His hand hoovered for a second. The implications were obvious, the coercion - implied. He didn’t have to play along with this. He looked at the other camera again - Mollie was as beautiful as ever, plump and delicious and with a plug up her bum. That was her choice. And this was his.
Jake typed 2 and pressed enter. The prompt flashed a brief confirmation message and faded away. For several seconds nothing happened. Mollie continued working as usual. No message was thrust in his face, no camera feeds lit up to call for his attention. Then his girlfriend took out her phone from her pocket, looked at it with a strange expression, then got up and left her desk.
He caught a few glimpses of her across several feeds as she made her way around the office building. An escalator door closed behind her as it went up, and then he lost track of her.
The camera showing the two sex toys was suddenly picked up and moved to the corner of the room, where it was placed with a view towards a large wooden desk. The feed grew larger and larger until it covered the entire screen. Then, there was audio.
There was a knock on the door and a man in a suit entered the frame and stepped to open.
Mollie’s face was already showing tinges of red as she walked into the room. Jake could swear there were beads of sweat glistening on the exposed top of her big breasts.
“Hello, Mollie,” said the man in the suit, “Are you ready to receive that promotion?”
She didn’t dare to look up to him but just nodded, her blush growing by the second. With a single wave of his hand the plump girl walked over to the desc and bent over, placing her hands down and spreading her legs apart. Jake swallowed hard. She was not doing this for the first time.
Her boss came behind her and ran a finger up her thighs and under her skirt. He took a moment, savoring whatever he was doing, before pulling her panties down and lifting her skirt up. It gave Jake clear view of her plump ass and the anal stretcher that had been lodged inside her asshole, pushing it open. The man in the suit grabbed the base of the plug and pulled it out in a slow but decisive motion, stealing a moan from Mollie. Then he unbuckled his belt and pulled down his pants.
In that instant Jake understood what his girlfriend had meant. Tha man had the biggest and thickest dick he had ever seen on a white person. His monstrous cock, already erect and ready for action, looked a good 10 inches long and with a girth that was just as impressive.
Without skipping a beat, the boss placed it against the chubby girl’s bottom and pushed forward. After 3 tries, he stepped back.
“It looks like you need further stretching.”
Jake grounded his teeth. The sly dog was enjoying this. It’s true that he was exceptionally big, much bigger than Jake, but the old man hadn’t even lubed up. He wanted to get his fun with her before things ended.
“Worry not,” the man continued, “I have just the thing to help you. After this I’m sure your ass will be ready.”
He walked around the desk and sat on the chair on the other side, facing Mollie. Then he placed the long bulbous toy on the desk in front of her.
“Put this in,” he ordered.
Jake could not see the glances they exchanged, only his smirk. Slowly, Mollie took the giant toy and placed it on the floor of the room. She hesitated for a moment.
“Here, have this,” her boss said, tossing over a bottle of lube.
She squirted a generous amount on the top of the toy, then smeared it down the bigger spheres with her hands. As she was presently facing the camera, Jake could see her biting her lip as she coated the largest ones carefully.
When she was done, she squatted over the toy and pressed the tip to her asshole. The first sphere was small and went in easily, followed by the second and the third. Her butt swallowed the fourth greedily, showing the results of the last two days of stretching. The fifth, however, was a challenge.
Mollie began visibly straining, bouncing up and down as she tried to push the toy deeper into her ass. She would gain some ground only to have it slip out again, despite her best efforts.
“It’s- it’s too big, I can’t!” she complained.
“You can,” replied the boss. “You need to learn how to relax your ass. Then it will accept it in.”
“I’m trying…” she wailed, puffing to got it in. It was the final sphere, and the biggest of the bunch. Jake was surprised she had managed to get this far so quickly. But this one was really a challenge.
Part of him wanted her to fail. It was too big for her. She should just admit defeat and get this whole thing over with. Perhaps that’s why he’d chosen number 2.
The other part of him was edging in his seat with a raging boner. Seeing his chubby girlfriend try to stuff the enormous toy in her plump butt was a treat to behold. An absolute delight. It felt like retribution for the fact that she had agreed to sleep with her boss in the first place. Jake’s built up frustration was turning into vindication. He licked his lips.
“Girl, do you want this promotion or not?” came her boss’ voice from the desk.
“I’m doing what I can…”
“Yes or no, Mollie!” his voice cut.
“Yes, sir..” she whimpered.
“Good. You know, there is a knack to getting your ass to relax and stretch.”
“There is?”
“Yes. It has to do with arousal. The more aroused you are, the more your muscles relax and are willing to allow things to enter you. Don’t they teach girls anything these days?”
“I- I didn’t know..”
He chuckled.
“Such a naive girl you are, Mollie. It will be fun to train you. Go on now, touch yourself. You’ve wanted to for a while.”
Her hand slowly moved down towards her pussy. The blush on her face was going redder by the second, but she went on anyways, beginning to rub her sweet spot.
“That’s it, let the pleasure take you, ease yourself into it…”
She was rocking back and forth now, kneeling on the floor with one hand rubbing her pussy and the other easing the giant toy into her bum. It was a precarious position and she began to tip to the side, the light-headedness of the arousal coupled with the necessary motions making it hard to keep her balance.
Mollie’s boss rose from his desk and walked to her, grasping a fistful of hair from the top of her head. It pulled her back up and gave her a point of stability that stopped her wobbling. Then he squeezed her jaw with his other hand and forced her face up to him.
“Enjoy stretching your bum for money, whore?”
She was frozen for a moment, visibly unprepared for this turn of events. He slapped her face.
“I didn’t say you could stop touching yourself, slut.”
Jake could see the moment’s hesitation, her pride and lust battling each other as the plump girl’s expressions shifted in the span of a few seconds. Then she bit her lip and her fingers started moving again.
“Good girl.”
Her boss reached down her big cleavage and pulled her tits out, one after the other. They looked especially big, pushed up by her bra. She looked up longingly. Her nipples were already hard and erect. The opportunity was ripe. The man in the suit pulled out his cock and let it hang half erect in front of her lips.Mollie opened her mouth and took it in, allowing her movements to be guided back and forth by the hand grasping her hair.
Jake realized he had begun stroking his cock. Maybe he was going to feel conflicted about this later, but right now he couldn’t help himself.
As Mollie sucked more and more passionately, it seemed that the toy was finally starting to sink in. The final sphere was halfway up her round butt, the largest section almost swallowed by her asshole. Only a little bit was left now…
“Push it in, slut!” he ordered.
The girl on her knees moaned, rubbing her clit faster and faster, then pushed down with her entire weight.
Her asshole stretched, opened, and swallowed the billiard ball sized sphere into her butt, leaving just the flat base outside.
Her head was pushed forward, swallowing the fat dick all the way to the balls. She moaned, then started to swallow.
There was a moment of stillness, then Mollie’s boss pulled, letting a thin stream of drool and cum drip down onto her hanging breasts.
“Tidy yourself and get back to work, slut,” he ordered, returning to his desk.
It took her a moment to get back to her senses and a few more to pull up her panties, get to her feet, clean her tits with a napkin and put them back in her dress. By the end of all that Mollie was back, looking almost normal, save for her unusually round butt and the odd way she walked about.
“This should stretch you enough this time. Make sure to keep it in until next time we meet. Now get out of here.”
She waddled out of the room, red as an oyster.
Jake closed the camera feed and exhaled heavily. That had been some show. He didn’t know what to think or how to feel.