Strip Monopoly

I’m Clara. My brother Jimmy and I are only 10 months apart in age. A little over a year ago we started Masturbating Together and have been pretty open about it with each other ever since. It's not like we do it all the time though. Privacy still has its place. However, it is strictly between us and absolutely NO ONE knows what we do. Neither of us ranks very high on the attraction scale so we get our jollies solo, just occasionally in each other's company that’s all. 

This day I was having a relatively new friend come over for the weekend. She's a girl I met at a study group I joined to bolster some grades I was having trouble with. The group met in a nearby church basement and she was there as a home-schooled student getting some advanced teaching her parents couldn't handle. Cindy is my age, a cute girl, prettier face than mine but verysimilar physique. We are both kinda pudgy with full hips and fairly large breasts. She has a flatter tummy though.

Her parents had to go away for the weekend and they didn't want her to stay home alone, so they agreed to let her stay at our place until they returned Sunday evening. It was Friday and I had just got home from school when Cindy's parents dropped her off around 4:30. It was pouring rain. Cindy ran from the car up the driveway to our house and was soaked by time she entered."Oh my god I can't believe how wet you can get in just seconds!", she exclaimed. "Would you have a towel I could use Clara?" Cindy asked politely. "My hair is going to be ridiculous in five minutes" she added with a giggle. Her long blond hair would soon be curled up into rather nice natural waves that was a look she really should have gone with. Her hair wasn't the only thing soaking wet as her clothes stuck to her like she wore them into the pool. "Come to my room and get those wet clothes off, they must feel gross" I suggested as Cindy followed me up to my room with her back pack of necessities in tow. She quickly removed everything wet, her bra and panties managing to stay dry enough so she kept them on. "Hey, we might as well just get into something comfortable”, I suggested “I will too since we're just gonna be hanging out here tonight anyway by the look of the weather", I added. It was raining hard and getting colder outside.

We heard the door slam; it was probably my brother Jimmy getting home from work. "Hey anybody home!" we heard him yell out. "Yeah, me and Cindy are here!" I yelled back. We got our comfie’s on and headed down to see what Jimmy was up to. "Holy shit it’s getting miserable out there", he exclaimed. "I think it's gonna snow!" he added curiously. "Hey Cindy," he said with a smile which I noticed made her blush. Just then his phone rang so he answered it, "yeah...really? okay I guess I can", he said as we listened to half the conversation. “I will mom, don't worry, we're grown up now” … okay bye, we'll see you whenever it's safe". Jimmy hung up the call and proceeded to tell us it started snowing and the roads were horrible. “Mom and dad were staying put and won’t likely be home tonight and dad said I should put a fire on in the fireplace as it's supposed to get pretty cold". He stated. "Oh wow", Cindy and I said simultaneously. "Well, if you do the fire Cindy and I will get dinner starting in case we lose power or something," I added. 

Cindy and I dug around and found all the ingredients to make a rather exquisite meal for the three of us. Her being from a somewhat religious family and Jimmy and I both having imbibed with friends since reaching legal age we decided it would be fitting to have some of my dad's home-made wine with our meal. Jimmy had a nice fire going as the three of us sat down to enjoy our dinner. How romantic it seemed to all three of us we began talking about relationships. Cindy seemed enthralled to ask Jimmy all kinds of questions about what he did with his friends and what boys thought of girls and what he wanted in a girlfriend. Jimmy was pretty good about it but the curiosity about all her questions was starting to come through. "Hey I gotta go shower," he finally stated, "would you girls mind if I skip the dishes?' to which Cindy immediately proclaimed, "no problem, bro, we got this!" we giggled and Jimmy smiled a wide grin at her eager comment. “Okay I won’t be long, not going out in this weather so you guys come up with something to do”, Jimmy said as he went to shower.

Cindy and I had everything cleaned up and sat down in front of the warm fireplace with another glass of wine. We felt so adult. The fire was hot on our outsides and the wine made us warm within. Cindy then asked me straight out, "have you ever seen a real cock?" I laughed a bit nervously as my mind immediately went to the secret my brother and I kept. "I never have" she trailed on. "Well of course I've seen Jimmy's when he's coming out of the shower with nothing but a towel on" I threw back at her, adding "and I've seen them in porn videos". Cindy chirped back loudly, "YOU WATCH PORN VIDEOS", obviously surprised. "NO, I don't watch porn silly, but of course I've seen them here and there, haven't you?" I retorted. Cindy went on to explain she had never seen one other than babies or in pictures and recently she was wondering a lot about what they were really like. She added that she knew she wanted a boyfriend and she better have some idea of what to do with one or what’s expected of her. The wine wasreally beginning to take effect now as our discussion became wayyy more open. "I wonder if I’ll ever see Jimmy's?" she asked me straight out, as though she would be privy to him after showers as I am. I could feel that make me blush. We went on joking with each other about penises, laughing and giggling like silly girls. "Hey what’s so funny?" Jimmy blurted out as he entered the room just as we brought ourselves under control. "Oh nothing!" Cindy and I said simultaneously again. "So, what are we all gonna do tonight?" Jimmy asked as he sat down cross-legged on the floor in front of the fireplace. “you two figure out something fun to do?” 

Cindy blurted out, "let's play strip poker!", then laughed out loud again as she looked over at me. "Oh man" Jimmy said, "you girls are crazy already, how much wine have you had?” “Maybe Monopoly or something would be more appropriate?" Cindy blurted again "How about STRIP MONOPOLY?", with another bout of laughter to go with it. Jimmy looked over at me and I looked back at him and winked and smiled as he started to grin. "Okay", he said, "since Cindy wants to get naked, STRIP MONOPOLY it is then!" "How does strip Monopoly work" he added confused. "Well," Cindy went on, "we just change the meaning of the Chance and Community Chest cards stating which piece of clothing comes off for each time you get those cards, usually Chance is for lower clothing and Community Chest is for upper and if the card is in your favor, you can force someone else to take a piece off, if it’s a negative card then you have to take it off". It sure appeared like she had played it this way before. "Cool" I stated, "lets do it!" Cindy added "Oh, we should all start with the same number of clothing items to make it fair". We agreed each of us girls hadtwo upper and two lower pieces. I had my bra and a T-shirt, panties and house pants, Cindy had a bra and button up pajama shirt, panties and shorts, Jimmy had a T-shirt, tighty-whities and sweat pants. We gave him a head band to round out the upper wear, two item necessity, which he looked so eighties in!

We set up the board "Let the games begin!" Jimmy shouted as he rolled the dice, counting out his moves on the board. With the wine having all of us warm inside and the fire beginning to get pretty hot outside, landing on the Chance and Community Chest spots was beginning to be a bit of a goal. We talked and laughed as we played the game, no one hitting those spots for what seemed like forever. Then finally Jimmy hit Community Chest, he immediately lost his headband. Then I hit Chance so had to remove my house pants. Luckily my T-shirt was long so I could cover myself down to my knees. A few more rounds and Jimmy lost his T-shirt, then Cindy finally got into the game with a Community Chest so she had to lose an upper piece. She expertly shucked her bra from under her shirt without missing a beat. We played and talked and laughed, drank wine, the conversation getting a bit more risqué as the evening and wine wore on. Then Cindy got a positive Chance card, taking the opportunity to make Jimmyremove a bottom piece, no way he could remove his underwear from beneath his sweat pants without taking them off first and the rules didn't allow that (so we said). SO off came the sweat pants! I focused on Cindy as he rose up on his knees, pulling his waistband down his thighs, then sitting back on his butt as he pulled them the remaining way off his legs. Cindy's eyes were glued to him the whole time, staring at the bulge revealed in his tight, cotton briefs, only looking away when he finally got the sweats off and returned back to sitting with his knees bent to one side, leaning on one arm, his cock and balls were clearly distinguishable from each other, bunched together nicely. Cindy looked over at me with a grin, her face was flushed.

We hardly traded any properties as we went through the motions of the game, mostly focussed on trying to hit Chance and Community Chest now. I was getting pretty horny. I glanced over at Jimmy's package a few times and I was surprised he stayed in such control. His cock was pretty big so if it started getting hard there was little chance it wouldn't stick out, literally! The nextroll was Jimmy’s and he hit a positive Chance card, giving him the right to make one of us remove a bottom piece. He took the opportunity to get back at Cindy, making her remove her shorts. She did the same as Jimmy had done to remove his sweats, up on her knees, pull down the shorts, then sat on her butt to slide them off her legs. As she did this however, she fully exposed herpanty clad pussy to my brother. I looked on as Jimmy’s eyes locked on to her swollen labia bulging out the thin cotton panty material, a dark line of wetness showing through. Although a brief glance, that was all it would take for Jimmy’s bulge to start growing. His member began extending, but he managed to keep it directed to the side so at least it wouldn't pop right out. Heblushed as he looked at both of us. Cindy looked right at his growing bulge then over at me again, her face really flushed with a slight smirk of a smile. Then I rolled the dice and hit negative Community Chest. I was hot so I just pulled my T-shirt off which left me in my bra and underwear. I knew this wouldn't be good for Jimmy either. It wasn't. His cock had grown to where it was a thick ridge from his ball sack all the way to his left hip bone. I think Cindy and I were pretty much staring at it too. He must have been in agony. As we rolled and rolled the dice, so horny we were seemingly just trying to get naked now, the talk in between, depending on the topic, had Jimmy shrink and expand several times. It truly was amazing to see a cock do that, each time oozingclear pre-cum out the tip, creating a large wet spot near his hip. I almost gasped out loud one time I looked when he was getting hard and his cock head rested right in the wet spot, which made it cling to his skin tightly, exposing the reddish, purplish head in all it’s glory.

We all knew the next one to hit either spot was gonna cause the most revealing. I knew Cindy was praying to hit a good card so she could finally see his cock in the flesh. Karma must have been playing along too as she got a negative Community Chest card and we all groaned with laughter knowing she would have to expose her rather nice young breasts. "COME ON!" Jimmy and I both exclaimed taunting her to take her shirt off. She giggled and stalled as we chided her. Finally, she started undoing each button from the bottom up as Jimmy and I sounded the worst porn music you’d ever heard. She held her undone shirt closed as she lowered her head, looking down she slowly removed her shirt then immediately crossed her arms over her tits in a vain effort to conceal herself. She had real nice tits. "COME Onn!" we moaned again, "no hiding now" Jimmy added, his cock now growing back toward his hip. Cindy finally dropped her arms, then leaned back onto her hands fully exposing her breasts to us and actually thrusting her chest out a bit. Jimmy said quietly "wow" as he moved to control his erection as best he could by sitting cross-legged and leaning forward, making sure his cock stayed inside his briefs. I just looked on at the both of them, clearly duelling with each other now. Cindy looked down at Jimmy's cock as she also repositioned herself cross legged, still leaning back on her hands with nothing on but her frilly underwear, her pussy barely concealed by it. Jimmy took her all in. I looked at it as his cock throbbed and more clear fluid oozed from it. Jimmy was struggling as his cock clearly wanted out of his underwear. I was struggling as I really needed to cum with him.

Cindy looked at Jimmy, noticing how large the ridge had become and said sarcastically, “Is it getting hard for you?” in a sultry tone, grinning from ear to ear. “No harder than it is for you two!” he immediately threw back at her, pointing his finger at each of her VERY erect nipples, even her areola were puffing out. Laughingly Cindy quipped back, “HEY YOU!” as she lurched forward onto hercrossed knees and thrust her arms into Jimmy’s shoulders, pushing him hard! The force against him was enough to rocker him over backward, his crossed legs not enough leverage to counter balance himself so he ended up in his sitting body position only on his back! Then, as he lowered his crossed legs to sit himself back up…it happened… by stretching his body out straight, the waistband of his underwear could no longer restrain his fat erection as it freed itself from being bent toward his hip, popping out dragging a thick thread of clear fluid from his hip to the slit of his cockhead. It now pointed straight at his chest, right up over his belly button! Thick and full and veiny and pulsing harder.

Cindy gasped as she said, “OH MY GOD I’M SORRY!” putting her hands over her face pretending not to look. Jimmy pushed himself up onto his elbows, realizing half of his cock was fully exposed and looking at both of us to gauge our reactions. I just smiled at him and gave him a shrug while Cindy lowered her hands and looked, then looked away, then looked, then looked at me, thenlooked again. “Well?” Jimmy said, “guess I won’t have to hit Chance to get all naked now, will I?” He added, “does this mean I win or lose?” We all laughed and I said, “put that thing away that was an accident”. Jimmy grabbed it with his right hand and tried to return it to within the waistband of his underwear, but to no avail. The kink now removed, there was no way it would bend back tothe side. Another throb and more pre-cum oozed from the tip. Jimmy blushed and apologized, “sorry guys, this is embarrassing”, “can’t seem to do much about it though,” as his hand just held his member, it looked pretty obvious to me he really wanted to start moving it up and down.

Cindy openly stared at my brother trying to arrange his throbbing member back into his underwear. She looked over at me and quietly asked me rather curiously, “and they fit those things inside of us?”. I chuckled and replied, “so they say”. Jimmy gave up trying to stuff his hard on back into his briefs, finally dropping his hands to his sides with his cock still pointing out from thewaistband, straight up his abdomen. “can’t do much about it girls, whadda ya think?” he asked. “Ummm… it’s a nice cock?” Cindy said sheepishly. “No silly, but thanks for that, I meant whadda you two think we should do here.” Jimmy said. “Well, I’m fine with whatever you’re comfortable with”, Cindy proclaimed. “I don’t care bro, take’em right off if you want”, I added. “Yeah okay”, Jimmy stated, “the waistband is kinda cutting into me”, he spoke as he rose up on his knees, slipped his thumbs into his waistband and sliding his underwear down his thighs, finally completely revealing what Cindy was after all along, his full cock and balls bouncing free as the elastic flipped past and down his legs. He lifted each knee separately, moving his underwear off his legs and discardingthem to the side. As he knelt upright, slightly thrusting his groin forward, he looked down at the cute girl sitting across from him, gazing straight at his erect cock, his completely shaved ball sack and groin area now in the open. She looked up at him and giggled with a blush “OKAY, okay I’m staring at you, but I’ve never seen one for real before and its kinda cool…okay”, Cindy said. Jimmysat back onto his calves, still kneeling. He could tell her interest was genuine and he was very much enjoying it. “What?! seriously, you’ve never seen a man’s cock before?” He quizzed her. “No bro”, Cindy answered.

“Well technically each of us is still wearing at least one piece of clothing, two for me”, I suggested, trying to deescalate the sexual atmosphere, “might as well make someone a winner, shall we?” SO, we started rolling the dice and playing the game, still not as much interested in a Monopoly winner as a last one clothed winner. We laughed each time one of us rolled, counting out what number we needed to hit Chance of Community Chest, with plenty of sexual inuendo to go along with the palpable eroticism in the air. Cindy’s bare chest right in front of Jimmy was enough for his cock to remain hard and with that, a frequent ooze of pre-cum that he nonchalantly would spread over his cock head and down his shaft with his fingers right in front of us, getting a littlesensual relief each time. I caught Cindy squinting at him as he did this, as though she was kinda puzzled. Then she finally asked him, “Why do you keep doing that?” “Saving it for later” he replied as they both smiled at each other. Then I rolled onto a Chance spot and got the card I needed! I rolled onto my back without hesitation, raising my legs into the air and slid my crotch-soaked panties off my legs. With my legs still straight up in the air and held tightly together I knew my pussy would be visible to my audience, holding that pose briefly to give them a healthy view, Cindy whistled a cat call just as I lowered them to one side.

“Geez, I can’t believe how open you two are in front of each other” Cindy said as she rolled the dice. “But I guess it’s too late forembarrassment”, she added as she counted out her spots on the board. Jimmy and I just looked at each other to confirm our secret would remain hidden. Then Jimmy rolled a Chance and got the card that would have actually removed his underwear under the rules. “What do I get to do for having already taken them off?” he asked, clearly expecting a reward for his early exposure. Cindy looked at me and I looked at her then I suggested, “how about you get to choose which one of us takes off their last piece, thereby YOU get to decide the winner!” Cindy’s mouth dropped as she started to protest but then stopped, realizing it was inevitable at this point that we would all be naked within a few minutes. “Yeah, okay”, she said, “you get to decide the winner”, as she smiled at him. I kinda wondered if he wanted to pick me so that she won, or would he be overwhelmed by a need to see her pussy and thus have to make me the winner to make sure she didn’t put clothes back on after the game ended.

Of all the things, Jimmy did an eeny-meeny-miney-moe, THE WHOLE VERSE, to try and determine who would win and which girl would get completely naked first. Well, the thing with that verse is you can manipulate it any way you want or just decide to use the last one you land on or the opposite of that. As expected Jimmy made the safe choice, as far as ensuring Cindy’s crotch wouldget revealed to him, by choosing me the winner. Cindy tried the same as I had removing my panties except, she forgot to hold her legs together, instead slipping her panties up her legs, bending her knees to reach them off her ankles, then returning to a cross legged position like she had been in! Her swollen labia glistened from her juices as did mine. There was gonna have to be some major relief taken by all of us at some point soon.

Cindy seemed to think nothing of her complete nakedness in front of us. I wondered how such a reserved kind of girl to become so open so quickly (she later told me it had a lot to do with the wine). Since I had won the game, I right away shucked my bra to catch up with the naked duo. There we sat, three young, horny, naked bodies pent up with sexual tension but not sure what to doabout it in front of each other. “I can’t believe we’re all sitting here naked together”, quipped Cindy. “And super horny”, Jimmy added. “Yeah, I guess that too, cum to think of it”, Cindy said, as we all chuckled at her pun. Cindy was staring at Jimmy’s cock again; it had softened somewhat as it had been doing while contained in his underwear a while back. “Is it always getting hardlike that on you guys?” Cindy asked Jimmy. “Yeah, at least mine does, I think it’s the same for most guys”, he replied. “How do you guys deal with that all the time; it’s got to be pretty uncomfortable?” she queried again. Jimmy answered rather openly, the wine and circumstances getting the best of him, “well I have to masturbate a lot, sometimes twice a day, but usually at least once”.“Holy shit, really!” Cindy proclaimed. “Hey I do it almost every day, except for that time of the month”, I said matter-of-factly. Cindy looked over at me and then back to Jimmy and then asked us, “how long have you guys been masturbating?” … I was sure she was going to add the word together as though she had somehow found us out. We had both been masturbating for years now, unbeknownst to her we had been doing it together for over a year. “Well, I just started doing it a few months ago”, she said, eyes still locked on Jimmy’s cock, her right hand slowly caressing her tummy back and forth with a glazed look in her eyes, the wine had clearly taken affect. Jimmy was staring at her too, her full firm breasts and puffy, erect nipples causing his cock to fatten and grow freely, it pulsed to full erection quickly, the head turning from dull pink to deep red, more pre-cum oozing from the tip. “Oh-my-gawd this is so hot!” he said as he stretched backward, thrusting his erect member forward as it seemed to grow even bigger. Jimmy had a truly large penis and balls, especially for his lanky young frame. “I think we should all enjoy a real good orgasm together!” he added, reaching for his cock but still reluctant to jerk it in front of us without our approval or something. For quite some time now I had one of my hands behind my back and had been occasionally running my fingers between my wet lips without the other two noticing. I was all up for fingering my super horny pussy to a cascading orgasm but thought I’d better let Cindycome to terms before saying anything.

Jimmy’s cock began to stream pre-cum from itself now, the constant arousal over what had been nearly a couple hours now putting him in a state even I had never seen. Cindy’s constant intrigue kept her attention and questions for him, I could tell he was hoping she would either grab it and jerk him or at least let us all get onto doing it for ourselves. “How come you guys have so much leakage like that?” she asked him, adding “does that happen throughout the day?” “Cindy”, Jimmy responded, “this has been a bit of a weird night here, I’m just super, super horny right now and this is what happens when guys really need to cum bad”. Cindy looked up at him now, “so you want to masturbate right now?” Jimmy answered emphatically “oh gawd do I ever!” Cindyasked sheepishly, “will you do it in front of us or do you have to go somewhere else?” Jimmy looked at me, knowing it would likely seem weirder to Cindy than it would be for us to masturbate before each other and not knowing how to address it. So, I chimed in, “All things considering, since we’ve already crossed the naked bridge, getting off on front of my brother doesn’t bother me at all, so I hope it doesn’t bother you either bro” with a wink I made sure Cindy didn’t see.

Jimmy leapt to his feet and exited the room, the look on Cindy’s face clear disappointment until he said from a distance, “I’ll be right back!” Cindy leaned back, closed her eyes and pushed her hand between her legs briefly as she said to me. “Fuck I really need to cum too!” Then giggling as she noticed how wet her hand was. Soon, to her delight, Jimmy returned with a tube of KYand sat back on the floor in front of her, pulling a nearby chair up behind himself to lean on. “Okay girls, y’all ready now?” he said as he opened the tube and dolloped some of it’s liquid onto his cock head. “I’ve been ready for over an hour!” I said as I laid right back, closed my eyes, spread my legs and began softly caressing my wet pussy lips, waiting to hear the tell-tale sounds of Jimmy sliding his hand over his slippery cock. Cindy sat on her knees across from Jimmy, eyes glued on him as he was about to begin masturbating right in front of her. She came over wondering about seeing a boy’s cock, and was now getting the fullest exposure a boy could give. This would be Jimmy’s first time in front of someone other than me and the excitement it was causing him waspalpable.

He let the KY slowly slide off his cockhead and down the front of his member, mixing with his own copious precum as it did. He watched Cindy watching him before he let his hand near himself, delaying the satisfaction for both of them as long as he thought he could. “Well Cindy?” he said softly, “are we doing this together or do you just want to watch?” She shrugged her shouldersand kept her gaze at his cock as he wrapped his long fingers around it’s base, slowly sliding them upward, spreading the fluids along his cock’s length. When his hand reached his glans, he twisted it to cover as much skin as possible, then slowly he pushed his hand back down, spreading the lube on the other side of his cock and trying not to look too eager. Cindy took a deep breath. She glanced around, seeing me getting right down to business, she slightly spread her legs and moved her hand into her crotch letting out a quiet whimper as her fingers brushed her clitoris. Jimmy let out a little moan too as he began stroking in earnest. Cindy focussed on him and also began masturbating herself honestly. She moved from sitting on her knees back to the couch front, spreading her bent legs right opposite Jimmy.

The two of them began masturbating to each other, Jimmy taking in her sexy body as he pumped himself slowly, so as not to cum too soon. Cindy’s eyes fluttered as she slid her fingers between her labia, gathering her juices and spreading them over her clit. She began circling her aroused clit with her middle finger pressing into it, her other fingers rubbing her labia as she did. Her breathing was quick and short, she would let out a little gasp with each one. Jimmy and I moaned as each of us raised our level sexually manipulating our organs. I raised my head to see the others, each working alone yet partially focused on the other, no one said a word until Jimmy began quickening his pace. “Gotta cum soon”, he said in a gasping tone, his hand now pumping hiscock from base to tip, just two fingers touching with such a slight contact causing every ounce of blood rushed to his erection to accumulate within it making it as large as it had ever been. Cindy let out with “FUUUCK!” as she was now vigorously massaging herself while staring at Jimmy doing the same. “Is…that…thing…gonna…burst… or what?” she said between breaths as shequestioned Jimmy’s now massive cock nearing his climax. “AHHHHH!” Jimmy let out as he thrust his hips forward and pressed his hand down onto his cock. Cindy’s words triggered his orgasm and a thick, pearly white stream of sperm laden semen burst out and onto his chest from his belly button up to his neck. Immediately a second, third, forth and fifth rope pumped out. Cindy cooed, “ohwow that’s soooo cool, heyyyyy!” as her own orgasm, triggered by Jimmy’s, began to make waves over her body. She began to shake, her breasts heaving and jiggling and her legs shuddering, she clamped them together onto the hand still n her pussy as a pulsating flood of extasy cascaded over her.

The two of them having already cum, sitting there huffing and puffing, it was my turn as I rapidly flicked my clitty with one hand while my other was buried two fingers deep inside. I usually cum with a significant amount of goo and this time would be no different. I gulped as I neared my orgasm then let out a loooong moan. My thrusting fingers got coated with white jism as my firstcontracting wave came over me. I removed them and another flow of cum sprayed out onto the floor as I kept flicking my clit, then another and another as finally my orgasm subsided, I laid back gasping for air and moaning after such a major climax. “Holy fuck that was awesome!” is all I heard someone say.

“I think I can cum again”, Jimmy stated as he began pumping his still fat, full cock again. Cindy giggled as her hand went back to her crotch.

This would be one of the most amazingly sexy nights ever!