Dominated by His Beautiful Boss - Part 5 (Patreon)

Click here to read the previous parts of the story.

“Honey!” Justin called out.

“Yes, dear?” Lauren said as she stepped into the closet.

“Where are my shirts?” he said while gesturing to the part of the closest that used to be filled with an array of button up shirts for work.

Lauren stepped closer and smiled as she took his hand. “They’re right there,” she said while pointing to the selection of blouses that hung where his work shirts used to be.

“Lauren, please, stop messing with me. Those aren’t my shirts. Those are blouses,” he said.

“Yes, they are,” Lauren replied. “Those are also the shirts you’re going to be wearing to work from now on.”

“What? Why?” Justin asked.

“Because that’s what your boss wants. Annabelle texted me on Friday and informed me that she wanted you to upgrade your wardrobe in the direction of something more feminine. She says blouses like these are more fitting for the role you’ll be playing at your job now and in the future,” Lauren informed him.

Justin reached up and ran his fingers over the soft, decidedly feminine material of the white blouse that hung closest to him.

“Annabelle was very clear, honey. You don’t have a choice in the matter. You wear these clothes or you lose your job, and I think we both know you’re not going to disappoint me or Annabelle, so stop moping and get dressed for work. You don’t want Annabelle to have to spank your ass before the work day has even begun, do you?” Lauren asked.

Justin thought of the last spanking he’d received. It had happened on Thursday after he’d accidentally spilled coffee and ruined a contract Annabelle had just signed. Sitting had been difficult for the rest of the day as she’d taken to his ass with a belt instead of the bare hand spanking she typically delivered.

“Of course,” Justin said. “I’m sorry for the confusion. I’ll get dressed.”

Lauren gave him a kiss on the cheek and said, “Black and white go very well together, so why don’t you try that pretty white blouse with a pair of black pants.”

Justin grabbed the outfit his wife suggested and laid the clothes on the bed before grabbing a pair of pink lace panties from the dresser.

“Before you put those on,” Lauren said as she moved behind Justin and grabbed his ass with both hands. “I’d like you to do something for me.”

“Of course, anything,” Justin replied as his wife kissed his neck and sent a powerful surge of lust through his body.

“Turn around and get on your knees,” she demanded in a soft, seductive voice.

Justin did as he was told and looked up at his wife from his knees. She pulled down the little pajama shorts she’d slept in and revealed her beautiful pussy. Like most nights, she hadn’t worn panties under her shorts.

“It turns me on to see you being such a good boy for your boss,” Lauren said. “And believe it or not, it turns me on to see you dressing in more feminine clothing. It feels like it’s the way you were meant to dress. It feels so perfect for you.”

Justin nodded as Lauren reached between her legs and played with her pussy. She slipped two fingers inside and then offered them to Justin.

“I think we both know that it’s not quite accurate to call you a man, at least not in the traditional sense,” Lauren said as her fingers moved over Justin’s tongue while he sucked them clean. “You’re not a woman, obviously, but you’re not really a man, either. A man wouldn’t dress in panties, women’s slacks, and pretty blouses for work. A man wouldn’t suck cock for his wife. A man wouldn’t clean another man’s cum out of his wife’s pussy. A man wouldn’t suck cock for his boss, either. A straight man wouldn’t, at least.”

Lauren pulled her fingers from Justin’s mouth and directed his head between her legs. He ate her pussy as she continued.

“I think it’s clear that you’re still on the journey that’s going to take you wherever you belong. I’m so glad I get to go on that journey with you, Justin. I’m so glad you’re such an eager cocksucker for me and Ben. I’m so glad you’re such an eager cum slut, too. I’m so glad that you’re working so hard for Annabelle and that you’re so receptive to her guidance as she trains you to be the perfect secretary for her.”

Justin felt the familiar ache of overwhelming arousal between his legs. Lauren’s pussy tasted perfect and she was soaking wet. She was aroused at the idea of him dressing in a blouse and women’s pants for work. She was aroused at the idea of him being Annabelle’s submissive. All of it thrilled her, which meant all of it thrilled Justin too.

Lauren climaxed after just a few minutes of using his mouth for her pleasure. She leaned down and gave him a soft kiss on the cheek.

“Have a wonderful day at work, honey,” she said.

“Thank you for letting me taste you,” Justin said.

“You’re welcome,” Lauren replied as she pulled her shorts up and left the room.

Justin stood up with a smile and pulled on his pink lace panties before getting dressed in what was now an entirely feminine ensemble.

After he’d finishing buttoning up the blouse and tucking it into his pants, Justin stepped in front of the floor length mirror and smiled. He looked better than he’d thought he would. The blouse wasn’t entirely feminine – there were no ruffles and it wasn’t made of a shiny material – so there was at least a chance that he’d be mistaken for someone that preferred androgynous clothing. 

None of that really mattered, though. What mattered was that Annabelle and Lauren had decided that this was the kind of clothing he would wear now and Justin wasn’t going to argue. Instead, he was going to embrace doing what the two dominant women in his life wanted him to do.

Lauren gave Justin a hug as he came into the kitchen looking for his keys and briefcase. “You look so pretty,” she said.

Her choice of words was purposeful and Justin couldn’t ignore it. He kind of liked it. It was clearly the intention of the outfit choice, so he embraced it.

“Have you seen my briefcase?” he asked.

“Actually, you’ll be using this from now on,” Lauren said as she turned and revealed a sleek, dark blue briefcase that had clearly been designed for women. All the hard angles had been removed and replaced with soft curves that made it look elegant and beautiful. “It’s fitting for the new you, don’t you think?”

“I do,” he replied before picking it up and slinging it over his shoulder. “Thank you. For everything.”

“You’re welcome,” Lauren said before giving him a light smack on the ass. “Have a good day at work.”

Justin arrived early for work, as he almost always did since he’d become Annabelle’s secretary. It was more important to impress her than to get a little extra sleep.

Unlike most days, she was in her office when he arrived. “Justin, please come into my office,” she said through the intercom before he’d even sat down.

“Yes, Annabelle, what can I do for you?” Justin asked as he walked into his boss’s office and gently shut the door behind him.

Annabelle leaned back in her chair and smiled. As she crossed her legs Justin noticed that she was wearing leather pants. It was the first time he’d ever seen her in anything but a skirt.

“I see that Lauren introduced you to your new work wardrobe,” Annabelle said.

“Yes, thank you for suggesting the change,” Justin replied as he ran his fingers over the sleeves of the white blouse. “She might have told you, but I was a little resistant at first. I apologize for that. As it turns out, I quite like this shirt, especially after I saw myself in the mirror.”

Annabelle stood up and came out from behind her desk. Justin couldn’t help but marvel at how good she looked in the leather pants. She wore a semi-sheer sleeveless blouse and a short jacket with them. It was quite the power combo.

“I gave your wife a few suggestions, though she picked this one out on her own,” Annabelle said as she approached and ran her fingers over Justin’s blouse. “It’s quite nice, isn’t it?”

He nodded as his eyes drifted down to Annabelle’s leather pants. He felt the same beautiful kind of arousal he’d gotten used to at work. He wanted to worship the woman standing in front of him and her touch was more than enough to make his cock try and get hard in its cage.

“Do you like my pants, Justin?” she asked.

“Yes, Annabelle. They’re beautiful,” he replied.

She smiled and her fingers drifted between his legs and played with his locked cock and his swollen testicles through the feminine slacks Justin wore.

“The truth is,” Annabelle began, “dominating you makes me feel confident and powerful. It makes me better at my job. It makes me feel like I can do anything. I’d forgotten how much I missed that feeling.” She squeezed his cock and Justin groaned. “I’d forgotten that I need to feel that kind of power to be great at my job.”

Justin was thrilled beyond words that he could help Annabelle experience that feeling. It made him feel as though his submission served an even deeper purpose.

“That makes me very happy,” he said.

Annabelle smiled and stepped closer. She squeezed Justin’s testicles through his pants, kissed his neck softly, and whispered, “That’s good, because I’m going to fuck your ass today and it’s going to hurt.”

All he offered in reply was a groan born of a deep sense of submissive pleasure.

“Take your pants off and bend over my desk,” Annabelle instructed.

Justin rushed to strip off his pants before he moved to the edge of Annabelle’s desk, bent over, and grasped the smooth wooden edge.

She moved behind him and rubbed his panty-clad ass before delivering four swats in quick succession. He gritted his teeth and suffered through the pain of a spanking, though it wasn’t nearly as painful as the last had been. This spanking didn’t seem to be intended for punishment. It was foreplay for the anal sex that Justin would soon be on the receiving end of.

“Have you been fucked before, Justin?” Annabelle asked.

“Not really, no,” he said. “I’ve had toys up there and the butt plug you gave me, of course, but I’ve never been properly fucked.”

Annabelle walked to the other side of her desk, opened the bottom drawer, and pulled out a strapon harness and a long, thick black dildo.

“Black seemed fitting,” she said while dangling the toy in front of Justin. “It matches my pants, after all.”

Justin watched his boss step into the harness and pull it up her legs before slipping the dildo through the opening. She tightened the straps and took a moment to pose with her hands on her hips.

“You look beautiful,” he said.

She looked like a dominant goddess, especially after she took her jacket off.

“Thank you, Justin. You look beautiful too, especially in that lovely new blouse of yours. I think I’d like you to keep it on while you fuck you from behind like a bitch,” Annabelle said.

She pulled a bottle of lubrication from her desk and popped it open before slowly walking towards Justin and moving behind him. He turned around to see Annabelle squirt a healthy strip of lube down the top of her strapon. She stroked the long black shaft with her fingers, spreading the slippery liquid over every bit of its surface.

“Take your panties off,” Annabelle demanded.

Justin pulled his panties down and stepped out of them as Annabelle spread his ass cheeks and squirted lube down his crack. She rubbed the head of her strapon around his asshole to lube it up and Justin groaned.

“Put your hands on the desk, look forward, and try your best to relax,” she said in a soft but utterly commanding voice.

Justin did as he was told and he felt an uncomfortable sense of pressure against his asshole as Annabelle began the process of working the strapon into him.

“It’s important that you learn to take cock, Justin,” Annabelle said as the head of the dildo popped past his anal ring, eliciting an agonized moan as he stretched wider than he’d ever stretched before. “As I’m sure you’ve already guessed, it’s going to be a part of your job. James is absolutely going to take advantage of your ass at some point. That will be at his discretion, but there were no limits on his ability to use you.”

Justin gripped the edge of the desk as he tried his best to relax. He had to remind himself to breathe as his instinct seemed to be to hold his breath in hopes that the pain would recede. It wasn’t going to, though. He needed to get used to it.

“Thank you for training me, Annabelle,” he said.

She laughed and smacked his ass as her cock slid in and out of him.

“You’re welcome, Justin,” she replied. “It’s always a pleasure to train a bitch like you and I think you’ll find that regular anal penetration helps you embrace your place as my submissive secretary. It might make you a better cuckold husband, too. There’s no better way to destroy a straight man’s ego than to fuck his ass over and over.”

Annabelle grabbed Justin’s hips with both hands and quickly found a hard, deep rhythm. She filled him with long thrusts and he groaned each time her big cock bottomed out inside him.

“You’re going to be the perfect secretary, Justin. I’m going to train you to be absolutely perfect in every way, and I’m just getting started,” she said.

Justin closed his eyes and braced himself against the desk as Annabelle fucked him harder. His caged cock bounced with each thrust into his asshole. The pain had begun to recede and there was a little bit of pleasure mixed in.

“Take it, Justin. Take my cock. Take it like a bitch. Be a good little cock whore for me,” Annabelle said as he fucked him harder. “Tell me you want to be my good little cock whore.”

“I want to be your good little cock whore,” Justin replied. He felt a feverish kind of desire wash over him as Annabelle stretched his ass over and over. The harder she fucked him, the deeper he fell into submission.

“Tell me you want to be a pretty little cock whore for me, Justin,” she demanded.

“I want to be a pretty little cock whore for you,” he replied.

Annabelle laughed as she found the strength to pound his ass harder. She grabbed a handful of Justin’s hair and pulled hard on it. His head snapped back as she smacked his ass and fucked him.

Annabelle buried her cock inside him and leaned forward until her body was pressed against Justin’s back. “You’re already a pretty little cock whore,” she whispered. “Your ass is full of my thick cock. You’re dick is dripping precum. You fucking love this.”

Annabelle pulled out and Justin’s asshole gaped open for a few moments. He looked back with what he knew was a desperate sense of desire in his eyes. He wanted her back inside him.

“Clean yourself up in my bathroom. We have a client meeting in an hour,” she said.

“Thank you, Annabelle,” Justin said. “That was unexpectedly wonderful.”

Annabelle stepped closer and reached up to caress Justin’s face. “You’re welcome, my pretty little secretary,” she said.

While she stepped back and loosened the harness straps Justin headed for her bathroom. Wiping his ass clean of the lube hurt considerably but it made him smile. It hurt because he’d gotten fucked and fucked hard by his beautiful, dominant goddess of a boss.

“Thank you again,” Justin said after he’d cleaned up and gotten dressed once more.

“You’re welcome,” Annabelle said from her chair. “Now get back to work.”

“Of course,” Justin replied.

He left her office and took his seat, though he found it difficult to concentrate. His mind kept returning to what Annabelle had said about his training just getting started. It felt like he’d already come so far. What else could she possibly have in store for him? Justin wasn’t sure if he was excited or terrified, but he knew he was going to go along for the ride.