Billy’s Special Payment Plan This is an explicit story about men having sex. You should not read it if you are under age or easily offended. To be honest about it, the special payment plan was my idea, not the Chevrolet dealer’s, Richard Jenson. Richard and I had been schoolmates, back in the day when I was a football star and he was a nerd. There were always rivalries between us. As early as eighth grade, he got control of a newspaper route that I had wanted, and needed much more than him. I made it through the Boy Scouts and became an Explorer, but Richard wasn’t even invited to join. In tenth grade we quarreled over a girl, who dated me for a few weeks, then dumped me for some other guy. She never gave Richard a second look. Once we got into a fight during a hayride sponsored by our church. In the aftermath, I was expelled from the youth group, while Richard continued on with it. To be fair, this was because Richard apologized for his part in the fight, while I refused to do so, caught up as I was in the role of an “angry young man” at the time. They all seem so silly now, these petty rivalries, but there was always some low-level tension that prevented us from becoming friends. By the time we reached age thirty, Richard had graduated college and inherited his Dad’s Chevrolet dealership, the only car dealer in our small farming town. I became a U.S. Marine, served in Iraq, and later returned home to work as a clerk in the town’s only hardware store. I lived in a one-bedroom bungalow at the edge of town, while Richard had one of the town’s biggest houses. Even though my military experience made me more disciplined and respectful of others, I still had a reputation in town as the local “bad boy.” I was a man of modest means, but I managed to save enough money to make a down payment on a new Chevrolet. I didn’t want to drive twenty-eight miles to the next town, so I bought my Chevy from Richard. Richard was married, mostly unhappily, while I was an unattached playboy, a poor one, not exactly the town’s most eligible bachelor. But I had more than my share of girlfriends, not all of them single. One of them was Richard’s wife, but I don’t think he ever knew this. To shorten a long story, during the Bush Recession I got laid off from my job at the hardware store, and could no longer make my car payments. What’s a poor man to do? Richard ran his own finance company as part of the car dealership, so I went to his showroom to talk about car payments. Knowing that Richard was living in a tense relationship with his wife, I proposed a bargain: my sexual services in exchange for car payments. I had heard a rumor that Richard was planning to divorce his wife, and I figured that it would be to his benefit if he could prove that his wife had a boyfriend. It was a pretty “low down” idea, I admit, but I was desperate. Richard improved on the plan. For any given month when I couldn’t make my payment, I was to report to his cabin on the lake each Monday afternoon, and there perform any sexual service that
I might be required to render. That was the way Richard worded the deal. Of course I assumed that the person I would meet was his wife. I was already two months behind on my payments, plus interest, so to prove that he was sincere, Richard made the payments for me free and clear. No services required for the months during which I was “in arrears,” as he said. This was an offer that I couldn’t refuse. In fact, I couldn’t believe my good luck, and I told him so. We shook hands on the deal, and spent the evening at the town’s sports bar, eating steak and drinking beer at Richard’s expense, and reminiscing about high school days, my time in the Marines, and his in the car dealership. By the end of the evening, it felt as if we had always been friends. When we parted company, me in my new Chevy, Richard reminded me, “Remember, Billy, 3:00 PM sharp at my cabin!” Everyone knew where Richard’s cabin was. He was famous in the neighborhood as a scoundrel. He didn’t like people fishing in the lake near his cabin, so once he bought some old-fashioned bedsprings and planted them in the water by his lakefront. That was so fishermen would snag the bedsprings and lose their fishing lines. It worked. Most boaters avoided fishing anywhere near his cabin. That was Richard being Richard. I showed up on time at Richard’s cabin. Naturally I thought that I would meet his wife there. That was our plan, or so I thought. Imagine my surprise when the person waiting for me in the cabin was Richard! It was an awkward moment for me, but Richard seemed comfortable with it. He greeted me warmly, shook my hand, and offered me a brandy. “Brandy,” he said, “an afternoon delight for an afternoon delight.” He laughed. “Richard, about our bargain for sex....” I stammered. “Please call me Dick, my dear Billy. Please call me Dick. After all, that’s what you’re here for!” I was stunned. “Unless you want to cancel our bargain and resume your car payments, or else return that nice new red Chevrolet that I see in the parking lot. In that case, I’ll give you a ride home and we’ll call it a day.” “You know I can’t give up my car,” I said. “You’ve got me over a barrel, Richard. But if you want me to service you, well....” “Oh no, no, no, Billy! Nothing like that,” he said. “It’s me who is going to service you,” he laughed. “You service me! But I’m not gay,” I exclaimed. “And I’ve never done anything like this before.”
“Of course you’re not gay,” Richard replied. “If I thought you were gay, I never would have struck up our bargain. But I’ll tell you what. You don’t have to decide this minute. Let’s have a few drinks, and watch a few inspirational DVDs, and then you can either stay or leave, no hard feelings. Of course, I’ll have to repossess your car.” So I agreed to stay. We watched a hetero movie, and shared comments on both the women and the men performing in it. We both got a little high. My comments were mostly about the women, and his were about the men, but we both got horny, and I started joining in with comments about the men, as well. When the first DVD was over, Richard asked if it would be okay for us to watch a gay flick. So we did. At first I watched in stunned silence, shocked at the spectacle of men kissing men, fondling each other, sucking cock, and fucking. Eventually I got more comfortable with the DVD, or maybe I was just drunk. I started exchanging comments with him about the men in the DVD. We started to play a game, guessing which guy in a scene would get fucked, and which one would do the fucking. Richard suggested that we improve on this game by playing it like strip poker. “Whichever of us picks the wrong outcome in a scene must take of an article of clothing,” he said. “You have me at a disadvantage,” I said. “You’ve seen the DVDs before. I haven’t. How do I know that you don’t know the outcome already?” “Not with these, Billy,” he said. He handed me a stack of DVDs still wrapped in cellophane. “These are new DVDs. You pick one.” I unwrapped one of the DVDs. But Richard was better at this game. An hour and a half later, I was butt naked, while Richard still had his pants, shorts, and one sock. Richard was delighted with my predicament, sitting naked with him on the sofa watching gay DVDs. At first I felt embarrassed, but I started to get horny when Richard made a show of ogling my body, with special attention to my midsection. I didn’t mind being eye-candy for Richard. In fact, I enjoyed it. I was physically fit and well endowed, and had nothing to be ashamed of. I have to admit that Richard had kept his fitness. “You’ve run out of clothes, Billy, but you can still pay up for your losses,” Richard said. “How’s that?” I asked. “With a little game of grab-ass. Each time you pick the wrong outcome, I get to make a move on your ass.” I agreed to this modification in the rules of the game. Half an hour later, Richard still had his underwear, while I was sporting a hard-on. Following the rules of our grab-ass game, he had been groping my cock, my balls, and my ass. I got used to his intimate touch, and, I admit, I got
horny enough to grope his hard dick beneath his shorts while he was groping me. He didn’t seem to regard this as an infraction of the rules of grab-ass. I couldn’t help but be impressed by his package. I had no idea that Richard was so well hung. I guessed that he hard-on was eight inches at least, maybe more. At last the time came when Richard had to step out of his shorts. His cock flipped forward, jutting out a good nine inches. The biggest surprise was his ragged foreskin. I had never seen an uncut cock before, not close up, anyway. After all, I was straight, and even in the Marines, I never looked closely at other guys in the shows. He could see from my gaze that I was impressed at this tower of manhood. We sat side by side and continued the game. We took turns winning the privilege of groping each other in intimate parts of our male anatomies. Mostly I groped Richard’s throbbing cock, but Richard was partial to groping my ass. The symbolism of this was not lost on me, for I knew that I had already bargained my body to Richard and my ass was the prize. His prize. Our fourth DVD came to an end. I hoped Richard would start a fifth one. Instead, he put an arm around me and drew me next to him. I responded by fondling his naked cock. Never before had I touched another guy’s cock, but it seemed like the right thing to do in my situation. We both knew that this cock was to be my introduction to gay sex, so I figured I might as well get the feel of it. His cockhead was wet with pre-cum. I moistened my finger with it, and massaged his pre- cum into the sensitive bundle of skin just below his cockhead. His cock throbbed under my touch. It was an erotic moment, and exciting, for me as well as for Richard. He was a scheming scoundrel, but sexy. I was a not altogether innocent victim of his tricky bargain, but at this moment, I felt only admiration for his success in tricking me out of my virginity. This is the cock that is going to bust my cherry, I thought to myself. My anxiety about this seemed to fuel my growing desire to let it happen. Yes, I was a stud who was about to submit to another stud. I wanted it as much as I feared it. Richard leaned over to kiss me. I let his lips touch mine. So here I was, a straight guy, sitting in the nude with my naked seducer, passionately kissing him. I had never kissed a man before. “You know, I’ve always liked you, Billy,” he said, tenderly. “I guess this means you’ve decided to follow through on our bargain.” He was very diplomatic, even though we both knew that he had won the right to pop my cherry. “A deal is a deal,” I said. Still embracing me, Richard put his free hand between my legs and fondled my balls. Then he reached further down and fingered my perineum. I arched backward and parted my legs. Richard moaned approvingly, and pushing ahead, he pressed two fingers against my asshole. I didn’t try to stop him. “I’ve always wanted to get into your ass, Billy,” Richard said.
“A deal is a deal,” I repeated. “Maybe you’ll find out you like it, if it’s done lovingly, and carefully,” Richard said. “Well, I’m sure gonna try,” I said. “Good man!” Richard exclaimed. “Good man!” I felt a fingertip enter my asshole. He wiggled it around the edges of my anus, playfully. “Do you like how that feels?” he asked. Before I could answer, Richard said, “Yes, I know. A deal is a deal.” “I was going to say, well,” I said, almost choking on my words. “I was going to say that yes, I like it fine. It’s all so strange to me, but yes, I can do this.” I kissed his lips. Richard was surprised and pleased at this sign of affection from me. “Thank you for that, Billy,” he said. “It will go much easier for you if you’re a willing partner. Shall we go to the bedroom and get busy?” “Yes,” I agreed. “Let’s do that.” Richard took my hand and led me to the bedroom. He had a queen-sized bed, with plenty of room for fooling around. “We’ll keep the light on, Billy,” he said. “There’s nothing more beautiful in the world than the face of a man who is about to lose his cherry.” “Good idea,” I said. “I’d like to see what I’m getting, too. I’m really nervous about this, Richard.” “You’ll be fine, Billy. Just let nature take its course. With a little force from me,” he chuckled. I’ve got everything we need here.” He pointed to the nightstand by the bed. “Lube for your ass. A vibrator to get you started. A bottle of poppers. And some little blue pills to keep us going: Viagra. Let’s take the pills now.” He still had his glass of brandy, so we used it to wash the Viagra down. “Oh, and there’s this, a special pillow that I got you for the occasion. It was a heart-shaped pillow, pink on one side and red on the other. At the center of the pink side was a golden Cupid with a bow and arrow. At the center of the red side was the image of a man holding a rose that he had plucked. “We’ll use the pink side the first time I fuck you,” he said. “And the red side for the second time, and third, and fourth, and fifth.” “You’re so romantic, Richard,” I said. “But I’m not familiar with poppers.” “Oh, don’t worry about that. I’ll show you what they’re for when the time comes,” Richard said. “What about condoms?” I asked. “What about them?” Richard replied. “I figured we’d be using condoms,” I said.
“I want to ride you bareback, Billy,” he said. “I want the feel of my naked cock sliding into your virgin manhole. And I want you to enjoy the feel of my naked cock.” He placed my hand around his throbbing cock. “I wouldn’t want to deprive you of the feel of this up your manhole. Up and into your garden of delight. And anyway, a cherry isn’t completely popped until it’s creamed.” What was the sensual attraction of this trickster that made me agree to let him ride me bareback? He seemed pleased, but not surprised, when I said yes. “I promise you won’t be sorry,” Richard said. “You’ll always remember our time together here. You’ll be glad that we did it the right way, riding bareback.” I kissed Richard, and he kissed me back. “Besides, I’m going to breed you,” Richard said. He had me where he wanted me. I kissed him, and he knew that by this kiss I was willing to let him breed me. “Bareback and breeding, how I love those words,” he said, and returned my kiss. “You’re the boss, Dick,” I said. “You’re the boss.” “Now that we’ve got that settled, Billy, just lay down on your belly, so I can get a better look at your ass. I want to inspect my prize. You’ve got the most beautiful ass I’ve ever seen. And you’re so well hung, too. You’re quite a stud, Billy. Quite a stud.” “A stud whose about to become a mare in your stable,” I said. “You said it, Billy. You’ll still be a stud, but when you’re with me, you’ll be a mare.” He administered a couple loud swats to my thigh. I lay on my belly, and Richard started fondling my butt and running his fingers up and down my crevice. “Thanks for the compliment,” I said, “but you’re a pretty powerful specimen of manhood, too, and you’ve got the biggest dick I’ve ever seen. Not that I’ve ever seen another guy’s erection before. Yours is the first, for me.” “I’m glad you like what I have to offer you, Billy,” he said. He knelt at my side and stoked my butt. Fondled it. “Such a beautiful ass.” I looked toward Richard, and found that he had positioned himself so that his cock jutted inches away from my face. I leaned toward his cock, and he edged closer to me. My lips touched his glistening cockhead. By now his foreskin had retracted, or rather, his prick had expanded, and his cockhead had freed itself from its hood. I licked a bead of pre-cum from his wide piss-hole. I liked the way it tasted, and licked it again. I don’t know whether he pushed his cockhead into my mouth, or I sucked it in. Either way, I had my first mouthful of cock.
Richard lay on his back and let me explore his cock with my mouth. He moaned with pleasure when I played with his foreskin, sliding it up and down the cock-shaft. “I’ve always been jealous of guys with foreskins,” is said. “Having an uncut cock was always a fantasy.” “Well, now you have mine, Billy,” he said. “My cock is yours, and your ass is mine. A fair exchange, I would say.” Richard lay over me in a 69-position, and we played with each other’s genitals, fondling each other and sucking in cock and balls. His balls were hefty, but I found that I could suck in one testicle at a time. Richard did the same to me. We exchanged positions, and continued to pleasure each other. Richard started paying more attention to my ass. I knew that the time for my deflowering was near. But before we got to that, Richard had something else in mind. He sat on the edge of the bed, and told me to kneel between his legs. Then he reached for the poppers. He lay on his back, propped his legs on my shoulders, and told me to kiss him behind his scrotum. When I did this, I got a close-up view of his asshole. I always thought that something like that would be disgusting, but it wasn’t. “Now, Billy, it’s time to break out the poppers,” Richard said. He showed me how to use them by taking a couple of long, slow snorts from the bottle. “Now, Billy, I want you to take a couple good snorts and kiss me behind my balls again, just like you did before.” I snorted the poppers. I felt the intoxicating effect of them as soon as my lips touched his perineum. High on poppers, I kissed Richard’s asshole and licked it with my tongue. Richard moaned in guttural pleasure and said, “That’s the way, Billy boy, kiss my asshole. Ram that sweet tongue up my asshole.” I kept on licking his ass, even after the effect of the popper wore off. Richard didn’t have to tell me what to do next. I took another snort of the poppers, and rimmed Richard’s asshole again. This time I tried to ram my tongue up his hole. “Yeah, fuck my hole with your tongue,” Richard said lustily, commanding me to do what I was already doing. The whole scene was strange and erotic. I found that I enjoyed giving pleasure to Richard. My third snort of poppers, and I felt a compulsion to rim Richard’s ass even harder. I used my fingers to pry his ass-cheeks apart and expose his asshole more completely. I tried running my tongue up and down his hairy crevice, but I found that I couldn’t reach very far in the position he was in. Richard moved into a new position, doggy-style on the bed. I knelt behind him, with my face near his ass. I snorted poppers again, and ran my tongue up and down his crevice. At the end of each run, I tried to penetrate his asshole with my tongue. He moaned, and kept repeating, “Yeah, kiss my ass, run that tongue up my asshole. Fuck me good with your tongue.”
After the poppers wore off, Richard started to shift his weight, but I told him, “Not yet, Dick, I want to kiss your ass one more time.” He grunted his approval. I snorted the poppers and said, “One more time with my tongue up your ass, then you can pop my cherry.” “You’re wonderful, Billy. You’re really a natural-born rimmer,” he said. By that time my tongue was in his crevice, and in his asshole, but I managed a reply: “I’m really liking this,” I said. I was cherry-picking time. Richard gathered me in his arms. “I’m going to pop your cherry now,” he said. “Pluck the rose of your virginity. But not until you’re ready. We should talk about it first, to let you know what you’re in for. I’ll know when you’re ready when you snort some poppers and give me the kiss of the bride.” “The kiss of the bride?” “Yes, a passionate kiss that tells me when you are ready to take me as your man. You’ll know when your time comes. Then I’ll return it with the kiss of the man, your man. Then you will mount the pink pillow, and I’ll mount you. It makes our scene more romantic, a bridal bed, not a butcher shop,” Richard said. “You must have some questions, Billy.” “I suppose this is gonna hurt,” I said. I fondled Richard’s cock. “Yeah, it’s gonna hurt. A lot. When I first penetrate you, the pain won’t be so bad, more like a dull thud inside you. First I’ll push my cockhead into your asshole. That’s when you’ll feel the dull pain. After that, I’ll push my shaft half-way into you. That’s when you’ll feel a pain the likes of which you’ve never felt before, not even when you were a Marine. You’ll beg me to stop, or pull out, but I won’t. I won’t give up any conquered ground. But I’ll wait until you’re ready before I give you the third big push, my cock all the way up your ass. Here’s the real kicker. That really sharp pain will come back, even worse, but we’ll both keep very still until the pain goes away. And it will, I promise. I won’t start fucking you until you’re ready.” I responded by sucking Richard’s cock, and kissing it. “This cock will be mine in the end.” “Make that up the end,” Richard laughed. “Up the end. He’s so big. I think we should call him Moby Dick.” “Keep in mind that once Moby Dick is inside you, were on a road of no return. He won’t pull out until you’ve been thoroughly deflowered. I’m sorry about all the bad news about pain, but remember, in order to transform your ass into a pussy, a lot of things have got to stretch inside you. Especially your sphincters. The inner sphincter, especially.” “Richard, I have to tell you that something happened to me while I was rimming you. I felt an urge to surrender. I felt a desire to give my body to you. And I still feel it.”
“Then your struggle is already half-way over,” Richard said. “Surrender will come whether you want it or not, and it’s better to want it.” “I don’t want you to feel sorry about the pain, though, Richard. I want you to feel pleasure, not regret.” “You’re right about that,” Richard said. “The whole time that you’re squirming in pain, I’ll be feeling pure pleasure.” “Knowing that will help me endure the pain,” I said. “And what happens when the pain goes away?” “Quite a lot,” Richard said. “You’ll feel a strange sense of fullness, and pleasure will come, too. My guess is that you’ve got some sweet spots in your anal canal, and they will be activated when we start to fuck. Not to mention your prostate, which always likes a good massage. When it comes, the pleasure will consist of feelings that you never had before. If we take everything slowly and carefully, you’ll want to come back for more. You might even get some anal orgasms, though not all guys do.” “Anal orgasms?” “You’ll know what they are when you get them, if you do,” Richard said. “I think it’s time for me to snort the poppers now,” I said. I did, and I kissed Richard passionately, the kiss of the bride. Richard returned my kiss, and guided me into position with my ass on the pink side of the pillow. He knelt between my legs, and lubed my asshole with his fingers. He reached for the vibrator. “We’ll start with the vibrator. It will make my initial penetration easier to take.” He pushed the vibrator in slowly, and fucked me with it gently. “When I turn the vibrator on, concentrate on what you’re feeling in your ass.” The vibrator was pure pleasure. He turned it on and held it still at first. Then he fucked me with it, slowly. I wanted to stoke my cock, but he brushed my hands away. “Don’t make yourself cum prematurely,” he said. He kept on with the vibrator until I begged for him to fuck me. Then he removed it and got into position, into the cockpit. I groaned briefly when his cockhead went in. Then he pushed his shaft half-way in, and my pain was enormous. For several minutes it was a sharp burning pain. I groaned, and cried out, but I didn’t beg him to withdraw. “Please don’t stop, please don’t stop,” I said. “Concentrate on your breathing,” Richard said. “Take deep breaths.” This was good advice. Richard kept his body still, and we gazed in each other’s eyes for what must have been ten minutes, but to me the event as a whole was timeless.
“I’m ready now, Richard,” I said. Richard pushed his cock all the way in, in one slow, resolute action. Again I cried out from the sharp burning pain. “I’m all the way in,” Richard said. “The worst is over.” We lay together quietly for another ten minutes. Twenty minutes inside me and he hasn’t even fucked me yet, I thought. Then I said it. Richard took the comment as his green light. He started fucking my ass in slow, gentle movements. The movement of his cock inside me seemed strange at first, but I got used to it. Still, I felt an overwhelming sense of fullness, as if Richard’s whole body was inside me. I liked the feeling. Richard’s cock started getting more active. His strokes became longer, and harder. Every once in a while I felt a sharp pain, not a burning pain, but more like the feeling that his cockhead had found a spot that was previously untouched. Eventually Richard started to alternate between sessions of hard, vigorous fucking, and a slow, gentle massage of my anal canal. The vigorous fucking was exciting, but his anal massages gave the most pleasure. Richard watched my face and gloried in the pleasure that he was giving me. Then something else happened. During those anal massages, I started to feel a Pop! Pop! Pop! Popping in my anal canal. The best sensation yet. “I think I’m getting some of those anal orgasm you were talking about,” I told Richard. “I was hoping you would,” Richard said. “It’s the hard humping that stimulates them, and it’s during the slow, gentle massage that you feel them. “In that case, fuck me harder,” I said, and he did. We experimented with different positions. Richard fucked me from behind, doggie-style, and with me flat on my belly. I sat on his cock, facing him and with my back toward him. He stood up and fucked me with my ass on the edge of the bed, propped up on the pillow. We still used the pink side. He fucked me from behind standing up. “This is good practice for in the shower,” he said. Then we got back into the missionary position, face to face. We liked this position best because it seemed more intimate. Richard’s penetration was easy to take this time. We were in for the finish. He fucked me slowly. “Billy,” he said, “I’m gonna breed you now.” “Yeah, kiss me first, then breed me,” I said. And he did. We lay together quietly, while Richard soaked his cock in my anal canal. I could feel its slickness, and it tickled a little. When he withdrew his cock, it was still half-hard. He fondled my throbbing cock. Suddenly he was hard again. He turned me over on my belly, and fucked me from behind, hard and furious, until he came a second time.
“That was what you’d call a double,” Richard said, panting, while he lay over my back with his wet cock still up my ass. “A double breeding. Maybe you’ll have twins.” My cock was aching for release. Richard wanted me to jack off while I talked dirty to him. I lay on my back, and he knelt between my legs. I stroked myself while he watched. I told him anything I could think of about how I felt, how I didn’t want to lose my cherry but now was glad that I did, how I was glad that it was him who fucked me, how I liked his big cock, how I wanted to rim him again, how he gave me anal orgasm, how my ass could still feel the physical memory of his cock, how I could feel his cum inside me. How I used to be straight until he turned me into his bottom. “You’re not the master of my virginity,” I said. Then my cock erupted for him. We spent the night together. Richard fucked me two more times during the night. In the morning, we gave each other blow-jobs in a sixty-nine position, so I tasted my first load of cum, and got my first blow job. So Richard became my new best friend. We continued to meet every Monday afternoon. He still makes my car payments, even though I said I was willing to let him fuck me for free. I stopped dating women and started looking for guys. Richard introduced me to a couple guys who I saw off and on. He suggested that I should go into business as a hustler, since there would be a great demand for a stud like me who likes getting fucked. But I got my job back as a clerk in the hardware store, and that’s there I’ll stay. The end.