A week after I returned home from Salt Lake City, I had v-mail from my oldest sister, Jackie, telling me she'd be in San Diego for the weekend. She would be staying downtown with her current girlfriend, Monique. Monique had a business trip and Jackie was tagging along to see me since it had been a few months. Jackie is five years older than me, 29, and has always had a thing for girls dating back to high school. She has had a couple guys in her life, but they've never lasted too long. We swapped messages and decided to meet at a rooftop bar across the street from the hotel she was staying.
Friday night arrived and I took a taxi downtown. Whenever I'm with Jackie, I end up drinking too much to drive and have just learned it's easier to cab it both ways. As expected, the bar was pretty crowded with gorgeous sunset views of the Pacific as one of the attractions. The beautiful people wanting to see and be seen was the other. I found Jackie standing at a tall table near the bar. No surprise with that location. She had two drinks already on the table, one waiting for me. She gave me a big hug and a kiss on the cheek. "Wow! A college graduate ... Congratulations Danny."
She was dressed to thrill as usual. She wore a body shaping, low-cut blouse, a form-fitting leather skirt and six-inch heels. Jackie is 5'8" and the heels make her look even more imposing. As opposed to Misty, Jackie was slighted by nature in the breast development area. So, like any modern woman, she bought them. Hers are 36D models and her long legs made her look even larger. I remember the first time I saw her after the surgery. I was 19 and couldn't take my eyes off them. She walked over, unbuttoned her blouse and let me squeeze them through her bra. I jerked off every night for two weeks thinking about them!
We had a couple rounds of drinks and caught up on life while watching the sun set into the Pacific. Jackie suggested we order some appetizers instead of dinner and then maybe go dancing. I asked where Monique was this evening. She had a work dinner but would join us before the night was over. I felt like the waitress had been flirting with me all night but I figured it was just my male ego. We played with the finger-food and by our fourth round of drinks, we were beginning to feel no pain. I could feel Jackie's body pressing closer to mine as the rooftop bar grew more crowded. Jackie leaned closer, "I heard a big secret about you, Danny-boy."
I took a big drink from my glass waiting for her next words. After last weekend, and knowing how close my sister's are to one another, I figured I'd need fortification. "Oh yeah big sister. What's that you heard?"
Jackie's left hand squeezed my inner thigh, "Misty tells me you have a big cock and know how to use it well!" Jackie laughed as the words past her lips but her hand slid further up my thigh. "Drink up, it's time for you to take me dancing!"
I told her I needed to use the john and she said she'd grab the check. As I returned to the table to get her, the waitress gave me a smile and a wave. "Barbie says she'll call you. I gave her your cell. Let's go." She grabbed my arm and we were in the lobby before I could barely wave good-bye. As luck would have it, the elevator was empty as the doors closed behind us. It was only 12 floors to the street-level, but Jackie pressed me against the back of the elevator and put her thigh between mine. She could feel my cock against her firm thigh as her lips pressed urgently to mine. When the doors opened, she broke the kiss and pulled me from the elevator. My mind was in a daze from the intensity of the kiss. I could only imagine the rest of the evening.
We half-ran across the street and into the lobby. The dance floor was on the 30th floor, the penthouse. This elevator wasn't so empty but Jackie didn't miss the opportunity. She stood in front of me and pressed her leather-clad ass against my crotch. By the time the doors opened to the 30th floor, I was fully erect from her attention. The club was crowded but we quickly found our way to the dance floor. We danced slow and fast, but regardless of the tempo, Jackie's body was all over mine. I had almost forgotten she was my sister! Forty-five minutes later she announced it was time to go. We quickly found ourselves outside room 2836. She slid the key in the slot and we were inside her room. The view was breathtaking but paled compare to the view I was about to see. I'm not even sure I had closed the door and Jackie had already pulled her blouse over her head. She was facing me with a big grin on her face. I couldn't take my eyes off her incredibly large naked breasts. They were truly magnificent to see for the first time. "You know you want to touch them," as she walked to me.
I bent my neck and took the left one in my mouth. My tongue danced on her nipple as my lips sucked and kissed her large globe. Of course, the shape and firmness were so different than Misty's, but they were just as arousing. My left hand roughly caressed her right tit. I already knew this would not be gentle. The drinking and the dancing, not to mention her knowledge of my weekend with Misty, had us both charged for sex. Misty unzipped her skirt and slithered out of her skin. It was really no surprise she wasn't wearing underwear. She roughly pushed me backwards against the door and pulled my shirt over my head. Her hands quickly unzipped my slacks and she pushed them to the ground. Kicking off my shoes, I slid free of the pants around my ankles. My erect cock was straining against my briefs. "You know you want to touch it," I managed to throw back at her.
Jackie thrust her hand inside the waistband and grabbed my cock at the base. She looked me in the eyes and mouthed the word "WOW!" as she felt it in her hand. I reached down and pushed my briefs down my legs and stepped out of them as she stroked the length of my cock with her hand. "Damn Danny! I don't think I've ever seen a cock so big. And that slut Misty deep-throated you?" I knew she said it endearingly.
I smiled at her, "That's one of three holes I buried it!" I pulled her face to mine and crushed my lips to Jackie's. My tongue slid inside and we kissed with lust. Both us fighting for control of the moment.
I turned us around, Jackie's back was now pressed against the door. She wrapped her thighs around my hips and linked her ankles behind me. My cock pressed against her dripping pussy and I pushed it inside her. She gasped as my thick cock opened her pussy wide. I don't know what toys she uses but I guessed she hadn't been fucked by anything as big as my cock in a long time. I quickly began to thrust my hips forward and back quickly burying my ten inches in her moist pussy. I was fucking like a madman and I could feel her body urging me deeper. Her breasts bored holes into my chest. Her nails digging into my back. It was fast and it was furious. When I felt her body quiver with orgasm, I shot my load deep into her sex. I continued to hump as she pulled more and more cum from my body. Finally, both of us covered in sweat and panting like dogs, she unhooked her ankles and I gently lowered her to her feet. Her legs were shaky but she could stand on her own. "What a Fuck!" was all she could say as she tried to catch her breath. She moved past me towards the refrigerator. Even in the low light, I could see our cum running down her inner thigh.
"Rum and Coke?" she asked with a smile. Jackie pulled a six pack of Coke out of the refrigerator. She had a large bottle of Rum on the counter beside it. She poured us two glasses, neither with much Coke at all. "How do you not have a girlfriend!" It wasn't a question but a statement. She held the glass in her right and my semi-erect cock in her right. Jackie led me to the balcony and the cool night air felt great on my hot skin. It really wasn't a concern that her heels were the only piece of clothing between us. "You will go down on me, won't you little brother?"
I grabbed a large throw-pillow from the bed and tossed it on the deck in front of the chair. Jackie, seemingly a bit surprised that she couldn't ruffle my feathers, fell backwards into the deck chair. She lifted her legs against the patio railing spreading her legs wide for me. Her dark pubes were neatly trimmed in the shape of heart. I figured Monique had performed the trimming.
I took a long drink from the Rum and Coke and then pushed my cold, wet tongue against her puffy lips. Jackie gasped at the cold sensation against her hot skin. My sense of taste was conflicted with the sweetness from the drink and the tanginess from our merged cum oozing from her sex. I buried my face in her wanting sex with my tongue sliding in and out of her. I took my left index finger and pressed it against the rim of her ass. I could feel her clenching then relax for me. Our juices had run between her leg and I swirled them around the rim before pushing into the first knuckle. My tongue was sliding side-to-side against her clit. It was not as large as Misty's but it seemed more sensitive to my touch. Two fingers of my right hand began a smooth fucking motion in sync with the index finger in her ass. I had my big sister on the edge of the seat with all my attentions to her clit and pussy and asshole. I pulled my fingers from her pussy and took a quick drink sucking a small ice cube into my mouth. Before she lost focus, I pressed my cold lips to her pussy and pushed the cube inside of her. She lurched forward and yelped as she felt the cold ice quickly melt in her sex. With my tongue hard against her clit, her body quickly shook and rocked as I brought her to her second orgasm in 30 minutes. "Oh Danny, Oh Danny, so fucking good ...."
