Caught Wearing a Bra! Pt. 07

"Just try it on and see. Please? For me?" Sandra begged. She wanted Mike to try on a white dress shirt that looked like a man's shirt, except that the buttons were on the wrong side with a pair of her black slacks that looked pretty much like men's slacks.

Mike was wearing one of Sandra's soft pink bralettes and matching pink cotton panties. He'd already put on a pair of her not-so-sheer black tights.

"Sandra, I'm not ready to go to work as Michelle yet," he whined back at her.

"You won't be. You'll be Mike. Dark pants, white shirt... you'll wear your men's shoes. I'll bet no one would even notice."

"But someone might," he retorted. "And then what? I'm not ready to be outed at work."

Sandra sighed. "Ok, then. Just the pants? You can wear one of your pullover shirts that you don't tuck in."

Mike sighed and took the pants from her. "I guess I need something to wear to my house to get work clothes, anyway. All I have here is the dress I wore over here Friday night."

Sandra giggled and clapped as he sat on the bed to put them on. "I know. I thought yesterday we should run over to your house and get you some work clothes. But, you know, after Anita left and we came in here I really didn't want to get dressed to leave the house."

Mike laughed. "Yeah, I thought about it, too. I didn't want to go, either." He stood up to pull the pants up and Sandra put a pair of her black slip-on flats in front of him. He looked at her and cocked an eyebrow.

"You going to wear your heels to go home for work clothes?" she grinned.

Mike laughed. "No, I guess not. I guess your flats are less noticeable than my heels."

She handed the white shirt to him. "You're going to have to wear something over your bra. You might as well wear this."

Mike nodded and took the blouse from her. "I'll just have to hope none of my neighbors look too closely at me when I get home."

"Relax, honey. Even if they do they won't notice anything. Well, maybe the shoes," Sandra said.

When Mike had the blouse buttoned he looked in the mirror. The blouse really did look a lot like a man's dress shirt, and the pants could easily pass for men's slacks. With his men's loafers the whole outfit wouldn't look overly feminine. Maybe androgynous? Mike shook his head. He was grasping at straws.

"Do you have any vests?" he asked Sandra.

Sandra smiled and almost ran into her closet. She sometimes wore a vest with a long dress, and she had several. She chose two of the least feminine ones she had- one that was actually a men's suit vest, but it was a dark blue, not black, and one that was denim.

Mike looked at both of them, then took the denim one from her. He looked in the mirror, turning this way and that. The vest didn't really cover the buttons on the shirt, but it took the emphasis away from the front of the shirt. The back of the vest, though, didn't quite cover the waistline of the back of the pants. If anyone took a really close look they would see that the pants were elastic waist pull-on pants.

He tried the suit vest. It covered the back of the pants better, but the blue color really didn't look right with the black pants. He switched back to the denim vest.

"So are you going to wear it to work?" Sandra asked.

"Why are you so anxious for me to come out at work?" he asked her.

She took his hand and sat them both down on the bed. She looked into his eyes. "Because I saw something that first night, when you were first opening up to me. It was like I could see a weight lifting off of you. I mean, almost visibly see it rising away from you. And these past two days I've see how relaxed and natural you are as Michelle. Even when you knew Anita was coming over. And, uh, well, I think Michelle is kinda cute and sexy. And, uh, I want you to be happy."

Mike smiled at her. "I appreciate that. It has been great to be able to be me the past couple of days. Thank you. But I'm not ready yet."

Sandra smiled and nodded. "Okay. I'll stop pushing you."

Mike leaned over and kissed her. "Thank you. I want to. I really do. And I will. When it's time."

An hour later Mike walked into Crawford and Son wearing the black pants with one of his nice Polo shirts that covered the waistband. He'd pushed his feet into his men's loafers without socks. He saw a look of disappointment on Anita's face when she saw him, then a smile when she noticed his pants. He saw her glance at the shopping bag he carried and knew she was wondering what it contained.

When he got to his cubicle he took the flats out of the bag and set them on the floor under his desk. He sat down and slipped his feet out of his loafers and into Sandra's black flats. He felt comfortable wearing the flats in his cubicle, but when he had to leave his cubicle he changed back to his loafers and hoped no one looked too closely at his ankles.

He looked at his hands and hoped no one looked too closely at his fingernails, either. The yellow polish on them was light now that he wasn't wearing the yellow dress to set them off, but if someone looked close...

Sandra walked by his cubicle and stopped to talk. He turned so that his feet were no longer hidden under his desk to show her the shoes.

Sandra giggled and clapped. "You wore them!"

"Just in my cube," he laughed. He pointed at his loafers.

Sandra laughed. "It's a start. Have you talked to Crawford this morning?"

"Not yet," he told her. "I've found some more discrepancies he'll want to see, though."

"Are you going to ask him about dinner?" she asked.

"I want to," Mike said. "I don't know how to bring it up. Hopefully he'll bring it up."

Sandra nodded. "I'm sure he will. Especially if you wear my shoes when you go in his office." She looked down the row of cubicles he'd have to walk by to go to Joe Crawford's office. "You'll only have to walk by other women."

Mike liked how she said 'other women', including him in the club. But he gave her a pained look.

"Ok, ok, I'm sorry," she laughed. "I said I wouldn't push."

Mike laughed. "We'll see."

"I know all of these women. None of them would..."

"I know you don't think so," Mike said. "But I've heard horror stories."

"You want me to talk to them?" she asked. "I could do it quietly. Just make sure they'll all be on our side."

Mike laughed and shook his head. "Please don't. Not yet. In time, I promise."

She smiled and nodded. She leaned down to give him a kiss, then caught herself and stood back up and looked around to see if anyone had noticed. She was relieved to see that no one seemed to be paying any attention to her.

They both jumped when the intercom on Mike's phone buzzed. Mike picked up the handset instead of hitting the speaker button. Sandra leaned in close so she could hear. "Yes?"

"Mike, Mr. Crawford here. Do you have anything to show me today?"

Mike and Sandra both had to suppress giggles. "Yes, I do, Mr. Crawford. I'll print them out and bring them right in."

"Fine," Crawford said. Then he hung up. Mike and Sandra looked at each other, wondering if their boss was angry about something.

Mike hit the button to print the documents, then turned to slip his feet out of the flats and back into his loafers.

"Awww," Sandra whined quietly.

"Hush," Mike laughed.

"Tell me what happens when you come back," she said as she turned to walk in the direction of her cubicle.

Mike knocked on the slightly open door to Joe's office. "Mr. Crawford?"

"Come in, Mike," Joe said. He was standing at the bar holding two drinks. "Lock the door, please."

They met at the side of Joe's desk. Mike took his drink from his boss and took a sip. "Wow! That's strong for before noon!" he laughed.

Joe nodded as he moved to his chair behind his desk. "You may have noticed I have some trouble talking about things sometimes," he said softly, almost as if he didn't want Mike to hear him.

Mike nodded as he sat in one of the chair in front of the desk. "Understood," he said. "Me, too."

Joe looked across the desk. "So. Numbers?"

Mike handed him the papers. He saw Joe look at his hands and smile just a little. Joe studied them for a minute. "What do you make of this?" he asked.

Mike cleared his throat. "Well, it appears to me that someone is letting one of our competitors in on a lot of our trade secrets."

"Exactly," Joe said. "Looks like maybe a few people. Can you tell who?"

Mike nodded. "Yeah, it's pretty easy to track back to them. All the names are on the back page there."

Joe turned to the back page and nodded. "Okay. Are you sure this is all of them? I don't want to leave any loose ends."

"I think so, but I need to run some checks on different departments to make sure. Give me a few more days and I'll know for sure," Mike said confidently.

Joe nodded. "By Thursday? I'd like to call them in Friday and drop the hammer on all of them at the same time."

Mike nodded. "I can have it done by then. No problem."

Joe smiled and got up from his desk. He took Mike's glass and his own to the bar and mixed them each another. "So, do you have anything else to show me?" he asked as he handed Mike his drink.

Mike took a sip of his drink, then set the glass down on the edge of Joe's desk. He stood and pulled his pullover shirt over his head, revealing the pink pull-on bra. The bands on the underside of the bra pushed Mike's soft pecs up and toward the center of his chest to give the illusion of a-cup breasts.

"Oh, nice!" Joe said softly. He reached out to touch Mike, then stopped. "May I?"

"Please do," Mike said. "I like it when you touch me." He tried to make his voice soft and breathy, like Sandra had taught him.

Joe ran his palms over Mike's chest, then pinched both his nipples gently between a thumb and forefinger. Mike's nipples stiffened, and a tingle ran through his body.

"This is a different type of bra than you wore before?" Joe asked.

"Yes, this is called a bralette," Mike said. "Do you like it?"

"To be honest, I prefer the pretty ones," Joe said. "But this is sexy, too." He ran his hands down Mike's sides to the waist band of his pants. He felt the front of the pants, looking for a belt and button and fly, then looked at Mike. "Are these women's pants?"

"Yes," Mike said, again using his breathy voice.

"This is a new thing, right? You wearing women's pants to work?"

Mike nodded. "They belong to a friend of mine. So does the bra, and the panties and hose I'm wearing today. She wanted me to wear a women's blouse, too, but I, um, I was afraid to do that."

"I like it," Joe said. "You did your nails, too."

Mike blushed and nodded. "My friend took me to her nail salon on Saturday."

"They look pretty. Do you mind?" Joe asked as he started to push the pull-on pants down his hips. He didn't wait for an answer, just pushed the pants on down. "Why were you afraid?"

"I don't mind," Mike laughed. "Because I was afraid that it might cause a problem. Some of the men might not, you know, like it. And maybe even some of the women."

Joe nodded as he sat in the chair to push the pants down to Mike's ankles. Mike kicked his shoes off and let Joe take the pants completely off of him and once again stood in his boss's office in just his panties, hose and bra.

Joe ran his hands over Mike's hips and ass, and up and down his legs, and finally between his legs to his crotch. Mike's cock was rock hard, held tight to his body by the hose and panties. Joe ran his hand back and forth over Mike's shaft. "So, so, sexy," he whispered.

"I don't see why it's any of their business what you wear to work," he said, still lightly caressing Mike's nylon encased legs, ass and cock.

"Maybe not, but, um, well, how would it look if I came to work dressed in women's clothes and came in here and locked the door? Is that something you'd want?" Mike asked.

"Hmmm, good point," Joe said. He leaned in and ran his cheek across the bulge in Mike's panties. He put his hands on Mike's ass to pull his crotch harder against his face. He rubbed his face back and forth on the front of Mike's hose.

"You like the feel of hose, don't you?" Mike said softly. He put his arms around Joe's head and shoulders to pull him against nyloned hips and legs.

"Mmm, hmmm," Joe sighed.

"Have you ever thought about wearing them?" Mike asked.

Joe shook his head against Mike's hose covered shaft. "No, I just like to feel them on sexy legs and asses."

"I see," Mike laughed. "I'm guessing your wife doesn't wear hose often?" He knew most of the women in the office rarely wore hose, even with their nicer dresses. The luxury of tight, shiny nylon on a pair of well-turned legs seemed to be lost on the younger women.

Joe snorted. "Yeah, she wears 'em. Every day. The expensive ones. But she doesn't want me to rub on them. And she'd probably hurt me if I ever shot a load on hers like I did yours last week."

Mike moved his hips, rubbing his hosed crotch on Joe's face. "That's a shame," he said. "I enjoyed it when you shot your load on mine."

"Mmmm, me, too," he said. He reached down to unbuckle his belt and pants. When he stood up his slacks dropped down around his ankles. Mike reached down to push Joe's boxers down until they, too, fell around his ankles.

Joe put his hands on Mike's ass and pulled them together, humping his hard cock against Mike's pantyhose encased pubis. He was breathing so hard Mike was sure the girls in the cubicles outside the locked door would hear him.

Mike put his arms around Joe's neck and pushed back against him. He had mixed feelings about what they were doing. On the one hand he loved feeling Joe hump his hard cock against him while he was wearing panties and hose. But on the other hand he'd been thinking of getting on his knees in front of Joe's chair and taking his hard cock in his mouth and letting him shoot his hot cream down his throat, like he'd read about in the online stories.

"I want to pull your hose down," Joe said. "I want to feel your panties." Without really asking he hooked his thumbs in the waistband of Mike's hose and pushed them down around his thighs. Then he stepped back against Mike, pushing his cock against Mike's panties.

Mike reached down to grab Joe's cock. He held it against his nylon panties as Joe humped him. He made sure Joe's cock was rubbing on his own.

"Oh, shit, Mike, that feels so good," Joe gasped.

"Call me Michelle, please," Mike said in his breathy, girly voice.

"Mmmm, yes, Michelle, I like that," Joe said. "Mmmm, your panties feel so good, Michelle. And your dick. I can feel your dick against mine."

"Mmm, yes it does," Mike moaned. He was close to cumming. He moved Joe's cock to the leg opening of his panties. He guided Joe's purple head under the elastic so that his cock was inside his panties, against his bare cock. This was something else he'd read about in the stories and wanted to try.

He wrapped his hand around both their shafts, holding them together as they moved. He could feel his pleasure start to bubble up in his balls. He knew he was going to cum before Joe did. He tried to hold back. He wasn't sure how Joe would feel about him cumming on his dick. But he couldn't help it.

"Oh, fuck, Joe, I'm going to cum," Mike said breathily. "Mmmm, cum with me baby. Cum with me."

"I'm right there, Michelle," Joe panted. "Yes, baby, I'm right there with you!"

Mike felt his cum explode out of his cock, filling the panties and coating his hand and their dicks.

"Oh! Shit! Shit! Your cum is so hot! Mmmm, that feels so good, baby," Joe moaned.

Mike felt Joe's cock start to throb steadily and felt even more cum filling his panties and coating them.

"Nnng, mmmm, arrrggggg," Joe moaned as his shaft pumped shot after shot of cum in Mike's panties. He held his body tight against Mike's, stiff and quivering as he coated Mike's cock and hand with his cream. When he started to relax he pushed his lips against Mike's. Mike felt Joe's tongue and opened his mouth to accept the passionate kiss.

"Whew!" Joe said when he pulled his lips back from Mike's. "Baby, that was the best cum I've had in a long time," he said, still gasping for breath.

"Mmmmm, I'm glad, baby," Mike said. He stepped back just a little to let Joe's dick slip from the elastic of his panties, then slowly dropped to his knees in front of his boss. "Mmmm, looks like I need to clean you up a bit," he said as he opened his mouth to take Joe's sloppy cock in.

Joe put his hands on Mike's head. "Oh, fuck, Michelle, you just keep making it feel better," he moaned.

"Mmmmmn," Mike moaned as he held Joe's soft cock in his mouth and ran his tongue around it. Tasting the cum made him even more determined that the next time he played with Joe he was going to suck his dick and swallow his cum.

Mike pulled his head back and licked around Joe's hairy pubis, then stood up. "I need some napkins to wipe some of this mess out of my panties."

"I'll bet you do. Next time you should being an extra pair of panties," Joe laughed. He pointed to a door near the wet bar. "That's a bathroom."

Mike kissed him on the cheek. "Next time I'm not going to make you cum in my panties," he whispered.

"Oh?" Joe said, raising an eyebrow.

Mike just smiled and went to the bathroom, waddling with his hose still around his thighs. He didn't want to pull them up and get cum all over them.

When he came out Joe was fully dressed and sitting at his desk looking at the folder Mike had given him.

"So these are the ones doing it?" he asked, looking at a list of names on the last page.

Mike nodded as he sat down to put his pants on. It seemed totally natural to be talking about his boss about a work issue while he got dressed. "I think it's all of them. I need to check out a couple of other departments, though, to make sure."

Joe nodded. "Can you have all the names to me by Thursday?"

Mike sat in the chair with his shirt in his hand. "I think so. They're pretty confident. They didn't hide their tracks very well."

Joe frowned. "No telling how long this had been going on." He looked down at the names. "Some of these people have worked for me over ten years."

Mike nodded. "I can track it back and tell you," he said. "But it'll take a while."

Joe shook his head. "It doesn't matter. Just make sure I have all the names by Thursday. I want to call them all in and drop the hammer on them at the same time."

Mike finally put his shirt on, covering his pink bra. "I'd love to be a fly on the wall when you do that," he laughed.

"Why not?" Joe asked. "I can call you in on the meeting, too, if you want me to."

Mike shook his head. "That would make me nervous," he said. "Some of them might figure out how you know all of this if I'm there, too."

Joe nodded. "Okay. But if you change your mind, let me know. Oh, and I'll have security here when I do it. Each one of them is going to be personally escorted to their cubicle to collect their personal things and then to their cars."

Mike laughed. "I'll see them when that's happening." He stood and turned toward the door.

"Oh, Michelle," Joe said. "Uh, dinner at my apartment tonight? 6:30?"

"Tonight?" Mike said, a little flustered. Was he ready for that? He knew he wanted to. He nodded. "Sound nice."

Joe smiled. He pulled an envelope out of his desk drawer and walked around the desk. "Here are all the instructions you'll need. Please don't let anyone else see this."

Mike took the envelope from him. "I won't."

"Wear a pretty dress for me?" Joe asked.

Mike nodded. "I'll try to be pretty for you," he said.

"And I know you will be," Joe said. He kissed Mike on the cheek. "Until tonight."

Mike nodded. "Until tonight."

Mike was almost halfway to his cubicle when he realized he was barefoot. Or, rather, in his stockinged feet. He'd left his shoes in Joe's office! He kept walking quickly to his cubicle. He wanted to look at the women he was passing along the way to see if they were looking at his feet, but he was afraid they were and he wouldn't know how to react if one said something.

He was trembling when he finally sat in his chair and put his feet under his desk. "How could I be so stupid?" he asked himself. Every time he heard movement in the aisle between the cubicles he wondered if it was someone coming to ask him about his shoes, or lack of shoes, and his hosed and painted toenails. He almost jumped when Sandra stepped into his cubicle.

"What's up?" she asked quietly when she noticed that he was upset.

He turned his chair slightly so that she could see his feet. "I left my shoes in Crawford's office," he whispered to her.

"So you walked back to your cubicle barefoot?" she asked.

"Yes!" Mike hissed.

"Did anyone notice your feet?" she asked.

"I don't know," he said. "I was halfway to my cube when I realized I didn't have my shoes on, and I hurried and didn't make eye contact with anyone."

"I could go try to see if anyone..."

"No," Mike said. "If they didn't noticed I don't want them asking questions. I'll just stay in my cube until everyone is gone and then go get them."

"I could take your bag and go see Crawford and bring them to you," Sandra said.

Mike shook his head. "No good," he said. "Then he'd know you know about, well, you know?"

Sandra laughed. "True. Or you could just wear those cute flats you brought to work with you today."

Mike rolled his eyes at her. "You're not helping."

Sandra laughed again. "Okay. I hope you don't have to stay too late to get them. Some of these women work late, you know."

"Crap!" Mike said. "I can't work late. I'm having dinner at Joe's tonight."

"Tonight?" Sandra smiled. "So I guess things went okay in his office?"

Mike blushed and nodded. "Yes."

"Did you strip down to your underwear again?" Sandra giggled.

"Shhh," Mike said. "Someone might hear you. And yes I did."

"You can tell me all about it while we're getting you ready for your date," Sandra said. "I'm going to go finish up what I was doing. I'll come back and help you figure out what to do about your shoes."

Mike nodded and turned to his computer. He tried to work, but he couldn't concentrate on work. All he could think about was what tonight might bring. Would he find the courage to suck Joe's dick? Would Joe want to fuck him? Would he want Joe to fuck him?

"Hey, Sandra, can I talk to you for a minute?"

Sandra turned to see Judy Walker looking into her cubicle. "Sure, Judy. What's up?"

Judy stepped into Sandra's workspace and leaned against her side desk. "Aren't you pretty good friends with that guy Mike, over on our aisle?"

Sandra was guarded. "Well, yeah, we're friends. Why?"

"Well, there's kind of a rumor that you and him have something going on," Judy said quietly. "And, um, I'm nosy."

Sandra laughed and shook her head. "We're just friends."

Judy nodded. "Okay, if you say so. Well, um, today when he came out of Crawford's office he was barefoot, and it looked like he was wearing hose."

Sandra tried to keep her face completely neutral. "Oh? That's odd. Why would he be walking around the office barefoot?"

"I don't know," Judy said. "But Connie and I both saw him. Connie said it looks like his toe nails are painted, too."

Sandra tried to keep her gaze steady as she tried to figure out what to say, how much to say. She felt her face getting warm.

"He does, doesn't he?" Judy said more than asked. "Come on, Sandra. Give!"

Sandra sighed and motioned Judy closer to her. "Yes, he's wearing hose, and yes, his toe nails are painted. But you can't tell anyone! Please? It may all come out in the open soon. But for now he doesn't want anyone to know."

"So is he trans?" Judy asked. "Is he going to make the change to a woman?"

"He doesn't know yet," Sandra said. "This is all kind of new to him. That's why you can't spread it around."

"I have to tell Connie," Judy said. "She's the one who noticed his toe nails. I think he should. He's cute and all, but I think he'd make a cuter woman."

Sandra giggled and nodded. "Me, too. But he's not sure yet. And if the other guys find out, well you know how guys can be such dumbasses."

Judy nodded. "I know. Connie and I won't tell anyone. I promise."

"Thanks," Sandra said. I promise you and Connie will be the first to know if he decides to be a woman."

Judy stood and started to walk back to her cubicle, then stopped. "So why did he go to Crawford's office barefoot? Wasn't he afraid Crawford would notice?"

Sandra's face reddened even more. She had hoped Judy was just going to be satisfied with the information she'd already gotten. She didn't want to tell her what happened in Crawford's office.

"Uh, I'm not sure about that one," Sandra said. "Maybe he did like a lot of us do and kicked his shoes off while he worked and forgot to put them on when he took a report in to Crawford?"

"Uh, yeah, I guess that could be it. I know I've walked around here in my bare feet a few times when my shoes were hurting me. Especially if I wear heels. Is Mike wearing heels today?"

Sandra laughed and shook her head. "I'm sure not," she said. "That would be a little obvious."

Judy laughed. "Yeah, but kinda fun if he did."

Sandra laughed as Judy walked away. She started to clean up her workspace, wondering if she should tell Mike about this.

She ended her workday and went back to Mike's cubicle. He was still facing his computer, but Sandra could tell he wasn't thinking about the numbers on his screen. He turned to look at her as she leaned against his side desk.

"I think you have two choices," she said quietly. "You can either go on up to Crawford's office and get your shoes, or you can slip on your flats and go home to get ready for your date."

"Is everyone up this aisle gone?" he asked her.

She shook her head. "No, but I don't think they'll pay any attention to you. They're getting ready to go home."

Mike looked at her. "What do I do if they say something?"

"So what would they say? 'Hey, Mike, you wearing hose? Cute toe nails.'"

"Yes, exactly," Mike said.

"Then you say 'yes I am and thank you'" Sandra told him.

Mike shook his head. "I couldn't. I just couldn't."

Sandra took a deep breath. "Ok. So Judy and Connie noticed your feet when you were coming back to your cube earlier."

"How do you know?" Mike asked, his voice shaky.

"Judy came to my cube a bit ago," Sandra told him. "She told me her and Connie both noticed your feet and toe nails. I told her that, yes, you are wearing hose and that yes, your toe nails are painted. She wanted to know more and I promised to tell her more later. For now she promised that she and Connie wouldn't say anything or tell anyone."

Mike took a deep breath and shook his head. "I can't believe I was so stupid to forget to put my shoes back on!"

"Well, look at the bright side," Sandra said. "At least you remembered to put your pants and shirt back on," she giggled.

Mike laughed with her and nodded. "There is that."

"So, come on, go get your shoes so we can get out of here and go get you ready for your date," Sandra said. "We only have a couple of hours. Come on. I'll walk with you if you want me to."

"Just to the door," Mike said. "I don't want Joe to know you know yet."

"Deal," Sandra said. "Will you please wear the flats?"

Mike looked down at the shoes and shrugged his shoulders. "Why not. Everyone's going to know soon, anyway." He slipped his feet into the cute shoes and followed Sandra up the aisle to Joe's office.