Month: February 2018


wimpe:

That’s right Bobbi Jo Baker, take a good long look in that mirror and think about whether you like what you see, what you’ve become, what you’ve descended to.  It’s not pretty, is it?  Sure, it may be “cute”, but it’s certainly not pretty.  And to think, I actually used to date you back when you were “Robert Joseph Baker”.  I really liked you a lot, and I thought we had a good thing going.  You shied away from sports and cars and hunting and working with tools, or most any masculine thing most guys around here like, but I had no problem with any of that. 

You were sweet, shy, polite, and always sensitive to my needs.  

I was even thinking what it might be like to be your wife someday, buying a home, starting a family, and having a fulfilling life together.  And now, the sheer irony of me being your extremely well-paid babysitter.  Boy, did I ever dodge the proverbial bullet!  

Your new stepmother Cara was able to quickly discern your true nature, and it didn’t take her very long to sell you on her vision, did it?  Incredible how being sissified and infantilized by her has just so utterly consumed and overwhelmed you.  I know that Cara is a very strong-willed woman, and that you have always been passive and non-confrontational, so I wasn’t particularly surprised when she first sent you to school in a pink poplin shirt with its tiny pearl buttons on your left side, decoratively-stitched skinny mom jeans and a rhinestone-studded pink belt, but I had hoped you would at least try and show a little backbone. 

By semester’s end she had you rocking your classes in designer dresses and matching pumps.  At least you were fashionable.

When you didn’t stand up to her, or at least try and push back a little against her, I had to give you the whole “let’s just be friends, it’s not you it’s me” speech.  Well, it actually was you.  How could I date a guy with a more fashionably femme wardrobe than me?  

I know your dad wasn’t much help for you against her pushiness, but she effectively neutered him early on from ever being in your corner.  In all fairness, the poor guy was badly missing female companionship since your mom passed, and Cara is still just in her twenties, smart, funny, a real looker, and probably a Tigress in bed to boot.  So he stepped aside to let you fight your own battles with Cara.  Which you didn’t, not really.  You just surrendered.  Not sure how or why you wound up in diapers, but hey, it’s your life.  You’re the one who has to look at yourself in the mirror every day, just as you’re doing right now.

By the way, have you peed your diaper yet Bobbi Jo?  Remember Cara’s instructions, you are NOT to stop looking at your reflection UNTIL you’ve pooped or peed yourself.

Oh that’s right, you can’t answer with that paci in your mouth, and you’re not allowed to remove it.  Alright ya big baby, I’ll come over and check.  Hang on sweetheart, babysitter’s a comin’ to check you.


wimpe:

Look Jeffrey, I know this is really awkward since we’re both in sixth grade and we share four classes together, but your mom did hire me to babysit – uh, sorry, make that HANG OUT WITH – you this afternoon while she’s chairing that PTA committee meeting, and I really could use some more cooperation from you.  I need you to let me tie your shoes even though I know that you already know how, because those were your mom’s strict instructions.  If you choose to not cooperate with me then I won’t physically fight you, but I’ll have to inform her of your disobedience and leave you to face her consequences later.  I’ve only just met your mom, but from what I can tell, I think you should try

really hard to stay on her good side.  Really really hard.

Okay, that’s better.  See, that wasn’t so hard, now was it?  She left me a schedule, and the next item on it is some playtime outside to take advantage of all this beautiful fresh air and sunshine. 

Sorry about your too-cute-for-words outfit, but it’s what your mom put you in, so it’s what you’ll be wearing, even outside.  She was adamant about that!  She told me you “richly earned the privilege of wearing it” after you threw a childish tantrum when you first learned I was coming over to babysit – I mean to HANG OUT WITH you.  But see, there was no need for you to throw a silly hissy fit, now was there?  I may be a cheerleader, but I’m not mean or snooty.  Hey, I don’t even bite.  So I’m not so bad.

Anyway, I promised your mom that I’d teach you how to skip rope and play hopscotch.  I have so many happy memories of my older sisters hanging out and teaching me.  I’ll try my very best to make it fun for you, I promise.  Hey, I just had a great idea.  After some fun with hopscotch and jump-rope, I’ll teach you some of our squad’s school cheers and the accompanying gymnastic and dance movements.  I have my cheerleading uniform, athletic shoes, pom-poms and hair ribbons in my bag, so maybe I could text your mom and ask her if she’d be okay if we fixed up your hair with really super cute school spirit ribbons, then temporarily got you out of that childish thing you’ve got on and got you changed into my squad outfit – you’ll need help with the back zipper for sure.  Maybe doll up your pretty face for extra special super-dramatic effect.  I have my makeup kit in my purse (I never go anywhere without it), and we really lay it on thick on game days.  I could take some pics and film of you doing cheers and send the pics and vid to your mom.  I’m sure she’d get a big kick out of it.  I know I would!

No no, Mr. Fussy Britches, don’t worry your pretty little head, no one else will see your pretty painted face enthusiastically practicing cheering on the brawny big boys, unless they just so happen to drive by while you’re performing, but at least you live on a cul-de-sac, and your mom assured me that the neighbors have seen you when she’s gotten you all prettied up before, so no big deal, right?  

Oh no, don’t start giving me trouble NOW Jeffrey, not when we were just starting to bond and get along so well.   I know it’s not a huge deal for you to be outside in pretty clothes because your mom told me all about the huge wardrobe and trunk in your room that are stuffed full of “dressup play clothes”, … she tol me that there’s fancy party dresses and bikinis and nighties and dance recital outfits and tube tops and short-shorts and much much more, all hand-me-downs graciously donated by your many female cousins.

Your neighbors have already seen you wearing them outside many times, and you’ve even had fancy dressup pretend tea parties with the younger neighbor girls, where you each had to dress up fancy and bring a favorite dolly.  What did you wear and who did you bring, Jeffrey?  Who’s my pretty boy’s favorite dolly?  Is it Barbie?  An American Girl?  Raggedy Ann perhaps?

Okay okay, stop sniffling little one, I’m just having a little fun with my oh-so-special boy.  Look, I told you I’d ask your mom for her permission about teaching you to cheer, and if she says no, then no, we won’t do it.  Alright, I’m sending her the text … now ….

 … Wow, that was a fast reply!  She said, “Go for it!” along with the emoticon that’s laughing so hard it’s crying.

So Jeffrey,  I fully expect your complete cooperation, including happy squeals and big smiles and high kicks and prissy dance steps and girly hand gestures that I’ll teach you, and if I don’t get them from you, then I’ll inform her of your disobedience.  She’s given me authority over you for this afternoon, and I’m exercising it in full.  Period, end of story.

Oh by the way, don’t worry, your mom told me all about your extensive ongoing incontinence issues, which I guess explains why you don’t play any sports and never dress out for P.E.  I had thought it might be because you were afraid of the other boys’ rough ways since you don’t have a dad at home as a strong male role model, so I just assumed you begged your mom to use her influence with the school administration to get you out of P.E.

And to think I had it all wrong, it’s just because you still have to wear diapers, even in the daytime.  Aren’t you getting a little old for that kind of thing?  Good thing the non-bulky ones they make nowadays are pretty discreet, huh?  Or else things could be awfully rough for you, poor lil fella.  There’s a lot of meanies and bullies among both boys and girls at our school. 

Ok, let’s head outside.  Your mom said that in your garage there is a pink jump rope she uses for her crossfit, along with some sidewalk chalk to draw up the hopscotch squares.   I’m really going to enjoy this.  I’m SOOOO lucky that my cheerleading practice was canceled today.   I know this may sound kinda strange Jeffrey, but I really REALLY like being the boss, being able to dictate what you have to do, when you have to do it, whether you want to or not.  Ooh, this kinda power trip can really get me all flushed-faced and light-headed and tingly and excited – I love  it!!

Do you like being my helpless underling, even just a little bit?  You can tell me.  Really, you can.  Be totally honest.  Oh, you don’t, eh?  Too bad, but in some ways your reluctance just makes it even all that much BETTER!  Maybe your mom can let me hang out with – no, make that BABYSIT – you again sometime.  I’m already getting more fun ideas of what we can do.