Trial Period

Park

~Olive POV~

I take him out of his highchair and bring him upstairs to get ready. I change him into a yellow t-shirt, overalls, and yellow and white long socks.

He whines, "Mommmyyyyy, why do I still have to wear a diaper." "Because you are a baby and I don't want you having an accident at the park. Plus you look adorable in it," I say while rubbing the front of his diaper. His face turns bright red from embarrassment as he he puts his hands over his diaper trying to hide it. I laugh, "Hey, at least I didn't put you in a skirt and leave your diaper hanging out."

He pouts and I carry him to the car and buckle in his carseat. I get in the car and start driving to the park. The park is mostly deserted except for a couple who look to be on a date. I take Sammy out of the car and carry him to a bench by the playground. "Ok baby, you can go play but be careful of your diaper so you don't fall or anything." He nods and walks away happily to the slides.

-An Hour Later-

I get up and go grab Sammy, who is playing on the swings. He whines as I carry him back to the car. I buckle him in his carseat and we start to head home.

After a couple minutes of driving I hear Sammy whining. "Something the matter baby?" I ask. "I gotta go potty Mommy," he says with a sense of urgency. "Well good thing you have your diaper on then baby because we are still a little bit away from the house. He whines and yells, "No!" A couple more minutes pass of Sammy quietly whimpering as I hear a slight hissing noise followed by Sammy whining even more.

We arrive home and I carry Sammy into the house. I feel his sagging diaper in my hands as I bring him to the bathroom to get him cleaned and changed.

I strip him of nothing but his shirt and diaper and strap him down to the changing table. I squish his diaper lightly, "Good boy." He wipes his teary eyes and surprised says, "What do you mean good boy?" I respond, "Well you are a baby and you were going to make accidents at some point. But you just had your first proper accident so I'm proud of you baby." He smiles and covers his red, embarrassed face as I start to change him. I start to clean him up when I notice his little boner. I clean off his penis slowly making him harder and start to whimper. "Well well well, what are we going to do with this little one?"