They held each other’s gaze for a moment. Then, without speaking, Jensen spun her to face the mirror and shoved her down over the horse. Anna exhaled as her belly hit the padded top.
He slapped her ass and Anna wiggled until she was firmly planted on the wide top piece, her toes braced on the floor. It felt odd and a little uncomfortable to have her arms behind her back in this position.
Jensen touched her shoulder. “Relax your arms, the binder will hold them in place. Good girl. Now spread your legs.”
Anna inched her toes out to the side, the plug shifting as she moved.
“Good girl,” he said again, and her pussy clenched at the words. She loved it when he called her that. Raising her head, she watched him in the mirror. The sight of him—all raw power and strength towering over her as she lay helpless and bound before him was thrilling.
“How does that pretty little ass feel?” He tugged on the plug.
“Good, Master.”
“Are you ready to take the next size?”
“Next size?” Anna squeaked.
“This one isn’t even as thick as a cock. Did you think this was it? Before we’re done this weekend, you’ll be taking a large plug up that pretty ass—a very large plug.”
Anna gasped and licked her lips. She let her head hang for a moment, her hair falling around her. The idea of being forced to take something larger than his cock—which was, until now, the largest thing that had even been up her ass—was darkly thrilling.
His thumb stroked the outer lips of her sex. She was wet with need and his finger slid smoothly over her skin. Pinching and tugging the lips of her pussy was enough to have her rocking against the horse, but not enough to give her the direct pleasure she was craving.
“Master, please.” The words burst from her lips.
“Please what?”
“Please, fuck me.”
“No.” As he spoke, he grabbed the plug and pulled. It took her by surprise and without thinking, she clenched down, trying to hold it in. The plug came free, forcing the tightened muscles of her ass to expand. Anna hissed and gasped at the pleasure-pain.
She heard the acrylic toy hit the floor the second before he started spanking her in earnest. His hand landed hard enough to have her screeching. “Master.”
He was silent as he continued to spank her. Anna’s toes left the floor as she thrashed under the painful swats. Each one spread fire over her ass, down to her pussy. The ultra-sensitive skin he’d abraded stung, throbbing like a bruise. Her nipples were rock hard, her pussy flooded with fresh moisture. The pain of the spanking made her clench her teeth even as she longed for him to escalate it, to move from his hand to a paddle, from a paddle to a whip.
As suddenly as it had begun, the spanking stopped. Over the sound of her own gasps, Anna was vaguely aware of Jensen’s labored breathing.
She slumped over the horse as he walked away. Her ass hurt, the stinging turned to throbbing. She raised her head, watching him return. The angle meant she couldn’t see his hands, and whatever it was he might be carrying. Planting a hand on the small of her back, he pressed something into her pussy.
Anna screamed in pleasure. It was as thick as his cock, but unlike his flesh, was cold. It didn’t go very deep, but that first moment of penetration was so intense that pleasure shot through her like lightening.
“Naughty girl, did you come?” Master Jensen twisted the thing inside her.
“No, Master. That just felt very, very good.” Anna sometimes wondered if these shocks of pleasure weren’t what other women called orgasms. She suspected that those who weren’t privileged to be used and played with by a Master didn’t know the soul-shattering pleasure that she called orgasm. Really it was a matter of semantics, and she certainly wasn’t going to admit that she sometimes had little mini-orgasms.
Maybe she wasn’t the most obedient submissive.
“Do you know what this is?” he asked, pulling the toy out only to thrust it back in.
“A dildo, Master?”
“No, my pretty Anna.” He held it up so she could see it.
A silver plug gleamed in the light. It was short and very thick, more closely resembling a mushroom than the long, slender plug he’d pulled out only moments before. He twisted it and she could see that the flared base was set with a large glittering hunk of quartz. The neck of this plug was almost as wide as the largest part of the last one.
“This is your medium plug,” he said. His smile was devilish—his lips curled at one corner, his eyes sparkling.
“Medium?” she asked, looking between him and the plug.
“Well, it’s larger than the last one, but smaller than the next one I intend to shove into your ass.” His fingers dipped to her pussy, tracing a path up to her ass. He slid one finger into her. Anna shoved back against it.
“That…sounds like medium,” she said, barely paying attention to what she was saying. Master Jensen added a second finger, tunneling them into her ass. His thumb pressed against her abused butt cheek.
“It’s very heavy, so it will be hard for you to hold it in. As your ass muscle stretches and gets tired, you’re going to have to concentrate and focus on keeping it in.”
“How long do I have to keep it in, Master?”
“As long as it pleases me.” He withdrew his fingers, then pulled her ass cheek to the side.
The tip of the plug centered on her anus and Anna clenched. She couldn’t help it. The plug was too big, too heavy, too scary.
“Relax or I will force it in.”
“I—I can’t,” she whimpered.
“You have until the count of five. This can be very painful, or simply uncomfortable. The choice is yours, but this plug is going up your ass. One.”
Anna took a shuttered breath. The churning mixture of arousal, fear and submission made it hard to think.
“Two.”
The part of her that enjoyed masochism wanted to stay clenched, to feel the force and power of him as he bowed her to his will.
“Three.”
Her submissive part wanted to relax and let the plug slide in, stretching and filling her.
“Four.”
Anna took a deep breath, released it, and relaxed. She was, above all, a good—if not always completely obedient—submissive. If her Master wanted the plug inside her, she would submit; she would do what she could to give him what he wanted, to accept his dominance with grace—and she would trust that he knew her well enough that he would give her that pain she craved when it pleased him to do so.
“Good girl.”
The plug pressed in. There was barely any tapering. It almost felt as if he were trying to shove something flat into her. Anna took deep, slow breaths, struggling to relax. Jensen pulled the plug back, then pressed it against her again. This time her body gave, yielding to the heavy, hard thing. Her anus stretched, past the point of comfort. Anna cried out.
“Almost there,” he soothed. “Take this for me, my Anna. Yes, that’s a good girl.”
“It’s so big.”
“I know. I want you stretched.”
It slid in deeper, opening her further and Anna dropped her head, tears stinging her eyes. Jensen’s other hand was firm on her back, holding her down as he focused on her exposed and abused ass.
“A little more,” he soothed, his thumb rubbing the stretched ring of muscle. He shoved and Anna screamed.
“That’s it,” he whispered. “This is the widest part. I’m going to hold it here. I want you to accept it. Feel how stretched you are.”
“Y-yes, M-master.”
Anna’s anus tightened around the plug, clenching the massive thing. She cried out at the pain, at the invasion…and cream flooded her sex.
“Do you like it when I hurt you like this?”
Anna raised her head, met Master Jensen’s gaze in the mirror. They both knew the answer, but she said it anyway. “Yes.”
“Don’t look away.” With their eyes locked, Jensen pushed, the plug sliding all the way in, her body clenching around the neck. Compared to a moment ago, the neck was much smaller, but by no means small. There was no way for her to ignore how she was being stretched.
Jensen’s fingers slipped into her pussy. “You’re tight.”
“Your fingers feel big. Really big.”
He stroked her spine. “Finger. That’s only one finger.”
“One finger?”
He laughed at her shock. “I was going to fuck you, just enough to take the edge off.” He leaned against her, letting her feel the long, hard length of his cock. “But I don’t think I’ll fit.”
“You’ll fit.” Anna had no idea if that was true, but she wanted his cock in her, no matter the cost.
“I’ll fit somewhere,” he said darkly.
He circled the horse, showing her the crop he’d picked up off the floor. Laying it across her back, he undid his pants. Anna could have cheered. He was, unsurprisingly, underwear-less. His cock was long and thick. The tip was glistening, the foreskin pulled back to show the delicate mushroom head. She knew his cock almost as well as she knew her own body.
Anna wiggled off the horse, groaning as the plug pressed against her. She couldn’t wait to drop to her knees and take him into her mouth.
Crack.
The crop struck her left breast, beside the nipple. Anna jumped, nearly falling due to her arms being behind her back.