Day 25: Roleplay / Glory Hole



Piers couldn’t deny, he enjoyed Annais’s idea of a date.  Sure, they still did normal couple stuff like go to movies or have picnics. But every so often, she’d get an impulsive idea and ask him to tag along.  Some real punk shit that he hadn’t done in years, like bust into an abandoned building to look for Pokémon.  

Autumn was in full swing. Nights were longer and cooler.  It was the perfect time to go on a romantic ghost-hunt.  She’d had her eye on some of the dilapidated buildings in Spikemuth, of which the city was not lacking.  She’d mentioned it to him off-hand one day, as a hypothetical situation.  It caught her by surprise when he agreed it’d be fun. He didn’t much care to catch ghosts like she did, but as a dark type specialist, he thought it would be a decent way for his team to gain some easy experience.  The last thing he needed to do was get rusty in his retirement.  He still had a girlfriend to impress, after all.

They decided to explore the old Spikemuth Pavilion Theatre.  Piers remembered his mum and pop mentioning they had gone on a date or two there back when it was still in business.  It shut down shortly after he was born and had been left abandoned since.  He’d always been curious about what it looked like on the inside, but never had someone crazy enough to sneak into it with him. How romantic was it that he and his girlfriend could trespass in the place where his parents once enjoyed their evenings?

The inside of the theatre was massive, and utterly trashed.  It looked like it had been abandoned for about five decades rather than a quarter of a century.  They hadn’t seen any Pokémon, other than the occasion Rattata, but there was tons of garbage and debris.  Piers had ended up backstage, and Annais was… somewhere.  They had split up and he wasn’t sure where she had ended up.

“Neeez!” he heard her call.

“What is it, Ann?” he yelled back.

“Dude, c’mere!”  He could hear the laughter in her voice.  “You gotta see this!”

He pointed his flashlight in the direction that he heard her voice.  He cautiously stepped off the decomposing stage and crossed the floor with his Obstagoon trailing behind.  

“Where are you?” he asked.

“Over here,” he heard her say.

“An’ where exactly’s that, love?”

She then poked her head out of a doorframe, nearly giving him a heart attack.  “Here.”

Piers followed her inside what looked to be a former restroom.  Someone had smashed the porcelain sinks, toilets, and mirrors.  Judging from the graffiti, it could have been one of the trainers from the gym.  Typical, he thought.

Annais walked into what used to be the last stall, Piers entered it with her.

“Check it out,” she said, shining her flashlight on the partition.  There was a hole about waist high, slightly bigger than the size of a fist.  “Is that what I think it is?”

“Oh wow…” Piers snorted. “Leave it to you to find these things.”

There was no denying that she had stumbled upon a bona-fide glory hole.  The tape didn’t look that old.  Based on the graffiti he just saw, he hoped that the blokes of Team Yell didn’t come here to…  No, he wasn’t going to continue that thought.

“Hey…”  Annais traced the ring of duct-taped hole with her index finger.  “Wanna roleplay?”

He stared at the hole, then glanced at her.

“Not that I don’ want to indulge in the most depraved of acts with you, my love,” he started.  “But there’s no tellin’ how filthy that thing is, Ann. Who knows who put their willy through there?  I quite like mine not bein’ diseased, an’ I think you do, too.”

“I have wipes in my bag. We could clean it first,” suggested Annais.

“Wipes…  We’d probably need to retape the whole thing.”

“… Actually!”  She squatted on the ground, digging through her bag. Within seconds, she located a roll of silver tape.  “Ta-dah!”

“Not gonna ask why you have that,” he said, folding his arms.

“You wouldn’t believe the stuff you find just laying around Galar.  I got all sorts of cool free shit.”

“Ann, I hope you’re not pocketin’ people’s things,” Piers chided.  “There’s a word for that, y’know.”

“What?  Am I supposed to just let it sit there, practically littering?” she asked with a scoff.  “Don’t leave your stuff under trees if you don’t want a trainer to end up with it. Better me than some eleven-year-old.”

“Fair enough.”  Piers held his hand out, and she put the roll in his palm.  “I can’t believe you talked me into this.”

“Talked you into this?” Annais couldn’t help but laugh.  “Nez, we haven’t started yet and you aren’t even trying to put up a fight.  You were into it from the start.”

He just laughed along with her as he located the edge of the roll, pulled it until it was a decent length, then ripped it off with his teeth.

“God, that was kinda hot,” Annais said with a giggle.

“Yeah?  You into that?  I can use it on you if you want,” he said, holding up the strip.  “Wrap your wrists?  Tape your mouth?”

Oh God…” Her breathing hitched momentarily.  “…M-Maybe later.  Can’t suck you off with my mouth covered.”

Piers laughed again and placed the piece of tape on the inside of the hole.  He repeated this a few more times until the hole was completely re-covered.

“Wipe?” he asked, handing her back the roll.  She put the duct tape back in her bag and handed him a wipe.  He cleaned around the inside of the freshly taped hole, then crumpled it and stuck it in his pocket.

“You think we should leave Ziggy out to keep watch?” Annais asked, scratching between his Obstagoon’s ears. “He can stand outside the doorframe and use Obstruct if any stray Pokémon come through.  Oni can be his backup.”

Piers scratched under the Pokémon’s chin at the same time.  “You mind? I’m sure Ann will treat you to a nice curry afterwards.”

The Obstagoon dragged his tongue across Piers’s cheek, which he took as a yes.

“Right then, out the door you go.  If you see any Pokémon, besides Oni, use Obstruct.”

“Oni,” Annais turned to her Grimmsnarl.  “If anyone gets through Ziggy’s Obstruct, use Sucker Punch.”

The Grimmsnarl gave Annais a grunt and a nod.  The two Pokémon walked outside the old restroom.

“Hope a ghost doesn’t come through the wall,” Piers chuckled.  “I know how your Gengar likes to cockblock, an’ he’s domesticated.”

“I mean, I have a Super Repel we can use if you’re that worried.”

“Might as well,” he said. “Don’ want my soul gettin’ sucked outta me by anythin’ that’s not you.”

Oh, my God.” Annais snorted, shoving him.  “Go to that other fucking stall.”

Laughing, Piers walked out and around the partition.  He unbuttoned his pants and leaned against it, pulling out his cock while waited for her. It was already half-hard.  He took the liberty of bringing himself to a full erection.

Annais took off her jacket and placed it on the ground in front of the hole, sitting her bag beside her.  She dug inside and found the repel. She peeked through to see if Piers was in position.

“Damn, that turned on by this?” she said, eyeing him as he stroked himself.

“Oi!  ‘S s’pposed to be anonymous!” he replied and stuck a hand over the hole.  “I wanted to be ready when you say go.”

“Well, I guess you’re ready? I don’t want to spray the repel until we’re starting.”

“Yeah,” said Piers.

“Okay, spraying it now.”

Piers heard the hiss of an aerosol can as she sprayed the repel in a line beneath the partition. With Annais’s high leveled team in her bag, no wild Pokémon should come close to them for a while.

“Alright…” he heard her say. “Let’s go.”

He took a deep breath. Why did he take a deep breath?  It was his own bloody girlfriend on the other side.  The atmosphere really put him in the mindset that he was about to get his cock sucked by a stranger.  He stuck it through the hole.  What now? Was he supposed to do anything?

Warm, soft hands took his cock, offering him a few playful strokes.  He took that as a no.  Fingertips then brushed along the underside, a tongue was dragged across the top, and another hand reached through to fondle his balls.  He took a step closer, pressed his body flush against the partition so he could give the hands on the other side easier access.  This was appreciated; he was thanked with a kiss on the tip.

Annais allowed her tongue to flick across the head of the cock before her, lapping the salty pre that dribbled from the slit as she caressed it.  She noted that Piers’s dick looked even bigger protruding from and taking up the majority of this hole.  Holding the shaft steady, she eased it between her lips.

This wasn’t comfortable, Piers thought.  This was one of the most uncomfortable blowjobs he’d ever gotten.  Not because Annais was doing a bad job; in fact, this was some of her finest work.  He’d much rather not have this stupid wall between them.  He’d like to have Annais’s curls twirled around his fingers and be able to see her beautiful eyes looked up at him through her lashes.  

Annais wasn’t much of a fan of it either.  She was too short for this to be comfortable.  She originally though she could just do this on her knees.  She ended up having to squat to reach him at a decent angle.  She was used to using both hands to work him as she fit as much of his huge member as she could into her mouth, but she was having to use one to hold the stall so she didn’t lose her balance.  She tried to make the best of it.  Her legs were going to be sore as hell tomorrow.  Maybe if she did a good enough job, the rest of her could be sore as hell when he got her home.

Piers realized he really couldn’t thrust into her mouth as it engulfed him and her tongue teased over the sensitive skin.  He grunted, from both arousal and frustration.  He wanted nothing more than to be fucking her throat like he’d done so many times before.

As awkward as this was, Annais couldn’t help but get turned on.  She had a bit of a Pavlovian response to tasting his cock, to smelling the clean earthy musk of his manhood.  She wanted more of him to fill her throat, but noticed he didn’t have much room to move. She found herself rocking forward to accept more of him.  She heard a moan on the other side of the partition.  Smiling to herself, she repeated this motion.  

She realized she was doing a horrible job of picturing a stranger on the other side.  His cock felt too much like home.  It was far too familiar.  She was enamored by it, and truthfully wouldn’t be enjoying this near as much if it were anyone else’s.  Her free hand began to trace the fabric between her legs as she drooled around the dick in her mouth.

Piers couldn’t help but attempt to thrust up against the hole.  He could hear her noisily sucking him off.  He drunk in the wet sounds of his lover’s mouth being so, so greedy for him. His hips bucked on their own.  If this bloody wall wasn’t here, he snarled internally, I’d wreck her fuckin’ throat.  He huffed, leaning his forehead against his paled knuckles as his arousal peaked.  His fist was balled so tight, his fingernails cut crescents into his palm.  He grit his teeth to keep from growling her name.  

He was about to cum.

She knew it.

Annais could feel the cock twitching in her mouth.  She felt the partition move as his hips jerked upward against it.  Her fingers had poked through her fishnets and found their way into her panties.  She circled her clit vigorously as her head bobbed up and down his length, causing pre-cum and saliva to stream down her chin.  Each brush of her fingertips caused her to moan.  Each moan vibrated in her throat around his length, causing him to get more aroused.  When he got more aroused, he tried even harder to fuck her mouth.  When he tried, she fingered herself more quickly.  This cycle didn’t last long.  He soon came into her mouth, and she came around her fingers while attempting to swallow every last drop.

Piers hugged the wall as his cock flooded his girlfriend’s willing throat.  His face smooshed against the cool metal as aftershocks of his climax shuddered through him.  He felt her hold it in her mouth as it grew soft.  He felt her tongue lavish it.  He groaned when the warm of her mouth was replaced by cool nothingness, then stiffened when it was replaced with an even cooler wetness.

“Relax,” he heard Annais say.  “Just cleaning you up.”

“Y’do this to every stranger you blow?” Piers asked.  He smiled to himself as she cracked up on the other side.

“Only the cute ones.”

“You’re not s’pposed to know what I look like, Ann,” he said.

“… Who’s Ann?”

“Wait, fuck,” he laughed. He pulled himself out of the hole and pulled his pants back up.  “Forget it. Roleplay over.”

“Hey.”

Piers crouched down, looking at her through the hole.  Annais leaned forward and puckered her lips.

“It’s not made for this, Ann,” Piers said, blushing.

“So?”

Piers shook his head, puckered his lips too, and met her for a kiss through the partition.

“How romantic,” Piers whispered.

Annais giggled and stood up. He got to his feet as well.

“Let’s get outta here,” he heard her say, followed by the creak of the stall door.

“Yeah.  Believe you owe Zigs some curry.”