Big Sister in the City

"One night with me, boy" She growled, as she slowly ran her hand up my thigh "And you wouldn't be able to walk for a week."

I couldn't take my eyes off of hers. That is until her hand reached my crotch. Then I jumped and fell off the back of the couch. Both of them burst out in laughter, just as my sister came in. I couldn't see her from my vantage behind the couch.

"Come on you two. You have all night to mess with my poor little brother. Don't break him so early." She joked.

I got up and saw my sister standing there with a big grin. Now, she may not have been dressed as scantily as her friends, I thought she was stunning. A ruffly kind of pink satin button down shirt, hugged her just right. A pair of tight white pants covered her long legs and showed off her toned behind. She finished it off with three inch open toed heels. And she had apparently put in her contacts. She extended her hand towards me.

"So little brother, you ready to hit the town with three of New York's finest?" She said, posing as her friends took up positions on either side. I stood there speechless for a minute before finally nodding vigorously. They all laughed as they swarmed me and dragged me out into the big city.

It was too early for the club, so we started with dinner at a nice uptown restaurant. Good food, great wine (they didn't card and my sister insisted), and amazing company. Each of the ladies I was with were intelligent, interesting, and funny. And let's not forget; Damn Sexy.

After a long wonderful dinner, we slowly made our way to the girls' club of choice. Chosen not only because it was one of their favorites, but because they knew they could manipulate the doormen to let me in.

The club was trendy, and while not full had plenty of people in it. As soon at the music hit them, Denise and Esther started moving to the beat, swaying so wonderfully. We found a booth and the ladies ordered drinks. I wasn't much of a drinker. Plus I wanted to keep a cool head. The ladies were all very touchy feely. Even my normally calm and collected sister. And not just with me...with each other. Which in some ways was even more stimulating.

Eventually the girls wanted to move to the dance floor, and one of my weak points was revealed. I didn't know how. Well, I could slow dance. I had done that at prom, but regular dancing wasn't something I ever had the chance to learn. This fact in no way deterred my entourage. In fact, it simply spurred them on. I was pretty adamant about not making a fool of myself. But Josie had a plan.

"It's simple. You dance, facing me, and I'll help you get the hang of it. Denise and Esther will flank you and make you look good until you know what you're doing." I had to admit, it would probably work. With those two gyrating around, no one would even know I was there. I admitted defeat and they dragged me out to the floor.

Josie tried to show me some stuff, but I moved awkwardly. Stiff and nervous. Not to mention, I had Esther and Denise's butts, breasts, and hands touching me quite often. But it was really watching my sister swivel her agile waist and hips that had me the most unfocused. After a few songs like this, my sister took charge. She stopped my horrible dancing and stepped in close, our eyes just inches apart. I've always thought my sister's eyes were beautiful. The looks she gave were captivating. And the intensity she had right now practically burned my eyes.

"Brian. You need to be confident." She said, just loud enough for me to hear. "And you have every reason to be." Then she put her hand on my chest. "Handsome, charming, and sexy. You have three of the hottest women in this club at your beck and call. And you could go home with practically any woman here. So show them all that you are the stud that I know you are!"

And I believed it. I knew that what she just told me was true. At the very least she believed it to be true. And just like that, a switch was thrown inside of me. I started dancing again. My movements loosened up and I began to get into a groove. And before I knew it, I was dancing.

Now, sure, I was far from being a master. But I looked decent enough. And once I got into it, the girls began to really dance with me. I took turns with each one, bumping and grinding. I had a blast. And I knew I was the envy of every guy in that place.

I don't know how long we had danced, well over an hour, but we sure worked up sweat. Eventually the girls wanted more drinks, and we went to find a booth as Denise headed to the ladies room. She tried to get at least one of the girls to go with her (like women do), but they both grabbed one of my arms and said there was no way they were leaving me alone with one of the other. So Denise made a pouty face and walked off.

Drinks flowed, with me partaking in some, but not near as much as the others. Josie and Esther were extra flirtatious with me, talking about how sexy I was out on the floor. Esther bluntly admitted that I had made her 'horny as hell'. Denise eventually emerged from the ladies room, but was intercepted on the way back by some guy near our table. It was quickly apparent that Denise had no desire to talk to the guy, but he had her blocked. He was lucky it wasn't Esther he was dealing with. I was betting she would have just kneed him in the groin instead of trying to politely get away. I sprang from the table when he started getting handsy with her. I could see her light up as I came over and tried to rescue her.

"Hey, buddy." I said, gently grabbing Denise and pulling her to my side. "This lovely lady is with me." He made a face and looked over at our table.

"Looks like you already got your hands full." he grumbled, motioning to my table a few feet a way.

"First off," I said, stepping up to him. "I've been keeping all three of these visions more than happy, all night long." Denise molded into me and put her hand on my chest.

"He sure has." she said with a grin.

"And second, this sensual beauty is far more than a guy like you could ever handle." Denise just grinned at him.

I could tell he wanted to hit me, but wasn't sure how that would turn out. Track has kept he in really good shape. He backed down and grumbled "whatever" as he walked away.

Denise turned to me and shouted "My hero!" and then threw her arms around me and kissed me deeply. And it was not a casual or friendly kiss. Full blown, passionate, tongue filled kiss! She broke when Esther called out "Quit hogging our man!" She pulled away and flashed me that brilliant smile and led my stunned form back to the booth. My sister gave me a sly lopsided grin, that told me that not only was she not mad, she seemed a bit proud. Like a 'go get `em, tiger' look.

"Your brother is a great kisser!" Denise said as we sat down.

More drinks, lots more flirting, and tons of innuendo. I was constantly playing footsie with someone. They were all very impressed at my white knight showing. Even though I hadn't drank very much, I was intoxicated. The girls however, were quite drunk on alcohol.

Denise and Esther decided they wanted a bit more dancing before we left. Josie, however, claimed to be too drunk. They turned to me, and I fought them off, saying that I was going to keep Josie company. Rather than fight, they gave each other a look, grinned, and left us alone.

Once gone, Josie snuggled against me. "I was hoping you'd stay. I haven't had almost any alone time with my favorite guy." I put my arm around her and hugged her into me, and we just sat there enjoying each other's presence.

The music changed to something slow and Josie perked up. She pulled me from the table and found a nice out of the way place nearby. She began slowly swaying, her hands around my waist. I put my hands on her hips and moved with her. For the longest time I simply lost myself in those baby blue eyes. The look she gave me was a mix of intensity and adoration. Eventually she pulled herself closer, putting her hands up my back and resting her head on my shoulder.

"You've been really amazing tonight, you know that don't you?" She whispered. Her breath on my neck sent shivers down my spine. I just mumbled something nonsensical.

"And it won't be long before I lose you to Esther or Denise...or both. I've never seen them take to a guy like this." More shivers.

"You're not going to lose me to anyone, sis." I managed to get out. I really wasn't sure what was going on. I knew right then, in my heart, I would pick Josie over either of her roommates without hesitation. But I also knew she was very drunk, and probably didn't realize how she was coming off. Or would even remember this in the morning. But what I said seemed to placate her.

"Hmmmm...I hope that's true." She said in a dreamy voice.

The music had long since changed, but we were in our own world. We didn't stop until I saw Esther and Denise returning. I tapped my sister and she opened her eyes to see her friends approaching. They both had huge grins, but it was obvious they were pretty tired.

"Shall I take my ladies home?" I said, cheesily.

As we left, Josie never let go of my arm. She leaned on me the whole way and as we waited for a cab, way to tired (and in their cases, drunk) to walk back. Not wanting to wait for one of those van sized cabs, we crammed into the back, with Josie on my lap in the middle. Surrounded by so much exquisite female flesh...and my sisters tight tushy bouncing on my lap. Lets just say that I hoped she was drunk enough not to notice the thing poking her rear.

We made it to the building, and stumbled inside. The girls all decided that they wanted to rinse off all of the sweat they had built up. My sister disappeared into her bathroom and I couldn't help but notice that Denise and Esther went into their bathroom together. I putted around the living room to give Josie some privacy, until I heard noises of pleasure coming from Esther and Denise. My erection from the cab returned. Not wanting to get caught in an awkward situation, I retreated to Josie's room.

I had just gotten undressed and ready for bed when I heard a moan from Josie's bathroom. I jumped up, to make sure she was OK. The door was cracked open a few inches so I could peak in. The sight that greeted me showed that she was more than OK. Her bathroom is one of those with a big hot tub-like bath. Currently Josie was sitting up on the edge, leaning against the tiled wall. Her head was thrown back and eyes closed. One hand fondled a very erect nipple topping her firm breast. The other was placed between her long, lithe, and widely spread legs slowly rubbing her tightly trimmed pussy.

I was surprised that I didn't faint! I was also surprised that my brain wasn't telling me to quit watching. Instead, I stood there with my dick quickly poking through the fly of my boxers. Minutes went by. Her legs would sometimes quiver when she'd rub herself just right. She continued to moan lightly. At some point, my hand found my cock and began to stroke unconsciously.

As she began to build, she slipped a finger into herself. Shortly after, she inserted another. Her movements sped up. Her moans changed to stifled cries as she pumped faster and faster. My own hand went on auto pilot and matched her. I couldn't believe this was happening. With everything that had happened tonight, and now being capped by the most erotic sight I had ever laid eyes on. The way she arched her back and swiveled her hips. The tone of her pleasure sounds went right to my aching cock. I knew that this was my sister, and it was wrong. But I couldn't help it.

She finally reached her peak, and managed to shock me even further. As her orgasm raced through her, causing her hips to buck, she cried out "Ooooooh, Briiiiiaaaan!" As she came down, my own impending release approached. She slowly opened her eyes and looked right into mine. She smiled wickedly, and I realized I had been caught, my hand immediately leaving my erection. But instead of freaking out, she just looked at me and mouthed the word 'cum'. And I did. Without even touching myself, my cock exploded, shooting my considerable load all over the door.

When the last shot fired, Josie got out of the tub and grabbed a towel. She moved toward my frozen form. Opening the door, she slowly wiped my cum from the door, tossed it towards the hamper (missing), and stumbled to the bed. Plopping down naked and face first.

At this point, blood returned to my brain and started making sense of things. I remembered that the girls were VERY drunk. Josie leaning on me at the end of the night may have been because she could barely walk. She probably wouldn't remember any of this. I gently slid into bed and she turned toward me with a warm smile. But her expression showed that she was half gone already. I laid on my back and tried to let her pass out and let myself try and ignore the fact that she was naked. She quickly went out, but not before scooting against me and laying her head on my chest. And with that, she was gone with a contented sigh.

I must have laid there for a couple of hours, not able to shut my brain off so I could sleep even though my body was exhausted. Thoughts of what I had done. What I had seen. What did it mean that she called out my name? Had she known I was there? What would she do when she woke up sober and realized she was in bed with me naked? I tried (and failed) to stop thinking about how she looked...her angelic form. In my memories she almost glowed. And I felt horrible for thinking that her soft cheek and warm breath on my bare chest was the most heavenly feeling I had even experienced.

My brain finally burned itself out and sleep enveloped me. I slept like the dead. No dreams, waking up, or anything. When I finally woke, the sun was up, and I was alone. My brain immediately worried about how my sister had responded when she woke. To prolong the confrontation I took a long shower and dressed. Cautiously emerging into the living room, I found the three roommates chatting away at the breakfast bar. They stopped when they noticed me, each grinning like a Cheshire cat. Denise and Esther were still in their pajamas, which is to say mostly naked. Josie had on a pair of shorts and a simple but form fitting t-shirt and cute little tennis shoes.

"So, the one that drinks the least takes the longest to recover." Esther teased.

"Who knew our man was such a lightweight?" Denise laughed in her cute little accent. I blushed shyly, but didn't speak. I felt like if I spoke, last night would suddenly be brought up.

Josie got up and brought me a McDonald's bag. "McGriddles. Your Favorite if I remember correctly." He smile was sweet and certainly didn't show any hint signs of being upset. "Come on. I want to take you to Central Park. You can eat on the way."

Now I was worried. Was she putting on an act till she could get me alone? If so, she was a dang good actress. I briefly thought about coming up with an excuse not to go, until I realized that I was already obediently following her out the door like a puppy dog. Denise and Esther called out to us as we left, saying goodbye.

Under the pretense of eating, I delayed any conversation. Which Josie seemed fine with. She simply took my arm in hers and enjoyed the morning air. The walk to the park was short, and soon we were enveloped by the green. It was like we were teleported out of the city. My sister took me a grassy spot in the shade far enough away from the main paths for privacy, but not so far that you can't see people going by.

"I come here often. To people watch." She mused. Her voice still sounded normal. No hint of anger.

"Yeah, I love people watching too." I responded lamely. I could only be mute for so long. Minutes passed as we watched people walk, bike, and roller blade by.

"So, you're not going to bring it up, are you?" She asked, without taking her eyes from the passers by. The way she asked was still light. No upset tones.

"Um...bring what up?" I asked, playing dumb. Maybe she just meant about whether I enjoyed the night out with the girls.

"Hmmmm...maybe the part where you peaked in on me masturbating? Or the part where I caught you beating off while you watched me? Or the part where you crawled into bed with your naked sister?" She finally turned to look at me and she had a big grin.

Suddenly, a light came on in my head. When she said 'caught'. I thought the same word when she opened her eyes after her orgasm. I had originally thought I had been caught, as in 'red handed'. Now I was thinking that maybe I had been caught, as in a trap! Now facts were sliding into place. As realization spread to my face, she laughed lightly.

"Wait a second! Why was the bathroom door cracked open in the first place? And why were you sitting on the edge and not down in the water? Did you say my name just to mess with me?"

"Oh, now I'm on trial?" She said, jokingly. She was still perfectly calm. "Well, let's see. The door was cracked because I knew that after how worked up you got my roomies, they would definitely be joining in on some activities that would make you nervous and drive you back into our bedroom. Heck, I would have joined them, if you weren't here-"

"Wait? You're gay? THAT'S why you haven't had a boyfriend in a few years?" I interrupted.

"No." She smiled. "I'm just open to enjoying life from any angle. And I haven't had a boyfriend because I have been waiting for mister right to come around."

"But let's save that conversation for later. I was answering your other questions. So, I left the door open knowing you would eventually be in our room and hoping you would get curious." My eyes widened, which caused her smile to grow. "I was on the edge of the tub because you wouldn't be able to SEE anything if was in the water. And I said your name because I was thinking of you when I got off." She finished matter-of-factly.

I was stunned. All kinds of thoughts raced through my head.

"And before you start thinking it," She chided "Everything that happened before we got home was genuine. The only reason you didn't end up in either Esther or Denise's bed is because I asked them to hold off. You pretty much, literally, charmed the pants off of all of us."

I blushed deeply, so she reached out and took my hand it hers. I felt tingles up my arm as she stroked it softly. She didn't say anything for a while, letting things sink in.

"So, uh, you wanted me to, um, watch you?" I asked lamely.

"MMmmmm, more than just watch." She purred. I felt my pulse rate double. "Last night was just testing the waters, so to speak." The back of my brain was freaking the fuck out! But the gentleness in her voice and way she held my hand reassuringly kept me calm.

"More? Like what?" I croaked.

Without hesitating, she leaned in and kissed me. Unlike my first night, it was a much fuller kiss. Those soft lips pressed mine and worked gently against me. Without needed to think it, I kissed her back, returning the same gentleness. Her lips parted and I felt her tongue slowly snake into my mouth. It found mine and we began to softly duel.

I followed her lead as our soothing, lingering kiss continued. I was having a hard time holding back. There were rivers of passion I was barely containing. But for some reason, I felt like she was too. Perhaps it was a hint of labored breathing. Perhaps the occasional more aggressive tongue movement. Either way, she was using this to answer my question, so she was in the lead.

After a blissful eternity, she broke our kiss. As she pulled back, I opened my eyes for the first time. Hers were still closed. She took a deep breath and a contented look washed across her face. She finally opened her eyes and gazed at me, glittering as they seemed to moisten. I felt as though she were holding back tears.

"Does that answer your question?" She said, her voice having a slight tremble. I nodded slowly as I took it in. The night before she had shown me her sexual side...a side she obviously wanted to share with me. Just now she had shown me her loving side. Specifically how much she loved me. Not just as a brother, but as a man.