It was the wrong choice of swimwear, and I was headed back to the guest room to rectify that, when the cause of it all stopped me in the hallway. The new owner of our company had invited me to his country place for a weekend to discuss some details of a project we were working on, and it turned out there was a pool party included. But, not knowing that, I hadn’t brought my suit. I had assumed this would be all business. So there I was, having to pick out a loaner suit from Thad, my boss, and I’d picked the wrong one.
The choice really was between a pretty skimpy Speedo and something that looked like boxer silks. I’d rejected the boxers because they didn’t come with a supporter, and I was afraid that all I’d have to do was go into the pool and I’d come out showing everyone everything. I didn’t think this was the right impression to be making on the new owner of my company. Turns out that wouldn’t have been a real problem, because Thad had only invited men to this party—but, then, I didn’t know that when I put the suit on.
Thad, counter to everyone else, had come to the party decked out in a gladiator costume. His great pecs were crossed and highlighted with leather straps, the waistband of a short pleated skirt thing dipped well below his navel in front, and there were leather wrist shields and sandals with leather straps winding up his calves. Thad was a heavily muscled hunk and I’d about spill my seed in meetings with him for the three weeks he’d been on board, but this Roman costume, which showed off curly chest hair I’d never seen before to match the curly dark hair on his head and the curls showing above the waistband of his skirt really was too much. My interest was just too obvious when all I had on was that Speedo. So, I was heading back down the hall to put those boxers on over the Speedo when I nearly ran into Thad himself heading up the hall.
As I was about to pass him in the corridor with no more than a smile, he put one arm against the wall in front of me, and the other hand came out to stop me. Unfortunately, it came out at a pretty low level, and there I was, trying to take care of the start of a hard on for my boss, with my boss standing close to me with the palm of his hand spread out on my lower belly.
“Here you are, Tim,” he said in a casual voice. “I saw you outside, but then you were gone, and I wanted to talk to you about an idea I had on the Robinson project.”
I tried to remain nonplussed and to at least appear more attentive to what he was saying than to the growing tenting out between my legs of the Speedo, but I wasn’t doing a very good job of it. I could feel my engorging cock, which really was too big for a Speedo in the first place, pulling the hem of the suit down beyond my pubic hair line. It must have been my imagination, but I got the sensation that Thad’s hand had moved down farther as well.
“But you’re not completely with me here, are you Tim?” Thad was saying as I snapped back into the conversation.
“Well, no, Mr. Stevenson, not actually. There was something I needed to do back in my room, and I’m afraid I was focused on that.”
“It’s Thad to you, Tim . . . and that something you needed to do wouldn’t have to do with this very interesting hard on you’ve got, would it?” That was another thrilling thing we’d all learned about Thad at work. He was very direct.
I mumbled something that even I didn’t understand.
“Because if it’s got to do with this hard on, I think I could help you with that. I’d really like to do that. Would you like me to do that, Tim?”
I mumbled in confusion and consternation some more. He had turned my back into the wall with that tantalizing hand on my belly and still had the other arm against the wall to prevent me bolting in the direction in which I had been going.
“I’ll tell you what, Tim. I’ll do a little fast inventory, and any time I’m doing something you don’t want, just let me know and we’ll go on about our business as if this never happened. If I like the goods and you’re interested, we can just slip into my bedroom right here for a few moments of mutual entertainment. Is that okay with you, Tim?”
My mouth felt like it was full of cotton, and my cock was rising at the very thought of this totally unexpected turn of events. I mumbled something incomprehensible again.”
“I’ll take that as a yes, shall I?” Thad said, and he moved his hand until it loosely covered my tented package. My knees wanted to give, but I braced them by moving my pelvis forward, which Thad took as an affirmative sign.
“Ah, is that your ‘yes,’ Tim?”
“Yes, I guess so,” I managed to whisper.
He moved his hand back up on my lower belly but only so that he could then work his fingers under the waistband of my Speedo. He moved straight down to my balls and weighed them in his hand and then came back up to my cock and measured the length of that. I heard the intake of his breath.
“My God, you’re a stud, Tim. Just as I’d hoped. Is this your full hard?”
“No, I don’t think so,” I replied in a low voice. That disconcerting direct approach again.
“Any objection to going behind this door here for a short while?”
“No . . . No . . . But won’t your guests . . .?”
“Fuck my guests, Tim. My guests know how to amuse themselves in my absence for short—or long—periods. My pool guy might come looking for me, but that wouldn’t be a problem either. So, here we go then.” With that, he removed his right hand from my crotch and opened the door that was beside us and ushered me through with his other arm. He didn’t let me actually move any distance into the room, though. As we went through the door, he closed it firmly behind us and just turned my back to the wall beside the door.
“You don’t have any trouble with fast reloading at your age, do you?”
What a strange question, but I didn’t, so I simply answered. “No, no problems. Rather quick, actually.”
“I thought so. You obviously keep in great shape. I only ask because I’ve ached for you from the first day, and I need to start with a quickie unless that would spoil the fun for what I have planned later.”
“Ached for me?” I asked weakly. If only he knew how close I was to being able to say the same thing about him.
“Yes, ached for you. Ached for you to have a good package, and you’re triple A there. And, if so, ached to have you in me—in my mouth and up my ass. Am I being direct enough with you? Am I clearing up any confusion you might have about the latitude you have with the boss?”
“Yes . . . Thad,” I said weakly.
“The only thing is that the first time, I am completely in charge. Understand? If there’s a next time, we can share the direction more. Understand?”
“Can I kiss you now?”
“Yes, Thad.” Upon which, he took both of my arms by the wrist and raised them over my head and leaned in and gave me a lip lock that very clearly supported his claim to have ached for me. Holding my wrists in place with his left hand, he then lowered his right hand and quickly and very expertly examined my arms and my torso and traveled down to my lower belly and around to my firm, round butt cheeks, pushing the Speedo down below my buttocks. He briefly had his finger on my asshole, measuring the pucker there, and then, with his hand under the rim of the Speedo, he moved around to my crotch, and my dong popped out of the suit. He wrapped his hand around my cock and started to gently stroke and pump it. I cooperated by groaning for him appropriately. His left hand started traveling down my arm, and I lowered my arms, thinking I’d do some exploring on him, but he quickly pushed my arms back up, so I kept them over my head. This stretched my torso out nicely for his exploration. He pulled away from the kiss and my mouth and continued his kissing down the side of my neck, around to under my chin and then to my pecs and nipples. He fairly quickly descended to my sternum and abs, dwelling for a bit in kissing the cleft of my belly, tonguing my navel, and letting his left hand play some follow-up on my nipples and armpits.
This seemed to be a man on a short-deadline mission, though. He didn’t spend long anywhere, but his visit would be fondly remembered everywhere he’d been. He quickly exchanged his hand wrap around my cock with his mouth. He did some quick preliminary work there, seeing how hard he could make me and being pleased with the results. He had pulled my Speedo down and off my legs and had cupped one hand on a butt cheek and had that other hand in that tantalizing place across my belly. Some quick work on my shaft and then he came up for air.
“Very nice. Very nice, indeed. You were right. You weren’t nearly as hard as you could get yet. Now turn and take that stance they talk about in cop shows.”
I turned around, facing the wall, arms above my head and splayed out, steadying me, and my legs spread apart. He almost brutally forced my butt cheeks apart with his hands and buried his face in my butt crack. He was tonguing and kissing my ass, rimming me and pushing in with his tongue and generally slobbering and making me all wet and slippery. I began to pant and moan and writhing a bit in my stance, which only excited him and increased the pleasure of the motion for both of us.
“Now, turn again. Quickly, turn now.” When I turned, I saw that he had pulled his own dong out of the thong he was wearing under that skirt and had been pumping himself as he tongued me. I started to say I wanted to help him with that, but Thad obviously had an agenda and a close deadline. He positioned himself on his knees in front of my right leg and a little off angle from me, but very close into me.
“Your right leg. Over my left shoulder.” I did as he directed, and he snaked his left arm up behind my waist and held my hip to him. During the rest of the operation, my own hands moved around along the wall and to his head and back in an effort to maintain my balance in the face of increasingly rubbery legs. He took my dick back into his mouth and he started pumping, first with short strokes going half way down the shaft and then with deeper throating. Off and on his tongue did a job on my glans and piss slit. I moaned in appreciation and did some minor gyrating with my pelvis. Very quickly his right hand went between my legs, and, with the heel of his hand behind my balls, his middle finger moved to and into my asshole.
“Uh, Thad, I don’t know if . . .” But he ignored me, and the finger went in smoothly enough because of the water work he’d done on it earlier, which both caused it to loosen and had lubricated it enough for me to accommodate his finger without much pain. His finger slid right in up the sphincter muscle, which accepted it, sucked it in, and helped the pad of the finger land squarely on my prostate gland. I gave a little lurch and yelp. Thad’s only response was to plop my dick out of his mouth and my balls into his mouth. He was gently rubbing and applying pressure to the prostate and sucking and extending my balls and thus was working on the root of my semen production plant from both outside and inside. I moaned and twisted and thumped my shoulders against the wall, and panted and begged for relief, but he held me firmly in place at the hip.
Very shortly, waves of pleasure, something that went beyond the normal jacking off and lasting longer, started to flash through my pelvis. I felt like I had to piss, but then that changed to the sensation of precum oozing out of my cock. Thad took that as a signal, and, without giving my prostate relief, he swallowed my cock to the root again and began brutally and furiously sucking me off.
I hadn’t utterly failed to defend against this full-scale attack very long before I huskily warned him, “Oh, God, Thad, I think I’m about to blow. You’d better pull off now.”
I knew he heard me, but he wasn’t having any of that and in short order, I came, sending the semen he had helped produce down his throat. He pulled out then, gave a little cough and, releasing my right leg from his shoulder and allowing me to take my full weight on the ground, quickly kissed his way back up to my mouth. His finger came out of my asshole with a squishy little pop when he could no longer hold it there on his kissing and tonguing journey up my body.
After a deep kiss, he said, “That was great. Now we can take it more slowly. The urgency of the wait is gone now. You are one sweet stud. I knew I was right about you.” He took me by the hand and led me over to a gigantic bed and told me to lie on my front on the middle of it.
“I figure about a fifteen-minute timeout should do it,” he said, and then he scurried around above and beside me on his knees in the bed and began massaging my aching muscles, from my heels and my tense calf and thigh muscles to my back and shoulders and biceps and arms. This alone probably took the fifteen minutes.
“Turn over,” he said. “Ah. Beginning to come back to life already, I see.”
My half hard on was flopping around on my belly. Before he had finished massaging my feet, toes, belly, abs, pecs, neck muscles and temples, though, my flag was back at full staff. As he had leaned over me, I had played with his pecs and abs through the tantalizing straps across his torso and had gone under the skirt and ripped his thong away by snapping the strings on either side. He had given me a big smile and a longing look with his eyes when I had done that and had sighed and moaned when I latched onto a pretty big—and quite hard—penis. While he was fussing around with the rest of my frontal massage, I did what I could to keep hold of his rod. He crawled over to a nightstand and came back with some lubricant and a condom.
He rolled the condom onto my tool, took a big gob of the lubricant in his hand, handed the tube to me, and knelt above me, his butt facing me and his knees close in on my sides. “Here, lather me up, while I take care of this monster cock,” he said. So, while he rubbed the lubricant up and down my sheathed pole, I spread his butt cheeks and lubricated his hole, around the rim and in a good bit, leaving a good-sized gob to be pushed farther into the hole by, I strongly suspected, me. I also took hold of that skirt on either side of his waist and just ripped it down and off him. When that was done, he moved his butt down, positioned his asshole right above my shaft and started working on descending on me. I was squirming.
“Hold still,” he said. “Hands above head and legs spread.” I did as he directed, and he continued to work his butt down into the hollow of my belly. When he had accomplished this, he did a little pumping, but not for long. He then did something that astonished me. He laid back on me full length, his arms extended on top of mine, his hands holding my wrists in place, and his legs stretched out on top of mine. He moved his butt up off my pelvis and a little way farther up my belly and then whispered. “Fuck me. Pump me.” I found that, with a little effort from my butt muscles, I could do that and that the new sensation was quite pleasurable. He was tighter inside now than he had been when he impaled himself. I would have reached around him and stroked his cock for him, but he had me in a wrist hold above my head again.
That’s when and where the pool guy found us. I was later to learn that the pool guy was also the driver guy and the gardener guy and that much of the driving he did was into Thad’s ass and that one of the gardens he was assigned to plow was Thad—regularly. His was a light-skinned black guy with handsome Jamaican features. Lean, but well muscled in the pecs, washboard abs, and bulbous butt. Ropy arteries stood out on his pecs and arms. He was wearing a wild-colored cousin to those boxer silks I should have worn, and I saw that they would not have solved my problem, because as soon as the pool guy came upon Thad and me on Thad’s bed, his trunks began to tent out awesomely at the crotch and the waistband in front was pulled down to where I could see a very formidable cock.
“Ah, Clem,” Thad announced calmly. “Perhaps you could join us. My dick seems to be in the need of attention.”
Without need for a written invitation, Clem grinned and dropped his trou. I thought I might faint. His cock must have been a good ten inches engorged, and, although not thin, its length kept it from appearing to be too fat. It rose up in a little curve near the business end. He wasn’t circumcised and he hadn’t filled out yet enough for his helmet to burst forth, but I could see evidence of a pinkish mushroom cap. The contrast in color between the cap and the cock brought your attention right directly to the business end of the pool boy.
Clem quickly joined us in bed. He straddled Thad in a 69 position and started working on face fucking his cock. Thad did the same for Clem, but I was also available at that angle and must admit that Thad shared Clem with me. No way I was going to swallow that whole, though, I thought. I can’t even image burying it in my ass. All this time I was fucking Thad for a while and then resting for a while.
“Ah, I see what you doin’, Mon,” Clem spoke, and I felt fingers going to my ass. “And I see a tube of sex goo right here, very near,” he went on to say. I felt the coldness of the lubricant as Clem lathered up my hole.
“No, please,” I said weakly. Clem’s only answer was to stand up on the bed, his feet close in at Thad’s and my sides, roll a condom on his rod with great difficulty, and hover there over us, a big grin on his face and his dong looking like a rigid telephone pole. He started lathering up his rod, and I lost all interest in fucking Thad.
“Well, now, I haven’t given you a big island welcome to our house yet, Mon. I’ll take care of that right now.” He back-peddled down to beyond Thad’s and my midsections. I felt my butt cheeks rise as he slid his knees below us, my cheeks resting on his well-muscled thighs. He fingered my ass for a bit with long, thin, sensuous fingers, while I moaned and quietly begged him not to carry through with this. I struggled to bring my arms down, but Thad held me in a strong grip. He also had gotten his ankles wrapped around mine, so that I couldn’t move them any distance. Then I felt the head of Clem’s dick at my hole and he pushed in a good two inches. I moaned and twitched my dick around in Thad’s ass, which made him moan as well.
And then I felt both my legs and Thad’s being lifted and wish-boned out and then Clem started the long slide into me. I felt this descent had gone on for several minutes and that he must be nearing my stomach. He did a little languid pumping there, and the sensation of his uncut foreskin through the ultrathin and stretched sheath against my ass channel walls was quite new and pleasant. Even if he hadn’t declared himself, I might have called this fucking style the “Jamaican Welcome.” He slowly pulled his rod out with a sucking sensation and then came back in just to where he could feel my prostate with his bulbous now-extended mushroom cap.
He rubbed that with his dick head until I came inside Thad in the peaceful release of flowing semen into the expanded bulb of the condom, after which Clem slowly went deep again and fucked me slowly and deeply with that loose-skin feel for several minutes before giving a series of little lurches that told me that the Jamaican Welcome had been achieved, upon which, with a grunt and a sigh and Clem had collapsed on top of Thad and me.
When we had caught our breaths, Thad bounded up off the bed, headed for the door, and told Clem and me to meet him at the shallow end of the pool. With a sigh, I struggled off the bed and hobbled toward the door in a rather bowlegged gait, with the aid of Clem’s spread hands on my butt cheeks. I was beginning to realize that my new boss was going to be a real taskmaster.