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Caught With My Sister's Boss

by Joel Daley


It was just an accident that I decided to go that restaurant for lunch. I didn't even notice them at first until I'd already passed the table where my sister and her boss were having lunch. "Joel, is that you?" she called from behind me, and I turned around to recognize the two of them. Her I adore, him I despise! Okay, perhaps despise is a bit strong, but I really don't like Charles Crandall especially because he insists that I call him Chuck. Crandall is more than Dee's boss, he's also her boyfriend....at least when he's in town. There's no chance that he'll ever marry my sister because he can't afford to divorce his wife who technically owns the company he runs. She must know how many women he has strung across the country. My sister's not his mistress or anything. He doesn't pay for her apartment, and she got her job on her own merit long before she ever met him. She insisted that I join them and then immediately left to go to the ladies' room, leaving me all alone with her jerk boss/boyfriend. Chuck, in his typically macho persona wanted to talk football, specifically college football. "Dee tells me you were an athlete in college" he said, and I told him that I had indeed gone through school on a full ride for swimming. "Oh I see....I thought you were in a real sport" he said, not even realizing what he was saying was completely outrageous. It was totally in keeping with his character. What a ass-hole! Thankfully my sister returned to the table and I could see that they were ready to leave even before I had ordered. "No go on, really!" I said, suddenly realizing that if he'd just gotten to town they were probably anxious to go somewhere and have sex. "How long are you hear Charles?" I asked, emphasizing the name just to aggravate him. "Until the day after tomorrow" he replied, adding that Dee had meetings all afternoon the next day but that he was free. "How about a racquetball game at the club around the corner from here? It'll give me an opportunity to see what kind of athlete you really are". I almost told him to go fuck-off, then decided to take him up on his offer. Hell, the man was in his late forties, was mostly bald, had grown children and even a couple of grandkids. I figured I could take him and maybe shut up his god-damned bragging a bit. "Sure, you're on" I said, and we made plans to meet the following day at 12:30. "Loser buys lunch!" he said. "And the winner buys drinks" I countered and we shook hands on it. There were two things I noticed during that challenge hand-shake. The first was how strong Chuck Crandall's grip was. The second note- worthy thing was just how thickly coated the backs of his hands were. I've always been attracted to hairy men, and up until this very moment I never noticed how dense his hand-coating was. I got to the club before him the next day, was all changed and ready to go before 12:30. He was a little late and apologized by saying that my sister wouldn't let him out of bed that morning. Jesus, even when he made an apology it sounded like he was bragging. I have to admit that for a guy close to 50, Chuck was in great shape. He must have a regular regimen of exercise to maintain his physique so well. He wore canary yellow shorts and a bleached white t-shirt with short sleeves that exposed plenty of his very hairy arms to me. His legs were likewise beefy and also very densely haired. I beat him the first game, 21 - 3 and felt pretty smug about my victory. Even the first five points of the next game were mine, and then I noticed something that truly distracted me. As I stood behind him, I could see that Chuck had a line of sweat running down the back of his shirt right into the top of his shorts. It gave the appearance of trickling from the center of his wide shoulders right down into the crack of his ass. No matter how hard I tried to ignore it, I couldn't keep my eyes off Chuck's well-packed sweat-streaked back-side. The next seven points were his, and then he did something that gave him a truly unfair advantage by pulling the white t-shirt up over his head. This was against club rules, but no one ever enforced them. For the sake of my game it would've been better to have the attendant come by and tell him to replace his shirt. As it was I couldn't concentrate at all any more. You see, Chuck Crandall was about the hairiest brown-bear guy I've ever seen. The stuff I'd noticed on the backs of his hands the previous day exploded it's way up his thickly muscled arms, up across his broad shoulders and then spilled down over both his chest and his back. He got all the rest of the points that game and completely skunked me in the last game. "Aha, you had me going that first game but I knew I could beat your ass!" he scoffed, and I was tempted to accuse him of doing it by cheating, except I couldn't admit to him that seeing him without a shirt had caused me to lose my concentration completely. We showered in the locker room that had separate stalls for each of the patrons. I was almost glad not to have to share a common shower area with him for fear that I'd throw a rod and give away my attraction to him. On the other side of that though was the fact that I didn't get a chance to see him completely naked....except for a few seconds when we both dropped our towels and dressed. I tried not to make it obvious that I was sneaking a look, and it almost looked as if he was doing the same with me. I knew I had no reason to feel inferior to him (or to almost any guy) in terms of size, but the fact that he was so, SO hairy made me feel somehow less manly than him. "So were are we going for lunch, you're treat by the way?" he said, rubbing in the defeat. "I'm still thinking" I answered, then turned it around and inquired as to where we would go for drinks. "Let's go back to your sister's apartment and break open that bottle of Scotch she's got in the cabinet. That girl's got great taste.....in everything!" he said, making it sound once again that he was boasting. We pulled up in front of Dee's building and Jerome, the doorman greeted us. "Good afternoon Mistuh Joel, Mistuh Crandall" he said, and we both said hello. "Just a minute, I'll be right in" Chuck said, and I saw him stop to give Jerome a $10 bill and said something to him. Once in the apartment he headed for the liquor cabinet as if he knew exactly where everything was. Of course he did, since he spent all his time in town at Dee's place. He poured us both a double - mine with ice and his straight up and we each drank a big slug of it. "Wow! This is good!" I said, and he reminded me that my sister chose only the best of everything. He raised his glass and toasted me and somehow spilled some of the stuff on his shirt. "Oh damn! Guess I"ll have to change before we go to lunch. Or maybe I can just run some water over the spot and throw it in the microwave for a couple of minutes". "Maybe the dryer would be safer" I suggested and he started to peel the shirt off. Oh shit! This was just what I wanted, but didn't need to have him do. "Something wrong?" he asked me, and I asked him what he meant. "I'm talking about that big hard-on you've got running half-way down your pant leg!" he said, and I realized he'd noticed my reaction to his bare top. It didn't take long for each of us to decide what to do. I ran my hands all over the thick blanket of brown fluff that completely covered his well-built chest and surprisingly muscular belly and he boldly traced his hand over the surface of my fully hard cock. I tasted the scotch on his tongue as he shoved it deep between my lips and I wrapped my hands around his back to pull him closer to me as we indulged ourselves in a good long time of mutual tongue-sucking and general groping. We didn't say much to one another....didn't have to...to indicate that we both wanted the same thing. "You said you'd provide the lunch" he said finally when we broke our long open-mouthed kiss. "How about if I eat that big sausage hanging between your legs. Shit, I've been waiting to get my mouth on that thing since I saw it back at the club!" He dropped to his knees and deftly loosened my pants, allowing them to fall down to the floor. Then he ran his tongue over the surface of my thick ten-incher while it was still encased in my Calvin Klein's, leaving a trail of moisture on the surface of the silk material. Soon enough though, he managed to tug those off and my fully hard cock flopped out and slapped him on the face. He lunged forward and took the first half of it into his mouth right away, surprising me with his expertise. After that he would back off and press forward with an almost rhythmic pulse until he had somehow managed to take the whole thing into his mouth. Not many guys can do that, but for Chuck Crandall it seemed to be an easy chore. He massaged my cock head with the muscles deep down in his throat and before I could let him know I was losing control, I'd lost control. I exploded into his face and he miraculously managed to swallow every hot jettisoning bit of my spew. I reached down and grabbed him under his hairy arm-pits, pulling him up to make our faces meet again and we kissed again. This time I could taste my own spunk mixed with the flavors of the scotch. "Your turn" I said, and he told me he'd prefer to have his ass eaten "if you don't mind" he added. The moment my face touched Chuck's hairy ass I was hard again and when I dug my tongue deep up his chute, chewing and slobbering on the tight muscle-ring of his ass-hole he moaned and writhed and grunted and groaned. Eventually he told me he wanted to be fucked by my big horse-dick and I did what he asked, with him bent over the edge of the new sofa Dee had just gotten installed in her living room. Having already come once (okay and twice earlier in the morning before even going to the health club after I'd just thought about what he might look like based on the hairiness on the back of his hands) I knew that this time I'd be able to hold off a lot longer. I must've fucked him for half and hour, and it wasn't easy-going and sensitive. No, this time I fucked him like two animals in heat, pounding the full length of my hard organ into his hairy ass-hole and making him shout out in pain and delight. Some guys (really hairy guys) sweat a lot during sex, and Chuck was one of those. "Let's move to the bedroom" he suggested, and I felt almost guilty having sex with him in my sister's bed. Not guilty enough to turn it down, but still felt a little funny. Her bed looked like a god-damned battle zone, with puddles of crusted cum and stray hairs that he'd lost during the previous night and morning of sex with her. Damn, there were more hairs on her white sheets than I even HAVE on my body. Like I said, I was able to hold off for a good long time and I told him that I wanted to be on the receiving end of his cock for a while. He's not so hugely hung as me, but any guy as hairy as Chuck Crandall could have a little stub of a cock and I'd be happy making it with him. Trust me, Crandall had considerably more than a stub, and once it was fully up inside my hot and horny butt it felt like it was getting bigger and bigger. "Take it you cock-lover, take my dick up your ass!" he said, and we both exploded simultaneously....him up my ass and me all over his hairy front. We'd been so involved and were making so much noise that we never even heard Jerome's call on the intercom from down at the front entrance warning us that Dee was on her way up. The reaction of my sister's son-of-a-bitch boyfriend was astonishing when she walked in and found us in her bed with my dick buried up Chuck's hairy ass-hole. "It wasn't my idea honey, honestly! This faggot brother of yours damned near raped me after he talked me into coming back here and drinking that expensive bottle scotch you bought!" "You lying piece of shit!" I shouted at him, realizing that my cock was still hard as a rock up his hole and there was no way I wanted to stop doing what we'd been doing all afternoon, with or without my sister watching us. Something told me that Chuck felt the same way, because he made no effort to pick his body up off my straight-up ten-inch dick. I looked down and noticed that his dick was oozing out this big pearly drop of pre-cum and I wanted nothing more than to touch my tongue to it and lap it up. "I see that my little plan worked!" Dee said, grinning smugly from the side of the bed and we both looked at her with wonder. "I could tell from the first time you two guys met back a couple of years ago that you were hot for one another. Hell the way Chuck pretends to be this big jock-athlete in front of you and the fact that you've never been able to turn down a guy with lots of hair all over his body....." Jesus, I had no idea my sister even knew I was gay, much less what kind of guy appealed to me. "You may have paid Jerome $10 to warn you if I came home early, but I paid him $20 to keep his mouth shut until I was almost inside the door. Go on guys, finish what you've started and don't mind me at all. I'll just sit here and watch and maybe join in the fun later on...." So there you have it. This "getting caught" story has a different ending than most of them doesn't it. No one's getting divorced as a result, nobody's pissed off at anybody else, and nobody suffers any pain or humiliation because of it. Well, at least not yet. It was perhaps a year later that Chuck and I were "accidentally" on the same cruise ship in the Bahamas. He didn't dare ask Dee to come along since his wife was going to be there. Still he figured it would be safe enough to have me aboard and we could meet as often as possible. Yeah, you guessed it. His wife walked into my cabin by mistake (he'd booked me a cabin directly above theirs and she was on the wrong deck) and caught the two of us going at it. It was the end of Chuck's career, the end of his marriage and the end of his happy (?) family. It wasn't the end of him and me though, and now it's more often the case that Dee is the visitor who comes to watch her ex-boyfriend having sex with her younger brother, with Chuck as my full-time, live-in lover.

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1 Gay Erotic Stories from Joel Daley

Caught With My Sister's Boss

It was just an accident that I decided to go that restaurant for lunch. I didn't even notice them at first until I'd already passed the table where my sister and her boss were having lunch. "Joel, is that you?" she called from behind me, and I turned around to recognize the two of them. Her I adore, him I despise! Okay, perhaps despise is a bit strong, but I

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