My Sister and Me – Swinging into the New Year 2 – Happy New Year by bigpapa0u812

Rita was already in costume. She had on the flapper outfit I had seen her wearing at the Great Halloween orgy. I’d been working, and watched her take on all cummers. She became my fantasy girl, and I longed for the day I could fuck her. Of course that was before I learned that the flapper was my 16-year-old sister. That put a bit of a damper on that fantasy.

My original date cancelled on me, and I settled on not joining as a participant. No date, no play. So, when my sister proposed that I take her, I didn’t want to. Deep down, I still really wanted to go, and despite her being young, she’d already been to one. So, really, it would be okay because we both agreed that we were going to fuck anyone, but each other. We both said it was just wrong. Right?

Staff were’t supposed to be involved, but Layla, the coat check girl must have missed the memo. She was getting tag teamed on a pile of coats, with a mink coat stuffed under her ass. I walked in, and hung up our coats.

“OK, go have fun, I’m going to get changed. Let me know if you are going home with anyone ok?” I told Rita.

“Sure thing.” she said. She had on a tasseled flapper outfit. Traditionally, those were one piece get-ups, but hers was a two piece. The first part was a fitted mini skirt, and a straight cut top that flowed down to the skirt, giving the impression that he was waif thin. Rita’s pixie length hair was freshly cut, and she wore a beautiful white mask, with feathers, glitter and rhinestones. She looked hot. She was hot. Actually, the whole room was hot, so she decided to forgo the top, and put it with her jacket. Her pert b-cup breasts floated in the air, accented by tassels on her nipples. She know they would be lost, or become someone’s souvenir before the end of the night.

She walked down the stairs and to the bar. Suddenly, a person grabbed her, and pushed her against the wall, and planted their lips against hers. She couldn’t tell who it was at first, but she eased into the kiss. It was one of the club’s owners, and hosts, Maria.

“I’m so glad you got to come, my lovely little dove,” she said. She was already flying, but from what, Rita didn’t know. “Where is your date? I want to meet the man who was smart enough to bring you back to us. It wasn’t Davian, because I saw him with his latest toy, that cheerleader from Seattle. Gorgeous, but boring as anything. Everyone is jealous of him right now, but wait till she get’s put into the noob initiation, she’ll be a disappoint for sure.”

Maria was beautiful, and completely stoned. She began staring around having forgot her initial question. “I have to go mingle. At some point, your pussy is mine. Make sure it’s filled with cum when you come find me.”

That was going to be impossible tonight. One of the house rules is the only person to be able to cum inside you is the person you came with. Since Rita came with her brother, that wasn’t going to happen. Too bad that Davian dumped her, she missed the feeling of cum dripping out of her. Hopefully someone would at least cum on her pussy tonight. Actually, lots of people would cum on her tonight, or at least that’s what she hoped. It was time to go and make some friends she thought. A beautiful older blonde woman was stroking a young handsome buck with a zorro mask. She was busy talking, so Rita figured she would see if she could either borrow her buck, or get into a bit of fun with the two of them.

*****

I wandered into the room, checking out the sights. My outfit was a gift from Maria. My mask matched the one I had had for my original date, and had given to my sister. I guess it was a rule to match masks with your partner. The rest of the outfit was a half tuxedo, with chip n dale’s bow-tie, suspenders, a cumber bun, and tight shorts. I’d shaved his balls for the event, and was already sporting a semi hard bulge in my shorts. It was early, so people were mostly talking and getting to know potential partners.

My bosses, Maria and Eric cornered me. Maria giving me an intensely deep sexy kiss. “Oh Mike, I’m so happy you made it. Ever since I blew you that time upstairs…”

“You’ve blown Mike?” asked her husband Eric. “Fuck, I didn’t know that. I didn’t even know you were interested in him.”

“Oh, he caught Jorge and I in the upstairs bathroom. I thought I’d give him a treat to keep him quiet.”

“Oh. But everyone knows you and Jorge are fucking.”

“Not Mike,” she giggled, “at least until then.”

“You look fabulous, Maria.” I complemented. She did. She was a foxy older woman, in her early 40s, skinny and fit. She had an ass that she earned working out for two hours a day on a stair-master. Eric was lucky, thought Mike. Her mask was simple white mask with black feathers, and covered only the left side of her face. It was a sexy phantom of the opera kinda thing. Eric actually wore the mirror image of hers. It was a bit creepy, because it almost made them look like brother and sister when they stood side by side. It was hard to take my eyes off her as she was wearing a white garters and silk stockings, as well as a white bustier. She was sexy as hell.

“Michael, any time you see me tonight in a compromising position, shove your cock in me. Condom or not.”

“Ah my dear, that is against the rules. Mike knows that.” added Eric. “those shorts are fabulous on you.” and he smacked my ass. Then he whispered in my ear. “You know Mikey, if you catch me in a compromising position, you can fuck my ass if you want. I like it hard and rough. A bouncer like you could really make me jump.”

“I’ll think about that Eric.” I answered. Then I looked at Maria, “I look forward to finding you.”

“Oh silly boy,” laughed Eric. “You know you want me.I will turn you to the bi-way.”

I laughed as I walked away. Eric was wearing a bow tie… on his cock. Nothing else. I always thought he liked boys because of his favourites at the bar. I hoped I wouldn’t find him in a situation that I would say no to him. But I didn’t have any interest in fucking him or any other guy for that matter.

Then I spotted my sister. She was fist fucking a hot older blonde woman while the woman sucked a young man’s cock. Fuck was that sexy, I thought and felt my cock stiffen more. “No wait, that’s my sister,” I mumbled to myself. It was going to be a long night if he kept seeing her getting fucked like that.

People were starting to get stoned, and horny, so Maria rang the bell.

“Initiation time,” she said in a loud, yet sexy way. “All noobs please come and have a seat.”

I knew about he initiation, just not what it would be. I made my way to the ‘stage’, where my pants were removed, and I along with three other men, and a raven haired beauty, and an odd androgynous person were strapped to chairs. There were seven of us in total, and our legs were spread apart, so we were exposed to the crowed. Then, virtual reality headsets were put on our heads as a blindfold and visual stimulus. It was surreal. Then they gave us a pill – Viagra or something of the likes. Fuck, they played hard.

“Part one, we are going to play a game. Remember when you played 7-up in school. Seven people were up front, and went to touch one of their classmates. If you were touched when your head was down, you got to guess who touched you. If you were right, you were rewarded. If you were wrong, you had to sit down and sulk.

In our case, the people up front are the ones getting touched, and in some cases, someone may perform a sexual act on you. You have to guess who it was. If you are right, you will be rewarded, with $1000. If you are wrong, you lose, and get spanked. At the end of the game, the person with the most loses will wind up in the stocks and be at the mercy of anyone.”

“Now, there is a reward for the other members of the class. There will be four rounds, and if at any time, a ‘toucher’ can make you cum, that person is entitled to half of what you’ve won so far. That is if you guess who it is, because otherwise, they get it all.” Nice twist. To most of the people here, a $1000 isn’t really much. To me, it’s a month’s rent. I could use the money, so I hoped I could do well.

In round one, whoever picked me began to lick my package. It felt nice. The person began licking up and down my shaft, getting me super hard. There was a porno on my VR glasses, it looked like a similar event. Maybe it was footage from a previous event. This person knew how to suck cock for sure, because it was turning me on. They had something like a feather or a brush tickling my cock as they licked up and down. It was an enjoyable blowjob, and the video had distracted me enough to keep me from paying a lot of attention to them. And time was up.

“Head’s up, stand up if you touched,” called out Maria.

I opened my eyes and there were seven people standing in front of me. 3 Guys, and four ladies, including the blond who my sister had been fisting earlier. Her hair made me think she was my likely suitor.

The androgynous person was first to go. “I think it was Eric. Only he would be cheeky enough to suck me like my clit was a cock.”

“Sorry, my dear. But you can bet I’ll be at your chair next.”

Shit, I didn’t realize Eric was there.

The raven haired girl spoke next, “The person had an insanely long tongue. That would be Anna, I mean letter C.” I just noticed the people had letters around their neck, and we had numbers. I guess people didn’t really know each other, though obviously some did.

“How right you are,” said the lady I thought had done me. She wiggled her long tongue like a snake.

Everyone else had gotten theirs wrong after that, so I had 6 people to guess from. The only one I knew now was Eric, and I couldn’t put a feather or brush to anyone.

“OK number 7, your turn.” Maria called to me. I was still stumped. But then it dawned on me who it was.

“A,’ I answered. The croud oohed.

“How did you know?” asked a stunned Eric.

“Your soul patch tickled my cock,” I answered and laughs came from around.

“So did I manage to turn you?”

“I don’t think so. Now maybe if I had cum,’ I teased. More people giggles and Maria started us into round two.

This time I had an easy time. FIrst, I closed my eyes to the VR goggles, so I didn’t get turned on by the video. Then paid close attention to my suitor. In this case, I didn’t need to pay that much attention. It was Lady Letizia. She was a dominatrix who frequented the bar. A strong, and heavy woman, who manhandled my cock like it was a piece of meat.

I was now worth $2000, and not near cumming.

In round three, I had a problem. The person was wearing silk gloves, and merely caressed my chest, and cock, keeping at distance. Someone let go of a massive orgasm, most likely female. Someone had succeeded in making a person cum. Maria was even in line, but she was not one of the 4 of the 7 touchers wearing gloves. One lady’s were soaked. The raven haired girl easily guessed correctly, and gladly gave $1000 of her $2000 to the woman who had made her squirt. “Take me home tonight,” she told her ‘toucher’, “I’ve never cum like that before. I am yours.”

When it came my turn, and with odds of three out of 5 (obviously not Maria or Raven’s choice, I was still wrong. Oh well, I was gonna be spanked later.

IT was the final round. I was pretty confident that I would walk out with at least $2000 in my pocket. I was a little careless, because I was startled to see what was on my VR. It was the Halloween party, and in the middle was a girl in a swing. To be more precise, it was my sister getting gangfucked. My fantasy was on the VR and I was riveted by it. My toucher started sucking my cock hard from the start. I was completely fucked, because the video had me turned on completely, and this little cocksucker was a pro. She had me at the brink in no time. I head grunting and the sound of two of the other contestants cumming beside me. I was fighting a losing battle trying to keep from cumming and just as time was called, my cock errupted. I let go three massive squirts of cum.

As we were un-blinded, there were seven people in front of us. A tall African lady was licking a smidgen of cum from the corner of her mouth. A redheaded guy who had cum dripping from his face. He could barely see from being cum blinded. Lastly, there was my sister, three blasts of cum across her chest. Oh fuck.

The androgynous person, I still didn’t know if it was a guy or girl, was first to guess, and finally called her ‘toucher’ right, and got herself a $1000, and out of danger of being put in the stocks. Next, a fellow picked the African beauty. “I felt her swallow every drop.”

“No, we’re sorry.” said Maria. Someone had just taken that guys $2000.

It was my turn. Was it the guy, or my sister. THe three stripes had me believe it was her, but my mind didn’t want to believe it was her. I decided to guess the guy. “I think it was the g….g….girl in the flapper skirt.” I don’t know what made me change my guess.

“How did you guess?” I sister beamed. A 16 year old thrilled that she’d just won $1500 buy making a guy cum. I don’t think it settled in her head that it was me. Fuck, who would have guessed that my sister’s greatest performance on video would help her make me cum. Fuck.

The game was over, so I thought. Then, it was time for punsihment. The biggest losers were put into the stocks. A cute, but poor guesser of a light brown pony-tailed cheerleader type seemed thrilled and immediately began blowing a cock that was stuck in her mouth.

Then the rest of us had to kneel on our chair ass in the air. The people who tricked us, got to smack us. Maria came up and grabbed my balls. “Oh, dear, dear, Michael. You didn’t even think it was me did you.”

“Fuck, really? You didn’t have gloves on.”

“Oh, but I did earlier tonight.”

“Shit.”

“I will make you a deal, I will be gentle, and you will have to cum for me later tonight.”

“You, don’t have to be gentle.”

“Oh, I’m not giving you a choice. Your load is mine now.” and she tapped me on the ass lightly. Her voice was full of mischief, making me wonder what she was up to.

I was looking for my sister, wanting to talk to her, when the ebony goddess from the game came up to me. “You need to be aware boy. Maria has plans for you. She was directing the game that involved you.”

“Oh, I wonder what?”

“Oh, don’t worry. I’ve known her for years. She and Eric are good people. A little kinky, but good. She has plans for you, and whatever they will be, you will enjoy it.” Then she kissed me, and pushed me into a nearby chair. She took a rubber from a nearby fishbowl, put it in her mouth and rolled it onto me with her lips. I was still rock hard, as she game me a few pumps with her lips.

“I wanted to mount you the moment I saw you, but Maria and Eric blocked me during the game. I will have you now.” and she lowered her pussy on my cock, and began to ride me. She rode me hard, bouncing up and down on my cock. When another couple came over and tried to join, she growled at them. “He’s mine for now. I will come for you later.”

When they left, trying to keep her breathe while riding me, she said, “That was my partner. He likes little brunettes, but is scared to fuck without me around. I will punish him later.”

She got off me, and kneeled on the next chair. I entered her doggy style, and began fucking her hard. She was moaning and grinding back into me as I pistoned forward into her. Maria walked by and dropped a beautiful glass butt plug into me hand, and kissed me. “She will love that,” she whispered. I slowed down and slid the little plug into her ass.

“Oh, fuck,” she moaned. “Where did you get that?”

“Maria,” I said as I began pumping her harder.

“Oh god, I have to thank that woman properly later.” And she began cumming. With each thrust, she moaned louder. My cock was being flooded buy her pussy juices. I didn’t know if I should stop, as some of my previous girlfriends liked, or give it to her until she passed out. I chose the latter. I fucked her harder, pulling her ass into me. She came harder. Finally, she pushed back. “Stop, stop. I won’t be able to fuck anymore if you keep that up.”

I stopped.

“You are going to have to give me your number before we leave tonight.” and then she just walked away.

i lost count of how many women I fucked that night. I have to admit, I wanted to catch Davian’s cute cheer leader in the stocks before they let her out. It had been hours, so I doubted I would find her, but decided to check anyway.

There was the perfect heart-shaped ass staring at me from the stocks. Light brown hair was bobbing up and down, sucking on Eric’s cock. It ws like that pussy was waiting for me.

And then a silk glove began stroking my cock as we walked over to the stocks, “Oh, I finally found you.” Maria said. “It’s time for me to collect. This load is mine.”

“I was hoping to get a piece of that first,” I said pointing at the stocks.

“Oh, perfect. You can fill that up, and I will lick it out. But first drink,” she said handing me a cocktail glass.

Immediately my cock felt like it was growing. My mind felt like it was growing. My reality was stretching.

“What the fuck was that?”

“I call it a “Little Bit”, it’s got a little bit of this, a little bit of that. It’s like ecstasy, but milder, and really, it’s better. It will make you cum like it’s the first time in a month. You will feel every millimeter of your cock, gush in pleasure as you fuck that pussy. Everything will be heightened.” She explained. “I hope you don’t mind. Later, when you are balls deep in my ass, you will feel every spasm as I cum, but first, you need to make her cum, and cum in her.”

And she led me right up to the cheerleader, and guided my bare cock into the girls pussy.

“I though this was against the rules.”

Maria moved behind me, a hand still on my cock, and she pushed me into the girls pussy.

“Fuck her,” she whispered seductively into my ears. Who was I to argue, she was the boss. She was the host, and later, I was intending on fucking her.

I was fucking the girl with good hard strokes. This girl was fucking amazing, it may have been the drugs, but I’d never been so turned on.”

“Enjoying fucking her?”asked Eric.

‘Yes, fucking great pussy.” I replied.

The girl turned around and looked at me. She was beautiful. “Fuck me harder,” she pleaded. I stared in my sister’s beautiful eyes, and thrust harder.

Then my mind caught up, this wasn’t the cheerleader. This was my sister. I was bareback fucking my 16-year-old sister, and fucking loving it.

Maria was caressing me, and reached between my legs, and began squeezing my balls and licking my back. “You brought her,” she said. “Only you can cum in her.” Oh fuck, that’s it. They think she’s my date. Oh god, what do I do? Maria’s massaging of my balls was bringing me to the brink of cumming. “You owe me this load, Mike. Cum in her pussy. I want to eat your load from your hot sister’s pussy. Cum for me!”

She new! Maria knew!

I looked into my gorgeous sisters eyes, once more. “Fill me up.”

I was confused. Maria squeezed my balls harder. I thrust harder. My sister began spasming in her own climax. I lost control, three more thrusts and I was filling my sister’s cunt with my sperm. Oh fuck!.

My mind was completely blown. My cock was spent. Maria and Eric took turns licking cum off my cock and out of my sister’s pussy. I was completely fucked up.

After that, I remember being led to Maria’s office and was sitting on the couch. Rita was there beside me.

“What did we do?” I asked, still in shock.

”Mike, I didn’t plan this.”

“Neither did I. I thought they were getting us to fuck because you were my official date.” I paused. “But Maria knew. how did she know?”

“I think I told her at Halloween. We got to know each other in their office, after. They didn’t mind that I was under aged, they kinda figured it out. Then we talked about family, and I think I mentioned you. They never let on that you worked for them.”

“But why then? Why if they knew?”

“I don’t care,” she said. She pulled my head up to hers. “It was incredible.’

“But you are my sister. I love you.”

‘I made you cum from a blow job. That felt so good. And you made me cum like I’d never cum before.”

“That’s the drugs.”

“No, I didn’t take anything. Look Mike, tonight was amazing. It was better than I could have ever hoped for.”

“I love you too, and what better thing than to be fucked by someone who loves you.”

She hugged me. And then she kissed me. At first it was a sisterly kiss. Then, it became more passionate. Our tongues wrestled in our mouths. My cock, was hard again. And it happened again. I didn’t even expect it, but somehow, my sister was on top of me, and my cock was in her, and we were having sex. Actually, we were making love. And it felt amazing, and that wasn’t the drugs speaking, they had worn off quickly. My sister road my cock gently, and then rolled backwards off me, onto the couch. It was a huge couch. I eased into her missionary style, gently thrusting my cock in and out of her pussy. Our mouths engaged each other as I slid in and out of her pussy. My cock was drenched by her juices, and our bodies slapped together as I began thrusting into her harder. She pulled her legs behind her head, as I neared my next climax. It tightened her up, and drove me over the edge. I came hard for the third time for my sister. Then, I ate my cum out of her pussy and fingered her until she came again.

“That’s fucking sexy,” Maria’s voice startled us from our pleasure. “Don’t you think so Brother?”

“Kinda glad we got Kristy that plane ticket, and got Davian that boring model girl,” replied Eric. “Don’t you agree Sis?”

Did I just hear what I thought I heard? Did I catch that Eric and Maria aren’t husband and wife? They are actually brother and sister? What the fuck???

To be continued.