Sasha's Adventures Ch. 05

He began lightly tonguing the area right between her pussy and ass. He ran his tongue just by the rim of both holes but never gave her the satisfaction of entering either. He breathed in the fresh soapy smell of her body and began licking at the edge of her anus with just the tip of his tongue. He pressed his thumb against her clit as he did so giving her competing sensations of lightness and pressure.

He continued rimming her and keeping pressure on her clit, occasionally slipping a finger inside her pussy. Her body was shivering but she wasn't cold. He pulled back away from her and stepped off the bed. He heard her sigh in frustration. She couldn't see him without turning, and thought better of it and just remained still. She felt him on the bed again, and then felt a cool liquid on her ass. He flattened her body so she was lying on her stomach with her hands over her head and legs spread wide apart.

She had her head turned on her side and he leaned over her and spoke quietly near her ear. "As best as I can tell, you have been close three times. I think we decided five was the magic number tonight so I have more work to do." He reached down and ran his finger around her anus. "I think this is the best place for me to finish the job, wouldn't you agree?"

She closed her eyes and whispered yes. He moved down her body and used one hand to spread the firm cheeks of her ass apart. He traced his finger across the puckered hole and rubbed in the astroglide he had bought earlier. As he continued rubbing, he pressed the tip of his finger a little further into the tight entrance, just teasing it open. He continued rubbing with his finger, venturing a little further in and he gradually felt the tight ring of her anus begin to loosen. He was hearing quiet moans as she buried her face into her arms and the bed. He continued his slow entry until he was able to slide one finger all the way inside. It was shockingly tight but it was clear she was enjoying his efforts. Her was struggling to remain still and her pussy juices were gathering on the sheet under her.

He dripped on more of the oily lubricant and began working on a second finger. He pulled her to her knees so he could tongue her pussy while working his hand on her ass. She tried to push his tongue into her and it was apparent she was becoming desperate for penetration. He continued working his middle finger at her entrance, pressuring it inside her. He vigorously licked at her pussy and sucked at her clit to distract her and overwhelm her senses. He pulled his face away and added more lubricant to his finger and drove it inside her. He used his other hand to start fingering her pussy, knowing she would be unsatisfied with just a finger. His hands continued their attack on her holes, and he could hear her whimpering. Her body was moving unsteadily, and he knew she was at the brink. He pulled his fingers out of her without warning and she collapsed onto the bed on her side. Her was taking sharp breaths and even without seeing her eyes he could tell she had reached duress.

He pulled off her blindfold and snipped off the zip tie. She rolled onto her back, her arms bent and wrists up by her shoulders. Her breathing slowed and he stood next to the bed looking over her. She opened her eyes and looked up at him, not daring to be the first to speak. He remained silent and climbed back on the bed. She leaned over her and kissed her, and she could feel his hard cock moving around the entrance to her pussy. She moved her legs apart, hoping this was finally it and awaiting his entrance inside her. Wordlessly, he moved his cock to her wet opening and slid inside her pussy. He thrust in her firmly and she felt her body relax in pleasure.

But he wasn't going to let her go so easily yet. His thrusts slowed and he pulled out of her. He looked at her and could see alarm in her eyes and knew she needed an orgasm. As delicious as her pussy tasted and felt, he had other plans tonight. She obviously enjoyed ass play, and despite the tightness of her opening he needed to take her ass tonight. He suggested blindfolding her again unless she could keep her eyes closed, explaining that for her to fully lose control and needed to focus. She promised to keep her eyes shut. She remained on her back and moved her legs apart so she was spread open before him. The air felt cool on her wet openings. He rolled a pillow and placed it below her lower back so her ass was angled up toward him. He rubbed lubricant over his cock and placed his head at her tightest entrance. Drawing her breath she realized what was going to happen. She had enjoyed anal sex in the past but it had been a couple years since she had tried it. And when she did it she preferred to start in a different position as the man on top of her only seemed to enhance the tightness and pressure in her anus. She took a couple deep breaths as she accepted his power over her.

Keeping a hand free to guide his cock, Tom leaned over and pulled on her nipples with his mouth. Diverting her attention seemed to help open her up, and the harder he went at her nipples the more readily her ass accepted his cock. She grabbed a nearby pillow and pressed it against her mouth to muffle her cries. He admired her restraint and continued driving his cock into her. He had passed two tight rings of muscle and knew he was in. He pressed until he was completely inside her. He pushed the pillow away from her face when she calmed and told her to lean up and open her eyes. He sat upright between her legs and she realized his body was flush with hers, meaning his cock was all the way up her ass. She dropped back down and closed her eyes. He held her legs up and began shallow thrusts in her ass.

As he did so she felt a head rush, and knew she was going to come soon and hard. As he pulled back she pushed toward him to maximize the friction and deepen his cock. She let off a loud moan as he thumbed at her pussy and then he felt the surge of wetness. Her body relaxed and he slowed his thrusts to allow her some relief. He wanted to give her a moment before he made his next move. He slowly slid out of her, and looked at her anus to see if it would remain open. It did.

Her eyes popped open in surprise. Surely he had not finished, she was certain he had not come yet but she had been so focused on herself maybe she was wrong. She leaned over her and quietly advised her what she was going to do next. He told her that he was going to lie down, and she was to straddle his body facing away from him and looking into a mirror in the room. Uncertainly she followed his directions, and she began lowering her hips until his hand stopped her. Again she felt the head of his cock at the opening of her ass. He wanted her to impale herself with his cock in her ass. She inched forward hoping to better her position, and reached back to spread her ass cheeks apart. He placed his arms behind his head to watch. Once she realized he would not be helping this process, she reached around to hold his cock. She moved her body back and held his cock in place. She had the head part way in and she just didn't think she could go any further. She had paused for a second, and moved her ass back quickly. There was an audible sound as he popped into her and she was momentarily stunned. The entry had caused a quick shock of pain, but now that he was fully inside of her she was comfortably full.

He reminded her to watch, and she stared at her image in the mirror as her ass began riding his cock. She had to admit her body looked good at this angle, and she began stroking at her breasts while she worked her hips to move him around her ass. She moved slowly at first and then was ready to go harder. She adjusted her body and bounced harder on his cock. Her ass squeezed around him so tight he still couldn't figure out how he ever got in there in the first place. But as her pace quickened, his cock swelled and she cried out and she felt him pumping her rectum full of his come.

She gingerly moved off him and kneeled on the bed, looking to him for his next instruction. He put out an arm to pull her in to him, and she leaned in and rested her head on his shoulder. She ran his fingers over his chest that was glistening with sweat. They laid there in silence until both were more relaxed. Sasha suggested a shower, and that he could either join her or watch her. He opted to share the shower with her and once they were both wet she began lathering his body. As she rubbed his cock she was a little amazed that he seemed to be getting hard again. He took the soap from her and rubbed the liquid in his hands. He began soaping her and eventually had her bend down so her could properly wash her entire body. He ran his slick hand over her pussy working his fingers inside. Thankfully he just washed the rim of her anus as she didn't think her ass could take anymore tonight.

They got out and he began to dress, letting her know that he needed to go back to his room tonight. He pointed out that he had let her come earlier than he should have and that he expected he would be traveling back to her state several more times until the election. She gave him her contact information and let him know that she would be awaiting his instructions to her for the rest of her 'punishment'.