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You Can't Play Jackopoly With Pants On

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7 likes 1601 views Category: Masturbation Male-Male Tags: game, mutual masturbation, splashman


My story happened about ten years ago. I was 20, and home from college for the summer. My parents had a two-week vacation planned, and I was looking forward to having the house to myself. However, a week before the trip, my Mother announced that I would be spending the two weeks at Uncle Rick and Aunt Marci's. She said they need their house interior painted, and since I didn't have a job, I was to stay there and do the work for $5 an hour. I knew she mostly wanted to keep me from partying in the house with my friends. But heck, I needed the money, and I figured I could sneak back and use the house a few times anyway, it's only a half-hour away. (I did too, but that's another story.)
Uncle Rick and Aunt Marci have a then seventeen-year-old daughter, Kim, who is extremely hot, and a son, Alan, then 13. I was to share Alan's room. Neither Alan nor I were too enthusiastic about this. The first night, Alan peppered me with a lot of questions about sex with my ex-girlfriend, who I had just broken up with. I answered in detail (I think I was trying to impress him - she was may first). He expressed interest, but no real surprise at the things I told him. At one point he muttered, 'well... I know all about naked women from the fort,' but I couldn't get him to elaborate on the subject. Nevertheless, we kind of bonded that night.
The next day while I was painting, Alan came in. 'Want to come see our fort?' I speculated that he had some porno mags there. So, against my better judgement, I said 'sure.'
We rode bikes a few blocks to the woods, and then quite a while on a winding foot-trail way back in. Finally, Alan stopped beneath a very large tree and looked up. 'Bottoms up!' he said.
I looked up. Inconspicuously nestled among the leaves several branches up, I could see just part of a plywood tree house. A boy leaned out the window for a look, then quickly withdrew. There was a thumping commotion and urgent, hushed voices. A rope ladder descended. (I found out later they took their password from the show 'I Claudius,' which they revered for its nudity.)
We climbed up to a spartan, covered platform. Two boys Alan's age eyed me suspiciously. They seemed just a bit disheveled and flushed. 'This is my cousin, Mark,' said Alan. 'Don't worry, he's cool. I brought him to show him the trove.' He introduced the two as Dan and Ken.
'Well ... ok,' said Ken, casting me a last suspicious look. He leaned backwards and pulled a loosely nailed board out of the floor. Beneath was a secret compartment brimming with dirty magazines.
Ken started handing them out by the bundle. They were ordinary fare ... Cheri, Hustler, Penthouse. Probably a few dozen in all. There were some very old, very worn Playboys in the bottom of the compartment that Ken did not pass out. Pity, I thought, they'd be worth some money if they weren't so trashed. The boys immediately started flipping through the mags. Alan enthusiastically showed me his favorite babe, and I told him that I already had the issue at home (heh heh).
Shortly, two more boys, Steven and Kevin, arrived. The fort was now quite crowded, and it became obvious that each boy was fondling his crotch beneath the magazine on his lap. My semi-erect penis was wedged uncomfortably in a fold in my jeans, but I stalwartly resisted the urge to adjust it.
After about half an hour, Steven (who appeared to be the leader of the group) pushed aside his magazine. All eyes turned to him as he deliberately intoned 'Let the game ... begin.' The others repeated with mock solemnity, 'The game, the game...' Ken fished around under the Playboys and pulled out a worn, flattened box. It was a 'Monopoly' game. Except the M-O-N in Monopoly had been covered up with duct tape, and J-A-C-K was written in large felt-tip letters. The little Monopoly moustache-man sported a huge cartoon penis with splashy-drops squirting out of it.
Dan and Ken stood up quickly and started pulling down their shorts. In fact, all five boys were undressing. However, in a tense moment they all stopped and looked at me. Alan, especially, seemed imploring in his gaze.
'You can't play Jackopoly with pants on,' said Steven. 'It's the rules.'
They all looked at me as I sized up the situation. Either I take off my pants now and play a masturbation game with a bunch of horny little thirteen year-olds, or, I probably get kicked out of the tree house, to my cousin's embarrassment. I looked Steven in the eye, leaned back, and unzipped my fly.
The boys resumed undressing in a scramble, but they all shot sideways glances at me as I stripped. Soon, five half-naked boys sitting indian-style on folded pants surrounded me (none of them bothered to take off their tops). Each displayed a very hard, skyward-pointing erection. Ken and Dan set up the game, while Alan and Kevin opened magazines to their favorite pages and propped them up against the tree-house walls. Each paused frequently to fondle his own penis.
The old Monopoly board had numerous edits in tape and whiteout. For instance, the property 'Park Place' became 'Pork Place,' and 'Community Chest' was 'Community Breast,' with a little pair-of-tits graphic. Various clipped pictures of tits and pussies were pasted on the properties. I think I saw some semen stains. The 'Chance' and 'Community Breast' card decks were intermingled with hand-written index cards. I tingled when I imagined the edicts that must be written on them. Ken set a digital stopwatch in the middle of the board.
By the time I sat down, I was swept up in the sheer juvenile horniness of the situation. I had a raging hard-on. The boys stopped to regard it. Fortunately, at a fat seven inches (if I get to measure it right, LOL!), I was conspicuously larger than any of them. Kevin was their most developed, at almost six inches and with a fair amount of pubic hair. Steven was somewhat smaller with less hair, and the others were small and hairless. 'Whoa,' Dan said. 'It's like King-Kong over there.'
We began to play the game. It was like Monopoly, with a lot of twists. For instance, if you land on somebody's property, you get to try to jack him for X number of seconds, depending on the amount of money you owe. If you can make him cum, you are absolved of the debt. The boys bought up property as fast as they could, and vigorously wanked each other when they owed rent. (Later, I found out why they were all desperately splurging to buy hotels: a jacking becomes a _sucking_ once a hotel is present...)
At first, the stakes were low, and nobody came when subjected to a three-to-six second jacking (except Dan, who's little penis seemed to dry-orgasm virtually every time it was touched). It felt great, though. My first five-second jacking came when Kevin landed on Vagina (no longer 'Virginia') Avenue. I first delivered four seconds to Alan for J.O. Railroad. Whenever a boy was on the receiving end, his mates would chant his nickname, encouraging him to cum. Steven was 'the Duke,' Kevin was 'King Penis' (now supplanted by me, 'Emperor Penis'), and Dan was 'Weasel Peter.' They were obviously accustomed to having many orgasms apiece.
Then there were the card decks, and other extraneous rules. Various creative rewards and penalties were meted out in strokes or seconds, according to the roll of a die. Penises were tauntingly stroked in pairs and larger groups; players were held down, sat on, and blindfolded. Some rules were just juvenile or lame (for instance, 'cock in your ear'). The rule regarding jail was especially memorable. The players take turns being 'warden.' When another player lands in jail, he can challenge the warden to a duel. The two players face off and wank each other. If the inmate can make the warden cum first, he goes free.
Things got hotter as the game progressed. Ken landed on Alan's house-laden Atlantic Ave, and Alan squirmed perceptibly in anticipation of his twenty-seven second jacking. He lay back offering his penis, and Ken held his hand, claw-like, waiting for the timer mark. 'Ready-set-go,' said Dan as he clicked the stopwatch, with a suddenness I was becoming accustomed to. Ken grabbed Alan's little penis and absolutely wanked the bejesus out of him. Alan giggled, squirmed, thrashed, and otherwise went completely nuts. About twenty seconds in, he involuntarily shuddered, though no semen came out. For the last few seconds, he made a display of trying to look bored and annoyed.
'Thanks for the jacking, fork it over,' Alan said, trying to sound convincing. 'No way, dude. I felt you spaz,' Ken retorted. Alan hesitated, then sheepishly accepted the verdict. I think that was his third dry orgasm.
Shortly after, Kevin drew a 'Suck me 30 seconds' card from Community Breast. This first, coveted oral prize caused a lot of excitement. Thirty seconds was considered an impossible time to hold out, and Kevin is King Penis and all. We rolled dice and determined that Steven would deliver it.
Dan gave his 'ready, set, go,' start as he clicked the stopwatch, and Steven pounced on Kevin's penis with his mouth. Kevin reclined luxuriantly to enjoy the treatment. He was the only one (besides me) who hadn't cum yet, and everybody knew that this was his time.
Kevin enjoyed Steve's ministrations for a while, and then started to grow frantic. He clutched Steve's head to his crotch. His eyes grew wide as plates as Steve bobbed noisily. I glanced over at Dan's stopwatch. It read 38 seconds, far past the 30-second limit. Dan grinned back at me slyly.
Just then, Kevin screamed, bucked, and was finally still. All the while, Steven remained affixed. Finally, he lifted his mouth off and spit a big wad of semen all over Kevin's crotch. 'That's YOUR'S, dude,' he said as the other boys watched, impressed. Kevin was the only boy to really ejaculate very much, although Steven had produced some small droplets earlier. Steven looked at me and said 'It's not gay if you don't hug and kiss, 'n stuff...' 'Or butt-fuck,' offered Ken helpfully. I regarded Steven, who had a fleck of sperm clinging to his chin, and nodded approvingly.
The game continued. Next, I landed on Chance. I noticed that the card on top of the stack seemed a little more dog-eared than the others. They all paused breathlessly as I drew it.
It was the 'Get out of jail free' card, but it was edited to say 'Get jacked-off free.' The little jail-bird monopoly man had a giant penis with a hand stroking it. He was cumming like gangbusters.
'For how long?' I asked. 'As long as it takes,' was the reply. I later found out that 'Get jacked-off free' was the first innovation added to regular Monopoly, starting its long evolution into 'Jackopoly.' The boys were suitably solemn that the new one in their midst would be terminally jacked according to their oldest custom.
I didn't understand why, but it was decided that Kevin would administer the jacking. I leaned back to present my genitals, and the boys all crowded around to see the action up close.
Kevin did his duty, and yanked my crank vigorously. I think they were amazed to see someone not cum after about 30 seconds, but I was determined to enjoy the experience. I hadn't beaten off in three days.
Nevertheless, I soon began to lose control. I pulled Kevin's hands away and panted for a reprieve. He relented, and a few seconds later, Steven took his place.
For the next ten minutes, there was complete pandemonium in the fort. The boys chattered excitedly, and kept sneaking strokes at themselves and each other. Each time I was vigorously wanked to the brink, I would make my benefactor slow down. This was not their custom, but I argued that it was ok since there was no time limit anyway. Finally, while Dan was taking a turn at me, I began to lose control. I emitted a low grunt as he stroked, alerting them to the impending event. They all drew closer. Then, with Dan's small hand frantically milking me, I slipped over the delicious edge.
I knew that the first volley was going to be huge. As Dan gripped me at the base, I swiveled my hips and - I swear - I hit every one of those thirteen-year-old horndogs with my first blast of sperm.
Kevin recoiled and Alan laughed, but Dan got distracted by the spectacle. As a second stream began to fountain out of my penis under its own pressure, I clutched his shoulder and implored in a raspy voice, '...GO!!!!...' He got the message and got busy. I squirted five or six more huge blasts, howling all the while. These were aerial explosions that erupted upwards with such force that they broke up and rained down a full second later in a gooey thundershower. I got sperm all over the game board, on the boys, and even on some of the magazines. As I calmed down, panting and still leaking cum, they stared at me with mouths agape. 'Whoa.' said Steven.
I came three more times in the fort that day. For the next two weeks, I got to be part of their world. They wanked each other freely and relentlessly, whether in the fort, at home, or out and about. Although I was accorded special respect as the Emperor Penis, I was secretly jealous of them. I had had only a handful of awkward group masturbation experiences when I was going through puberty, but these guys were living a jack-off fantasy.
The second day, I bought them a bunch of new magazines. Just before I left, Alan had me buy several boxes of condoms. Much later, I found out that they got some girls to come out to the fort with them, and had used them all up.



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