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I had become a regular at the gym on Tuesday nights, and this 40-something businessman named Clint, who was also a regular on that night, and I had gotten to where we regularly spotted each other through our bar bell work. He was in great shape for his age, leaner than I was, but with well-defined, ropy muscles and chiseled square-cut features. I'd been trying to save the money for some time to get out to the beach for a couple of weeks to cruise chicks with my friends, but emergencies kept cropping up and I didn't seem to be able to set money aside. Finally, I had gotten down to a week before my friends were going, and I still didn't have any money for that trip. I must have been moping around about that during my Tuesday night workout, because Clint noticed that I was withdrawn.
"What's the matter, Ben?" he asked, as he was spotting me on the weights. "You don't seem yourself this evening."
"Naw, I'm okay," I answered. "I just have this problem where I'm supposed to go to the beach with my friends next week, and I don't have the money to go."
Later, as I was dressing after my shower, Clint sought me out and said he thought he knew how I could get the money I needed for the trip. He invited me to stop by his house after I was finished at the gym and we'd discuss how maybe we could help each other out on a little business proposition. I said, sure why not. He gave me his address, which was in a swanky part of town, and I followed his car back to his place.
We entered the house and he suggested we go to the kitchen, where I leaned back into a counter, with my hands spread out on the surface, while he broke out a couple of beers and some chips. He brought the beers over, handed me one, took a swig from his while I did the same with mine, and put one his hands on the counter beside me.
"So, what's the possible business deal," I asked, a little nervous, because he was standing pretty close to me. Clint put his beer down and then placed his other hand on the counter. Both of his hands were closer into my body than mine were, so I was pretty much stuck there, facing him pretty close.
"You are, Ben. You are the business deal."
"I . . . I don't understand, Clint. What do you mean?"
"You want to go on this trip pretty bad, don't you, Ben?"
"Well, yeah. It's about all I've been thinking of for a couple of months."
"And you'd pretty much do anything at this point to get the money to go short of robbing a bank, wouldn't you? You sounded pretty desperate when you were telling me about it back at the gym."
"Well, yes, I'd work pretty hard."
"Well, I wouldn't work you all that hard, Ben. And I'm sure you'd enjoy it even though you'd be leery at first. But I'm sure you'd like earning the money."
"So, what's the business deal, Clint?" He really had me wondering here.
Clint paused for a minute, picked up his beer, took a swig and put the beer can back, and repositioned his hand. Then he posed the killer question in a low, husky voice. "Ever done it with a man before, Ben?"
I was shocked and getting a little shaky. But I guess I shouldn't have been surprised. Those workouts in the gym; Clint had looked me over pretty good and sometimes I felt he had his hands on me when he was spotting a little longer and more personally than I thought was necessary. I had never said anything about it, because I guess I found him attractive and I had gotten a little electric charge out of the attention and touches.
"No." I managed. "No, and if this. . . "
"We can make this very easy for you, Ben. I have no idea how much money you need, but we can discuss this in terms of levels, and you can stop it at whatever comfort and need level you want. Doesn't that sound fair and attractive?"
"Levels?" I said.
"Yes, levels," Clint repeated. "Say, $20 for each kiss for openers. $50 if you take off your shirt and let me do any feeling I want above the waist. Another $50 if you let me feel you below the waist through your pants, but $100 if you let me feel you skin-to skin below the waist with your pants on; $150 if you let me strip you down to the floor and feel."
"Uh, I don't know, Ben." He came in closer to me, up against me in front, and I could feel a hardness against my crotch.
"An easy $90 bucks with your pants on, Ben, and at least $190 just for harmless feeling. Neither a hand job or a blow job would be included in that. If you let me get you off by hand, that would be another $100, or if you let me blow you, that would be another $200. We're already up to over $400 with a few added kisses, Ben, and we haven't really done anything yet any straight man wouldn't do. I don't know how much money you need for this trip, Ben, but I do know you are thinking about this hard, because I can feel you getting harder. During any of this time, you can do what you like with me, no deduction for that."
I was betraying myself. I couldn't help doing so, and Clint could tell I wasn't totally turned off by this proposal. Indeed, the money sounded good, and I'll have to admit that I was both curious and attracted to Clint.
"And, then, if you fuck . . .," Clint started again. But I brought a finger up to his lips.
"Let's not go farther into the menu just now, Clint. Let's say I'll take it through to as long as I keep my pants on and then we'll see where it can go from there.
Almost as if he was afraid I might change my mind, without arguing Clint brought his lips to mine in a short, sweet kiss. And it was sweet. I didn't realize that another man's lips could be so sweet. He pulled away and looked intensely in my eyes.
"The first $20," I said, with a little grin.
"God, that's right," Clint said. Each of those is costing me. I'd better think more about getting my money's worth, don't I?"
With that, he came back in for another kiss. He got his top lip between mine and pushed my lips apart so that my mouth was open to a deeper kiss. It felt surprisingly pleasant. He gave me a little buzz and I felt both my cock and Clint's react to the intimacy. He hands went to my waist, and he pulled my T-shirt up to under my armpit. I wondered why he didn't pull it over my head, but then I remembered the ticking of the cash registers and figured he didn't want to end that second kiss too soon. The thought made me grin, which Clint took as affirmation of the kiss, and he pushed my lips farther apart and got his tongue in my mouth. I gave a little lurch not only from that, but from feeling his hands encase my bare waist. He slowly pulled his hands up my sides, his fingers stretch out so that he covered a good deal of skin on his way up. He stopped when he got to my pecs and worked his fingers through my chest hair until his hands felt both of my nipples, which he rubbed, sending little shivers through my body. His crotch was pressing into mine now, and I could clearly feel his desire through the multiple layers of material. His hands came back out to the side and went up to my armpits and then up to my upper arms, pushing my arms up over my head. He stood there momentarily, lessening the strength of his kiss, making it tender once more, while he held my wrists back against the upper kitchen cabinets with his hands and pressed his crotch into mine. He ended the kiss and brought his mouth down to nuzzle the artery running up the side of my neck. That gave me a little twitch down in the crotch.
"$90 already, I said, "Although I don't think the mouth work on my neck was included in the deal."
"The deal was that I could feel you as much as I wanted above the waist at this level; it didn't specify what I'd be feeling you with."
"Point . . . uhh . . . taken," I croaked. My stutter had been caused because his mouth had moved to a nipple and he was nibbling quite disconcertingly on that. He moved his hands back down my arms and around my biceps, and I started to pull my arms down, but he quickly lifted them back up and stripped my T-shirt off, and I got the message that he wanted me to keep my arms above my head. This served to stretch out my torso. His arms came back down and me brought his thumbs to my nipples and spread his other fingers up toward and into the hair at my armpits. His mouth headed south. With kisses, nibbles, and lickings, he came down my chest and belly. He stopped briefly at my navel but then continued down my lower belly. To his advantage, I was wearing low-riding jeans, so he managed to get to just the top of my pubic hair. Even at that, he got his tongue under the waistband and tantalized me with what he did at the crease at the upper edge of my pelvis bone.
"Whoa," I said. "Not below the pant line, per agreement." He had moved his hands down my body as he tongued his way down and now had them on my upper thighs.
"Ready to make some more money?" he asked.
"I don't know. I don't know if we should go any farther."
"You've already agreed to the next two levels," he said. "It would be breaking the deal to back out now. Nothing has really been done before we get to the end of that part of the deal, where you no longer keep your jeans on. You've just got some money and you don't have to admit to anything life altering." He had already brought his right hand up to where it was lightly covering my package. "So, are you ready to add to the cash register."
"Yes, I guess so," teased mightily by that hand covering my cock.
But at that point, he stood back up and backed off a bit. He slowly unbuttoned his shirt and pulled it off his body. Then he pulled his undershirt over his head. He was in great shape for a man his age, as I knew we was because I'd seen him work out shirtless before. The thick veins running through his pumped-up muscles gave me a slight thrill. His pants were really low-riding and must have been kept up by that tented bulge I could see right below the beltline. He leaned into me, our torsos skin on skin, and I felt his hand return to my crotch. He brought his mouth to mine for another lingering kiss. His hand at my crotch became more active. He increased the pressure, moved about more rapidly, and, when he had traced my engorging cock and found my balls, he began to clutch and rub in a way that was driving me crazy. I began to moan, and my pelvis seemed to take on a life of its own, moving in a slight grinding motion. He pulled away from the kiss, and his tongue traveled down along my neck and into my right armpit.
"$270, I squeaked."
"Doesn't get you too far, does it. You'll be wanting to know what big money is. And speaking of big . . ." he had the flat of his hand on my belly, and he was working the fingers of his right hand under my waistband and crawling through my pubic hair."
"Shit, these jeans are just too tight," he complained. And then he must have unbuttoned my jeans and quickly pulled the zipper down with his left hand, because suddenly I felt a release of the constriction at my crotch, and felt Clint's right hand slide down onto my dick. He wrapped his hand around my dick and then continued on down to the head, and then on down to weigh my balls. I could feel him catch and intake his breath, and found that this gave me a little thrill of pleasure, just as it did when the ladies got to the point of realizing what going to slide into them.
"Oh, God, Ben." Clint whispered huskily. "What a package you've got. What are you? Eight, nine inches?"
"Nine," I said, with some pride.
"And these balls. Like cannonballs."
"I'm glad you approve. But you know, you've just gone to $370 and beyond. You were supposed to stop with feeling what you could with the jeans on. You've gone beyond that. Uh, oh, God. Gawd!" His hand was flying all over my prick and balls, and his fingers played in my pubic hair. "Stop that, I said weakly. We hadn't gotten to hand jobs, yet, either."
"Technically wrong on both counts," Clint said breathily. "First, your jeans aren't off yet. I admit I miscalculated on being able to get between them and your cock, but between the tightness of the jeans and the gigantic proportions of your cock, I had little choice but to make some room. But technically, your pants are still on. And, second, this, Ben, isn't a hand job. You'll know when you get a hand job from me, and don't you think you want that now, especially because we're about to get into the big money offers?"
He had me panting. I still had my hands over my head, but it took effort to keep them there. I guess I thought as long as they were there, I wasn't really participating in any of that. But they were feeling like lead. I had the urge to reach out and touch him. And I knew I could if I wanted to. He had made clear that I was free to put my hands on him if I wanted.
He didn't misread my hesitation. He pulled back and unbuttoned his pants. "Here, maybe this will help you decide. This is all harmless. This doesn't mean you can't do it with the ladies; it just means you are one sexy guy; one sexy guy with a cock that any woman or man would love to get their handsand other body partsonto."
With that, he dropped his pants, and pulled off his briefs and his shoes and socks and stood there, naked, in front of me. He was magnificent. Wiry but perfectly ropy muscled and proportioned, fiery red hair at his crotch to match that on his head, and his dong wasn't his smallest of muscles. His might be as long as mine; it certainly was thicker and it had a slight curve to it when hard, as it most certainly was now. My quaking arms went out to him and our bodies crashed together. We went back into a lip lock, this time my lips spreading on their own volition and my tongue meeting his. His hands spread under my pants at the hips and he pushed the jeans down my thighs. His hands wrapped themselves around my butt cheeks. For the lack of originality, my hands went to his thin butt. His hands were roaming my more bulbous, but well-formed butt. When our crotches met, our dicks crashed into each other and were both forced up and between our bellies, side by side. Clint brought one of his hands between us and encased both of the cocks. We rocked back and forth momentarily and then leaned back into the counter.
Clint exited the kiss and buried his face in my neck. I heard him say in a low voice, "Up to $520 for dropping trow, even though we haven't finished that yet, and I'll give you a bonus for the kiss, so let's say $550. Do you want to move on to the hand job? $100 for that, but $200 if you let me finish it in a blow job."
"Yes, yes," I whispered. "That far. I can go that far." My hands were traveling along his back and shoulder muscles and then moving to the front and feeling his pecs and abs, admiring the work we'd done in the gym.
"Yes to what?" He whispered.
"Yes to it all so far. Suck me. You can suck me."
"There's a caveat," he whispered into my neck.
"What?" I said.
"We won't get to the big money unless you feel me too. My dick is aching for your touch. It would mean nothing to you, but it would make the money worth it all to me."
I tentatively moved my hand down to his waist, and he pulled his pelvis away from me slightly and moved his hand away from our cocks and down to cuddle my ball sack. I slid my hand across the top of his thigh and through his pubic hair to his cock. I'd never felt a cock before. It felt both hard and flexible at the same time. I slid my hand along it and to the knob, which I cupped in my hand. Clint sighed and, putting the heel of his hand under my balls, he spread his fingers to where they wrapped themselves between my legs, with the middle finger resting on the rim of my asshole. He was hunched over, licking and nibbling on my nipples. I pushed back his foreskinhe was uncircumcisedand ran my fingers around on his glans, rubbing and squeezing. He was producing precum, which I swirled around his dick head. He moaned and bit at my nipple, which caused me to moan in answer. I rubbed and stroked the length of his cock and then moved my hands to his balls and weighed and pulled at those. His middle finger had gone beyond the rim of my asshole; it has pushed its way in by a fraction of an inch.
"No, not that," I said. "We agreed to feeling on my body, not in my body."
"So sorry," he answered, as he pulled the finger away. "I'm getting ahead of myself; maybe later."
I was still contemplating this, as I felt both of his hands go to my cock. He firmly wrapped the fingers of one hand around the root of my cock, but his thumb applying pressure to the artery running into the cock, which made my dong harden right up. He wrapped the other hand around the cock, near the base and slid it up to the glans, which he played with much the same way I had played with his, and I also produced precum that helped slicken up the rubbing. Then he started stroking my cock. Slowly at first and then more rapidly, but always deeply and in a rhythm that felt both insistent and determined. I gave out little gasps and braced myself against the counter with my hands. This was a bigger high than I'd ever gotten from the ladies. Clint's tongue went to my right armpit, and then he slowly tongued his way down and across my pecs, giving my nipples a nip en route and then up to my left armpit and down my left side to under my pecs and over to my sternum.
He stopped here, and in a low voice said, "It's coming. It's coming to swallow you."
I shivered and he slowly worked his tongue down my sternum and across my abs. He stopped above the navel and whispered again. "Suck, suck, suck, I'm going to suck you dry." His tongue went into my navel and his teeth nipped at the rim. Both of my hand went to the back of his head and ground him face into my stomach. The tongue went down, circled the lower belly, running along the pubic hair line.
"Good, look at that cock," he whispered. "A gigantic tool. I'd love to have that rammed up my ass. Well, maybe later. Workin on the current deal now. Sucking you dry. Giving you no mercy. This is something no woman's going to do for you."
I was already shuddering in anticipation when he let go of my dick with his hands, and his tongue slid down the length of my cock and he licked around the rim of my glans. But then I felt his hands at my hips and he was standing and rotating my body around until I was backed up to a butcher-block topped island of a good size. With a sweep of his hand, he pushed all of the little doo-dads that had been on the top of the island off onto the floor and away from us and he lifted me and laid my back onto the island top. I heard him open a drawer and fiddle around in it, but then he reached back for me and off came my pants, my shoes and my socks and he was pushing my knees up toward my body. He had one foot in his hand and was giving it massage and his mouth was giving suck to the toes of the other foot. There wasn't much I could say. This would have been allowed earlier in the deal. He tongued his way up my legs, first doing the calves alternately and then the thighs, keeping a grip on my feet with his hands. His tongue went briefly between my butt cheeks and across my asshole, which made me lurch and try, unsuccessfully to free my feet, but he moved right on to my balls, which he tongued, sucked, and munched until my groaning and moaning was beginning to alarm me. He released my feet and his hands went to behind my knees in a strong grip, where he held my legs, still folded into my body, but pushed a little outward. Then his mouth moved up to my dick, taking it initial in only to the rim of the glans and playing with that with his teeth and tongue, and then he started swallowing my cock slowly. I went up on my elbows and watched my dong disappear down his throat. In, in, in. The double reference, both seeing it and feeling it, was deeply pleasurable. When he had it in all the way to the root, he held it there for a moment and then he started deep-throating me. Swallow to the root and withdraw to the glans, tongue the piss hole and then slide back down all the way to the root. He kept this up until I was going wild, clutching at his head, burying my fingers in his hair. He lifted his head once to ask.
"Any of your ladies do this for you, Ben?"
"No, no, no," I acknowledged in reply. "But, God, Clint, I think I'm going to cum."
"Isn't that the idea?" Clint said, and then he was back at my dick with a fury. And I did, indeed, cum, with a great spurt of relief, down Clint's throat. I flopped back on the island top, exhausted from the tension and the great relief. I threw my arm across my face and gloried in having had so much pleasure in earning $750 in a single evening. I need never tell anyone about this, but I wouldn't forget about it either.
But I was reveling in a false ending. Clint wasn't finished yet. His mouth had gone straight down to my butt. He was still holding me under my knees and he pushed my legs farther out and was kissing and licking my asshole. I came back to the real world in a hurry then.
"Clint, no. This was great, but we're at $750 and that should do me. I never intended to go this far even."
"Do you?" Clint raised his head until our eyes met. "Precisely. I want to do you, Ben. You're beautiful. You can't just break it off here."
"No, man. This is enough. I . . ."
"$250 for a fuck."
That almost took my breath away. "Another $250? Uh, sorry, Guy, but . . ."
"What's the problem, Ben? You've already been with a man now. It's nothing new. Thousands of guys do it. And thousands of guys continue doing women too. There's some pain, of course, especially the first couple of times. But the pleasure is beyond anything you can get from a woman. The worst that can happen to you is that you'll never again enjoy a woman as you do a man. Listen, $150 for a prostate massage and another $200 for a fuck. That's $350 more."
"No, sorry . . . what's a prostate massage?" This was probably a question I shouldn't have asked.
"There's nothing queer about that," Clint responded with a tone of irritation in his voice. "Doctors do it for guys all the time, and the guys pay, and it's all okay with everyone. They give prostate examines all the time by sticking their fingers up your ass. With a prostate massage they just leave it there for a while and get your nuts off. Don't you know that woman aren't the only ones with G spots. The man's prostate is the same thing; some men build up so much sperm that they have to be milked by a doctor routinely. Massaging the prostate eases the pain from sperm buildup, and the pleasure of getting yourself off this way can be greater than a straight fuck. Come on, it's obviously a new experience for you, one that you could get with a prescription, and it doesn't mean you're queer. Okay, last offer, both for an added $500."
I gulped. "Well, the prostate thing doesn't sound too . . ."
Before I had finished, Clint's mouth was back on my asshole and he was kissing and tonguing the rim. I squirmed a bit when the tongue pushed slightly into the asshole.
"Gotta loosen you up down here, Ben, so that it's all pleasure and no pain when I insert to reach the prostate. I'll have to use some lubricant. It will help friction and will help relax you. You're too tense, you need to relax."
"Okay," I said, "I'll try." It must have been lubricant that he'd taken out of the drawer earlier, because I felt a cold glob of jell at my asshole. Clint was spreading it around and rubbing it in with his fingers. Almost immediately I felt myself relaxing down there and loosening up. He tentatively penetrated the hole with one well-lubricated finger, and it didn't feel so bad. He held the finger there near the entrance, waiting from the lubricant to take its full effect.
"Here," he said. "Let's get in a better position. He hoped up on the island top with his left butt cheek and stretched my right leg up and behind him. He was leaning on his left arm above me. His heel of his right hand nuzzled up under my balls as it had done before, when I intended never to go this far, with his middle finger draped between my legs and at the entrance of the asshole.
"Can you get your other leg out to give your ass as full an opening as possible?" he asked. And I lifted my leg and found I could dig into the island counter edge with my heel. It was a good thing I had done flexibility exercises while I was in the gym. Clint stared intently into my eyes and I locked mine on his. He was giving me a reassuring smile. I wasn't all that reassured.
"Hands over head," he said. And I complied, stretching my torso out. His finger inched into my hole. At first I thought it was going to hurt, but it didn't. And when it didn't, my whole body relaxed. Feeling that, Clint's finger went in to the sphincter muscle, where there was an initial tightening up, but then I loosened again and it seemed that the sphincter was actually pulling the finger in until Clint could feel the hardness of my prostate. I could feel that he'd reached the goal as well, as a shiver of sensation went through my body.
"Found it," Clint said, with a grin. "First time. I'm a pro at this. It will take some time now, but you should start feeling something new. You'll feel like you have to piss at first and something will come out, but it will be sperm. You've had time to build some more up, young strapping stud that you are. Just let it flow and enjoy the ride." I could feel the pressure of the pad of his finger on my prostate and then he started the massage parta gentle rubbing, circular and up and down and back and forth, always with a pressure on the prostate. As he said, I began to feel like I needed to piss and I could feel precum dribbling out of my hole. But along with that came increasing waves of pleasure. Not quite the same sensation of pumping a woman with my cock, but somewhat the sameand perhaps even more pleasurable. And then I came again; this time quietly and in a soft flowing of cum rather than the usual fountain spurting. I felt weak and satisfied and fulfilled.
Clint removed his finger, took my leg out from behind his shoulder, and leaned over and sucked my cock dry. I let my other leg fall down over the side of the counter. Clint then stretched out beside me. His left hand went up to the arms I was holding above my head and he entwined both of my wrists in his. His other hand wandered around my torso, stroking and rubbing, while his face was buried in my arm pit. I began to doze. It had been a profitable night. I'd made what, nearly a thousand dollars? I couldn't quite remember what the total was, because it was a little confusing now what the deal was. I was lost so deeply in thought that I didn't pick up on Clint's next move quickly enough to do anything about it. The lubricant wasn't the only thing he'd taken out of the drawer. He suddenly had some sort of leather strapping in his right hand and he had pushed himself up and expertly lassoed my wrists that he'd been holding in his other hand and then tied the other end to some handles on the other side of the island. I was trapped then.
"Clint, what are you doing, man?"
"$500. Just keep thinking of that $500, Ben. You're driving me crazy. I've got to fuck you, man. I've got to have my cock in you. I've dreamed of this for so long. I'll keep to the agreement, but I'm doin' you. No more coy talk. If you scream, I'll gag you."
"Clint, no, no. I don't want the $500. Just what you already owe me. Let me loose." I would have tried kicking him, but he'd already strapped off my legs to the door handles on the near side of island. He'd used long leads, though, so that my legs had full maneuverability. He just wanted me to know I wasn't going anywhere soon with them.
"I don't want to hurt you, Ben. I want us to do this all again someday. I just have got to have you. I can be as gentle as possible. Just quiet down. He was stroking and rubbing me from belly down to dick and inside my thighs. I was beginning to calm down, when I saw the dildo in his hand. It wasn't as long and as thick as his own dong, but it looked intimidating enough. I looked on in horror as he lathered it up with the lubricant. Clint looked at my eyes and saw the fear.
"You mean you're lady hasn't even done this for you? Ben, Ben, Ben, you're going to want to switch over to the pleasure side now for sure. And don't worry," he added. "I'm not doing anything terrible with this. This is just to prepare you for the real thing. You definitely would feel the pain if I just went up your ass now. This will loosen and open you up." With I felt the head of the fake cock at my hole. It went in an inch or two and Clint stopped to let me accommodate it. He rotated it around a bit to help open me up. My hole complied, and once again my sphincter muscle picked it up as it pushed farther in and pulled it on end.
"Good. At least three inches. You should feel it against the prostate again. Stud like you should be producing milk again already." And he was right on both counts. I could feel it rubbing on the prostate, felt like pissing again, and felt the sperm start to rise. Clint's free hand went to my cock and he rubbed the cum around my glans and slowly stroked my piece. I swallowed hard as I felt the dildo slide in farther than Clint has penetrated with his finger.
"Four. No, now five inches. Very good, buddy." I was panting and felt like I had to take a shit.
"Six inches." My intestines were trying to reject the foreign object. Short pants. Clint stroked my chest and belly, calming me down. The lubricant was taking greater effect. The spasms in my colon died down.
"Seven inches." That's as big as this is. I'm afraid I'm a little bigger, but this is the best I can do for you. Needs to be wider too, though." And I felt him start to rotate the dildo around in my hole. It had a curve to it just as Clint's did, and I could feel the head massaging my colon walls as it rotated. The pain, pressure, and feeling of being stuffed began to subside, and Clint could feel me relax. He slow pulled it out in a screwing motion.
"Brings a whole new meaning to screwing," doesn't it, he said. Then the dildo was out, and Clint's hand was off my lower belly. He stood back from me, and then I saw him open a packet and rolling a condom onto his stiff prick. There was no doubt where this was leading. Then Clint stepped back up to and his hands were on both of my hips, pulling my butt down and over the edge of the island. He had kicked over a small stool and there he was hovering over me.
"No, Clint, no," I said weakly, all my defenses gone. But he wasn't listening to me. He took my right leg in his left hand on the calf and lifted and spread it. With his right hand, he positioned his dick head at my asshole. I felt him push in to the rim of the glans with a grunt. The dildo was a piece of cake compared to this. I was panting again and was bucking my pelvis trying to force him out. But that had the opposite effect. He just leaned into me and my bucking drew the huge tool inward, in to the sphincter muscle, which grabbed it and through his dick head right up against the prostrate. Sensing he was here, Clint rubbed his dick in and out ever so slightly, giving friction to my now-well-exercised prostate muscle.
"Found it again, didn't I?" he said with a big smile. I just groaned and turned my head. "God, I'm good," he said, "And you, Ben. You are one fine piece of ass." His dick well in now, he grabbed my other leg at the calf with his right hand and split me up and out as far as I would go. Then he walked another two inches into me. I shuddered, trying to make some sort of escape move, but not having any leverage.
"Please, please, Clint. You're splitting me apart."
"Gosh, I'm not even in as far as the dildo went, Ben. Although I guess I am a lot thicker." And he was, and I was feeling completely stuffed, and my colon was spasming again and he kept on coming.
"There, that's got to be the seven and a half. Oh, I love what your channel is doing. Oh, Gawd. There, Ben, You've done it. I'm up to the root."
Great I thought. Now it's about over. But, of course, it wasn't. He started to slowly pump me. At first all work with deep purchase, to get my canal to open to him as much as possible, and then longer strokes.
"There, we're all open and comfortable," he said cheerfully. Speak for yourself, I thought, but, indeed, he was all in and I was open to him, not feeling much pain and feeling at least a bit of pleasure.
"Next position," Clint said, as he pulled his dick out of me in one slide, pushed me up on the island counter and came up on the counter on his knees. Next position! What did that mean? He slid in under my thighs with his knees, sliding his dick head right up to my hole. Then, wrapping his hands around my sides, he pulled me toward him, his cock sliding into me as I was pulled toward him. I moaned. This was a tighter position. I threw my legs out as far as I could, opening as far as I could, but when he was in to the root, he gathered in my legs between his elbows. Closing my channel tightly around his pulsating cock. I thought he'd cum then and this would be over.
"Think I'm going to cum, don't you, Ben? Nope. I'm a master at that too." He held very still with his cock, fighting the need to shoot off. His hands went back to my hips and then ran over my belly and abs and down to my cock. I jerked my pelvis, trying to make him cum. He laughed and squeezed both of my butt cheeks with his hands.
"Nice try, Ben. But I do have marvelous control. Nice buns, by the way. Very, very nice." He held us there in that position for a moment, while the tension drained out of us both. When he was ready, he reached over and got a towel off the counter top and worked it under my back.
"Sweaty job isn't this, Ben. Here this will help you slide without catching." Slide?!
He wrapped his strong hands around my hips, and I watched the knotting and rolling of the arteries bulging on the muscles of his arms and pecs as he slid me back and forth, using me to pump myself. Again he stayed mostly buried deep so as not to lose purchase, but that left a good five inches of length he could use to pump me. He started slowly and then built and I was surprised that when he approached the point of no return this time he kept on going, his strokes getting closer together and his torso gyrating wildly. I watched in near fascination and a combination of pain and pleasure, as he threw his head back in triumph and screamed at the ceiling. I felt the cum ballooning up the head of his condom in waves of strong ejaculation. I had to admit that wasn't so bad. He just held himself there still for several minutes, his head thrown back.
"That was amazing," he cried, as he brought his head back up and looked down at me with great affection. "There, that was worth $300."
"$300" I responded indignantly. "You said $500."
"You've still got to work the other $200 off," he said with a grin. "I didn't say anything about how often I could cum for my money." he turned me on my left side then and strung himself along my body, and I thought he'd withdraw his cock which still was far up my ass even when tumescent. But he didn't. He stayed in me, folding my right leg up toward my body to help keep me open to him. He had his left arm under and wrapped around me, with his hand spread out on my belly. He buried his right hand in the hair and across the nipple of my left pecs and buried his face into the back of my neck and dozed. My panting and twitching slowly subsided until I slept.
The next thing I knew, Clint was biting my neck, had his left hand down and encasing the root of my cock, had my right leg lifted up in the air with his other hand, and somehow had his pelvis in motion and his dick moving in my ass canal.
"Arch your belly out and your ass back toward me," he commanded as I struggled for wakefulness and breath. I did as he commanded, and his re-hardened dick slid four inches farther up in me. How long had we slept, I wondered. He certainly reloaded fast for a man his age.
"This is called side splitting, in case you wondered," he said. "Useful information given for free here." Good name for it, I thought as I grunted through the new sensation. A few minutes of stroking like this, and then he surprised me again. Taking his left hand from under me, he reached up and somehow released my aching arms, and almost in the same movement, he released my right leg and pulled me up on his lap so that I was sitting in his lap, his dong about as far up me as it had ever been. We were sitting on the edge of the island, and both of us could reach the stool with our feet. He folded me tightly to him with one arm under my pecs and the other one just above my hips. He kissed and nuzzled the hollow of my neck.
"Got another of those $20 kisses for me?" He asked. I was too weary to demure. I turned my face to his and we went into a deep kiss. His hand went back to my cock and he stroked me, at first slowly and then he started beating me off with his hand. He broke from the kiss long enough to say, "I think we skipped this part earlier," and then he spent another $20 by reengaging in the kiss.
I squirmed on his lap under the insistent jacking of his hand, which made me bounce around on his embedded cock, giving me added pain and pleasure. I broke away from the kiss and begged him to slow down, which he did until we went into the kiss again and then he returned to the furious beating, beating, beating, until I had cum in three spasms of jizzim across his kitchen floor. He released me with his arms and I fell forward.
"Right idea," he said. "But arch your back toward me and rock back and forth. I did so, and felt the curve of his cock move the knob of his cock with that sack of spilled semen to the wall of my colon. I felt pleasure at that, but he felt more pleasure, and I could feel him twitching and moaning as I rocked back and forth. After a few minutes of this, he changed the command. "Lean forward, go up on your feet and grab your ankles."
I did as he commanded and his dick slid out of me. I had no illusion this was a signal of my freedom, however. I was now so open to him that he could do as he would and I'd feel no pain. He sensed this, because now he could move freely in me. He stood up on the stool behind me, grabbed my hips, slid right into, and pushed me back and forth, exiting wholly at each forward swing and then in up to the hilt with each swing back. He was huffing and puffing at this point. He stopped this motion after a while; let loose of one of my hips and, grabbing his cock rotated it around at several levels in me. Like the earlier movement, this brought his piss hole against the side of my channel and caused him to sigh and moan. After some of this, he sat back down on the edge of the island, extracted his dick and told me to turn around facing him.
I did, and he spent another $20 on a deep kiss. His hand went under my buttocks and, instructing me to wrap my legs around him; he leaned back and brought me into his lap, once again skewering my ass with his still very hard cock. Down, down I descended on his pole until I was sitting in his lap. He put his arms around me and drew me in. Then, with my hands on his chest, he moved his hands to my butt cheeks and rotated me around on his dick for a while. He was giving short pants again and had to stop for a few minutes, hold us both very still. The he told me to slowly arch my torso back. I did so, with him holding me at the side with his thumbs under my pecs.
Then he rocked me back and forth until he start to give short pants again. Again he held us in position until his urge to cum had passed. When he was in full control again, he told me to arch all the way back and grab for the floor as he stood. I did so and he stood on the stool, holding my hips firmly in his strong hands. I had my hand palms out flat on the floor, wondering what came next. My legs were still wrapped around his back.
"Legs on my shoulders," he commanded. One after the next, I swung my legs up on his shoulders so that I was supporting most of my weight on my hands, although he still had a grip on my hips. His head was in the air and mine was down toward the floor, my back was to his front, and his dong was plunged straight down in my ass, with the curve bringing his dick head up against my ass canal again. Slowly he brought his hand up until he had his hands under my knees. And then he split my legs out to the side again. All of my weight was on hands now.
"I know you are in great shape, he said, because I helped you get there. Now, for that last $100, do reverse pushups and, in the process, use my tool to fuck yourself. Do it until I cum and that will be the last of it. I figure, with a bonus that you will have earned $1,500. Now do it."
And I found that I could. I raised and lowered my body along his and stroked his cock with my ass canal until he shot off his wad once again inside me. With a shudder, he sat back down on the edge of the island, but in the process spun me around so that my back was to his front again, and we both just flopped back onto the countertop, me on top of him, my legs encasing his, his hands gripping mine and flinging our arms up and out, and his dong still up my ass, but receding into tumescence.
Then Clint slept. And when I could tell from his breathing that he was in deep sleep, I gingerly extracted myself from him and got off of the island. I was sore and felt like I was floating up to my eyeballs in sperm. But I had to admit that Clint was right about everything. This had been an incredible sexual experience, one that I had never come anywhere close to experiencing with a woman. I was glad I'd had this experience, even without the big bucks that came with it and in spite of Clint's bullying. I stood there and watch that beautiful, wiry body in repose. Clint turned onto his side in his sleep. He had said he wanted me to fuck him to, but he hadn't made that demand. I could show him that our relationship didn't have to be all about money.
I stood for a few minutes, thinking of that. I saw that there were still unopened condom packets on the counter, so I stroked myself down until I was hard again, and opened a packet and rolled a condom onto my dong. I reached over for the lubricant and took a dab into my hands. Then I came over to the island and climbed up on the stool. I ran my well-lubricated right hand up through his butt crack to his anus. I gently wrapped my left hand around his cock, which began to rise again under my gentle teasing and stroking. When I reached his asshole, I found that his opening was large. I gently lathered him up and inserted a finger in search of his prostate. He obviously thought he was having good sex in his dreams, because he sighed and moaned, but didn't awaken.
But he did slowly wake up as I found his prostate and he began to grunt with pleasure and produce precum, which I rubbed into his cock. He dreamily looked down at me, and cooperated and made no sign of protest as I turned him on his stomach and pulled him down toward me. His legs came over the edge and then his butt. I positioned myself on the stool, took my cock in my hand, and rubbed and slapped it gently on his butt cheeks and against his crack, making it get harder. I slid it into his butt crack and pushed it up and down, through the crack, which he must have enjoyed, because he sighed and moaned quietly. He reached back and pulled apart his butt cheeks with his hands.
"Do me, do me now," he whispered. "Put it all in me, straight up to the root. Now, now."
I positioned my dickhead at his hole and smoothly slid into him up to the root in one stroke. His channel was wide and he had no trouble taking me in. I plowed him for several minutes, and then reached over and took the dildo he had used on me. Pushing my dick to the bottom of his channel, I started working the dildo in on top of it. Clint took much interest in this, and produced much grunting and groaning as I double fucked him. When I had done and shot off my load, I rolled the condom back off my penis, cleaned myself up with a paper towel and water from the sink, and perched up on the edge of counter. Clint sat up then and, turning toward me, gave me another long, lingering kiss.
"And what had we agreed you'd be paid for fucking me?" he asked with a quizzical smile.
"Nothing that I know of," I replied. "That was a freebee. It was a symbol that it isn't all about money, and it's a gesture of appreciation for this evening and for making it possible for me to have my beach vacation."
"We can't have that," Clint said. "I wouldn't want to get a freebee. For that magnificent double screwing, I'll drive you to the beach myself. But we'll take three days to get there. Three afternoons driving and two evenings and mornings screwing in a nice hotel room. I think I still have some arguments to show you on why men can give you much better sex than women can."
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