As soon as she came home, he knew that something was up. Mollie had a look in her eye, something Jake could only guess as general anxiety, though there was also a weird sheen of excitement to her. She put down her bags without saying a word, then went into the living room, collapsing on the sofa. He followed, sitting next to her.
“My boss called me in for a one to one talk after work,” she said. “He made it clear that I can have a big promotion, almost twice what I’m currently earning…. if I sleep with him.”
There was a heavy silence that hung in the air. Stupefied, Jake stared blankly at his girlfriend for a few moments. Mollie was a short, chubby girl with big round tits and a plump ass. She was not the office hot bomb to turn heads around, but was certainly a snack for the right kind of man. Which apparently included her boss.
“What did you tell him?” he finally asked.
“I haven’t told him anything yet. I wanted to talk to you first.”
Jake considered this. It was a lot of money. But even more so than that, he was getting a little turned on thinking about it. He had always wanted to explore the sharing options with his girlfriend, though she had been mostly conservative about it. This was the perfect opportunity.
“This can really help us out a lot…” he pondered out loud. “I guess, as long as it’s a one time thing…”
Mollie bit her lip. Her face was still anxious, but that anxiety was mixed with excitement. Jake could tell she was hiding a few dirty thoughts of her own.
“If you’re OK with it… I’ll do it tomorrow.”
He nodded, then leaned over and kissed her. Their embrace extended into sloppy tongue play, until his hand slithered down under her skirt. She was already soaking wet. He removed her panties and pushed her back on the couch.
The next morning Mollie got up earlier than usual. She spent some time in the bathroom, then put on a revealing top with lots of cleavage showing her fat boobs. She put on more makeup than usual and finished with a bright red lipstick. As soon as she closed the door behind, Jake began furiously jacking off.
The day rolled by without any messages from her. Her shift ended and the usual time she came home rolled by without any news. Jake had expected this, but it was only now that the reality of it was starting to hit him. His heart pounded as the minutes rolled by. Half an hour passed. Then another ten minutes. How long could this take? Another five minutes. He was pacing the apartment.
An hour later than usual, Mollie finally came home.
“What happened?” he asked.
She remained silent. In the first instant Jake thought she looked just the way she’d left. But then there were subtle hints. Her messed up hair. Her wrinkled skirt. The slightly smeared lipstick.
“It didn’t fit,” she finally mumbled.
“What do you mean, it didn’t fit?”
Mollie took her shoes off and headed towards the bathroom to remove her makeup. As she went past Jake he noticed an unusual swaying of her hips. Two and two were starting to make four.
“He wanted your ass?”
“It’s a lot of money Jake,” she replied. “And you didn’t seem to mind yesterday.”
“Yesterday you didn’t mention it was your ass!”
“My pussy or my ass, what difference does it make? I’m gonna get fucked by my boss either way.”
He clenched his fist. Anal was one of the things he’d always wanted to try, but Mollie had turned him down each time. To have her first time be with her boss… Jake took a deep breath.
“Whatever, I guess. So now what, you won’t get the promotion?”
“We- we’re going to try again tomorrow,” she mumbled. There was that odd swaying of her hips again that drew his attention. Was that…?
He grabbed her ass and felt something hard in her butt. Mollie squealed and jumped back.
“Are you wearing a butt plug?!”
‘I… I had no choice! He is too thick, unless I stretch a little he’ll never fit inside me…”
Before Jake could figure out what to say, Mollie ran away and locked herself in the bathroom. He decided to let her be for the moment.
The night was awkward, with Mollie turning and twisting most of the time. Jake could feel that she was sleeping lightly, fluctuating on the edge between wakefulness and dream. She moaned occasionally, her ass tightening around the butt plug, then relaxing again. The process repeated for hours, until eventually Jake himself drifted off into an uneasy sleep, filled with dirty images of the busty girl.
When he woke up on the next morning Mollie had already left for work. He sighed and got on with his own tasks. Unlike his girlfriend, Jake was working from home, coding for an overseas company. It paid well enough and meant that if he was feeling lazy, he didn’t even have to get out of his pyjamas. Today was no exception.
Lunch passed and afternoon came and went with his nose still stuck on the screen. As the sun set behind the glass buildings and Mollie’s shift approached its end, he started getting distracted. His mind drifted to images of her plump ass tightening around the plug. By now, she had spent almost an entire 24 hours with it. She was going to be nice and stretched for her boss to have his way and fuck her butt. The thought was weirdly arousing. Perhaps after this Jake would finally manage to convince her to have some fun with him too? It was important to look things on the bright side.
An hour later than usual, Mollie arrived home. Her expression was unreadable and she quietly left her bag and headed to take a shower. Thirty minutes later and fully clothed, she joined him in the living room. When she sat on the couch, there was a flash of something over her face, just briefly before she managed to regain composure. Jake raised an eyebrow.
“It still didn’t fit,” she simply replied.
“What, again? But you wore a plug for an entire day! How thick can this guy be?!”
She didn’t offer a comment.
“What happened exactly?”
“I told you, Jake. He called me in his office. We tried again. It didn’t fit.”
She looked away, blushing. “He gave me a bigger one.”
“Why not? Are you my girlfriend or his? I wanna see what he’s done to you!”
Reluctantly, she got up, pulled her panties down and bend over. Her plump cheeks were hungrily wrapped around a black anal stretcher the size of a 50 cent coin. It took Jake all of 3 seconds to get hard as a rock.
He walked over to her and ran a finger along her slit. She was already wet and ready. As he started to unzip his pants, Mollie abruptly rose up and pulled away.
“We can’t,” she whimpered.
“Why the fuck not?”
She was still facing away, not daring to look at him.
“He said… he said that I owe him a debt. And I shouldn’t do it with anyone else until I pay up. Otherwise he won’t give me the promotion.”
“This is ridiculous, how the hell would he know?” Jake grabbed her by the shoulder and flung her around. She had a weird expression on her face, with a hazy, almost lusty look in her eyes.
“I want to Jake, I really want to… but we can’t. Please, wait just a little bit longer, until this is over…”
He gave a frown, then sighed. There was no use pushing it. “Fine,” he said, returning to his computer. Coding would have to distract him for now.
He stayed late that night, lying in bed, facing away from her and browsing the internet with music on his headphones. It was the best he could do to distract himself from her constant turning and shifting, and the way her breath came a little short even in her sleep. Tomorrow it evening it will be over, he thought. Just a little while longer.
Jake woke up late again. He dragged his feet to the kitchen and made a fresh brew of coffee, then dragged his way to his desk. It was almost noon.
When he opened his laptop for work, he noticed a strange e-mail in his inbox. It was from an anonymous sender, but it carried the same domain name as the company Mollie worked at. Inside the message there was only a long, obscure-looking link to an unfamiliar website, followed by an 8-digit code and a wink emoji.
Perplexed, he clicked on the link.
There were a series of loading bars, eventually followed by a security prompt. Without thinking, he entered the code in the e-mail. The confirmation lit up in green, followed by a few other loading bars, until finally he was in.
His screen lit up with a series of camera feeds, like those often seen on the security terminals on movies. It took him a moment to recognize the place, but once he spotted a few key features, there was no mistake. It was Mollie’s office, just as he had seen it on the few occasional visits he’d done. A few seconds later he spotted his girlfriend as well, standing in plain view of a camera conveniently pointing down at her desk. With a few clicks and drags, Jake managed to enlarge this screen until it took up almost half of the available space, reducing the size of the other feeds. The resolution was not bad at all. In fact, he could see her as if she was standing right in front of him.
Mollie had outdone herself that day. She was wearing a corset that pushed her big boobs up, like two ripe melons, and a low cleavage that showed most of them in their full splendor. On top of that she also had a shirt skirt with a crack on side of her thigh, making sure that her plump ass did not go unnoticed. Jake felt a mixture of arousal and confusion.
While he was fixated on watching his dolled-up baby working, another cam feed suddenly drew his attention with a blinking red frame. As he clicked to enlarge it, he saw a close-up of a glass table with two strange objects propped upon it.
The sign appeared without warning, held in front of the camera by a male hand, of which he could only see the fingers, the wrist, and the beginning of a navy blue sleeve with golden buttons. Then the hand flipped the sign on the other side:
“YOU GET TO CHOOSE”
Pulling away from view, jake could see the two objects on the glass table again. The first was a transparent stretcher, similar to the one he had seen Mollie wearing. It was basically a short butt-plug with a wide base that kept the sphincter stretched at all times. This one looked wider than her current one, with a base as thick as an average dick. It was clear that the purpose of the device was to prepare any girl’s willing bottom to accept a hard pounding. Next to the stretcher there was a piece of paper showing “#1”.
The second object was a long silicone toy with a bulbous structure, similar to a series of balls fused together by their ends into a single body. It started with a small tip and the spheres grew progressively larger, with the final one at the base being as big as a billiard ball. Next to it there was a sign showing “#2”.
All of a sudden the screen blinked and a text prompt appeared, flashing in red: