Truth or Dare: First Time

I'm discreet--never met anyone in person, just played online with toys when I travel. I make a ritual of it: taking requests for gear and using a cheap smartphone I use for Snap, Skype, whatever. Lately, I've been downloading Grindr on it, scoping out who's local.

Tonight, I'm in my hotel room, naked on the bed, gear spread around me. I'm chatting on Grindr with a couple who, turns out, are in the same hotel, just a few floors away. They're scheming to get me down there, but I'm not budging.

"Let's play Truth or Dare," they type.

"Intrigued," I reply. "Okay. Dare."

"Cage up your cock."

I grab the base of my chastity cage, slip my balls through, then my flaccid cock. Fitting the cage over it, I press it snug and lock it--pinching a bit of skin, but I manage. I send a quick video.

"Good boy," they reply. "Truth."

"Have you two ever spit-roasted a guy?" I ask.

"Yeah, a few times," they say. "It's fun. Last time was a couple weeks back."

"Cool. Truth."

"You really never met up?" they ask. "All that gear for a virgin?"

"Nope, just toy exploration," I type. "Not that I haven't thought about it ;)"

"Ah, got it. Dare."

"Send a pic of both your cocks--hard--right now."

Minutes later, the photo lands. They're massive--8.5" like me. One's uncut, the other cut. My cock strains in its cage.

"Yummm" I type. "Dare,"

"Put your tail plug in."

I lube it with fake cum, ease it into my hole. My slick hands fumble the phone, but I snap a pic of the tail and send it.

We trade dares back and forth. Soon, I'm in my jockstrap, tail plug in, cock caged, dressed over it all. They dare me to bag my gear and walk outside--send proof. I do it, wandering for 30 minutes before heading back.

"Dare," I type, stepping out of the elevator toward my room.

"We're in 1294," they reply. "Snap our door. Send it."

My heart kicks into overdrive. This is too real.

"Mmm," I send, stalling.

"Do it. Now."

I'm steps from my door but freeze. Something pulls me back. I turn, hit the elevator button. My hands shake as it dings open. Two others step in with me. I press 12, drop my phone, scramble to grab it. My pulse is a drumline.

15th floor--someone exits. 12th floor--I step out, see the sign pointing right to 1294. My steps slow. At 1292, I dig out my pup hood, glance around, slip it on, and pull my hoodie over it for cover. I creep to 1294.

Phone out, camera app loading, I hear a shuffle. The door flies open. Hands yank me inside, slam it shut. In seconds, I'm stripped to my jock, bag dumped, shoved to my knees.

A naked guy stands over me, uncut cock hard and close. "I'm Truth," he says, voice steady. He nods to the bed. "That's Dare. You're Boy."

Dare's cut, lounging, smirking at me.

"Want out? Door's there," Truth says. "Want in? Say yes--or nod."

I nod, shaky but sure.

Truth tugs the mouth flap off my hood. "Smart move."

I open wide, inviting him. He slides the head in. My lips close around it--my first taste of a man, warm and alive.

"Mmm," he hums. "Lick it. Slow."

I flick my tongue over the frenulum, then the head, savoring it.

"Good boy," Truth says, low and approving.

"Keep it up, and we'll spit-roast you," Dare calls, rolling off the bed.

"Suck it," Truth coaches. "Ease it down--steady."

I grip his base, jerking as I take more in, inch by inch. At three-quarters, I stall. His hand cups my hood.

"Breathe deep," he says. "Open your throat."

He pushes. Pop--past the barrier. I'm balls-deep, nose in his pubes.

"Hum for me, pup."

"Hmmmmmmmm."

"Mmm," he groans. "Say my name."

"Truuuugh," I choke out.

He grabs my head, hips rocking. He's fucking my mouth now--gagging me every thrust. My cage tightens as I strain. After 14 beats, he pulls out, saliva spilling down my chest.

"Stay down," he says, plunging back in.

I squirm five seconds, then relax. His cock soaks in my throat. He starts again--full strokes, in and out, gripping my head. By the sixth, I'm dry-heaving, chest slick with slime.

"Ass up," Dare barks.

I shift to all fours. He tugs my tail plug.

"Let's ditch this jock," he says, peeling it off.

"Sit up," Truth orders. "Show that caged cock."

I straighten, chest out, cage exposed.

"Good boy," Truth says, petting my hood. I clench, pulling the plug tighter.

"My turn," Dare growls, yanking my head to his cut cock.

He shoves it deep, face smushed to his abs. I grab Truth's cock with my left, stroking in sync. Dare lets go; I ease back, working his head, then deeper, drool pooling. It spills, soaking my chin under the hood.

"I'm driving," Dare says, gripping my head.

He throat-fucks me--hard, sporadic, holding me down till I gag. The plug shoots out. I heave.

"Need something bigger," Truth says, rummaging my bag. "Fuck, this haul's insane."

He grabs the largest plug. Dare shifts to the bed's edge.

"Stand," Dare says. "Suck me."

I do, swallowing him whole. Truth spreads my thighs from behind.

"Legs wide, Boy."

The plug presses my hole. Dare guides my head, syncing with Truth's rhythm.

"Push," Truth says.

I bear down.

"Release."

He pulls back.

"Push--almost there."

Pop--it's in. Dare stands on the bed, plowing my throat. Drool puddles below. Five minutes of gagging, heaving, slime everywhere.

Truth rubs the plug and my cage. I squirm--too much. I reach down; he slaps my hand.

"Mine," he snaps.

"I need a break," I gasp.

"Didn't know you talked," Dare laughs, stepping down.

"Throat's off-duty," Truth says. "Knees, bed's edge--face the headboard."

I crawl into position.

"Let's load him with cum lube," Dare says.

Fingers rub my taint, then two slip in. "He's ready," Truth says.

The XL lube launcher slides in, injects, pulls out. Twice. Then a dildo head.

"Mmm," I moan.

Dare pumps it, then yanks it free.

"Hot as fuck," Truth says as lube spills.

"My go," Truth says, loading me again.

His cock drives in. Dare's in front, throat-deep.

"This what you wanted, Boy?" Dare asks.

"Hmm mmm."

Truth fucks slow, then fast, leaning in. Dare matches him. He pulls out, balls to my face.

"Open wide," Dare says.

I suck them, jacking him as my tongue plays.

"Let's free his cock," Truth says.

"Nah," Dare counters. "He's ours tonight. Next time's his."

"Fair. Our toy."

My cage strains harder.

"All fours, middle of the bed," Dare orders.

I crawl. Truth kneels, cock taunting my face. Dare grips my hips, easing in.

They fuck both ends--balls-deep, synced. I'm leaking saliva and lube. Dare presses my back down; Truth follows. I'm flat, legs splayed, wet against the sheets.

Dare braces, pounding hard. Truth matches, wrecking my throat. Five minutes feel like 30.

Truth steps off, jacking. "Wet this," he says, sliding the Njoy wand's big end in my mouth.

I slick it. "Good boy," he says, stroking my hood.

"Break time," he calls.

Dare pulls out. Truth slips the wand in my hole. Ten minutes of prostate teasing--my toes curl, cage tortures me. I grab it; he swats me.

"Mine," he growls.

"Mount the dildo," Dare says, rigging the double-knotted toy with a syringe of lube.

I straddle it, easing down. "Working?" Dare asks, pushing the plunger.

"Get past the first knot."

I push, release, stretch--lube squirts, and I'm through.

"Wrapping up," Truth says. "Second knot, then we cum on your hood. Open wide."

I take his cock, rocking gently, eyes shut. Lube flows. I sink past the knot, full.

"Good boy," Truth says, pulling out.

"Knees," he orders. "We're painting that hood."

I rise--lube gushes out. Truth cums first, moaning, "So hot." It drips off my hood.

Dare grabs my head, unloads between my eyes. It seeps into the mask.

"Good boy," Truth says, tossing a towel. "You need this."

He packs my bag. Dare stops him.

"Spread," Dare says, shoving the tentacle plug in my hole.

"Now dress," he grins.

"Had fun?" Truth asks. "Text us."

I nod, hoodie up, hood off outside. Back in my room, horny as hell, I check my phone.

"You're not done," they say.

"?"

"Strip. Plug in. Film yourself cumming on your chest."

I shed my clothes, uncage. My cock springs free. Pumping hard, clenching the plug, I'm close fast. Phone in hand, I record--exploding over my chest, leg shaking, cum everywhere. I send it, plug still in, and crash.

Shame hits. Guilt. Disgust. But part of me loved it. I pull the plug, pass out.

Morning comes--sticky, crusted. My phone buzzes: "Good boy. See you next time."

"Hey," I type. "I'm in 2489."