Daily Free-Write March 19, 2021

“An Easy Bet”

“Hey, got off! Come one guys!” whined Dexter, who was being held down by a much larger man in a wrestling team jersey.

“Wanna see a magic trick? Check this out!”

Nelson began to rub the front of Dexter’s diaper eliciting an involuntary moan. The man had dexter in a pin, one arm draped over the Dexter’s waist, his side laying over Dexter’s hips blocking Dexter’s view to his lower half, and giving Nelson free access. And Nelson intended to take full advantage of his position.

“Nnngh! No, don’t make me… un h… cream my diapers, dude! Mercy!”

Dexter was stuck in a loop of sorts. Each day he came in his pamps meant another day he would have to stay as a house baby. It seemed so easy to agree to when he joined. Just had to go through one day without cumming his pampers and he’d graduate from house baby to full-fledged member, sending another house member to take his place. He hadn’t counted on just house resourceful the house members were. They took turns making sure he came once a day at least in his diaper.

Some did it right away with a buzzy wand at midnight, or the moment they woke up. Others liked to give Dexter a sporting chance, planning ambushes and surprise attacks that led to humiliating explosions of orgasmic bliss in his diapers. The more public, the more embarrassing this situation became. This one was perhaps one of the worst, pinned down in the grass outside of the student center, having his diaper worked for everyone to see and nothing he could do about it.

“Unh….” He grunted again, trying and failing to get out from under Nelson.

“Aww, little guy still has some fight left in him. Do you think I should let him up? Nah, not before we see him make creamies and prove he wants to wear another day.”

Dexter whined as his tensed up muscles finally tired and he went limp, feeling the thick patting bunch up around his cock and balls, crinkling as Nelson smiled and toyed with it. The three guys with him were pointing and laughing, drawing in more people to look at the spectacle.

“Hehe, It’s okay guys. It’s almost finished. You’re gonna see a diaper boy magically fill his diapers with cream! Isn’t that right, pampeboy?”

Dexter shook his head and whined but it was already too late. He could feel his orgasm approaching fast as Nelson’s hands moved rapidly ofter his hard cock, squeezing it and stroking it through the padding. The worst thing was, the more times this was done to him, the more of a diaper boy he became – associating diapers with pleasure. In a matter of moments, he would lose the battle and squirt, just like always.

Nelson slid his hand up further, cupping Dexter’s padded butt, sliding up and working him from a new angle. Dexter didn’t stand a chance. With one final mighty push, he managed to lift his butt off the ground and thrust his hips in the air, his red straining face and the cute moans letting everyone know what he was doing in his diapers.

“Awww! So cute! Little deedee loves his diapees! That’s okay, baby butt. You can wear them another day. Maybe tomorrow, you’ll be ready to grow up. As if.

The man got up off of the defeated Dexter and high fived his friends, who were all laughing.

“See you soon,” he said, with a grin, as the posse walked off. Dexter knew that for the rest of the day he’d have to look over his shoulder, knowing that at any moment, Nelson could pop up and bring him to the ground for his diaper check/masturbation session.

He got up, and rubbed his eyes, ready to leave when he was grabbed by the hand. It was another brother from the house.

“Come on, diaper butt. Let’s get you changed in the student center. No sense of you wandering around in a wrecked diaper.”

It was true. Nelson’s rough treatment had seriously compromised the structural integrity of his padding. Dexter could only whimper as he was led into the student center by the hand. He’d find away to get through the day tomorrow without cumming and get out of this silly baby treatment. He was sure of it. Still, he couldn’t deny that the diapers were becoming a serious turn on for him. He gulped. He hoped he wasn’t becoming a diaper boy for good.

-Written by Champ