A Sensitive Guy - Part 2

This never got posted cuz I'm dumb

Read part one here! 

...

Though Sam could barely recognize his life anymore, he could identify where it had all shifted, where the slide into his new role had turned into an inescapable avalanche.

It had all begun with two keys.

The first key locked his new chastity cage.

The second key unlocked Tim’s front door.

The cage wasn’t because Timberly wanted to deny anything from Sam–obviously not. She explained how she didn’t mind him having fun, she wouldn’t even mind if he masturbated, but his ‘special times’ were becoming so frequent lately that it was becoming a problem. They couldn’t snuggle on the couch or even hold hands without one of his accidents interrupting.

A pink, plastic, locking shell, something to keep his cock isolated and unstimulated, might mean he didn’t go through quite as many pullups in a day.

She’d even let him keep the key, right in a special spot in her dresser.

Still, Sam couldn’t exactly shake the feeling that this escalation was more than just practical. She’d proposed something intimately disquieting at the same time that she offered him a major life improvement–getting out of his parents’ basement and into her house.

So, after taking a few days to think about it, Sam added two keys to his life. One to Tim’s home, and one to his own cock.

She helped him put it on–just fumbling with his dick for a moment had been enough to make Sam spurt into her hands, but in the post-coital limpness that followed, she got him all locked up inside the pink plastic chastity device.

Then he got to see his new place.

No more basement apartment, no more paying rent to mom, no more dependence on his parents–he was his own person, with his own home. Or, well, with his own room in Timberly’s home. Her former office, in fact, but who was checking?

An attempt had been made, but sleeping in her bed was off the table–every time he rolled over and brushed his skin against hers, he woke up to startling bliss, and he’d been so crabby and sleep deprived the next morning that Tim decided he needed his own space.

It was a nice room, too–Tim’s old desk was huge, a great work surface for him to work on projects; it was nearly as big as the old single mattress in his basement abode. He’d initially seen the appeal of the work surface, but it’d taken some advice from Tim for him to decide what to use it for–since there wasn’t any more pressing work just then, he found an old lego kit that’d been languishing in a storage box of his for years for lack of time and space.

Sam had space to arrange every piece, and Tim didn’t say a word about his hobbies being juvenile or a waste of time.

He tried not to be embarrassed by the diaper pail she’d installed under his new desk. It was for practical reasons; even with the cage he still went through a couple pullups every day. It’s not like he’d have to bring guests in here and explain to them why he had the pail.

Timberly was still out and about a lot, so they spent more time chatting than speaking in person, but that wasn’t new–they’d always spent more time messaging each other than face-to-face. Occasionally she’d ask him to do specific chores around the house that’d been languishing, and he was more than happy to do so–it’s not like she was asking him to pay rent or anything, and he just wanted to see her smile when she came home to a clean home.

If anything, the notification chimes that came when she had a little job for him became highlights of his days off–they were an opportunity to make Tim happy.

Their time in bed got more interesting, too–his cage didn’t really stop him from dribbling out into his pants when things started to get hot, but his chastity at least made it so he lasted sixty seconds instead of six.

After ten days of this new arrangement, Tim had another idea.

He was bringing in barely minimum wage at his dead-end job, so why bother going to work? She made enough, so she could pay him an allowance to do chores, and he wouldn’t have to spend all his time doing something soul-crushing. Sam wasn’t about to say no to an offer like that, not when he’d fantasized about quitting a thousand times.

Maybe it hadn’t been mature for Sam to tell his manager to go fuck himself with his ‘World’s Best Boss’ mug when he went to pick up his last check, but he didn’t care about burning that bridge. He had Tim.

Then something else…changed.

Tim’s house was nice, but it wasn’t massive, and it only had one bathroom. One morning, while Tim was getting ready for work, Sam found himself needing to pee, and the bathroom door was locked.

He knocked, shifting his weight from side to side. The need to go had come on fast. “Eh, Tim? Are you in there?”

She replied sweetly, unaware anything was wrong. “Yeah, do you need something?”

“I have to pee,” he explained.

“Oh, sorry. I’m on the toilet right now.”

And that was that. He paced, he tried to think of something else. He let seconds drip past, but he had to go, and the need wasn’t getting any better. It’d come on strong and without warning, like his bladder just forgot to tell him how desperate he was until the need was at a Ten.

He knocked again. “Tim?”

“Yeah, Sammy?”

“How much longer?” Bouncing from toe to toe in a dance of desperation, he fought the urge with all his determination. “I, eh. I really need to go.”

“Oh, well…” She paused, then made an absurd suggestion with the same tone and cadence she used when she asked him to do the dishes. “Just use your pullups, sweetie. They’re meant for that, anyways.”

(She can’t be serious, can she?)

But before he could contemplate the suggestion anymore, his body decided, ‘Yeah, that’s a great idea,’ and gave up fighting. He froze in place, mortified as he felt urine flood into his pullup, soaking the garment front to back.

It didn’t go quickly, either–his bladder had been full to bursting, and once the trickle started, it didn’t let up. Terrified something might spill out into his jeans, he just stood there, frozen and acutely aware of the humiliation dribbling into his technically-not-a-diaper.

A moment later, Tim flushed, and after a brief hiss of the sink, she pulled open the door. Drying off her hands, she said, “Okay, it’s all yours.”

He stared at her, cheeks flushed bright red. “Um…I don’t need to go anymore.”

Her eyebrows raised, but Tim didn’t laugh or tease, she just smiled. “Oh, okay–well why don’t you throw that soggy pullup away and you can take a shower?”

Natural. Like nothing out of the ordinary had happened at all. Looking back, it was as though she’d expected this outcome and been prepared for it.

Sam was too mortified for that level of scrutiny just then. Nodding, he hurried to clean himself up.

But, just like his other accidents, these didn’t stop happening. And, just like when spurting into his boxers, piddling his pants always managed to happen in front of Tim: They’d get in her car to go somewhere, and as soon as they were on the highway his bladder would suddenly be desperate for release. They’d be over at her friend’s house, and the bathroom would be occupied. They’d be out for a walk, or any one of a half dozen other problems–it was as though his body had decided that it only needed to go when the bathroom was unavailable.

The pullups held up most of the time, but occasionally, he’d have to deal with crescent moon stains around the leak guards, marking his accidents for everyone to see.

What Tim suggested next didn’t even surprise him, though it caught him off guard that she didn’t even wait for his approval or confirmation. She just came home from work one day with a package of puffy, white adult diapers. He didn’t recognize the brand, but it’s not like he spent much time wandering the diaper aisle at the pharmacy–he’d just have to trust Tim’s judgment and assume that “Trests” would be effective for the job.

When protests were made by Sam, Tim had silenced them with ten words.

“Don’t you want to be a good boy for me?”

After that, he wore his diapers obediently, and never looked back.

His bladder didn’t look back, either–once he had somewhere to go potty wrapped around him at all times, he didn’t seem able to make it to the toilet at all. Something in him had accepted his diapers wholesale, and now it was hard to even think the word ‘Toilet’ without feeling an immediate release.

After only a few days, it became hard to even notice when he’d gone.

After a few days more, it became hard to even notice when he was wet.

Eventually, when Tim came home to find Sam had leaked through his diapers and onto her couch without noticing, she declared she’d had enough. If he wasn’t going to keep track of his diaper’s state, she would, and so a new part of their dynamic got added: In the morning, she’d check him, and when she found him inevitably soaked, she laid him out on his desk and changed his diaper.

He’d have to change himself around lunchtime, but it took Timberly texting him a reminder to get him to do it, and once she got off work, she simply deprived him of pants so she could tell when he needed a freshie at a glance.

That was good, though, because checking him with touch had its own side effects. All it took was Tim’s hand cupping his crotch, and he’d have the same reaction as always–brief, humiliating bliss. He’d already grown to associate the feeling of his soggy diapers with orgasms, and that was a correlation he didn’t want to reinforce in his thoughts.

The plastic sheet she got to go over his desk made it look distinctly like a changing table, which Sam found to be an odd coincidence, but he didn’t point it out. What he did point out was that he could no longer use the surface for his hobbies.

To that, Tim suggested he simply play on the floor–it’s not like he was using that space anyways, and there was plenty of room down there.

Really, though, as long as Tim didn’t mind his accidents, Sam didn’t either.

After a month living together, Timberly suggested just one more change, sandwiching her proposal between idle commentary about work and a question about what he might want for dinner:

‘Do you want to try a strap on?’

Sam had taken it with surprise–he doubted he could handle a strap on. Occasionally when they’d started fooling around, Tim had tried fingering him, and just a second or two of anal play was enough to make him dribble in his diapers. How was he supposed to deal with being fucked?

But then, Tim had clarified, and it all made a lot more sense.

‘You’d wear it. Don’t get me wrong–I like your mouth–but I’d also like to be fucked, and since you can’t do it yourself,  maybe you could use a substitute? I’d really like that, sweetie.’

He got it, then–his own cock was kind of useless, trapped in a cage, and ready to spurt helplessly at a second of contact. It felt good for him, at least when he wanted that reaction, but wasn’t much good for Tim.

So, they got a strap on. Or, ‘they’ didn’t. Tim picked it out for him.

It felt awkward putting it on over his diaper; a puffy layer of padding between him and his new cock. Still, Tim liked the look, pulling him in for a bliss-inducing kiss that had him needing to sit down for a couple minutes before they tried the strap.

Once he’d caught his breath, though, Tim pushed him down onto the bed, slid out of her panties, and began to ride his store-bought cock like she’d been the one locked in chastity for weeks.

Being inside Tim like this felt nothing like the sex he’d had before. Intimate and apart, slightly demeaning but full of connection at the same time. He was fulfilling his role in a way that he felt like he should, and yet…in a way that was focused all on Tim’s pleasure, because his own was already guaranteed. He just focused on having his ‘cock’ inside her, giving her pleasure, and imagined they were having real sex for the first time in their relationship.

What he didn’t expect, while Tim’s breath grew quicker and she began to grind her hips harder, was the sudden pressure that exploded out of nowhere in his belly. It was without warning, without any sort of chance to hold it or wait–he needed the bathroom, now.

“Tim, I–” he blurted, but before he could finish the words she’d bent forward, the back of her hand on his head, pulling him into a deep, passionate kiss.

He didn’t have the words, or the sense, to finish his objection. Feeling her tense and moan into his lips was enough to bring out his own comparatively delicate orgasm, and all in that same instant, the unexplained and unexpected pressure won out.

They held each other tight through the simultaneous climax. The whole time, Sam felt heavy, solid mush spill out of him and into the seat of his diaper, enough to make it crinkle as it swelled. Whether she noticed the little grunts that escaped his mouth, or the shifting of his body that happened automatically to help facilitate the humiliating accident, Sam couldn’t say.

After a long, quiet moment, Tim pulled away, and Sam had to look her in the eyes and admit what’d happened.

“Tim, I–” he started, eyes huge.

“Shh,” she said, looking down on him. “It’s okay, baby. You couldn’t help it.”

She was right. He couldn’t, and even though it didn’t make any sense, her acceptance–her radical willingness to take every demeaning, humiliating thing that happened to him and laugh it off with a smile–made him melt.

Timberly smoothly got up off his strap-on, off his mucky diaper, and rolled next to him in bed, snuggling close so her head was against his.

“I love you,” he said, with the full vulnerability of exposing how he really felt.

“I love you too, baby,” she said. “I knew you’d be perfect, once I was done with you.”

Sam didn’t know what she meant by ‘done with him.’

He didn’t care, either. It didn’t matter.

He was in love.