“So yes, whenever he´s a good boy and behaves like he´s meant to I like to reward him with a little handjob. I don´t like spoiling him too much, but I understand that regression is hard for him, and it´s not bad to keep a few things from his adulthood. Just, in a different way” *giggle*
“Oh, that´s good! And he behaved so good today! I think he definitely deserves his reward”
“Oh were you a good boy for babysitter Cara? Who´s such a good boy? Yes you are, yes you are! Okay, first thing we do is slide his little pull-ups down. Such cute pull-ups Cara chose for you! Spider-Man looks so good on you!”
“Today little Timmy behaved so well it wasn´t necessary to put him the princesses’ pull-ups. Awww look at his little fella! I have to admit that the fact he´s all shaved makes it look like a toddler´s penis. And look at the little head! It´s like a little mushroom! Coochie coochie coo!”
“Awww baby don´t get all blushy all of a sudden! You know it´s true. If it wasn´t you would be doing big boy stuff with mommy instead of being in diapers. Besides, I don´t think this is too bad for you… I think someone´s little Mr. is asking for attention!” *Both laughing*
“Awww were my tickles enough to wake your little thingy up? Or was your mommy talking to you like that?”
“I´d say both *giggles* Alright, what I do first is make him lay over this towel. We call it the “goo-goo towel”, don’t we Timmy? Oh stop blushing! Well, then I like to apply some baby oil on his wee-wee. This way feels better, right kiddo? Oh yes it does! Mommy´s hand runs better this way, huh? Once I applied it, I start rubbing him with only two fingers, until it´s fully hard. It doesn´t take too long- Oh! There he is, see?”
“Ummm, is that fully erect? *trying not to laugh*”
“Oh well, now you know why I like calling him little Timmy *giggles* Oh you´re being so blushy today! I think someone has a little crush on his babysitter! Yep, his thingy just twitched”
“Oh really Timmy? You have a crush on me? Awww sweetie, that´s so cute! It´s a shame you´re not big enough to please me, and instead, you´re trapped in those little Spider-Man pull-ups being rubbed by your mommy”
“Ummm, Fae… I think he´s about to cum”
“Oh yes he is! Very attentive Cara! Already Timmy? Are you gonna make a gooey accident? Can´t you hold it for a few more minutes? No, right? Tsk tsk. You´re busting each day faster, and at the same time, you´re getting each day further from mommy´s big girl parts… Okay Cara, what I do when he´s about to cum is slide his pull-ups up again to rub him. Yes mister, you know the rules. You lost that privilege, keep your hands still!”
“Awww, he doesn´t even get to cum like a big boy?”
“Not at all! He used to, but since we started with his regression, I made sure he started associating the cumming sensation with the on he gets when he has an accident. It´s a reward for him, but it´s also a time where he feels inadequate and shamed. So now, each time his little thing fills with cum, it also fills with pee pees, and the result… Well, it turned kinda messy”
“Wait, you´re telling me that as soon as he cums he also starts pissing himself?”
“OMG hahaha that has to be the most pathetic thing I´ve ever heard! I´m definitely way outta your league champ!”
“Aw, is someone getting upset? Hey hey, don´t start crying! Look, mommy´s rubbing your pull-ups. Do you like it? Oh yes you do! I can feel your little fella twitching there! You´re close to cumming aren´t you? Do you want your teddy bear? Can you give the baby boy his teddy bear, Cara?”
“Oh sure! Does it make you feel safer when you make your cum cums? Aww, such a blushy boy!”
“Alright kiddo, hold that teddy bear tight. Mommy´s gonna rub you faster so you can make your cummies. Are you ready? Oh, someone likes when mommy touches him. You can´t stop whimpering! Are you gonna cum? Are you? Is the little baby going to have an accident in his pull-ups???”
“Awwww, there you go! Someone´s been saving his messies for a long time! Look at this mess!”
“Thank god he made it inside his pull-ups! Though I don´t think there was any other way for him to make his little cummies, wasn´t it? Awww… Wait, are the little stars on the front of his pull-ups fading away?”
“Oh baby, are you having an accident now? Awww, yes you are! Look at how much pee pees you´re making! Making cummies was too much for your little friend and he couldn´t hold your wee wees in huh? And now you´re here with your pampers full like a little baby, in front of two hot girls you crush on. Are you gonna cry? Why don´t you give mommy and babysitter Cara a good cry like the fussy toddler you are? Then maybe we will change you…”
