Chapter 5: The Lesson in Failure

The week leading up to the second Saturday was fraught with a new, sharper tension. The knowledge of the scoreboard, now a very real and threatening entity, transformed the pact from a daring adventure into a high-stakes competition. For the five women, the upcoming encounters were no longer just about pleasure or teaching; they were auditions for safety, each woman desperate to avoid the dreaded consequence.

Linda had transformed the humid pool house into a minimalist studio for oral instruction. Her partner was Anjali’s son, Ben, a young man whose serious demeanor she found intriguing. The first session’s score of 8 gnawed at her perfectionist nature; tonight, she would execute flawlessly.

Ben entered, his posture stiff. “Linda.”

“Ben,” she acknowledged crisply. “The lesson is oral, with the focus on you. The objective is to demonstrate techniques for maximum male pleasure. Lie down.”

She undressed him with efficient, clinical hands, folding his clothes neatly. His erection, when revealed, was respectable. Linda didn’t linger. She knelt between his legs and began her work. Her approach was systematic, almost architectural. She used her tongue like a precise instrument—long, flat strokes along the shaft, tight circles around the head, deep, rhythmic suction. She paid close attention to his breathing, the twitches in his thighs, adjusting her technique based on his involuntary feedback.

“The key is variation,” she explained, her voice calm even as her mouth was busy. “Monotony leads to desensitization.” She introduced her hands, cupping and gently massaging his balls while she worked, creating a symphony of sensation. Ben, who had approached this with analytical detachment, found his composure shattered. His breath became ragged gasps, his hips lifting off the futon.

When he was on the very edge, Linda pulled back. “Control,” she murmured, softly blowing on the wet skin. “Anticipation heightens the climax.” She continued this edging technique several times until he was a trembling, begging mess. Only then did she grant him a release so powerful it left him convulsing, his cry echoing in the small space. He flooded her mouth as the first jets hit the back of her throat and filled the hollows of her cheeks. With a satisfying gulp, she swallowed his young seed. She proceeded to clean him up with her tongue and ensured there were no remnants left to stain his shorts. As he recovered, she noted with satisfaction the swift return of his erection, likely caused by her slow and nurturing cock kisses. The second round was quicker, more primal, a reaffirmation of her mastery. She ended the session feeling confident. This was a nine, at least.

Carol, still stung by Chloe’s perfect ten, was a woman possessed. Her partner was Maria’s son, Mark, and her lesson was oral with a focus on her. This was her domain. She would be the center of attention, and she would wring every drop of pleasure from it.

Mark entered the office with his usual boisterous energy, which Carol immediately subdued with a commanding gaze. “On the desk. Now,” she ordered, pointing to the large oak surface.

She didn’t wait for him to get fully comfortable before she was on him, her mouth hungry and demanding. But this wasn’t about his pleasure. She guided his head between her legs with firm hands, teaching him through sharp, explicit instructions. “Slower. Softer. Use the flat of your tongue, not just the tip.” When he did something right, she rewarded him with a guttural moan. When he failed, she corrected him instantly.

It was a brutal, exhilarating tutorial for Mark. He was learning, but the lesson was entirely about Carol’s orgasm. She rode his face with abandon, her hands tangled in his hair, her cries filling the room. She came once, violently, then demanded he continue, bringing herself to a second, shuddering peak. Only then did she slide off the desk, panting.

“Not bad,” she said, wiping her mouth. “You’re a quick study.” She left him there, hard and neglected, a tool that had served its purpose. She felt no need for a second round; her own satisfaction was complete. She had performed. Now, she would be waiting for her perfect score.

A strange tension filled the guest room. Chloe’s partner was Linda’s son, Jason, and the lesson was Missionary. She felt confident after her triumphant first week, but this pairing lacked the dark, taboo charge of being with Noah.

Jason entered, looking every bit the football star, a mix of confidence and nerves. “Chloe.”

“Jason,” she smiled, a warm, genuine smile. “I hope you are ready for some fun. The lesson tonight is Missionary. It’s about connection. About being face-to-face.” She approached him and began undressing him slowly, her touch gentle compared to Carol’s aggression. “It’s not just about getting off. It’s about being present with each other.”

She led him to the bed and lay back, pulling him on top of her. She guided him inside her, sighing as he filled her. “Now, look at me,” she whispered. As he began to move, she held his gaze, her hands roaming his back. She coached him softly. “Slow down ... feel that? ... now a little deeper ... yes, just like that.”

It was a loving, deeply intimate session. Chloe used her body to teach him the rhythms of lovemaking rather than just fucking. She wrapped her legs around him, pulling him closer, whispering encouragements. When he erupted into his condom, it was with a deep, satisfied groan, his head buried in her neck. They lay together for a moment, breathing as one.

The second round was more playful, with Chloe taking a more active role, flipping them over and riding him for a time before returning to missionary. It was a masterclass in affectionate, skilled sex. As Jason left, he looked dazed and utterly captivated. Chloe felt a warm glow of success. It had been wonderful, but a part of her missed the raw, boundary-breaking intensity of her first Saturday. This was a comfortable eight or nine. She craved another ten.

Anjali had prepared the master bedroom with her usual methodical care. The lesson was Cowgirl, a position of female control, and her partner was Leo. She approached it as a fascinating physiological and psychological study.

Leo entered, his smile and demeanor warming Anjali’s heart. “Anjali.”

“Leo,” she replied evenly. “Please, disrobe and lie on the bed.” She undressed with him, her movements unhurried. Her body was soft, real, a contrast to the taut perfection of some of the others. From out of nowhere, she produced a foil package of care. She tore the condom packet open and proceeded to efficiently roll it down his hard-as-steel cock.

She knelt over him but did not immediately lower herself. “The cowgirl position offers the woman maximum control over depth, angle, and pace,” she began, as if lecturing. “It allows her to target areas of internal pleasure with precision.” She guided his hands to her hips. “Your role is to follow, not lead. Feel the motion.”

Then, she sank onto him. Leo gasped at the sudden, complete envelopment. Anjali began to move, a slow, rolling, circular grind that was utterly foreign to his experience of frantic, linear thrusting. She was calibrating him like a fine instrument.

“Observe,” she said, her breathing steady. “This angle stimulates the anterior fornix. This ... the G-spot.” She shifted her weight minutely, and Leo saw stars. “Your feedback is important. What sensations are most pronounced?”

He could barely form words. “I ... uh ... the grinding ... it’s ... fuck...”