Jenny's First Time
by Max Swan
Copyright© 2026 by Max Swan
Erotica Sex Story: 18yo Jenny has a disastrous date with a boy from school and calls her best friend's dad to pick her up from a seedy motel, since she can think of no one else who could help her discreetly.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft Consensual Romantic Heterosexual Fiction First ENF AI Generated .
My finger hovered over the screen, heart pounding in my chest like a drum I couldn’t silence. The motel’s flickering neon sign buzzed outside the thin window, casting erratic shadows across the stained carpet.
Will York had left me here, high and dry, after promising the night of my life, my first time, no less. Now, alone in this dump with its musty smell of old smoke and regret, I had no ride home, no one to call but him. Mr. Harrison. Rob. The thought of dialing his number sent a flush up my neck, mixing shame with that secret thrill I’d buried deep.
He was Susan’s dad, twice my age, and way out of my league. But he’d slipped me his card months ago at the community center, saying, “Call anytime you need something, Jenny.”
This favor? It felt dirtier than that. I tapped the call button before I could chicken out. The line rang twice, three times, and then his voice, deep, smooth, like aged whiskey, filled my ear.
“Hello?”
“Hi, Mr. Harrison. It’s Jenny Macklin.” My voice came out smaller than I wanted, shaky.
“Jenny? Everything alright? Susan’s not with you, is she?”
“No, I know she’s at her mom’s. Um, remember you said to call if I needed a ride? I’m ... kind of stuck. At a motel off Route 12.” I didn’t mention Will or the virginity fiasco. Not yet.
There was a pause, then a low chuckle that made my stomach flip. “Stuck, huh? Give me the address. I’ll be there in twenty.”
I texted the details and paced the room, my sneakers sticking slightly to the floor. Every creak of the building made me jump, imagining what Mr. Harrison would think when he saw me like this, hair messy from Will’s clumsy attempts, skirt rumpled, eyes probably red from holding back tears. But underneath the embarrassment, a forbidden spark ignited.
I’d caught him watching me at the center, his brown eyes lingering on my legs when I bent to pick up supplies, that Cheshire smile pulling at his lips. He made me feel seen, desired, in a way no boy my age ever had.
Headlights swept across the parking lot exactly nineteen minutes later. A sleek black Audi purred to a stop, its engine humming with quiet power. The driver’s door opened, and there he was, Mr. Harrison stepping out, tall and broad-shouldered in a fitted button-down that hugged his chest, sleeves rolled up to show forearms corded with muscle from his gym routine.
At fifty, he moved with the easy confidence of a man who knew exactly what he wanted. His dark hair, streaked with silver, caught the streetlight, and that perpetual stubble shadowed his strong jaw. He looked every bit the silver fox, distinguished and dangerously attractive.
I pushed open the motel door, the cool night air hitting my skin like a slap. Humiliation burned my cheeks as I approached, arms crossed over my chest. “Thanks for coming, Mr. Harrison. I didn’t know who else to call.”
“Rob,” he corrected gently, his voice wrapping around the name like an invitation. His eyes met mine, warm chocolate depths crinkling at the corners with that smile. Intense, unflinching eye contact that pinned me in place, making my pulse race. “And it’s no trouble, Jenny. You look like you could use a friend right now.”
I slid into the passenger seat, the leather cool against my thighs, scented with his cologne, something woody and masculine that filled my lungs. The door clicked shut, sealing us in this intimate space. As he pulled out of the lot, his hand brushed mine on the gear shift, a fleeting touch that sent electricity zipping up my arm.
“So, what happened? Boy trouble?” Rob asked conversationally.
My throat tightened. How could I explain? “Yeah. Will ... He bailed. Left me here after ... Well, it was supposed to be special, but it wasn’t.” The words tumbled out, laced with the ache of disappointment and that deeper, unspoken longing for someone who knew what they were doing.
He glanced over, his gaze dropping briefly to my lips before flicking back to the road. “Special, huh? Sounds like he didn’t deserve you.” There was an edge to his tone, protective, almost possessive. His fingers tightened on the wheel, knuckles whitening. “You’re too young to waste on idiots like that.”
Heat pooled low in my belly at his words, the way he said them, as if he saw through my shy exterior to the girl craving his approval. I shifted in the seat, my skirt riding up slightly, exposing more thigh than I meant to. Did he notice? His eyes darted down again, lingering this time, and I swear his jaw clenched.
“I ... I thought maybe tonight would be it, you know? My first time.” The confession slipped out, bold and vulnerable, hanging between us like smoke.
The car slowed at a red light, and he turned fully toward me, his presence filling the space, commanding, unyielding. “First time,’ he repeated, voice dropping an octave, rougher now. His hand reached over, resting on my knee, thumb tracing a slow circle that made my breath hitch. “That’s not something to rush, Jenny. It should be with someone who knows how to take care of you. Make you feel ... everything.”
My heart hammered, desire twisting with the taboo thrill of it all. Rob was Susan’s father, old enough to be mine, but in that moment, his touch felt like permission, like he wanted this as much as I did. I didn’t pull away; instead, I leaned into it, my skin tingling under his palm.
“Like you?” The words escaped in a whisper, flirtatious and daring, testing the line we’d danced around for months.
His smile turned wicked, eyes darkening with intent. “Careful what you ask for, sweetheart.”
His hand slid higher, just an inch, possessive and teasing, hinting at the power he held, the way he could unravel me with a single command. The light turned green, but neither of us moved, the air thick with unspoken promises, my body aching for whatever came next.
He finally eased the car forward as the light turned green, the engine’s low rumble vibrating through the seat and into my core. My skin still burned where his thumb had circled my knee, that simple touch igniting a fire I couldn’t ignore.
Rob’s eyes flicked back to the road, but I felt his gaze pulling toward me every few seconds, heavy and assessing, like he was mapping out every inch of my body in the dim glow of the dashboard lights. The tension hung between us, thick as fog, making the air feel too small for just the two of us.
I shifted in my seat, the leather creaking softly under me, my floral dress riding up a bit more from the way I’d angled toward him. The smoky makeup around my eyes probably smudged from the night’s chaos, but I caught him stealing glances at the low neckline of my top, where the lace of my lucky bra peeked out just enough to tease.
My coppery hair had mostly escaped its messy bun, strands brushing my shoulders, and I wondered if I looked as wrecked as I felt, embarrassed, yes, but alive with this forbidden pull toward him.
“Rob,” I said softly, testing the name again, letting it roll off my tongue like a secret. “About going home ... Could I maybe crash at your place tonight? I told my mom I was sleeping over with Susan, so it’s basically the truth. I can take her bed or the couch, no big deal.”
He let out a low, bemused laugh, his hand raking through that thick, silver-streaked hair. The sound sent a shiver down my spine, warm and rough, like he was already imagining more than just a guest room.
“Yeah, that works. Susan’s bed has fresh sheets. No trouble at all.”
The first stretch of the drive passed in charged silence, the city lights blurring past the windows. I could feel his eyes on me, making my cheeks heat, my thighs press together instinctively. He broke it first, his voice steady but laced with something deeper.
“I meant what I said. You don’t have to explain anything. But if you want to talk, I’m here. No judgment.”
I tucked a loose strand behind my ear, my green eyes meeting his for a beat before darting away. Honesty felt risky, but with him, it spilled out anyway. “Plans just ... fell apart. Bruised ego, still a virgin, nothing fatal. I’ll get over it.”
We hit another red light, and he turned to me fully, his chocolate eyes locking on mine with that intense stare that always made me feel exposed.
“You were going to lose it tonight?” Rob asked.
I nodded, biting my lip.
“Do I need to go back and kick that kid’s butt?”
The protectiveness in his tone wrapped around me, stirring that ache low in my belly.
“No, nothing like that,” I assured him, offering a shy smile as the light changed and we moved again. “He came before he could, err, put it inside me. He got mad, said it was my fault, then he left. Will wasn’t my boyfriend or anything. We were just casual. I was curious about sex, you know? Intellectually. And he seemed game. I guess he couldn’t handle the pressure or something.”
Rob shifted beside me, his grip tightening on the wheel, a flicker of something, apprehension? Desire, crossing his face.
“Sorry, was that too much information?” I asked.
“No,” he murmured, voice a touch huskier. “I like the honesty, Jenny. Appreciate it.”
“I couldn’t stay in that motel alone,” I went on, my voice gaining a little boldness. “And explaining to my mom? No way. So, you’re my knight in shining armor tonight.”
He paused, processing, his jaw working like he was wrestling with a thought. Emboldened by the way his eyes kept drifting to my cleavage, I pushed further.
“I’ve never been that into guys my age anyway. Maybe I should wait for ... a real man.”
He shook his head sharply, like shaking off temptation, but his smirk deepened, that Cheshire curve promising trouble. The road curved toward his neighborhood, the houses growing larger, more secluded. His eyes stayed on me longer now, even as he drove smoothly, the Audi handling the turns with effortless control. The tension coiled tighter, my pulse thumping in my ears, every glance from him feeling like a caress.
“That so?” he said finally, his tone low and teasing, laced with the flirtation we’d skirted for months. “Older men, huh? What makes you think they’d know what to do with a girl like you?”
My breath caught, heat flooding my face, and lower. “I don’t know. Experience, maybe. Someone who takes charge.” The words hung there, vulnerable and inviting, my body humming with the taboo thrill of admitting it to him, Susan’s dad, the man I’d fantasized about in quiet moments.
His hand left the gear shift, sliding over to rest on my thigh, just above the hem of my flared skirt. His palm was warm, callused from whatever workouts kept him so fit, and he stroked upward slowly, possessively, fingers tracing the edge of the fabric. The touch sent sparks racing through me, my skin prickling, a soft gasp escaping my lips as his thumb brushed the sensitive inner curve.
“Rob...” I whispered, not pulling away, instead, leaning into it, my body betraying how much I craved his control, the way he could make me feel small and cherished all at once.
My core tightened, wetness gathering between my legs, the emotional pull of his attention mixing with the raw want building inside me. He didn’t stop, his hand inching higher, claiming territory under the skirt with a confidence that made my head spin.
“Curious about sex, you said.” His voice rumbled, eyes dark with intent as he navigated the final turns. “With a man who knows how to handle that curiosity?”
I nodded, breathless, my hand covering his lightly, not to stop but to feel more. The forbidden edge sharpened everything—the age between us, the power in his touch, the romance blooming in stolen glances. My heart raced with equal parts fear and longing, emotions swirling as his fingers pressed firmer, teasing the line of my panties.
The Audi turned into his driveway, the garage door humming open ahead. He killed the engine, the sudden quiet amplifying our breaths. Leaning close, his stubble grazing my ear, he murmured, “Tonight, you’re mine, Jenny. No more waiting.”
His words hit like a promise, my body trembling with anticipation, the night stretching open with possibilities I both feared and yearned for. I wanted this, craved the way he made me feel seen, desired, but the taboo weight of it all pressed down, Susan’s face flashing in my mind like a warning.
He reached out, his hand settling on my knee in what should have been a reassuring pat. But there was nothing fatherly about the way his fingers lingered, warm and deliberate, sliding up just an inch before he pulled back. They grazed the bare skin of my inner thigh, leaving a trail of tingling fire in their wake. My flesh prickled, a soft ache blooming between my legs as I fought the urge to press closer.
“So,” he said, switching gears with a casual ease that snapped the tension like a taut wire, though his eyes still smoldered, “How are college applications going?”
I blinked, caught off guard, but played along, my voice dipping huskier than intended. “They’re ... coming along. Stressful, but exciting.”
We kept up the small talk for the rest of the short walk from the garage into the house, but I couldn’t shake the heat his touch had ignited. Testing him, I let my words carry a subtle edge, crossing my legs as we slipped off our shoes in the entryway, the hem of my dress hiking higher to reveal more of my pale, supple thighs. My fingers worked the tie from my bun, copper strands tumbling free across my shoulders. I combed through them slowly, ‘accidentally’ brushing the swell of my breasts, feeling his gaze snag on the motion.
As the Audi had pulled into the driveway earlier, I’d stolen a glance at his lap, a distinct bulge straining against his slacks. He was affected, sneaking peeks just like I was stealing them now. The forbidden spark between us crackled, age and authority twisting it into something intoxicating.
Once inside, Rob gestured toward the kitchen. “Drink? You look like you could use one after tonight.”
He headed for the liquor cabinet, pulling out a bottle of amber whiskey that caught the light. His back to me, I leaned against the counter, eyes tracing the broad lines of his shoulders, the way his shirt hugged his fit frame. Fifty and built like that, confident, commanding, it made my stomach flip with shy curiosity.
“Are you drinking tonight, Jenny?” My name on his lips sounded sinful, low, and intimate. “That’s not a trick question, by the way. I know you kids drink.”
“Just cola for me, please,” I said.
I watched him pour, his movements precise, then crossed to me and handed over the glass. He leaned in close, his nose nearly brushing mine, his woody, masculine cologne mixing with the faint trace of the night’s rain. The cool water shocked against my flushed skin, but it did nothing to douse the warmth pooling low in my belly.
He paced back to pour his own glass, then returned, leaning an arm on the counter behind me, caging us in that intimate space. He took a swig, the liquid burning down his throat, and I imagined the heat of it mirroring the one building inside me. His chocolate eyes locked on mine, warm but intense, creasing at the corners with that distinguished smile.
“Listen,” he said, voice dropping to a rumble that vibrated through me, “I think I know what you want tonight, Jenny. But you’re the only one who knows for sure. So maybe I’ll take the lead, but you will always be the one in charge. If anything hurts or makes you uncomfortable, I will stop as soon as you ask me to.”
My heart pounded, a wild drumbeat echoing the emotional storm inside, fear of the unknown, longing for his experience to guide me, the taboo thrill of crossing this line with Susan’s dad. His face drew closer, breath mingling with mine. “Is this really happening?” I whispered, half-scared it was all a dream, or worse, a cruel joke.
“Only if you want it to.” His lips brushed mine, feather-light, electric sparks dancing where we connected. It wasn’t a full kiss, but it stole my breath, my body leaning in instinctively. “I don’t want to be the perverted old man taking advantage of a beautiful young girl.”
The words hung, laced with his flirtatious charm, but I saw the power dynamic there, him offering control while holding the reins. Emboldened, feeling bolder in his gaze, I met his eyes with a shy defiance. “Well, maybe I’m the horny young girl taking advantage of a sexy, experienced man.”
That did it. Rob pulled me into a kiss, deep and passionate, like he’d been starving for it. His lips claimed mine with expert precision, parting them to let his tongue slip inside, exploring with a hunger that made my knees weak.
I tasted the whiskey on him, sharp, smoky, mingling with the faint salt of his skin. His stubble rasped against my sensitive cheeks, a rough contrast to the tender way he stroked the nape of my neck with one strong hand, the other pressing firm at the small of my back, drawing me flush against him.
I melted into it, inexperienced but eager, my tongue tentatively meeting his in a dance that sent heat surging through me. Feeling a spark of daring, I nipped his lower lip between my teeth, tugging just enough to tease, not to hurt. A low moan rumbled from his throat, vibrating against my mouth, his body tensing with restrained power.
He deepened the kiss then, tongue delving with urgent hunger, claiming every corner of my mouth as if marking me as his. His free hand roamed boldly, sliding under the hem of my dress, fingers gripping the curve of my ass with possessive strength. The squeeze sent a jolt straight to my core, my gasp muffled against his lips as I arched into him, craving the firm control he wielded so effortlessly.
I melted further, body pliant under his touch, the emotional intimacy blending with the building ache between my thighs. His fingers kneaded my flesh, pulling me tighter, and I felt the hard line of his arousal press against my belly, a promise of what was to come. He broke the kiss just enough to trail his lips down my neck, nipping softly at the pulse point, his breath hot and ragged.
With a swift motion, Rob lifted me onto the counter, my dress bunching up around my hips as he stepped between my parted legs. He pressed in hard, our bodies flush, the friction of his clothed erection against my damp panties drawing a whimper from me. His mouth claimed mine again, the kiss exploding with pent-up tension, hands everywhere, gripping, caressing, igniting.
The kitchen faded, the world narrowing to his commanding presence, the way he made me feel desired and safe in his power. But as his fingers teased higher, brushing the edge of my panties, a fresh wave of nervous excitement washed over me. What came next would change everything, and I wasn’t sure if I was ready, even as I pulled him closer.
His fingers teased higher, brushing the edge of my panties, and I shivered, the anticipation coiling tight in my core. But then Rob pulled back slightly, his breath ragged, eyes locking onto mine with that intense, warm gaze that made my heart stutter. The kitchen light cast shadows across his strong jawline, highlighting the silver in his stubble, and I felt the full weight of our age gap, the forbidden pull of his experience against my innocence, making every moment feel electric and wrong in the best way.
“We need to go over some details,” he said, his voice low and steady, like he was anchoring us both in the reality of this.
His hands stayed on my hips, thumbs tracing slow circles that sent sparks up my spine. I nodded, still perched on the counter, my legs parted around him, the cool granite a stark contrast to the heat building between us.
“I’ve only been with two other women since the divorce,” he continued, his chocolate eyes never leaving mine, holding me in that commanding yet tender way that made me feel safe and desired all at once. “I’ve been tested, and I’m completely clean. I also had a vasectomy a few years back. We do not need to use a condom. But since this is your first time, I completely understand if you want to.”
The words washed over me, easing a knot of worry I hadn’t even voiced—no barriers, just him, raw and honest. The taboo thrill intensified; this was Susan’s dad, offering himself without restraint, his power dynamic wrapping around me like a promise. I smiled, biting my lower lip as a flush crept up my neck.
“It will be nice to really feel you in me. The whole time,” I said.
He blew out a breath, the sound rough with relief and hunger, and gripped my left thigh, massaging slowly upward, his palm warm and possessive against my skin. Emboldened by his vulnerability, I raised my trembling hands to his collar, fingers fumbling with the buttons of his shirt.
One by one, they gave way, revealing the tanned planes of his chest, dusted with dark hair that trailed down to his belt. My palms flattened against his skin, exploring the firm muscles honed from years of discipline, feeling the steady thump of his heart under my touch. God, he was solid, commanding, everything I’d fantasized about in stolen moments alone.
“God, you’re beautiful,” he murmured, his voice a gravelly whisper that vibrated through me. His hand slid higher up my dress, working its way to my panties, the fabric already hot and moist from the ache he’d ignited.
The flirtation in his tone, laced with that authoritative edge, made my pulse race, the emotional pull of his attention drawing me deeper into this forbidden dance.
“You’re so sexy, Rob,” I breathed, my shyness cracking under the weight of my desire. “I’ve fantasized about this so many times.”
His shirt fell open fully now, and he shrugged it off his shoulders, the motion flexing his biceps in a way that made my mouth go dry. My hands roamed his bronze chest, tracing the ridges of his abs, my mind flooding with images of him pressing this strapping body into mine, his strength overwhelming my young, untouched flesh. The power he held over me felt intoxicating, not scary, romantic in its intensity, taboo in its reality.
“You’ve fantasized about me?” he asked, his eyes darkening with a mix of surprise and heat. I nodded, heat flooding my cheeks. His fingers fondled the lacy band of my panties, tugging lightly, sending a jolt straight to my core. “Do you touch yourself thinking about me?”
Another nod, my breath hitching as his touch grew bolder. The vulnerability of admitting it aloud twisted something emotional inside me, years of shy longing for his approval, his flirtatious glances at the community center, now blooming into this raw intimacy.
His fingers slipped under the fabric, tracing along my slippery lips, and I gasped softly, my body arching toward him. “You finger yourself, pretending it’s my hand inside you?” he pressed, his voice dropping lower, commanding answers from me like he owned every secret.
Nod.
The word barely formed in my mind before he thrust his index and middle fingers into my velvety pussy lips, stretching me with a deliberate slowness that made stars burst behind my eyelids. I tossed my head back, a sharp gasp escaping as he worked himself in and out of my pussy, the wet sounds mingling with my quickening breaths.
He pressed his lips against my exposed neck, sucking gently, then licking a hot trail up to my ear, nibbling the lobe while my hands ran down his arms, appreciating the lean power of his biceps and triceps. Each flex under my fingers reminded me of his age, his experience, guiding me with a tenderness that masked the urgent hunger beneath.
The sensation built, his fingers curling inside me, teasing that spot that made my thighs tremble. Emotions swirled: the romance of his care, the forbidden rush of surrendering to Susan’s father, the power he wielded so effortlessly, making me feel alive, wanted. My hips rocked instinctively, chasing the friction, a soft moan slipping free as he fingered me deeper, his thumb brushing my clit in lazy circles.
“What color?” he groaned against my skin, his free hand gripping my hip to steady me.
I started rocking my hips back and forth, lost in the rhythm he’d set. “Huh?”
“I wanna know what color your panties are, Jenny.” His words were dirty, laced with that flirtatious command, igniting something bold and hungry in me. The taboo edge sharpened, the man who’d always treated me like an equal now demanding details in this intimate, possessive way.
“Um, red. The lace is black,” I managed, my voice breathy, a shy smile tugging at my lips despite the heat.
His eyes flashed with raw desire, and he pulled back just enough to look at me, fingers still buried deep, pumping steadily. “I want them in my mouth.”
My jaw dropped, the dirty talk hitting like a spark to dry tinder. A fresh wave of arousal flooded me, mixing with the emotional high of Rob’s fixation on me, me, the shy girl he’d flirted with for years. I felt daring, influential in my vulnerability, the age gap, and the forbidden nature, only fueling the fire.
“Then take them,” I whispered, my hands sliding to his belt, heart pounding with anticipation of what he’d do next, the night stretching open with endless possibilities.
He stopped above my panties. I propped myself up on my elbows and pouted at him, wondering what game he was playing now. He smiled back at me, a fresh glint in his eyes.
“You’re blushing. I like making you blush, Jenny. You’re really fucking cute when you blush.”
His thumb massaged my clit, sending fresh waves of heat through me. The words hit me hard, that mix of tenderness and raw command making my chest tighten with emotion, the way he saw me, this older man drawing out my shyness while stoking the fire between us.
“Of course, you’re always cute. You’re cute when you smile ... when you cry ... and tonight I’m gonna find out just how cute you are when you cum.”
With that, he removed his digits from my shuddering cunt. We kissed again, panting as our two separate forms melted into one. I had used coconut scrub all over my body before going out that night, and now the taste was on Rob’s breath, mingling with the whiskey. Through our clothes, I could feel his cock against my pussy, stiffening as I squeezed my legs around him.
The hardness of him pressed right where I ached, the taboo thrill of his age and authority making my body respond with a desperate need. This was Susan’s father, his experience guiding me, and the forbidden pull made every touch feel like a secret we both craved.
“Let’s take this upstairs,” I hummed in his ear, my voice breathy with the emotional rush of finally voicing my desire.
He lifted me in his arms, my back arching so that my body fit perfectly against his. I strengthened the hold my thighs had around his midsection, and he carried me like that the entire trip upstairs, his strong arms flexing under me, a reminder of the power dynamic that had always simmered between us, him the confident silver fox, me the young girl seeking his approval.
When we got to the master bedroom, Rob placed me on his bed so that my legs hung over the edge. He loosened his belt and let his pants fall to the floor. He stepped out so my eyes could discover his entire perfect body, now only covered by cotton boxer-briefs. The outline of his erection strained against the fabric, thick and insistent, and I swallowed hard, my heart pounding with a mix of nerves and excitement.
The room smelled faintly of his cologne, woodsy and masculine, heightening the intimacy of this space, his sanctuary, now shared with me in this illicit way.
“You’re so sexy, Rob,” I purred, my shyness fading into bold flirtation as I took in his fit frame, the silver flecks in his hair catching the lamplight.
He lowered himself over my body, forcing me to lie back as he planted more whiskey kisses on my lips and toyed with the hem of my dress. His fingers once again found themselves on my panties, this time tracing me over the fabric, the pressure light but teasing, building that emotional tension of surrender. Slowly, he removed his hand from under the dress, and instead, he tugged at the hem again.
“This should come off.” I started to slip my thumb under the tank top strap on my right shoulder, but Rob brushed my hand away. “Please, allow me.”
He sighed happily and placed his hands on my shoulders. He put another kiss on my lips, more deeply than earlier, like he wanted to savor this one. His coconut-and-whiskey breath was intoxicating, drawing me deeper into the romance of his touch, the way he made me feel cherished even as the taboo-edged sharpened my arousal.
His fingers skimmed under my right strap, gently pulling it down until my arm slipped free, tickling my soft, naked skin with his light touch along the way. This sequence repeated itself on the other strap. The top of my dress was draped around my waist, exposing my lucky bra, red with black lace.
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