#36: The Headmaster's Basement
This is a work of fiction. Names, characters, events, and incidents are the products of the author's imagination. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are consenting adults over the age of 18.
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Back at Royal Oaks, the Headmaster helped Liza out of his car and into his house. She was still feeling disoriented from the champagne, but at least she was no longer dizzy. She could walk, but her muscles seemed reluctant to respond.
It was the first time she had ever been in his house; she had no idea what to expect. He unlocked a door and guided her down a steep flight of stairs.
He stripped her and then attached leather shackles around her wrists and ankles and a thick belt around her waist. Liza wanted to resist - she was starting to worry about what he might do - but she could barely control her muscles. Was this what being drunk was like? She didn't think so, but her experience was quite limited.
"No... I can't..." she tried.
"Oh, it's far too late for that, Miss McCoy. That helpless feeling is caused by a drug I added to the first cup of piss you drank. It masked the taste quite well, don't you think?"
She tried to struggle, but the ropes and the drug prevented her from moving much.
"Ah, don't worry, it will only last a few more hours. That should be plenty of time for what I'm going to do to you."
"I don't want..." she tried again.
"It's not about what you want. Tonight we're doing what I want, and I have special plans for you."
She could hear an electric humming as some mechanism tightened the ropes secured to the cuffs. She was lifted off the floor as her arms and legs were pulled up, suspending her like a swing.
The room was softly backlit with blue and red lights; her eyes adjusted quickly. She was hanging in the center of the room, suspended from a large round disk with ropes feeding out from each side.
There were many other objects along the walls. The wall to her left had shelves holding an impressive collection of dildos, vibrators, and other sex toys, some unlike anything she had ever imagined. To her right, it looked like a stable tack room, with harnesses, whips, and riding crops. But what drew her attention most was the Headmaster. He was standing near her head, naked, with his impressive cock dangling just inches from her face.
"Open," he ordered. He inserted a large metal ring, forcing her mouth open as wide as it would go, though it didn't interfere with her breathing. A leather strap running behind her head secured it in place. Another strap attached to the first, and ran over the top of her head. It ended in two small curved prongs which he hooked into her nostrils, pulling them up. It wasn't painful, but it kept her head angled back.
Liza heard a pop as the Headmaster opened another bottle of champagne. She whimpered softly. "Shh... " He stroked her hair gently. "Don't worry, this one's not for your ass. I thought you might like your first taste of champagne."
He poured some through the ring gag. filling her mouth, forcing her to swallow several times before he stopped. She enjoyed the taste, though it was strong, and she was still drunk and drugged from the restaurant. He repeated this twice more before he put the bottle down and returned to her.
She watched as he lifted his cock, pointing it at her. A stream of hot piss arced into her throat. She swallowed as quickly as she could, but it was too much, too fast. It splashed across her face, dripping into her pulled-open nostrils, ears, and hair.
His semi-hard cock eased through the ring into her mouth. He let her suck it for a moment before he began to gently thrust. As his cock thickened, he slowly fucked her throat, enjoying the sensation as her tongue massaged his shaft.
"That's right, suck my cock. I want you to take it all... take it down your throat." With each thrust his cock seemed to get longer, thicker, and harder. Somehow she managed not to gag as he pushed into her throat, his balls slapping into her face with each stroke.
She began to swing gently back and forth in the harness. He grabbed her head to hold her still and forced his hard cock in until her lips were pressed against him and her nose was buried between his balls. He held her there for a while, savoring the sensation of her throat around his cock.
At last, he pulled out and let her breathe. His cock was dripping wet with her saliva. She watched thick strands stretch from her mouth to his member before splitting and dripping down her face.
He poured a splash of cold champagne over her breasts raising goosebumps on her smooth young skin. Then his lips were on her, sucking her breast into his warm mouth while his tongue expertly played with her nipple. His hand grabbed her breast, squeezing, forcing her stiffening nipple deeper into his mouth. She felt a twinge of pain as he attached a clamp, and then pulled it to ensure it was snug. He repeated the process with her other nipple.
Then he grabbed her and spun her around. The wall she now faced was covered in a plethora of panties - dozens of pairs, all different styles and colors. She thought she saw a few of her own. Then another splash of champagne drenched her bare pussy, distracting her.
The contrast of the chilled liquid followed by his warm mouth caused her to moan in pleasure. His tongue massaged her clit, and probed into her tight cunt. A third clamp was attached just behind her clit, causing it to protrude, exposing it even more to his tongue.
The Headmaster adjusted the ropes, spreading her legs. She felt the cork in her ass twist as he removed it. She could feel some liquid draining out, but her body had absorbed most of it. Without warning he penetrated her, plunging deep into her cunt. She gasped but could do little else.
After just a few thrusts, he pulled out, and she felt his cock pushing against her asshole. It opened easily for him - it was probably still gaping from the cork, she realized. He fucked her hard; his hips smacking into her with each thrust, causing her to swing away from him, and then back onto him - her momentum impaling herself on his cock.
She lost track of time, but eventually, he spun her around again and pushed his slick cock into her mouth. She tried to block him with her tongue, but the ring made it difficult, and he easily forced his way past. He thrust deep into her, gagging her as his balls slapped into her face. Over and over he plunged into her throat, only pausing when he was deep inside her.
He fucked her face for a few minutes, then spun her around and pulled her ass back onto his cock. She lost count, but it seemed he fucked her ass and then her mouth at least a dozen times before she felt his cock throb as he ejaculated deep into her throat. He pulled out quickly, letting her watch as his next spurts coated her face with his warm cum.
But the Headmaster wasn't done. He unhooked her nose and unfastened the ring gag. He let her relax her jaw for a moment before ordering her to open it again. Then he rubbed his damp balls across her face, pushing his cum into her open mouth. It was slow, messy, and not very effective - mostly just coating his hairy balls. Perhaps that was his intent she thought as he lowered his balls into her mouth. She sucked and licked the mixture of sweat and cum.
When he was satisfied, he turned around and straddled her head, resting his wet balls on her face, and his asshole over her mouth. She knew what he expected, and almost without thinking she found herself opening her mouth and licking, What drug had he given her? She liked to please, but this was different. It was like she didn't even have a choice she thought, as her tongue pushed into his asshole.
He enjoyed the rimjob for a few minutes before easing off her face.
"Why..." she managed to ask.
He knew what she meant. "Why did I drug you?" She nodded.
"I need you to be completely compliant tonight. I have some very special guests coming over soon, and you will be the entertainment." She was stunned. He had never shared her before; she had no idea what to expect.
"In fact, they should be arriving any minute. Let's go back upstairs." He activated the winch, and lowered her to the ground, then unfastened the cuffs and helped her to her feet. She was still feeling the effects of the drug.
He blindfolded her while he explained what was going to happen. She was to fully cooperate with the visitors, doing whatever they asked. She didn't have to wait long; the doorbell rang before she had a chance to ask any questions.
"Wait here. Don't speak unless they ask you a question. And don't try to remove the blindfold. Understood?" He didn't wait for an answer.
She waited quietly as he greeted his guests and escorted them into the room.
"Very nice," said a woman's voice. "She's a first-year?"
"Yes. Not a virgin, but quite unspoiled, I assure you," the Headmaster responded.
The woman addressed her. "Get on your hands and knees, girl. And spread your cheeks for me."
Liza hesitated. Even drugged, she wasn't feeling very cooperative. SMACK! Someone - she had no idea who - struck her hard on her bottom. It felt like a thick stick. She cried out, as much in surprise as in pain. She had been spanked many times since arriving at Royal Oaks, but never so hard. Someone grabbed her hair and forced her roughly to her knees.
The woman spoke again, but this time not to her. "Be a dear and lube my arms, darling."
Liza felt a hand on her pussy spreading her lips. Two fingers pushed into her, thrusting in and out, hard and fast. Just as she began to adjust to the feeling, a third and then a fourth finger was added, stretching her young pussy open. She whimpered.
"Relax, girl. I'm just getting started," the woman told her. Liza felt the woman's entire hand pushing into her... past the knuckles... even deeper... until she could feel the woman's thumb against her clit. But the woman didn't caress her, she wasn't trying to provide pleasure. Her hand twisted, stretching and opening Liza even more.
Then even her thumb worked its way in. She slowly forced her entire hand deeper. Liza struggled to breathe. She could feel the bones of the woman's wrist as they penetrated through her tight hole, but the woman didn't stop there. She began thrusting, pushing deeper each time; long, slow thrusts until her entire forearm was inside the young student.
After a few minutes, the pain subsided, dulled perhaps by the drug. The feeling became almost pleasurable but more intense than she could handle. And then she felt two fingers push into her asshole. Liza cried out, realizing now why the woman had wanted both of her arms lubricated. The woman just laughed and added a third finger, and then a fourth. The girl's rectum was far tighter than her cunt. It took a lot more thrusting and twisting, but eventually, her whole hand was inside Liza's ass.
Liza collapsed to the floor, gasping for breath. But she was pulled back up by her hair, and a soft cock was pushed into her mouth. It wasn't the Headmaster's; she was quite familiar with his by now. This one was thick, with bushy hair, but thankfully fairly short; she could still breathe even when her lips were pressed against him.
After forcing himself into her, he stopped moving, but he did hold her head so that she was unable to pull away. He expected her to do the work. So she sucked and tried to massage him with her tongue, but there wasn't much room in her mouth.
Liza was unable to focus. The woman behind her was alternating her thrusts, pulling one arm back while the other pushed in. But she never pulled completely out. She kept her hands balled up as fists; they were too large to pass through the girl's tight holes.
At one point, she pushed both arms in at the same time, almost to the elbow. Liza had never been so stuffed. The pressure caused her to release a stream of pee; the warm liquid ran down her leg. But the woman didn't stop; if anything she pushed deeper.
Click. Click. Liza heard the soft sound of a camera shutter and sensed the glow of the flash even through her blindfold. Someone was taking pictures.
The man didn't last long; maybe two minutes before she felt his warm cum oozing out into her mouth. The man let her swallow and then pulled out. He still held her head with both hands as he smeared his wet cock across her face. Click.
At last, the woman pulled out both arms. "Turn around," she ordered. Liza complied as quickly as her drugged muscles would allow, almost against her own will. "Lick me clean." Reluctantly, she began licking the woman's slick arms, cleaning her like a cat.
SMACK! She cried out as another hard stroke marked her bottom. "That's for not thanking me for my cum," an older man's voice said. It was the first time she had heard his voice.
"Thank you, sir," she managed.
He didn't respond, but she felt something hard push into her cunt. It wasn't thick - especially compared to the woman's arms - but the end that penetrated her felt hard and cold - probably metal, she thought. He thrust into her a few times before switching to her ass, and then back into her cunt.
"Do you like my cane better now?" he asked. Liza tried to ignore him and instead concentrated on licking the woman's arm. That was a mistake she realized, as the cane pulled out. SMACK! SMACK! Two more hard strikes, one on each cheek. She could feel the welts forming.
"Not very polite, is she?" the older man observed. "She needs more training."
"She's always had a rebellious streak, but she does learn quickly," the Headmaster replied.
"Thank you for fucking me with your cane, sir," Liza offered. "... and for letting me drink your cum," she added.
The man just grunted, but his hand grabbed her hair and forced her to spin around again. His other hand grabbed her breast, squeezing hard as he pulled her down between his legs. She opened her mouth to take his cock once more, but that was not what he wanted. She felt his hairy ball sack pushing into her mouth; she opened wider to take both in at once.
"She is quite lovely," the woman interjected, stroking the red streaks on her ass. "But I'd prefer a virgin next time," she added, pinching the welts hard.
"I've been thinking about that," the Headmaster smiled. "Most of the students aren't... suitable. But there is one instructor you might like."
- The Headmaster's collection in the basement included a variety of BDSM items, such as whips, riding crops, and clamps.
- Liza was surprised to find cnc machines in the Headmaster's basement, along with other unusual sex toys.
- The Headmaster's special plans for Liza included bondage, rimming, and fisting, which she found both terrifying and intriguing.
- Liza's bondage session included the use of rimming clamps, designed to enhance the experience of anal play.
- Liza's experience that night in the Headmaster's basement was a mix of pain, pleasure, and submission, all while she remained under the influence of the drug he had given her.