Tuxedoed Encounter

He didn’t arrest my attention just because he was strikingly good looking—tall and slim, graying at the temples, probably mid-to-late forties, with commanding hazel eyes and a ready smile in movie-star-handsome features. He was wearing a tuxedo—and wearing it quite convincingly. What was unusual was that I was wearing one too and so was the young man standing behind him. That, in itself, wasn’t unusual, but where we were wearing tuxedos was what was unusual. We were in the visitor’s room of the Annapolis, Maryland, police station, me at one window and he at the one beside mine, negotiating with a police clerk in getting our respective clients out of lockup.

He looked familiar, and I thought he might recognize me too when he looked at me and smiled. But I couldn’t place him, not even when I heard him tell the young man behind him, “Collect Mr. Hadley when he comes out, Ed, and see that he gets home—and try to keep away from any reporters lurking around. They’ll have the story soon enough.”

The young man answered, “Yes, Mr. Masters.” That name seemed familiar too but no lightbulbs went off over my head. We were just two lawyers called away from wherever we’d been wearing tuxedos—not the same event, I didn’t think; mine had been in Baltimore—to spring clients from jail for now. My client was a junior banker from Wilmington who had been pulled over near an Annapolis bar on a DUI.

It appeared that the man was about to say something to me, when my cellphone rang and I answered it. It was the client’s wife. My response after we click off was a verbalized, “Shit.”

“What’s the matter?” the man next to me asked as he pulled away from his window, replaced by the young man he’d told to finish up their work here.

“The client. Or rather the client’s wife. She hired me to spring the guy out—a DUI—and now she says not to do so. She says his office wants him to sit on ice for a day or two to give him something to think about. She didn’t seem happy at all. And she was being unhappy at me. It isn’t my call, of course.”

“Of course not,” the man said. “I’m Carter Masters. An Annapolis firm. You?”

“I’m Tyler Ware. New to it. Working out of Baltimore.” We shook hands. He briefly wrapped fingers around my thumb when we pulled back, which surprised me. In the world I’d come from and was trying to move beyond that had meaning—a seeking submissive. I was sure it was just an accident here. It did cause me to take a second look at him and then to quickly look away. Yes, he was attractive in that way, but I had changed my life since law school and clerking for Judge Prentice.

“So, it’s back to Baltimore and whatever you were doing when you were called out?” he asked, providing the first reference to recognizing that I was in a tuxedo.

“Yes, but now I don’t know how to get back. I left quickly when I got the phone call. The client’s father is one of our major clients—you know how it is, I’m sure. Another lawyer was leaving the banquet early—that’s where I was, a farewell banquet at the Renaissance Harborplace for one of our senior partners—and a let him drive me over here without any thought to how I would get back.” I had left the car for my wife, Pattie, to get home, but something in the back of my mind prevented me from telling Masters I was married.

“Yes, I know how catering to the important clients can be,” he said was a winning smile. “It so happens I’m driving back to Baltimore now. I was called away from an evening at the opera. Perhaps I could give you a lift.” And, thus, we’d both provided plausible explanations for being in tuxedos. It didn’t occur to me until later that a question lingered there of why his younger associate, Ed, was in a tuxedo. Was Masters at the opera with a younger man, a law associate? But I didn’t think anything of that at the time.

“Yes, if you’re going anywhere close to the Inner Harbor, that would be very good of you. I’m not sure how much longer the banquet will be going on, though.”

“Will you really miss not having banqueted?” he asked, flashing me that glorious smile of his.

“Not really,” I answered.

“And me neither on the opera,” he said. “Shall we? My car is just outside.”

* * * *

I shouldn’t have gotten into the sleek, black Mercedes sedan with Masters—not if I was serious about establishing a new life. I probably knew where this would lead when I got into the car in Annapolis, but I did anyway. That handshake, coming from my hidden world—the encasing of the thumb. And had he stroked it a bit? I couldn’t remember. But it was hard to misunderstand that signaling. How had he so quickly gauged my interests? If it hadn’t been a mistake, he was from my hidden world as well and had seen it in me. Could I—with him? I looked over at him in the driver’s seat. Yes, I certainly could.

It was only a forty-five-minute drive to cover the distance from the capital of Maryland on the Severn River to the Baltimore inner harbor, and conversation was kept to a minimum. But the link was established during our chit chat and I didn’t even realize it at the time.

Masters told me he was a lawyer in an Annapolis firm that was branching out into Baltimore. If he told me the firm’s name, I don’t remember. I was too busy trying to hold my nerves in check, sitting there, in the plush darkness of the Mercedes cabin, beside an elegantly dressed, movie-star handsome older man I couldn’t deny I fancied. I’d been aflutter since he’d reached over to change the gear from reverse to drive and “mistakenly”—or so I told myself—overshot and gripped my knee instead.

But could we? Would we fit? Did he know I was a top. It usually was the other way around in arrangements like this. The signal—him sheathing my thumb should indicate a fit. But he was a command sort of guy. Commanding from the bottom? That too fit my fetish, as did him being an older man.

“Sorry,” he said, turning his face to me and smiling. I don’t think he was sorry, though. He didn’t pull away for the longest moment—much longer than was necessary to adjust for an innocent mistake. I’m sure he could feel me tremble to his touch.

If this was what I thought it was, I thought. I should be taking command more, whether or not I was agreeing to a hookup—at least initially. I could give over control later to the pleasure of both of us. I had always been a top, although I liked it best if the bottom took the initiative. I didn’t want to give him the impression I was a submissive. I needed to get across that I was the one with the shaft—or at least that I had been “the big dick” to ride when I was active, at the university and early on in law school until I caught on to what sort of life successful lawyers had to convey.

I hadn’t thought about these issues—had I?—since before Pattie and I had become engaged, had married, and had set into a successful lawyer’s life, partially thanks to Pattie’s father, a senior lawyer at our firm, not the lawyer who was being feted tonight to retirement, but soon to follow. The firm was in talks with other firms wanting to acquire us. Some of our lawyers would stay with the new firm and some would be pushed out. Pattie’s father would be retiring soon. I had to walk the straight and narrow if I didn’t want to be one of the ones pushed out in a merger.

The link was provided innocently enough.

“Where did you go to law school?” Masters asked as we pulled onto I-97, headed toward the Baltimore beltway.

“Right here in Baltimore—the University of Maryland.”

“Ah, yes, a good school. I know several of the professors there.”

“I studied under Judge Prentice. William Prentice,” I said, walking into the trap all by myself.

“Yes, Bill’s a good friend of mine. A very good friend. We look out for each other.”

There it was, although I didn’t complete realize that until I was rethinking the conversation later. I had been Judge Prentice’s law clerk as well as one of his students at law school. I also had been one of his lovers—one of the boys he cajoled into covering him to be in good favor with him and to receive his mentorship and sponsorship. Judge Prentice had been the one to teach me to give over to command from the bottom. With Prentice it had been just lying there, providing the erection, and Prentice doing the rest, saddling himself on me and riding me for his own pleasure, not really caring if I got off as long as he did.

Our conversation in the car moved to more neutral ground from there, but without my realizing it, we’d touched on the essential and something had been established.

“Judge Prentice and I are very similar in our approach,” he said. “We discuss his law clerks from time to time, and I think I remember your name coming up. Did you enjoy serving under him?”

“It was fine,” I answered, not being sure he was conveying what I thought—and more than half hoped—he was.

Masters seemed much more assured from that point. He stopped dancing around what might be and moved into command, telling me where we would go from here. I didn’t balk. I followed his lead.

Thus, when we got to the Renaissance Harborplace Hotel on the waters of Baltimore’s Inner Harbor, he exited the Mercedes as I did and turned the keys over to a car valet. He wasn’t just dropping me off.

“If you had to leave the banquet early, you must not have gotten supper,” he called out to me over the top of the car.

“No, I didn’t,” I answered. “If the banquet has closed down, I thought I’d get a bite to eat in the restaurant here.”

“I didn’t get dinner either. I’ll join you.”

And join me, he did. The retirement banquet had broken up. They were clearing out that hall. Pattie was gone, so was my car as well. I’d have to take a hotel car or a taxi home. It wasn’t that far. We lived in the up-scale and historical Ellicott City—with Pattie’s widowed father. I had called him from the jail in Annapolis. I had told him that I didn’t know if I’d get home that night or not. I couldn’t help but think that that covered for “whatever.” We were all lawyers. We all knew all there was to know about getting a client busted out of jail completely taking over a whole night.

After dinner, Masters suggested we stop at the bar for a drink, which we did. I was letting him lead. Our conversation at dinner and then afterward, at the bar, over more than one drink, became more intimate, centering more on a hookup. That we would fuck wasn’t directly stated by either of us, but neither of us were misunderstanding what we were leading too. References to Judge Prentice came up frequently, including that he was gay—and a submissive, but one who controlled from the bottom—and was notorious for sleeping with his male students and law clerks. No bones were made about my having been one of his students and law clerks or that we’d had a special relationship.

“I hope I’m not being too forward—that I’m not embarrassing you—that these aren’t revelations about Prentis.”

“No, not at all. I knew that about the judge,” I answered. Masters placed a hand on my knee under the table briefly and gave me a smile.

“Good,” was all he said.

Masters excused himself, saying he had to go to the men’s room but that would I please stay until he came back.

I should not have stayed. I should have said I needed to get home. But I stayed. When he returned, he was holding two room cards. He gave me one.

“I’ve checked in. If you wish to use this, come up in fifteen minutes. If you come, you will be at my command.”

I should have said no. I didn’t. I waited fifteen minutes and then went to the elevators to the upper floors.

* * * *

When I entered the hotel room, he was waiting and ready for me. Nothing was spoken. Nothing needed to be spoken. He was sitting on the end of the bed, facing the door I entered. He had stripped his shoes, trousers, and briefs off. He was wearing his dress shirt, but he’d taken the studs out, he wore no undershirt, and the shirt was gaping open to show that he was hard-bodied, trim, and that he has a thin patch of salt-and-paper, silky hair swirling around his pecs and then descending in a line over his hard belly and down into his pubes. He was wearing dark dress socks covering the meat of his calves and being held up by black silk garters encircling his legs just below his knees. He was leaning a bit back on the bed, propping himself up with one hand. He was stroking a long erection with his right hand.

I stopped just inside the closed down, letting out a little gasp, not expecting it to have progressed this far yet.

“Strip for me, please. Down to the socks, but keep the briefs and tie on for now. Slowly please.”

I could hear his ragged breathing and held his slitted eyes with mine as a did so.

“Turn, please, slowly.”

I did so.

“Ah, to be young and beautiful again,” he murmured. He was quite well done even for his age, as far as I could see.

“Now the briefs. Oh, my, you are a big lad, aren’t you? I was told you would be. And you want me as much as I want you.”

“Yes,” I agreed. But who had told him I was hung?

“I will fuck you, right—you providing the shaft?”

“Yes, if that’s what you want.”

“Come to me now. Prepare me.”

I moved to the foot of the bed. He spread his legs. He continued to stroke his cock with his right hand, but he reached out with his left as I went down on my knees and held his erection up with his right, cupping the back of my head and guiding my mouth to his shaft. He moaned and gave a deep groan as I slid my lips down the sides of the cock and began giving him head.

It had been a couple of years since I’d done this for a man, but it was like riding a bicycle. And I knew I was good at it. He leaned back on the bed on both of his elbows and left me to my work, murmuring, “Yes, yes, that too,” as I grasped his butt cheeks between my hands, squeezed and separated them, rolled his pelvis up, and went for his hole with my tongue, alternating that with given attention to his cock.

“Are you going to open for me?” I murmured, and then, “Yes, you certainly are.”

He was panting hard and urging me on, when I stood, put his ankles on my shoulders, hovered over him, moved into position, and mounted, penetrated, and fucked him.

Before finishing, he insistently pulled at me to come up onto the bed, which I did. He turned me on my back and mounted me, saddling himself on my hips, descending on my hard shaft, and riding me to a mutual completion.

“Lie there without moving. Just remain hard for me,” he direct.

I lay there, on my back, wondering what, if anything, came next, with Masters hovering over me, kissing down my body, sucking my cock and balls. Visions of lying still, with Judge Prentice saddled on my loins, me inside him, him telling me just to lie there as he rose and fell on my cock, riding me to his completion took me back to the world I had been trying to leave behind me. Masters was more of an enticement than Prentice had been—better looking, more fit.

“Stretch back, open your arms wide, keep it hard, be my joystick,” Masters murmured as he positioned himself on my hips, put my cockhead in position, and slowly descended on. Down and up, down and up, he was approaching a steady cadence, when my cellphone went off.

“Shit. I should have called,” I muttered. I stopped myself in time not to say I should have called Pattie to let her know where I was, what was happening in Annapolis with the emergency client call, and when I might be home in Ellicott City. Masters didn’t need to know that I was married. But I’d told her dad I might not make it home tonight, my mind—my desire—called out.

“Should have called who?” he asked as I scrambled out of bed and to the door, where I’d left my clothes. I found my cellphone, clicked it on, said “Jason Ware here” in as calm a voice as I could muster under the circumstance, listened, and then clicked it off.

“I’ve got to go,” I said. “That was my client’s wife again. She’s changed her mind about getting her husband out of the cells tonight. She doesn’t care what his employers want. I have to go back to Annapolis.”

“I’ll drive you,” Masters said, but I was already making another call, to my wife. “Hi, it’s me. I came back to Baltimore but the party was over. I have to go back to Annapolis tonight. I’ll have to get a hotel car or something. What? You did? OK. I have no idea when I’ll be home.”

I clicked off and gathered up my clothes. I should have thought Pattie would have done that. She’d gone back to Ellicott City with her father. She’d left the car here for me. “Thanks, but I have a car here. I won’t need you to drive me.”

“Come back to bed. Let’s do it—”

“I really do have to go back to Annapolis,” I said as I marched off to the bathroom. When I came out, he was still stretched out on the bed, propped up on pillows. He’d found a small bottle of something from the room refrigerator and had that in his left hand. He was stroking himself again with his right hand.

“Until next time,” he said to me as I was bustling out of the room. He had a smile of self-satisfaction on his face. I doubt if he had any idea how far and hard he’d made me fall off a change of lifestyle wagon I had been working so seriously to manage.

If I could help if—if I could control my weaknesses—there wouldn’t be a next time.

But, shit, that had been glorious. I’d never been harder than when he told me just to lie there and be his joystick.

* * * *

My resolve not to slide back lasted for less than two weeks, and it came with the harbinger of changes in my life that went further than that.

Even as junior as I was in the Baltimore law firm, I had a clerk. Mine was male, although he was a bit of a swisher, so I saw him as someone to be wary of from the time he was assigned. I was afraid he’d maneuvered his way to be my clerk to gain a sexual relationship with him when I was determined not to mix sex and the office.

Avoiding getting involved with my clerk was easier to do before Carter Masters knocked me off the wagon. Dan Echols was a handsome, willowy young man. He was still in law school—at the University of Maryland and one of Judge William Prentice’s students, which told me right there to be careful of him. There could be no reason in his clerking capabilities to reject his service. I had gotten him thanks to my senior partner father-in-law and I couldn’t have turned him away without acknowledging that I knew he was gay, that he was a submissive, that he was willing to give it out, and that he had his hat set for me.

I speculated on whether Judge Prentice had told him about me and what I once involved myself in, but by the time our relationship came to a head, we’d gone way beyond such speculation. It started to unravel because of the rumors of our law office’s fate.

We were working late one evening—just the two of us, Dan and me.

“When you go to Hedges, Masters, and Simons do you think you’ll be keeping me on, taking me with you?” Dan asked. He tried to be casual about it, but I could tell he was uptight about something this evening. I could also see that he was on the make. He had dressed to emphasize his considerable sexual charms—for anyone who might be interested in that.

“What do you mean? Going where?” I asked. “Nothing has been said about this firm being taken over by another. I know there’s been gossip about that with Wilson having retired and my father-in-law signaling he is as well, but there’s been nothing—”

“It’s all the talk of the office. The deal has already been done, I’ve heard. An Annapolis firm wants a Baltimore branch—an established one.”

“Shit,” I said. “Why is it that the clerks and secretaries know more about what’s happening around here and faster than the associates do?” I was asking the wrong question and paying attention to the wrong part of what Dan was saying. I hadn’t absorbed the name of the firm acquiring us.

“I’ve heard that more than half of the associate lawyers will be kicked free. That means their clerks will be fired too. Only the best will be kept and the surviving lawyers will go after those. I need to know if I should be looking for another boss. I’d rather it was you. You’re the nicest one for me. I know what you like. I’d be happy with that.”

“How do you know I would be one who is kept. I’m not senior among the associates, and the reality is that once my father-in-law goes, I’ve lost my networks here. And what are you offering me?”

“There’s a list circulating on what associates are being kept. Your name is at the top of the list.” He didn’t give me time to absorb that—no less than to marvel again that the clerks knew more about the firm’s future than the associate lawyers did. “You know my law school mentor is Judge Prentice. He’s told me what you like. He told me how big you are. I’ve worked hard to get you for a boss. I’m willing to give you anything you want to go with you to the new firm.”

Maybe if we’d had this conversation before, I fell off the wagon with Carter Masters . . . but I had fallen off the wagon with Carter Masters, and Dan Echols was an irresistible little piece. And he was making himself more so by stripping in front of me and going down on his knees.

I fucked Dan doggy style, bent over my desk, with the palm of one hand pressed between his shoulder blades and the other grasping the back of his neck, holding him securely against the mahogany tabletop and pumping him hard. He at least professed to love it and egged me on, earning the privilege to go with me as my clerk and frequently to work late nights with me.

And he was right. My firm was acquired by the Annapolis law firm of Hedges, Masters, and Simons and I was retained—in fact moved up in rankings—on the firm’s associate lawyer list.

* * * *

“I think you know the Masters, Carter and Marge, and their girls, Heidi and Beth,” my wife, Pattie, was saying as I tried to contain my shock. A smirking Carter was extending his hand for us to shake. He was clearly enjoying the moment. “Carter and Marge came to our wedding. And here too is your law professor, William Prentice.” William, standing close beside Carter also was smirking.

We were boarding a river cruise boat, the Harbor Queen, on the Severn River at the Annapolis docks. This was the first of several social events that were being laid on to ease the merger of my Baltimore firm into the Annapolis firm of Hedges, Masters, and Simons. This was the first time I actually focused in on the new firm name, which was displayed on a placard at the top of the gangway onto the boat.

Pattie and Marge, deep in conversation moved further into the boat. The two young girls had already swished away from us. This left Masters and Prentice standing there, with me, obviously enjoying the time it was taking me to adjust to the reality.

I looked at Masters. “You knew. You’d already discussed me with Judge Prentice. Was that night at the Annapolis police department all a setup?”

“Of course I knew before that night. I even told you I had that night in the Inner Harbor when you ran away from me. That night was just fortuitous, but we would have met somewhere and done what we did sometime anyway—what I hope we’ll do again now that you have been brought into the firm. No,” he said, with a smile. “I command that we do it again—and again. I believe you respond to command, don’t you, Tyler?”

The way he said it left no doubt what would be expected from me for having been brought into the firm.

“The judge is an old friend of both the firm and me, and he shares with me—including promising lawyers and law clerks. Are you going to be fine with that?”

“I was trying change,” I said. “I’d been changing. You’re married.”

“So are you,” he shot back. “You haven’t changed too well, obviously,” he said, and both men gave a little laugh. “There is no need for you to struggle for change. The firm likes you—I like you—as you naturally are. I ask again, are you going to be fine with that?”

“Yes, I’ll be fine with it.” I didn’t say that just to preserve my position in the firm. I saw no reason to fight what I liked anymore. Masters obviously managed to have a normal family life with his men on the side. I saw no reason why I shouldn’t be able to have that as well.

The two men drifted off. Before I was able to do so, the law clerk I’d brought into Heges, Masters, and Simons with me, Dan Echols, was coming up the gangplank. He looked awfully inviting in his tight T-shirt and Speedo. I winked at him. He registered surprise and then gave me a glorious smile. This new, more open life was going to be interesting.

I had given up on giving up.

* * * *

Masters wanted me to second chair him on a case that was coming up in court in the near future. We had to cram to be ready for it.

“It will require some late hours,” he said. “We’ll have to work into the night. Call your wife to tell her that and then turn your cellphone off.” We had returned to the head office in Baltimore from an evening together at the opera—I had suddenly become interested in the opera, although Pattie wasn’t and told me to indulge the interest by myself. She was pleased, from a career ambition standpoint, that Carter Masters had taken me under his wing to introduce me to the world of opera. We were both in tuxedos. All of the women in the office kept looking at us and sighing. We knew we looked good.

The time was excruciating that it took the office to clear out that night, the two of us in Masters’s office, our heads together, our tuxedo jackets and bow ties off, huddling over the pile of briefs affecting the case, my mind running through all of the permutations of staying or leaving.

Later, with me, naked other than black dress socks held up by garters and on my back on the carpet between his desk and the floor-to-ceiling glass wall overlooking the Baltimore Inner Harbor and Masters in just his tuxedo shirt, studs out, shirt front billowing open, and black dress socks with garters, I stretched my arms out in the sacrificial cruciform position he demanded of me while Masters hovered over me, sucking me to a throbbing, formidable erection, and then mounted my loins, murmured, “Just lie there. Let me do all of the work,” put my cockhead in position, descended on me and rose and fell, slowly, languidly at first and then with increasing intensity and vigor, on his joystick.

Yes, I saw many a late night at the office in my future.