Cowboy Monopoly

"Yesss," I whispered back shyly while thinking it might be more fun to stay home and explore this new side of our relationship.

"Time to go!" Sadie abruptly announced. "I'm going to get my stuff on and then we are leaving. Put the boots and hat on." She walked out, and returned a bit later with a second bag. In front of me she stripped naked, pulled on a matching wife beater, and tight cotton briefs that were thin enough to show the outline of her inner curtains. She had a black cowboy hat, and matching black boots. We exited and loaded up in her truck.

On the way there, Sadie ask me to turn my legs towards her. "Why?" I asked.

"Because I'm going to gauge when I can and cannot see your pussy so you'll know how to sit." What followed was a hilarious game of shifting and sitting at various angles. Our conclusion was that if my legs were parted much at all, my jewel was on display. The house party was supposedly over an hour away, but it seemed like we arrived in less than half that time. When we walked up to the door step, the butterflies in my stomach were so bad I almost vomited.

Sadie rang the doorbell, and a second later we were greeted by Rob. He was a little over six feet, with steel blue eyes and very fit. I shook his hand politely and entered. There were probably about twenty people there and crazily all dressed like us. Just the view made me smile. How could you not, right? Sadie let me know that Rob had an identical twin brother Bob who was also here.

A minute later, Rob appeared at my side and introduced himself again, except this time he was Bob. They were identical. He asked for $10 dollars as a participation fee. Sadie gave him a twenty, and in return he handed us each a wad of Monopoly money. Supposedly, five-hundred dollars of funny money.

"How about we get ourselves some drinks, and then mingle?" Sadie asked.

"Sure," I replied as my eyes wondered the crowd. There were several attractive people present, and most of the ladies had on a top through which one could make out the outline of their nipples. This helped me to relax. We wondered out of the living room and into the kitchen where a large high-top desk served as bar-complete with three stools in the front of it.

A middle-aged man was sitting on the far right bar stool, so Sadie sat down on the left one and I took the middle stool. She ordered us each a shot of tequila, and I was surprised that they charged us each twenty dollars. Apparently, this was a high end bar. After a bit we included the gentleman in our conversation. The party had started two hours ago and we'd missed two of the mandatory dare rounds.

I asked about the dare rounds and he explained that during a round each person had to issue dares to another person, and couldn't dare one person more than once per round. Also, a single person was banned from partaking in more than three dares per round. Naturally, I asked what happened is someone didn't do a dare.

"Oh, there's nothing complicated about it. Either you do the dare for the dared price, or you pay the person that amount. But if you run out of money, then you have to strip naked until someone earns your clothes back." Now the challenge of the event was recognized by my brain. I didn't ask how someone would earn their clothes back.

"Interesting," I replied. "How did your dares go?"

"Very well. Mind if I buy you two another round?" And before we answered two more shots of tequila were poured for us. I accepted the drink, but let him know I had had enough alcohol for a bit.

I turned towards him and asked, "Can you only do dares during the rounds?"

"No. You can issue a dare any time you like. And, by the way, nice view." My face turned beet red as his eyes were aimed right at my crotch. Immediately, I closed my legs and turned away. "Don't be embarrassed. It is beautiful and looks freshly shaved. Surely, you anticipated others would get to behold such beauty?"

"This is my first Cowboy Monopoly party," I mumbled and turned back towards him, but this time making sure my legs were not parted.

"How about a dare my dear?"

"I don't know. It's early. It might be best to wait to get going until I have a chance to see what the other dares are," I replied.

"Young lady, you either accept or pay me the wager. Oh, and wagers over $100 are not allowed. Here it is—you simply sit there, but with your legs parted wide until you've consumed a glass of wine. Of course, no gulping. The wager is for $75 dollars, and I'll make sure not many notice," the gentleman offered.

I realized I was in a pickle and started to count out $75 dollars. "Don't be stupid, this is as easy as it gets and you'll appreciate the money later on," Sadie advised.

With her advice or pressure, I relented. "Ok," and slowly I parted my thighs. The gentleman ordered a glass of merlot for me and moved his stool so he was directly in front of me. Meanwhile, the bartender served a glass of red wine filed almost to the rim.

I took a sip and felt awkward as the guy in front of me locked his eyes on my pussy. It was weird, but also reminded me of when the people were watching me at the beach crag.

"A little wider sweet one. And let me move some of the fabric. It reminds me of an orchid, and I can tell it is a touch swollen. Do you like knowing I can fully see your flower?"

"She loves it. She's shy. Already her breathing has gotten faster," Sadie added. "I bet she's hoping you'll touch her." The last comment caused me to take a healthy drink of my wine.

"Hmm, would that be fair play under the dare?" the man asked.

"I don't see why not," Sadie answered. "Let me show you the beauty of her orchid." She reached across, placed one hand on my vagina and with her fingers opened my inner lips.

"Swollen and moist, just my type," the man added and again I took another sip.

"She wants your fingers to explore her sex," Sadie tossed out. My face again turned crimson. "Look how erect her nipples are." This brought the eyes up to my chest to confirm the point, but soon they wondered back down. "Go ahead, she won't wait forever."

The man extended his arm out and used two of his fingers to lightly tickle my inner thighs, slowly, very slowly bringing them closer and closer to my sex. When his fingers were less than an inch away he pulled them away and placed them on my other thigh, far from my crotch. He repeated this process twice. I responded by spreading my legs even wider and this time when his fingers were close I pushed my hips out. Hoping to force contact. Easily, he avoided my thrust.

"Do you want to feel my fingers in your pussy?"

"Yesss," I softly whispered.

"Pour some wine onto it, and then I may." My response was to place the rim of my glass directly above my vagina and slowly coat it with red wine. I didn't worry about staining my shorts. Quickly, his fingers were exploring my sex. Outer lips, inner lips, teasing my clit and then pushing up into me. All I could do was lean back against the bar, and bite on my lip. His exploration transitioned, as he started to pump two fingers in and out of my sex while using his thumb to tweak my clit. Sadie reached across, and pulled up my top to expose my tits. He reached down and sucked hard on each of my nipples.

"She probably wants you to fuck her," Sadie advised. "Lately, she has been dreaming of a stranger taking her."

"Ohhh fuckkk. Don't stop, just keep doing. Ohhhh," I mumbled.

"Maybe later. Maybe the both of you," the gentleman answered. Then he asked me, "Do you want to be fucked?" His thumb was pressing harder against my clit and flicking rapidly.

"Ohhh, ohhh, yesss, ohhh shit. I'm goinngggg to cummm," and I did. When my pussy became too sensitive I pushed his hand away. He pulled his fingers out of me, and pushed them into my mouth. I cleaned them off, and thanked him.

"Dare well done my little flower. Enjoy the wine and we will certainly dance again." Then he was off to another room. I looked up and saw a few people looking hungrily at me. I turned around to face the bar and avoid their looks.

"That was amazing. You even made me horny," Sadie added.

"Can we step outside. I need some fresh air," was my response.

"Sure, just follow me." Sadie lead me to a back door that exited onto a deck. There were two couples outside, but they were engaged in their own conversation.

"Shit Sadie. I don't know what overcame me. That is not who I am. I just get so hot, and feel powerless to stop. Maybe we should leave?"

"It's ok my dear. There is nothing wrong in enjoying your sexuality. Didn't you have fun?"

"Yes, but it seems so wrong now," I answered.

"But you enjoyed it, he did, as did I and a few others in the room. In fact it was uber sexy. You should be proud."

"Really?"

"Yes. Definitely yes. If you are unsure it is fine to say no. I don't want you having regrets."

"But, Sadie. I wanted to him to fuck me. I don't even know him."

"And your point is? Just remember, I love you and you're awesome. Ready to go have some more fun?"

"I guess," and to myself I thought I will not let my libido get the best of me tonight. Quietly we re-entered the party house. Sadie introduced me to a few friends, and again the dress of everyone made me smile, plus some of the people there couldn't help themselves. A few cocks were making tents, and some of the gals had spilled or wet their shirts so their tops were see through. It was a damn sexy vibe. A couple of minutes later, a bell rang out loudly.

From wall speakers, a loud voice announced, "Time for the next dare round. Have fun, and don't do anything I wouldn't do." This was followed by the whole group rolling their eyes and laughing. A couple of minutes later, a beautiful Persian woman walked up to me. She looked like a model. Long straight dark hair, tan eyes, slender build and full exotic lips.

"I dare you to kiss me for $50 dollars?" she stated in a sultry voice. My response was to smile and confidently step towards her. Our arms embraced around one another, and for a bit we just smiled and eyed each other. Slowly, our lips drew near, touched and it started. A slow intimate kiss, that gradually grew and a short while later flames were ignited.

Our mouths felt like they couldn't get enough of each other, while our bodies pressed against one another tightly. It wasn't long before her hands were roaming over my body. Slipping underneath my shorts initially to fondle my bum, then pushing them down to expose my sex. Quickly her fingers were spreading my lips and sliding up into me. She knew how to tease a woman. With her other hand, she started to twist and pull on my nipples. Somehow, this lady made me feel like I was in heat all over again.

Her play also made me curious, and for the first time I played with another woman's tits. Her breasts were much fuller than mine, but with small nipples that made her flinch when I pulled on them. And then I lowered my hand down and started to rub her pussy through the cotton fabric of her briefs. It wasn't enough. Gently, I eased my hand down her underwear and parted her lips with my fingers. Pushing a finger up into her, and then gradually adding a second one. I couldn't believe how wet her pussy was.

Briefly, we paused our make-out session, allowing me to ask, "Do you always get so wet?"

My friend responded, "I get fairly wet, but I'm a bit creamy down there. Two have already taken me." She pressed her open mouth back to mine, swirled her tongue about mine before pulling back again. "Pull your fingers out and taste me."

I thought about it for a second. Then did as she asked. I placed two fingers in my mouth and sucked on them hungrily. The taste was unique. Semen and something else. It was her. Her pussy juices. After the taste, I resumed our kissing and hungrily returned my hand to her vagina. I wanted her. As we made out, I played with her pussy and clit just like it was my own. It didn't take long before she was moaning and shortly after cumming.

"Oh, my god. I can't believe you did that with just your fingers," my friend stated as she backed away from me. "Can you do me a favor please?"

"Sure," I responded.

"During the next dare, will you dare my husband to kiss you? He is the one that greeted you. I'll be standing next to him."

"Ok," I answered. She pulled up my shorts, gave me a peck on my lips and wandered off swinging her sexy hips. I really wanted more of her. When she disappeared, I looked around and was surprised at the events around me. A lady was blowing two guys in one corner, the older gentleman was eating out a girl on the couch across from me and just then Sadie walked up. Her tank top was torn so one of her tits hung free, the cotton fabric around her pussy was soaked and her hair was a mess. She looked like she'd just been fucked.

"One more minute, and let's wrap up this round. The final dare round will be in thirty minutes," the loud voice announced again over the speaker.

"That lady you were with is beautiful," Sadie commented. "Did you enjoy her?"

"Yes. She's so sexy."

"There's a minute left. Do you dare me to kiss you?" Sadie asked with her eyes full of desire.

"Ok," I replied softly and that was all it took. Sadie pressed her open mouth to mine and promptly had her fingers twirling through my sex. She pushed one, two and then three fingers up into my wet pussy while using the thumb of her other hand to tweak my clit.

Our kiss was fast, but Sadie pulled back and asked, "Are you having fun?"

"Yessss," I moaned out.

"You wanted to fuck her didn't you? To eat her pussy until she came over and over?" Sadie asked as she continue her assault on my crotch.

"Jesus fuck. Ohhh shit Sadie. Yess, yessss I want her," I admitted.

"And you want to be fucked right now. I saw how your eyes looked when you say the older guy again. Right?"

"Yesss," I answered as I bit my lower lip. "Ohhh god, I think I'm going to cummmm. Please don't stop," I begged. And that is exactly what Sadie did.

"Bitch! Why did you stop?"

"I want you to be so badly in heat you would beg someone to fuck you," Sadie replied.

"Shit. I was there a while ago."

"I know. I love it. Do you want me to touch your clit again?"

"Yesss."

"Pull your boxers down and take them off. Just leave them on the floor. I don't think you'll need them for a bit and everyone will be able to see your delicious ass." I did as she asked, and when I stood Sadie placed one finger on my clit and lightly traced her finger around it.

"Use your fingers like you were before," I pleaded.

"You want more than a touch?"

"Yes."

"What do you want?"

"Please do it?"

"Say what you want," Sadie demanded.

"Screw my pussy with your fingers."

"Do you want just fingers, or would you like cocks and tongues exploring every inch of your body?" With this question out, she shoved two digits into me forcefully. I felt great, but I wanted more. "So, what do want?"

"Everything," I answered as I pulled the palm of her hand up against my mound and ground my clit into it.

"Should we host a cowboy monopoly party at your place next weekend?"

"Oh shit." The thought was sobering, yet I loved the idea of a repeat. "Ok," I answered after a brief pause. And Sadie pulled her hand free.

"Let's go get you a drink. It'll allow for people to view one of the most amazing asses ever made. And I'll show you some of the other rooms to get ideas for next weekend. You know, they say the hostess always gets the mostess." Sadie grabbed my hand and led me back into the kitchen. This time we didn't sit, but instead each purchased a glass of red wine. She gave me a tour of the upstairs portion of the house.

There were some cool features, including a sex swing in one bedroom, a hot tub just off the back deck I hadn't noticed earlier, and a waterbed. As we walked around people did notice my ass. Several pinched, smacked or rubbed it and while we were standing in the kitchen the older gentleman gave it a nice massage and twice dipped his fingers into me. All of this just made me want more.

Eventually, we returned to the living room. It was the largest room of all and where most of the people were moving into. In the center of the room, my Persian friend was standing next to one of the twins. I gathered that must be her husband and recalled the dare I was going to ask him. His shirt was off and there was an obvious bulge in his briefs. Briefly, I daydreamed about him, and a couple of minutes later it was announced this was the last dare round.

Immediately, Sadie was approached by a blonde man carrying a large dildo. "I dare you to fuck yourself with this while sucking my cock," he dared her. I was a bit shocked as I'd never thought of such.

Sadie grabbed the piece of plastic from his hand, used a suction cup to stick it to the floor, pulled down his briefs and replied, "Ok, but only if you find someone to fuck me afterwards." She didn't wait for an answer, but instead squatted above the tip of the toy cock and guided it into her opening. Once it was halfway in, she brought the fellow's cock to her lips and started to suck on it. I couldn't believe the way she looked, almost as if she was possessed, yet so fucking hot. Was that how I looked I wondered, then I remember my dare.

I turned and saw that the host was still in the living room, right next to his wife and surrounded by five or six people. My hope was that I could catch him alone in a corner as I felt embarrassed to have to ask for a kiss. His body was hot, and the bulge remained. I wondered if I would feel it press against my wet opening when he kissed me, and what if he declined. Oh god, that would be really embarrassing. While these thoughts raced through my mind, his wife saw me and shot me a smile. Now, I felt compelled so I slowly walked over. All around me, people were starting to engage in various sexual acts.

When I walked up to him, he turned to me and smiled, but didn't say a word. At the same time, his twin brother also approached. I was worried he might pull him away so choppily delivered my dare. "Hi, can I or no, I dare you to kiss me for $10."

"Accepted," was his only response. He pulled me towards him and seemed to tower over me. He put his toned arms around me, and latched his hands directly to my rear. "You've a perfect ass. My brother and I were commenting on how it bounces when you walk. It makes us want to fuck you."

"Thank you," I innocently replied. He responded by lifting me up by my bottom. I thought it was to give me a kiss, but he kept on lifting, raising me higher and higher, until my crotch was right before his face. "Rest your legs on my shoulders, I'm going to start kissing you."

Oh shit. I couldn't believe it. I angled my thighs over his broad shoulders and he lifted me a bit higher until my lips were inches from his mouth. He flicked out his tongue, then pulled me towards it. Initially, he just teased me with faint swipes of the tip of his tongue. It felt sexy, as everyone was now watching us. I realized the angle was off a bit so I placed one foot on his shoulder to push on, and raised my hips up so they were just above his mouth. This give him full access to my sex.

Instantly, he was probing my canal with his tongue and a minute later transitioned to my clit. He alternated between sucking on it forcefully and blowing while pressing his lips against it which caused his lips to vibrate strongly against it. It caused me to twist, push and gyrate my mons into his face. At the same time, I was trying to pull my vagina away from him, and push it harder against his mouth. It was exhilarating. His wife pulled up a chair behind me, made a few sexy comments to me and started to kiss and lick my behind. When her tongue found my sphincter it almost sent me over the edge.

"Do you like that? Do you like having your anus and clit played with at the same time?"