Date With Little Sister

*** Appreciate the awesome editing by Akiann to improve the readability of this story ***

*** All characters are 18 or older at the time of this story ***

I was devastated, but I shouldn't have been when I caught Natali who I dated for over two years with her boss - with his pants down below his knees. I froze, blinked, and looked again to be certain that the head bob at his cock belonged to Nat, not anyone else. Buttons on her blouse were opened, her bra was pushed down below her breasts and the way she knelt in front of him had her skirt risen all the way up, exposing her thighs. I clenched my teeth in utter disgust, realizing the girl that I dated, hoping to marry soon, was sucking her boss's cock, right in his office. I turned and walked away.

That day, Nat had told me that she had to complete an important presentation for her boss and she would be few hours late from work. Having work of my own that I wanted to complete, I promised to wait for her till she was done for the day. It just so happened that I completed my work by 6 pm and decided to go up to Nat's floor to wait until she was done.

Without giving any thoughts, I came to the conclusion that our relationship must end that very same day. However, I went back down to my floor and waited in my office for Nat in order to tell her what I saw and end the relationship gracefully as possible.

When Nat showed up, it was almost 7 pm. I pondered how many loads of her boss's cum she sucked up or has been deposited in her slutty pussy. When I told her that I wanted to end the relationship with her due to what I saw, Nat first blushed and then her blush quickly turned to anger.

"Look Brandon! I wasn't virgin when you met me..." She fumed. "If you can't deal with it, go rob a baby girl from a cradle." She yelled and walked away. I sighed in relief - I hadn't gone too far with her and tied the knot.

First, folks at the office became suspicious that something may have gone wrong between me and Nat. Few asked questions and I know I told part of the story to only one or two good friends, but soon the entire floor knew that I had dumped Nat, but only a few knew why.

The only person I told the entire story to was my sister Alicia.

It wasn't as if I was looking to vent or wanting sympathy. The Saturday following the breakup with Nat, I had nothing to do. I wasn't in the mood to go to a single bar or hangout with friends. Since Ali now goes to the university about 30 miles from the city, I decided to take a drive and have lunch with her. I also knew that I would run into few acquaintances there and perhaps even get to meet few fresh faces, just like the old days. Since Ali didn't have any plans that afternoon, we had lunch as planned, then strolled around the U and I finally wound up taking her out to dinner as well. When the topic of Nat came, I was already under the influence of few drinks and words just slipped out.

"I can't next weekend. I have to go to Jack's wedding."

"Ahh...yes, I remember you telling me that. Who are you going with, not Nat I hope."

"Are you mad? No, no...I don't have anyone to take...I guess I'll go alone."

"I'd go if you'd asked." Ali said quickly and added, "Maybe not, it'll be too expensive to you to take me..." She made a pouty face even before I answered her.

"No, not really. Would you go with me to Jack's wedding? I would love to take you."

"Right?" Ali smiled, "besides if you take someone, you can show off to Nat, right?'

"Not really, but yes. If that makes sense. Would you come?"

"I'd love to...besides I want to see that slut...Nat and make her envious...yes, but I don't have a dress that's nice enough for a wedding here and no money to do other girly stuff, if you know what I mean?" She smiled showing her interest, yet I saw some sadness in her eyes indicative of her inability to go without proper attire.

"What if you buy a new dress? On me...any dress you like."

"I can't tax you for helping you. Let me think."

I wanted Ali to come with me to the wedding, of course for selfish reasons. Although I had no issues paying for a decent dress, I did not want my little sister to think that I badly needed her to show off Nat under the circumstances. That would be bad...

I spent few minutes trying to persuade her to take the money, she hesitated for a while and then finally agreed to buy whatever she absolutely needed using the money and she said "I'll keep it to under couple of hundred dollars and I'll do my own makeup." I left after agreeing to pick her up following Saturday midday.

"Pick me up by 1 pm" She requested.

I did just that on Saturday. Ali talked all the way to my place about the dress that she found on sale, how lucky she was to be able to borrow a pair of shoes from a friend that matched the dress, etc. I tried to hear her, but my mind was pre-occupied with the wedding reception at all times, debating if I should even go, knowing that Nat would definitely be there and the atmosphere could be awkward. True, Nat works at the same office complex, but because we are in different divisions and on different floors, we never ran into each other often.

"Do you really want to go with me tonight?" I finally asked interrupting string of words that escaped Ali's mouth.

"Hey, relax... Yes, you are going tonight and I am going with you. Let's just have some fun ok." she smiled, "let's get over this Nat phobia once and for all today, ok."

"Ok..." I hissed suspecting that Ali had the ability to read my mind.

"What a bitch!" Ali said, squeezing my hand. "You deserve someone pure, honest and educated, not a slut like that bitch." Ali fumed and I noticed her eyes were watery as if she was ready to cry, but she smiled instead.

When I dropped Ali at her student housing, she said, "You can come back next weekend if you don't have other plans, we can hang out here or go somewhere and do something together like the old days."

I showered first. Ali rushed in as I walked off saying, "I need bit more time in here than you," and knowing the female nature, I fully expected that. A good 45 minutes later, Ali ran into my bedroom while I was in the living area, apologizing for the delay.

"All I have to do is now to get dressed. Won't be too long."

"You don't have to rush, but remember that we have a long drive." I smirked reminding her without bothering to turn my head. Another 30 minutes later, Ali appeared from my bedroom, where she had been dressing. What an appearance... I bit my lip ogling the gorgeous woman who stood before my eyes.

"You don't have to rush, but remember that we have a long drive." I smirked reminding her without bothering to turn my head. Another 30 minutes later, Ali appeared from my bedroom, where she had been dressing. What an appearance... I bit my lip ogling the gorgeous woman who stood before my eyes.

Black knee length dress, lace covering her chest to neck and pleated just below her hip. Back was completely covered with black sheer material, but zipped to back of her neck. She wore no pantyhose's making her ivory legs seem as if they gleamed due to the contrast. As she walked towards me, slightly parting front of her dress spread a little, revealing the lower part of her creamy thighs were flawless. Those thighs that I used to adore years back. Very elegant black shoes with a small heel made her hips sway as she walked, something that I hadn't seen in her before.

"WOW Ali, you look stunning!" I managed to say, while still sipping more of her good looks through my eyes. I have never seen her wear any make up, nor a formal dresses ever since her junior high school days, but regardless of how she dressed, she always looked so pure and innocent. Growing up, she had had bit of tom boyishness in her. She loved to get dirty and doesn't mind playing sports with the guys. She took best of both worlds those days I guess sometimes acting like a boy, climbing trees, playing rough and other times playing house or playing with dolls. But the girl who stood there was none of them. A completely different creature who looked so seductive, sexy and innocent at the same time.

I stared at my gorgeous sister as my "date" took my hand and led her to my car. As we hit the road, it immediately struck me that not only her attire and looks changed, her behavior also changed drastically with her new look. She deliberately chose words to speak and spoke in a very sexy tone. When she turned and placed her lips on my right check, giggled and wiped lipsticks off my checks, I felt like I was on a date with a new girl, not my own sister.

"You look stunningly beautiful Ali!" I complemented her.

"Umm... I am not Ali or sis for you tonight. I am Alicia, your girlfriend." She chuckled to remind me.

We arrived at the reception, went inside hand in hand as lovers, and headed to the patio where hors d'oeuvres and drinks were severed prior to dinner.

"What would you like Ali? Do you care for a soda or something?" I asked and Ali giggled saying, "Alicia prefers to chase her tequila shots with Sprite, but she'll be a lady tonight... a tequila sunrise would be wonderful."

I had to laugh remembering that Ali was no longer a little girl, plus my stupid for calling her Ali.

"Yes, indeed... tequila sunrise for my lady."

We sipped our drinks and mingled with folks that I knew from the office. The very first time that I had to introduce Ali to a friend, I had to pause and think quickly if I had told anyone about my sister Alicia or if anyone has seen her before. Of course not. I had always referred to her as my sister going to the U, but I felt strange whenever I or someone else referred to Ali as Brandon's date or as Brandon's girlfriend. However, alcohol was able to settle my nerves and Ali played along just fine, without giving the slightest impression that she was even related to me.

When I introduced Ali to Nat, her eyes widened in surprise.

"Nice to meet you, Brandon has said quite bit about you." Ali said offering her hand to Nat.

"Nothing bad I hope..." Nat said shaking Ali's hand and added "How long have you two known each other?"

"Well, Brandon gave you a mixed review and for us, we have been seeing each other on and off for a year or so, right Brandon?" Ali said with a straight face sending Nat back to wherever she came from.

A band played throughout dinner, and then after dinner the lights were dimmed for welcome speeches followed by bride and groom dances etc. Then the band increased its volume for those that wanted to dance. It wasn't me who asked Ali for a dance, instead she looked at me and made a gesture prompting me to ask her to the floor and she eagerly accepted. We danced for a while seeing that Ali really enjoyed making her dance moves and showcasing her figure to many who looked

Everyone was having a good time and apparently Trent (Jack's asshole friend) had told some of the others that he desired Ali. Soon Ali became the center of attention for most of the single men at the party. She spent most of her time on the dance floor with me, but didn't refuse when other's asked her for a dance.

I was at the bar getting Ali drink when Trent came up to me and asked me if she was my girlfriend or just a friend. I immediately knew what Trent was after and said that she was my girlfriend. I got temporarily side tracked and I got back to the table just in time to see Trent escort Ali out to the dance floor. When she got back to the table I laughingly told her that she could probably expect to be asked for a date before the night was over. She chuckled and said, "I know... Trent kind of touched on the topic, but I am all yours. Remember?" She gave an impish wink and a smiled.

We danced some more and mixed with others as well. I did noticed Nat paying attention to Ali and me, but I acted as if she wasn't even there. Conversely, the more I drank, the more I danced. At some point I realized that Ali was getting touchy-feely with me, and also pulling me tighter and tighter against her during a slow dance.

"Let's make her jealous." she whispered pushing up her hips to my groin. I wasn't hard or anything, but I knew my cock had lengthened enough to her to feel me. I knew it was wrong to even have a little stir under my pants when I was dancing with my little sister, but the wine and the festivity were working their magic on me. But I had once lewdly held her against my body, years back.

Before I knew it, the reception was coming to an end. Ali and I were one of the few couples left on the dance floor, and I was pretty well toasted. As we danced to the last song, slow song, I felt my sister's warm breath on my neck, her breasts crowding my chest and I had no doubts in my mind that she felt my semi hard cock on her belly.

We walked hand in hand to the parking garage, just like lovers - Ali swirling her tender body all over me. Once we found the vehicle, she smiled, smiled mischievously and then quickly turned standing behind me. Within seconds, her hands fumbled around my outer thighs before each hand found their way into my pant pockets.

"I am driving... I think you are close to the limit and no DUI's on our first date." she chuckled letting her hands hunt for car keys. Even after she located keys and they were in her hand, she pushed hands inwards towards my cock and removed her hands ever slow slowly. I gasped when her hand rubbed my cock, but I discounted it as an accident.

"Are you going to drive all the way to the dorm?"

"No silly, I am staying at your place. There are cops all over around the U on Saturday nights. You can drop me off tomorrow." She giggled, leaned and this time most unexpectedly, placed her lips on mine. I was stunned and memorized how delicate and seductive my sister was, but she was my date for the night and behaved as such.

"Sorry, I shouldn't have kissed you like that on our first date. I just felt slutty for a moment, but I don't normally do that." Ali smirked as I got inside the car. But not before I murmured "That's a blessing for any guy, but I am with my sister."

"No, I am your date tonight. It's still Saturday right?" She chuckled again as we hit the road. I can't say that I wasn't turned on, especially the way that Ali played on, but feared for something that I couldn't pinpoint.

"I am ready for a nightcap. You too?" Ali asked as we entered my apartment. Then without waiting for an answer, she added, "I can't wait to get this dress and make-up off me. I am going to take a quick shower, you open a good bottle of wine." She disappeared into my bedroom. I looked through the wine cabinet, found a good bottle of chardonnay. While I was opening the bottle, Ali walked to the bathroom. She briefly stopped to smile.

"Your turn, if you want to shower." Ali said when she came out of the bathroom and as I looked up, I just couldn't believe my eyes how quickly she changed her appearance. She had gone from wearing a sexy dress to one of my boxer shorts and a T-Shirt. V-neck T-shirts that I normally wore was seemingly too large for her and the opening at the neck ended just around her perfectly round breasts and her nipples pushed through the thin material as they were ready to getaway. Well, the shorts were naturally too large for her waist and she held them in place with her hand. I was already tortured by my sister all evening and seeing her dressed the way she did, I instantly got a hard-on.

"What?" Ali chuckled.

"Don't let go of those pants." I laughed, "The wine is poured and I am going to shower." Although I typically walk out of the shower naked and sleep naked, I got into a pair of boxer shorts and sleeveless shirt since I don't even own a piece of pajamas. The shower rejuvenated me as I joined Ali for a glass of wine, which became two and the third before Ali thought that she had enough for the night.

"You can have my bed. I'll sleep on the couch." I offered walking to the bedroom to grab a blanket and a pillow.

"Your bed is big enough for both of us, isn't it?" Ali said somewhat disappointed.

"Hey, however slutty you feel, you shouldn't sleep with a guy on your first date." I joked.

"Umm... No. This is not the first time. I slept with you many times when we were younger. I used to come to your room whenever there was a thunderstorm, remember?"

I just couldn't help but blush. How can I forget...? As kids, we had slept together many time. But several times Ali came to my bed room during thunderstorms after she had turned eighteen. I remember holding her and comforting her till she fell asleep while feeling her soft skin against mine. But I have been trying to forget how I pressed my cock against her cloth clad ass. First few times, I did that until I was ready to explode, then turned to other side and relieved myself. Later I became daring enough to raise her gown to rub my cock on her chubby ass-cheeks. Most times, I turned the other way and jacked off to cum, but I remember at least twice I shot my cum between her thighs or ass-cheeks when I had past the point of no return.

I hid my tension and embarrassment briefly and said "Yes, but we were younger then."

"I felt so secure then..." she said looking into my eyes, begging to sleep with her "Besides, it is still Saturday and tonight, I am your date and girlfriend, not your sister Ali. C'mon..." She said, taking me by hand and walking to the bedroom.

"That's not enough reasons to sleep together Ali. Give me a better reason." I said grimly.

"Another reason...? Ali stopped at the bed and asked, "How about your boner? What are we going to do about it after our first date?"

"What boner?" I panicked, looked down and noticed my bulge that was noticeable, although I wasn't fully erect.

"This..." Ali purred gently placing her right hand over my cloth covered cock and then leaped up and kissed my lips gently. I was utterly shocked at how my sister even had the courage to do such thing, but before I had a chance to speak, her hand glided inside my shorts, pulling at the elastic band. Her hand shuffled inside my shorts fleetingly until she found and grasped my manhood. It was as if an electric shock went through my body. I knew it was wrong, very wrong, but the wrongness of my sister touching my most private body part made it even more exciting and incredibly thrilling.

But, Ali held my cock in her soft hand as if she had my most prized possession. "This is cool, I mean nice and stiff." She whispered. "I love the way it pulsates and responds to my touch." Then added, "Hmm... If this is not a boner, what is?" She giggled pressing her lips on to mine again.

"No Ali, I don't do taboo things... Believe me, I am not into that sort of stuff." I said, but perhaps not strongly enough to convince her.

"You mean you don't do that stuff anymore, right?" Her eyes sparkled as she smiled. "Besides, who said we are going to break any taboos?" She chuckled, "Let's cuddle up and be comfortable. We can feel each other up like you used to, don't you think that will be fun?"

"Look Ali..."

"Shut up and come to bed. This feels wonderful in my hand." She started stroking me up and down, slowly but firmly. I closed my eyes. If it felt wonderful for my sister, it felt positively phenomenal for me. I let the sensation, of my sister caressing my cock engulf me. Her lips reached my jaw, outlining the lines of my ear to my collarbone. They were as warm against my skin as they reminded me of soft, little rose petals, but warm and moist. I couldn't stop my heart from pounding in my chest. My blood flowed rapidly in my cheeks, making my face as red as ever. However lewd it was, it was delicious. I lifted my hands out from under her, and pulled them up her shoulders as Ali put her hands down at my waist while pulling me closer to her. I was so hard I couldn't stand it, but who should she be for tonight? My lover or my sister?