Getting Over The Hump

Author's Note: Another loooong chapter, for your enjoyment!

The bedroom was dim, quiet except for the low, insistent hum of devices and the occasional soft gasp slipping through Kieran’s parted lips.

He lay on the bed with the sheets bunched beneath his thighs, back pressed to the headboard, neck arched slightly as he looked down at the glowing phone in his hands. His fingers moved quickly over the screen—long, delicate fingers tipped with almond-shaped nails still painted in that dusty mauve Celeste had chosen earlier in the week.

The vibrator buzzed steadily against his cage, held snug between his thighs. He didn’t need to grip it anymore—his legs pressed it perfectly into place, the tension keeping it in constant contact with the base of the device and the tiny bit of exposed flesh beneath. Inside him, the prostate stimulator pulsed and rotated in rhythmic waves, its curved head nudging deeper, vibrating in sync with each subtle shift of his hips. The sensation wasn’t painful. In fact, it was undeniably good.

Just... not enough. Again.

Thirty minutes in, and the same problem had returned. He felt it—heat, pressure, a tickle of pleasure up his spine—but it didn’t climb. It didn’t break.

He wasn’t close. He should’ve been.

His body had adjusted to this by now. The toys weren’t new. The cage wasn’t new. The feeling of being plugged and teased was supposed to be shocking the first few times—but this? This was now the third time since the first time about a week ago.

And still no release.

The screen of his phone reflected faintly off the gloss of his lips—he hadn’t even bothered wiping off the light pink balm he wore to bed most nights now. Just habit. Like the satin shorts around his ankles, or the bralette hugging the empty cups against his chest. The breast forms were off, but everything else? Everything else was soft, smooth, feminine.

Even his scent. He could smell it on himself. That faint Euphorica blend of floral musk and clean skin, wrapped around his thighs, his collar, his sheets.

He shifted again—hips tilting just slightly, thighs tightening to increase the pressure of the vibrator. The stimulator buzzed deeper inside.

Still nothing. He opened his browser. Private mode. Again.

“why can’t i cum with vibrator and prostate toy”

He clicked the first link. Nothing useful.

Frustrated, he pulled open ChatGPT.

“I’m locked in chastity and using a vibrator and prostate stimulator but can’t orgasm. Why?”

He hit send. The bot’s reply came almost immediately, cheerful and calm.

“If you’re unable to orgasm despite strong stimulation, it might be due to a few factors: not being sufficiently aroused, overuse of toys without mental build-up, or needing more time to allow the arousal to fully build. Many people find that orgasm under these conditions takes longer and requires edging for 45+ minutes, sometimes even longer.”

Kieran’s head rolled back against the headboard.

He was already going insane day by day. This kind of longing for an orgasm made him feel... twitchy. Like he was dangling over a cliff with no rope.

And worse: he was so keyed up that even his emotions were starting to spiral. Just like every time this happened. The same ridiculous cycle. Horny. Frustrated. Self-loathing. Repeat.

He leaned back up, thumbs tapping.

“i’ve already edged for over 30 minutes and nothing. i can’t wait longer. what else is there?”

The bot responded again.

“Some people find combining toys provides better results. If you’ve already tried the vibrator and prostate stimulator, you might consider combining one of those with internal stimulation from a dildo or anal plug to create pressure and depth. This can intensify sensations and help push you over the edge.”

He stared at the screen. Of course it said that. Of course the answer was that.

Penetration.

He didn’t want to go there. That was the line he’d already tried to draw. Repeatedly. And each time the line blurred, smudged, got redrawn somewhere softer.

This was supposed to be about pleasure. Not... giving in.

Still, the thought wouldn’t leave him. His cock—what was left of it, locked and caged—gave a tiny, involuntary twitch. His thighs clenched tighter.

His fingers hovered over the keyboard again, asking for more detailed instructions. But when the AI response came back to him with mentions of a vagina, he had to pause and clarify.

“i don’t have a vagina. i’m not a woman. i’m... a sissy. or trans maybe. biological male.”

The shame of writing it down made his face flush.

He hated that the words felt _true _and _not _true at the same time. Neither option felt like home. He wasn’t a woman. He was a man. But not with the way his body moved, the way his voice softened on calls, the way he sat, walked, breathed.

The bot responded again.

“Thank you for clarifying. For biological males using penetrative toys, pleasure often comes from direct prostate stimulation. Using a dildo or plug in combination with a vibrator on the perineum or cage can replicate full-body stimulation. Try inserting the dildo with lube slowly, letting your body adjust. Once it’s in, begin with shallow thrusts while keeping the external vibrator pressed in place.”

Kieran’s stomach twisted. He reread the message twice. Then again.

It wasn’t graphic. It wasn’t dirty. It was just... clinical. Helpful.

And somehow that made it worse.

This was normal now?

Instructions for how to fuck yourself with a dildo just casually offered up like he was supposed to already know this?

He set the phone down beside him, arms limp, vibrator still buzzing between his thighs, stimulator still rotating inside him.

His body felt soft. Weak. Sensitive in ways it never used to be. His thighs, parted like this, looked almost... feminine.

He looked feminine.

Every time he saw himself like this—no forms, no blouse, just soft satin and flushed cheeks and wide eyes—it made it harder to lie to himself.

And harder to believe there was still a line left to protect.

He sighed. Then reached for the drawer.

Kieran opened the drawer with a kind of slow, bitter resignation. His fingers—smooth, soft, lightly moisturized, tipped with neat almond-shaped nails—curled around the base of the smallest dildo.

It was silicone. Anatomically correct. Unmistakably a cock.

Not a toy. Not a wand. Not a vibrating dot or a heart-shaped plug.

A cock.

Even at its smallest—maybe four inches long, narrow, gently curved—it made something inside him clench with disgust. The weight of it in his hand wasn’t much. But what it meant was crushing.

He turned it over slowly, examining the molded veins, the flared head, the base designed for gripping. The silicone was soft and warm from the ambient heat of the room. It flexed slightly in his grip, like it was ready for something he still refused to imagine.

It didn’t matter that it was the least intimidating of the three.

It was still a dick.

Still the kind of thing he’d mocked in porn. The kind of thing girls on cam shows rode with giggles and fake moans. The kind of thing that no real man should ever be on the receiving end of.

And now here he was.

Naked from the waist down, vibrator buzzing weakly between his thighs, ass stuffed with a rotating plug, hair tousled, chest rising and falling in a slow, feminine rhythm.

Looking down at a fake cock in his own hand. The same hand that had once wrapped around his own dick with pride. Confidence. Masculinity.

He felt sick.

He dropped it back into the drawer like it had burned him, pushing it behind the other toys as if putting it out of sight might erase what had just happened. The quiet thump of silicone against velvet lining felt humiliating in its own right.

There was no way. Absolutely no way he was ever going to fuck himself with a dildo.

That wasn’t even a slippery slope—it was the bottom of the pit. The final betrayal. The most emasculating outcome imaginable.

If that was the line, he had just looked over the edge and flinched.

He grabbed his phone again, hating how shaky his hands had gotten.

“ok i’m not using the dildo. what else can i do?”

He fired the message off to ChatGPT, already bracing for the reply.

It came quickly, as always.

“Of course. There are other ways to increase arousal and deepen sensation without using penetrative toys. Here are a few suggestions:

- Focused edging over longer time periods (hours, days) to build more intense eventual release.

-Temperature play (warm oils or cool compresses).

-Sensory denial (blindfolds, light restraint).

-Cum play or visual stimulation from previous release.

For some sissy/trans individuals, increased arousal can come from dressing up or leaning into feminine expression—feeling ‘doll-like’ or ‘pretty’ can amplify the submissive mindset and make orgasm easier.”

Kieran stared at the screen, jaw tight.

That last one.

“For some sissy/trans individuals, increased arousal can come from dressing up...”

His thumb hovered over the screen like it might erase the words.

It wasn’t that it shocked him. Not anymore. He’d lived in dresses and heels for weeks. His lingerie drawer was more organized than his suits had ever been. His makeup routine had twenty steps more than his skincare ever did.

What caught him off guard was that—out of all the suggestions—that one didn’t sound as bad.

He didn’t want to admit it. Not even to himself. But the thought of putting on something delicate, painting his lips, curling his hair, even slipping into a tighter corset... it didn’t make him recoil the way the dildo had.

Not because it wasn’t emasculating—it was.

But because it had become familiar. Routine. Safe, even.

He sat in silence for a long moment, the toys still gently buzzing against his body, the sensations warming his thighs and pressing into his core but still not tipping him over the edge.

The other options played through his mind.

Option A: Edge for hours or days, letting the tension build until he either snapped or broke. He’d done that. It made him weepy. Unstable. Useless.

Option B: Use the dildo. No.

Option C: Keep doing what he was doing. Go insane. Useless.

Option D: Dress up. Embrace it. Become Kiara.

He clenched his jaw. It was almost the one he hated most... because it was the one he could actually imagine himself doing.

And that made it worse than all the others.

He groaned into his pillow and squeezed his thighs tighter. The vibrator pushed deeper into the cage. The plug buzzed harder. His breathing hitched—but the orgasm still wouldn’t come.

There was no answer. Just choices. And every choice brought him closer to a truth he still wasn’t ready to face.

Kieran let out a long, quiet breath as he reached down between his thighs and gently pulled the vibrator away from the cage. It was still humming softly in his hand—warm from use, slick with the faint sheen of sweat. He turned it off for now, setting it on the nightstand with care.

The prostate stimulator stayed where it was, but now on a lower setting.

It had become a second pulse inside him, a quiet churn of pressure and vibration just beneath the surface. Every tiny twist of its rotating head sent a deep, dull pleasure rolling through him, like a whisper of something more. Not enough to get him off. But impossible to ignore.

He set his phone aside next. No more questions to ChatGPT. No more searching for answers in between his moans. The answers were already clear. What mattered now was what he chose to do with them.

He slid out from beneath the sheets, rising from the mattress slowly. His legs wobbled slightly—partially from the plug, partially from the lingering tension of arousal that had nowhere to go. The soft rustle of satin whispered against his thighs as he reached down and slipped off his nightwear: the pale pink bralette, the matching panties, the satin shorts.

They fell to the floor in a quiet heap.

Standing now in only the cage and the warm flush of his own skin, he padded barefoot across the room to the wardrobe—feet close together, hips naturally swaying in that soft, trained rhythm that still made his stomach turn whenever he noticed it. Even when he was alone, he moved like her.

His fingers skimmed across the hangers until they found what he was looking for: a black lace lingerie set. More decorative than practical, thin and sheer, it left very little to the imagination. He’d never worn this one—not in a serious way. Celeste had picked it out and made a joke about how every girl needed a “private show” set.

Tonight, it wasn’t a joke.

Kieran stepped into the panties slowly, pulling them up over his hips with both hands, letting the lace stretch and hug the smooth line of his waist. He adjusted them to sit just right—flatter in front, tighter in back.

Then came the bra.

He clasped it behind him with ease—he’d had enough practice by now. The cups hugged the adhesive silicone breast forms he pressed into place moments later. They weren’t skin-toned. Not exactly. The edge where form met flesh was subtle, but visible if you were looking for it. Still, the shape they gave him—round, soft, perfect—was undeniable.

He paused in front of the mirror.

That might’ve been enough. The black lace against his pale skin. The slight bounce of breasts when he shifted. The way the bra lifted and curved everything into something feminine.

But it wasn’t. Not tonight.

He could still see the edges of the silicone inserts, the faint artificial divide between what he was and what he looked like. It bothered him more than it should have. He couldn’t unsee it.

He turned, walked back to the wardrobe, and pulled out a white T-shirt.

Not tight. Not loose either. Just snug enough to suggest the curves underneath. When he pulled it on over his head, tugging it down over the bra, the shirt clung just enough to frame the swells of his fake breasts.

He looked at himself again.

A girl.

A girl with nice tits.

The kind of girl who could post a thirst trap from the waist up and break a thousand hearts.

And yes, the cage was still on. His pants were still off. But with the shirt on? The fantasy didn’t break. It framed it. Enhanced it.

Kieran considered grabbing shapewear. The high-waisted nude compression briefs that gave him that smooth, tucked hourglass silhouette. But he paused. He’d have to peel them off afterward. They’d get... wet. Sticky. Maybe worse.

He didn’t want to be caught cleaning cummy shapewear. So he skipped it.

Just the shirt. The lace. The breast forms. The plug.

And now... the makeup.

ChatGPT had suggested dolling up. Becoming pretty. Fully embracing Kiara.

Kieran walked to the vanity—still flushed, still plugged—and sat down on the velvet stool in front of the mirror. His thighs pressed together, and with the perfect amount of tension, he slipped the vibrator between them again, just under the cage, and clenched.

It was back. That steady hum. Buzzing against the steel, against the skin.

The stimulator inside him responded with another twist, another push.

His hands were free now.

It was time to focus.

He reached for the primer first—Euphorica’s own. Silk Veil. He applied it with gentle, practiced swipes across his cheeks, chin, forehead. Then came the tinted moisturizer, patted in with a sponge. Just enough to blur imperfections. Just enough to glow.

Blush next—something warm and flushed. Then contour, light and clean. His cheekbones sharpened. His face softened.

Eyes. He chose shimmer: champagne on the lid, a darker bronze in the crease. He flicked eyeliner in a small, deliberate wing. Mascara. His lashes were already full, but he layered anyway.

Then his lips—his favorite part now, though he’d never say it out loud. A pink-nude liner, then a glossy stain in a dewy rose.

He looked up between steps. His reflection was building.

No, _she _was building.

The girl in the mirror was flushed, aroused, pretty. Her thighs were bare. Her chest was full. Her lips were kissable. And her breath was shallow, barely audible above the soft buzz of the toys still working her body.

It had taken him fifteen minutes. And now she stared back at him.

One sexy girl, her pants off, her lips perfect, her toys buzzing, now turned up to the highest speed.

Kiara.

He probably would’ve cum while applying the lipstick if he hadn’t been concentrating so hard. But makeup was sacred now. Too important. It demanded precision.

But now?

Now there was nothing else to distract him.

Only the girl in the mirror.

Only the toys in her body.

Only the pleasure left to chase.

The mirror glowed softly under the vanity lights, haloing Kiara in a warm, golden aura. She sat back on the velvet stool, legs parted just slightly, enough for the hem of her white T-shirt to fall between her thighs, just enough to frame the image reflected before her. Her lips were plump and glistening, perfectly painted in a rose-pink sheen. Her cheeks glowed with blush. Her eyes shimmered, lined and feathered in browns and golds.

She looked flushed. Breathless.

Beautiful.

And she knew it.

The vibrator buzzed steadily between her thighs, trapped there by the perfect tension of her legs—her knees slightly turned inward, her ankles angled like they’d been trained to pose for a photo shoot. Her bare thighs trembled with every pulse, muscles tightening unconsciously every few seconds. The prostate stimulator, still snug inside her, rotated with a patient, mechanical precision, curling inward at just the right angle. It worked her from the inside, slow and deep and relentless.

It had taken her over half an hour to get here.

But now?

Now she felt full. Saturated. Every part of her was primed and aching. Her nipples, hidden under the lace of the bra and the thin cotton of her shirt, throbbed with sensitivity. Her skin was hot. Her breathing had become soft, shallow, almost rhythmic.

Her thighs tightened a little more. The vibrator pressed harder. The stimulator pushed deeper.

A wave rolled through her.

She let out a quiet gasp—soft, delicate. The kind of gasp a girl might make when trying not to be too loud, too needy. But the sound still escaped, uninvited and entirely true.

She kept her eyes locked on the mirror. The girl staring back at her was Kiara. Not Kieran playing dress-up. Not the boy beneath the paint.

This was the girl who got off to her reflection.

This was the girl who needed toys to cum.

This was the girl who moaned when her thighs rubbed just right.

This was the girl who looked pretty even when falling apart.

Her hips gave a tiny thrust forward—subtle, barely more than a pulse—but it pushed the plug into just the right place. Her whole body jolted. The vibrator buzzed right against the base of her cage, the metal humming against skin slick with arousal.

Her legs tensed. Ankles crossed. She couldn’t breathe.

The orgasm was building again. Faster this time. Heavier. Like the first one she’d had all those nights ago, but stronger—charged with weeks of frustration, nights of failure, and now… complete surrender.

There was no part of her resisting anymore. She didn't think about what this meant. What Kieran would say. What lines were being crossed.

Kiara didn’t care.

She rolled her hips again. Another gasp. Her fingers curled against the vanity table. She felt her body shudder.

She was going to cum.

The mirror blurred with tears. Her lashes fluttered.

She kept staring anyway. She wanted to see it happen.

Her thighs clenched tighter, the vibrator humming like a second heartbeat. The plug inside her twisted again—one perfect rotation.

And then—

Her whole body broke.

The orgasm ripped through her like lightning.

Every muscle in her body locked. Her mouth opened in a silent cry, too overcome to scream. Her stomach clenched, hips grinding instinctively forward, lost in rhythm.

And then she felt it.

Hot. Messy. Cum.

Spurting through the cage in tight, pulsing ropes.

Splattering against her inner thighs, her seat, dripping down over the edge of the stool. Her body convulsed, back arching, toes curling, knees trembling. Her arms pulled inward, hugging herself through the explosion as her vision blurred and her reflection disappeared in a haze of light and pleasure.

The pleasure didn’t stop.

It poured through her. Again. And again.

A full-body detonation.

She felt it in her scalp. In her fingertips. In her chest. She moaned, finally—a long, breathy sound. Feminine. Helpless.

The kind of moan you couldn’t fake.

When it finally ended, she slumped forward slightly, arms limp, breath hitching as aftershocks rolled through her legs.

She blinked slowly. Her chest rose and fell. Her shirt clung to her now—damp in places, stretched across the swell of her fake breasts.

The vibrator slipped from between her thighs and rolled to the floor. The plug still buzzed inside her—faint, satisfied, almost purring.

And Kiara just stared at herself.

Cum was drying on her thighs. Her makeup was perfect. And she looked more like a girl than she ever had.

More than that…

She looked happy.