Virgin Whisperer: Leo’s Initiation

COMMENT TO READERS:

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All characters are 18 years or older and engage in activities described with full knowledge and consent. It is inspired by an amazing story DORMANT DESIRES by becca20S. I really enjoy her story as it feels very real to me and I enjoy imagining her introducing more young, virgin men into the beauty of sexual pleasure. If you have not checked her story, you really should.

So this is really an imperfect attempt at following into her footsteps, a tribute. I hope she sees it as appreciation, maybe even encouragement to continue explorations into Becca's world. Because to me she is way more than just another mature woman character in an erotic story. She's something like a Virgin Whisperer -- not chasing youth for validation, but drawn instinctively to that fragile place in a young man's eyes where fear meets desire. She doesn't just take virginity but rather she unlocks something. She does it slowly, intimately, with care and fire, and I think it is the best form of Reality/Therapy Erotica.

And of course, it would be the greatest honor if she considered any aspect of this story as potential inspiration to write her part in first person.

Hope you enjoy, at least part :-).

**************

Becca hadn't even finished reading the graduation invitation before the memories of that fateful night came flooding back. The dorm room. The boys. That feeling. God, that feeling. It was supposed to be a one-time, spontaneous escape from everything her life had become, but now, even a mention of a college campus stirred something deep inside her. Something primal. Something hungry.

She could still remember the smell of that dorm--cheap cologne, stale pizza, and sweat. The look on their faces when she walked in with the booze. The unfiltered desire in their eyes. That moment changed something in her and going to any college campus now didn't feel like a casual social visit. It felt like going back to the scene of a beautiful, irreversible crime. That night had awakened something that wouldn't go dormant again. Not ever.

As the memories came back, her fingers trembled, clutching the paper invitation from her old friend inviting her to her daughter's graduation. This university was a few hours away, and since she was invited to the post-ceremony party, she booked herself a room at a boutique hotel just off campus. She told herself it was practical--too long of a drive for a quick visit--but the truth sat hotter in her chest. She wanted the option to stay late. To wander. To watch. To give fate a chance at giving her another special moment.

She arrived early, checked into her hotel, and unpacked slowly, savoring the nerves dancing in her stomach. She caught her reflection in the mirror--jeans snug across her ass, a soft blouse clinging in all the right places--and remembered how that last visit had made her feel more alive than she had in years.

Graduation was beautiful, yes. Emotional even. She watched her friend's daughter walk across the stage, the proud mother beaming beside her. But Becca? Becca couldn't stop scanning the sea of young men in caps and gowns, wondering which of them still carried their virginity like a weight they didn't know how to let go of. The thought made her thighs clench beneath denim, the soft blouse now suddenly too warm against her skin.

She knew it was wrong, and she didn't care. She just wanted to be wanted--deeply, hopelessly, worshipfully wanted. And nothing in the world compared to the way those young, awkward eyes looked at her that night in the dorm.

So when the ceremony ended and everyone flooded out for photographs and family hugs, Becca slipped away toward the nearest coffee kiosk. Her heart was racing and she wasn't sure why. Maybe it was the smell of campus air. Or the way sunlight hit the boys' shoulders through their thin gowns. Or maybe it was just a restless itch beneath her skin -- the kind that had no name but came with heat.

She didn't know what she was looking for. Just that she needed a moment alone, a strong coffee, and maybe -- just maybe -- a reminder of why she'd come.

Her attention turned toward the shaded corner of the quad. It was a bit of a walk but she did not mind, the quiet espresso machine drawing her in. She leisurely started walking, unaware what would await her there.

****

"Alright, Big Country," Tom grinned, leaning back on the bench outside the student union. "You said you've had sex before. Time to prove it."

Will chimed in with a smirk, "Yeah, and none of that 'back home in a cornfield' fantasy stuff. Real women. Right here. Right now."

Leo, towering at six-four with a shaggy blond mop of hair and a faded flannel shirt, swallowed hard. His hands were tucked deep into his jeans, thumbs nervously flicking at his belt loops. His cheeks already had a pink hue -- partly sunburned, partly panic.

"What exactly y'all want me to do?" he drawled, glancing around.

Tom pointed. "See those two girls by the fountain? Try your best pickup line. The one you'd use on a real date."

Will sensing that Leo probably does not have one and may accept any suggestion, however ridiculous, laughed. "No -- use this one. 'I'm not a photographer, but I can definitely picture us naked together.' Say it. Mean it."

Leo's jaw dropped slightly. He did not want to search online in front of them so was initially relieved. But then he started to think about the true meaning of it. "Hell no, I cain't say that to them... they look like they'd call campus security if I even sneezed funny."

Tom slapped his shoulder. "C'mon, cowboy. You're tall, you're handsome -- it'll work. Unless... you're actually a virgin and can't pull it off."

That word hit Leo in the gut like a shovel. "I ain't no virgin," he muttered -- too fast to be convincing.

Silence followed, heavy and awkward. Leo shifted his weight, jaw tight, pretending not to see the smirk on Tom's face. His heart thudded in his ears -- part nerves, part stubborn pride. He wasn't about to let them call his bluff.

After a few minutes later, the discomfort got the better of him and Leo walked stiffly toward the two girls in yoga pants and oversized sunglasses, lounging on the edge of the fountain. His boots clunked louder than normal on the pavement. Tom and Will watched from behind a nearby planter, stifling laughs.

Leo (awkwardly): "Uhm, excuse me, ladies. I... I was just wonderin'... I ain't no photographer, but I reckon I could picture us... uh... naked together."

There was silence. One girl blinked. The other laughed. Not a kind laugh.

Girl #1: "Ew. What?"

Girl #2: "Seriously? Is this some TikTok dare?"

Leo, mortified: "N-no ma'am, I was just--"

Girl #1 (cutting him off): "Yeah, no thanks, cowboy. Try again when you're not in puberty." They walked off, giggling.

Will: "Woooow. Rougher than a hayride on potholes."

Tom: "He's blushing so hard you could roast marshmallows on his face."

Leo stormed back over, face beet red. "This was stupid. I told y'all I ain't good with words."

Tom (grinning): "You still owe us. Try again. Someone more your speed."

Will raised his brows and nodded toward a woman standing by the coffee kiosk, flipping through her phone. Becca. Tight jeans, a soft blouse, striking figure -- older than the average student by two decades and owning every second of it.

Will: "She's hot, and she's not gonna laugh in your face. Probably."

Leo: "You want me to say that line to her?"

Tom: "Exactly. And if you don't, we're telling everyone you sleep with your tractor." They were banking on a slap or some brutal shutdown from a grown woman -- either way, it'd be hilarious. Leo took a shaky breath and started walking.

At the Coffee Kiosk, Becca was just tapping on her screen when she noticed a very tall, very nervous-looking farm boy approaching her with the kind of tension you'd expect from someone walking toward a dentist chair.

Leo (stammering): "'Scuse me, ma'am. Uh... I--I ain't no photographer, but... I sure could picture us... uh... naked... t-together."

Becca blinked once, slowly. Then raised an eyebrow. She said dryly: "Well, that was bold. And deeply unconvincing."

Leo (laughing nervously): "I'm real sorry, ma'am. My friends dared me. I ain't good at this. Ain't used to talkin' to pretty women."

Becca smiled -- not cruelly, but with a certain amused control. She gave him a mischievous look: "Let me guess... You're a virgin, right?"

Leo froze. "What? N-no! I mean, I ain't--"

Becca (teasingly): "Sweetie, it's okay. The second you opened your mouth, I knew. That line didn't come from a place of swagger. It came from the bottom of a bucket of nerves."

Leo looked like he wanted to melt into his boots. "I shouldn't've said nuthin'... I'll go--"

Becca stepped closer, just a breath inside his space, and said softly: "But... you did picture it, didn't you?"

Leo, barely whispering, unable to control his instinctive reaction to her question: "...maybe."

Becca: "Me. You. Naked."

Leo's face went fire-red. His throat clicked. He didn't say a word, looking away from her form as he realized she noticed him secretly ogling her. He was not sure if he was more ashamed of his inability to converse with her or his reaction to her charms.

Becca leaned in just a touch more, her voice almost conspiratorial: "Don't worry, Leo. I won't tell your friends how you looked at me just now. Like I was the first woman you'd ever seen naked in your life."

Leo swallowed. Hard. "...I, uh, I gotta go check on somethin'..."

Becca (smiling with a wink): "You do that, sweetheart. And tell your friends I said thanks for the entertainment."

As Leo walked away, awkward and flustered, Becca looked down at her phone again, fighting a grin.

At the planter, Tom said: "She didn't slap him. That's a win.". And Will added: "Dude looked like he was about to faint. Think he got a number?"

Leo approached them, and honestly blurted out as his interaction with Becca was replaying in his head: "She said I looked like I ain't never seen a naked woman."

Tom: "Have you?" Leo didn't answer, regretting his comment. His friends burst out laughing.

*******

After Leo stormed off, cheeks flaming, Becca lingered at the coffee kiosk. Her coffee steamed untouched beside her phone, but her mind was elsewhere. That boy -- Leo -- had just made a mess of a line so clumsy it should've been forgettable. And yet, it wasn't. Not to her.

There'd been something in his eyes -- a kind of naked panic, laced with something sweeter: hunger. Not just desire, but confusion about it. It tugged at her in the most unexpected places. She didn't just see it; she felt it. Understood it. Like she was wired for this -- for men like him, unsure and burning beneath the surface. The feeling surged again, sharper this time, as if some half-buried instinct had kicked into high gear. Her inner Virgin Whisperer stirred, alert and ready.

She didn't chase virgins the way some women chased youth or validation. It wasn't a game, not exactly. It was instinct. A pull toward that uncertain look in their eyes--the tightrope between curiosity and fear, innocence and want. There was something sacred in that first stumble, that messy surrender of control. Becca didn't just see nervous boys; she saw potential. Soft clay, unshaped but aching to be molded. She could coax their secrets with a look, their hunger with a whisper. That's what made her the Virgin Whisperer--not some crude label, but a truth she carried in her bones. She didn't just take their virginity. She unraveled it. Slowly, deliberately, with care and fire.

When she finally got up to leave, she noticed the two cards on the pavement -- his student ID and driver's license, just barely peeking from under the edge of the kiosk wall. She picked them up and stared. The logical thing would be to turn them in at campus security. But the semester was over. It was winter graduation day, the very last, and most of the offices were shuttered or running skeleton crews. Everyone was racing out of town for the holidays. She slipped the cards into her purse.

Back in her hotel room, Becca tried to distract herself -- checking emails, laying out clothes for the graduation dinner she was meant to attend in an hour. But her eyes kept going back to the cards.

Leo Maddox. A student. A baby-faced, six-foot-something farm boy trying so hard not to look inexperienced. She searched the campus directory, even tried Facebook. Nothing helpful. No contact, no address.

And let's be honest -- even if he had her number, he wouldn't have used it. He was too proud. Too unsure of himself. Too embarrassed to risk another stumble. Which meant if she wanted to return the cards in person -- which she absolutely did -- she had to do it now.

She stood for a moment in front of the mirror, holding her dress up to her body. It was simple but flattering -- soft black, hugging her curves, showing just enough skin to feel dangerous without trying too hard. She told herself it was for the graduation dinner. That she should look presentable. Polished.

No one there would really notice. Still, she slipped into the dress anyway, fastened a thin gold clasp at her neck, and chose lingerie that made her feel powerful -- even if nobody else would ever see it. This is just to boost my ego, she told herself. Nothing more.

Her eyes flicked briefly toward the cards on the table. She ignored the impulse to reach for them. Instead, she grabbed her purse and headed for the door.

Halfway down the hotel hallway, she paused. "Damn it," she muttered. "I forgot them." The cards were just a minute away, sitting on the table in her room -- but she didn't turn back. Not because she couldn't but because deep down, some part of her didn't want to. Leaving them behind gave her an excuse. A reason to bring him with her. And she wasn't ready to let go of that just yet.

The campus had turned ghostly. Long shadows stretched across the quad. Suitcases had disappeared. Even the coffee kiosk was shuttered, chairs stacked. The world had moved on -- except for one figure pacing frantically between benches and trash cans: Leo.

She watched for a moment as he checked under benches, crouched to inspect a planter, then stood and rubbed the back of his neck in exasperation. She walked up behind him.

"Lose something, sweetheart?"

Leo turned sharply, startled. "You! I--I think I dropped my ID. I can't find it anywhere."

"You did," Becca said. "And I found it."

His eyes widened. "Thank God. Do you have it?"

"I did," she said, glancing at her watch. "But I'm in a bit of a rush. Graduation dinner. I left it back in my hotel room."

Leo's face fell. "Oh."

"If you want it now," she added quickly, "you'll need to come with me. We'll grab it fast, and you can be on your way."

Leo looked around the quiet quad. His phone was dead. He couldn't get into his dorm without the card. And he wasn't about to call Tom or Will -- they were probably halfway to the airport by now.

Sensing his hesitation -- and realizing she already knew more about him than he did about her -- she offered a soft smile. "You can call me Becca," she said, extending her hand. Leo stepped forward and took it, his large hand wrapping around hers with surprising gentleness -- like he was afraid he might break something delicate. That first touch sent a ripple through her, low and electric.

"Yes, ma'am," Leo replied, his voice quiet. She almost laughed, but held it in. So sweet. He couldn't even bring himself to say her name. The old-fashioned politeness of this nervous, virgin farm boy melted her -- and she decided to let it slide. For now.

Having no other choice and feeling more comfortable, he finally nodded, "Alright."

Becca turned and led the way, heels clicking on the empty sidewalk. "Let's make it quick then. I've got a party to get to."

They walked in silence for a minute, the winter evening air cool but not cold, and the mostly deserted campus amplifying every sound -- her heels, his boots, the faint rustle of wind in the magnolias.

Leo stayed half a step behind her, head slightly down, hands in his pockets.

Becca glanced sideways. "You're awfully quiet."

Leo shrugged. "I just... I didn't expect to see you again."

She smiled to herself. "Disappointed?"

"No! I mean--no, ma'am. I'm glad. Kinda. I just... I thought you were gonna think I was weird or stupid."

She slowed a little. "Because of the line?"

"Yeah. That. And everything else."

Becca turned slightly toward him as they walked. "You mean, because you're a virgin."

Leo winced like she'd struck a nerve. "I didn't say that."

"No, but you didn't deny it well either."

He exhaled sharply. "I kissed a girl once. Back home. Does that count?"

She chuckled. "That depends -- did she kiss back, or were you aiming for a dare?"

Leo didn't answer.

Becca softened, her tone dipping into something more curious. "Is it that bad? Where you're from?"

He hesitated. Then, with surprising honesty: "I come from a real conservative place. Sunday school, modesty rules, girls don't talk about sex, boys don't either unless they're drunk or lyin'."

She nodded slowly. "So... you never really got to ask questions. Or want things. Not out loud."

"No, ma'am."

Becca stopped walking for a beat, and he did too. She faced him, her expression softer than before. "You know," she said, "you could've delivered that line to anyone and gotten a laugh or an eye-roll. But the way you said it -- nervous, polite, like you were about to apologize for even thinking it -- it told me everything."

Leo looked down. "I know I sounded dumb."

"No," she said firmly. "You sounded honest. That's what caught me."

They resumed walking, now at a slower pace. Becca's thoughts drifted as they neared the edge of the hotel property. She had come here tonight restless, bored -- surrounded by graduates and families and too many young men who were, by all measures, attractive. Confident. Self-assured in the way that came from knowing they were already men.

But Leo... Leo was different. Closed off, awkward, yes -- but raw. He hadn't stepped fully into himself yet. He was still teetering on the edge -- unsure, unguarded. He hadn't built the armor yet. And something in her wanted to crack it open -- not to tease, not just to touch -- but to reshape it. To give him something better than whatever guilt-soaked awkwardness he'd been raised to expect. Something about that unpolished innocence stirred a hunger in her that confidence never could.

She fished her keycard from her purse as they reached the hotel entrance. "It's upstairs," she said lightly.

Leo just nodded, following her in silence.

As the elevator dinged and they stepped inside, she looked at him in the mirror. He was fidgeting with the seam of his sleeve, jaw tight.

When they reached her floor, she walked down the carpeted hallway, stopped at her door, and turned the key.

"I've got your ID and license right inside," she said over her shoulder.

Then, she opened the door and stepped inside -- not turning back, but leaving it open behind her. Just wide enough for him to follow. Leo hesitated in the hallway. The open door gaped like a dare.

Inside, Becca was already moving -- not urgently, but with the unhurried grace of a woman who knew who she was and was proud of it. She disappeared around the corner, out of sight, her voice floating back: "You coming in, Leo, or are you just going to stand there wondering if this is a trap?"

Leo swallowed, boots scuffing awkwardly against the carpet. He stepped inside like it was enemy territory. Becca reappeared a moment later, holding two plastic cards between her fingers -- his student ID and license -- and waved them like a blackjack dealer.

"I believe these belong to you," she said, eyes gleaming.