Sean's Next Season Ch. 05

Sean slowly slid the finger out and moved his well lubed cock up with her entrance. He heard Kayce began to coach her between licks of her clit, "Relax and breathe, princess. Relax and breathe."

Sean repeated Kayce's instructions "Relax," he instructed. "I'm going to give you a safe word that if I hear it, we stop. If you can't take any more you say your brother's name. I'm going to add a second finger."

Courtney took a deep breath as Sean slid his ring finger into her, now accompanied by his pinky At the widest point she was gasping and clawing at the sheets under her. She yelped as he went in all the way. It was painful but then the pain gave way to an unbelievable feeling of fullness. Sean could sense the change and gave her a moment before he began to turn the bulb by the handle, playing with it, watching her wiggling response as he twisted it around and tugged at it, against her resisting anus.

She was enjoying it now. She was ready. Kayce licked at her pussy, "Good girl," she whispered.

Sean coached Courtney, "I'm going to pull this out. Then I'm going to fuck you up the ass. If it's too much, remember your brother's name." Just saying it was making him want to explode.

He pulled his fingers and she was gasping again at the discomfort of her ass resisting the stretching and pulling of it. Finally his fingers were gone. Surprisingly, Courtney found herself wanting her ass filled again.

Sean whsipered, "I'm going to slide into you now. I'm going to fuck you in the ass."

She steeled herself for it. He spread more lube across his pulsating cock and then pressed the tip against her anus. It felt so different than his fingers, or even his cock in her eager pussy. There was both a hardness and a soft flexibility that made her wonder if it could force its way inside. It felt big. Terrifyingly big.

He began to exert the pressure of his cock against her asshole and push. He pushed hard and felt her ass barely opening, he was pressing against her but her ass was resisting him. He knew that he'd have to push with more force to get inside of her, and that it would be a much more abrupt intrusion than the prior toys. But it was the only way.

He pushed hard enough for the tip of his cock to open her ass and slide in.

"OW OW OW OW OW OW!" she started yelling. Kayce moved out from under her and began to stroke her long hair. "You've got this princess, I promise," Kayce affirmed her.

Again Courtney started to moan, "Ow, ow, ow," she was repeating it over and over, she was squirming and wailing in pain. "Oh god that hurts so much it hurts it hurts it hurts," she howled through the hot, blinding pain of her asshole being stretched wider than ever before.

"Please, please go slowly. Slow slow slow," Courtney begged as Kayce kept rubbing her hair. Kayce wanted Sean to stop, she wanted his hot painful prick out of her but she couldn't bring herself to use the safe word, she just couldn't. He was just slightly beginning to move his cock within her, just sliding it almost imperceptibly back and forth right where it was, just the tip, but such a wide hard tip. Every little movement was so overwhelmingly painful but so was total stillness, so she let him slide in just a little bit deeper.

"OW OW OW Owwwwwww," she said but the last "owwwwww" was different, almost a moan as the pain began to change into a pleasurable discomfort. He pushed in a tiny bit further, the ridge of the head of his cock disappearing completely into her ass. He was swimming in the ecstasy of watching his cock slide into her ass. She was so spread open to him. He was hurting her a little, but he liked it, and he was sensing her just beginning to like it.

He pushed in more.

She wiggled in response, and this time instead of a painful cry she uttered a low, guttural moan.

He pushed in further. She squirmed under him and moaned again, before gasping in surprise, "what did you do? What are you doing?"

"What?" he asked, "If you need me to stop, use your safeword?"

"No, no, no, it's just that all of a sudden the pain disappeared. What did you do?"

"I didn't do anything. I'm sliding into your ass. My cock is halfway into you now."

"Oh my god the pain is just... gone. It's just... pleasure."

Sean smiled the first real smile he had in a week. Kayce looked up at him with pride. Sean could feels Courtney's pride at what her body was doing. He could feel her amazement -- she was taking it, she was going to take all of him. And she was going to enjoy it.

He pushed in further and he watched her body begin to completely relax. She was adjusting herself into a position of total submission. He was nearly all the way into her ass and she was yielding to him, opening to him, her tiny tight asshole stretching around him.

Her breathing was becoming deep and ragged now, and her words were an incoherent string of indecipherable moans, "please please please oh yes oh yes yes yes mmmmmmm oh my god oh my god more more deeeeeeper yes."

He was ready to push himself in all the way, to the hilt, and as he did her voice rose up in a high-pitched wail of helpless pleasure. He was inside of her. His entire cock was inside of her ass.

He began to rock back and forth, and she gasped. "More more more more oh oh oh oh."

Such a greedy little slut, I'm fucking you up the ass. How do you like it?" he groaned as he slowly increased his speed.

"Oh god I like it so much I like it so so so muuuuuuuch, God, I never knew..." she moaned back.

"I'm going to go a bit harder," he replied and he started to thrust more forcefully, sliding the tip of his cock almost out but then plunging back into her, deep, burying himself entirely.

She was squirming wildly underneath him and he saw her hand begin to move between her legs. Sean was moving more deliberately, but not nearly as forceful as he had been with Kayce.

Courtney began bucking violently under him and he could feel her muscles clenching around him, her asshole squeezing him tightly as her first anal orgasm raced through her body. She was getting louder, as loud and unrestrained as he'd ever heard her. Her voice was rising and falling in waves, from guttural groans to breathy shrieks. She was wild with pleasure.

She was trying to tell him that she was about to come, but she couldn't speak. She had lost all control. She could hear him moaning and feel him thrusting but all she could do was lie helplessly under him, completely overrun by pleasure.

She was trying to moan but she could no longer moan, because she was crying. She was sobbing. Tears were streaming down her face but she was too incoherent to understand why. There was pleasure and pain and love and total vulnerability and deep, unprecedented intimacy. He was fucking her ass but it was like he had hit some untouched part of her, beyond the physical. She was gasping and wailing and finally she found her words: "Maaaaaaaaaster, God, Master own me," she screamed

"Good girl," Sean growled

She suddenly flung out her arms, screaming, coming so hard that it was overwhelming, her body wracked by convulsions and waves of pleasure that brought more tears and moans. He was in awe of her, watching her flooded with sensations and emotions that he could feel pouring out of her.

He was so overwhelmed by this gift of herself, this complete surrender, that he found his own body began to clench. His balls, pressing against her hot skin, were tightening and he could feel himself ready to explode. He tilted his head down and leaned over her back, his strong arms pressing into her sides as he held himself up, thrusting into her as deeply as he could, before his own moans crescendoed into an unrestrained screaming, wailing climax. He was coming deep into her virgin ass. He was taking her, every part of her completely.

He spurted into her in a huge, convulsing, wracking orgasm that went on and on, his muscles spasming with accompanying groans of completion. She was silent and motionless under him, until the last convulsing movements faded away and it was just the two of them, quieted, raw with the wonder of it.

She could feel him begin to pull out of her and there was no pain as his cock slid through her until a sudden feeling of emptiness returned. But this time she felt satiated, no desire left, just pure exhaustion.

He moved quietly and carefully next to her, careful not to disturb her stillness. She shifted slightly towards him and he slid an arm into the space between the pillow and her breasts, his other arm around her back, his face against hers, their hot cheeks pressing tightly together. She lifted her arm to encircle his neck and pull him into a single, gentle kiss.

Kayce kissed the top of her head, "You finally surrendered to your Master. Good girl, princess." Kayce went to get a warm washcloth so that the three of them could clean up the mess that covered them.