Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 19 by Linda007 Linda007

What happens next

She wants to stop

Sunday – November 30, 2025, Linda's Parents' House / Phone Call with Rebeka, Afternoon

The separate Sunday brought no school or work, just quiet reflection amid family brunch. Linda's mind replayed the alley in vivid flashes—the homeless man's groping hands, Trent's humiliating taunts—leaving her feeling dirty and conflicted: This has gone too far... sucking Josh's bully, getting railed by a stranger? I need to stop before it ruins everything. But Josh's excited texts from last night echoed, his love for the tease binding her like chains; for him, she'd endure, pushing thoughts of ending it aside. That afternoon, she confided partially in Rebeka during a long phone call—her best friend, the bubbly colleague who'd joined her fabricated shopping trip lie. "Rebeka... remember Trent from Josh's stories? I met him today for coffee, and it turned into... more. I gave him a blowjob in an alley. It was awful—he's such an arrogant creep." Rebeka gasped, then laughed in shock: "Girl, what? For Josh's fantasy? You're wild... but be careful; that sounds risky." Linda skirted the homeless part entirely, tears welling as she admitted, "I hate it, but seeing Josh so turned on... I can't stop yet." Rebeka urged caution—"Tell me if it gets worse"—leaving Linda feeling supported but more isolated in her full secrets, the confession easing some weight without revealing Rob or the raw violation.

No Rob contact that day—he respected her "once a week" boundary—but his lingering dominance haunted her, a reminder of the other thread pulling her deeper.

Monday – December 1, 2025, Josh's Office, Morning

Josh arrived at work buzzing with secretive excitement, the partial truth from Linda fueling his fantasies all weekend. Trent, spotting him in the break room, couldn't resist crowing—his thin, scarecrow frame leaning in with a filthy grin: "Your girl's mouth is magic, man—tight and eager in that alley. Bet she doesn't do that for you." The words hit Josh like a punch, jealousy flaring at the intimate detail, but it morphed into arousal, his cock twitching under his desk as he imagined it. He's such a repulsive prick... but knowing she sucked him off for me? It's **** and heaven. Trent kept it up throughout the day—whispering "Sloppy seconds?" during meetings—no outright bullying, but the lewd taunts made work electric, Josh texting Linda mid-afternoon: "Trent's bragging... so jealous, but fuck, it's hot." At school, Linda endured Rob's subtle stares in the hallway, his ugly eyes promising their next session, her pussy clenching involuntarily despite the revulsion—Stop this madness, she thought during lunch, but Josh's messages pulled her back in.

Tuesday – December 2, 2025, High School Teachers' Lounge / Rob's Apartment, Evening (Separate Day)

Linda's workday dragged with Rob's presence looming—he cornered her in the teachers' lounge during break, whispering, "Tomorrow's our day—my place after school. Wear the red teddy." His commanding tone stirred unwanted heat, her body remembering the massive dildo despite hating his old, unattractive form. I should say no... end it all, she agonized, thinking of the alley's humiliation, but the cycle with Josh—his growing obsession with Trent's updates—made her nod. That evening at her parents', Trent messaged her: "Thinking about that blowjob—round two soon?" She ignored it, conflicted arousal bubbling as she pictured Josh's reaction if she teased back. Josh, at work, faced more of Trent's barbs—"Bet Linda's pussy's as sweet as her lips"—bothering him deeply but turning him on, leading to a frustrated, condom-bound fuck with Linda later (via video call, since separate), where he pounded her roughly, groaning about "my slutty girl."

Rebeka pulled her aside after classes: "You okay? You seem off." Linda confessed more—"Trent's messaging me now... it's getting creepy"—venting her disgust, Rebeka hugging her virtually: "Dump that dynamic—Josh will understand." But Linda's resolve wavered; for him, she'd continue.

Wednesday – December 3, 2025, Rob's Apartment, 4:00 p.m. (Together Afternoon, but Lied to Josh)

Adhering to her once-a-week rule, Linda lied to Josh about a "late meeting" and met Rob, stripping into the red teddy upon arrival—the sheer panels making her look devastatingly hot, her 34D boobs and ass on display. He fucked her roughly on the couch, his 9-inch cock raw inside her (per his rule), the camera rolling as she moaned despite the repulsion: "God, it's so big... harder!" She came twice, hating herself for enjoying the stretch, the alley's raw memory amplifying the guilt. This has to stop—I'm losing myself, she thought post-orgasm, but Rob's gruff "Good slut" and the fresh video kept her trapped. Josh at work endured Trent's escalating filth—"Gonna bend her over my desk next"—jealousy spiking his productivity to zero, but arousal leading to secretive masturbation in the bathroom. Linda, back home, felt powerful yet broken, texting Josh teasing Trent updates to keep the facade.

Thursday – December 4, 2025, High School / Josh's Office

School brought Rob's smug glances, his hand brushing her ass in the empty hallway—a risky grope that made her flinch but wettened her. End it, she urged herself during a free period, journaling her turmoil: the embarrassment, the unwanted highs, the fear of losing Josh if she confessed everything. But his loving texts—"Love how brave you are for me"—dissolved her will; she'd endure. Trent cornered Josh by the copier: "Linda's tits felt great in my hands—wait till I fuck her proper." Josh seethed, the humiliation turning him on unbearably, snapping at a colleague in frustration before begging Linda for more details that night.

Rebeka joined her for lunch: "Spill—Trent still harassing?" Linda broke down partially—"The alley was bad, and Rob... it's complicated"—hinting at the affair without names, Rebeka horrified: "Girl, stop before you get hurt. Talk to Josh." The advice resonated, but Linda's addiction to Josh's excitement held her.

Friday – December 5, 2025, Various Locations

The week closed with Trent texting Linda a dick pic—"Miss this?"—her deleting it in disgust but screenshotting for Josh, who exploded with jealous praise: "Send him something flirty back—tease!" At work, Trent's comments to Josh peaked—"Your girl's a keeper; gonna steal her"—bordering on bullying again, but Josh channeled it into bold fantasies. Rob sent a video clip from Wednesday, demanding "Next week—bring the strappy one." Linda at school felt exhausted, her body sore from secrets, mind screaming Stop! Tell Josh everything and quit, the cumulative weight—alley stranger, Rob's dominance, Trent's arrogance—crushing her. But curled up with Josh that together evening, his adoring eyes as she whispered more teases, she endured: for him, she'd continue the spiral, burying the full truth deeper, her love twisted into **** complicity.

Saturday – December 6, 2025, Linda's Parents' House / Josh's Parents' House, Morning to Afternoon

The weekend brought a festive chill to the air, early December decorations twinkling in neighbors' windows, but Linda's mind was a storm of contradictions as she prepared for the together day with Josh. Waking late after a restless night—haunted by Rob's video demands and Trent's unsolicited texts—she rifled through her closet, landing on a sexy Santa's helper outfit she'd bought on impulse last holiday season: a form-fitting red velvet mini-dress with white fur trim along the low-cut neckline and hem, hugging her slim hourglass figure and accentuating her full 34D boobs while the short skirt barely skimmed her round ass. Paired with thigh-high black stockings, red heels, and a jaunty elf hat, it transformed her into a playful, provocative vision—festive yet undeniably hot, her beautiful face glowing under subtle makeup as she posed in front of the mirror. This is silly... but if it teases Trent like Josh wants, maybe it'll keep things exciting, she thought, snapping a few mirror selfies: one from the front showing off the cleavage plunge, another turned sideways to highlight her curves. Excitement bubbled despite herself—the outfit made her feel sexy, powerful—but guilt nipped at the edges, the alley's raw memory still fresh.

Before heading to Josh's, she hesitated, phone in hand, then sent one of the tamer pics to Trent via message: "Holiday spirit—thought you'd like this. " No caption beyond that, playing the slow-tease game Josh loved, her stomach twisting at the thought of his arrogant reply. Trent responded almost instantly: "Fuck, you look like a gift I wanna unwrap. When can I see the real thing?" The sleaze made her skin crawl—He's so disgusting, that ugly scarecrow face leering at my photo—but she forwarded it to Josh with a winking emoji, driving over with a mix of dread and illicit thrill.

Saturday – December 6, 2025, Josh's Parents' House, 2:00 p.m.

Arriving at Josh's parents' house (his folks out for errands), Linda modeled the outfit for him in the living room, twirling with a shy grin as the elf hat jingled. "What do you think? Got it for the season... and maybe some teasing?" Josh's eyes darkened with immediate hunger, pulling her close: "You look incredible—like a sexy elf straight out of my fantasies. Send that to Trent?" She nodded, showing him the exchange, and his arousal spiked visibly, cock hardening against her as he kissed her neck. "He's obsessed... imagining him staring at this pic, stroking to it, dying to fuck you senseless. God, it drives me wild." They tumbled to the bedroom, clothes shedding hastily—the Santa dress hiked up, her black lace panties (from the mall) tugged aside—but she reminded him breathlessly of the condom: "Babe... wrap it up." Josh groaned in frustration, rolling one on quickly, but the barrier didn't dull his intensity; he entered her roughly, thrusting deep into her wet pussy, hands gripping her boobs through the fur-trimmed fabric.

As they made love—Josh pounding her missionary style, the bed creaking under them—his mind was consumed not by her soft moans or the way her stockings slid against his skin, but by Trent: That repulsive bully, getting hard over my girl's pic... he'd kill to be here, groping her ass, filling her raw like I can't. Fuck, it's so hot how she teases him for me. He panted it aloud between thrusts: "Trent loves this outfit... bet he'd rip it off and fuck you right now, that skinny dick of his owning you." Linda hated Trent with every fiber—his arrogant, full-of-himself attitude, the ugly scarecrow build, thinning hair, and beady eyes that screamed unattractiveness—but hearing Josh voice it turned her on for some reason, an unwelcome heat coiling in her core despite the revulsion. Why does this get me? He's disgusting... even his cock looked so ugly, pale and veiny in that alley, she thought, her pussy clenching around Josh's condom-sheathed length as the words pushed her closer. The taboo of it—the man she loathed invading their intimacy—amplified everything, her nails digging into his back as she came hard, crying out, "Yes... imagining him wanting me!"

Josh followed soon after, groaning into her neck as he filled the condom, collapsing beside her breathless. "That pic's gonna haunt him... thank you for sending it." Linda lay there, post-orgasm glow fading into conflict, her body sated but mind racing. I need to meet Trent again... maybe suggest a holiday party excuse, or say I'm grabbing drinks after work? The ideas bubbled up unbidden, a way to escalate the tease for Josh's sake, but picturing it soured her instantly: Trent's repulsive grin, his slim, unappealing cock twitching in anticipation, the arrogance making her want to gag. No... he's so unattractive, such a creep—why can't I just stop? Yet, for Josh—his excited eyes, the way he worshipped her through the kink—she'd endure, plotting the next encounter even as disgust roiled in her gut, the Santa's helper dress crumpled on the floor like a symbol of her tangled desires.

What happens next?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)