Chapter 25: Double Date Disaster
The double date was Emily's idea—a way to push Alex's boundaries further while keeping the slow burn of humiliation alive. She had arranged it with Aunt May over text the next morning: dinner at a quiet Italian restaurant downtown, just the four of them. Emily, Alex, Aunt May, and a "surprise guest" Emily refused to name. Alex's stomach twisted with nervous excitement the moment she told him.
"You'll dress pretty," Emily said while braiding his long hair into two loose pigtails—cute, girlish, perfect for tugging. "No coat. No hiding. Everyone will see what you are."
Alex's outfit was chosen with care: a short black pleated skirt that barely covered his plumped ass, sheer enough to hint at the black lace thong underneath; a cropped white blouse unbuttoned low to show the black lace bralette cradling his full B-cups—nipples dark and erect beneath the cups; thigh-high stockings clipped to a garter belt; and the ever-present pink chastity cage locked tight, pre-cum already leaking into the thong pouch. The anklet chimed softly with every step. Makeup was light but deliberate: glossy pink lips, mascara to make his softened eyes pop, a touch of blush on his high cheekbones.
Aunt May picked them up in her SUV—wearing a deep red wrap dress that hugged her curves, cleavage on display, heels clicking confidently. She smiled when she saw Alex—eyes raking over the outfit.
"You look… edible," she said softly, reaching out to tug one pigtail. "Ready to be shown off?"
Alex nodded—voice breathy, seductive. "Yes… Aunt May. I'm ready."
They arrived at the restaurant—a small, dimly lit place with red velvet booths and candlelight. Emily had reserved a corner booth—semi-private, but visible to waitstaff and nearby tables.
The surprise guest was waiting: a tall, broad-shouldered man in his late 30s—dark hair, sharp jaw, wearing a tailored blazer. Aunt May introduced him as Mark—her "old friend from yoga class." He shook Alex's hand—lingering—eyes flicking down to the visible bra strap and the skirt hem.
"Nice to meet you… Alex," Mark said, voice low. "Emily told me you're… special."
They slid into the booth: Aunt May and Mark on one side, Emily and Alex on the other. Alex sat pressed against Emily—skirt riding up, stockings visible, cage bulge pressing against the fabric.
The waiter—a young guy, early 20s—took their drink orders. His eyes kept drifting to Alex's chest, then lower. Emily noticed—smiled sweetly.
"He's shy," she said to the waiter. "But he loves attention."
Alex blushed—cage throbbing.
Dinner started innocently: wine, appetizers, small talk. But Emily steered it quickly.
"So Mark," she said casually, sipping her red, "Aunt May tells me you're single. And… adventurous."
Mark grinned—eyes on Alex. "I can be. Depends on the company."
Aunt May's hand slid under the table—rested on Mark's thigh—then higher. Mark's breath hitched.
Emily leaned toward Alex—whispered loud enough for them to hear: "Show them, princess. Lift your skirt a little. Let them see how locked you are."
Alex's hands shook—fingers finding the hem—lifting slowly. The skirt rose—revealing the black lace thong, the pink cage bulging obviously, pre-cum glistening on the bars.
Mark stared—jaw slack. Aunt May bit her lip—hand sliding higher on Mark's thigh.
"Jesus," Mark muttered. "That's… real?"
Emily laughed softly. "Very real. He hasn't sticky white milkin weeks. He leaks instead."
Alex whimpered—voice seductive, moaning at the edges. "It's true… I'm locked. For Mistress. For Aunt May. For… anyone who wants to see."
The waiter returned with salads—froze when he saw Alex's exposed lower half. Emily didn't let Alex cover up.
"Keep going," she told the waiter. "He likes being seen."
The waiter swallowed—set the plates down—eyes locked on the cage—then hurried away, face red.
Mark leaned forward—voice low. "You're okay with this?"
Alex nodded—tears pricking his eyes. "I need it. Please… look. Touch if you want."
Mark reached under the table—fingers brushing Alex's thigh—then higher—cupping the cage through lace. Alex moaned—high, needy—hips twitching.
Aunt May watched—eyes dark—then slid her own hand under—fingering Alex's ass cheek—squeezing the plump flesh.
The table hid most of it—but nearby patrons noticed the soft moans, the shifting bodies.
Emily ordered more wine—casual—while Mark stroked the cage slowly—thumb circling the tip slit—smearing pre-cum.
Alex bit his lip—trying to stay quiet—but moans escaped—seductive, pornographic—drawing stares from other tables.
A couple at the next booth whispered—then stared openly. A woman smiled—bit her lip.
Mark leaned in—whispered: "You're dripping like a faucet."
Alex nodded—tears slipping down. "Yes… I can't stop. Please… don't stop touching me."
Aunt May's fingers slid between his cheeks—circled his hole—then pushed in—slow, one finger—then two.
Alex gasped—loud enough the waiter heard from across the room—dropped a spoon—bent to pick it up—saw everything—froze.
Emily laughed—soft. "He's close. But he won't cum. Ever. Unless I say."
Mark stroked faster—fingers slick with pre-cum. Aunt May curled her fingers inside—hitting that spot.
Alex sobbed—body shaking—cage pulsing—pre-cum pouring onto the booth seat.
He came close—dangerously close—then Emily pinched his nipple hard through the blouse—pulling him back from the edge.
"No," she whispered. "Not yet. Not ever."
Alex cried—real tears—body trembling. "Please… Mistress… Aunt May… Mark… I need more. Please… take me somewhere private. Use me. All of you."
Mark looked at Emily—then Aunt May. "Let's go. My place is five minutes away."
They paid—quickly—Alex walking out with skirt still hiked, cage and stockings visible—drawing stares from the entire restaurant. Whispers followed them out.
In Mark's apartment—modern, minimalist—clothes came off fast.
Alex knelt in the center of the living room—naked except stockings and cage—braid undone, hair fanning around him.
Mark fucked his mouth first—deep, rough—while Aunt May rode his face—grinding against his tongue. Emily watched—fingering herself—directing.
They switched—Mark in Aunt May's lower mouth—Darius-style thrusts—while Alex licked her clit from below—then cleaned Mark's meat rod between thrusts.
Emily finally let Alex be used—Mark bending him over the couch—fucking his ass slow—while Aunt May sucked his nipples—Emily whispering filth in his ear.
Alex sobbed—pleasure and denial crashing together—cage pulsing uselessly—body shaking.
They came—Mark filling his ass—Aunt May squirting on his face—Emily riding his tongue.
Alex collapsed—covered, leaking, owned.
The system chimed—soft, triumphant.
[Quest Complete: "Double Date Disaster"]
[Reward Granted: 5000 SP, Feminization Trigger (Full B-Cup Consolidation & Nipple Thickening), Taboo Group (+180% arousal from multi-partner family scenes). Current SP Total: 29750 New Passive: Date Humiliation (Arousal quadruples in public/social date settings when exposed/used).]
Warmth flooded his chest—B-cups firming, rounding perfectly—nipples thickening into sensitive, dark peaks.
Aunt May pulled him into her lap—kissed him gently.
"Stay with us," she whispered. "Always."
Alex nodded—tears of bliss.
"Yes… Aunt May. Forever."
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