Anal Academy Pt. 03

Holly did not know what to think. This whole weekend, this whole process was supposed to be for Frank. How could this be in service to him and their marriage if Holly let another man fuck her in the ass. She leaned forward and buried her face in the sheets but left her ass high and in position.

"That's a good girl," Ms. Witherspoon chimed in. "Just settle in and relax. I know from experience, Mr. Petat is a talented and gentle lover. You will be forever changed after today."

Holly could feel his weight on the mattress as he moved closer to mount her. The mattress springs squeaked beneath his heft. She heard him panting and felt his hot breath on her back as he leaned in closer. For such a "talented lover" he sure seemed to get out of breath quick from the work of climbing into bed.

"We'll start slow," he said. "Just a little pressure to begin." Holly felt him press the stiff and slick head of his cock against her backdoor. A rush of sensations and feelings hit her body in that moment. She had indeed been trained well. Holly ached to be penetrated. Her body responded hungrily to the promise of something requesting access to her ass.

But she also thought of Frank. She wanted him to be the first to experience her newfound desires. The more she thought about it, she did not want it. She needed it. She would accept no substitutes. Holly lurched forward and laid her front entirely down on the bed, removing the high and open access to her cavities. She clenched her butt cheeks to make the point crystal clear.

"No," she said. "I can't do this. I can't do it to Frank. I'm sorry, Mr. Petat, I just can't."

She felt his body leave the mattress and heard the sounds of him dressing. "I understand, my dear," he replied softly. Holly looked up and saw the disapproving face of Ms. Witherspoon, leering mere inches from her own.

"I accept your decision, though I do not endorse it," she said. "I had a feeling something like this might happen, so I came prepared with a plan B." She looked up at Petat. "Robert, you may leave now." She shoed him out with a few harsh gestures of the wrist. She seemed to be disappointed he had not just forced his way in.

"Lie back, Holly. Rest your head on the pillows and get comfortable while I set up." Holly did as she was told. She felt as though she had disappointed Ms. Witherspoon. From this point on she would do anything that she was told. She would not disappoint again.

Holly reclined and watched in growing surprise as Ms. Witherspoon undressed. She unstrapped her heels and laid them to rest on the chair. She unbuttoned her blouse and neatly folded it atop the heels. She slid out of her pencil skirt and added it to the meticulous pile. Holly marveled at the tightness of her body, the limbs lithe and athletic despite the bookish exterior.

"The garment wears better when nothing is beneath it. It may seem unnecessary to strip down to the buff, but I find it more comfortable this way." This was meant as a complete explanation, but Holly found herself as befuddled as when Ms. Witherspoon had first begun her undressing. She continued, removing her bra and panties, until she was every bit as exposed as Holly. And yet there was not a hint of vulnerability anywhere to be found. Ms. Witherspoon appeared as comfortable and in command in the nude as she was directing her masters to carry out the Academy's fuckery.

She opened a small wooden chest at the foot of the bed. She withdrew a bundle of leather straps, their ultimate form and function unclear to Holly, and began wrapping them around herself. She bent over, stepping into something, and disappeared from Holly's view. When she stood again, Ms. Witherspoon was tightening a belt strap, and Holly could clearly see her wearing the structure of a harness around her hips.

"In this session you must fuck a person. You must be made ready for your man. You cannot fuck a wall or a machine or a vibrator. It must be someone." She bent down again out of Holly's view. "Now you refuse for that person to be a man with a real cock, and I understand that decision. I respect it a little, though I do not like it. So, your someone must be me." She stood, continuing to adjust something on the harness near to the place between her legs. "And seeing as how I don't have a cock, we will have to make do with this."

Ms. Witherspoon moved her hands away from her crotch and held them aloft, as if she had just completed a magic trick. In their wake, a large thick black strap-on dildo stood affixed to Ms. Witherspoon's harness. She bent over one last time to pick up a lanyard with a whistle on it, placing it around her neck. She turned to face Holly, and the strap-on turned with her, leering at Holly as it bobbed up and down slightly in response to Ms. Witherspoon's movements.

Ms. Witherspoon advanced on the bed with grace of a cat, sneaking her way between Holly's legs before she'd realized what was happening.

"You will not be restrained. You must choose to accept me inside you, and only through that choice can your training be complete. Now, let's get the lube out." Rather than reaching for a nearby bottle, Ms. Witherspoon put the whistle to her mouth and blew. Holly felt her entire body change in response. The Pavlovian reaction had taken over. She relaxed, she was made ready, and she could feel her pussy turn on like a faucet.

Ms. Witherspoon also noted the immediate response ("My, my, you have made a pool already"). She reached inside of Holly with two fingers and gleefully withdrew them thickly coated. Drops of moisture fell from the fingers and landed on Holly's milky thighs. Ms. Witherspoon reached again inside Holly's pussy and mined for more natural lubrication, this time taking her hand and using it to coat the strap-on dildo, which now glistened with anticipation. Ms. Witherspoon held the moistened shaft in one hand and advanced upon Holly's pussy, driving it inside one inch at a time.

Holly gasped and thought to herself: as much as she had been trained to find pleasure in anal stimulation, none of it compared to the feel of something nice and thick splitting her cunt down the middle.

"Yes. Stay there. Right there." She moaned. Ms. Witherspoon obliged her for a moment, guiding the dildo deeper before withdrawing and thrusting a few more times. A malevolent smile creased her lips as she pulled it out for good.

"I'm glad you are having a nice time, but that is not our purpose here. We know you are capable of getting well-fucked in your pussy. What we need to complete is your anal training, and this is the final phase." The lubricated dildo now found its way to the sensitive puckered opening of Holly's anus. Ms. Witherspoon drove forward once more, this time more gradually. She gave the whistle another brief blow, which sent more lubrication cascading from Holly's open pussy and coating the base of the dildo at it advanced.

Holly moaned, no less in heaven with the dildo in her ass than when it greeted her pussy.

"That's it. That's it," Ms. Witherspoon intoned, her eyes fixed upon the dildo's length slowly disappearing within Holly.

"Yes, you're right," Holly whimpered. "That is it. I welcome it. I invite you into my ass. I am free of mind and free of body. I am not restrained. You have not forced me, and I invite you in. I ask for you to give me anal pleasure. I beg for you to complete my training." Holly put her arms outstretched to either side and closed her eyes. She rolled her hips back and brought her knees to her chest. She made her body echo the intent of her words. She opened herself fully to being fucked in the ass by Ms. Witherspoon's enormous strap-on.

Though Holly could not see it through closed lids, Ms. Witherspoon's smile spread wider, and she began thrusting. She brought the dildo out and pushed it in. She watched Holly's open ass give way; she noted the tight grip of flesh on the black object within. They settled into a rhythm, and Holly welcomed the slow methodical fucking she received.

Holly's pleasant monotony was interrupted by a sharp pang of new stimulation. She opened her eyes to see Ms. Witherspoon leaning over her, braced on one arm. Her other arm was snaked between her legs, touching Holly's pussy. Ms. Witherspoon traced her fingers around the moistened lips before stroking Holly's hooded clit. Holly gasped and moaned.

Ms. Witherspoon straightened up and removed her hand from Holly. She looked Holly in the eyes and said, "Just wanted to get your attention." She grasped Holly around the hips to hold her stead and began thrusting harder, faster.

"Oh, trust me, you have my full attention."

Ms. Witherspoon traced her fingers down Holly's thighs and up her own abdomen. She encircled her own breasts before pinching her nipples and holding pressure. She squealed as she blurred the line between her own pain and pleasure.

Ms. Witherspoon turned her attention again to Holly. They locked eyes. "This isn't a long, drawn-out session. You have accepted anal pleasure. Your training is complete. Now all I want from you is for you to cum with me. Do you think you can do that?"

"Yes."

"Good." Without breaking the stride of her thrusts, Ms. Witherspoon reached behind Holly's head and pulled out a small throw pillow. She placed it between her own legs like a seat, all the while fucking Holly's ass with the froth of her own wet pussy. Then she reached behind herself on the bed and brought out a vibrator she had set out but hidden. The purpose of the pillow became clear as Ms. Witherspoon wedged the vibrator in place between the pillow and her own thrusting groin, nestling it right up against her pussy.

Holly heard the vibrator switch on and saw an immediate change come over Ms. Witherspoon's face. Sheer ecstasy dripped from her pours. The pace of her thrusting increased, and it brought her to new heights. She was grinding against the vibrator, and the faster she moved her hips, the more she felt the vibrator and the harder she fucked Holly's ass.

Holly was amazed by how much pleasure she felt. There was no vibrator for her, no "double trouble," no stimulation of her typical pleasure spots. Even with her pussy untouched, she could feel an orgasm building. It felt different, deeper within her. She knew that if she could keep Ms. Witherspoon going a bit longer, she would leave with carnal knowledge of an anal orgasm.

Ms. Witherspoon's fucking became shallow and rapid, almost rabid and uncoordinated. She too descended into animalistic lust. With her left hand she returned to tweaking her nipples, and she laid her right hand on Holly's chest to brace herself. Her hips were a blur, grinding as hard and fast as she could. Both women locked eyes again, and their panting breathing seemed to match up in time.

"Are you ready?"

"I want it."

"Are you sure?"

"Give it to me. Blow that fucking whistle. Make me pop on your command. I'm a good girl. I've been trained well. Make me obey."

Ms. Witherspoon brought the whistle to her lips. She left it there, hesitating. She watched the desperation play out on Holly's face. She held the power, and she held onto this moment for as long as she could tolerate. But eventually Ms. Witherspoon's need for release got the best of her. She too had been conditioned to climax at the sound of the whistle. She blew its shrill blast loud and clear in the room, and the eyes of both women rolled back in their heads as their bodies were overwhelmed by the force of pleasure between them.

Witherspoon screamed and cursed angrily. She emitted the vilest of passages as she rode out her release. Holly was again returned to a state of jelly, the force of her climax too overwhelming to tense up or make a sound. She passively rode the wave of her orgasm, and it propelled her to a new horizon of pleasure.

While Holly remained sprawled, panting, reveling, Ms. Witherspoon returned to her work. She retracted the strap-on, shut off the vibrator, stood at the food of the bed, and had removed the harness and fully dressed before Holly even opened her eyes.

"You will do well. Frank will be pleased with your progress; I am sure. This is your room for the night. Please make yourself comfortable and someone will be in in the morning to retrieve you."

Ms. Witherspoon turned and knocked on the door. It was opened from the outside, and she walked out without another word.