Roll For Initiative Pt 02

Previously on "Roll For Initiative"... the below three paragraphs are taken from the end of Part 1 as a brief reminder of where we left Jane and Will....

Jane covered her face with her hands, slightly embarrassed at how loud she'd gotten. Her mind raced through what she had said to him. What she had ordered him to do to her. She'd never been so bold in her whole life. And now here she was, coming down from a massive orgasm after she had told a coworker to stick a finger in her ass, and he'd done it.

He stood up, standing over top of her. From this position, he looked massive to her, his big dick sticking straight out in front of him. He stroked it a few times and it got a little harder and longer as he gave it some stimulation after being ignored for some time while he had gone down on her.

She had an image flash through her mind of him stroking his dick until finally he came, letting loose all over her, covering her in his cum. Although it was all in her mind, she could almost feel the warm liquid cascading down on her body, covering her chest and tits and face. Is that what she wanted? To be covered in semen like a cheap, used, slut? No, what she wanted was to feel him fuck her, fuck her in whatever way he chose and cum deep inside her. But part of her, clearly, wanted to be covered by his cum over and over. What was he planning?

Roll for Initiative Ch. 02 - Grapple Check

Will smirked down at her. He reached down and put his hand out, she grabbed and he helped her stand up. He kissed her slowly. When he pulled away, he lifted her shirt up over her head. Hugging her close and kissing her again, she wrapped her arms around him as tight as she could and pressed her body into him. Jane felt like she was melting into his body, feeling his raging hot penis press into her stomach. Will pulled away from her and took her hand, leading her to the bedroom.

The short walk to his bedroom revealed what she considered to be a typical bachelor room. Simple clothes dresser, a large TV with an XBox One wired beneath it, and a simple looking bookshelf. She was thankful to see that his bed looked made out of substantial wood and was generously sized, at least a Queen sized mattress.

Without looking at her, Will simply ordered her to get on the bed and disappeared into a walk-in closet. She laid down on the bed and watched as he came out with several shirts. Her mind raced as to what he could be planning now. Then he went back towards the living room and came back with a pair of dice.

"Now, what would you like to do?" he smiled.

"I uh... I want you to put that big dick in me and fuck me till you cum."

Will handed her one of the dice. "Roll a persuasion check."

Jane took the die and stared at it. What he did to her next was going to depend on a roll of the dice? Interesting. She shook the 20 sided die in her hand and rolled it on the bed, her breath caught as she saw the number, a 5.

"Looks like you're not going to get what you want," Will smiled as he began rolling his own die and let it roll on the dresser. "Now I'm going to roll a grapple check. If I pass, you'll be restrained. Ah, a 19. I'd say that's passing."

"Put this on," Will said and handed her a padded sleep mask. Intrigued and excited, she placed the mask over her eyes as her view became pitch black. Next she felt Will take her hand gently and tie something, must have been one of the shirts, around her wrist, securing it tightly. She felt her arm stretch out to her side and heard Will tying the other end of the fabric to the bedpost.

"Oh my," she said and giggled. "Don't hurt me Master. I'm just a sweet, innocent girl."

She felt Will do the same with her other arm, then he leaned in close and whispered in her ear, "Just tell me if it becomes too much."

Then she heard and felt more rustling as Will used more pieces of clothes to secure her feet to the bottom parts of the bed posts. She heard Will leave the room. She couldn't see, but when he came back he was carrying a bottle of whip cream and a glass of bourbon, and her cell phone.

It was an iPhone. He knew he wouldn't be able to get into it without her password, but he just wanted to use her camera. He figured if he took pictures of some of this on her phone, it would be up to her to delete it or keep it, depending on how happy she was with the results.

He made sure the sound button was in the "On" position and activated the camera. "You're going to have some interesting pictures on your phone," he said and began snapping a few pictures of her from different angles around the room.

"Oh my god, please. Please fuck me, Will. I need it so bad."

He held onto phone camera as he took a few sips of bourbon. This time he flipped her camera to the video position and said to her, "Tell me what you want."

Jane breathed deep and stretched against the ropes, desperate to move her arms, to reach out and touch him, to touch the bed. "Please, where are you? I just want your big dick inside me so bad Will. Please fuck me."

Will rolled her dice on the bedside table next to her and said, "Hmmmm... another failed persuasion check. Looks like I get to keep doing what I want."

Will put the camera down and sat down next to her on the bed. "Now it's time for me to have my fun." He looked over her ripe body and drank it in, he ran a hand down her body starting at her left foot and moving up her leg, feeling her muscles, moving up to her pussy and grabbing it tightly, moving up her tummy and up to her ample breasts. They were beautiful, and he told her so. "I never would have guessed what gorgeous tits you have. You really keep them hidden at work."

He grabbed her left breasts and moved her hand over her tit, then moved his hand up her chest to her neck, holding her head as he leaned in for a kiss. Then he sat back up and said, "This might feel a little cold." With that he sprayed a large mound of whip cream over each of her breasts. Might be a little bit childish or corny, but he had always wanted to do this to a beautiful woman like Jane. Jane yelped and giggled as she felt the refrigerator cold cream pile up on her body.

He quickly snapped a picture of her prone body with her tits covered in whip cream, then set the phone on his clothes dresser, leaving the video mode on as he indulged himself. He got between her legs and leaned over her, pressing his face into the whip cream and began licking it off. He licked, sucked, and kissed her breasts as he gobbled it all up off both sides of her body. Will was loving every minute of it. When he was done he spent more time continuing to suck on her right tit while he fondled the other with his hand. Jane cooed and moaned throughout his ministrations.

"I love the way your tits feel in my mouth." Then he stood up again and started rummaging around in his nightstand, looking for something. He wasn't sure if this was going to work, but it might. He found a small vibrating massage tool he'd bought a while back to work out some kinks in his muscles. Not one of those big pulsing guns, just a little thing that fit in the palm of his hand and had little feet that vibrated, meant to be used with massage oil. He found the massage oil and checked the ingredients. Ah ha, water based lubricant. He knew from touching her a few moments ago and having his face buried in her pussy in the other room, that she was plenty wet enough. But he did spray a few drops of the water based lubricant on the soft feet of the massager, just to ensure it would be comfortable.

He stroked his dick a few times, and sat down next to her. Reaching over with his left hand, he placed it over her pussy and began gently opening her, pressing the tip of one finger inside her and holding it there, letting her grow accustomed to the pressure again. She breathed heavily and pressed her body up into him, wanting more pressure. "Please," she said. "I need it. Your dick, I want it so bad."

He maintained his pressure, gently placing a fraction of an inch of his finger more inside her, and then pressed his crotch towards her face, letting his rock hard dick fall onto her face. She smiled and opened her mouth wide. He manuevered it strait into her mouth and began fucking her mouth again as she moaned in happiness. "You want this dick? Huh?" Then he removed it from her mouth. She gasped and said, "Yes, more please."

He pressed it back into her mouth, hard, "Exactly, you need this big dick anyway you can get it, don't you?" He removed it from her mouth again and slapped it across her face. "Yes," she said, gasping for air, "Yes please."

He said, jamming his dick all the way into her mouth, "I've taken your control away. I'm gonna do what I want to do. Use you for my pleasure. Do what I want. You're tied up just the way I want you, exposed and immobilized. At my mercy to do with as I want."

For himself, his dick felt amazing being sucked and fucked by Jane's mouth. He believed the moans around his dick and the steady pressure from Jane into his hand indicated she liked what he was doing as well. "Holy shit your mouth feels amazing."

As much as he was enjoying the feel of her lips and tongue over his cock, he still had plans for her. Regretfully, he removed it from her mouth and moved down to the center of her body again. He placed the massager in his hand and turned it on its lowest setting. Holding it in one hand, he placed the other between her legs, then he pressed them both to her body, using his free hand to open her body to him and apply the massager gently to her clit.

Her body primed and desperate, Jane cried out in pleasure as the light vibration stimulated her and two of his fingers penetrated her. "Oh, oh... oh god." He pressed his two fingers deeper inside of her until he felt the pressure was enough, then he began gently pushing them in and out, finger fucking her at a steady, firm pace while the vibrator moved gently on her clit and making tiny slow circles over the area. He experimented by pressing it harder into her and watched as her jaw dropped and she cried out, "Ok Ok, oh fuck!"

He removed the vibrator and watched as she returned to a more serene state, her pussy clenching around his fingers repeatedly. He moved his face down to her center and began sucking, licking and kissing her clit again, moving his tongue all around her and inside her, then out and up to kiss her clit again.

"Oh my god Will, I'm gonna cum again, please please, put your dick in me. I want to feel you fuck me."

He picked his head up and replaced it with the vibrating massage tool. Then Will said, "You'll get this dick when I think you deserve it. You will cum when I say you can."

He pressed the vibrator into her harder and removed the sleep mask blindfold, looking directly into her eyes, "Look at me. Don't you dare cum until I tell you too."

She stared into his eyes, her breathing becoming ragged, her chest heaving up and down as her body threatened to explode all around her. Her hands clenched into fists as she forced herself to hold her orgasm at bay. "Please master, tell me, tell me.... Oh god, tell me what you want, I'll do anything." Her mouth gaped as her leg began shaking against the restraint.

"Tell me what a fucking slut you are." He pressed the massager harder into her, altering the pressure every few seconds.

Jane gasped, took a deep breath and tried to gain some composure, looking back into his eyes and saying, "I'm your dirty slut. I was made to be used by you like a fucking whore. My filthy body is your personal toy. I... I want to be your cum dumpster, Master."

Jane clenched her eyes tight as she felt waves of pleasure crashing through her. Her cheeks went scarlett and hot as she thought about what she'd said, basically asking Will to use her as a fuckdoll. But in that moment, she meant it, she was about to explode and she wanted, needed, to do whatever he said. Whatever he wanted.

Will positioned his body over her and let go of the massager, placing both his hands on her shoulders as he moved his dick over top of her pussy. He guided it in, just the tip and held it there. She screamed as she felt it enter her.

"Take this dick in your tight little pussy." He pushed the head of his dick inside her and began moving it in and out of her, never going much past the first inch or so. She loved it anyway, she didn't have a choice at this point, he could feel how hot, wet and tight she felt. It felt amazing. He placed his hands over her neck and squeezed, just a little.

She gasped as she felt the momentary pressure on her neck before he released it. He still held his hands around her neck, but not putting any pressure on them, just letting her feel their light grip. He looked deep into her eyes and kissed her as her eyes boggled. He kissed her deeply and then lifted his face from her, her head straining to lift up, to maintain contact with him, the head of his penis continuing to pulse in and out of her.

"Ohhhhhhh Will, pleaseee," she moaned, her face sweating, her chest flushed. Her body felt a hunger for him she'd never experienced before, fueled by the orgasm she was on the edge of, she wanted him more than she had ever wanted anyone else. She wanted to bite him, eat him up, drink him in. She wanted their flesh to melt together. She wanted to be covered in his cum, filled up by it. She couldn't think straight as the pleasure coursing through her body threatened to overtake her. Her breathing was ragged now, she felt nothing except currents of pleasure coursing through her. She felt like there was an ocean about to crash over her. She couldn't hold out any longer, could she? Her body felt like it was on pins and needles, the pleasure built up on her like she was at the top of a roller coaster.

He put a small amount of pressure back on her neck, looked into her eyes and ordered her, finally, to cum, "Do it, cum all over my big dick."

Through the pressure on her neck, she cried out, straining against his hands and gasping for air, screaming, "Yes god, holy shiiiiiit." Before her words trailed off into unintelligible groans and gasps. Her legs and arms shook against the shirts tied to them and he felt her body clamping repeatedly around the head of his dick. Finally, her right arm tore loose from the shirt tied around its wrist and she flung her arm around him tightly and pulled him in close for a deep, desperate kiss, her tongue lunging into his mouth as her orgasm continued to crash all around her.

Kissing her deeply, Will released the pressure on her neck completely and put his arms around her body, pulling her close and hearing her gasp for air and cry out as another wave coursed through her body. "Keep coming for me Jane, please, I need you to keep cumming."

She hollered, "Oh god!" as her words were choked off as her, filled with desire and pleasure, was rocked by another orgasm. Her body continued to roll through the explosions inside her. Her hands shook as she tried to hold onto Will. She felt him lean down and take her tit into his mouth, kissing and sucking gently and sending another crashing wave of an orgasm through her exhausted body. She felt tears falling from her eyes and she cried out again.

Her eyes rolled into the back of her head as her body finally stopped shaking and she began to reach the end, he kissed her cheeks and neck, caressing her gently with his hands and lips as the waves began to slow and the peaks gentled. Finally, she stopped and was just breathing heavy with her eyes closed, sweat having broken out all over her body. He got up and untied her, she brought her legs and arms close to her body and rolled onto her side, wiping sweat from her forehead as her breathing slowed.

Will smiled as he stood next to her, reveling in how good he had helped her to feel. He climbed into bed behind her and held her close, kissing her cheek.

After a few minutes she said quietly, "I guess this means I broke your grapple, right? So, is it my turn?"