Corporate Punishment

Tiffany's friendship grows

"Sam, I know that this may be presumptuous, but if you need more help shopping, I'm sure we can come up with some sort of mutual agreement." Several things ran through Sam's mind. He could feel himself both blush and shiver involuntarily as he thought of what he had gone through so far this week. Before he can answer, the phone rings again. "I'll send you a text later to discuss some possibilities." Sam nods numbly and heads off to the elevator. Before the doors close, he can see her looking at him and then he glimpses the shoes he bought her and his cock reacts again.

A few hours later, his phone chimes, and there is a message from Tiffany. It is a pic looking down her legs to her shoes. "I thought I'd send a pic, in case you didn't get to see them earlier."

Tiffany - "Just to be more transparent. I was thinking, shoes/clothes. Nothing else."

Sam - "I wasn't sure what you had in mind."

Tiffany - "mm hmm. ;P Sure. Well, if you ever want more help with shopping, just let me know. :)"

Sam - "Not this paycheck, but maybe the next one." He scrolled back up to the pic of the shoes and felt his cock twitch and strain against the cage. 'No. I can't think about her like that. Besides, I need to get back to work'

At lunch, Sam sits down at an empty table and eats while flipping through his phone. He notices someone sitting down beside him and looks up to see Tiffany. "May I join you Sam?"

"Sure, but I can't say that I'll be great company."

"That's OK." She pulls out her phone and scrolls through it as she eats her sushi. At first, she lightly taps his shin a few times. "Oh, sorry about that."

"Huh? It's fine."

His body stiffens as her shoe presses against his leg, but this time it slowly slides up and then down once before being removed. Sam tried not to look at her, but he thought he saw a brief curl of her lips out of the corner of his eye. "Oops." She crosses her legs the other way.

Sam's mind is racing. She couldn't be interested in him. He was just too average. His phone chimes and sees a message from his boss on WhatsApp. He excuses himself quickly and rushes off to his desk, then the restroom. She told him he needed to provide a new proof pic within five minutes. He got it sent off with a few seconds to spare and hoped she didn't make any comments about it. He could see the wet spot that the pre-cum had made in his undies and in the pic you could tell that he was straining against the cage a little.

It was over an hour later that he got a response. "Well, it seems like something got you a... little... excited." Ugh, why did he throb when she implied he had a small cock? The rest of the day goes by quietly. When he gets home removes the cage and masturbates furiously.

He did wake Saturday with several texts on his phone from Tiffany. She and some friends went out to a club, had a bit to drink, and was drunk texting him. It started with a few texts, wondering where he was. They got more insistent that he was late in meeting them and that they were going to go to another club. Next was a pic of Tiffany and two of her friends just outside the entrance to a club. He paused on the pic and looked at the normally unassuming receptionist and her friends. The low cut, fitted outfits sort of shocked him. She and her friends were out to be seen. The last one was about 2:30 in the morning saying that he was missed and that they had a great time without him. Sam wasn't sure who the texts were for, but he knew they weren't for him. He spent his weekend watching porn, masturbating, and avoiding the cage as much as possible.