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Rated: GC · Chapter · Adult · #2043156
John plays Strip Monopoly with his Friends.
John Benson was feeling quite relaxed on his spring vacation, yet the current situation was not as relaxing as he had hoped; Jenna had invited him over to have some fun, considering his past experience with Jenna, he had hoped that this was her implying that they would play another strip game, and they were going to do just that.

Unfortunately, Jenna also invited two more people, his friends Emily and Richard, both of them enjoyed playing strip games with before, however, as much as he enjoyed it, he was hoping that this would be a more private affair.

They had sat around facing each other, in particular, they sat around a monopoly board, ready to be played; this was their strip game for the day.

Jenna had already begun explaining the rules:

Instead of each play starting with $1500, each male player receives $650, and each female player gets $500.

Clothing can (and will) be used as legal tender at the following amounts

underwear: $500
bras, brassieres: $300
pants, shorts, sweats: $200
shirts, tops: $200
socks: $ 50 each
shoes: $ 50 each

No other clothing is allowed to be used as legal tender. That means no hats, no jewelry, no watches, no tampons, no sunglasses, no jackets, nothing else.

Each player is allowed to start off with ONE item from each of the previously listed categories (but two socks, and two shoes), only female players are permitted to start with a bra or a brassiere. (Pants, shorts, and sweats is one category.)

Clothes can be used to buy property, buy houses and hotels, pay debts, pay fines or anything that money can be used for, they can also be sold at a higher than list price and/or auctioned off at any time that the rules allow a player to auction property.

You're not out of the game until you are out of money and clothing. This means that if you land on someone's Boardwalk with a hotel and can't afford to pay the rent, the owner can take everything you have but leave you with one dollar, to keep you in the game.

After a player loses, they must take one forfeit from each of the players still in the game, which means that the first loser must take three forfeits, the second, two, and the third one forfeit.

As the game began, everybody rolling for their turns, and buying whatever properties they could land on, that is, except for John.

John had the exquisite luck of continuously landing on the chance and community chest spots, collecting all manners of small monetary gifts, at first it seemed like a lucky streak for him, though his lack of properties had started to get him worried; everyone else had about three properties already, he was still left with none.

However, he'd managed to finally land on an unowned property, Illinois Ave., unfortunately for him, since it was his first, it was rather unimpressive.

Even more unfortunate for him, the next property he landed on was owned by Emily, and so his recent earnings dropped just a little.

At this point, everyone but John had removed their shoes and socks, on account of the properties they'd managed to buy, Jenna had even removed her top, giving everyone a good view of her bra and ample busom.

The game continued on for a couple of turns, John managing to gain one other property, however, about half of the board has already been occupied by his three opponents, which started to give him a hard time.

And then disaster struck, John landed on the "go to jail" square, meaning that about six turns into the game, he'd been sent to jail with about the same amount of money he had begun with and only two unrelated properties.

At the tenth turn when John was finally released from jail (he'd failed to roll any doubles at that point), the game was well underway; Rich was in his shirt and boxers already and was doing fairly well, while Emily was already down to her pink panties due to some bad judgements, her pink (and hard) nipples were on display, and although Jenna had lost her pants as well, she'd done so well so far as she seemed to be controlling about one third of the board.

This posed a problem for John, for despite his fully clothed state, he doubted that any of the other players would be willing to sell him any properties, as they could simply wait him out and bankrupt him without any effort.

And so it happened, bit by bit, John was hemorrhaging money faster than he could imagine, it didn't take long before he was down to his last dollar, and completely naked even before Emily.

As he rolled on what was probably the 20th turn, John finally landed on a property owned by Jenna, who took his last dollar and declared him the first loser.

"That means you'll be taking a forfeit from each of us, however, we'll leave that until the end of the game." Jenna declared, as John was relegated to the side to watch the rest of the game.

The very next turn was Emily's last holdout, she'd landed on one of Jenna's most expensive properties, and seeing how she was already struggling, this meant that the panties had to come off, leaving her with one dollar.

As to be expected, the next turn was Emily's last, marking her as the second loser, and recipient of two forfeits, one from Rich and another from Jenna.

With only two players on the board, the game was coming to an end quite quickly, Rich was attempting to hold out for as long as he could, but in the face of Jenna's overwhelming resources, it was a losing game to begin with.

It was finally time for Rich to pay up his remaining dollar, sitting there naked with his 8 inch penis that was plainly erect, much like John himself.

John was actually a basketball player, which meant that his physique was a lot more appealing than John's something both he and the girls noticed and appreciated, even the naked Emily had an impish grin on her face as she stole glances at Rich's rigid member.

"Alright, since I'm the winner now, how about we start with the forfeits?" Jenna seemed excited at the prospect of watching everyone performing for her pleasure "Emily, since you only have one forfeit for John, why don't we lead with that?"

Emily looked at John excitedly, but he knew that Emily didn't have much of an imagination for forfeits; she tended to ask for one thing and one thing only:

"I want to see John masturbate for us." Emily met John's expectations quite nicely, at least it was one forfeit he didn't have to worry about getting out of hand; he'd been made to masturbate to all three separately at some point.

"Ooh, that's a good one," Jenna clapped her hands together, but her eyes seemed to stray over to Rich "so good, in fact, that I want my forfeit to Rich to be the same thing."

"Oh, we're doing this now?" Rich seemed a tad acerbic at the prospect, he turned his head to Emily, who seemed taken aback at this turning against her "Alright then, I want Emily to masturbate with us."

And thus the impromptu masturbation session began, all three sitting facing each other, legs splayed open to display their privates in the most revealing fashion, all while Jenna clearly proclaimed that she was going to record it, while John seemed indifferent, unsurprising due to the amount of footage taken of him already, and Rich seemed almost welcoming to display himself, Emily had been a different case.

While she knew that she enjoyed stripping and displaying herself in public situations, the idea that she might be recorded doing it was a relatively new situation for her, she always assumed the risk was there, but experiencing it was an all too different sensation altogether, the permanence of it was what simultaneously worried and excited her the most.

The two boys began stroking themselves as they took sideways glances to enjoy their mates' bodies, Emily's fingers were busy circling her clitoris as she bit her lower lip, already quite aroused, the ever present hovering of the camera made sure that she felt on edge, something she felt was beginning to wane from her own displays in public, she hoped it didn't show too much how highly enjoyable this was to her.

The first to approach orgasm was John, he began to feel his throbbing penis approach its limit as he began moaning, surprisingly enough, this seemed to have an effect on his partners, who also began enjoying this more than before.

It didn't take long before John blew his load into his own hand, panting heavily as he watched the remaining two make bedroom eyes at him and each other, both dangerously approaching their limit.

The second to reach orgasm was, oddly enough, Emily, her juices flowing out onto the wooden floor finish, she convulsed before the three in ecstasy as wave after wave of pleasure coursed through her body, which left her panting, waiting for the holdout, Rich, to finish and blow his load.

But before Rich could hit his climax, Jenna stopped him, and although he seemed to struggle, Rich obeyed the order.

"John and Emily, for your second forfeits, bring Rich to orgasm with your mouths." Rich's strained face seemed to flip into a more excited one, as one tended to when faced with the prospect of a double blowjob.

Hesitant, the two approached Rich's throbbing manhood, Emily was the first to take the cock into her mouth, she bobbed her head a few times before moving her head to lick the shaft from the side, John followed suit as the two covered the length of the shaft with their mouths.

It was then that Rich told John to take his cock into his mouth, John obeyed and took the hard shaft into his mouth, Rich was beginning to moan when he heard Rich talking:

"Do I get to choose where I can cum?" Rich was apparently asking Jenna.

"Knock yourself out." John heard Jenna responding.

"Alright, you can stop now, John." Rich said with a struggling tone, clearly very close to orgasm "Emily come over here."

John backed away, only to see Rich stand up, taking position in front of a kneeling Emily, who understood what was about to happen and closed her eyes, expecting the oncoming load.

After a couple of strokes, Rich grunted and emptied his load onto Emily's face, the semen spurting out and covering her face, the amount was so copious Emily seemed taken aback by the amount, which began dripping off her chin and onto her chest.

After Jenna offered Emily a towel, who giggled as she wiped the load off of her face, she turned to John and assigned his final forfeit:

"John, you are going to be spit-roasted by me and Emily." Both John and Emily were taken by surprise; despite their numerous games together, the two had not engaged in any direct sexual acts, not even oral sex, the most they'd done was bring the other to orgasm with their hands.

As Jenna began instructing Emily in how to put on and use the strap-on she'd brought, she put on her own and told John to get on his hands and knees, as he did, John glimpsed Jenna move behind him and heard the pop of a lube bottle, certainly enough, he felt the cold trickle of the lube flowing down onto his anus.

"Here I go." Was the last thing John heard before Jenna inserted the strap-on inside him, he grunted as he felt it slide inside of him, however, his grunting was soon muffled by the second strap-on that intruded into his mouth, and soon he was being rocked back and forth between the two girls as the strap-ons slid into and out of his orifices.

John didn't know how long they kept him like that, but it was only punctuated with a few comments and giggles from the girls as they continued to spear him, as well as a couple of times when John gagged on the strap-on in his mouth, eventually, Jenna seemed to have had enough.

"well, that was fun." Jenna exclaimed as she pulled out of John, the strap-on popping as it left his cavity "Did you have fun, John?"

"Yeah, I guess..." John said as he took the second strap-on out of his mouth, when it became clear that he was sporting another erection, which was still unattended.

"Aw, you look a little worse for wear..." Emily commented and giggled as John seemed to blush while she removed her strap-on.

"Well, we can't have you going home dissatisfied, come on, lie down." Jenna said, and John timidly lay back on the floor "Emily, sit on his chest, and gently, give him room to breathe."

"Um, okay..." Emily nodded, and proceeded to straddle John's chest, who could feel Emily's exposed (and rather soaked) pussy pressed against his stomach.

That was when John took in a sharp breath, as he felt something warm on his erect cock, he couldn't see what was happening, thanks to Emily, who turned her head to see what was going on, and was smiling when her head turned back and looked at John.

From the sensation, John guessed that Jenna was giving him a blowjob, who he, at best, could barely see behind Emily, the sensation as Jenna's mouth continued to glide over his shaft was blissful, her tongue running over the tip, tickling its underside and caressing the skin beneath it, John closed his eyes and enjoyed the show.

It didn't take long in John's mind before he felt himself approaching orgasm, and his grunts grew louder as, finally, Jenna's mouth left John's penis and he felt her hand beginning to jerk him off, when finally he came to a climax, his semen flowing out from his loins and onto Jenna's hand, the relief came with a sigh.

Finally, with the game and its consequences over, Rich told John and Emily that he'd be driving them home, when they asked for their clothes, Jenna refused to hand them all over, she gave Rich his pants and shirt, Emily her panties, and John nothing, before ushering everyone out of the house and into Rich's jeep.

during the ride home, Jenna opted to sit in the backseat with John and Emily, unfortunately (or fortunately), Emily was stuck in the middle, which meant that she was the focus of a barrage of molestations and kisses by John and Jenna.

At first she giggled, but soon Emily began to moan from the attention directed at her body, so enthralled by the care she was given, she failed to notice her panties being slid off her legs and being pocketed by Jenna as her fingers intruded into Emily's eager pussy.

Sadly, Emily did not find release in the car, as the attention ceased the moment they'd arrived at her house, and what's worse, Jenna refused to return her panties to her.

The car sped away before Emily and John realized that they didn't bring their keys or wallets with them, and thus were stranded completely bare out in their neighborhood, Jenna's house wasn't that far, but it would certainly be interesting regardless of what they decide to do.

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