When the door opened some time later, she didn’t lift her eyes to his. Instead, she brought it to the tips of his cowboy boots, and then, when he stepped closer, to the end of the riding crop he held. She swallowed then and slowly raised her gaze to find him shirtless, his eyes dark, aroused, his expression something other.
“Stand up, Megan,” he said.
She rose quietly, knowing not to speak, not having a thing to say.
“Hold opposite elbows behind your back when you’re unsure what to do with your hands.”
She did, grateful for the instruction. Her eyes fell once again on that crop with its rectangular end. She could almost smell the leather of the thing. It was new; at least she’d not seen it before.
“Eyes on me, Meg.” She met his eyes, blinking several times. If he had asked her what she felt at that precise moment, she would have been unable to tell him. Her mind was blank. “You know what I want to do tonight, Megan?” he asked.
She shook her head no.
“Answer me with words please.” His tone was so different than when he spoke to her normally.
“No, sir.”
He smiled, clearly pleased.
“I want to prepare you,” he said, taking something out of his pocket and holding it up to her.
She looked at it, understanding what he meant by preparing her. Her sex throbbed at the thought of it.
He walked around her, setting the crop on the desk and bringing a small, low wooden bench to place before her.
“Bend forward and place your hands on the bench,” he said. “Legs wide. Hollow out your back and lift your hips.”
He moved behind her as she assumed the position he required of her. She took it without hesitation, lifting her bottom high, presenting it to him, offering it to him.
“Take your panties down to your knees,” he said.
She imagined his face as she reached back and pulled her panties down to expose her bottom.
“Good girl,” he said, his voice thick. She felt cool drops of what she assumed was lubricant poured onto the top of the cleft between her cheeks. “I’ve never had you here, Megan,” he said, one finger dipping into the stuff and sliding downward toward her bottom hole, circling it slowly, softly. “I’ve never taken you here but I think it’s time.” Two fingers now worked the tight hole, the sensation foreign and strange but not unpleasant, especially when with his other hand, he found her clit and began to rub.
Her breath grew ragged and when he pressed then slid the tip of one finger into her back hole, she gasped, stiffening. “Jake.”
“Shh… Relax. The first plug is small, you can take it. It’s just my finger now. There, that’s it, relax. Take it in, good girl.”
He pressed into her and withdrew his finger several times and when she began to moan, he added a second. She clenched again at the wider intrusion but he probed and in time, she accepted without protest. She’d not had anal sex before and he had only touched her there once or twice. She had always thought it was an accident but this felt good, better than she thought it would.
“I think you’re ready for the plug, baby.”
She groaned, not quite sure herself.
“You’ll wear it for some time tonight. It will help stretch you so it will be easier when I take you here.”
“Will it hurt?”
“It might be uncomfortable at first but you’ll get used to it.”
Jake watched her bottom as he moved his fingers in and out of her tight hole. Her pussy was wet, the lips slick with her arousal, her clit swelling between his fingers. She was reacting well so far, but he wondered how she’d take it when he striped her bottom with the crop.
He removed his fingers and picked up the plug, his eyes on her ass as he lubricated it. Her submission didn’t surprise him, but her quiet did. It was almost as though he were touching on another part of her, a part of her mind he wouldn’t have access to without this developing dynamic between them.
“Don’t tighten up, Meg. Just relax, you can take it.”
He put one hand back on her clit and began rubbing and she relaxed as he did. The plug was one of three he’d bought in varying sizes. This was the smallest one, just two inches long and one inch in diameter. He wanted her ready to take his cock soon which would require much more of her than this plug.
“There, almost in,” he said, playing with her, pushing in and drawing it out as her body relaxed and she softened for him.
“I’m…” she began, but before she could finish her sentence, her hips bucked as she came and he held her clit tight, pushing the plug the rest of the way in, seating it inside her bottom. She made some sound, bending her knees, pressing her thighs together, squeezing out the last of her orgasm. When the wave had passed, she began to straighten, reaching back to touch the base of the plug.
“Did I tell you to rise?” Jake asked, picking up the crop.
She glanced back and resumed her position. “No, sir.”
“I’m going to give you twenty with the crop, just to warm you up. Hold your position until you’re told to straighten, is that clear?”
“Yes, sir.”
Jake lined the crop up against the center of her bottom, tapping it once, twice. He then drew back and struck. She gasped as leather connected with soft flesh.
“You wouldn’t be so tender if you hadn’t come, Meg,” he said, his voice stern even though he didn’t mean this as punishment. He brought the crop down again twice in quick succession. “When we play, you’ll have to wait for permission to come or you’ll be punished, is that clear?” Three strokes of the crop accentuated his words.
“Ow, ow! Yes. Ok. I couldn’t help it. Ow!”
“Straighten your legs and bring them together. The last ones will be across your thighs.”
She groaned but did as he said. The fact that she held her position as he struck excited him. Her small sounds excited him. And the marks the crop left behind most definitely excited him.
“It’s over,” he said, setting the crop on his desk. “Remain as you are.” He walked out of the study and to the kitchen where he washed his hands. He then checked the time and took a bottle of beer from the fridge before returning to the study to find her exactly as he had left her. He smiled and went behind her to check the marks of the crop. He imagined she’d be warm from the strokes but she wouldn’t have any more pain or if she did, it would be quickly fading. He would take the cane to her ass one day soon, but not yet. Not tonight. Tonight, he had other plans.
Without a word, he helped her to rise to her feet and walked her over to the sofa.
“On your knees here,” he said. “Keep your panties at mid-thigh.”
She glanced at him for a moment but did as he said, sliding down to her knees and adjusting her panties. He smiled down at her, picked up his notebook from the desk and took his seat on the sofa with her at his feet. “Knees wider, Megan. Good girl.” Keeping one hand on the top of her head, he began to review his notes.
Or at least he pretended to.
Megan’s bottom hurt. Well, it wasn’t so much that it hurt badly anymore as the fact that she was very aware of it. The crop had left a warmth behind which she didn’t altogether mind now that it was over. She imagined, however, if he used it for punishment, she would be singing a different tune.
Her bottom had adjusted to the plug more quickly than she had expected it to. She was a virgin there, but tonight, Jake’s treatment of her, Jake’s very intimate exploration of that part of her had her thinking of what was to come. She wondered how long he would make her wear the thing before he played with her again. He wouldn’t fuck her there tonight, at least that was what she had understood. She only wished she could bring her knees together for a minute, relieve her swollen clit. Her orgasm had provided release but now, sitting here like this at his feet, her panties not altogether off but simply taken down, she felt more exposed than ever. More submissive. No, that was not the right way to say it. It was more the fact that she felt his dominance over her. And she wasn’t fighting it. She wanted it.
Was that strange? Should she be outraged at his treatment of her? Should she be appalled at herself? Well, she wasn’t. This just felt natural and it was like he had said the other day, that it was still them. She glanced up at Jake. He just kept reading at first but after a moment, he turned to her. He didn’t smile or speak. Instead, he kept petting her hair until she dropped her gaze back down to a spot between her knees.
Finally, he spoke, giving her instruction. “On your hands and knees here, Megan. Ass to me.”
Her pussy throbbed at his command as he widened his knees and put his notebook away. He had seen every part of her but for some reason, the posture she would now assume still embarrassed her as much as she wanted it. She crawled the few paces until she reached the spot where he wanted her and she waited.
“Down on your elbows, ass up, face down,” he said, tapping her hip twice. “When I say all fours from now on, I mean ass up face down, understood?”
“Yes, sir.”
She moved down to her elbows, her pussy juices slick along her thighs. She heard him unzip his pants as he settled between her widespread knees. His hands came to rest on either butt cheek and he spread her open. She felt his touch on the base of the plug as he twisted it inside her while his cock penetrated her pussy. Megan moaned, lifting her hips higher, clawing at the carpet.