Charlotte had always prided herself on her appearance, even if she was never quite satisfied with the results. At 35, she carried a slight more weight than she would have liked. Her dark brown hair with its subtle blonde highlights framed her face perfectly and she never left the house without a touch of makeup that accentuated her warm hazel eyes and full lips. She’d been working at her company for nearly a decade, a mid-level marketing coordinator in a bustling office that dealt with everything from ad campaigns to client schmoozing. The job was stressful, sure, with tight deadlines and demanding bosses, but the people made it bearable. Especially Harry.
Harry had joined three years after her, quickly becoming her “work husband”, that platonic soulmate who made the daily grind fun. He was 38, an ex-rugby player from his university days, always boasting about how he’d been “this close” to going pro before a knee injury sidelined him. Broad-shouldered and solid, with short-cropped brown hair that was starting to gray at the temples. He’d recently started wearing sleek wire-rimmed glasses after last Christmas, which somehow made him look even more approachable, like a rugged professor.
Their friendship was the glue that kept Charlotte showing up every day. They talked about everything: work drama, family quirks, even the spicy stuff. Outside of work, it was limited to the occasional texts, company parties where Harry had met her husband, Mike, once or twice. Mike got along with him well enough, but Charlotte noticed the subtle eye rolls whenever she mentioned Harry’s name too often. Mike was busy with his own job in tech support, always buried in his computer or gaming late into the night.
The office move had been a game changer. Now closer to Charlotte’s home on the outskirts of the city, it was right on Harry’s commute route from his. To save on bus fares amid rising costs, Harry offered to carpool with her. “Why not? Saves you money and I get someone to bitch about traffic with,” he’d said with his easy grin. Charlotte jumped at it. Their drives became the highlight of her weekdays, unfiltered chats about dreams, regrets, and yes, sex. Nothing was off-limits.
One crisp autumn morning, Charlotte slid into the passenger seat of Harry’s reliable car with a secretive smile playing on her lips. The air was cool, the heater blasting a comforting warmth, and the radio hummed softly in the background. Harry, in his usual button-down shirt that strained slightly over his broad chest, glanced at her as he pulled out of her driveway. “What’s with the grin? You look like you won the lottery.”
She hesitated, biting her lip. Should I tell him? It’s private… but it’s Harry. He tells me everything. “Oh, nothing,” she teased back, adjusting her seatbelt over her fitted blouse that hugged her curves just right.
“Come on, spill. You know I’ll drag it out of you eventually.”
After a few more prods, she caved, her cheeks flushing. “Fine. I woke up feeling… horny this morning. I woke Mike up with a blowjob, and before I could even climb on top, he popped. Like, in moments. He was all grins, saying he wants to start every day like that.” She laughed, feeling a mix of pride and lingering frustration. Mike had finished, but she hadn’t.
Harry chuckled, his deep voice filling the car. “Lucky bastard. I’m jealous.” He paused, then clarified with a wink, “Of the wake-up call, I mean. I can’t cum from a BJ. Never have.”
Charlotte’s eyes widened. “What? Bullshit. Everyone can.”
“Nope. Love ‘em, don’t get me wrong. But I prefer fucking. Being in control, pleasing back. No matter how good it is, I just… don’t finish that way.”
She felt a spark of challenge ignite. Fresh off her success with Mike, confidence surged. “I could make you.”
Harry burst out laughing, pretending to unzip his trousers. “Oh yeah? Go for it then.”
“Nooo!” she squealed, swatting his arm playfully. “But I bet I could.”
“That’s not a bet you’d win, love.” He grinned, changing the subject to the upcoming team meeting, but the seed was planted.
All morning at her desk, surrounded by the hum of keyboards and coffee machines, Charlotte’s mind wandered. Is he broken? Or just hasn’t met the right mouth? God, Charlotte, you’re married. You can’t go around giving blowjobs to coworkers. But… I know I’m good at it. Mike always says so. By lunch, she couldn’t resist bringing it up again over sandwiches in the break room.
“So, about this morning… you’ve really never cum from one? Not even with Rachel?” Rachel was his ex, the one who’d lasted two years before things fizzled.
Harry leaned back in his chair, his glasses catching the fluorescent light. “Nope. She tried everything: teasing, deepthroating, the works. Made her sad, so now I’m upfront. I like pleasing, fucking. That’s how I cum.” He smiled reassuringly. “Trust me.”
Charlotte nodded, but her thoughts raced. Challenge accepted. Not that I can actually do it… right?
Over the weekend, it became an obsession. While grocery shopping, folding laundry, even watching TV with Mike, her mind drifted to Harry. I want to prove it. It’s not sexual… okay, maybe a little. He’s attractive, that Christmas party where he wore that fitted jumper… but he’s just Harry. This is about skill, knocking that cocky grin off his face. But reality hit: Mike would kill me. It’s cheating. Wrong.
Sunday night, Mike was glued to his console, yelling into his headset during an online raid. Charlotte sighed, drawing a bath, but as the water ran, she heard him start another game. Plenty of time. In the bedroom, she rummaged through her nightstand drawer, pulling out her small bullet vibrator and a realistic dildo, flesh-toned, veiny, and about six inches. Just a quick play to unwind.
She lay back on the bed, hiking up her nightgown, rubbing the dildo along herself until wetness slicked it. Sliding it in slowly, she thrust gently, the bullet buzzing against her clit. Her mind wandered unbidden to Harry. What would his cock feel like? Thick, I bet, from that rugby build. Sucking him, making him groan…She pulled the dildo out, bringing it to her lips, sucking it deep while the bullet hummed. Yes, like this. Harry in my mouth, eyes rolling back… She got closer, hips bucking, imagining his hands in her hair. Orgasm crashed over her, hard and shuddering.
A creak on the floorboard. Mike stood in the doorway, eyes wide, a grin spreading. “Is this what you do when I’m gaming?”
Charlotte yanked the dildo from her mouth, covering herself with the sheet, mortified. Oh god, did he see? Hear?
Mike laughed, stepping closer. “Hey, don’t stop on my account. It’s plastic, enjoy yourself.”
“It’s latex, I think,” she mumbled, face burning.
“You could ride the chair leg with a condom on it for all I care. I’m not stopping you.” He shrugged, casual as ever.
Her mind raced. Anything? With a condom? He can’t mean… other guys. But… Harry. Aloud, she tested: “So, anything? As long as it’s got a condom, you really don’t mind?”
Mike nodded, pulling out his hardening cock. “Yeah, anything. But if you wanna suck something, suck this.”
She knelt before him, heart pounding. Now I have permission? Sort of? Taking him in her mouth, she bobbed slowly, tongue swirling around the head. Mike groaned, hands gentle in her hair. But in her mind, this is Harry. Thick, unyielding. I’d make him cum, prove it. She sucked deeper, imagining Harry’s broad frame, his glasses fogging. Mike’s breath quickened, and she hollowed her cheeks, flicking her tongue under the ridge. Harry would hold out longer, but I’d win. Mike thrust gently, praising her, “Fuck, Char, so good,” but she pictured Harry’s voice, deeper, rougher. When Mike came down her throat, hot and salty, she swallowed, thinking: See? I can do it. And now… permission.
Monday morning, excitement bubbled as she waited for Harry’s car. How do I say it? ‘Hey, Mike said I can suck anything with a condom? No, that’s insane. But if the chance comes…
Harry pulled up, honking lightly. Small talk flowed, weekend recaps, work gripes, but she steered back. “So, about that BJ thing…”
He chuckled. “Still on that? Let it go.”
At lunch, she fibbed: “Sooo, I talked to a friend, her boyfriend was like you, he couldn’t cum from BJs. Now he’s obsessed after she figured it out.”
Harry raised an eyebrow. “You’re really stuck on this. It’s like you want to prove you can make me cum.”
He sees through me. She smiled coyly. “Well, maybe I do.”
His cheeky grin emerged. “I told you, not a bet you’d win. But say we did… what are we betting?”
Nerves fluttered. “If we were and I’m not saying we are, you’d need to wear a condom. If I win, I prove it.”
“And when I don’t cum? What do I get?”
“Whatever you want,” she blurted, confidence masking her jitters.
Harry leaned in, testing. “Okay. When you give up, I fuck you, make you cum, then cum myself, in the condom, per your rule.”
Holy shit, is this real? “Deal.” They shook hands, electricity sparking.
The afternoon blurred into jokes, Harry assuming it was just banter. On the drive home, he asked, “So, when’s this happening?”
“Not tonight,” she said, pulse racing. “We finish early Friday. Maybe then?”
He laughed. “Sure, whatever.”
But for Charlotte, it was real. She’d planned it, Friday after work, park in that secluded wooded spot near her home, hidden by trees and away from prying eyes. In his car. Quick, proving her point, done.
The week dragged, filled with teasing jabs. “Backing out yet?” he’d ask. “Nope,” she’d retort, her mind replaying scenarios at night, fingers between her legs.
Friday dawned crisp. Charlotte dressed carefully, professional skirt and blouse, but underneath, lacy black panties and bra that made her feel sexy, confident. Just in case. Not that he’ll see them. Stomach churning with nerves and anticipation, she waited.
Harry picked her up, joking immediately. “Not too late to chicken out.”
“No way. Today’s the day.” As they drove, she pointed out the spot. “Park there later.”
His eyes widened slightly. She’s serious?
Work was a blur, short lunch on neutral topics, Harry relaxing, thinking the joke died. They wrapped early, and he waited in the car. Charlotte slid in, butterflies rioting, but arousal building too.
“Remember where to park?” she asked as they drove.
“Yeah,” he said, voice tighter. Still doubting.
They arrived and Harry reversed into the spot, engine off, belts unbuckled. He turned to her. “You know you don’t have to do this, right?”
“Chicken?” she teased. God, I’m wet already. This is crazy.
“Why? ‘Cause I’ll lose?”
She paused, serious. “Rules: No kissing. This is just a bet, not an affair. Condom mandatory. Don’t make our friendship weird.”
“Agreed. Even when you give up and I’m fucking you on the backseat?”
“You wish. Now get your cock out.” She said in a more forceful tone than she expected.
Harry, stunned but aroused, fished a condom from the glovebox. He unzipped, pulling out his semi hard cock. Thick, veined, about seven inches, uncut. He stroked it to firmness, rolling on the condom. Charlotte stared, saliva pooling slightly. Now it’s covered… permission…well kinda.
She grasped it, tugging gently, feeling it harden fully in her hand. Positioning awkwardly in the front seat, she leaned down. Here goes.
Her lips parted, taking the latex sheathed head into her mouth. The taste was rubbery, but she focused on technique, swirling her tongue around the tip, sucking lightly. Harry groaned, hand hovering near her hair. Fuck, she’s actually doing it. Feels good… but I won’t cum.
She bobbed deeper, hand stroking the base, cheeks hollowing. Up and down, varying speeds, slow teases, then faster and harder suction. Her free hand cupped his balls through his boxers, massaging gently. Harry’s breath hitched; he shifted, groaning deeper. Getting close? His groans… yes!
Ten minutes in, no release. Frustrated, she upped it, deepthroating as much as the angle allowed, gagging slightly for effect, humming vibrations. Come on, Harry. Cum for me. She pulled her blouse open, freeing her full breasts from the lacy bra, nipples hard. Pinching one, she hoped the visual pushed him. Harry stared, groaning louder, hips bucking subtly. God, her tits… so soft. But still… not gonna happen.
Fifteen minutes. Jaw aching, she sat up, defeated but hornier than ever. “Fine. You win.”
Harry laughed breathlessly. “Told you. But you don’t have to”
“I’m so worked up,” she admitted, climbing to the backseat. “I kinda want to get fucked now.”
He joined her, the car rocking slightly. She straddled him, skirt hiked, underwear aside. His hands roamed, squeezing her ass through the fabric, then under, kneading the soft flesh. So plump, perfect. She lowered onto his condom clad cock, gasping as it stretched her, thick and filling. Fuck, that’s bigger than Mike. Feels amazing.
She rode slowly at first, grinding her clit against his base. Harry’s hands cupped her breasts, thumbs circling nipples, pinching lightly. No kissing, but this… God. Inner thoughts raced. He’s so strong. Squeeze harder… yes. She bounced faster, the car windows fogging, moans echoing. His hips thrust up, meeting her, hands gripping her hips, then ass spreading, squeezing. Gonna make her cum first. Win properly.
Pressure built, she clenched around him, bullet-like intensity from her earlier fantasies fueling it. “Harry… oh God…” Orgasm hit, waves crashing, her walls pulsing.
He groaned, thrusting harder. “Gonna cum…”
Now! She rode through her aftershocks, feeling him swell. Just as his face contorted, eyes squeezing shut, mouth open, she lifted off, yanking the condom free. Diving down, she took him bare in her mouth, sucking hard. Hot spurts filled her throat; she swallowed greedily, tongue milking every drop, sucking him clean.
Pulling back, she grinned. “Told you I could.”
Harry, panting, laughed. “Technically, you didn’t, from the BJ alone. We need a rematch.”
As she dressed, adjusting her bra, she smiled. “Next Wednesday morning?” What am I doing? But… yes.
After the laughter subsided, the car filled with a comfortable, if slightly awkward, silence. Harry adjusted his trousers, zipping up with a satisfied sigh, while Charlotte smoothed her skirt down over her thighs, her skin still flushed and tingling from the intensity of it all. The condom wrapper crinkled under her foot as she shifted, a small reminder of the “rules” she’d set and bent. God, what just happened? That was… incredible. But it’s over now. Back to normal.
She glanced at Harry, who was starting the engine, his broad shoulders relaxed, glasses slightly askew from their backseat tumble.
“You okay?” he asked, pulling out of the secluded spot, the tires crunching over gravel as they rejoined the quiet suburban road. The sun was dipping low, casting a golden hue through the windows, and the air smelled faintly of sweat and latex.
“Yeah,” she replied, with a casual smile. “Just… processing. That was fun, though. For a bet.”
Harry chuckled, his deep voice rumbling. “Fun’s an understatement. And hey, rematch Wednesday? No backing out.”
Do I want that? Hell yes. But Mike… no, he gave permission, sort of. Condom rule followed, mostly. “Deal,” she said, her pulse quickening at the thought.
The drive to her house was short, only a few minutes, but it felt longer in the afterglow. They chatted lightly about weekend plans, Harry mentioning a rugby match he was watching with mates. Charlotte fabricating something about errands, to keep things from getting too heavy. As he pulled into her driveway, the familiar two story house with its neatly trimmed lawn coming into view, he turned to her. “See you Monday? Bright and early.”
“Monday,” she echoed, grabbing her bag. Leaning over impulsively, she gave him a quick peck on the cheek, platonic and friendly, before hopping out. Don’t make it weird, Char. It’s just Harry. She waved as he drove off, watching his car disappear around the corner, her body still humming with residual arousal.
Pushing open the front door, the cool air of the house greeted her, carrying the faint scent of takeout from earlier in the week. Mike’s voice echoed from the living room, shouts of “Flank left! Cover me!” interspersed with controller clicks. He was deep in his game, headset on, screen glowing with virtual explosions. Charlotte paused in the doorway, her heart still racing a bit. Should I say something? ‘Hey, hun, just got fucked by my work husband in his car. But it was a bet!’ No, idiot. He wouldn’t even hear me right now.
“Hey, I’m home,” she called softly, kicking off her shoes.
Mike glanced up briefly, eyes not leaving the screen for more than a second. “Hey, babe. Good day?” His fingers flew over the buttons, immersed in whatever raid or battle he was dominating.
“Yeah, fine. Short one.” She waited a beat, but he was already back in it, muttering into his mic about strategy. Typical. Not that I mind tonight. Don’t need questions. Feeling a mix of relief and a twinge of loneliness, she headed upstairs, her thighs sticky with the evidence of her afternoon adventure.
In the bathroom, she stripped off her clothes, the lacy underwear she’d chosen that morning now damp and rumpled. Turning on the shower, she let the water heat up, steam filling the room as she stepped under the spray. The hot cascade hit her skin, soothing the slight soreness between her legs, washing away the scent of Harry. His musky, masculine scent mixed with her own arousal. God, that cock… so thick, filling me up. And the way he squeezed my ass, like he couldn’t get enough. Her hand trailed down her body instinctively, fingers grazing her nipples, still sensitive from his touch.
Leaning against the tiled wall, water pounding on her back, she let her mind replay it all. The bet, the blowjob that almost worked, the shift to the backseat where she’d climbed on top, riding him with abandon. It wasn’t cheating. Mike said anything with a condom. And it was just to prove a point… mostly. But as her fingers slipped between her folds, finding her clit swollen and eager, she knew it was more. Fuck, it felt so good. Harry’s groans, his hands on my boobs, pinching just right. But was he better than Mike? Wait, no, don’t compare. But damn, that orgasm… and making him cum in my mouth at the end. I won, sort of.
She circled her clit faster, the water mingling with her renewed wetness, breath coming in short gasps. Imagine if we do it again on Wednesday. No car this time? His place? No, too risky. But God, I want to feel him inside me again. The thought pushed her over, her body shuddering as another climax rippled through her, knees weakening. She bit her lip to stifle a moan, waves of pleasure crashing until she slumped against the wall, spent.
Not cheating, she told herself again, turning off the water and wrapping in a towel. Just a bet. A really, really good one. But as she dried off, a small smile crept onto her face, anticipation already building for next week.
