Corporate Punishment

Date Prep

Monday Sam walks in the office and notices that someone other than Tiffany was at the front desk. He stops by Macy's office and drops the key on her desk. At his desk, he sends Tiffany a message that he hopes she is well.

His week is frustratingly uneventful, though he thought Macy was teasing him a bit more, and he caught her several times looking at his crotch. Each time he caught her, his cock swelled in its prison and he became more conscious of others and if they were looking there too.

Friday Sam is eating lunch in the break room when Tiffany sits beside him. She was obviously uncomfortable. "So. Um. Yeah. Hi Sam."

"Hello, are you doing OK? I noticed you were out on Monday."

"Yeah. I'm fine. Look, I don't have long. Can I see your phone?" Before he can answer she reaches over and picks it up and presses the power button. Seeing the lock screen she hands it back. "Unlock it please."

A bit dumbfounded, Sam unlocks the phone and hands it back to her. She taps the screen several times and nods. "Thanks Sam." She gets up and leaves the room leaving Sam confused.

That evening Sam gets a text from Tiffany. "I see you have been keeping up with your exercise. As I promised I will set you up on a date with one of my friends. Can I come over tomorrow to make sure you have something decent to wear?"

Sam hopes that when they are alone that he can find out why Tiffany is acting so oddly. "Sure I'm free after 10. Here is my address." Sam attaches a link to his address and sends the response. He spends the night doing a quick clean and a couple loads of laundry.

He gets up on Saturday and after breakfast takes a shower and makes sure that things look mostly presentable. About 11:00 he gets a text from Tiffany saying that she is on her way and will be there in about half an hour.

Sam distractedly plays games until there is a knock on his door. Tiffany seems to be all business. Sam offers her a drink that she refuses and they head to his bedroom.

"Sam, to be honest with you I didn't think you would make it the full four weeks. But true to my word I'll see about getting you a date with one of my friends. You really aren't the type most of them would be interested in, but I have one that I don't hang out with much which I think maybe have some things in common with you." She opens the closet and starts leafing through his shirts and dress pants. "No. Nothing here." She spies his dresser and before Sam can say anything is opening the bottom drawer. After a few attempts she finds a pair of jeans and throws them on the bed. "I guess these will work." She looks back at Sam. "So I guess it is only a shirt we would need to find for you." She pulls out her phone and starts tapping on it. "Ok, looks like we don't need to go to the mall. There is a closer store that should do." She thinks for a moment. "Wait, show me the socks and shoes you would wear."

Not completely thinking, Sam opens his sock drawer and rummages around for a minute, the cage getting covered and uncovered a few times. Once he finds the pair of socks, he turns to Tiffany who is slightly flushed, with a smirk on her face. "Here are the socks, and those are the shoes over there."

She looks over to the shoes and nods. "Yes, both will work. Let's go find you a shirt"

Sam follows her to a strip mall, and they park in front of a consignment shop. "If our luck holds out, we can find something here, if not then we will have to look in a few more stores." As they enter Sam thinks Tiffany is a bit more relaxed. The sheer number of random shirts amazes Sam, but doesn't seem to phase Tiffany. As they walk down the aisle, Tiffany grabs several shirts and hands them to Sam. Once he is holding about a dozen, she leads him to the dressing room. "Go in there and try them on. If you think it looks ok, then step out so that I can see it."

Sam goes into the changing room and tries on the shirts, only nixing three of them because of fit or the feel of the fabric. Tiffany appraises each of the shirts he models for her and makes two piles. When he was done, she points to the two piles. "This pile doesn't look all that good on you, for various reasons. This other pile is acceptable. You can take your pick from them, but my personal suggestion is this one."

Sam does some quick calculations for the four shirts in the pile. "I'll buy all of them and make a final decision closer to when I have the date."

"If you have a date. I can make a suggestion to her, but I can't guarantee that she will agree."

Sam nods. Sam buys the shirts and they head to their cars.

"Look, Sam, I know I have been distant. It is just that I'm used to my friends pulling pranks like that, but when they sent it to you it really freaked me out. Then when I saw you had actually deleted the pic and the text I got really nervous. It is a pic of me in a very vulnerable position and I don't like anything like that getting out."

"I can't say that I have had any friends that have taken such revealing pics of me, but I know how it is to have pics that reveal a side of you that you don't want others to see. As someone that I consider to be a friend I would want to protect that secret."

Tiffany walks close to him. "Look here, money bag, Don't start thinking too highly of yourself."

Sam can feel himself flush and his cock swells, wondering why his body was reacting like that to Tiffany.

Tiffany takes a half-step back. "I'll get in touch with my friend this week. If she agrees, I'll give her your phone number."

"And if she doesn't agree?"

Tiffany looks Sam over before turning around, getting in her car and leaving.

"Fuck. What is wrong with me? I know she is hot, but first she treats me like a friend, no more like a brother. Then when she thinks I'm trying to hold something over her, she ignores me. Now she is being a bit of a bitch and it is turning me on more than before." Sam shakes his head to clear it. "No. It isn't because of her attitude. It is just that last night's orgasm was so good that my hormones are raging."