Into the Deep End: Jenna’s Choice

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Saturday, June 26th, 1999

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The coarse cotton of Lee’s old Dallas Cowboys shirt scratched gently against Jenna’s bare skin as she swung her legs toward the cold carpet. A shiver ran through her at the morning chill as it brushed her exposed hips. Lee lay beside her, utterly exhausted from his grueling thirteen-hour shift at Target, now deep in oblivious sleep, muffled snores blending with the quiet of their apartment.

Her hand slipped beneath the pillow, fingers brushing the delicate silk of the black panties Nikki had given her. With careful precision, Jenna tucked them securely within the pillowcase’s lining—hidden away where Lee would never find them.

She padded softly to the bathroom, closing the door behind her with a whisper. Gratefully, she grabbed her toothbrush, scrubbing away the stubborn tang of white wine mingled with the lingering echo of last night’s forbidden thrill. Staring into the mirror, she lifted the hem of her oversized tee. The skin beneath was no longer raw or swollen from the touch that had unsettled her on Nikki’s couch, but a dull ache throbbed low in her pelvis—a constant reminder of the control Nikki held.

Memories of yesterday’s events flickered through her mind as she moved into the living room. Quietly, she gathered scattered clothes before Lee could awaken. She unfolded the Dillard’s and American Eagle shopping bags on the kitchen table with a bittersweet smile. Surely Lee had rifled through the new clothes and those tantalizing underwear Nikki teased him about when he returned late last night. Possibly, he’d even peeked at the receipts.

Her heart stuttered when she bent to retrieve her denim shorts from the floor—twisted, out of place. Inside the leg hole lay the Calvin Klein thong, damp and out of position. Lee had definitely touched them.

Panic tightened around her chest. Her cover story had held, but what if Lee woke now and reached out? His fingers would meet skin, smooth and bare. She wasn’t ready for him to discover her shaved secret. She needed a shield, a barrier to protect herself from exposing too much too soon.

Frantically, Jenna stuffed the shorts, thong, and a Tommy polo into the laundry hamper, then grabbed the Umbro running shorts she’d worn the day before, along with a sports bra and a tight compression top.

Part of her craved the comfort of simple white cotton panties, a layer to feel safe against her skin. Yet Nikki’s voice echoed in her mind, demanding she sleep bare. Yielding to the lingering power of that command, Jenna slipped into the loose running shorts with nothing underneath. The cool nylon slid freely against her skin as she slipped quietly out of the apartment, heading down to the fitness room to drain off her restless desire on the elliptical machine.

She pushed herself mercilessly, sweat soaking her shirt as she battled the restless fire burning beneath her skin. Timing her return carefully, she stepped through the front door, nearly dripping minutes before Lee had to leave for work. The sweat-soaked clothes and racing heartbeat acted as a perfect deterrent—keeping his hands at bay.

Lee bustled in the kitchen, juggling the toaster and syrup for his Eggo waffle. His face brightened at the sight of her.

“Up early, babe,” he remarked, eyeing her. “You were out cold when I got home last night.”

“Yeah,” Jenna murmured, forcing a gentle smile. “I couldn’t fall back asleep. Too nervous about training starting Monday. I thought a run on the elliptical might clear my head.”

Leaning casually against the counter, Lee’s smile twisted into a teasing smirk. “About last night… I stumbled over your clothes on the floor. Looks like you and Nikki had a wild time. That new thong in those tiny shorts? Definitely wet, babe. What was going on?”

A rush of heat flooded Jenna’s cheeks. Eyes cast downward, she played innocent. “Oh Lee, stop! I was just so tired when I got home, I took everything off and forgot to pick up the clothes.”

Lee chuckled, crossing his arms. “That’s not all. When you and Nikki came by the store, I noticed you weren’t wearing a bra under that new Tommy Hilfiger polo.”

Her voice softened, wrapping her arms around his neck while letting her damp top keep any closer contact at bay. “Nikki’s the reason for all that. She told me about the natural look for girls like me with smaller chests—no bras, unlined Calvin Klein ones from Dillard’s. It’s the city trend. She said it would help me make better tips at Chili’s; the less structured look is more approachable, more youthful—like you always said, the cost of doing business.”

Holding his gaze, she traced his shoulders gently, just as Nikki had trained her. “She said I need to embrace skimpier clothing and blend into the city vibe. Padded bras make me look stiff, but this natural silhouette shows a little leg, a little jiggle—it’s what works.”

Lee’s pride swelled, his voice hungry. “A city trend, huh? How was the movie at her place?”

“Just a chick-flick—you’d have been bored,” Jenna replied smoothly, hoping he’d accept the explanation.

“But what about that damp thong? Watching a movie doesn’t usually do that.”

Her breath hitched — admitting this was mortifying — but honesty was the best path. “Honestly… being out there, feeling the breeze and wearing those shorts—shorter than anything I’ve worn—got me worked up all day.”

Lee’s voice deepened. “It turned you on?”

With a wicked spark, Jenna lowered her lashes and stepped fully into the role. “Yeah… and when I came by your store, some guys were definitely staring. I felt it. So, tell me, Lee… how does it feel knowing the guys at work noticed your little wifey like that? And, be honest, did you like seeing me braless?”

His jaw dropped, ego soaring. “Babe, it drove me wild. The guys couldn’t take their eyes off you. Nikki’s amazing—and those cookies she sent, that note about sharing something sweet… so thoughtful.”

The phrase “sharing something sweet” lingered between them, loaded with secret meaning that made Jenna’s skin tingle.

“Yeah… she’s very thoughtful,” Jenna whispered.

Lee reached for her waist. “I don’t have to be at the store for another half hour…”

“Oh no, you don’t!” Jenna cut him off with a sly smile, stepping back. “I promise you a private fashion show Sunday night. I’ll model all my new clothes Nikki picked out. You’re going to love it.”

“Sunday night? Deal,” Lee grinned.

“But the new underwear? You’ll have to wait.” Jenna held up the final shield. “My period’s coming, so I’m already feeling bloated and… not very sexy.”

“I can’t wait to see you in those new outfits. See you tonight, beautiful!” He kissed her cheek, then dashed out the door. Jenna let out a sigh of relief and collapsed against the counter.

As promised, Sunday brought relief with the start of her period. That natural barrier eased her nerves, providing time before Lee might discover her secrets.

Monday marked the beginning of formal training at Chili’s. Jenna endured endless hours standing on unforgiving tile floors, muscles aching and back tight. Nikki’s silence for five days sucked the energy out of her, and the isolation gnawed at her soul.

Midweek, after a long lunch shift, Jenna slipped into her apartment alone. Lee was still at work, hours away. Craving connection, she pulled out the neon orange thong bikini Lee had gifted her on their honeymoon. Wearing it in front of the mirror, the provocative fabric clung to bare skin, igniting both guilt and yearning. Though not bold enough to wear it to the pool, donning it privately only intensified her hunger for Nikki’s approval.

Thursday night’s dinner shift shifted up the intensity. Without the natural cushion of pubic hair, Jenna’s bare skin rubbed constantly against the sheer lace and tight shorts of her uniform, every step amplifying the electric friction. Sneaking into the restroom during a lull, she leaned breathless against the stall door, fingers trembling over her waistband, aching to relieve the growing ache. Yet Nikki’s command thundered through her mind: “Absolutely no touching—stay desperate and starved for me.” Compliance held her back as the craving knotted deeper.

Her usual cheerful mask cracked under pressure. Irritable and sharp, she snapped at coworkers, attracted Tony’s attention. Later, a whispered report reached Nikki: Jenna was fraying, ready to break.

Friday morning, the pent-up tension shattered with Nikki’s call. Her velvet voice edged with control, probing Jenna about her training and mood. Vulnerable, Jenna admitted the struggle. Nikki smiled through the phone, promising certification today and hinting at a celebration to come—if Lee agreed, and Jenna earned it.

Plans formed quickly. Nikki commanded Jenna to embrace the upcoming family visit and to wear one of her new outfits proudly—a look cute but not scandalous. Then her tone lowered, focusing on Jenna’s swim days by the pool. Nikki delivered the ultimatum: she must decide to remain safe in the shallow end—returning to old routines and restraint—or to “swim in the deep end” with her.

Swimming in the deep end meant surrender, strict rules, and absolute control. Moments might feel suffocating, like drowning, but it promised freedom and transformation. Nikki ordered Jenna to bring her sheer white honeymoon bikini on Monday at three sharp. Show up, and they move forward. Skip it, and the relationship ended.

Jenna stood frozen, the ultimatum vibrating through her. All weekend, she wrestled with the choice.

Friday night, she passed her final test with flying colors. Closing crew invited her out, and with Lee’s blessing, she went. A sweet buzz and the thought of the impending judgment weighed on her.

The weekend’s family visit arrived—Lee’s brother and fiancée filling the apartment with warmth and tradition. Outwardly, Jenna played the familiar country bride; inside, her mind wandered far away. The weekend was filled with crowds, sun, laughter, and contrasts.

Saturday night, Lee tried to pull her close, but she deftly dodged, citing the lack of privacy and the ever-present risk of discovery. When Danielle emerged in pajamas mid-evening, confirming Jenna’s caution, Lee’s frustration gave way to reluctant acceptance.

Sunday, the family moved by the poolside. Jenna slipped into the turquoise water, swimming quietly out to the deep end where the water swallowed her feet and the world faded. Suspended in silence, she heard the distant chatter but felt utterly alone, the old life no longer enough.

Her fingers gripped the pool’s edge as she replayed Nikki’s words. The shallow end was safe and predictable. The deep end was unknown but liberating.

With a slow breath, Jenna released her hold. The water enveloped her as she submerged beneath the surface, symbolizing her complete surrender to the deep end, to Nikki’s control, and to the new life awaiting her.

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