The Cocky Young Associate (Gay SPH)


I was a partner and a practice-group leader at one of K Street’s leading law firms. I was 49, divorced, just shy of six feet tall, and still sometimes called handsome; I worked to maintain my muscular build, although I was thicker around the waist than I had been when I was a younger man.

Matt was an associate in my practice group and a recent lateral hire from one of our biggest rival firms. The firm’s leadership considered it to be a coup when Matt chose our firm out of multiple offers. Matt had already distinguished himself by the quality of his work and even had clients asking for him by name. He made no secret of the fact that headhunters still called him; another high-ranking partner assured Matt that the firm would do what it took to keep him happy. Matt also had an easy-going manner that made him popular with the other associates and the staff alike.

Matt was in his late twenties, over six feet tall, with boy-next-door good looks accentuated by his round glasses and the way in which he combed his medium brown hair. He tended to wear white cotton broadcloth dress shirts with no undershirt, giving a hint of a well muscled and baby-smooth torso.

While I had had experiences with men, I considered myself to be straight but curious rather than gay or even bi. Still, Matt’s beauty filled me with awe. I often masturbated while fantasizing about fucking Matt or having him suck my cock. I particularly enjoyed fantasies in which Matt was nude in my office, either bent over the desk for fucking or under the desk sucking my cock, while I participated in a conference call. I kept trying to plot ways to seduce him.

Matt knew the relevant legal principles cold and also had an intuitive grasp of the ways in which our clients’ businesses worked and of their legal needs. Those abilities made Matt popular with the clients, but they often also made him insufferable in my opinion. Often, when I said something about the way in which a matter should be handled, he would give a “Well, actually…” response. Also, in document preparation, he would give “suggestions” for extensively rewriting what I had written. In addition to plotting ways to seduce him, I started plotting ways to put him in his place.

Matt and I had a business trip to a client’s facility to investigate some of the client’s proposed new products. That evening, I asked him to come to my hotel room to discuss our findings. He arrived, with his tie off and his shirt partially unbuttoned. After we discussed our findings for a while, I said, “By the way, I wish you’d quit mouthing off.”

“What do you mean?” Matt asked.

“The way you’re always giving your opinion, as though you’re always right.”

“Well, I’m sorry for trying to give good service to the client, but I am often right. That’s why you hired me, isn’t it?”

“That doesn’t mean you always have to upstage everybody else.”

“I don’t.”

“Yes, you do, and you want to know why I think you do it?”

“Go ahead.”

“I think you’re compensating for something.”

“And what might that be?”

“I think you’re compensating for having a small penis.”

“Excuse me? Well, let’s just see about that.” Matt stood up, undid his belt and his slacks, and pulled out his penis. He had shaved off his pubic hair, as I understand to be the fashion among younger people nowadays. After a few tugs, his penis was considerably larger than I had imagined it to be. “Okay,” he said, “your turn.”

“My turn to do what?” I asked.

“Your turn to show me what you’ve got.” Matt undid my belt.

“What are you doing?” I asked.

“Seeing whether you can cash the check your mouth just wrote.” Matt undid my slacks, pulled down my underwear, and started tugging.

When we were both hard, he held his penis against mine and burst out laughing. “I’ve got eight inches,” he said, “and it looks as though you’ve barely got five, and mine’s at least twice as thick as yours. But yeah, I’m the one compensating for having a small penis.”

“Can we stop this now?” I asked.

“No, we can’t stop this now. If it mattered a few minutes ago, it matters now. So who’s compensating for having a small penis?”

I was increasingly uncomfortable, yet increasingly aroused. “I … I guess I am.”

“Then say it.”

I muttered, “I’m compensating for having a small penis.”

“Again, and louder.”

“I’m compensating for having a small penis.”

“Good boy. Now I think I’m owed an apology.”

“All right, I’m sorry.”

“I mean a proper apology. Get on your knees.”

“You can’t be serious.”

“I am serious, and we both know that I now call all the shots. Now kneel.”

As he unbuttoned his shirt and spread it away from his crotch, I knelt before him. I could see that his penis was already dripping. He said, “Now tell me that you’re a pin-dicked loser who disrespected a superior and that you’re sorry.”

“I’m a pin-dicked loser who disrespected a superior, and I’m sorry.”


“I’m a pin-dicked loser who disrespected a superior, and I’m sorry.”

“Now suck it.”

“This is going too far.”

“No, it isn’t. Now suck it. Don’t touch yourself until I give you permission.”

Feelings that I could not fully explain led me to comply. Part of me was disgusted and angry, but part of me wanted to obey him and do obeisance to him through his penis. The more I sucked him, the stronger the latter part became. He stroked my hair a few times; I could also see him reach for something and then put it back.

Eventually, I felt his body shuddering, and he came into my mouth. When I looked up, I saw that his shirt had been spread wide enough to show his nipples. Despite my shame and disgust, or perhaps precisely because of them, I found him more desirable than ever.

He looked down and said, “I knew when we first met that you wanted me. Well, now you’ll have me, but strictly on my terms. I have the penis that matters; I make the rules. As far as anyone else will know, nothing has changed, but when we’re alone together, you’ll call me ‘Sir’ and do whatever I say. Understand?”


“Yes, what?”

“Yes, Sir.”

“Going forward, I reserve the right to punish you for screwing up like that. Now, before you get up off of your knees, one more picture.”

“Wait. You took pictures?”

“Why not?” He took his cell phone from the desk, took a picture, and put the cell phone into one of his back pockets. “I have pics of you sucking my cock and now one of you on your knees with that pathetic dicklet of yours standing at attention. Want me to send them to you so you’ll have something to stroke to tonight?”

“You bastard.”

“You left out ‘Sir’ again. You’ll learn. Oh, and I can’t help noticing that you stayed still for the last picture or that you’re rock hard and dripping.” He buttoned up his shirt, pulled his slacks back up, and said, “Have fun masturbating tonight.”

The next morning, having had time to think about the matter, I made up my mind to confront Matt and tell him that what he had proposed was not going to happen. I knocked on the door of his hotel room. He opened the door, still wet from the shower and wearing nothing but a towel. “Oh, hi, come on in,” he said.

Once the door was shut behind me, I said, “We need to talk about last night.”

“You seemed pretty conflicted,” he said, “but you’ll come around. I can tell.”

“No, I won’t come around. That is never going to happen again. Now delete those photos from your phone.”

“Too late. I’ve already backed them up.”

I noticed that he was starting to tent up under the towel. “I can make things very difficult for you.”

“And people will notice and ask why. Remember what they said about keeping me happy at the firm?”

“That’s sure as hell not what they meant.”

He removed the towel, threw it onto the bed, and said, “How about keeping yourself happy?” That large penis of his was soon fully erect. “You can’t take your eyes off of it.”

We stood in silence for a while until he said, “You want it. Come and get it. There’s plenty of time until our flight.”

“No, I don’t want it.”

“Bullshit. You’re staring a hole through at it, and there’s a damp spot on the front of your pants.”

“Listen. What happened was just a mistake.”

He puffed out his chest and said, in a harder tone than I had ever before heard him use, “No, it wasn’t. Now you’re going to get down on your knees and suck my cock. I’m not asking you; I’m telling you.”

The tone of his voice, combined with the sight of his beautiful body and magnificent penis, had an effect on me that I could not explain. I said, “Yes, Sir,” knelt, and sucked him off.

After he came, he said, “That was the real you breaking through. I just needed to say and do the right things to get the real you to break through the shell.”

For about a week, Matt and I pretended that nothing had happened, until our mutual desire overcame our inhibitions. Matt and I got together for weekends and sometimes weekday evenings, at either his apartment in Logan Circle or my house in Fairfax. On other weekdays, since we both tended to work later than most other people in the firm, he called me to his office in the evening, locked the door, and had me blow him. When I hosted in Fairfax, he insisted that I greet him at the door completely nude. He sometimes wanted me to fellate him while he watched television or talked to his friends on the telephone.

Matt also kept on taking pictures. While blowing him, I sometimes looked up into the lens of his cell-phone camera. He also liked taking full frontal photos of me with my small penis fully erect.

I became increasingly comfortable with the idea that although I was still the boss at work, in other respects, Matt was my superior, who ruled me through his large penis, and that he and that penis were entitled to my devotion. It increasingly seemed natural to think that fate had assigned me a subservient role relative to Matt, and I increasingly enjoyed playing that role. During sex, it made perfect sense that I should do all of the work while he got all of the pleasure. Except for the sexual aspect, I sometimes wondered whether dogs felt for their owners as I felt for Matt.

His domination over me soon extended to non-sexual matters. The sofa was his alone; I had to sit or kneel on the floor. When we watched television, he decided unilaterally what we would watch. When he wanted something, he would snap his fingers, and I would get it, kneel in front of him, and hand it up to him. He also insisted that I text him as soon as I woke up and right before I went to bed. When we went to a restaurant together, he ordered for both of us.

One Saturday, we had made plans to meet at his apartment, but traffic held me up. When I arrived, he buzzed me up as usual. However, when I entered the apartment, he was fully nude and fully hard, with a displeased look on his face. He was holding a belt in his right hand. He said, “You’re late” and started smacking his left palm with the belt.

“Well, traffic was—”

“You’re late,” he repeated in the same tone that he had used in his hotel room. He surely knew that the combination of that tone of voice with the sight of his nude body and erect penis left me incapable of resisting. “There has to be a punishment. Drop your trousers and your underwear.”

I did so.

“Now,” he continued, “go to the dining-room table and put your hands on it.”

I did so.

He said, “You’re going to get the belt five times—only five times this time. Now, I want you to count out.” He hit me on my ass with the belt.

“One,” I said.

“That should have been ‘One, Sir.'” He hit me again.

“Two, Sir.”

“Better.” He hit me again.

“Three, Sir.”


“Four, Sir.”


“Five, Sir.” That had hurt, but I could feel the blood rushing to my penis.

“Now, remember: I am the absolute monarch of this relationship, and disobedience will not be tolerated. From now on, you can expect even worse punishment for the slightest infraction. Do you understand?”

“Yes, Sir.”

“Good. I also intend to give you periodic maintenance punishment just to remind you of your place. Do you know what a safeword is?”

“No, Sir.”

“We can talk about that later. Now finish undressing, and get on your knees in front of me.”

I did so. I noticed to my embarrassment that I was dripping.

He stood in front of me. He was dripping, too. “You know what to do now,” he said.

I felt more motivation to put my all into servicing him than I ever had before. When he came, he said, “God damn, that’s the best I’ve had in ages.” He stepped back and said, “You want to be a good little cocksucker, don’t you?”

“Yes, Sir.”

“Do you know why, cocksucker?”

“Because I’m a pin-dicked loser, Sir?”

“That’s right, and?”

“And, um…”

“Because you were put on earth to please your superiors. Now say it.”

“I want to be a good little cocksucker because I’m a pin-dicked loser who was put on earth to please his superiors.”

“That’s right. Again.”

“I want to be a good little cocksucker because I’m a pin-dicked loser who was put on earth to please his superiors.”

“Stay there.” Matt left and returned with his cell phone. He set up something on it and said, “Now, one last time, for video.”

“I want to be a good little cocksucker because I’m a pin-dicked loser who was put on earth to please his superiors.”

“Very good. You’re a natural for this.”

“Thank you, Sir.”

The End.


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