Panties and His New Boss

After the knock on his hotel room door which surprised Bill, he opened the door and found Mrs. MacGregor standing there. He was a little surprised to her. "oh, hi, Mrs. M. I thought we were meeting at the other hotel and walking to dinner as a group." Bill was on a trip with a few co-workers he'd been interning with. He was a late addition to the business trip and Mrs. Macgregor was head of the department. Jane MacGregor was a lot older than Bill. She was probably 50 but she was pretty high up in the company and head of their whole department. Bill was really pleased when she noticed him left off a list of people to go on the trip and pulled him aside after a meeting. He was such a late addition that Mrs. Macgregor's assistant couldn't get him in the same hotel as the conference with most of the rest of the people but she got him at another nice hotel nearby.

Mrs.MacGregor came in without waiting to be invited and sat on one of the beds. "Yes we are Bill but I wanted to make sure you were enjoying the conference and apologize for sending you over here. We'll walk to the restaurant together and meet everyone else. Do you like the hotel?"

"Yes, ma'am. Thank you so much for bringing me. I guess I didn't expect to go and it was super nice to bring me. I don't mind being here. It's a real nice hotel so I'm not complaining at all."

Jane liked the new kid. He had the right attitude. He was hard-working, did everything he could to help on everything, never complained, and recognized authority. Not everyone did these days although Jane MacGregor never had a problem weeding those people out. But she was glad Bill appreciated it. "I'm glad you like it Bill. Everyone likes to be on the conference site but I actually like some distance sometimes. And this is a great hotel. I'm staying here myself but please don't let any of our staff know."

Bill felt very comfortable and decided he liked his boss even if she had a reputation in the company for being tough. She was actually pretty nice. He was looking forward to dinner. He got in late the night before and hadn't seen anyone or done anything. Just stopped at a store, bought a few things, and spent the night in his room by himself. Today's meeting and tonight's dinner were the start.

Mrs. MacGregor used his bathroom and he finished putting on his tie so they could just go.

Mrs. M came out and looked at him funny. "Bill, are you staying here alone?"

"What? Of course I am, why?"

Mrs. Macgregor looked seriously at him and held up a pair of black silk panties. "Whose are these? Someone else here or are you screwing around instead of working and someone left them?"

Bill turned very red and was mad at himself. He was really pissed. This was going to be embarrassing.

"No, ma'am. They're mine. I mean not mine but they aren't anyone's. I haven't seen anyone or anything. I just didn't clean up and they were just you know I mean I was going to get rid of them and I didn't think anyone would stop by or anything." Bill was rambling and scared and embarrassed and having trouble.

Jane MacGregor wasn't mad but she was amused. She didn't want to completely embarrass Bill but this would be more fun if she stayed serious. "Bill, it's okay. But be honest with me, okay? Bill, do you wear women's clothes? You aren't wearing any right now are you?"

"Shit no!" Bill reacted violently then stopped. "I'm sorry but no, nothing like that. I'm not a whatever. I just I mean this is embarrassing but I just, um, was walking last night and I got some food and a couple things at that department store. Just some beer and I needed a razor and a snack and I saw these and you know. I mean I was alone in a hotel and kind of used them to...oh damn you think I'm a total perv and you're going to fire me but I swear. This is so embarrassing."

Jane smiled. She was relaxed and loved the younger man's embarrassment. So she held the panties up by one finger and swung them. "Bill, calm down. So you're not cheating on a girlfriend or buying hookers then." Bill turned red but didn't speak. She continued, "So my star intern gets to a new city and buys cheap silk panties so he can masturbate himself to sleep at a hotel. That's a pretty picture."

Bill buried his head in his hands and mumbled "I'm not doing anything. I don't even have a girlfriend. I was just I don't know. It was stupid and I shouldn't. Please don't fire me I mean really please."

Jane knew she could be a bitch and domineering and tough but she did feel bad for the young man. She was having fun too. She could be compassionate and a little sadistic at the same time. "Bill, really. I'm not going to fire you. I know that men masturbate. Women too. You like pretty things. I'm sorry I'm kidding. But I'm not going to fire you over a pair of panties. Besides we need to go. But I do want you to learn a lesson. Think of this as part of your training to be a future business leader.You need to be discreet. And in business you never know when someone may drop by. It pays a business leader to keep a clean room in case because you never know when your boss might come in." She smiled to put him at ease a little.

He got up and felt better but she stopped him. "Bill, I want you to remember the lesson about being prepared. So I need you to do something. Take the panties back in the bathroom and put them on under your suit pants. The unusual feel will remind you. No one else will know anything but you will be reminded about the importance of being careful. Don't look at me that way. Do it. Right now." The force of her personality made people react very quickly when she forceful and Bill acted faster than most people.

When he came out he was embarrassed but Mrs. M opened the door and started walking down the hall before he could say anything. They walked out of the hotel and down the street a few blocks. Mrs. M talked the whole time about business, the conference, and their co-workers. She ignored what had just happened and Bill wasn't sure what was up. It was weird. He was wearing the panties under his clothes which felt perverted but kinky. But everything else was normal and Mrs. M was definitely very normal. It muct be some weird punishment.

When they got to the restaurant, she stopped and took out her phone and waved for him to go in. He found the group had a private room and was mostly there. He took a seat toward one end of a table. It was the only open seat except the head of the table at the other end. There were ten and most of them knew each other but they were friendly. He was younger but not a lot younger than all of them. Mrs. McGregor showed up fifteen minutes later.

Mrs. MacGregor sat down at the other end and people were a little quieter for a few minutes but then it got better. The guy next to Bill had had a few drinks and by the end of dinner was a little drunk. "Let me tell you something kid." Bill hated being called kid but the guy was drunk. "Let me tell you kid, it's a good company. You should hope they hire you for a regular job. But watch out for that one." He pointed at Mrs. MacGregor. She's a ball buster. She's good and usually fair but came down hard on me once for nothing. Don't cross her or she'll cut off your balls and keep them in a jar on her desk."

Bill didn't know what to say so he just thank you and the guy walked off to the bathroom. The woman on Bill's other side leaned in after the guy left and said quietly, "Ignore Johnson. He's bitter about losing a promotion three year ago and he can't handle working for a woman. He's a caveman." She was leaning in and Bill liked her perfume. He was intimidated a little by everyone but this woman made him feel more at ease. She was the assistant head of the department, the number two person at the table and she was being nice to him.

"Thanks, ma'am. I just figured he's drunk or something. Mrs. Macgregor seems really smart and has been fair."

She patted Bill's knee and said, "call me Gretchen not ma'am. We're co-workers. I think Jane likes you and if it goes well we might put you on staff at the end of the month. I hope so." She smiled at him and then got up from the table. People were starting to go.

One group got a cab and a smaller group was walking back to the hotel where the conference was. Bill was going to join them even though it was the other direction just to be social and get to know people better. But Gretchen pulled him aside and asked him to wait for Mrs. Macgregor so she didn't walk alone. He spent a few minutes just waiting for her and looking around the restaurant. He was admiring the very attractive hostess and thought he was subtle about it when he heard a voice behind him.

"Do you like what you see, Bill?" Mrs. Macgregor asked him.

He turned red and started to stutter and felt crappy for being caught. But then she started laughing at him, "Sweetie, you're too easy. I'm just giving you a hard time. Don't get your panties in a bunch." Then she laughed again and he turned redder. She was clearly enjoying herself and she reached down and playfully squeezed his behind. "That's right, my newest staffer is wearing his pretty panties under his manly suit," she whispered. "Don't worry, I won't tell the hostess unless you think she'd be interested in that kind of thing."

Mrs. Macgregor was having fun but she noticed how embarrassed Bill was getting. She enjoyed making him uncomfortable and was happy to assert her authority but she didn't want to push the young man too far. She liked him and planned on keeping him around so she backed off just a little. "Oh, don't worry, Bill, I'm just teasing you. Come on, let's walk back to my hotel."

On the way back they walked slowly and Mrs. M told Bill about the company and what a good place to work it was. She expected a lot of people but if they delivered they were rewarded. "Bill, most of the department has been with me since I took over or just after. I find the right talent and I take it whether it's in another department or not. We're a tight group and loyal to each other. Gretchen has been mine for six years now. She's the longest but we've built the rest and I think you noticed at dinner that we're a good mix. You're a good intern and maybe more."

Bill knew this was good and he was excited. "Yes, ma'am. I can tell what a great unit you have and I'm honored to be part of it. I like the people and I'll do anything I can to help and be part of a team."

As they walked into the hotel and across the lobby, Mrs. M said quietly but firmly "I hope you understand that this is my team. We work together but there is no question who is boss. Someone has to be in charge and in this operation there are no questions about that. You can take direction and you are and will be obedient." She said it not as a question but a statement.

In the lobby before they got in the elevator, Mrs. M took a tissue from her purse. "I think my shoes are smudged and a little dirty from the walk through city streets. Fix that for me, dear."

As she handed him the tissue, he didn't ask questions. He felt this was a test and so he kneeled down, ignoring everyone else in the lobby and thinking only of his boss. She looked down on him as he wiped and polished with the tissue until she lifted one knee to get his attention, nodded, and said thank you.

He got up and they got in the elevator and went to his floor. Maybe it was her floor too. Bill didn't know. He went to his room and she came along talking about business issues. She went in as he held the door, walked to the window and then turned as he approached. "let me see your panties Bill."

He stopped. He was about to ask a question but he knew he shouldn't so as puzzled as he was he simply obeyed. He removed his shoes and his pants. She pointed to a hanger and he hung the pants up. "The jacket too. We must take care of our clothes." So he hung the suit's jacket too. Then he stood there in socks, panties, a shirt and tie.

She looked at him up and down, evaluating. Then she approached and walked around him. She ran a hand over each butt cheek and said, "tight. That's good."

She didn't know if she meant his shape or the panties which fit tightly back there.

She walked closer. She whispered into his ear. "Bill, dear, you've gone soft. Maybe the hostess at the restaurant didn't excite you or maybe you forgot her and I'm boring you. Maybe you don't find standing in front of your boss, a woman who could fire you tomorrow, standing in your panties at all exciting or maybe you're nervous and so you're soft."

The more she talked the more the blood flowed below his waist and he started to get harder. She stepped back and looked and then stepped forward and started undoing his tie. "It's getting better but let's get this thing out of the way." She threw the tie on the bed and then unbuttoned his shirt moving it so the bottom of it didn't block her view. She looked and then slowly ran one fingernail across the front of the panties the whole length of his manhood as it filled and strained the panties. She looked at him and smiled.

He felt very strange but very excited. Mrs. Macgregor slowly stroked his bulge like it was a pet and then took out her phone. She smiled and pushed an automatic number while touching the panties and their contents with her other hand. "Hi Gretchen. Yes, what time is our morning client meeting tomorrow? No, 11 is just fine, I don't have my schedule in front of me. I want you to bring that new intern with you. Yes, Bill, that's right. Make that happen. Thank you." and with that she hung up.

She gave his now throbbing bulge a squeeze and then looked at his phone on the table nearby. In a minute it rang. She nodded and he answered. As soon as he said hello she started squeezing and pulling more making it hard for him to concentrate.

He said hello and then "oh hello, Ma'am. I'm sorry, I mean hello Gretchen. Tomorrow yes. Where should I meet you at 11? Okay. What's that? Oh, lunch?" He looked at Mrs. M who nodded so he said "Yes, I can have lunch, thank you. Okay, good night."

As hung up, Mrs. Macgregor said "this is also a lesson, Bill. Concentration is very important. You had to concentrate on Gretchen even though your body was screaming at you while I did this." She was squeezing the panties around his throbbing bulge knowing he had trouble on the phone. Squeezing expertly, she said "Look at me. Keep looking. Now cum. Cum now in your pretty silk panties."

He wanted to obey and his body desperately wanted to obey so he just let go, staring into her eyes and making a gooey mess in the panties. As he did it, she released him, took a few steps back and with a pleased look stared at the mess they made. She wiped her hand on the bedspread and said "Have a good night, Bill, Lots of work to do tomorrow." The she walked out.