Corporate Punishment

Finish Shopping

Sam swallows the lump in his throat and nods. "Yes, it isn't appropriate for a first date. It is too formal for most occasions."

Tiffany reaches into her purse and pulls out her phone, handing it to Sam. "Take a pic for me, please. I want my friends to see it."

Sam takes the phone and as he backs away, he realizes he has been getting hard looking at his crush in this dress. The more he tries to will it down, it seems the harder he gets. For the first time Sam wished he had put on his cage, no the cock cage Macy had ordered him to wear. As he took the pic for Tiffany, he hoped that his erection wasn't showing and that if his pants were tenting, that she wouldn't see. He knew Macy would notice even the smallest hint of an erection. Imagining Macy's reaction only made him harder. He sheepishly hands her back the phone.

"Thanks. Are you feeling ok? You look a little flushed."

Sam mumbles a response.

"Well, if you are sure." She turns around. "Can you help me with the zipper?"

Sam pulls the zipper down to her lower back, imagining that this was the end of his ideal date and his ears rang with the sound of his heartbeat. Lost in thought, Tiffany's voice brought him back to reality.

"That's good enough Sam, I can get the dress off now." She gently places a hand on his chest and pushes him from the dressing room. "No free shows. It isn't like you are one of my girlfriends."

Sam leaves the dressing rooms and waits until Tiffany returns. She hangs up the items she didn't want, including the dress that Sam could barely keep his eyes off of anymore. They pay for the outfit and Tiffany suggests they get a drink before they finish the shopping.

As they sip their coffee, Tiffany holds out her hand. "Unlock and hand over your phone."

"Huh? Why?"

She sighs. "We had a deal, right? You get into an exercise routine and I would see about getting you a date with one of my friends. Well, I can tell you must be doing something, but I need more proof."

Sam bites his bottom lip and nods, unlocking the phone and handing it over to Tiffany, hoping that he had deleted all the pics he had to send Macy. He watches nervously as she taps the phone's screen.

"Ahh, here we are. It looks like you have been trying hard to improve your health. I can see you have been doing some exercise for the last two weeks. Not only does the app for the gym you joined show you checking in, but I can see on the built-in health tracker you were even exercising when you were out of town last week." She hands back his phone. "Just two more weeks, and I'll see if I can get you a date with one of my friends. Now, shall we see about getting me the last few things I need for the date?"

Sam feels his face burn bright red as he knows she is talking about underwear. "Can I just give you money and you can buy them?"

Tiffany places her hand on his. "Sam, I put on that dress we both knew wouldn't be right for a first date. Is it too much for me to ask for you to accompany me in the lingerie store just to pick up a bra and some panties?"

Sam feels goosebumps on his arm and the crotch of his pants tightening. "No, it isn't too much. I can go to the store with you."

Tiffany watches Sam carefully, smiling as he looks at the floor and wondering how much more she can push him. She takes his hand. "Come, this will be a quick stop. I still need to make sure I have time to get ready."

Sam follows her hand-in-hand to the lingerie store. Just outside, she releases his hand and by momentum he follows her in, burying his hands in his pockets.

Tiffany feels a little sorry for Sam as she sees how nervous he is as they walk through the store. She knew exactly what she was looking for, and roughly where it was at in the store, but she picked a couple sets for him to give his opinion about. One was just the wrong color, another was too lacy. By the time they got to the set that she actually wanted, he had relaxed, though his blushing never went away.

As Sam and Tiffany went to the register, the women behind the counter looked at them and smiled. She told Tiffany the price and only barely looked surprised when Sam pulled out his wallet and swiped his card.

Outside the store, Tiffany thanked him for helping her shop and Sam thanked her for the advice. Sam sat in his car for a few minutes, wondering if he should go home or go to the gym. Eventually, he realized that if he didn't go to the gym, he probably wouldn't leave his apartment for the rest of the day.