start washing myself. It was then that I got a better understanding of how I looked right then. My form was lean, though I did have baby fat on me still, making my tummy a little rounded. Then there was my hair. It was a little more than upper-neck length now, and was more like duck-fluff instead of the greasy texture it was for me as an adult. As I looked at my penis, I noted how small and shriveled it was, and wondered if I could even get a hard-on with it at this age, let alone masturbate successfully.

I finished washing my body and hair quickly, and exited the shower to dry off and dress. As I put on the clothes, I found that the shirt had a large image of Pikachu on it, utterly disgusting me to no end. But then again, I couldn’t afford to complain lest I wanted to be any smaller.

“Ah you all dressed in there, Jess-o?” I heard Victoria call from the outside of the door.

“Yeah!” I called back to her.

“Good then,” she said as she opened the door to look at me. “Aw, aren’t you just precious...” she smiled as she looked at me with a lovey-dovey face.

“I can’t believe you got me a Pikachu shirt...” I mumbled.

“It looks good on you, little bro. Besides, you’re coming to the convention as my little brother, so you need to be wearing something anime related, got it?”

“Yeah, yeah...I get it...” I sighed as I headed out of the bathroom for my sister to shower up too. I waited on her couch in the living room when a thought came to my head: was there another reason for Victoria regressing me like this? I decided that I would ask her once she came out of the shower dressed. However, she was barely even clothed when she finally came out of the bathroom, clad only in an auburn towel as she turned to face me with a sick grin on her face.

“Oh, Jesse,” she called as she walked up to me, her hips swaying side to side in a provocative manner.

“Um, shouldn’t you be getting...Um...Dressed?” I gulped as she stood in front of me, posing erotically with her towel being the only cover over her.

“Well of course, sweety,” she said as she bent forward to me, her cleavage in plain sight. “But I was wondering...”

“Um...Yeah?”

“Were you having dirty thoughts about your big sister while she was taking a hot shower?”

“No...” I shook my head.

“You mean you weren’t even thinking about my sleek tan body, shining with clear water dripping down my curvaceous form in the slightest bit?”

“No...” I shook my head again, fearing she was going to find a way to make me regress more.

“Really?”

“Really...”

“Then...How come your little wee-wee is all happy right now?” she purred as she patted my crotch. I hadn’t even noticed that I was getting a hard-on right until I looked down and saw a small protrusion from my pants.

“It’s not my fault!” I panicked, waiting for my body to shrink again, but...nothing happened.

“Aaww...Little Jesse’s first erection. I suppose you are a big boy in some respects. Hehehehehehe!” she giggled as she let go of my member and walked to her room to dress.

I said a few choice words about my new sister mentally, lest she hear me and make me regress. When Victoria finally came out all dressed, I was a little surprised at her attire. She wore a leather jacket over a white strapless one-piece bathing suit, fingerless gloves, thigh-high white stockings, and combat boots. To top it off, she had a hip-holster with a plastic gun in it.

“Sir!” she saluted and clicked her heels. “Major Motoko Kusanagi reporting for duty! Proceeding to escort young Jesse to the otaku conference!” she reported as if I was her superior.

“Wow...!” I gawked. “You REALLY managed to pull it off as the Major, sis,” I awed as I jumped off the couch and walked up to her. She even styled her short hair to look like Motoko’s too!

“Shall we go, little brother?” she smiled at me.

“Yeah!” I cheered as we headed out to her apartment’s parking area and took my car since Vicki apparently doesn’t have a car or need one for a bit since she’s within walking distance of her university, and, the city bus stops near her home too. The drive to the convention was only fifteen or so minutes long, yet I could feel the effects of my regression taking root in my mind.

“Are we there yet, Vicki?” I complained after about seven minutes of being in the backseat of my car.

“Have patience, kiddo,” she glanced at me through the rear-view mirror. “Would you like me to turn the radio on so you don’t get bored?”

“Sure,” I nodded as she switched on my vintage 1997 radio, the local alternative rock station playing. “Ah, that’s convenient,” I sighed as I listened to the heavy guitar and vocal sounds strum from my car’s speakers.

“99X? Children don’t need to be listening to this kind of music,” sis remarked as she switched the channel to the Disney kids’ station, which was playing a mind-numbingly mild version of an already dull pop song...Ugh...

“Hey! Change it back!”

“Nope. Sorry, bro.”

“I hate this kind of soft-core crap, and you know it, Vicki.” I fumed. “Change it back now!”

“Excuse me?” she glared at me from the mirror in the same way as...

“Oh crap!” I squeaked as I shrank in my seat a few more inches, my hair shortening a little and my body becoming that of an 8 year old.

“Still want to listen to all that adult music, young man?” I saw a glint of smug prowess as my sister turned to face me for a sec.

“No, sis...” I frowned. My clothes still fit me, they just were a little bit loose since I didn’t grow much at that age-range. “How about we just keep the radio off...”

“Ok then, LITTLE brother,” my sister smiled as we continued to drive on.

After we arrived and bought our day passes for the convention, Victoria and I made our way through the splendors of the place. Left and right were cosplayers in the most interesting of dresses and costumes, artists with the most interesting of works, videos of the most interesting ideas put into animation...

...And I was stuck holding my sister’s hand as we cruised around simply looking.

“Sis...” I whined. “Are we gonna do something or what?”

“Have patience, dear. I’m trying to find something in your age category.”

“Say what?!” I exclaimed, only to have a cold stare face me from above.

“Want to be 6?” Victoria narrowed her eyes at me.

“N-no, ma’am!” I panicked as I shut myself up instantly. We finally came to a table area with several boys playing the Yu-Gi-O card game, some my age and others as old as my sister. “You don’t mean...this...?” I asked hesitantly.

“Yeppo, little bro!” she smiled at me as she took out her wallet and bought me a starter deck. “You said you knew how to play, right?” she asked as she handed me my card pack.

“Yeah...I was only interested in the game for half a year, mind you,” I sighed as I took out the deck and looked over the cards. They were decent cards and all, but...”I feel so childish...” I sighed again.

“Oh, don’t be so grumpy,” she laughed as she nudged me to the tables to play against one of the guys there: a 14 year old boy with an obnoxious look in his eyes. “Could you be a dear and play against my little brother?” Vicki asked as I sat down in front of him.

“Sure,” he shrugged. “But he better not cry after I whoop his butt,” he grinned smugly. Ooh! If I wasn’t half his size, I’d show him who’d be crying!

“Thanks. Now Jesse,” Victoria turned to me.

“Yeah?” I looked up at her.

“Be a good boy and stay here for a bit, ok? Don’t go wandering off when this is over because I’ll be right back.” I was beginning to hate her sisterly condescendence, but I was still unable to do anything for the next 15 or so hours, so I held my tongue.

“Ok, sis...”

“Good boy. Have fun and play nice,” she smiled a she kissed my cheek in an annoying sisterly way. As she left, I was confronted with the boy’s sick grin.

“What?” I scowled at him.

“Nothing,” he laughed as we began her game. I won’t go into detail about all the game. Long story short, I lost with my novice deck, but had managed to put up a good fight. Rather than gloat about beating the snot out of an eight year old, the boy did something else.

“Hey, kid? How about I make a deal with you?” he whispered.

“Hm? What do you mean?” I asked.

“How’s about I give you two good cards from my deck if you’ll get your sister to show me her boobs in private?”

I was hardly shocked as much as I was angered. He wanted to look at my sister’s breasts just for two cards! The nerve! But then, my 8 year old mind got a devious idea...

“Ok, but I want a down-payment,” I gave him a stern face.

“What?!”

“You heard me. I want some insurance that you’re not going to get what you want and then jip me at the last second.”

“You know,” he sighed as he handed me the first rare card, its shiny metallic foil glimmering. “For a kid, you certainly know how to play like an adult in deals.”

“You have no idea...” I whispered to myself. My plan worked. I managed to spot Victoria just a few feet from our table, talking to a fellow cosplayer. “Hey, sis?” I tugged on her jacket.

“Hm? Oh, Jesse! Did you have fun, sweety?” she asked with that damn sisterly tone.

“Actually, that kid I played made a deal with me,” I motioned her to bend onto her knees so I could whisper to her.

“What?”

“He said he’d give me two rare cards if you’d show him your breasts somewhere private. But I asked for one of the cards as a down payment, and now I’ll keep it since I know you won’t do such a thing. Heh heh...Sucker,” I snickered, my mind reverting to its devious state of when I was this age.

I was expecting sis to be proud of me for taking advantage of the hormone-crazed teen, but instead, I felt her pinch my arm sharply with her nails, my body flinching in excruciating pain.

“AH! Ow, quit!” I squealed.

“Shame on you, Jesse!” Victoria scolded me as she smacked my rear hard, making me yelp and begin to tear up. “I thought I raised you better than to be such a lying and evil young man!”

“But you didn’t raise me!” I tried to pull away, but soon felt myself shrink again. Luckily, no one noticed as I grew small enough that my clothes actually began to get baggy on me.

“I’m going to have to spank you when we get home, Jesse. But first, we’re going to go over to that kid and you’re going to give him his card back and apologize, alright?” my sister frowned at me as she led me back to the table to speak with the boy.

“So, is it a yes?” the boy gulped with excitement.

“No,” Vicki shook her head. However, she walked up to the boy and gave him a kiss on his lips, smiling. “Try getting to kissing the girl before you even think about looking at her assets next time,” she winked to him. “Now, I think you owe this young man an apology, Jesse,” she frowned back at me.

“Alright...” I sighed as I handed the boy his card back. “I’m sorry. I was going to take the card for myself...” I mumbled with sorrow.

“Hmph! I guess your sister got all the nice genes,” he scoffed as he walked away from us. We went back to being ?normal’ as Vicki pulled me by my weak arm and dragged me around some more. We visited many other booths and watched numerous movies together, though I still felt apprehensive about going back to our home....I mean, Victoria’s home. The fear of being spanked again frightened me to no end, especially with my smaller and frailer form. At around six o’clock, my sister looked down at me with a smile.

“Ok, Jesse. Time to head back home.”

“What? But I want to stay longer!” I demanded.

“Nope. Little boys need to go to bed early, and since you’re a little boy, you have to follow the rules.”

“Dammit! You must love being in your position over me!” I cursed in post-toddler rage. But just as I realized my erratic behavior...

“Wrong answer...” my big sister waved her finger at me as I shrank even more than before, my pants falling off my legs and my shoes too big to fit. My Pikachu shirt was down to my knees now, and my hair was barely at upper neck-length! I was 4 now! Once again, no one saw or at least they didn’t pay attention as sis picked me up from under my arms and carried me in my over-sized shirt to my car. After she buckled me up, we headed back home. I was so frightened to even speak with how much I had regressed in just twelve hours. I figured it would just be best to say nothing at all and just make it to bedtime. In the morning, it would all be over. I would be 20 again, and I could leave this second-childhood hell...But the traffic on the way back was horrible, and with the sun’s heat pressing down on me, I slowly gave way to sleep.

I dreamt about my big sister and me going to the park together and playing in the sand. There was a picnic basket that we ate from and we even got to run and play hide-and-seek on the playground equipment. Then, as soon as it started, my wonderful dream ended with a slight nudge on my shoulder.

“Jesse...” a young woman’s voice cooed to me softly. “Jesse...We’re home.”

“Hm...?” I slowly opened my eyes and yawned, seeing sis looking at me. It was already sunset and I was totally exhausted.

“Here, let me carry you in, honey,” she smiled so pleasantly that it made me feel so at ease. Resting in her arms as we headed upstairs, she let me down onto the ground after we made it into the apartment. I crawled up onto the couch and tried to stay awake. I knew that my shows would be coming on in a half-hour or so, so I switched on the TV.

“Uh uh uh...” Vicki informed me as she took the remote from my small hands and turned the box off. “It’s bath-time for you, mister,” she folded her arms across her chest at me.

“You mean shower-time, right?” I raised an eyebrow at her.

“No, I mean bath-time. You’re too little to take a shower.”

“I think I can still handle it. Thanks anyways,” I huffed as I slid off the couch and headed to the bathroom to turn on the shower.

“Jesse! You’re going to take a bath whether you like it or not!” she said sternly at me as she took me by my arm and propped me on her lap again.

“Wait! Vicki! Please don’t!” I screamed in terror as she pulled off my shirt and left me naked.

“You’re being bad still! So you’ll get extra punishment this time!” she yelled as she swatted my soft and rounded rear.

-SMACK!-

“Ah! Please! Stop sis!” I wailed in pain.

-SMACK!-

“I’m sorry! I’m sorry! Please stop spanking me!” I cried with a torrent of tears flowing down my chubby cheeks now.

-SMACK!-

-SMACK!-

-SMACK!-

“Waaaaaaaaaaahhhhhhhh!” I sobbed as I regressed until I was 2, my hair now shorter than it had been in many years. I felt so small and helpless as my sister then picked up my pudgy form and looked me in the eyes intently.

“Are you sorry, Jesse?” she asked.

“Yes, sissy...I’m vewy sowwy...” I sniffed with my babyish voice.

“Ok. I won’t spank you anymore tonight, I promise.”

“Thank you, sissy.”

“Good. Now, since you’re only two now, it looks like I’ll have to take a bath with you,” she smiled. And then the strangest thing happened to me. All my anger and frustration with my sister flew away. I was going to spend more time with sissy, so I didn’t feel any bad feelings anymore. She placed me on the floor in the bathroom as she stripped completely and filled the tub with steamy warm water and even added fun bath-bubbles to it!

“Yay! Funny bubbles!” I cheered as I waddled over to sissy and looked anxiously as the foam grew and became a great iceberg of soapiness in the now full tub.

“Ok, let’s get in baby brother,” she said so happily as she picked me up and sat in the tub with me sitting on her bare lap. The water was nice and warm, and my sister’s gentle arms holding me made me feel so relaxed and at peace. The bubbly froth of the tub made me so ecstatic that I couldn’t help but giggle childishly as Vicki put some of it on my head to make a large cone.

“Nice hairdo, Jess-o!” she laughed with me as I splashed a little in the tub with my little arms. It was certainly a wonderful experience to sit there in sissy’s lap, having her then pour handfuls of bathwater over my soft and tender skin, until we were both completely soaked. “Now, time for washing everywhere,” she cooed as she took out a mitten-like washcloth and began to lather it up with baby body wash, the fragrant smell comforting me further.

“Don get it in my eyes, sissy,” I requested as she began rubbing my tummy with the glove, then moving to my arms and legs.

“Ok then. Now, close your eyes and hold your breath for a bit. I need to get your face.

“Okay...” I sighed as I did as I was told. Much to my disliking, the cloth rubbed against my face and managed to get up my nose. Panicking, I tried to rub my face, but this only made it worse, and so I eventually jumped up and tried futilely to clear my face. In my scrambling in the tub, I accidentally knocked Vicki back from her seat, causing her to apparently knock her head on the bathtub faucet.

“OW!” she yelled as she quickly splashed a big handful of water at my face, clearing me of my problem. “That wasn’t too nice of you, Jesse...” she scowled as she rubbed the back of her head with ah his of pain.

“Sowwy, sissy,” I bowed my head. And then I felt myself shrink one last time. Frightened as everything became bigger around me, I fell on my butt as I lost the ability to stand. But luckily, Vicki managed to grab me and hold me in her arms as I shrank into a several month old baby. My body was very small and poorly coordinated. When I tried to speak, I found that I didn’t know how to! Everything around me frightened me, and I began to cry as infants do.

“There there, baby brother...” sissy tried to calm me down as she stepped out of the tub and dried off the both of us while she carried me still. I still cried my little eyes out as I realized my terrible position, unable to do anything but that. It was already dark out, yet the two of us were still unclothed as we went to the living room, where Victoria opened her spell book and found a page she had been looking for.

“It’s going to be ok, little Jesse,” she said in a motherly voice to me. “I know just the thing to get you at ease...” And soon she began to chant her spell in Latin. At first, I didn’t notice anything. But soon, I felt the cushioning of my sister’s bosom expand and grow to a fuller size. “I remember you used to tell me that you have a major lactation fetish. So, I think this will be your reward for making it through the day. Drink up, sweetie-pie!” she cheered to me as she directed her crimson areola to my little toothless mouth.

I took the little puffy nub of flesh and began to suckle gently, my actions rewarded by a steady stream of sweet and rich milk. It soon was my all-consuming thought as I fed from my sister to sate my hunger. I could hear her breathing increase in pace with each gumming and lapping I would give her swollen teat to feed. This was all that mattered to me: me and my sister. Just the two of us living together in such a peaceful situation. As I continued to drink the warm and delectable milk. I felt my tummy expand from the sweet fluids, until I could drink no more, turning my head away.

“Aw. All done, Jess-o?” she smiled as she stroked my thin layer of blonde hair. I then felt a churning sensation in my body, slowly expanding and making me feel quite uncomfortable! I tried to get sissy to understand what was going on, but all I could do was squirm and cry. “OH, I see.” She then propped me up to her shoulder and patted my back until the gases left my mouth.

“Urp,” I exhaled as she ceased her patting and brought me back into her arms, cradling me back and forth. Everything began to get hazy...I remember Vicki humming a nice little melody as we headed to her room and laid down on her smooth bed. As I fell asleep, the last thing I saw was sissy’s smiling face as we both went into slumber.

The next morning woke me with a start. I quickly checked my hands and loins to see if I was back to normal like Victoria had promised.

Yep.

Relieved, I looked over to my big sister and found her still asleep, but her breasts still a cup size larger than they were from yesterday afternoon. Which meant...

“Hm?” Vicki awoke sluggishly as she looked down to see me suckling her one last time. “Naughty little boy,” she giggled as we embraced one another and cuddled for a while. “So, did you enjoy being my little brother for a day?” she asked as she stroked my long brown hair again.

“Yeah...Aside from the spankings, it was kind of fun really,” I laughed.

“Well, maybe next time we’ll switch and I’ll be your little sister. Sound fair?”

“Sure,” I smiled as I checked my watch. “Well, I gotta head on back, Vicki.”

“Aaww...So soon?”

“Yeah...I have stuff to do back home tonight. I’ll see you online though,” I reassured her as I rubbed her sleek and firm back.

“Well, ok. Just be careful on the roads. I wouldn’t want my baby brother getting in an accident,” she grinned.

“Of course, sissy,” I smiled we embraced in one last kiss before I went and got dressed.

 

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