Chapter 21

The group reconvened on the deck after dinner — burgers, baked beans, coleslaw, mac & cheese, wine, laughter — the anticipation of what was to come continuing to build. The sun had set, string lights glowing softly overhead. Holly pulled out the bowl again.

“Same game as last night,” she announced. “Men draw women’s names. One extra woman draws a number for the threesome room.”

Everyone settled in, wine glasses refilled, anticipation thick in the air.

Holly held the bowl high. “Gentlemen. Let’s go.”

Dr. Richard reached in first, unfolded the paper, and smiled slowly. “Holly.”

CeCe laughed. “Nice. The principal gets mommy then daughter. I like it.”

TD drew next, unfolded his slip, and looked at Beth with a grin. “Beth.”

Beth’s eyes lit up. “Oh, I’ve been waiting for this.”

Willie reached in, drew, read the name, and chuckled. “Jenna.”

Jenna grinned. “Nice. It’s been since what Tuesday? Good. I want that cock again.”

“Be careful what you wish for.”

“Bring it. It’s not like I haven’t had that cock in every hole already big boy.”

James drew last, pulled the slip, and looked at Debbie. “Debbie.”

Debbie smiled. “Perfect. Been thinking about you all day.”

CeCe pumped her fist, reaching into the number bowl. “Back to back threesomes for this bitch!” She unfolded the slip. “Three.”

Holly glanced around. “Room three gets the threesome. That’s the guest room with the lake view.”

CeCe laughed. “Ahhhh, Willie and Jenna. You two better not make me be the referee.”

Jenna winked. “Don’t worry, Willie just likes to act tough.”

They finished their drinks, the night air cool on skin, anticipation thick.

Then they paired off — hands linked, soft kisses, bodies pressing close as they headed to their assigned rooms, the cabin quiet except for the lake and the soft creak of doors closing.

Dr. Richard and Holly slipped into the master bedroom, the door clicking shut behind them with a soft, final sound. The room was dimly lit by a single bedside lamp, casting warm amber shadows across the king sized bed. Yesterday’s red silk sheets had been replaced by a fresh set of deep purple ones, still crisp and cool to the touch, the faint scent of lavender laundry detergent lingering in the air.

Holly turned to him slowly, eyes already dark with anticipation, breath coming a little faster. She stepped close enough that her bare nipples brushed his chest, sending a small shiver through both of them.

“You drew my name tonight,” she said, voice low and teasing, hands sliding up his chest, nails dragging lightly over his skin. “First time with the principal. You going to give me a proper lesson?”

Dr. Richard’s gaze darkened, one large hand sliding into her hair, fingers threading through the strands before closing in a firm but careful grip. He tugged her head back gently, just enough to expose the long line of her throat, forcing her to meet his eyes.

“You’ve been a very naughty student,” he murmured, voice deep and measured. “I think you need extra credit tonight.”

Holly moaned softly at the pull, lashes fluttering, lips parting. “Then teach me, sir. Show me what happens to girls who beg for more.”

He studied her face for a long moment — cheeks flushed, pupils blown wide, the faint freckles across her nose standing out against her heated skin. His thumb brushed the edge of her jaw, slow and deliberate.

“Earlier on the deck,” he said quietly, “when you were joking with the others ... you said something about being a teenager. Did I hear that right?”

Holly’s lips curved into a slow, wicked smile. She didn’t try to pull away from his grip; instead she leaned into it slightly, letting him feel the way her pulse jumped under his fingers.

“You did,” she whispered. “Turned eighteen in March.”

Dr. Richard’s breath caught — barely audible, but she felt it in the subtle tightening of his hand in her hair. His eyes flicked over her face again, searching, calculating.

“Eighteen,” he repeated, almost to himself. The word hung between them, heavy and electric. “I thought you were at least in your early twenties. Had me fooled for sure.”

Holly tilted her head as much as his grip allowed, looking up at him through her lashes. “Does that bother you?”

He exhaled through his nose, the sound rough. “It should. But it doesn’t.” His free hand slid down her side, fingers tracing the curve of her waist, then lower, cupping her ass possessively. “It makes me want to be very, very careful with you ... and very, very thorough.”

Holly’s breath hitched. She licked her lips slowly. “Good. Because I’ve been thinking about something else all day.” Her voice dropped to a whisper, intimate and filthy. “Have you ever fucked any of your students before?”

Dr. Richard’s jaw tightened, eyes flashing with something dark and hungry. He leaned in until his lips were a breath from hers.

“Never,” he said, voice gravel-rough. “Not once. Other teachers, my secretary, a couple of former students, but never a current student.”

Holly’s smile turned feral. “Too bad I wasn’t one of your students. I would have fucked you right there in your office.”

“I would have wanted to, no doubt, but I wouldn’t have done it. At least until graduation night anyway.”

“Enough talking. I’ve learned my lesson, principal. Now it’s time for my punishment.”

He kissed her then — hard, claiming, teeth grazing her lower lip, tongue sweeping in to taste her fully. Holly melted into it, hands clutching his shoulders, nails digging in as she pressed her body against his, feeling the thick ridge of his cock trapped between them.

When he finally pulled back, both of them were breathing hard.

“On the bed,” he ordered, voice low and controlled. “Face down. Ass up.”

Holly obeyed instantly, crawling onto the purple sheets, lowering herself onto her stomach before lifting her hips high, knees spread, offering herself completely. The moonlight painted her skin silver, highlighting the faint red marks still visible on her ass from Willie’s hands the night before.

Dr. Richard stood behind her for a long moment, simply looking — taking in the sight of her spread open, pussy already glistening, tight little asshole winking in the low light.

“Beautiful,” he murmured, almost reverently.

Then he dropped to his knees.

His hands spread her wider, thumbs pulling her cheeks apart. He started with long, slow licks along her slit — tasting her arousal, gathering it on his tongue — before moving higher. His tongue circled her asshole in lazy spirals, teasing the rim, then pressing flat against it, licking with firm, steady pressure.

Holly whimpered, hips twitching. “Oh fuck ... yes ... eat my ass...”

He groaned against her skin, the vibration making her gasp. One hand slid between her legs, fingers finding her clit — rubbing slow circles — while his tongue pushed deeper, probing inside her ass, fucking her with wet, deliberate strokes.

Holly’s moans grew louder, more desperate. “Don’t stop ... please ... get me ready for your cock...”

He worked her open patiently — tongue and fingers in tandem — until she was trembling, dripping, her asshole soft and relaxed under his mouth. Only then did he rise.

He slicked his cock generously with lube, pressed the thick head against her back entrance, and pushed in — slow, relentless, inch by inch. Holly’s breath hitched, body tensing, then relaxing as he sank deeper, filling her completely.

“Fuck ... so big ... stretching my ass...”

Dr. Richard paused when he was fully inside, letting her adjust, hands stroking her back in soothing circles.

Holly exhaled shakily. “Move ... please ... fuck me...”

He started slow — long, measured strokes — pulling almost all the way out before sliding back in, letting her feel every ridge, every vein. Holly moaned, pushing back to meet him, the stretch turning from burn to pleasure.

“Harder ... please ... fuck my ass harder...”

He obliged — speed building, hips snapping forward, balls slapping her pussy with every thrust. One hand slid around to her throat — not choking, just holding — while the other gripped her hip, anchoring her as he pounded into her.

“Take it,” he growled. “Take every inch in your tight little teenage ass.”

Holly’s moans turned raw, desperate. “Yes ... FFFFUUUUUCCCCCKKKK ... own my ass ... make it yours...”

He reached around with his free hand, fingers finding her clit — rubbing fast, firm circles. Holly shattered — ass clenching hard around him, pussy squirting untouched, soaking the sheets in hot pulses. Dr. Richard kept fucking her through it. Deep and relentless.