Nina's Sister

I love my single life, but sometimes I get tired of going home after work and making my own dinner. Those days, I go out and enjoy a meal at one of my favorite restaurants. This story began on one such evening.

This time I decided to eat at Rosa's, my favorite Italian Cucina. I usually have lasagna, a garden salad with Italian dressing (hold the croutons), and a half-carafe of Chianti. My server, Nina, knows what I always like and put the order in as I sat down. She was married now, but a couple of years earlier we'd shared many sexual adventures. There might even be a story about Nina on this forum. When she brought my dinner, we took a few moments to catch up and share a couple of laughs. It was turning into a pleasurable dinner in familiar surroundings, and I was relaxing after a stressful day.

About halfway through my steaming plate of lasagna, Nina came over and asked if I'd mind sharing my table with another customer. At first, I thought it was a strange request. But I looked around and noticed that the small restaurant was filled to capacity, except for the other chair at my table. Nina smiled at me and said, "It's my little sister, just back from England."

Her sister had been out of the country attending college when Nina and I were dating, and we'd never met. I said, "Sure, I'd love to have dinner with your sister." She motioned to the beautiful woman with long chestnut-colored hair girl standing just inside the dining room doorway. I did a double-take. She could've been Nina's twin. Her smile lit up the room as she strolled over and sat across from me. She met my gaze with the most enchanting brown eyes I'd ever seen. I felt a familiar tingle below my belt.

"Hi. I'm Nina's sister, Nichole. Nina tells me you're her friend, Jake. I've heard so much about you. It's nice that we finally meet," she said.

"Good things, I hope. The pleasure is all mine. Nina told me she had a sister who was studying abroad, but she didn't mention that you look like twins," I replied. "She said you're her little sister, but I guess that's only a measure of age."

"True. Nina takes after our dad, but I seem to have gotten more of our mom's height." I remembered that Nina's mother was a six-foot-tall blonde beauty and that Gino, the girls' dad, was about five-foot-two with thick-heeled shoes.

"May I buy you dinner, Nichole?" I blurted and was immediately embarrassed.

A sexy little laugh bubbled up from somewhere deep inside the gorgeous brunette. "That's really nice Jake, but since my family owns the place I doubt they'll charge me. But, I appreciate the offer."

Nichole's meal soon arrived, and we enjoyed a lively conversation as we ate. After a second half-carafe of Chianti and many laughs it was time to give our table to a middle-aged couple who'd been patiently waiting at the bar.

I asked Nichole if she'd like to go to a nearby bar for another drink, but she said she was going to stay and see if she could help out in the restaurant. I told her how nice it was to have finally met, and how much I enjoyed our conversation.

I was nearly to the door when I felt a gentle hand on my arm. "Jake," Nichole said. "I'd love to get to know you better if you'd like. Can we postpone that drink until sometime soon?"

I was a bit stunned that she was asking me out, knowing that I'd dated her sister. In a few seconds, I recovered enough to respond, "I'd love to. How about this weekend?" Was I pushing too hard?

"Great!" She said and handed me a small piece of paper she'd already written her cell number written on. "Call me tomorrow?"

The weekend was only three days away, so I made it a priority to call Nichole from work the next afternoon. She and Nina were shopping, but she told me that we were good for Saturday night. I said I'd pick her up at seven for dinner at an upscale restaurant in a nearby town. I sheepishly admitted I'd already made an eight o'clock reservation there.

The next two days seemed like a week, but Saturday eventually arrived as did I at Nichole's door. The forty-five-minute drive to the restaurant flew by as we chatted and even sang along to a couple of songs on an oldies radio station. We got to the nautical-themed lakeside restaurant at eight and were seated right away.

Dinner was excellent, and by the time we finished our dessert it was after ten o'clock and we seemed more like old friends than a couple on their first date. I guess we knew enough about each other already, to facilitate a natural feeling of familiarity.

On the drive home, I asked Nichole to come to my house for drinks and to continue the great evening we were sharing. She said she wanted the evening to last too and was looking forward to seeing my place.

At my house, I asked Nichole if she'd like some wine. She said, "Sure, do you have any Cabernet?" I did and poured two full glasses of my favorite Finger Lakes vintage. We kicked our shoes off and sat on my loveseat with our bodies touching.

By the time the bottle was empty, Nichole's head was lying on my shoulder. I stroked her long chestnut tresses and she turned her face up for a long, deep kiss. As our kiss lingered, I felt her hand begin to rub my already stiff cock through my pants. It jumped for joy and grew even harder.

"It feels like someone's glad to see me," Nichole murmured.

"He's been happy to see you all night, Nichole."

"Then maybe I should reward him for his patience," she said unzipping my fly.

She looked up at me with wide eyes and I knew I had permission to go where we both apparently wanted to go. Looking into my eyes, she deftly unbuttoned my pants and pulled my cock out. I groaned with the pleasure of her warm, soft hand gripping it. It pulsed, and she gave it a little squeeze. "Would you like to loosen my blouse up?" she murmured. I unbuttoned it and slipped it off her shoulders. She removed the garment and dropped it on the floor. During dinner, I noticed that she wasn't wearing a bra. As we talked and laughed, I'd seen her nipples dancing and occasionally pointing at me through the thin fabric and wondered what pleasures were hidden from view.

Now, before my eyes, were the firmest large breasts I'd ever seen. Nichole was twenty-three and her breasts didn't have a hint of sag. They had to have been double "D" cups or bigger, and I had never seen a pair that big that didn't sag at least a little. Her prominent nipples surrounded by milk chocolate colored areolas took my breath away. "You like what you see, Jake?" she smiled.

"My god, Nichole. I've never seen breasts as perfect."

"You're just being nice," she whispered.

"No. Yours are absolutely the most beautiful tits I've ever seen," I croaked.

"I'm glad you like them." She worked my cock, gently squeezing below the knob as her fingers reached the top of each stroke. I groaned and kissed her deeply, playing with the hard nipple of her left breast as she slowly carressed my pecker. "Shall we take a quick shower?" she whispered.

Now there was no question of where the evening was headed. I took her hand and led her to the bathroom. In the steamy spray, after we'd soaped and rinsed each other, Nichole slowly sank to her knees and took the head of my cock between her soft, full lips. My knees buckled slightly with the amazing sensations of the heat of her mouth and the softness of her tongue circling my glans while she gently stroked the length of my cock.

Nichole took her time and gave my cock a nice long sucking, cupping my balls in one hand and gripping my butt with the other. her mouth was the wettest my cock had ever been in. Saliva dripped from her lips as she gently licked and sucked me. After several minutes, Nichole licked her lips, stood up, and said, "I'm glad you didn't cum. I was really enjoying having your cock in my mouth and didn't want it to end."

"That was wonderful. My God, Nichole, your mouth and hands are magical." I whispered. "By the way, If I start to cum when you're sucking my cock, you can just keep sucking if you want. Looking at your face with my cock in your mouth will keep it hard. You're the sexiest woman I've ever seen."

"I felt your knees start to buckle, Jake," she whispered. "I take that as a compliment."

I turned the water off and we took our time drying each other. Nichole wanted to dry her hair before we hit the bedroom, so I dug the dryer out for her and went to turn down the bed.

A few minutes later, a goddess of nearly unnatural proportions walked into the bedroom, and once again I had to remind myself to breathe. Nichole was nearly six feet tall with unbelievably firm huge breasts and a small waist. Below her waist, her hips flared to a perfectly aesthetic dimension. Her smooth, curving hips supported a round and firm butt that any man would die to touch, lick, and kiss. That's exactly what I had in mind, as I pulled her onto my king-sized mattress.

We kissed, stroked, sucked, licked, and cuddled passionately for a long time, each savoring the first exploration of a new lover's body. Nichole sucked me differently this time. She cupped my balls in one hand and stroked my shaft with the other while locking her lips tightly around the base of my corona. In a couple of minutes, my balls erupted with powerful spurts of cum splashing against the back of her throat. With each pulsation of my cock, she swallowed until I was completely drained.

Nichole licked her lips and lay down beside me head to toe. She wrapped her lips around my cock again and we savored each other's tasty places. Nichole's carefully trimmed "landing strip" was soft and just long enough to not feel stiff against my face, while her engorged purple-hued labia were fragrant with the faint odor of sexual excitement. As savored her pussy, she used both hands and her mouth on my cock, occasionally sucking first one ball and then the other into her mouth. There was no urgency, no feeling that we had to hurry to climax, or any need to be anywhere but right there doing exactly that.

I was caught up in the perfection of Nichole's delicious pussy and slowly licked the length of her slit, and stroked her clit with my tongue and a gentle finger. I was slowly licking from her clit to her little pink rosebud, each time circling both with my tongue. After a few minutes of gentle licking and sucking, I heard Nichole moan deep in her throat. Then, as I slipped my tongue into her butthole and began rubbing her clit, she let my cock slide all the way into her throat and began bobbing up and down on it faster and faster. Her orgasm nearly threw us off the bed. She writhed and pumped furiously while continuing to deep-throat my cock, until she exploded in an orgasm that was almost violent. She bucked and moaned around my cock, and as soon as she relaxed a little I unleashed another load of cum into her throat. Before tonight I hadn't cum in several days, and I emptied a surprisingly huge load into her throat. She kept taking my cock all the way to my balls until I was dry and slowly removed it from her mouth. Then, she proceeded to lick and suck it until every trace of my cum was in her belly.

We were drenched in sweat and held each other tightly as our hearts and breaths returned to normal. Now, lying on our sides still, head to toe, my cock had become trapped between Nichole's breasts, buried in them like a hot dog in an oversized bun. She realized I was still hard and bent to give the head a wet kiss.

"Lucky me," Nichole murmured. "You're still hard and I need to feel it inside me."

"That's a great idea," I said and turned around face to face with this sexual goddess. I stayed on my back and she rolled on top of me. Her pussy was soaking wet and when she guided my stiff cock into her tight opening she easily slid right down to my balls. As her firm cheeks settled on my thighs she began by rotating her ass in tiny circles. After a couple of minutes of wiggling around on my cock with her eyes closed, Nichole slowly began to rock forward and back, rising off my cock until only the head was in her, then slamming down all the way. I wanted to close my eyes and just enjoy what she was doing, but I couldn't. I kept my eyes glued to those fantastic tits as they slowly bobbed to the rhythm of her rocking.

I lost track of time as Nichole fucked me, but at some point she said, "Jake, I want to ride you reverse cowgirl. I've noticed how much attention you've been paying to my ass." She remained on my cock and spun around so I had a perfect view of her amazing ass and see my cock slipping in and out of her body. Then I saw her tiny pink rosebud winking at me and I almost lost it.

Nichole must've noticed that I was holding my breath, or that I was tensing up. She turned her head toward me and asked, "Is seeing by butthole too much for you to take? Want me to turn back around?" The smile on her face and her tiny laugh told me that I was being teased.

"I nearly came just then, but this is such a beautiful view that I don't want you to ever stop."

"Oh, I'll stop in due time, Jake," she chuckled as she kept her rhythm. My cock looked red from all the exercise it was getting.

"No worries, Nicky," I replied. "I'm in for the long haul." We both burst into laughter and she began to slam down on my cock harder and faster.

Suddenly, The gorgeous girl fucking me so beautifully rose off of cock. She deftly reached between her thighs and placed my cock against her tight pink butthole. Missing only a few beats, she slowly let my stiff pecker slide into her ass all the way to my balls. Her butt was as tight as a glove but as smooth and soft as a satin pillow. The heat inside her ass felt like a fire burning my cock in a purely heavenly way. I found myself unexpectedly enjoying one of the most amazing anal experiences of my life.

I admit that I was stunned. The subject of anal sex hadn't come up or been suggested by either of us. I had no idea how Nicky felt about it or had ever even tried it. Yet here I am buried to the hilt in the roundest, firmest, tightest ass I'd ever had the pleasure of fucking.

Nichole sat still for a second or so, then began to slowly rise up and down an inch or two at a time. She moved like that for another couple of minutes, then began to take longer strokes until she was coming about three-quarters of the way off my cock with each stroke and beginning to moan softly.

Soon, she was pumping on my cock like a girl obsessed. She was moaning, squeaking, and even growling softly deep in her throat. I'd never experienced a reaction like that and I was having the most exciting anal sex of my life.

Then, Nicky turned her face halfway toward me as she fucked me and said, "Cum in my ass. Cum in my ass. Cum in my ass, Jake! I want to feel you cum in my ass!"

With that request, I began meeting her thrusts and pumping my cock deeply in and out of her tight little ass as fast as I could. In seconds my trigger was pulled and I began firing streams of thick cum into Nicky's perfect butt. When she felt my streams of cum gushing into her bowels, she began to scream and yell, "I'm cumming, Jake! I'm cumming! I can feel your hot cum in my ass and I'm cumming with you!"

Our thrusts subsided, but Nichole stayed impaled on my stiff eight inches. Her shoulders slumped forward and she placed her hands on my knees. My cock slowly shrank and slipped out of her ass. As her little hole closed up I saw a stream of creamy white jizz run out of the opening and down across her pussy. It was incredibly sexy to see, and I closed my eyes to trap the vision in my memory.

Nicky slid off my hips and cuddled up beside me with her head on my shoulder. "So, that's what anal sex is like," she said with a smile.

"That was your first time?" I asked.

"It sure was."

"You mean no guy you've dated ever asked you to do it?"

"Sure. A couple of guys have wanted to have my ass, but I said no."

Then I got both the biggest shock and the best compliment of my life.

"Back when you were dating my sister, she told me that you introduced her to anal sex. She said she loved it with you. She told me it was exciting and different, but that she could cum from it just like getting fucked in her pussy. I wasn't sure I believed her, but I couldn't stop thinking about it. At some point, I made up my mind to try it someday when the time was right."

"So what made today the right time?"

"You, Jake. I couldn't believe my good fortune when you accepted my date invitation. But I knew right then that if we ended up in bed, I was going to try to get you inside my butt."

"You are amazing, Nichole," I said. "I couldn't believe it when you suggested a date, and I didn't in my wildest dreams think this would ever happen."

"Well it did, and I'm glad that you let me sit on your cock. I was hoping you would so I lubed things up when I got done drying my hair. I hope you don't mind that I used your KY jelly."

"Mind! You just gave me the anal experience of my life. I warn you, though. I find your ass so sexy that I'm going to spend hours eating it if you'll let me," I said.

Nichole smiled sleepily and whispered, "I loved your tongue in my butt when we sixty-nined. I can't wait for you to make love to me there again. Now, let's get some sleep and see what happens in the morning."