Babysitting the Bully

[Wannatripbaby]

Babysitting the Bully

Author's note: all characters depicted here are 18 years old or older. Enjoy! 

 

 

   I cannot fucking believe what I'm seeing. Raine Eleanor–the bully who has been making my life hell ever since she transferred to my highschool–lying on her bed, her back towards me, wearing a DIAPER! 

   "Mommy are you home? I need a change."

   Oh my god, this is just too good! She hasn't even seen that I'm standing in her doorway. 

   "I'm really messy, can you please come change-" she finally glances over her shoulder and locks eyes with me, her face going as white as her diaper. "Wha-, Danny? What are YOU doing here, dork?" she says, quickly straightening herself up and hopping out of bed. 

   "Really? You're calling ME names when you're the one wearing a fucking diaper?" 

It probably wasn't very wise to mock her. We were alone in her house, so there'd be no witnesses if she tried to overpower me. But I was just too jazzed about seeing the highschool bully in such a compromising state. 

   To my surprise, she shrunk back a bit at that, trying, unsuccessfully, to pull her onesie–yes, she's also wearing a baby onesie–down as far as she could to conceal her somehow-more-babyish garment.

   "W-why are you in my room? What are you doing here!?" 

   "Your 'Mommy' called me here to babysit. Of course I had no idea the 'baby' I'd be 'sitting' for was you." 

   Her cheeks somehow went even more pink than they already were "You're my… Babysitter?" 

   "Yup. And believe it or not, I'm just as confused about it as you are." I had never met her mom, and I didn't advertise myself as a babysitter. I don't even know how she got my number. 

   "Well… that might be what my mom calls you, but… I'm not a baby!" 

   All it took was a subtle glance down at her waist and back up at her eyes to completely dismantle that argument. 

   "L-look, just because I'm wearing this onesie and, and this diaper, doesn't-... Okay look YOU'RE the nerd here so just shut up! And don't tell ANYONE about this!" 

   I was already reaching for my phone to snap a few pics before her tirade was even over "Keep it up and I won't have to." 

   The look of abject horror on her face was absolutely priceless. "Y-you better not! I'll beat you to a pulp you… You nerd!" 

   "Oh I'm sure you could, but then I'd have no reason NOT to spread these *adorable* photos of your diapered butt all over school." 

   That took all the fire out of her immediately. "Look, I… I won't beat you up if you promise not to show those photos, okay?" 

   I got her, and we both knew it. I was holding all the cards and all she could do now was grovel and beg for me not to ruin her life the way she'd been trying to ruin mine all year. 

   Finally, the tables had turned! 

   "This is so embarrassing," she whined. "I can't believe my mom hired you to watch over me."

   She sat back in the bed and winced, scrunching her face like she'd just licked a bowl of lemons. "Look, can you just... Do you think you could... I mean if you are my babysitter after all, would you... Change me?"

   I blinked. What did she just… "Come again?" 

   She looked down at the floor, unable to meet my gaze "Would you please change my diaper?"

   Now it was my turn to scrunch my face "Uhhhhhhhh, how about fuck no?" 

   Her head snapped back up with a pleading look in her eyes "Please! It's all mushy and it… And it feels gross…"

   I scoffed "Yeah, I'll bet it does. But after the way you've treated me at school this entire year, why should I help you?" 

   She looked back down at the floor "But I… I can't do it on my own…"  

   Part of me wanted to ask *why* a highschool senior couldn't change her own diaper, but I was too pissed at her to think that critically "You've made my life hell all year! And now that I hold power over you you're expecting ME to play nice and… and change your diaper? Fat chance, bitch." I crossed my arms "You deserve to sit in your own shit all night."

   She was silent for a bit, looking down at the floor again and twiddling her thumbs. She knew I had a point. "I'm… Look, I'll uhh… I'll stop bullying you? If you change me?" 

   I held up my phone and smirked "I'm pretty sure you'll stop bullying me regardless unless you wanna be exposed to the whole school."

   She nibbled her bottom lip "I'll umm… Sit with you on Monday? At lunch?" 

   I raised an eyebrow at her. "Bold of you to assume I'd even *want* to be associated with you at school. Especially once everyone knows you're a little poopy pants diaper baby." Yes, she was hot and I was a social outcast. But she had tormented me AND my friends. It would violate every principle I had to associate myself with her just for the status boost. What good would I have with a reputation like that, anyway?

  "Please! I'll do anything! Anything you want, just please change me?" 

   I couldn't help but laugh at her pathetic display "Well that's just too bad. I can't think of a single thing I'd want from you that would get me to change your diaper." This whole situation was getting more ridiculous by the minute. What the fuck kind of freak show did I sign up for, anyway? 

   She looked down at the floor again, no-doubt weighing her options. When she looked back up at me, she had a… Mischievous smirk on her face. 

   "I kinda have an idea."

   I eyed her skeptically "which would be…?" 

   "Come here for a second." she said, shifting off of the bed and getting down on her knees.

   This could be a trap, but at this point my curiosity was getting the better of me. I slowly approached her until I was directly in front of her, grimacing slightly as the stench from her diaper became more noticeable. Fuck, she smelled worse than a barn! "No funny business?" 

   She shakes her head "I know of a way I can get you to change my messy diaper." she runs her hands up my legs, batting her eyelashes at me seductively as she reaches for my belt buckle. 

   Fuck. I'd never been… No one has ever… This kind of thing doesn't happen outside of porn! "I-I-I ummm, w-what do you think you're doing down here?" 

   Her smirk widened as slowly unzipped my pants. "Just let me take it out, just for a second."

   I was paralyzed by her touch. A second ago I thought I held all the power. Now I was completely at her mercy as she pulled my now-hard cock out of my pants. "I uhhhhhhh, I dunno if you should be d-d-doing that."

   "What, you *don't* want me to suck your dick?" her fingers wrapped themselves around my shaft, holding me mere inches from her mouth. "I know you do."

   All it took was her tongue grazing the tip of my dick and I felt like I'd been electrocuted! "Fffffuuuucckkk…" 

   A giggle escaped her lips "I think you like that just a little bit."

   All I could do was nod vigorously. One lick was all it took to render me mute. If she kept this up much longer… Fuck… 

   "Look, I'll do this for you, if you'll change my messy diaper. And don't tell ANYONE about this EVER."

   Fuck, was I really about to agree to this? I did NOT want to come anywhere near that disgusting diaper of hers. But… I'd never had a girl touch me this way before. It was like nothing I could ever describe. I felt I would do anything for her to continue. 

   Even… changing her diaper? 

   She licked the tip again, sending another shudder through my body "Do you swear?" 

   I managed to squeak out a "Yes" as I tried to keep my legs from buckling underneath me. 

   And with that, she wrapped her lips around my cock and started sucking. Her head bobbed back and forth as she took in my entire length over and over, my shaft becoming slick with her spit. I was in heaven. Nothing could possibly compare to this! 

   After sucking for a bit she popped my cock out of her mouth and ran her hand up and down my slick cock, before her tongue shot out again, flicking my tip as she did before. Evidently I was putting on quite the show for her, she kept giggling at me when her mouth wasn't otherwise preoccupied. I didn't care. I couldn't control my reactions at all. For all I knew I'd been screaming expletives without realizing it. All my senses were solely focused on my cock and what she was doing to it. 

   I don't know how long it went on. Coulda been thirty seconds or thirty hours, I couldn't tell. Time had lost all meaning. When suddenly she flicked the tip one too many times and that was it. My cock spasmed in her mouth over and over as I blew the biggest load I'd ever had. My mind was on fire as I gushed in her mouth for what felt like an eternity. 

   I don't know how long I stood there, dazed and dumbfounded, until my senses started to return to me. She was getting up off the floor and wiping her mouth before lying down on the bed, splaying her legs and putting her messy diaper on full display. "I think I've more than earned a change, haven't I?" 

   My mind was still reeling a bit. I had agreed, hadn't I? I could still back out now if I wanted to. What could she do about it? I still had those photos. But she did just give me the best orgasm of my life, and that wouldn't be a very gentlemanly way to show my appreciation. 

   Fuck me. What have I gotten myself into? 

 

///////////////

 

Wow, this is the first smut I've written I like, 5 years! 😅 What can I say, Inspiration can be fickle sometimes. 

Today's work of art, if you can call it that, was inspired by the lovely Ella Raine and her video "Babysitting your Bully in a Messy Diaper" which I will link down below. Go check her out if you can. 😊

https://www.clips4sale.com/studio/136853/23267533/babysitting-your-bully-in-a-messy-diaper 

 

[diaper24/7]

Nice start but you need a little more background to the story for both characters it just feels plain at the moment.

[BabyGabrial]

A new Trip story? Interesting. An original dynamic at that. Bratty little, and shy big. I like it. It's different than all the cookie cutter stories around here. 

[Wannatripbaby]

15 hours ago, diaper24/7 said:

Nice start but you need a little more background to the story for both characters it just feels plain at the moment.

The characters feeling "plain" is somewhat intentional. I wanted to write a simple, self-contained piece of smut for all my horny little friends to enjoy. Can't really do that while also spending 10K words setting backstories. 😅 I wanted to get straight to the "good stuff" and let the reader invent their own context. Plus it allows one to more easily insert themselves into the story if the characters aren't too complex. 

12 hours ago, BabyGabrial said:

A new Trip story? Interesting

I know, right!? I'm just as surprised as you are. 😅 Now only time will tell if my inspiration sticks around or if it goes intk hiatus for another 5 years. 🤣

 

Side note: I just realized I put "Cohesion" in the tags instead of "Coercion". 😂 Silly me. *fixes that up really quick*

[ellaraine]

Omg I love this!! I’m so flattered you’d write a story version of my video, and you did an awesome job! All the gold stars ⭐️ 

[Wannatripbaby]

6 minutes ago, ellaraine said:

Omg I love this!! I’m so flattered you’d write a story version of my video, and you did an awesome job! All the gold stars ⭐️ 

Hi Ella! 😊 I'm super glad you liked it!!!! 😁 I was nervous about changing the ending from how it went in the video, but ultimately decided that this was a more satisfying climax (hehe 😉) in story form. It even leaves things open for a potential sequel (Will he follow through and change her messy diaper? And how did the mother get his number??? 🤔) It could spin off into an entire novella! 

... But I'm 99% sure I won't do that. 😅 I'd rather leave it as a satisfying self-contained story than try to build off of it, get burnt out in 4 chapters, and leave it unfinished. 😅