sissychristi:

“Hello little one. Do you know who I am? I’m the Diaper Fairy. I appear to little girls and little boys all around the world. They might not even know they want to be little, but lucky for them my magic can find them. I grant wishes, you see. I grant the deepest, most sacred wishes of these little ones. That’s right, I make them little again. So you know what I’m here to do? Oh sweetie, I know you might think you wanna be big, but that’s just not the case. Trust me, I know these things. So why don’t you settle down and I can change you in to your first diaper. You won’t have anything to worry about from then on. Don’t worry about your friends, about your life, or about any of the silly things that grown-ups fret over. Just let the Diaper Fairy wash all that away and whisk you into nice thick diapers and a blissful return to childhood. How does that sound, sweetie?”


wimpe:

kimsoriginalsissycaptions:

Another original caption by Kim

When I was really and truly a chronological baby, and then a toddler, Janey (mom’s old college roommate and lifelong best friend) lived next door and often looked after me, including bathing, dressing, feeding, putting me down to nap in my crib, and of course changing my diapers.  HAPPY TIMES!

Years later, now that my mom and dad are recently separated, mom accepted Janey’s (actually that’s Miss Janey to me) offer to let us move in with her to help save on living expenses.  Instead of infancy and toddlerhood, I am now going through adolescent puberty, and my involuntary nocturnal emissions are quite disturbing for poor mother (she discovered undeniable evidence of them while doing laundry).  YIKES!

Since I earn a little extra money by helping to look after young children at Miss Janey’s exercise studio for women,

I often think about the very pretty women who worked in the child care room alongside me

while yanking my chain.  A couple of weeks ago, mom walked in on me in my supposedly private bedroom without warning, only to find me desperately choking the chicken.  UH OH!

I was also thinking about some of the kids’ hot MILFs in their yoga pants and leotards and sports bra style tops.  There is absolutely NO shortage of wanking inspiration to be found at Miss Janey’s exercise studio for women.  Some of my school’s cheerleaders and dance team members work out there too.  YUMM!!

Mom and Miss Janey come to an agreement that I should not be left alone to do whatever I wish, satisfying my most fetid desires during this most significant formative period in my life.  So Miss Janey hired mom to manage her exercise studio, while Miss Janey took a step back from running day-to-day operations so she could focus on taking care of ME.

So how’s this for irony?   The same beautiful sexy woman who helped my mom look after me as a genuine baby so long ago is now doing it again.  Miss Janey is as pleased as she can be.  Since she is physically unable to bear children, and since the happiest time in her life was back when she was my caregiver, now she is over the moon since she gets to totally relive those happy days of yore.

Lucky Miss Janey.  And lucky mom, who’s greatly relieved that I am constantly being monitored, watched over like a hawk, unable to get into any more “trouble”, as she puts it.  I’ve tried to explain that masturbation is normal and that every teenage boy does it, but mom won’t hear any of it and Miss Janey just giggles knowingly.  To help deaden my tingly fiery sensations and limit easy access to my – well, you know – mom and Miss Janey agreed that numbing creme and thick padded leg-spreader diapers for me are necessary.  At least for now, they are sufficient, but I overheard them talking very quietly one evening about “chastity devices”.  What are those?

Maybe it’s the close physical and emotional intimacy involved in my personal daily care, amplified by Miss Janey’s undeniable good looks and her taut trim well-toned gym body, but I think I’m falling for her.  Even though I cannot believe for one second her assurances that the day clothes she dresses me in ever came from the boys’ department, no damned way!  I have to be very careful about language like that, since if I blurted it out loud then Miss Janey would give me a spanking and a session clamping down with my mouth on a bar of soap.  YUCK!!!

On the good side, Miss Janey is now homeschooling me so I don’t have to be the little sissyboy wimp at school anymore.  On the bad side, 

Miss Janey is now homeschooling me so she can keep me in diapers and babyish girly attire all the time.  And I don’t even wanna discuss what she’s done to my hair style and coloring.  I’ve tried complaining to mom, but as long as Miss Janey is keeping me up to date with the required state educational requirements and keeping me “out of trouble”, them mom doesn’t care how I look or how I’m dressed.


wimpe:

wittlesissybaby:

Your mommy hired a hot little cheerleader to come and babysit you! So of course she has to show her the proper way to change your diapers!

Honey, I believe you’ve already met Felicia.  Remember at the beginning of this school year when I was appointed the faculty adviser for the cheerleading squad, and I threw a little introductory party over here at the house for the whole cheer squad?  Yeah, that’s where you know her from.

Anyway, as the head cheerleader, Felicia is a natural leader, and she has been my go-to girl-Friday whenever I’ve needed anything done with the squad.  Right now I need a babysitter, and as always, she’s ready to step in the gap and get it done for me.  Felicia is so wonderfully mature and responsible, isn’t she honey?  Just the opposite of you.  You could learn so much from her.

Also, it seems only fitting that she look after you since her father is the handsome gentleman taking me out tonight for dinner and drinks and dancing, and hopefully more.  I’m really looking forward to it; he and I talk and text all the time, and we’ve met up for some weekend festivals that you’re never interested in, and I’ve taken him horseback riding since you’re too scared of those big animals to ever want to go.

Since the sharpness of the barbed hooks makes you nervous and the smell of the bait makes you incessantly whine, I’ve taken him out to see my favorite fishing hole – no dear, that’s not a cleverly phrased euphemism, we really did just fish.  Plus we’ve been out to lunch a number of times, but tonight is the first dress-up dinner date, and I hope he’s as excited as I am.  Ever since he lost his wife to cancer and I lost my husband – yes, that would be you dear – to your ridiculous babyhood fetish, we have both been badly needing some true adult … “companionship”.

He and I just seem to click so naturally, and Felicia and I get along famously as well.  I already think of her as my daughter.

No, Felicia doesn’t have a game tonight or anything, why do you ask dear? Oh, I see.  Actually, I just asked her to dress in her perky uniform since the sporty cheer unis always seem to get you so hot and bothered and frustrated.  Now I’ll just show her how to change your diaper, then I’ll be on my way.  Wish me luck tonight, dear.  If things go as well tonight as I hope then Felicia will be staying over and I’ll be seeing you sometime tomorrow.