Hearing Sherry moan made Jono smile, as he knew he was in control of her. Using his thumb to make little circles, Jono moved his pointing finger to Sherry’s anus, and started to do the same. Immediately, her eyes flew open in shock.
“SIR!” Sherry called out in surprise. Looking at him pleadingly, Sherry calmed her voice, as she knew she did not have a ‘no’. “S-Sir..p-please not that…” she said pleadingly. Out of the corner of her eye, she thought she could see his dick appear to stiffen at her voice. “No-no one has ever..AHhhhh.” She found herself grunting as she could feel Jono’s finger push in just a bit on her annular ring. “Wa-Wa-Wait..PLEASE!” She begged. As she did so, she began to involuntarily squirm. Her face contorted to a frown as she pulled uselessly against her ankle restraints. A tear started to form.
Jono, for his part, enjoyed seeing his new property squirm. This was not so much about anal, it was about control…though anal did have a certain allure. “Hold still woman,” he said calmly. Pulling his hand away, he could hear her sigh, but as he stepped to the dresser, he picked up a bit of lube, and a small, short ‘bat,’ that is, a very short miniature riding crop. Placing them on the bed, Jono also grabbed his old friend, the Hitachi.
Turning to Sherry, Jono then said, “Woman, we are going to use something called ‘confusion’ in order to remove that first real boundary.” And flipped the Hitachi on. Setting it down, he saw her watching him wide-eyed, as he applied some lube to the finger, which he then worked back to her butt hole. Seeing her distress, he placed no pressure on it. Rather, he used the Hitachi to carefully engage Sherry’s clit. In moments, the hum of the Hitachi had a distinct ‘wet’ sound, as Sherry began to breathe deep again. “Move those hips, woman.” He said, and it took no urging for Sherry to begin to do that very thing, Jono keeping the finger just touching her butt hole.
After about a minute, Jono could tell that Sherry was relaxing….and he applied some pressure. Sherry began to tense, so jono upped the use of the Hitachi…then the finger…then the Hitachi.
As Jono moved back and forth, Sherry soon found herself willingly opening her anus to his finger. Oh it still hurt, but the sensation of the Hitachi was what she needed. She found herself alternately moaning and making little grunt/whimper noises. Accepting the inevitable, Sherry found herself trying to open and accommodate jono, rather than fight him
“My new little one likes this, yes?” jono asked, realizing he was now two digits deep in her ass
“Ooh—I-I am t-trying Sir,” Sherry responded. And she really was. The ‘confusion’ of the Hitachi had allowed her to accept him, yet the pain of the finger kept her from orgasm. It was crazy, because normally she would have already had an incredible orgasm by now. It was the restraints, and the changing of her mind. It was happening, & she was fighting it less now. Just as she felt the wave building, a new sensation in her ass snapped her out of it.
Jono found himself over the last digit, so he began to make little tiny circles. As he did, he bent forward, and , moving the Hitachi down to Sherry’s willingly open vagina, covered it, while at the same time he began to use his tongue to flick her clit.
For Sherry, this effect was immediate, as Sherry said “OH-GAH…AHHH>>>” and began digging her heels into the cuffs as she pulled HARD against them. The wave was VERY much building.
Pulling his face and the Hitachi quickly away, Jono told her, “Sherry, you DO NOT CUM until I tell you, got that? YOU ASK.” As he said that, he picked up the small ‘bat’ and gave her pussy a very light ‘tap’ with it…then again.
Sherry was on a roll & just about to release the wave, when Jono changed everything! Her orgasm motor was revved, but a few taps, on her pussy of all places, with that damn swatter or whatever the hell it was, and the wave was broken. “What the hell are you doing to me?” She blurted out.
Jono smiled broadly and simply said, “I control this ass now, and that includes orgasms, so you’d better remember to ask” With that, Jono’s finger began to circle in her ass again, the Hitachi was on her pussy, and Jono was suckling/flicking her clit.
This drove Sherry insane. Her body had totally left her, it seemed to be disconnected, and was totally responding to Jono. She was angry at herself to the point of tears, and yet at the same time trapped in total ecstasy by the person who was Mastering her very body! Shortly she found herself saying “SIR..I need to CUM, I have to..”
But Jono cut her off, repeating that he controlled her. This time, though, the slaps with the small ‘bat had a bit of force to them, and a ‘wet-slap’ sound, that Jono found particularly satisfying.
Jono repeated this process a third time, and it was pretty apparent that Sherry could not take much more. Sherry was crying, sweating, sniveling from her nose, and slamming her head backward into the pillow. She made sniveling noises and her hips were buckling and rolling to their own rhythm. Quickly, Jono slipped his finger out of her ass and, as he lifted the Hitachi, he slid his dick into the hottest, wettest, most open pussy he had felt in a long time.
As he did this, he shifted the Hitachi up to Sherry’s clit and said “CUM WOMAN, NOW….DO IT!!!” and began to pound hard into her, like at room 13.
Sherry arched her back as the wave, now the size of a building, or so it felt, came rolling out of her. With it came a new flood of her juices she had never even seen before, but she didn’t care, and Sherry screamed like her very soul was being torn out of her. The wave just seemed to last and last, & that was fine with her, as she had literally NEVER experienced something like this. It ran so long she actually was able to fill her lungs and call out some more, but the wildest part? Jono was still pumping away!
As for Jono, knowing full well that her pussy would be very sensitive, showed it, by giving her no break whatsoever. Her legs held out and open, Jono simply placed his arms outside them and, holding a knee in each hand, began tugging her down onto his hard, throbbing cock as he pounded into her with all his might. He started this just after her screams subsided, and he could quickly see that her incredible orgasm had given way to discomfort as he pounded his dick into her soaked, loose pussy. Sherry had soaked him in her juices as well, apparently she was a squirter on some level, but right now he didn’t care either, because the wave was rolling thru him too. Grabbing her thighs and rolling her back slightly to get his dick as far as it could absolutely possibly go, with a groaning, moaning yell, Jono proceeded to empty every bit of his ejaculate into her in a hip-thrusting, pumping frenzy.
After this, they were both pretty spent. “Damn good thing we have a guestroom, the bed is soaked.” Jono told her, as he released her bonds, completely removing her cuffs. Flopping on to the bed beside her, Jono stared at the ceiling, tired, but feeling very confident with himself. And what he had accomplished.
Sherry lay there staring upward as well. She had never been pushed so hard, taken advantage of so much, and enjoyed it as much as she did. She was weak…limp, yet she found herself unable to resist turning and hugging this man that unleashed something in her, partly terrified of what it was
Source: reddit.com/r/Erotica/comments/b8m00i/correct_office_politicsblackmail_training_pt2
Why do i suddenly feel the need for a cigarette after writing that?