Caught Wearing a Bra! Pt. 01

This is a work of fiction. All characters in this story are over 18.

Mike Alford leaned forward and looked closely at the computer screen. Something was wrong with the numbers, but he couldn't tell what. He switched to another screen and studied the numbers there. After several switches back and forth he saw it. He sat back, his mouth open.

He leaned back in and switched back and forth between the screens again, just to be sure.

He reached for his phone to call his boss, but before he dialed the number he saw Joe Crawford walking up the aisle between the cubicles.

He leaned back and motioned at Mr. Crawford. "What's up, Mike?" Crawford asked jovially as he stepped into Mike's cubicle. Joe Crawford made it a point to know his employees.

"Uh, I thought you might want to see this, Mr. Crawford," Mike said. He moved his chair to the side and pointed to his computer screen.

Crawford leaned in to look at the numbers on the screen. "Am I missing something?" he asked.

Mike hit alt/tab to bring up the other screen. Again Crawford leaned in to look. He put his hand on Mike's shoulder as he looked closer.

A chill shot up Mike's spine when he felt his boss' hand on his shoulder. He wondered if he would feel the thin bra strap or the little adjustment clasp under his shirt.

Mike liked to wear a bra. And other female lingerie. He'd been wearing panties or pantyhose under his slacks for years, but he had just worked up the courage to wear a bra under his dress shirt a few weeks ago.

He blamed it on that website that had a forum for men who like to wear bras. A lot of them wrote stories about wearing their bras under their male clothes and having no problems. Some even said they wore small breast forms in the cups.

Mike wanted to do that, but didn't. But it did give him a thrill to sit at his desk in his open cubicle feeling the sexy, lacy bra hugging his chest. He had loved it... until now, when his boss had his hand on his shoulder and could surely feel the bra strap under his dress shirt.

"Can I see the other one again, please?" he asked, with his hand still on Mike's shoulder.

Mike sat very still. He didn't want his boss to move his hand around and maybe feel the strap. But he had to lean up to switch the screens again.

Mr. Crawford looked at the numbers one more time, then, still bent over with his hand on Mike's back smiled at him. "Good work, Mike. Only an experienced eye would catch that. Print that out for me. I have a quick phone call to make and then we need to sit down and take a closer look at this."

He lightly rubbed Mike's back as he talked. His hand got lower, down to where the thicker bands circled his chest, across the three-hook closure. He slapped Mike on the back as he stood up.

"I'll call you when I want you to bring it in," he said as he walked away.

Mike breathed a sigh of relief. Either he hadn't felt the bra or he had chosen to ignore it. He didn't make a big deal like Mike feared he would. He took several deep breaths to calm his nerves as he printed the reports he'd just shown Mr. Crawford.

His hands were still shaking when he walked to the printer.

"Hey, Mike, are you okay? You look like you've seen a ghost!" Sandra, another young accountant, said as they walked to the printer together. They'd worked together for over a year and often ate lunch with a group of other accountants in the break area.

"Uh, yeah, uh, I just got a little hot in my cubicle," Mike managed to say. He pulled the papers from the print tray and looked at them to separate his from Sandra's. He jumped when Sandra put her hand on his back to look at the papers with him.

"What's the matter?" she asked. "Is something hurting?"

"Uh, no, uh, you just surprised me," Mike stammered.

Sandra laughed softly and leaned close to him, again putting her hand on his back, right on top of his bra band. "Mike, it's okay, I know you're wearing a bra," she whispered.

Mike froze. He stared at the papers. "How...how did you know?" he asked quietly, his voice shaking. "Can you see it?"

"Well, I wasn't for sure today until just now," she said. "But the other day in the break room your shirt kind of gapped open between two buttons and I saw the one you were wearing that day. It was pretty. I wanted to compliment you on it, but, well, there were others around."

Mike laughed nervously. "Thank you," he said. "For not saying anything. Do you think anyone else saw it?"

Sandra patted him on the back. "I would never embarrass you," she said. "And, no, I'm pretty sure I was the only one who saw it. It wasn't real obvious."

She picked up her papers and turned toward the door. "By the way, I think it's kind of sexy." She smiled a sexy smile when she said it.

Mike blushed. "Thank you."

She stopped and looked at him again. "Hey, no pressure, but, uh, would you like to, uh, have a drink some day after work?"

Mike swallowed hard. This beautiful, sexy young woman was inviting him out for a drink? Really?

"Um, yeah, sure, I guess so," he stammered.

"Uh, would you be okay with coming to my apartment?" she asked.

Again Mike swallowed hard. He was having trouble breathing. "Uh, yeah, sure, I guess."

She set the papers down and wrote an address and phone number on a piece of waste paper on the table. "Don't be nervous," she said as she handed it to him. "It's just two friends having a drink."

Mike took the paper from her. "Uh, yes, of course," he said. "What else would I think?"

Sandra smiled and again turned toward the door. "See you after work," she called as she walked out.

Mike's heart was still beating hard, and his breathing was still shallow. So a sexy woman knows he likes to wear bras and she wants to have a drink with him. At her place, not at some bar. His hands were shaking as he gathered his papers and headed back to his cubicle.

Mike was not a ladies man. He'd had exactly one date in high school, and another one while he was in community college. At 5'9" he was shorter than a lot of women, and fairly trim. He walked a lot, some to help keep his weight down, but mostly to try to walk off sexual tension.

When he wasn't working or walking Mike spent his time dressed as Michelle, on his computer perusing several erotica sites. It was on one of those sites that the men in the forum room convinced him he could safely wear a bra under his man-clothes.

His phone buzzed just as he got back to his desk.

"Mike, could you bring those papers in now?" Mr. Crawford asked.

"Be right there," Mike said, his anxiety again rising as he remembered Mr. Crawford's hand on his back, on his bra strap.

Mr. Crawford glanced up from something he was looking at on his desk when Mike walked in. "Close the door, please."

Mike closed the door and handed his boss the papers. He remained standing in front of Crawford's big desk, unsure what to do.

Crawford looked up. "Have a seat, Mike," he said casually. "This is very interesting," he said holding up the papers Mike handed him. "You know what they are doing is costing us a lot of money. Maybe tens of thousands, depending on how long it's been going on."

Mike nodded. "I know. I checked and their account hasn't been audited in several months."

Crawford nodded, a grim look on his face. "I suspected as much. That probably means they have someone helping them. Someone in this office."

Mike nodded. "Most likely. I'll make up a file and turn it over to the auditing department."

Crawford shook his head. "No, don't do that. I don't want anyone to know about this except you and me for right now. I want you to look into it and let me know what you find. I don't know who I can't trust, but I know I can trust you because you brought it to me first."

"But... but... I'm not an auditor," Mike protested.

Crawford nodded. "I know. But I also know you're a damned good accountant, and you could be an auditor if you wanted to be. Well, for now you are."

"And, since you're going to be doing the work of an auditor I think you should get the pay of an auditor," Crawford continued.

He saw the look of fear in Mike's eyes. He leaned over his desk. "Relax, Mike, I'm not going to ask you to confront anyone. You just find the paper trail that will tell me who's doing what. I'll handle it from there."

And Mike was sure he could. Joe Crawford wasn't a big man, but he could be imposing. At only 5'10" he wasn't tall, but he had broad shoulders and chest and thick, muscular arms and hands. His face was friendly, but with a scowl he could let a person know he wasn't happy about something. His short dark hair was speckled with gray.

Mike took a deep breath. "Okay," he said. "I'll see what I can find out." He stood to leave.

"Wait a minute," Crawford said. "Um, there's something else." Crawford got up and walked around his desk. He perched his butt on the front edge of the desk and put his hand on Mike's shoulder.

"Uh, I don't really know how to say this so I'll just come right out with it. Are you wearing a bra?"

Mike looked down at his hands, his face burning. He nodded his head, wondering what would happen next. Would Mr. Crawford now make a big deal out of it? Would Mike's new temporary job assignment change?

"Its okay, Mike. I was just curious. I thought I felt the straps." He walked to the cabinet at the side of his big office. He opened a door and poured himself a portion of bourbon in a clear tumbler. "Would you, uh, like something?"

Mike did want something! His hands were shaking. He had just admitted to his boss that he was wearing a bra!

"Uh, well, I, uh, I'm still working, and uh..."

"It's okay to drink at work if you're drinking with the boss," Crawford laughed. "Bourbon? Gin? Vodka?"

"Uh, yes, some vodka would be nice," Mike finally said. "With a little ginger ale if you have it."

"Ah, I should have known. You like girly drinks, right?" Crawford stopped what he was doing and looked at Mike. "Mike, I'm sorry. That was really rude of me to say."

Mike laughed nervously. "It's okay, Mr. Crawford. I know what you mean." He didn't, but it sounded good.

"You can call me Joe if you want to," his boss said. "When we're in here with the door closed drinking my liquor I think Mr. Crawford is a little too formal," he laughed.

Crawford handed Mike the tumbler of vodka and ginger ale and sat down in the other chair in front of his desk with his tumbler of bourbon.

"Thank you, Mr... Joe," Mike said.

"Mike, you don't have to talk to me about this if you don't want to," he said. "It has nothing to do with your work."

Mike took a big gulp of the vodka, still wondering where this was leading.

"So, would you mind telling me why? I mean, you don't have, um, well, boobs, do you? And if you do that's totally fine! I'm just..." he laughed. "I'm just screwing this up really badly."

Mike laughed again. "It's okay, Joe. No, I haven't grown any boobs. I, uh, um, well," Mike took a deep breath then another big drink of the vodka. "I just like the feeling of wearing a bra," he blurted out.

Joe nodded his head. "I see. Okay. Well, then, that's that. If you like the feeling of wearing a bra, then you should wear one. No reason not to, right? Okay, I have one more question. Again, you don't have to answer if you don't want to."

Mike drained the last of the vodka out of his tumbler, still avoiding looking at Joe's face.

"Just curious, but, um, is it a, um, like one of the little sexy ones? Or like a white, everyday bra, as my wife calls them? I know that sounds like a strange question, but I'm curious," Joe said.

"Um, well, it's not white and, um, yeah, I guess it's sexy," Mike said.

"Um, hmm," Joe smiled, looking at Mike's chest. "I'll bet it is," he said quietly.

Mike stood and put his empty tumbler on the table between the chairs.

"Um, Joe, I probably should get back to my cube," Mike said. "I have a few things to finish up before I leave for the day."

Joe's head snapped up, as if brought back to reality. "Oh, yeah, I guess so," he said. He put his tumbler on his desk and stood to walk with Mike to the door. "Okay, so, start looking into that and see what they've been up to," he said. He put his hand on Mike's back, right on the bra clasp, and rubbed a little. "And, uh, thank you for noticing that. Really, you probably just saved the company a lot of money."

"Yes, sir, Mr. Crawford. I'll start on it first thing in the morning," Mike said, no longer worried that Joe was feeling his bra strap.

'Did he want me to show him my bra?' Mike wondered as he walked back to his cubicle. 'And what would have happened if I did?'

He quickly finished the files he had started earlier in the day, then looked at the piece of paper Sandra had given him. Why would she want him to come to her house? He took a deep breath. "Well, I guess I'll go find out."

He thought about her as he drove to the address she'd given him. She wasn't a beauty queen, but she was pretty. And sexy.

She was 5'10" in her stocking feet, and almost always wore 2" heels to work. She wasn't thin, but she wasn't fat, and had a nice round ass that looked so good in the tight dresses and skirts she wore.

She almost always had her toned legs encased in suntan or sheer black hose when she was at work. Mike tried to remember if she had big boobs. He couldn't remember. 'They must not be too big or I'd remember them,' he thought as he walked up to knock on her door.

Sandra opened the door with a drink in her hand and a smile on her face.

"Mike! I'm so glad you decided to come over," she said as she stepped aside to allow him to enter. "What would you like to drink? I'm having a margarita. Well, sort of a margarita. Okay, it's tequila with lemonade," she giggled.

Mike laughed with her. "You got any vodka?" he asked. "I guess I should have asked if I could bring something."

He noticed that she had kicked her heels off, but still wore her hose. She also still wore the skirt and blouse she'd had on at work. He noted that she definitely didn't have big boobs.

"I've got vodka," Sandra said. Her voice was a little louder than usual. He knew she was already starting to feel the tequila. "I've got tequila, I've got bourbon, I've got gin, and I've got rum. You want it, I've probably got it," she laughed.

"What, do you own a liquor store on the side?" Mike laughed.

"Almost," she giggled. "I have a really good friend who owns one. He makes sure my liquor cabinet is well stocked." She stressed the word 'really'.

She poured some vodka in a glass. "What do you want to cut it with?" she asked.

"Lemonade will be fine," Mike laughed.

"Okay," she said when they were settled, Mike on the couch and Sandra in a chair. "So, Mike, I want to ask you something. Why do you wear a bra?"

Mike laughed and was barely able to swallow the liquid in his mouth.

"Why is that so funny?" Sandra asked, wondering if she was missing something.

"Because that's the second time in about 3 hours that I've been asked that question," he told her.

"Oh?" she asked. "Did someone else at the office notice and ask?"

Mike nodded. "Yeah, someone did. Mr. Crawford."

Sandra looked at him wide-eyed. "Crawford noticed you were wearing a bra at work? How?"

"I was showing him some numbers on a report I was looking at... on my computer screen. He leaned in to be able to read them and he put his hand on my back. I was pretty sure he'd felt the straps. That's why I was so jumpy when we were in the printer room," Mike told her.

"Oh, man!" she said. "What did he say?"

"He didn't say anything right then. But those papers I was printing out were for him... that report I was showing him. When I took them to his office he had me close the door. He offered me a drink and asked if I was wearing a bra. I knew he knew, so I admitted it," Mike said, surprised by how comfortable he felt talking to Sandra about this.

The only other female he'd ever talked to about wearing a bra was his sister, who'd caught him wearing hers. She had laughed at him at first, but later tried to understand and even gave him some of her old bras to keep in his room.

"So, come on, give!" Sandra asked. "What did you tell him? And what did he say?"

"It's funny, Mike said. "It's like he was really nervous, and wanting to ask me more, but... didn't. You know? He wanted to know if I had boobs. I told him I just like the feeling of wearing a bra." He shrugged and smiled at Sandra, again surprised by how easily he was talking to her about this.

"Oh, but he did ask if it was a pretty, sexy one, or a white everyday bra," Mike laughed. "I told him that it's pretty. And he was just staring at my chest and he said 'yes, I'll bet it is'. And he had this weird little smile on his face."

Sandra laughed. "Sounds to me like he wanted to see it," she said.

"Yeah, that's kind of what I thought, too," Mike told her.

"So did you show it to him?" she asked.

"No," Mike laughed. "I told him it was time for me to get back to work and went back to my cube to finish up for the day."

Sandra took a sip of her drink and looked at him over her glass.

"So you wear a bra because you like how it feels?" she asked.

Mike nodded. "Yeah, I do. I always have." He took a gulp of his drink and looked down at it, avoiding her gaze. "It makes me feel, um... I'm not sure how to describe it... but it's felt that way ever since the first time I put on one of my twin sister's training bras. I even asked my mom if I could have one, too."

"Wow. You have a twin sister? That's cool. What did your mom say?" Sandra asked.

"She laughed and said that boys don't wear bras. I kind of knew that, but I wanted one, anyway. For a long time I was mad at my sister because she got them and I didn't. But I used to wear hers a lot."

"Did she know?"

"Yeah, at first she did. I didn't hide it. But she'd go tell on me, and mom would get on me and remind me again that boys don't wear bras and make me take it off," Mike told her. "So I started hiding it. Sis caught me again when we were older and laughed at me... by that time she had boobs and, of course, I didn't. But, well, she saw that it hurt my feelings when she laughed at me, so she said it was okay and even gave me some of her old bras to keep in my room."

"You have a nice sister," Sandra said.

Mike nodded. "Yes, I do. And I've never told another soul what I just told you."

Sandra looked at him with tears in her eyes. "Thank you for telling me," she said softly. "I've heard of men who like to wear women's things, but you're the first I've ever actually talked to about it."

"And I know what you mean about how it makes you feel to wear a bra. It makes you feel feminine, doesn't it? It's the same for me," Sandra said.

"But you're a girl," Mike said. "You have boobs and you get to wear them. You don't need a bra to make you feel feminine."

"You might be surprised," Sandra said quietly. "I wasn't very, um, girly when I was little. And everyone thought that was cute. But when I got older and wanted to be more girly, putting on a bra helped. Even though I don't really have boobs."

Mike looked at her. "You don't have boobs?" he asked.

She shook her head. "Not really. I don't really need to wear a bra, except to hold my 'enhancers' in place."

"Enhancers?" Mike asked. Mike had some breast forms, but he'd never heard them called 'enhancers'.

Sandra reached into her blouse and pulled a rounded foam rubber pad out of each of her bra cups and held them up for him to see.

"Now you can officially say you've seen my tits," she laughed.

Mike shook his head. "I'm sorry," he said. "I just assumed... I mean, you're a girl and girls have... you are a girl, right?"

Sandra laughed. "Yes, I'm a girl. I have all the other parts, just not the boobs. So I understand how wearing a bra makes you feel feminine."