Chapter 2: The First Milestone

Her agreement was all Graham needed as he quickly reached out, grabbing her by the neck and pulling her in for a kiss. Kelly felt herself shiver when his lips touched hers, drawing a small whine from her.

"The girl makes noises," he chuckled against her lips. "I want to fuck you. Have you ever had anything in your ass?"

Kelly felt her gut tighten at his words, nervousness and excitement sweeping through her system in a way that she almost forgot to respond.

"N-no I've never done that" she stated. Indeed, Kelly's experiences in BDSM were still minor since she was still new. Anal being something was on her list she had yet to check off.

A smile crept on Graham's lips and he let her go, moving to the other side of the living room. "Panties off. I want you down in submission. Do you know what position that is?" He asked as he rummaged through drawers.

"No, Master."

"Get on your knees. Stretch your arms out in front of you. Head down. Ass in the air."

Kelly took a deep breath. His description did well, and she was even thankful for the comfortableness of his carpet as she got down on her knees. Doing as instructed she stretched her arms out in front of her, her fingers digging into the carpet and back arching, forcing her ass into the air.

"Like this Master?" She asked, already feeling a tinge of ache in her abdomen.

"Yes, don't move. Don't look up. I want eyes to the carpet at all times."

Kelly took deep slow breaths, trying not to feel the ache in her limbs as Graham seemed to take forever finding what he needed. When the rummaging stopped, Kelly had to stop herself from looking up, curious to see what was happening. Footsteps grew close to her and stopped just behind her raised ass. Suddenly she felt something cold against her ass, then warmth as a finger pushed into it. She drew in a breath of shock, her ass pushing back into the finger of its own accord.

"Ah… good girl, someone does indeed like it." He stated with a chuckle, swirling his finger and starting to pump it slowly, making sure the lube was in. Each movement drew a soft gasping noise from Kelly. When his finger left her tight hole, an involuntary whimper escaped her taking her a little by surprise.

"Patience girl." He told her. Kelly had every urge to get up and look at him. Despite this, she held fast, only jerking away when she suddenly felt something cold push into her hole. This movement resulted in a sharp spank on her bottom. "I said don't move" came the growl.

Graham continued pushing the cold item into Kelly's ass until suddenly there felt like a pop as something entered her. The feeling was strange. Her ass felt full with something cold.

"You can move now."

Stretching before moving out of her position. Kelly noticed a mirror nearby and walked over to see what he had done to her ass. Twisting there between her butt cheeks lay a small jewel. Kelly, intrigued, wiggled her bottom, resulting in a small giggle.

"What is this?" She asked softly, glancing back towards Graham.

"A butt plug. Now come here on fours."

Kelly didn't ask him to explain. This one felt self explanatory. Kneeling in front of him, she twisted so her ass faced him again, hands pressed to the ground, knees to the ground and back arched in. Graham nodded in satisfaction and began to undo his belt. As Kelly listened to him, let loose his belt, she could feel the warmth of his hard cock press to her heat. He didn't even wait before he thrusted inside her. A cry escaped Kelly. The sensation of his cock and her filled ass differed from what she was used to. Every movement drew her closer to euphoria, every thrust a step closer to her orgasm.

"Do not break your pose."

Shaking, Kelly could feel her arms about to give way under the pleasure and tried desperately to keep herself up. Another thrust and she could not hold herself up, orgasming as her upper body collapsed to the floor. Grunting in displeasure, Graham's hold of her hips tightened to a nearly painful grip, his thrusts growing rougher, wilder, making Kelly's cries grow louder, already tired from an orgasm she has never experienced before. Graham reached his hand back harshly spanking Kelly's right cheek, thrusting a few more times than doing the same with the left. He kept this rhythm up, tears forming in Kelly's eyes, but she found herself being driven close to a second orgasm as he continued. A tenth smack on each cheek, the last strike all she needed for another intense orgasm, followed quickly by Graham's own orgasm. He pulled out, allowing her to collapse into a ball of tears and soaked juices. Taking a deep breath, hearing a little sob come from her, Graham leaned over picking her up and moved to the couch where he sat with her in his lap. His hand stroked through her hair, trying to calm her down.

"You did good. Are you regretting it?" He asked, gently.

Kelly shook her head, his calming gentle strokes starting to bring her down from her crash out of her space.

"Good," He whispered, kissing her tear stained cheek.

"W-will it be like that all the time?"

"No girl. You completed your first milestone. I want to explore what you can and cannot handle. And we will do so together."

"What if I can't do it?"

"Can't do what?"

"Whatever it is we explore?"

"Then we won't do it. But I expect you to try once."

"I will" She offered quietly, pressing her face into his neck and enjoying being held.