Work Text:
6:03 PM
On a Tuesday
Philadelphia, PA
“This is for you.”
Charlie swallowed nervously.
“Come on, Dee, do you really think I need that thing? You know you can just…whenever you want…ah come on.”
You know I can’t come close to resisting you whenever you want me. I’ve got you covered, say the word.
That’s what Charlie wanted to say to the most beautiful woman he’s ever known, but he fell silent and unzipped his pants anyway as she approached him. He cheeks reddened and his breath hitched when he saw the object in her hands. He’d submit to anything, no matter how painful it might become.
***
About 6 months previously
Moments into their first kiss, she quickly leveraged control. Charlie fell back into the loveseat, pulling her on top of him, clawing at her back and drawing her legs closer around his with his strong, rough hands. She’d quickly pinned his shoulders back with both hands before wrapping her fingers through his soft hair and pulling. She broke their kiss and glared into eyes her usual intensity, but this time something else was present as well. A fierceness.
He swallowed and lowered his eyes, not lacking in his want for her but all at once feeling shy about being with someone so powerful and beautiful. She grabbed his chin roughly and kissed him hard with open eyes, nipping at his bottom lip, and he knew better than to break that eye contact a second time.
Having established their roles, she gasped orders at him for the rest of the night. He figured why not, this is just tonight, right? He really just wanted to give Dee her way, since after all she had (significantly) more experience than him...and besides, he felt so happy that she'd been nice to him all day and wanted to make her happy too.
“Don’t you dare think about coming until you’ve made me scream your name.”
But it wasn't a one time thing. The next day, they carefully skirted around each other at the bar and laughed out some bland insults, but every time Dee came close, Charlie felt the hairs on his arms stand on end.
“Do you like how I made you feel? You liked having a sexy woman put you in your place, is that it?” He did.
It happened again. And again. He was physically much stronger than she was from decades of manual labor, but she towered over him in a way that made him feel dizzy with need (especially in those sexy high heels she took to wearing). He gave up control again and again.
“On your knees. Now.” God how he loved hearing that.
The sunshine made halos around her golden hair, and so he worshiped her. She possessed a confidence he’d never had so he followed her like a puppy. She started taking smoke breaks at work so he slipped out after her one day, making needy eyes at her until she pulled another out of the pack, placed it between his lips, and lit it for him. At some point along the way, Charlie had offered himself up to her completely...and she’d accepted.
***
Present day
On this particular night, the whole gang decided to treat themselves to dinner at Guigino’s. They'd just passed another health inspection, they’d made a few bucks pulling off a scam, and were feeling celebratory. Charlie did his best to gussy up at home, pulling on most of a suit he found in the back of his closet.
Dee had instructed Charlie to come to her apartment first before going to the restaurant. When she’d called that afternoon, Charlie got the sense something was up. He didn’t have great intuition but her voice was heavily laced with plot. She got off on control, but how could that fit into dinner?
So, it surprised him when she approached him with a severe-looking cockring. Notably, she was also wearing an incredible, chic, form-fitting dress with a deep V neck showing off the inner curves of her breasts. Three-quarter sleeves, hem midway up her smooth thighs. She was evidently not wearing a bra. Charlie stuttered out his little protest, but the temptress before him interrupted.
“It’s not because I think you can’t keep it up, dummy. I know I could get you desperate in a supply closet any time I damn well please,” Dee replied simply. “Nope. This sonofabitch vibrates.”
“It...what?!” Charlie was pretty practiced in self-control because he let Dee routinely decide when and how he was allowed to finish. “That thing is just gonna vibrate through this whole dinner and I’m supposed to just…”
Dee smirked, cocking an eyebrow. She held up a small remote control. “Not at all, sweet thing. I can turn it on and off as I please. I am going to use this to get you so close to the edge you’ll lose your goddamn mind for me, until we finally get home. Then, if you’ve behaved yourself, I’ll consider doing something about it.”
...This wasn’t an empty threat. She’d tied him up and left him desperate and alone for more than an hour at a time before, a plug shoved up his ass and nipples clamped. It was so hard to get through, but it was also so good, and it was always beyond worth it for the way she took care of him at the end. He...he liked making her proud, even when it meant satisfying her cruelest and most sadistic urges.
But this is absurd, Charlie thought. Sitting next to Mac or Dennis or...ew, Frank...in this state will be a fucking nightmare. Despite himself, he was already getting hard over the idea of being in public with a filthy secret. The risk was really fucking hot, actually. And a little depraved...right up his alley.
Dee got right up to him, dangling the device right before his eyes, and he could feel the heat radiating between them.
“So? Wanna do this? Will you be a good boy for me?”
He nodded quickly and pulled down his underwear. She stroked him unnecessarily because his racing heart had already pumped most of his blood directly to his swelling cock.
She clamped the device around him: a thick ring fit snugly around his base with a vibrating bullet at the top, and another strap squeezed around his balls, nestling a second vibrator right behind them by his taint. He throbbed in her hand as she finished with him, giving him a final stroke before examining her handywork.
God, did he get off on the way Dee was looking at him. On being at her mercy. On the idea that maybe he wouldn’t even be allowed to have any release after this was said and done.
(Holy fuck will I scream and pout if she does not let me cum after this.)
She pressed and held the button on the remote for a moment, testing it out. Charlie grunted in surprise and closed his eyes when quiet vibrations shot through him and tightened something in the pit of his stomach.
Dee smiled pleasantly. “Perfect. Tuck yourself up in the waistband of your underwear and it shouldn’t be noticeable. Nobody will even be able to hear it. We’d better get going.”
***
The gang was given a great table in the middle of the restaurant. Dennis and Mac had dressed to the nines as well -- Mac adding a tie to his cleanest polo t-shirt and Dennis in a narrow-cut navy blazer. Frank had worn his dress toupee. Candles, real silverware, long white tablecloths, a way nicer setting than their normal digs, and the lively spirits of everyone around Charlie suggested an otherwise easy-going night.
But right after they ordered, Charlie felt a sharp pressure and saw Dee smirking at him from across the table. She’d extended her leg and pressed the toe of her shoe right up against his restrained cock. It hurt in a good way and he concealed a grimace.
So that’s how she’s going to play it. Charlie downed his drink and narrowed his eyes at her before forcing himself to turn back and laugh at something Dennis had just said.
Bzzzzt. Charlie gasped audibly as their food arrived and had to pretend he was fucking blown away by the sight of piping hot spaghetti.
“Don’t mind our friend, he’s a bit of a simpleton.” Dennis shooed away the waiter. “Two more bottles of wine, thanks.”
Throughout their dinner, featuring a mixture of jackass debates and putting on high-society airs Charlie would barely remember, Dee sent a steady series of vibrations running through Charlie’s pants, sometimes nudging him with the toe of her stiletto. His mind was swimming. She leaned over the table as she chatted with everyone, showing off her breasts and leaving little to the imagination.
Charlie sat still as well as he could though he was sure a vein was popping out of his forehead from the strain. A particularly long vibration as their plates were cleared away, and that was it. He felt himself beading over with precum. He repeatedly adjusted himself to make sure he was still tucked up, so instead of leaving a wet spot he began soaking the waistband of his boxer briefs.
God damn it. Charlie was more than used to holding an erection as long as Dee wanted, but this was torture.
Dee got up to use the restroom and after another minute Charlie knocked back the rest of his sixth...seventh glass of pinot noir with white knuckles and choked out a laugh, “You’ll have to excuse me gentleman for I must break the seal, as they doth say in the plebian realm.”
What the fuck was that. Whatever. He ducked between the tables making his way toward the bathrooms and rounded the corner into the dark hallway just in time for Dee to emerge.
He immediately brought her up against a wall, hands feeling down her slender neck and back, up the front of her dress to squeeze her breasts, and pressing himself into her as he kissed her. He pulled back enough to mumble “Okay Dee, this has been fun, but come on…”
He panted against her, kissing her neck and pulling her hips into his, pressing his desperation into her inner thigh, until she shoved him away. She flipped them around and pushed Charlie’s back into the wall, grabbing his cock and squeezing.
“Dee…” Charlie closed his eyes tightly and whimpered, afraid that if he laid eyes on this gorgeous woman he’d lose control.
“Hell. No. You know the rules, bitch. At least I thought you did. And now, for the rest of the night, you’re going to address me ‘ma’am’. Mmm kay?” Charlie peeked open one of his eyes. “and you better get it together or this…” she gestured between them, “isn’t gonna happen tonight. Got it?”
Charlie nodded, biting his lip. Of course he could say “no” and that would be the end of it. She knew enough about his past not to force him into anything beyond his limits. Luckily enough, when it came to her...Charlie didn’t seem to have any goddamn limits.
“Yes, ma'am. Th...thank you, ma’am,” he added, emphasizing his submission.
His forehead glistened and the effort he’d made at combing his hair earlier had totally dissipated. He was a wreck.
“Good boy.” She turned and sauntered away, before turning back slightly.
“You know, this is a really good look for you.” She bit her lip and looked him up and down before adjusting her skirt and disappearing around the corner.
***
The rest of the dinner was agonizing. Charlie doused his senses in wine, attempting to dull the sensations in his groin...but the control Dee continued to exercise over him was utterly sobering, grounding him in the reality of the throbbing erection he continually worked to hide.
“Alright bozos! What now, strip club?” Mac drummed his hands against the table and looked around at them expectantly. His eyes shone with his typical childlike eagerness.
“Yeah, totally man. What about you guys?” Dennis bumped Mac’s knuckles and turned to the rest of them.
“Ach, not me. The ol’ lady is expecting me at a certain hour in a certain uh, alleyway.” Frank was talking about Artemis, and he was talking about a dumpster behind the Wawa. They didn’t push him for details.
“Yeah, me neither, I’ve gotta ahhhhhh…” Charlie barely covered it up as Dee sadistically interrupted with a long vibration shooting through to the head of his pre-cum-smeared cock.
“I’ve gotta meet up with my spy, actually. Says he got some big developments for me, you know how it is.” Charlie had continued to keep up the charade that he was stalking the waitress to keep the gang off their case.
“Deeee??” Tipsy Dennis and tipsy Mac leaned across the table toward her.
“Are you serious? Hell no. No way am I watching you boners ogle breasts and creep on ladies all night. I’m out.”
“BOYS NIGHT OUT!” Mac and Dennis high-fived.
“Whatever. Good work tonight though, gang, I feel like we really upped our classiness levels. No shouting, nothing. Salud.” Dee raised her glass.
“Salud,” they said in as solemn and dignified a manner as possible. Everybody drained their glasses and parted ways.
***
Charlie wanted to take advantage of being alone the moment they got in Dee's tiny little car but he resisted, knowing what the consequence could be. He sat still as she looked into him with smoldering eyes and delicately ran a hand along his inner thigh to the length of his dick. Charlie moaned loudly, no longer needing to hide the delicious agony he was in. He strained against her touch. Charlie had never felt so...much.
For her part, Dee was pretty worked up too. She'd become fairly wet during dinner as she used the vibrator on Charlie again and again, watching his mouth fall open or his jaw clench. He'd purse his lips and exhale heavily through his nose to try and regain his composure -- it was sexy as hell.
Now, with his head tilted back against the seat and his face silhouetted by a street lamp, hips bucking under her touch, she thought he'd never looked hotter. She re-positioned his dick so it was no longer tucked into his waistband but instead tenting painfully against his zipper. She became aware of herself soaking through her own underwear, but ignored it and traced the palm of her hand in little circles around the head of his cock. The fabric of his pants quickly gained a large wet spot. Charlie shivered and whimpered...all under her control. She could make him do anything. He would do it.
“Ahhhhh Dee, fuck, um, ma'am...please ma'am…”
He needed to cum. He had to. He pleaded with her.
“Please ma'am, let's go, aaargh just take me home and… let me please you.” Charlie angled himself toward Dee and she allowed him to pull get into a hot, desperate kiss. She took the hand he’d placed on her thigh and guided it up her smooth skin, under her tight skirt, and made his fingers graze the wet fabric of her underwear. Charlie moaned loudly into her mouth upon feeling it.
“Is this what you want, hmm? You want to fill me in?”
“Yes, ma'am. I need it.”
“We'll see.”
She started the car and clicked on the vibrator at the same time.
“Don't touch yourself until I tell you.”
***
Charlie sort of blacked out most of the drive, channeling all his energy toward disconnecting from his unrelenting body. When he came to, he was kneeling on the floor at the edge of the bed with his face buried between Dee’s thighs, her legs draped lazily over his shoulders. He was unclothed but for the pair of underwear he’d worn under his suit...and the cockring, which was vibrating.
He felt himself pushing uncomfortably against the fabric and leaking pre-cum almost continuously...which, after hours of on-again, off-again teasing, was only fair. He found that it no longer bothered him as much. He’d managed to dissociate from the pain and focus his attention where it was needed -- the woman writhing in front of him, under his lips and tongue. She still hadn’t given him permission to touch himself, anyway.
Her dress was simply hiked up around her waist, so when Charlie glanced up he could see her breasts rising and falling just barely covered by the thin fabric. Her head was thrown back, one hand bunched up with a knuckle between her teeth and the other gripping Charlie’s soft hair. He definitely wouldn’t boast about it, but...
Yeah, I must be real fucking good at this. Dee arched her back as he flattened his tongue and gave her clit several long strokes while slipping one of his rough fingers inside her. She was as wet as he’d ever felt her, but he basked in how her juices covered his face as he switched between circling her clit with his tongue, flicking it, and sucking it between his lips.
Sweet Dee indeed.
It also drove him wild how readily she accepted a second finger into her tight wet warmth, then a third -- she was ready for him, she must be.
“Ah, Charlie, stop.” She pulled him away by his hair, uttering profanities, and he sat back on his haunches, waiting.
“Yes, ma’am. What, ah…”
“I’m real goddamn close, but first I want to feel you. Deep. Stand up.”
Charlie scrambled to his feet as she rose to hers to pull him into an unexpectedly sensual kiss. She pulled her dress over her head, dropped it on the floor, then eliminated any remaining space between their bodies. Charlie had been right -- no bra. He felt weak as she pulled him close, felt her sweat and her heartbeat, and tasted her tongue...knowing she was tasting herself, too.
His moans rumbled as deeply as his voice could reach as she grinded her hips against the aching cock pressed up between them.
“I want you to fuck me, but you can’t cum. Not until I’m finished, and then I’ll tell you how I want you. Can you do that?”
She tugged his hair tightly and clawed her nails across the back of his shoulders, definitely leaving her mark on him. Charlie nearly sobbed at the sensation.
Yeah, we’ll see…
“Yes, god...yes ma’am,” is what he actually said. “Whatever you want, you can have. I’ll give it to you. Please...ma’am, please let me fuck you.”
“You sound fucking desperate. You’d do anything I say just to make me cum, wouldn’t you, slut?”
Charlie nodded into her neck, eyes closed, licking and sucking and biting at the sensitive skin there. Not this time. “Yes ma’am.”
“Better make it good.”
A green light, he decided. With an almost inhuman growl he lifted her off her feet, throwing her back onto the bed. He tugged down his underwear and his cock sprang free, flushed with deep purple and red from the torture of being kept in this state for so long. He assumed a position on top of her and lifted one of her angelic legs to place it over his shoulder. He leaned in to kiss her quickly before lifting his head so he could look into her eyes as he thrust into her in one smooth motion, burying himself deeply so that the vibrations of the ring pressed directly against her skin.
Charlie was fairly large, and Dee was pretty tight so she smiled wickedly as he nearly screamed at that first sensation. Literal hours had passed since she first got him completely hard and strapped this tight ring around him -- it had restricted blood flow, keeping him hard, plus practically tortured him with sensation. She knew this had to practically hurt right now.
But she stopped thinking about his state as he rocked his hips outward before gliding back in, slowly developing a rhythm and lifting her hips to a certain angle in order to brush against that sensitive spot inside her.
“Fuuuuuuck. Yes, Charlie. God, just like that. I could come so easily if you keep this up.”
As he rocked into her, Charlie had pressed his forehead into the skin at her collarbones, breasts, neck, and finally earlobes, and while he nibbled them she noticed he was muttering incoherently. She couldn’t make out much, but couldn’t blame him if he was delirious at this point.
“Okay, fuck yes, now touch me, and don’t you dare stop until the neighbors can hear us.”
Nah. No, thanks.
Charlie grabbed her other leg and lifted it over his shoulder, forcing her into a more vulnerable position, more exposed. He now whispered into her ear so she could understand, pumping her with slow but forceful thrusts to emphasize his words.
“I’m in so much pain for you, Dee Reynolds. And you love it. You have all of me at your beck and call. But you’re fucking filthy for making me feel this way.”
Dee whined softly. Charlie didn’t usually talk back to her, or disobey orders much, but this change of the current made her feel hot.
“Plus...you’re a fucking slut too, aren’t you? You get me so fucking desperate and just leave me panting over you. You beautiful, depraved fucking cocktease.”
“Charlie, what? Okay that’s ma’am to you...Get your hand down there and…” She felt her heart beating in her clit at his words, but steadied her voice to regain control over him. He was going to make her cum, thrusting into her hard and fast, fingering her with his calloused thumb. This was what was going to happen next. And then she’d have to fucking punish him for talking to her like this.
“How about instead I give you a little taste of my night.” Not a question. He grabbed both of her arms and slid them up over her head, pinning her there. He slipped her wrists together so he could hold them there with one strong hand, leaving the other free to roam her body.
He was beginning to really feel a throbbing ache, unsure of how much longer he could keep this up himself...but it was worth a little more pain to get Dee desperate.
“Hey, maybe I could even just leave you here like this, and you’ll get nothing.”
He punctuated “nothing” with a deep, sharp thrust.
“I could just...bind your wrists and like...make myself cum all over you, and walk away.”
“You wouldn’t dare…” Dee wasn’t sure of that, but she didn’t tell him to stop. (And he would have stopped, for the record.) He was picking up the pace, pounding into her at an angle that made the vibrations stimulate her clit directly. She whimpered, rocking her hips upward, desperate for more, so close but unable to bring herself there.
“I wouldn’t be to sure about that, sweet Dee...it would be so easy to send you over the edge right now, you’re so goddamn needy for it, but at the same time, like, I don’t have to. You know?”
His breath hitched at the end and he felt a threatening amount of cum spill prematurely from the tip of his cock. He clenched his teeth and slowed his thrusts, rolling his hips very intentionally and hitting that spot inside Dee each time.
She was getting loud by this point. Whining and moaning, eyes clenched shut...Charlie stared down at her with fascination. He had never seen her this way; this was always how she saw him. Interesting.
“Please…” she said finally, almost inaudibly.
“I beg your pardon?”
“Isn’t that what you want? Do you want me to beg for it? Please don’t leave me hanging, I’m so close…”
“Hmmm…”
“PLEASE, Charlie!” she sobbed. “I need you, please touch me, okay? You’ve been so fucking good for me all night, now please make me cum.”
There it is. That'll do. “Yesss ma’am…...”
Charlie sped up again, knocking the headboard into the wall. He moved his hand down from her breast where he had been pinching her nipple and began swiping his thumb across her clit, then used his thumb and forefinger to lightly pinch and stroke around it. He didn’t think he’d be able to keep himself from coming once she began to scream and tighten around him, but he realized --
“Dee, fuck uh...can I come too?”
A minor flaw in his plan -- he couldn’t remember ever, ever finishing without her permission before. He wondered if he was physically capable or if he’d just sit there on the edge of exploding.
“What?! YES, YOU IDIOT. Oh god, oh fuck--!”
She threw her head back as the waves of orgasm began to hit her. She shouted his goddamn name. Charlie continued stroking her clit but released her wrists and used that arm to pull her in close, feeling her spasm before a lightning bolt of hot pain shot through his cock as he finally relaxed a muscle he’d been clenching for hours.
“OH MY GOD, DEE--” He bit down on her shoulder as he shot once, twice...four or five(?) times, pumping his hot fluids deep inside her.
They laid there for a minute, shivering through the rest of their orgasms (and Dee immediately seized the remote for the cockring from her bedside table and ended that torture). Finally, Charlie pulled out and, propping himself on one elbow yanked the contraption off himself. Red marks almost like welts remained in the skin of his softening cock.
Instead of rolling over next to her, he scooted down on the bed, curling up between her legs and laying one head on her thigh.
“I’m sorry, ma’am.” he whispered. “I wanted to make you feel good, and make you desperate, and make it so intense...but I know disobeyed you. I’m sorry. ” Dee knew Charlie took their play very seriously. His voice was fucking quivering.
“Charlie, you idiot. Come up here.”
He crawled up and waited for Dee to wrap an arm around him, hold him against her chest like she always did. Instead, she patted the bed next to her and he laid back, and she put her head on his chest. He sighed and pulled her in close, burying his nose in her sunshine hair.
“It’s actually pretty impressive that you went so long before snapping like that,” she mused.
“Yeah, well...I guess you definitely put me through the ringer for the last couple months, had me training up for it.”
They chuckled together, breaking character for a moment, sounding like the friends they’d been before shit got quite this weird.
“It wasn’t so bad. Having you on top like that. That being said…” Dee lifted herself and perched on one elbow, looming over him, and the tone of her voice turned stern. “I will be planning a punishment for this. You broke the rules. And if you ever do that again, I swear to god…”
Punish me.
“I know. I know.” Charlie pressed embarrassed kisses to her forehead. “I don’t even, like, want to. I won’t. You’re the boss.”
“Damn right I am.”