Trip Money

I was reveling in a false ending, having been sucked dry by Clint. He 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 semen that they have to be milked by a doctor routinely. Massaging the prostate eases the pain from semen 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 semen. 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 part—a 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 same—and 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 your 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 semen 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 had 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 countertop 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 rehardened 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 watched as he exchanged the spent condom for a new one. 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 my ass 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 glans 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 my hands now.