Squeezed, Pt. 02

"I'm excited for Sam to fuck my arse with his big cock." She clenched her dress tight against her body, and the words rushed out of her, a little too loud.

"His big what cock?"

"His... his big, beautiful cock."

"His big, beautiful, young cock. Ask him, go on."

Cleo managed to drag her thirsty stare upwards, away from the sight of Sam's cock being stroked with both hands, to his tense expression.

"Please Sam will you fuck my... my arse, with... with..."

"Big..." Mary prompted.

"With your big beautiful young cock." The words once again came out in an uninterrupted stream.

Mary smiled with excitement, squeezing his cock a little tighter and bringing a soft moan from his lips. "Well, Sam, you can hardly say no when she's asking so nicely, can you?" She giggled for a moment before turning back to Cleo. "Dress off, then, and bend over the desk."

The Dean obliged, pulling the pillar of white linen up to reveal a gently tanned, lived-in, yet nubile body: an elegant cinch to her waist, ribs and pelvis outlined against her skin, breasts slight enough to defy her years, but partially hidden under her long silver mane. Sam trained his stare on her, looking her up and down as Mary pumped his cock.

Cleo turned, laying her upper body down flat over her desk, her gaunt posterior pointed straight at Sam, anus and vulva pulling open at the spread of her legs. She looked back over her shoulder at him. Sam was at least accustomed to nudity, to spread and stretched genitalia on campus, by now. But the fresh impropriety, and her almost instant transformation from administrator to expectant sexual partner, were still enough to turn his stomach.

Mary took her left hand off his cock and moved it to the large of his back, pushing him forward, silently urging him to stand. With her right, she pulled his erection, guiding him towards the desk. A gentle, but purposeful instruction, with which he complied, as he always did.

"Are you ready, Sam?" A whisper. He gave a quiet nod.

"Alright, then... you've never done this before. So even if the plug has done its job, she's going to need you take it slow, so she can get used to you. Understand?"

"Yeah..." Cleo was smiling back at him, her eyes alight.

Sam stood above Cleo's posterior, his arms at his sides, expecting Mary to guide him forward. He possessed no inclination to move of his own volition, and would need to cede control to her in order to make his way through this act.

Instead, Mary leaned close to the soft buttocks that waited patiently at the edge of the desk, and let a thick gobbet of saliva fall from her lips. Another. A third; each landing wetly on, or just above, Cleo's anus, coating it.

"We'll need to get it wet, Sam" she said, wiping her mouth. "You try."

"Try...?"

"Spit." Cleo gave an approving, soft moan at the instruction.

Sam leaned down, as Mary had, and gathered spit in his mouth, opening it to drop it close to the already soaking hole. Cleo shuffled her hips left and right, as if to invite more; this close, he could see her flesh with grim clarity, her holes pulled open, soaked in drool.

Mary reached in, and slid two fingers inside Cleo's anus, slowly pushing them in and out, working the layer of saliva inside her. Cleo moaned again, her back tensing up, her hips lifting off the desk a little at the penetration.

"We need to make sure she's ready, okay?" Mary spoke very softly, in the attentive, clarifying way that she did. "She seems quite relaxed..." a third finger. Cleo let out a louder moan, and the Counsellor, with a movement driving from her shoulder down to her wrist, fucked her slowly, forcing her fingers a little way apart to spread the Dean wider still.

Cleo was moaning, in a distinctly pleading tone. Certainly one of pleasure.

"It's going to hurt her when you fuck her, Sam. I can't come close with just my fingers. You'll have to be ready for it. Just take it slow."

"I want it to hurt" moaned Cleo, softly, but with a tense edge to her words. "I've been thinking about it all day, Sam. How you're going to stretch my arse. Please... please."

Mary rested her cheek on Cleo's right buttock, and smiled broadly up at Sam, three fingers still pushing in and out of the glistening orifice.

"Sam, are you ready to give her what she wants?"

Sam's cock jumped happily, wagging his tail against his own wishes. He shut his eyes.

"That looked like a yes, to me." She withdrew her fingers, and he felt the same hand grip his cock again -- now repulsively wet -- and guide it forward, as he leaned his hips outward to comply. He kept his eyes shut as he felt the tip make contact with the opening, the hand on his lower back urging him to push forward.

He felt her give way to him, and soft, warm flesh surrounded the head of his cock, hugging it tight.

"Fuck...!" The cry was from the opposite side of the desk, where Cleo had lifted her head, her shoulders and back tensing from the unexpected strain. Sam opened his eyes and looked down to see her anus strained around him, the head of his cock disappearing inside her. Her right leg kicked off the floor involuntarily for a moment before she steadied herself. "Fuck, fuck, fuck... Sam..."

"She can take more. Keep going." Behind her enormous glasses, Mary's eyes were wide with excitement. Sam leaned in a little more as she fed his cock further inside the prostrate Dean.

"Ugghhhh." Cleo gritted her teeth, gripping the edges of the desk next to her shoulders, groaning miserably, gutturally. "Sam, you little bastard... fuck..."

"You asked me for this, Cleo. You were very insistent. Remember?"

"Ngghh... yes, Mary..." the Dean's voice broke and trembled as inch after inch of Sam's cock gradually snaked inside her. "Th... thank you..."

"Say thank you to Sam, too. He's doing us both a big favour, here." Another few inches. It was almost completely sheathed.

"Nnnggh. Thank... you... Sam... fuck..." His hips met her buttocks. Sam stared, dumbfounded, at the sight of the Dean's anus, stretched horribly wide around the very base of his cock. He looked further up. All over her body, muscles were tensing and relaxing, reflexes of the elder woman's need to accustom herself to the body part lodged inside her.

"Fuck, it's big." She breathed. "It's... it's fucking big."

"Yes, it is" Mary sang, with obvious pride. "It's the best."

"Alright, Sam" she added, "you know what to do now. Remember, go slowly." She reached down and took him by the wrists, placing his hands on the small of her back. Compliant, he gripped her waist. He did his best to focus, to will his body into action. The warmth and impossible tightness enveloping his cock elicited an eager tension from his perineum, making him not just erect but achingly tense inside her. His buttocks clenched. His entire body wanted to fuck.

He eased back, pulling out a few inches, as slowly as he could. Cleo gave out more agonised, yet hauntingly gleeful, cries; her shoulders first hunching around her ears, then falling again. Her torso remained flat against the desk, but Sam would remember the sight of her taut back muscles flaring and quivering for years after.

He sank forward again, and filled her once more up to the base. Her voice peaked, shrill, and then disappeared, the hoarse sound of her breath lingering on.

He repeated the movement a few more times, drawing out, and then in, appalled at the satisfaction he felt from her stretched-out hole strangulating his cock. He felt the muscle contractions throbbing down past his groin, his heart thumping, his body happy, himself repulsed. Each forceful, snaking thrust inspired more groans from his recipient. More convulsions. He himself moaned, before he even realised he was doing it. He gripped tighter, thrusted a little harder. Her distorted hole rippled over his slimy, veiny surface, concealing and then revealing. Through her teeth, she growled expletives, and his name. Background noise.

Mary had stood up, and she made her way around to the other side of the desk. Hands on her knees, she leaned down, and Cleo craned her neck to meet her with several thick, wet kisses. Rearing up once more, she pulled her dress up and off. Her underwear fell to the floor next, and she took a seat in the leather-padded chair that sat behind the desk. She lifted a leg over one arm, displaying her already wet pussy a short distance from Cleo's face, and began to stroke, the two women staring into each other's eyes with knowing euphoria as Sam performed his service.

He took note of the physical disparity between them: Cleo tall and tanned, her skin predictably looser thanks to her age; Mary short, softer, pale, with discernible curves. Cleo's obedience was unmistakable: Mary whispered, instructive, while the older woman on the desk gave compliant, eager responses through a chorus of grunts and groans.

"Sam?"

"...yes?" He stopped moving.

"Cleo says you can fuck her properly now."

"Properly?"

"Hard. Would you mind?"

The truth was, it was still difficult to move. There wasn't yet a lot of give. Her anus still gripped him tight, and he needed to make a notable effort just to move slowly. He engaged his haunches and lower back more, pulling out with pronounced haste, before reversing the movement, swinging his hips forwards into hers.

She reacted as he expected her to: more groans, further convulsions. He pressed on, swinging his hips back and forth to feed his cock into her with greater force. The groans turned into screams, squeals. She stamped her feet in turn, occasionally lifting both off the floor and kicking wildly. Trying to shake it out, he thought. The intensity of it. She was overwhelmed.

"That's it, Sam. Don't be shy. She loves it." Mary was rubbing her clit with her fingers flat, frigging herself hard, her stare never leaving Cleo's eyes. Sam could see from his vantage point that she was fixated on the expression of agony that he was fucking into her senior. A projection, perhaps, of the same agony she took into herself when she coerced his cock into her, time after time. A projection of the objectification she subjected him to, that she was able to demonstrate and share his excess. That it was hers to give away.

"Nnnnggghhhhhyes yes yes Sam I love it. I do love it..." Cleo was slurring her words as he pounded her backside. Mary was beginning to moan, too, writhing and fucking herself with her fingers now, the ball of her hand kneading her clit. He could make out the sweat sheen from here, her pale skin turning pink, her round glasses sliding down her face, as they always did when she sank deeper into the moment.

"Do you like the big cock I brought you?" Sam, thrusting with all his might, winced.

"Yes, Mary. Thank you thank you thank--" breathy, and slurred.

Of his own volition, Sam lifted a knee up on the wood surface, stuffing himself deeper into her arse. He brought the other knee up as well, so that he was kneeling on the edge of the desk, straddling her hips and steadying himself with his hands. He felt out of control of his own body now, hunched and desperate to fuck with as much energy as was expected of him. Cleo's moans peaked at a silent, hoarse wheeze, unable to simultaneously vocalise and absorb the hammering her anus was taking from his gargantuan cock. But she had relaxed more, too -- he was able to move more freely, to throw his cock inside her with more force, less effort. Faster and faster, he drove it into her, grunting, sweat pouring down his brow and back.

"Sam don't stop don't stop--" Mary's voice, too, was peaking, and he glanced up. Her chin was dug into her chest, her shoulders and back hunched upright in the tall wooden seat. She screwed her eyes shut for a moment, then opened them, eyelashes quivering, mouth contorted in a silent scream that mirrored Cleo's. One leg steadying herself against the floor, the other jerking and trembling. Her hips squirmed, eased up off her seat, and landed again, and from there her whole body shook. Her tension lapsed enough for a series of high-pitched, breathy moans to escape.

Sam hadn't seen a woman cum before. It hadn't been part of his remit, with Mary -- she was concerned only with his size. The sight of her in a state of sheer, personal pleasure was unexpected and unknown to him, and he felt the energy of it fuel his own incessant thrusting.

He and Cleo were moaning together, now. The physical constraints overcome, her body relaxed and pliant beneath him, the two of them synchronised in his unconstrained drilling down of her hole.

Mary stood, shakily, but nothing near the unstable gait that usually followed their sessions. She came back around and stood next to Sam, her left hand sliding under his shirt and stroking the sweat of his back.

"Are you going to cum inside her?" His hips piling forcefully into the screaming body beneath him, he gave a concentrated nod.

"Good boy."

It was a sensation fairly alien to him, and one that caught him unaware. The urgent energy pushing him onward from behind his balls was suddenly accompanied by a deep, and not un-painful, fullness. There was movement, too.

His brain caught up with the escalation: the Counsellor had, without warning, slid her middle finger all the way inside him.

He would wonder for weeks whether it was the finger, or the total degradation of the remark that accompanied it, that pushed him to climax. He felt himself throbbing around the finger, as if his body was fighting for space, the muscular contractions at his perineum seeming stronger and agonisingly more sensitive. They thrummed and rippled. It was the most personal and vulnerable orgasm he'd ever felt; he couldn't even pinpoint the moment that his twitching cock actually began releasing string after string of hot cum deep inside the shrieking Dean's arse. He was hunched over her, clinging to her shoulders. She reached up, and her hands gripped his. Her screams whooping, deafeningly loud, but impossible to interpret as anything other than satisfied, grateful happiness.

When the tremors died, he withdrew. He didn't even dare to look at the mess he'd made; Cleo lay there on the desk, in a haze of her own aches and pleasures, still squirming with the joy of having been fucked so thoroughly and completely. He staggered back, grabbing at his shorts, pulling them back up to conceal his sore, softening cock.

His head hung, sulking, as if the deed had literally weighed it down. With his service fulfilled, Sam felt guilt and shame wash into him.

He turned to Mary, still panting, mouth open, his face flushed pink. "Uh..."

She was still completely nude, standing cheerfully next to the spent and exhausted woman draped over the desk. "Well done, Sam." Her classic prim smile. "I think you made her really happy."

He looked over at Cleo. "Are you okay?" he panted. A hypnotic "mm-hmm" came back. He looked back at Mary.

"So..."

"You don't want to hang around?"

He desperately wanted to be gone. He shook his head, his hair flicking a mist of sweat in her direction.

"Alright, that's fine, Sam. I'll take it from here."

"The... paperwork."

"Yeah, I'll handle that. You head off. Enjoy your evening."

He didn't hesitate. He made a beeline for the door, and shut it behind him without a further word.

As he emerged from the second door to the outside, he could have sworn he heard a series of loud noises from behind him -- their voices, and something else. He didn't dare to check. He crossed the threshold to the outside and, as he had learned to do, began stuffing the experience into the shameful little box in the back of his mind.

He reached the gate, walking at pace.

"Sam!"

Ellie had been standing just on the other side. He'd been walking with such determination that he almost missed her. He stopped, and stared, conscious of the scents he must be carrying with him.

"I waited for you. Why are you walking so fast? You've gotten so sweaty." She smiled, and mopped his brow with her hand. It came away sleek, wet. "Wow."

"Yeah, I... the meeting was annoying. Wanted to get home. Why are you still here?"

She raised her eyebrows in slight indignation. "I was waiting for you, Sam. I thought we shouldn't leave things as we did."

Drenched in sweat, he looked down at her. Small, gentle. Skinny jeans. Light blazer hanging from her shoulders just so.

"Yeah... I didn't want to do that either."

"Okay, well... while I was waiting, I thought about it, Sam. I don't want to put pressure on you. We can be more physical when you feel ready."

"Oh. Ellie... thank you." It was real gratitude. He thought about the Quid Pro Quo. Whether it would really stick. If it did, he might be able to move on, to truly give his attention to this relationship. "That might be quite soon, actually. We'll see. Thank for you being so understanding."

"Well, great." She smiled, and leaned up to kiss him softly on his lips. He kissed back, and realised that he was happy to. Mary had never kissed him. Never even tried to. It was the one piece of his sexuality he felt still belonged to him. That he could share with her. He withdrew, and a faint, hopeful smile spread over his face. Another thought occurred: that he had only, technically, managed to end his scheduled sessions with Mary. His smile dropped just a little. Choosing to forget, at least for today, he leaned down for another kiss.