Date: Wed, 24 Jun 2020 21:37:45 -0700 From: Jason Ford Subject: The Deal, Ch. 14 The Deal By James Forbes Chapter 14 – The Challenges This is a 19-chapter series of (partly) fiction created for the entertainment of interested adults, partly based on my experiences as a youth. Please read no further if you are underage, if this is illegal in your area, or if you are offended by explicit sexual stories. Names and locations have been changed. This would have taken place in the pre-AIDS era. The main focus is on physical and psychological domination, submission, various punishments and kink. If you enjoy this kind of story, please show your appreciation by making a donation to Nifty Archives. Go to: http://donate.nifty.org/donate.html. And if you need a good sub in the San Diego area, or have comments on the story, contact me at jasbike1@gmail.com. I barely slept the night after Scott took me to the grocery store, as I knew I had to meet him in the woods the next morning. Under different circumstances, I would have had the hots for Scott. Brown hair, green eyes, short, slim, and strong, with tight balls, a healthy 6.5" dick, and compact boy bush. But he was in control of me, body and mind. My obsession wasn't so much desire as it was fear and trepidation, knowing something was going to happen but never knowing when or what. When I got to the clearing in the woods, Scott wasn't there, but there was a note: "Use the rope to tie your hands together in front of you. Tie the bandanna around your eyes, spread your legs, and wait." I had never tied myself up before, but I had seen Scott do it. I made it snug in case he checked; if he found it too loose, I knew I'd face the consequences for sure. It seemed like forever, standing there in the woods waiting, but I finally heard his footsteps crunching along the long trail to the clearing. My heart raced, and my dick started to get hard. I could hear him walk slowly around me, as if examining a prized specimen. I panicked at what I heard next, though. It started only as whispers I couldn't decipher, and I thought Scott was whispering something to me. I whispered back, "What?" More whispers, louder this time, but in different voices. He wasn't alone. A deeper voice: "Really? Holy shit." Another voice, not Scott: "Are you serious? I don't believe you." Scott: "I'll prove it. You'll see. Let's put money on it." Then Scott spoke up. "Prisoner: Take off your blindfold." I reached up with my bound hands and slipped the bandanna down around my neck. My knees nearly buckled. Scott's older brother, Danny, and their friend and neighbor, Andrew, were there. I'd had experiences with both of them, separately, but as far as I knew until that moment, none of the three boys knew about each other. Danny was my first when he was 12 and I was 13. Now he was nearly 16, and I was closing in on 17. Andrew, 15 now like Scott, and I had showered together and traded BJs, then one day he took me to the woods, and while I blew him, he pissed in my mouth, running off laughing. How much had Scott told them? I was mortified. I meekly tried to protest. "Guys, this is all just a bad joke. Scott dared me to do this, but I thought it would just be him. So just untie my hands and we'll have a big laugh about it, OK?" "Prisoner!" Scott barked at me. "Since you can't control that mouth, I'll control it for you. And you'll face additional punishments for your outburst." He grinned at the other boys, then undid the bandana around my neck and shoved it in my mouth. "Guys, I present to you the new James. He used to be older than us, taller, and bigger in, uh, other ways, but as you'll see, all that has changed. He voluntarily went to Dr. Tanner, the school's athletic doctor..." At the mere mention of the doctor, I knew Scott was going to tell the other boys everything. Suddenly I felt warmth between my legs and realized I was pissing myself. "Oh my god, look!" Danny said. The ginger-blond pointed at my crotch, which was now soaked, a dark patch slowly growing through my jeans and down my leg. "He peed himself, just like a baby! What the hell did that doctor do that scared him so bad? Maybe baby deserves a spanking." Scott readily agreed, walked over, the unbuttoned my 501s, pulling them down just enough to reveal my jockstrap. "How about 20 spanks from each of us?" he suggested. The three of them turned me around and started swatting my ass, hard. Andrew, the blond, seemed to take the most pleasure in it. My ass was quickly pink, then a dark red. "I can see my handprints!" Danny said. "I can't believe he just lets you do this." Scott told them, "It's not like he has much choice. He knows if he complains, it will only get worse." Sixty spanks later, my ass was so sore I could barely stand. Scott told the boys, "I think it's easier to show you what the doctor did rather than to tell you. First of all, do you think James has any armpit hair?" "What do you mean?" his brother asked. "Of course he does. I mean, I'm 16, and you guys are almost 15, and we all have pit hair. Everyone does at our age." "Fine," Scott said, "Let's all put a dollar up and see." They all dug into their pockets and pulled out crumpled dollar bills, placing them on a tree stump. Scott tied a rope around my bound hands, and threw the line over a tree branch, then slowly pulled my arms up, revealing my smooth pits. "Wow, Scott," Andrew said. "You made him shave his pits." Scott corrected him. "Nope. The doctor applied some sort of medical potion, a lotion, and fairly quickly all his pit hair was gone. Like forever. He doesn't really look 17 anymore, does he? And I guess this money is mine. Let's get his tank top off." Scott ripped the tank top in half, and it fell to the forest floor. "So he doesn't feel lonely, let's all take our shirts off." The boys readily agreed. "What do you guys think about James' legs? Hairy, or not? All high school guys have hairy legs, right?" Andrew thought about it. "Well, yeah, but mine are super hairy, Danny's like medium hair, and you, Scott, only have calf hair, so it varies. But even `young' James must have some hair on his legs, sure." Danny agreed, too. "Well, let's see. Money on the tree stump!" Scott said. They ponied up more cash. Scott took off my boots and socks, then grabbed my piss-soaked jeans at my ankles, and whipped them off in one yank, revealing hairless legs. "Shit!" Scott brother Danny said. "Now he barely looks like he's in junior high. Not 17, that's for sure. More like 14? 13?" Scott told them, "You'll see. It took five visits to the doctor to finish everything." I only had my jockstrap left. I dreaded what would come next. "Guys, let's take our shoes, socks, and pants off for poor lonely James." The boys did, revealing Scott in tighty whities, his brother Danny in sheer boxers, and Andrew in tiny European briefs that showed his huge cock, clearly hard. "Now I think this final piece of clothing needs a higher bet. If you're right about him having dick hair, I'll suck James' dick, right in front of you guys. If you're wrong, you guys have to suck him." Danny was the first to react. "I'm not doing that. This is unfair. I know for a fact he has to have a little bit of dick hair, no matter what." Andrew chimed in. "Gross! There's no way! But I still say he has hair down there. I've had mine since I was 12." I started writhing around, trying to free myself from the ropes tying my arms up to the branch, and yelling into the bandana gag. "Calm down, Prisoner, or you'll be wishing for a bandana gag." What did that mean? Scott got behind me, and in full view of Danny and Andrew, ever so slowly pulled down the jockstrap to the base of my dick. "As you can see, guys, not a hair to be seen. And—" he continued to slide the jockstrap down, until my dick popped out and my smooth balls were revealed. "—no hair here, either. Nothing below his eyes, actually. The doctor made sure of that." All three boys walked around me. "Wow, that's amazing. Poor little James," Andrew said with a sarcastic tone. "Not even 14 or 13. I'd say 12. And with a red ass, too, heh-heh." Danny was shocked. "I've never seen anything like it. Even the boys in 7th grade gym class had some hair somewhere, like arms or a little on their dick. Something. How embarrassing. His dick is pretty small, too." "You're right! I forgot to mention," Scott told them. "A side effect of the treatments was James' dick and balls shrank. His dick—penis, I think we should call it from now on—is only 2.8 inches soft, and 3.8 inches hard, less than half of what it was a month ago. Notice anything else?" Scott grabbed my dick and balls, and twisted them hard. My gag came flying out of my mouth. "Scott, please, stop! They've seen enough. They know everything, OK? Just let me go!" I pleaded. "Prisoner. I warned you. Now it gets worse." Scott grabbed my piss-soaked jockstrap, wadded it up, and jammed it into my mouth. "Ewwww!" Danny said. "That's the jock he peed into a few minutes ago." Thankfully, Andrew didn't tell the boys about him pissing into my mouth a year before. Danny continued, "Um, his dick—penis, sorry—doesn't have any foreskin." Danny knew full well I used to have foreskin, from our first encounters some four years previously. Scott replied, "Bingo. You get the prize. Which is, you don't have to suck James off after all, and you get to be the keeper of this." He pulled out a pill bottle from his pocket filled with fluid. Something was floating in it." Danny took it from his brother. "What is this?" Danny asked. "It looks like. Oh my god. It is. That's his foreskin. The doctor did this?" Scott nodded. "He deserved it," Scott confirmed. "He was very uncooperative at the doctor." Scott continued. "You guys up for a demonstration? We went to the grocery store yesterday, and I want to test James to see if he's up to the challenge. After each test, one of us will get to fuck him. First up—" Scott pulled a banana from his grocery bag, and began to squirt hand lotion on it. "Are you going to do what I think with that?" Andrew asked. Scott grinned. "Well, sort of. James is going to use it on himself." He untied my aching hands from the branch above me, freed both hands, then used the two ropes to tie my legs apart to small trees on either side of me. "Prisoner: Bend over and shove that banana up your ass." In full view of the three boys, I bent over and began to try to work the banana inside me. It was half in when my hand slipped, and it fell completely out. "A failed challenge," Scott said. "Here—I'll put it back in. I could feel it slowly working itself inside me, hitting my prostate. He slid it in and out for several minutes, then pulled it out. "For your failure, you have to eat it. Danny is going to fuck you now, but he'll stop as soon as you finish the whole banana." Danny walked around, lowered his boxers to his knees, and I could see his dense, tight bush, several shades of red darker than his strawberry blond hair. His cock was nearly as long as mine used to be, about 6.5", with large, round balls that had white-blond hair on them. He slowly slid his cock into my ass, and I groaned into the piss gag. Scott took out the gag, then started pushing the peeled banana into my mouth. It tasted bad, like tangy vanilla. I'd eaten about half of it, with Danny thrusting harder into my hole, when Scott told me what he'd done. "When I was behind you, I peeled the banana before shoving it in your little boy hole. So you're kind of eating your own ass right now." I nearly threw up, and started choking, but Scott kept pushing the banana into my mouth until I'd swallowed the whole thing. Just then, Danny grunted and I could feel his load go up inside my bowels. "Next up," Scott said, as if this was all routine, "This zucchini. Andrew, you can use it on him. After squirting the lotion on it, Andrew lowered his European briefs, and I was amazed by how much his cock had grown since the last time I'd seen him naked. It was at least 8 inches now, thick, with a spreading black bush that contrasted to his blond hair. While Danny had gone easy with the banana, Andrew didn't waste any time. After slapping my ass a few times with the zucchini, he shoved it inside me. I yelled, so Scott put the piss-soaked jock back in my mouth. "Remember what happens if it falls out," Scott warned. I tried to grip it with my ass as Andrew pushed and pulled it really fast into my hole. "I can't believe this thing is going all the way in his ass!" Andrew said. "In, and out, in, and out, and—oopsy!" On purpose, Andrew let go of the zucchini, and all nine inches of it came dropping out of my hole. Without being prompted, Andrew jammed his fat cock into me, all the way in. I could feel his black bush banging up against my red ass cheeks. As Andrew fucked me, Scott picked up the zucchini, took out my gag, and pushed as much of it as he could into my mouth. "Grab it with your teeth," he ordered. I managed to hold it about halfway into my mouth. The taste was revolting. Andrew didn't last long, pulled out, and jacked his tool, spewing cum all over my ass, which stung like acid. I tried to yell, and the zucchini fell out of my mouth. "Prisoner," Scott said, "Just for that there is one more challenge. Guys, help me lift him up over that stump." They untied my legs. Then Scott threw a rope over a branch, anchoring it at one end. "Stand on the stump, Prisoner." Wobbly by this point, I climbed up on the stump. I could feel cum dribbling out of my ass from the first fucking delivered by Danny. "Grab the rope," Scott ordered. I did, thinking it was just to brace me so I didn't fall off the stump. "Here's what's going to happen. You'll pull yourself up the rope a foot or so." I did as instructed. "Guys, grab his legs and hold them out straight." I was then "sitting" in an L position, but hanging from the rope. Then Scott brought out the huge butternut squash from the grocery sack, and lubed it up, placing it on the stump, about two feet below my ass. Danny was in disbelief. "No fucking way. That can't possibly go in his ass. That cucumber thing barely fit." Andrew, too, was doubtful. "Yeah, when I was just fucking him, my cock was tight in that asshole. That thing is twice as thick as my cock." My bent arms were already getting sore. "Normally I'd agree, guys," Scott said. "But with a little incentive, and gravity, he can't last forever." Scott brought out the bag of clothespins he'd taken from my mom's clothesline. "One here, another there," he said, pinching one on each of my nipples. My arms relaxed a little, and I was only inches from the gourd invading my ass. "One on each ball should help him along," Scott continued. The pain was nearly intolerable. "And finally," Scott said, and started rubbing clothespins on either side of my boy penis, which was still recovering from circumcision. "Scott, he can't take that. Holy shit, that's gonna hurt so bad," Andrew said. "He'll take as many on that small, hairless dick as I can put on until that squash is inside him." Scott started on either side of my dick, at the base. Two, four, six. The pain was excruciating. My arms slipped, and I felt the head of the squash pushed up against my hole. Danny looked underneath me. "Jesus! It's starting to widen his hole. I don't believe it." Danny said. "Two more ought to do it," Scott said, and put two on either side of my dickhead, just above the circumcision scar. I couldn't take any more, and my hands slipped a few inches down the rope. The squash was now firmly in my ass. Scott told me. "Here's the deal. You remember our deals. The more of that you take, the more clothespins I'll take off." He took two off the base, which hurt even more than when he'd put them on. A couple more inches of the gourd spread my ass wide. By this point I wasn't really holding myself up on the rope. It was more Andrew and Danny holding my legs that kept the whole gourd from wrecking my ass. Just as Scott removed the final two clothespins, I could feel I was at the base of the gourd, with the wider half acting as a perverse seat of some kind. Danny and Andrew let go of my legs, and the three boys walked around me, marveling at how much was lodged in my ass. Scott jumped up on the stump. "We should just leave him like this, but first..." He took out my gag, lowered his tighty-whities, and started mouth fucking me. He pulled out almost immediately, and shot a large wad into my open mouth, while Andrew and Danny laughed. Scott put my pissy jock back into my mouth one last time, and the three boys started to get dressed. "That was awesome, Scott," his brother said. It feels like we just did all that to a 12-year-old." Andrew commented, "I still can't believe what he lets you do, and what he let that doctor do." "Prisoner," Scott said. Stay just like that until we're gone. I'll see you soon.