Trip Money, Part 1

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 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 I must have been moping around about that during my Tuesday night workout, because Clint noticed that I was withdrawn.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 on the other side of me. 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 enjoy 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 nor 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, hadn’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 he 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," I responded, teased mightily by that hand covering my cock.

But at that point, he stood 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 take his breath in, and I found that this gave me a little thrill of pleasure, just as it did when the ladies got to the point of realizing what was going to slide into them.