Daily Free-Write March 25, 2021: An Easy Bet Pt. 3 (Patreon)

Hey all! Here's the next free-write. A $5 tier PDF file and $10 tier Hypno file are both coming shortly (Monday and Tuesday). Cheers! 

Continuation of March 24, 2021 "An Easy Bet Pt. 2"

The light switched on and Dexter blinked, his eye adjusting. He had been led up by Alpha, up the stairs and into the middle of a room that smelled… strangely familiar. A sweet scent that he couldn't quite place. Then, the light flipped on and he saw he was in a large oversized nursery with furniture and equipment sized for a very big baby. Just like him.

"You can't be serious," said Dexter, as if the thick wet diaper and bunny sleeper he wore weren't ridiculous enough.

"Come on, Dexter. I'm an honest guy." Alpha put his hand to his chest like he had been insulted. "I promised you protection, didn't I? Well, what's more protected than wearing your thick diapers and staying in your super safe and padded nursery? Nothing to hurt yourself on here, little guy."

"Lemme go! I'm not a baby!" said Dexter, trying to pull away, but Alpha was much too strong. He now knew what that smell was. It was baby powder. And as he was strapped into the crib by the wrists and ankles, he had the distinct feeling that it was going to be a very familiar smell. The plastic mat crinkled underneath him as he squirmed and wriggled, but nothing else came of it. He watched the bars of the crib go up like a prison cell, locking him in for the night.

"Sorry for the rough treatment, little guy," said Alpha. "It usually takes a few nights before we can be sure our little ones won't try to make a break for it. But at least you don't be able to rub your diapees! After all, you seemed pretty worried about being able to resist cumming in them, right?"

Alpha reached through the bars to  rub the front of Dexter's bulging wet diaper. He was right about one thing. It would be hard to resist cumming in them. As disgusting as it was to Dexter, the thick soggy padding did one thing very well - it hugged and rubbed his malehood, stimulating him whenever he made the slightest movement. Even without the bigger man's hand rubbing the front of his diaper, he would have been hard pressed to resist humping his crotch into the air. What a bizarre turn of events for Dexter.

"Oh my," said Alpha, noticing the bespectacled math nerd grind his crotch into his hand. "Looks like somebody is enjoying themselves. Better be careful, buddy, or you might get yourself stuck in the nursery for a long time."

Dexter shook his head. "Never!" he said through gritted teeth as he summoned the willpower to stop thrusting.

"Oh? Is that a challenge?" asked Alpha, beginning to take over where Dexter had stopped. Now he was back to rubbing the front of the new pledge' s diaper and smiling.

"Hey guys! Get in here! The baby's enjoying his diapers!"

A rush of fraternity pledges and brothers bounded up the stairs and into the room, hooting and cheering as the nerd tried to resist the man's ministrations.

"Uh oh! I think he's getting close! Almost seems like he wants to be the house baby.

Tied up as he was, Dexter could do nothing to stop the hands that rached through the ball to tickle and tease him as more members crowded around the crib. The bindings were unyielding leaving him wide open to be groped and rub in whatever way they saw fit. He was actually glad to be in the diaper and bunny sleeper at this point, as they offered some protection from the probing hands. Nevertheless, they didn't do much to stop the stimulation from reaching a fever pitch.

Just before he thought he would cum, Alpha called a stop to it and brought out a digital clock which he set in view of the crib.

"Okay, everyone, let him breathe a bit. We're gonna play with the baby til midnight and see if he can control himself. If he manages to resist the urge to cum before 12:01," he tapped the face of the digital clock, "then he'll win the little challenge. I'll be taking bets. And given how much he obviously loves them, I'll be taking bets 10 to 1 that he doesn't make it.

"I'll take that bet," said one pledge. Alpha grinned as more pledges started to place their bets, though not the senior members, Dexter noticed.

"Don't worry, Dexter, my friend," said Alpha, "I won't force you to cum before midnight. I'll just take you to the edge and let you decide. This is a challenge about self control. At least for tonight. But if you show us you really want this, then all bets are off. Or I shoudl say, rather, anything goes."

Dexter was red-faced. "You meanie! There's no way I'm gonna lose your stupid game. This is an easy bet, you'll see."

"Oh? Do you want to wager something?"

Dexter thought. "Maybe. Maybe if I make it, you have to wear the diapers."

Alpha chuckled. "Is that all? I'd take that. How about wagering some money to make it more interesting. How does a thousand dollars sound?"

Dexter gulped. "A th-th-th-thousand dollars?! I don't have that kind of money!"

"What's a matter? I thought you said it was an easy bet?" said Alpha, in a mocking tone. "Guess that was all talk huh? Yeah, I'm not taking your bet, son. You're obviously not mature enough to be making bets with the big boys."

Dexter was red in the face. This was exactly the kind of teasing he got in high school and he was sick of it. He would show this jock loser who the baby was!

"Fine," he said. "A thousand dollars, and you go into diapers."

"Good boy," said Alpha, patting Dexter's diaper and making him moan. "And if you lose, no holds barred. You'll be stuck in the nursery in a very special seat for all of tomorrow. A little something that only the biggest diaper babies get to use."

He nodded over to a large bouncer in the corner of the room.

"One day in that and you'll be a diaper boy for sure!"

"Yeah, you're the one that's gonna be in that one."

Alpha squeezed the front of his diaper, focusing on the bound boy's dick for a few seconds, before tapering off, leaving Dexter needy and humping the air, desperate for just a little more.

"Are you sure?" asked Alpha, smirking.

Dexter didn't reply. He just looked away, his face still bright red. As much as he hated to admit it, the diapers felt better than any sex he'd ever had. Though, admittedly, the only sex he'd ever had was with his hand while looking at pictures of his favorite anime girlfriends. If he couldn't keep it under control this time, the only cartoons he'd be watching would be baby shows.

The party had officially moved into the nursery with various frat brothers taking turns manning the crib, keeping Dexter entertained' as the hours ticked by.

True to their word, none of them pushed him over the edge. They would always leave off at the very last minute, and Dexter would be left humping the air. It would take him a few seconds to catch his breath and realize what he was doing. Then he would stop. Looked embarrassed. Go back to denying that he liked any of it.

When the clock said 11:59, Dexter was in the middle of a very intense rubbing session from Alpha. The scent of piss and baby powder was strong in the air, and it was getting all mixed in with the pleasure signals and the diaper sensations coming in until they were all tangled up in one big knot. Alpha nodded to another member and a massage wand was mounted to the side of the crib, and positioned just above Dexter's crotch. Alpha made his rubbing lighter and lighter leaving Dexter desperate once more.

"Almost midnight, buddy. You think you can hold it til then?"

"No! No way," jeered the partygoers around the crib.

"I c-c-can," said Dexer. "J-j-just wa-oohhhh" his hips gave an involuntary jerk upwards and he was almost buzzed to oblivion by the wand. He slammed his butt back down on the matt with a loud crinkle and manage to stave off the orgasm, his dick convulsing in a mini orgasm that produced no semen. That was a close one for sure.

"You're almost there," said Alpha. "You just have to make it to 12:01 and then you can cum as much as you want!"

Dexter was sweating bullets. He was hornier than he had ever been, but he knew he  would have to summon all his willpower and resist. After what seemed like an eternity the clock switched over to 12:01 and Dexter immediately thrust his hip upward to get that stimulation he so desperately wanted.

"Ohhhhhohhhhhhhhohhhhhhh…" he moaned. After several hours of edging, his orgasm seemed to stretched on and on as he splatttered the front of the former house baby's soggy padding with his own seed.

"Atta boy. That's the way," cooed Alpha. "Alright, everyone. Looks like we have a… LOSER!" The crowd clapped and cheered. "Alright boys, hand it over. And if you can't pay up, we'll have to arrange some other methods of payment I'm sure your senior members can tell you about. That means you too, DeeDee." he said, looking down to Dexter, who was still catching his breath and convulsing from the occasional aftershock.

"W-wait." he gasped. "What are you talking about? I made it to 12:01!"

"Ooh, I'm sorry, buddy. I forgot to tell you. We never ended up resetting this clock for daylight saving time. It's an hour fast! The time is… 11:01."

Dexter couldn't believe he'd been tricked. He had known what time it was when he and Eugene got there. How could he have missed it when the clock said 9 instead of 8?

"We'll change you in the morning, baby boy," said Alpha, patting the exhausted boy's head. "But hey, at least you get to stay in the diapers you love so much. That' s a bonus, right?"

The room began to clear out. The fun was had, and people had other interests, and pledges, to attend to. Before he left, Alpha smiled down at Dexter with a devilish grin.

"Aww, don't look so sad, guy. You'll love being the house baby. We're going to have so much fun with you. Tell you what, why don't I just put this… down here…" Alpha lowered the wand so it was pressed firmly against Dexter's diaper front where he couldn't get away from it. "And you can enjoy your diapers all night long?"

The remaining people in the room laughed as Dexter grunted and squirmed, soon being milked of yet another load. Then another. This attracted a new wave of interest and a few of the people in attendance started up a drinking game where they took a shot every time he had an orgasm, but at  midnight, Alpha came back in and stopped it, removing the wand from the crib.

"Alright guys, come on, come on. Let the baby get some rest. I think he's proven how much he loves his diapers."

And with that, they cleared out. Alpha turned on the mobile and pinched Dexter's cheek, "Gotta leave some in there for tomorrow's fun time with Mr. Bouncy, don't we? Sleep tight, baby."

Dexter stared up at the mobile, hoping that tonight would be the last night he had to look at it. But as he drifted off to sleep, some part of him was already craving more.