tagGay MaleP Is For Pegged

P Is For Pegged


Inspired by Sue Grafton's alphabetical series.

Wilson Mathews was a bastard. And he knew it.

He ran the Mathews Corporation with none of the compassion that his father had run it with, his only concern being profit. He stalked the hallways, his beady eyes casting about, looking for a worker who was shirking his duty or a technician who was using too much material. He almost always found what he was looking for and thrived from the verbal lashings he doled out on an hourly basis. Those working for him cringed in abject fear but remained on the payroll because the money was fantastic and they knew that once chosen as victim, it would be several months before they'd be chosen again.

The Executive Secretarial position was a different matter. If a candidate lasted longer than two days, everyone was amazed. Temps often filled the role, leaving in disgust a few hours after incurring his legendary wrath and seasoned professionals often departed in tears. No one was good enough. No one was tough enough. No one could withstand Wilson Mathews.

Monday morning began as it usually did for Wilson Mathews. He arose at six and was in his office by six-thirty, a large mug of black coffee nestled at his elbow and a pair of pince-nez balancing on his bony nose. At eight-thirty, Mari Nelson from Human Resources knocked on his door.

"Come in."

"Good morning, Mr. Mathews."

Mathews didn't look up from perusing the reports. "Ms. Nelson."

"I have a candidate for your secretarial opening."


"I wondered if you would like to interview her."

Mathews lifted his head slightly, his hard gaze burning a hole into her. "Ms. Nelson, I've told you before that I don't want to interview them."

"Y-Yes, I know, sir, but I just thought ... "

"Apparently, that is the problem. You thought." He returned his gaze to the reports. "Just bring her up here and get her settled in. I'll handle everything else."

Nelson nodded and hastily departed, her cheeks flaming from his abuse but was happy that she had escaped with little damage. The last time she'd brought a candidate up, he had neatly ripped her a new asshole, claiming that it was unprofessional to hire a candidate without his prior approval. Today, his response was different as she had known it would be. Everyone knew Wilson Mathews was difficult.

Suzan Woodmoore noted the look of exasperation on the HR Director's face but kept her comments to herself. She wasn't sure what was going on but it was clear that the woman was not happy. She remained silent as Nelson reached into her desk drawer and pulled out a file folder and a sheaf of papers.

"Well, Miss Woodmoore, this is your lucky day. You're hired!"

* * * * *

The paperwork and building tour took the better part of two hours. Suzan worked her way through a five page application, non-disclosure agreement, safety in the workplace acknowledgments and various other forms before having her picture taken for a badge. Mari clipped it onto the lapel of her jacket and proceeded with the tour. Suzan paid attention as she learned about manufacturing and its processes. In truth, she knew much of this information already; she had done research about the company before applying for the position.

Finally, it was time to meet Mr. Wilson Mathews, the Mathews Corporation's Chief Executive Officer and Owner and her new boss. Nelson knocked on the door and ushered her into Mathews' inner sanctum. Obviously, Wilson Mathews cared for the finer things in life. His conference table and executive desk were fashioned of cherry, dark red and glossy and all of his desk items, from stapler to in-box were crafted of brushed stainless steel.

When they entered, Mathews stood and Suzan examined him with the eye of a single woman. He wasn't what you'd call handsome but because he was well-manicured and wearing a tailored suit, he looked like a powerful man. She noticed the trimmed nails of his manicured hands and the arch of his eyebrows and knew that he was a perfectionist.

"Mr. Mathews, this is your new secretary, Suzan Woodmoore. Miss Woodmoore, this is Wilson Mathews, our CEO and company owner."

"Nice to meet you, Mr. Mathews." Suzan waited to see if he would extend his hand and when he did, she shook it. His expression was bland and insensitive but the crook in his eyebrows told her something different.

"Thank you, Miss Woodmoore." To Nelson, he said, "Please see that she's settled in." And with that, he returned to his work, not casting another look at her.

Suzan was escorted to her desk, an ergonomic slab of cherry wood, gold piping and stainless steel fixtures. She sat, turned on the computer tower and watched as the company logo splashed across monitor's TFT screen. Another hour of instruction from Mari brought her up-to-the-minute with the corporation's dealings and both were startled when the lunch klaxon blared.

"I guess I'll see you after lunch, Suzan."

"I don't think that'll be necessary, Mari. I think I can handle everything."

"All right. Have a good afternoon."

Suzan enjoyed her lunch in the employee cafeteria and promptly returned to her desk. Not long after she'd sat down, the intercom buzzed. "Yes?"

"Miss Woodmoore, I need to dictate some letters."

"I'll be right in, Mr. Mathews."

That afternoon was relatively quiet. Suzan took several letters in shorthand and left at five, convinced that she had found a wonderful job. The next day would prove to be torturous but Suzan struggled through it. When he requested the letters, she had them completed and ready for his signature. When he asked about an upcoming conference, she had the details ready and his reservations made. When she ordered lunch, he complained of a lack of mayonnaise and she gave him packets that she'd saved. She was ready for his every wish, his every whim.

Friday arrived and she had lasted an entire week and the facility was alive with gossip, everyone excited that she would be the first ever to survive. Suzan knocked on his door and was surprised to find him standing at the window and looking out.

"I came to say 'good night' and to ask if you'd like me to return on Monday."

Mathews was silent for a moment. "Why is it that females always have to ask such stupid questions?"

"Maybe because males are so damned hard to understand!"

Suzan's furious eyes met his shocked ones. "Touché!"

"If you want me to return on Monday, call me on Sunday afternoon. Otherwise, have a good life!"

The problem of Suzan Woodmoore consumed a great deal of his weekend's free time and that alone was not acceptable. He'd lie down at night and see her imperious features and hear her authoritative voice. And another problem developed. The part of his body that he had ignored for nearly all of his life painfully jerked into life. His hand around his erect penis, he tried to make himself ejaculate but was never able to get close enough.

Sunday afternoon, he made a phone call.

"Miss Woodmoore?"


"It's Wilson Mathews."

"Good afternoon, Mr. Mathews. How can I help you?"

"I would like you to return to your job on Monday morning."

"Are you sure?"

"Yes, god dammit, I'm sure! I wouldn't ask otherwise!"

"I'm sure you wouldn't."

"Then you'll be there?"

"Yes, Mr. Mathews, I'll be there on Monday morning."

He'd hung up with a smug smile on his face but again, was unable to sleep through the night.

Monday morning dawned upon Mother Earth and Wilson Mathews arose to meet it at seven. His penis, balls and nipples were sore, the result of his conversation with Miss Woodmoore. Alone in his bed, he'd stroked his prick, squeezed his balls and pinched his nipples in a vain attempt to cum, but had never reached that threshold. But that wasn't what had bothered him the most. The thing that bothered him the most was that when he was young, he had been able to cum at will. But not now and he didn't know why. He hadn't paid any attention to his penis in a long time. Maybe it was broken.

For the first time in nearly seventeen years, he was late to work and exhausted. He retreated to his office to bask in the solitude of machines and silence but was surprised to find Miss Woodmoore sitting at her desk, typing templates for his inter-office memorandums and preparing Powerpoint photos for future presentations.

"Good morning, Mr. Mathews."

Wilson was so shocked to see her there that he almost forgot to speak. "Good morning, Miss Woodmoore."

"I have your calendar for the day. Are you ready to hear it now or would you like a few minutes?"

"Uh, give me a few minutes, please."

"As you wish."

Woodmoore turned back to her work, ignoring the look of confusion on his face. Inwardly, she laughed, happy that her plan was coming to sweet fruition. Drinks with Mari Nelson had given her the ammunition she needed to conquer the position but she knew that she'd need more to conquer his heart. He hadn't recognized her and probably would have sent her away if he had, but he would not have a second chance to break her heart. Not this time.

The intercom chirped at her elbow. "All right, Miss Woodmoore. I am ready."

It was the worst day of his life. For the first time in years, no worker was misbehaving, no material was being wasted, no time was being squandered. He couldn't find a single person or thing on which to vent his anger and he felt lost. He spent the remainder of the afternoon in his office, staring out the window, his mind blank. So he didn't hear his office door shut or the lock click.

"Mr. Mathews?"

He didn't look at Miss Woodmoore. "Yes?"

"You have one last appointment today."

"I do? Who is it?"


He never saw the square of gauze but he knew the smell of chloroform and inhaled deeply before he had a chance to react.

Everything went dark.

* * * * *

When Wilson Mathews awoke again, he was still in his office, but things had changed somewhat. He was sitting in his thousand-dollar ergonomic chair, his hands restrained behind him and his mouth gagged with his own silk handkerchief. He struggled against his bonds for a moment, tears squeezing from the corners of his eyes in response to the pain. What had happened? He tried to think back through the events of the last few hours. Miss Woodmoore had come in and ... yes! Now he remembered. She had drugged him! He'd get that bitch! He'd make sure she'd never work again!

As if on cue, Suzan Woodmoore crept around, moving fully into his line of sight and he started screaming, his foul words muffled by silk. "If you keep making noise, then I'll have to use the chloroform again." Her words had a profound effect on his actions. He became a statue, his almost-black eyes throwing daggers of hate at her. "Good boy." Suzan pulled a chair up in front of him and in one fluid movement, pulled the blonde wig off her head, exposing short, black spiky hair. Wilson's eyes enlarged. "Do I have your attention now?"

Wilson just stared at Suzan, his heart leaping in his chest. My God, she looks like ...

"Brings back memories, eh?" Suzan decided that she wanted Wilson to squirm a little but she needed to hear him talk. She removed the gag with a stern look.

"I seem to be at a loss for words, Miss Woodmoore."

"I bet you are, Wilson, and I bet that's new territory for you."

"What's happening?" Mathews was amazed to hear his voice so calm. "I don't understand."

"You understand, Wilson. I know you recognize me."

Wilson opened, then shut his mouth, his cock twitching with the realization. Stephen Woodboro. "S-Stephen?"

Suzan's smile lit the room and Wilson's breath caught in his throat. "Very good. So I wasn't a footnote."

"Stephen, I never thought you were a footnote."

"Yes, you did. It was easy to forget me, wasn't it? "

Wilson started to speak, but didn't, dropping his head in shame, the memories rushing through his head like a freight train. Stephen Woodboro had been a student in one of his Engineering classes. He was smart, he was quick and he was most probably the sexiest nerd he'd ever seen. But Wilson was a 'straight' man and he couldn't reconcile his feelings with the fact that the young man was gay.

So Stephen became an after-class tryst, allowing Wilson to enter the decadent world of homosexuality with complete and utter trust. And the experience changed Mathews forever. So much that he decided to leave his coveted tenured position and had jumped into the private sector with both feet, anxious to leave the stifling confines of structured education to have freedom. But that freedom had come with a huge price. In his field, power was not wielded by gay or bisexual men.

The day he'd informed Stephen of his decision was the worst day of his life. Stephen had understood but was still angry and deeply hurt. Wilson himself had cried for almost two days straight and from then on, he had become impenetrable. He was an obelisk of diamond; nothing could cut him. Nothing could render him vulnerable. He worked from sunrise to sunset, focusing on the money that he could make and later, the profit that his company could realize. And he'd never thought of Stephen again.

Or so he tried to believe.

"I never forgot you, Stephen."

"Yes, you did!" Suzan's eyes filled with angry tears. "You left the school and I never heard from you again!" She moved close to him, rubbing a finger over his trembling lips. "I thought ... I thought we had something special."

Wilson melted like wax in the sunlight at her touch. "We did! I ... " He took a deep breath, no longer embarrassed by the tears that streaked his face. "I ... "

"That's what I thought." Suzan growled. "Well, Mr. Mathews. Let me refresh your memory." Wilson watched in stunned surprise as she lifted her skirt and presented a strap-on penis for his viewing pleasure. "Remember what this is?"

"Stephen ... "

"My name is Suzan!" Suzan slapped his face with the plastic penis, forcing the fat tip into his mouth. "Why don't you suck on this and remember who you are?"

Wilson couldn't speak. His mouth was filled with the dildo's girth and Suzan didn't cut him any slack. She pressed it into his mouth, watching as he took it down his throat, gagging at first, then finding a place that he could accept it. He had forgotten what it was like to suck a dick.

"Yeah, you like that, bitch? Are you remembering anything?"

Wilson was indeed remembering a lot. He was remembering that the ridge around the crown was sensitive and that a hard dick would slide right down his throat if he angled it right. He also remembered how exciting it was to be near Stephen ... er, Suzan and how long it had been since he'd had sex. Way too long, obviously!

He sucked the plastic penis, rubbing his tongue around the head and along the stalk, his mind wrapped around the Stephen that he knew and Suzan that was his new reality.

"That was very good, Wilson." Suzan pulled the rubber prop from his mouth with an audible pop and went behind him. He felt his wrists loosen and drop. "Now, stand up."

Wilson stood, feeling weak from sitting so long, but he reached out to Suzan to embrace her. She danced out of his grasp and whirled him around, pressing him against the wall. "Suzan ... "

"Time for the show, Wilson."

He felt her hands travel around his waist, the fingers wrestling with, then unbelting his belt and unbuttoning his buttons. His stomach muscles spasmed at her touch and she shoved her fingers into his thick, pubic hair, grabbing his stiff stalk and stroking it. He whimpered, shaking with the sensations. Suzan moved around behind him, her hand still stroking his hard cock, her eyes meeting his in the mirror's reflection.

"Suzan, you're still so beautiful ... "

"Quiet now."

Wilson felt the head of the rubber penis at his ass entrance and tried to move away. "No! Please!"

With one hard thrust, Suzan drilled the dildo into him and he screamed in pain, his legs nearly giving out. "Remember this?" Her voice was hot in his ear, her body hard against his, ramming him mercilessly until his whimpers of pain metamorphosized into grunts of pleasure. "Remember me taking your cherry ass?"

"Yes." Wilson could barely speak, so great was his pleasure. The dildo stretched him wide but it also scraped his prostate, making him writhe in delight. And the fact that it was Suzan made his dick even harder. "God, yes!"

"Remember the sound of my balls slapping your ass? Remember the sweat that covered our bodies?"

"Oh, yes." Wilson was remembering. He was stroking his own cock now, his fingers wrapped around Suzan's.

"Do you want my cock in your ass now?"


Wilson groaned as Suzan pulled out of his ass and quickly dropped the harness. Hidden underneath was the beautiful penis he remembered: long and thin with a large fluted crown and a small set of balls, completely shaved. He couldn't stop himself from falling to his knees and taking Suzan's organ into his mouth, caressing the musky skin with his tongue and sucking the oozing pre-cum from the wide slit.

Suzan's groan was like music to his ears. "Oh, God, Wil." A series of shivers ran through her body, making her nipples harden. "God, I've missed this. You always knew how to work me." Wilson hummed along Suzan's length, making her toes curl. "Okay, I'm ready."

Wilson turned back around, presenting his already loose asshole and Suzan plunged in, their moans mingling. "Oh, yes. Fuck me, Suzan." He closed his eyes, relishing the touch of her skin on his and turned his head, allowing her to plunder his mouth with her tongue. Her cock moved smoothly in and out, filling him then retreating and his hand covered hers, both enjoying stroking his cock while stroking his anal canal. "Oh, fuck, I'm gonna cum! Oh, Suzan! Fuck!"

As thick ropes of cum spewed into his and Suzan's combined palms, Wilson groaned loudly, his body shaking both from his climax and the pounding that his ass was still receiving from Suzan. It didn't last long, though. With a cry of his name, Suzan came, pumping her semen into his grasping asshole, holding his trembling hips as they dropped to their knees. It was several moments before Wilson was able to speak.

"I'm sorry."

* * * * *

* * * * *

Wilson Mathews was a bastard. And he knew it.

He ran the Mathews Corporation with the compassion that his father had run it with and took pride in the fact that it was highly profitable. He walked the hallways, his beady eyes casting about, seeking out workers and technicians and thanking them for working for him and praising their efforts. He almost always found what he was looking for and thrived from the expressions of joy that he received on an hourly basis. Those working for him admired his change and remained on the payroll because the performance bonuses were fantastic.

The Executive Secretarial position was a different matter.

Suzan Woodmoore did not return on Tuesday. Instead, there was a young man seated at the expansive desk, his suit well cut and his appearance immaculate. At lunch time each day, Stephen Woodboro entered Wilson's office, shutting and locking the door behind him, pushed his boss against the wall and fucked his ass until they both came. And at six o'clock, they went home together.

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