Roll for Initiative Pt. 01

She looked him in the eyes and bit her lips, then looked down at his crotch and smiled. She put her hands in his pants and began undoing his fly. As Jane unzipped his pants, she dragged them down to his feet as she got down on her knees. She stared at the huge bulge in his underwear and pressed her hands to it, grabbing hold of his engorged cock over his remaining piece of clothing. She smiled up at him.

"Take off my clothes and put my dick in your mouth. Only use your mouth"

Jane blinked at him and then clamped her teeth around the waistband of his boxer briefs. She pressed her teeth hard together and began dragging his boxers down his legs. When she moved them past his very stiff erection, Will's dick popped out of his clothes and hit her in the face. She loved it, but she kept going, pulled them all the way down to his feet and on top of his pants using only her teeth. Then she slowly began sitting back up. She stuck her tongue out of her mouth and pressed it to his legs when she got above his kneecap.

She wanted to hurry, to slam it into her mouth so she could satisfy the burning sensation in her belly to touch his dick. But she made herself slow. She slowly dragged her tongue up his leg, across his hips and then down the top of the shaft of his dick, swirling it all around the head of his large dick before finally enveloping it in her mouth. She was rewarded for her torturous efforts with an unsupressed, loud moan from Will.

She began slowly bobbing her head up and down, rolling her tongue around his dick, which felt incredibly hot in her mouth. She felt like it had been forever since she had truly gone to work giving a man a blowjob like this and she was loving every minute of it. Will's throbbing penis felt wonderful in her mouth and she enjoyed hearing his loud moans of approval.

Will was in heaven. In all his dreams or fantasies about how things might go if he made a move on Jane, this is not how any of them went. He had at best hoped to be able to go out to dinner with her and maybe kiss her. Now she was giving him an unbelievable blow job. Still, he felt like he should continue to press forward. Being bold had served him well so far. He decided to continue to listen to what she had told him a few moments ago, and take charge.

He placed a hand behind her head and for a few moments, he forcefully shoved his dick into her mouth, aiming to drive past her gag reflex. He jerked his dick out of her mouth completely, seeing her shocked face for a few moments, with the beginning of tears forming in her eyes, and then he shoved it back in past her lips as far as he could again, repeating the process a few more times and reveling in how her mouth felt.

Then he removed his cock from her mouth and stepped back, demanding she "Lay down on the floor."

Jane shook her head a few times, recovering her composure after having her mouth forcefully fucked. No one had ever fucked her face like that before. It had been shocking, but she loved it. She lay down on the floor in front of Will and propped herself up on her elbows, staring at his dick and waiting for what was to come next.

Will stripped the rest of his clothes off and then got down on the floor with her. He kneeled overtop of her, grabbed her by the shoulders, and roughly shoved her to the floor. "I said lay down." Then he proceeded to remove her pants and underwear.

When he was finished he moved his face to her pussy and began lightly kissing all around her, pressing his face deep into her and resting his head on her pussy for a few moments, enjoying how soft her body felt. "You feel amazing," he said. "Don't move."

He stood up and walked over to the couch and grabbed two pillows. He placed one under her head. The other he brought with him as he kneeled in front of her. He grabbed both her legs and picked them up, resting them on his shoulders for a few moments so that her ass was elevated off the floor. Then he placed a pillow under her and lowered her butt to the pillow and said, "Should make things easier."

Jane assumed that he was going to enter her now. She wished he had taken the rest of her clothes off so she could feel his body, but she was sure she'd get the chance to feel that later. But, she didn't expect what happened next.

"Open yourself to me."

Jane reached her hand down her body and spread herself open for him, closing her eyes and waiting for his dick to plunge into her. Instead she felt his head return to her pussy and his tongue began working her over, licking all around her and sliding inside her every now and then. A moan escaped her lips and she began breathing heavy. She hadn't been touched like this in a long time.

Will's oral ministrations continued and he reached up and grabbed her tits with both hands as his mouth kissed, sucked and licked all over and inside her. Jane began to press her body harder into his mouth as her breathing got heavier.

"Tell me what you want."

His tongue stopped moving and it took her a second for her mind and body to stop buzzing. She looked down at him and saw him earnestly looking up at her. She had been lost in her own body, well on her way to a strong orgasm and it took her a moment to think about what he said. Tell him what she wants? She had been getting what she wanted, and then some. But for a few moments she considered it. He was giving her an opportunity, something no man had ever done before. He was giving her a chance to tell him anything she wanted in this moment, testing her to see how open or depraved she could be. How much she could succumb to desire. She had told him that she sometimes liked being the boss, and this was her time.

"Put your tongue inside of me and hold it there."

Will moved his head down, stuck his tongue out as far as he possibly could and slid it inside her pussy. He wiggled it around a little and then held still, waiting for more instructions.

"Now fuck me with your tongue until you feel me cum."

Will started in earnest right away, sliding his tongue in and out of her with reckless abandon. Jane laid her head back down and felt the heat rising in her body again. She was racing towards an orgasm as she felt his soft tongue assault her insides. She began moaning loudly, refusing to hold back as she felt Will continue. He changed pace, slowing down and moving his tongue in different directions inside of her, adding fuel to her fire as she said, "Yes," quite loudly.

No man had ever gone down on her this long. The most she'd ever gotten before was perfunctory pre-intercourse attention, only just long enough before the man decided he was good to start fucking her. Now, the way Will was going to town on her she felt like he may not even care about fucking her, that maybe he'd just be happy to please her like this. This thought, that Will maybe was not in a hurry to fuck her, to put his hot thick penis inside her body, made her want him inside her more than ever. Made her want to feel him fuck her brains out and explode deep inside her.

She cried out in pleasure and said, "Stick a finger in my ass!" She heard Will grunt as he buried his face deeper into her body and jammed his tongue even farther inside her. She felt one of his hands lift her body slightly off the pillow, moving into position. She felt a finger roll around where his tongue was, sliding inside of her and coating the finger in her fluid. Then she felt his finger move down her body and probe her asshole, gentling sliding inside a few times. The finger was removed and traveled back to her pussy, jamming deep inside her and getting coated once again before returning to her ass and sliding all the way in, up to his big knuckle.

The feelings were so much now, completely overwhelming her when she hadn't expected any of this. Will's tongue deep in her pussy, rolling around in her, lapping at her insides. His finger pushed into her asshole, sawing in and out of her. Every few seconds, Will would pull his finger all the way out of her and then plunge it back in. The pressure was building deep in her core, she cried out in pleasure as she felt a wave about to crash over her body.

Just at that moment, when she needed it most, Will's face lifted from her body and growled, "Cum on my face. Cum for me right now." Then he planted his face back into her body and redoubled his efforts with his tongue, pressing it as deep into her as he could go.

Jesus, she had never been ordered to have an orgasm before. She'd been begged by men who were having trouble pleasing her, but never ordered to by a man who was working her over the way that Will was. As his finger plunged into her ass again and his tongue pressed into her, his other hand reached up and twisted her left nipple, hard. She screamed and arched her back.

Her mind was racing, pleasure coursing through her body. She wanted to cum so bad. She wanted his dick inside her, right this minute. But she also didn't want him to stop fucking her with his tongue. She wanted it all. She felt crazy. She imagined having his tongue inside her, his finger in her ass, his dick in her hands, imagined him kissing her... all at the same time. She wanted it all. She wanted to feel his dick erupt inside of her and fill her up. She also wanted to feel him cum all over her, his semen splashing all over her body. She wanted his dick in her mouth. She was going insane. He was making her insane. She howled as she felt his tongue run over her clit, sucking on her. It built inside her until finally, it slammed into her like a freight train.

She shouted, "I'm cumming!" She heard and felt Will growl beneath her and against her, she lost all recognition of what he was doing as she succumbed to the wave crashing through her and her body convulsed through her orgasm.

As he felt her body convulse all around him, Will smiled and eased the pressure off of her just a little, gulping a giant breath of air as his face had been buried tight to her body for a while. He watched as Jane's arms flailed at her side and her eyes rolled into the back of her head and she said again, "I'm cumming, oh god, I'm cumming." Quieter this time as if she was having trouble getting a full breath.

Slowly, her heart rate slowed and the tingling throughout her body subsided and she lay there with her eyes closed. After a couple minutes her breathing returned to normal and she opened her eyes to see Will smiling at her. He said, "You look gorgeous."

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?