Jessie's Game

Jessie had no idea what was going on, and just stared at the grotesque mannequin on the screen as it spoke. The sexy guy she had taken home had gagged and blindfolded her after stripping her naked, then at least two other men had covered her in a sheet and carried her out to the back of a van which had been parked outside. She had soon realised that there was no point struggling; while the men were careful and had not hurt her at all, they were far too strong to resist.

She had felt herself taken inside a building a while later, and her wrists and ankles had been clipped into padded cuffs straddling a bench so that she was on her front, as if on her hands and knees. When the blindfold was removed she realised with shock that she was positioned in the centre of her own board room table in the meeting room of her office. She was strapped to some sort of machine, with her torso resting on the padded bench, her arms and legs down to each side held to the frame. There was a large black dildo on the end of a pole, pointed right at her face. Jessie had tried to call out as she heard the man leave by the main door and lock it behind him, but then her presentation screen powered up to show this weird ventriloquist’s dummy.

‘Hello Jessie,’ the dummy said in a gravelly, distorted voice. ‘I want to play a game.’

Jessie tested the straps on her wrists and ankles, but couldn’t free herself. She shouted at the screen. ‘What the fuck is going on here?’ she demanded.

‘The rules are simple. In front of you, at the base of the dildo is a button which you can press with your chin. Behind you is another button, which you can press with your bottom. At your right hand is a switch which will bring the buttons closer to you, and your clothes are on the chair at the head of the table. If you can press both buttons simultaneously, your restraints will unclip and you are free to go. If not, you will have to wait until somebody else can free you.

Jessie’s mind was swimming, she felt a little faint.

The voice continued. ‘You like to impress people, and you also like to embarrass people. So you have a choice to make. In ten minutes I’ve arranged a video conference with all of the other branches of the company from around the world. When the meeting starts, you can do one of two things. You can see how impressed they are when you announce that you have secured a generous donation from a private supporter whereupon I will transfer a very large sum to your company’s account. Or, you can see how shocked and embarrassed they are when they see you as you are now.’

Jessie looked around, wide eyed and panicking now as the dummy paused.

‘Enjoy your game,’ it said, and the video screen changed to show Jessie, naked and strapped to this frame on the table in a variety of angles. The cameras for each chair in the meeting room now showed her: her face in one, green eyes no longer tired but alert and stressed, with her blonde hair tumbling down to her bare shoulders. A view of her torso from the side, her large breasts squashed against the padded bench. A shot of her bottom, legs apart and with her ass and pussy in full view. A side view, showing her naked, straddling this machine with the big dildo about six inches from her face, another about six inches from her bottom.

A timer appeared on the screen, counting down from ten minutes. At the same time a wheel below Jessie started to turn, and the poles holding the two dildos, one pointed at her mouth, one at her ass began to move, pushing the phalluses forward then back in a repeating pattern. She found the switch and pressed it, and both dildos slowly began to move toward her.

She flicked the switch again and the dildos halted, still moving forward and back rhythmically. So this is the game, she thought: One from behind, one down her throat, and if she took them all the way she could press the buttons and escape. She screamed for somebody to help her get out of this.

The timer showed 08:01 by the time Jessie decided that calling for help was futile. With offices all over the world there was no way to know what time this meeting would be – sometimes they were in local office hours, sometimes in the middle of the night. But she had taken that guy home at about 3am, so it could be around 5 now? Probably too early for anybody else to be here.

She thought about the machine, and this game she was being forced to play. Would it really be that difficult to take these dildos? She only had to press the buttons, not hold them down for ages.

The switch let her advance or retract the two dildos, and she flicked it again, watching on the screen as they both moved toward her.

The one behind her was slightly closer and she felt the rhythmic movement as it prodded against her asshole. It left a blob of cold lube between her buttocks; whoever had smeared it in jelly had been kind to her, at least. Flicking the switch again she stopped it advancing and tried to move her hips so it pressed against her pussy instead, but she didn’t have that range of movement. So it was to go up her bum. She used the switch to move it again, and felt it push harder against her ring with each forward motion. It didn’t feel too bad, Jessie thought. She could totally do this.

As the dildo just pushed inside her ass, then back out, then back in, the other began to press urgently against her lips. Jessie opened her mouth to let it in as she took the other further inside. It was hurting now as the rubbery shaft spread her ass open, and the rocking back and forth did not slow. She looked at the screen, at her bottom with this big black shape with the tip starting to disappear up her. Then she looked at her own face, mouth open wide with the black dildo pushing between her lips. She used her tongue to lick it, and tried to generate enough spit to coat it.

Using the switch again, Jessie fucked her own ass more deeply. Although it hurt, it did feel weirdly good at the same time. She felt more… full, somehow, than she ever had experienced from normal sex. Nobody had ever fucked her up the bum before, and she wasn’t entirely sure whether she might try it again or not. She glanced at the timer: 06:24. She was going to need to speed this up.

Whilst Jessie was sort okay with the dildo up her bum, the one in her mouth was more difficult. She was going to need to take it right down her throat, and she just couldn’t imagine how that was possible. Her jaw already ached from accommodating it and spit was dribbling down her chin into a puddle below.

At six minutes remaining, Jessie heard the rotating wheel speed up, and so did the forward and backward movement of the two dildos. Her arse was pretty well lubricated by now, and that one was actually starting to feel pretty good. She felt a warm, tingling fullness spreading throughout her midsection and looked at the screen to see the image of her bottom. She stared, mesmerised by the black shape pumping in and out of her, and saw that her pussy was wet and engorged. She started to think that she might cum from this soon.

She snapped herself out of her trance, watching herself get fucked like this and tried to focus on what she needed to do. Come on, Jessie, she mentally encouraged herself. You can do this! All she needed to do was to take this all the way and press those buttons. It would be over in no time.

She flicked the switch again.