A Second Chance At First Love Pt 02

Prologue: Where We Left Off

Lisa and Andrew had rediscovered each other in the wake of their respective divorces. Long-lost high school sparks reignited into an intense, sometimes unorthodox passion. Their first night together was a revelation: Lisa introduced Andrew to a side of intimacy he'd never experienced--prostate play and a deliberate, controlled "ruined orgasm." The experience left him in awe, drained physically but burning with unquenched longing. The emotional connection between them only deepened the impact of this new, adventurous sexual territory.

By the end of that fateful first evening, Andrew found himself driving home with a heart pounding from excitement and nerves. The girl he once adored from afar had transformed into a confident, self-possessed woman. She was playful, open-minded, and ready to explore desires she'd hidden for years. In response, Andrew realized that his own boundaries--shaped by a lackluster marriage--were far more malleable than he'd ever imagined.

Now, a few weeks later, they stood on the threshold of an even more complex dynamic. Andrew was discovering that Lisa's desires went beyond a single experiment: She wanted control, a slow forging of trust, and a sense of authority over his release. And, strangely enough, he wanted to give her exactly that.

Chapter 1: A Temporary Lock and Key

Andrew stood in front of the bathroom mirror, turning this way and that, assessing the unfamiliar device around his most intimate area. The chastity cage was snug but not painful, made of lightweight materials that allowed him some comfort while restricting any hint of arousal. A small lock secured it in place--Lisa held the key.

He was still reeling from how quickly this arrangement had solidified. After the night of his first "ruined" experience, Lisa had hinted that she wanted to take their exploration further. It started innocently enough: playful jokes about controlling his pleasure, remarks about how he might learn discipline if he had to earn his release. But when she presented the chastity cage a week ago, Andrew hesitated--only for a moment--before agreeing.

He liked seeing Lisa confident and in charge. He also liked the idea of showing her he could be trusted. Perhaps deep down, he enjoyed the edgy rush of surrender. Still, the reality of being locked up sometimes sent a nervous thrill through his body.

Lately, he'd noticed Lisa's grin whenever she caught him casually flirting with someone--or even letting his gaze wander. Nothing serious, just typical social interactions that apparently warranted her mischievous brand of control. She'd narrow her eyes in playful warning, remind him who truly decided when and how he'd find relief.

"It's for your own good," she teased on more than one occasion. "And for mine. I like knowing you're craving me."

He couldn't argue with that. Every minute spent in the cage felt like a low-level ache of anticipation. Sure, he could function at work, do his chores, and meet friends without major discomfort. But any hint of sexual arousal quickly met the confines of plastic and steel. It served as a constant reminder of Lisa--the woman who owned his release.

Chapter 2: An Early Morning Lesson (Prostate Milking, Part 1)

They had been seeing each other steadily for these few weeks, but this morning was different. Lisa had invited Andrew over for breakfast, claiming she wanted to "check on a few things"--a coy reference to the cage. He arrived promptly, carrying a small bouquet of flowers and a sense of electric anticipation.

The house smelled of fresh coffee and something sweet, maybe muffins. Lisa, wearing a casual T-shirt and shorts, greeted him with a warm hug. Her eyes darted down to the slight bulge under his jeans, and she smirked.

"Missed me?" she asked, leading him by the hand into the kitchen.

"You know I did," Andrew replied, pressing a kiss to her temple. The tension in his body was real; he hadn't had an orgasm--a real orgasm--in over a week.

She poured coffee into two mugs and motioned for him to sit at the table. "Eat a little something. Then we'll head upstairs. I need to check you."

Andrew's pulse quickened. The subtext was clear: she wasn't just "checking" the device. She had plans.

They chatted over blueberry muffins and coffee, the conversation drifting between banter about their favorite new TV show and gentle flirtations about the night to come. But Lisa kept glancing at his crotch with that knowing smile, as though she could sense how pent-up he was.

Eventually, she set her mug down, stood, and extended a hand. "Let's go."

The Setup

In her bedroom, she closed the door and drew the curtains, dimming the morning light. Then she motioned for him to sit on the edge of the bed.

"Shirt off," she commanded softly.

Andrew complied. She took a moment to appreciate his bare torso, letting her hands rove lightly across his chest. Her touch was warm, tinged with a sense of ownership.

"Pants off, too."

He stood and slid out of his jeans. The chastity device was fully visible beneath his boxer briefs. Lisa nodded, a flicker of satisfaction in her eyes as she carefully removed his underwear.

Moments later, Andrew stood in front of her, the cage locked around him. His cheeks warmed with a mix of slight embarrassment and heady excitement. Lisa produced the small silver key from a drawer, twirled it between her fingers, then unlocked the device. The click of the lock echoed in the quiet room.

Relief momentarily washed over Andrew as she removed the ring and cage. He was freed--but only for a moment.

"Lie down," she instructed. "On your back first."

Preparations

Lisa slipped on a pair of black nitrile gloves. She took her time applying a generous amount of water-based lubricant to her gloved fingertips. Andrew watched each motion: the slow, deliberate way she coated her fingers, the poised determination in her posture. He could feel his heart racing, his length thickening rapidly now that it was no longer confined.

She smiled down at him, leaning in for a kiss that tasted of coffee and excitement.

"Try to relax," she whispered, echoing the words she'd once said during their first experiment.

Andrew swallowed hard, nodding. A sense of anticipation thrummed through him. He recalled the mixture of pleasure and frustration that milking had brought. Would it be the same this time? Or something more?

Positioning and the Mirror

Before proceeding, Lisa angled a full-length mirror that stood in the corner, making sure Andrew could see. "I want you to watch," she said. "Part of learning is seeing how your body responds."

She guided him to roll onto his side, then onto all fours, repositioning him until he was kneeling on the bed, his torso lowered slightly. The mirror captured his profile--his face, shoulders, the curve of his back, and his upturned rear. Lisa knelt behind him, leaning forward until her breath warmed the small of his back.

"You're okay with this, right?" she asked softly, sincerity slipping into her otherwise mischievous tone.

"Yes," Andrew managed. His throat felt tight with anticipation. "I trust you."

At that, she gently parted his cheeks and pressed a single lubricated finger against his entrance. The sudden contact made his entire body tense. He caught his own reflection in the mirror, noticing how his expression flickered between trepidation and want.

"Deep breaths," she reminded him.

He exhaled, letting the tension drain from his muscles as much as he could. Slowly, her finger began to slip inside. The initial intrusion felt cool because of the lube, but the warmth of her skin soon followed. He moaned softly, adjusting to the sensation.

The First Sensations

A rush of conflicting feelings flooded him: a hint of vulnerability at being in this position, deep arousal, and a wave of comfort from Lisa's assured touch. She twisted her finger gently, searching for that sensitive gland nestled within. When she found it--exerting a mild pressure that sent sparks up his spine--Andrew's mouth fell open.

"Oh, God," he gasped, eyes flicking to the mirror. He could see Lisa's shape behind him, her gloved hand partially obscured, but he felt everything.

She began a series of slow, deliberate strokes. Each pass of her finger nudged his prostate in the most tantalizing way. He could almost feel the warmth pooling in his pelvis, an ache that was equal parts pleasure and urgent need.

Time seemed to slow. All that existed was her finger's motion, the quiet hush of her breath, and the occasional whimper that slipped from his lips.

Building the Pressure

Her free hand rested on his hip, steadying him whenever he trembled. The caress of her finger was patient, methodical, and excruciatingly pleasurable. A warmth began to spread through his lower abdomen, a feeling akin to the onset of orgasm, but not quite. It was deeper, a slow climb toward a pinnacle that refused to materialize in the usual way.

He couldn't help but steal glances at the mirror. His body was taut, muscles standing out along his arms as he clenched the bedspread. Lisa's eyes, focused yet brimming with excitement, flickered up to meet his in the reflection. She gave him a knowing smile.

"Feel it?" she asked, voice low.

"Yes," he moaned, hardly able to form the word.

She pressed a little more firmly, intensifying the internal stimulation. Each stroke was like a wave cresting inside him--just enough to make his mind spin. He recognized the telltale throbbing that usually signaled the start of an orgasm, but something was different.

As her rhythm continued, he felt a subtle shift deep within, as if his body was preparing to release. His shaft throbbed, though not in the typical manner--this arousal was more diffuse, rooted in his core. The sensation wasn't the frantic, pulsing drive of a normal climax. Instead, it was a slow, inevitable build, making him hyper-aware of every inch of his body.

The Slow Drip

Lisa leaned forward, pressing her chest lightly against his back in a reassuring gesture. Her finger never stopped its hypnotic motion. Andrew's breath caught. He felt a sudden, gentle spasm in his pelvis. Something warm and liquid began to seep from his tip--he could sense it even before he saw it.

"It's starting," Lisa murmured. Her voice was thick with fascination.

Andrew angled his gaze in the mirror, but from this position, he could only see glimpses. A bead of milky fluid dripped onto the sheet. The peculiar feeling of something leaving his body--without the usual explosion of orgasm--made his head swim. It was akin to the lazy trickle of urination, but warm and utterly different in context, leaving him with both relief and an amplified yearning for a true release.

His body quivered at the odd contradiction: it felt good to let go, but there was no culminating pleasure to crash over him. Instead, each spasm teased him with the promise of what could be. This was a slow, drawn-out draining.

Extended Torment

He let out a low moan, equal parts frustration and pleasure. Lisa adjusted her angle, gently curving her finger so that each rub against his prostate coaxed more fluid out. A shiver ran up Andrew's spine when he sensed another warm droplet escaping.

"So close," he whispered, though "close" wasn't the right word. His usual sense of climax was absent; instead, he was suspended in a state of half-release, his body contracting in slow waves.

Lisa's breath hitched. "Yes," she purred, leaning in. She slid her other hand around his hip, carefully angling his shaft so that any discharge wouldn't just drip away unnoticed.

He caught sight of her face in the mirror: her cheeks were flushed, her lips parted. She was enthralled, gazing intently at the milky fluid steadily emerging in tiny increments. Her own excitement was palpable, fueling Andrew's desire. She finds this so hot, he realized, and the knowledge made him throb with unfulfilled lust.

The Mirror's Reflection

Every spasm was magnified by the mirror. He watched his own face contort in a mixture of relief and longing, watched his shoulders tighten, his hips tremble. Lisa kept up the unrelenting motion, massaging his prostate with smooth precision.

His mind flitted through a chaotic collage of thoughts: This is humiliating, This is exhilarating, I need more, I can't believe I'm letting her do this, I've never felt so connected.

He attempted to shift his weight, maybe to ease the intensity, but she placed a firm hand on his lower back. "Stay," she commanded. The gentle authority in her tone anchored him.

Lengthy, Lingering Release

Over the next several minutes--though it felt much longer--Andrew continued to expel small pulses of fluid. Each contraction left him feeling increasingly emptied yet still on edge. The ache for a real orgasm, one that would bring that brilliant burst of euphoria, escalated in his belly. Yet it remained just out of reach, replaced by this languid, maddening drip.

A part of him wanted to beg her to stop, to let him up, to let him stroke himself to a proper finish. But the rest of him relished the control she wielded, the trust required to give her the reins entirely.

At last, as the final pulses subsided, Lisa eased her finger out. Andrew's body sagged in relief, though not the same relief an orgasm would bring. His arms felt like jelly, his breathing ragged. She pressed a soothing palm along his spine, then slid off the bed momentarily.

When she returned, she had a tissue and a small glass of water for him. She used the tissue to dab away the lingering droplets at his tip. A final spasm forced out one last bead of fluid, which she caught between her gloved fingers. Then she lightly ran a single fingertip along his shaft, guiding that final drop forward. It was such a gentle, almost caring touch that Andrew couldn't help but shudder.

After the Milking

"Roll over," she said softly.

He did, body shaky, and she helped him settle onto his back. She peeled off the glove and tossed it aside. Then she cupped his face in her hands and kissed him, slow and tender.

"How do you feel?" she asked.

He swallowed. "Relieved, but... still frustrated."

She nodded, brushing a thumb over his lip. "That's the point. You get some relief, but not that mind-blowing end. It keeps you wanting."

Andrew closed his eyes, letting the weight of her words sink in. She was right; his body felt somewhat lighter, yet his mind still roiled with desire. In that moment, he yearned to make love to her, to claim a real orgasm. But she was in control--and that was both torturous and thrilling.

Lisa pressed a kiss to his forehead. "We'll talk about your reward later," she teased. Then she ran a hand through his hair. "Ready to be locked back up?"

His chest tightened with a complex swirl of defeat and fascination. Part of him wanted to protest, but he knew the answer that would pass his lips: "Yes... if that's what you want."

"It is," she whispered, retrieving the chastity device. Her eyes sparkled with satisfaction. "I want you to learn to behave--and to earn everything."

Chapter 3: Growth Outside the Bedroom

Over the next few weeks, Andrew fell into a rhythm with Lisa that extended far beyond these intense bedroom encounters. If anything, the dynamic they shared outside of sex deepened their bond in ways he hadn't anticipated.

Shared Responsibilities

He found himself at her place more and more often. Initially, he offered to help with small chores--taking out the trash, washing dishes--simply as a way to spend more time around her. But soon, it became a habit. Lisa might tease him that helping with household tasks was part of his "training," yet he knew she appreciated it on a real, practical level.

Each time he vacuumed the living room or folded her laundry, she'd give him that mischievous smile. "Good boy," she'd say, half in jest, half serious. The praise sent a tingle down his spine--and often made the chastity device feel tighter than ever.

Flirting and Consequences

Now and then, Andrew caught himself innocently flirting with strangers--a lingering glance at a friendly bartender, or a playful laugh with a female coworker. Each time, Lisa would either arch an eyebrow if she was present, or somehow know if she wasn't. It became a game of sorts, though Andrew always reassured her his affection was hers alone.

He enjoyed that surge of adrenaline, the knowledge that any stray flirtation might result in a text from her: Were you chatting up the waitress a little too eagerly?

And then, inevitably, a playful threat to keep him locked up longer. He marveled at how an act that used to be innocent--exchanging pleasantries with someone--now could spark such intense consequences. Yet, oddly, he felt more connected to Lisa for it. They'd established a constant line of communication about boundaries, trust, and accountability, turning everyday interactions into a subtle power play.

Deeper Dates and Conversations

Their dates weren't all about sexual tension. Often, they went out for dinner like any other couple, leaning across candlelit tables to discuss books, movies, childhood memories. They shared more about their past marriages, dissecting what went wrong and why.

Lisa opened up about feeling emotionally suffocated in her previous marriage--her husband had discouraged her from showing any sexual creativity. Andrew admitted how he and his ex-wife lost emotional intimacy over time, settling into a gray routine that sucked the joy from their relationship.

These confessions fostered an intimacy that wasn't just physical. It was emotional, intellectual--a synergy they'd never had as teenagers. They found solace in each other's stories, vowing that this time, they'd be honest and brave, no matter where that led.

A Weekend Away

One weekend, they drove to a small mountain resort two hours outside the city. The fresh air, pine trees, and cozy cabin vibe let them escape the usual humdrum. Over a campfire dinner, they sipped wine and held hands, occasionally exchanging heated glances. Andrew could feel the cage beneath his clothes, a constant undercurrent of anticipation, yet the weekend was surprisingly wholesome. They hiked, snapped photos of breathtaking vistas, and snuggled beside the fireplace when night fell.

Lisa teased him about the device once or twice. "Cold out there," she'd say, tapping lightly on the bulge of his jeans. "Bet that cage keeps things interesting." But they didn't engage in any intense play. It felt like a subtle test: Could their relationship withstand normalcy? Could they talk about future plans, families, hopes, and fears without the overshadowing presence of sex?

The answer was a resounding yes. In fact, it made their dynamic richer. By the time Sunday evening rolled around, Andrew felt more than just physically drawn to her--he was emotionally wrapped up in everything she was.

Chapter 4: Tensions Rise

Back from the mountain retreat, Andrew's desire for Lisa continued to build. She, on the other hand, seemed content to keep him locked a while longer. Every time he hinted at wanting more, she'd gently remind him that he didn't decide his release date--she did.

Conflicting Emotions

The chastity cage had gone from novelty to a regular fixture. Andrew was torn between gratitude for the erotic tension it sustained and frustration at his lack of control. Some mornings, he'd wake up throbbing against its confines, cursing the predicament. But then he'd recall how Lisa's eyes sparkled every time she teased him about it, and he found himself weirdly grateful for the frustration. It kept him tethered to her, constantly aware of her power in the relationship--and, oddly, of the depth of his own commitment.

They discussed it openly. Late one evening, lying together on the couch (with Andrew still locked), he confessed, "It's not easy, you know. Wanting you all the time and not being able to do anything about it."