Helping My Little Sister

This is a work of fiction; any resemblance to real people, living or dead, or to actual events is purely coincidental. All characters involved in any sexual activity are over the age of 18. I hope you enjoy this story. Constructive criticism is always welcome.

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It was Saturday morning ... all right, almost noon, but that's not the point. My terminally perky younger sister was moping around the house like someone had killed her pet. I tried to get her to talk about it but she just blew me off, but she continued to just be miserable around the house. Usually, she would be out playing tennis, or going hiking, or hanging out with her friends ... but she was just being miserable around the house.

By around 4 PM I had drunk some coffee and taken a shower, and she was still just moping about. I went to her bedroom door and knocked. "What?" she asked so eloquently

"Can I come in? I want to talk with you."

"What do you want to talk about?"

"Do we have to do this through the door?" I asked.

"OK, come on in," she finally said after a short pause.

When I was seated on the foot of her bed, (she was sitting up against the pillows) I asked, "What is wrong? I know that SOMETHING is wrong, because THIS is not the way my 'little Lisa' acts!" (Little Lisa had been my pet name for her for as long as either of us could remember. I was two years older than Lisa, and had always been physically much larger than she was.)

"It's personal..." she mumbled.

"Too personal for your big brother?"

"Sorta..."

"Have you talked to your friends? What about Janice?"

"No, can't."

"Jaymie?"

"Can't."

"Leslie?"

"No way!"

"Well, you need to talk to someone and get this straightened out. This is not like you!"

"You'd laugh."

"Try me, I can be a sympathetic person sometimes, you know." I said, slightly indignant.

"Tommy, says I'm lousy at sex ... and we haven't even had sex!"

I gaped! Lisa was the hottest little package of femininity I had ever seen. She had bloomed late, but she had blossomed into every guy's dream with at least C-cup tits, a firm stomach and legs, and a perfect little round ass! While she didn't flaunt her feminine charms, she didn't go overboard to cover them up either, so every guy who saw her looked twice and wished he could be at her side.

I blurted out before even thinking, "You are the sexiest girl I have ever seen! How could he say that?"

"He says I'm all show and no go. That I have no sex drive and that I'm a cold turkey!"

And you can't talk to your female friends about this because ...?"

"Well, they would laugh at me! They all have so much more experience than me. Janice has been 'doing it' with the pool guy all year, and Jaymie is doing it with one of her dad's friends, ... and Leslie has this internship for the summer and she is doing it with her lady boss!" I shook my head.

She continued, "You know that I developed late. While all the other girls were having their first dates and experimenting with kissing and stuff, I was a flat chested nerd stuck at home. I didn't mind, but I didn't learn all of that stuff like they did, and now I feel like I've been thrown into the deep end of the pool without any swimming lessons! What if I'm frigid or something?"

"I sincerely doubt that you are frigid." Then I added, "Come here. Of course, you can talk to me about this stuff and I won't laugh. I'll do what I can to help, but remember, I'm a guy, with a guy's perspective. I may not always see things the same way a woman would."

"You'll help me? Really???"

"I'm your brother, of course I'll help you. But I'm also your brother, so some of this might seem a little weird. We have always been close, and I don't want anything to interfere with the bond that we have."

"You're the BEST BROTHER any girl could have!" she said as she threw her arms around my neck and kissed me on the cheek.

After a moment I asked, "So tell me about a typical date with Tommy."

"We go to a show, usually an action shoot-em-up thing. Then we drive back here and park in the driveway. We kiss a little, then he grabs my boobs. He sometimes squeezes really hard and it hurts. After a few minutes of this he will ask, "Do you want to do something?" and when I say "Not really," he usually says, "I guess I'll be heading home." Then last night he said that maybe we should break up. When I asked why, he said, "You don't like sex, and you're really bad at it!" Then he left.

I almost couldn't comprehend what she had just said! "YOU NEED A NEW BOYFRIEND!!" I blurted out. Then I added, "From what you have said, you probably do need a little help getting up to speed on dating activities, but that guy is an absolute jerk! He will never find a woman who will willingly engage in sexual activity with his approach."

"What am I supposed to do?" She nearly wailed.

"I would start by dumping that jerk as fast as possible. Then I would find a really nice guy and ask him to help you learn about kissing, and foreplay, and sex. There must be a thousand guys who would jump at a chance to be with you!"

"I think that you're right about dumping Tommy. He is a jerk, and he really only seemed to care about what he wanted."

"Good," I agreed.

"But, while there might be several nice guys who would like to teach me about kissing and stuff, there's really only one that I would really trust." my little sister said as she looked right into my eyes.

When the meaning of her words finally sank into my brain I said, "You can't mean ME? I 'm your brother! It would be like incest! I can't do it!"

"Matt, there is no one I could trust more than you. You are older and more experienced; I'm sure you have been with lots of women and have lots of experience. And I know that you would never take advantage of me or my inexperience. You love me, don't you?"

"Of course I love you, you're my sister! But that's just the point! You're my sister! Of course I would never take advantage of you, I have always tried to protect you. And, yes, I have had some experience, but not as much as you seem to think. And think how awkward it would be ... we're brother and sister!"

"That's my point," she said. "You already do love me, and I love you. I know that you could never take advantage of me, and you would always want what is good for me." Then she threw her arms around my neck and kissed me again, but this time on my lips. It was not a passionate kiss, but it was truly heartfelt and warm.

I relented. "OK, if we are going to do this, then we will need to act like a boyfriend and girlfriend. Since this is our first date, I want to impress you. I will pick you up at 7:15 and we will go out to dinner, then to a show. After that, we can see where things go."

Lisa threw her arms around my neck again and gave me a big kiss. I slipped my arm around her and held her there as I kissed her back. I could feel her breasts subtly moving against my side. When we broke the kiss I said, "I'll see you at 7:15." Then I walked carefully out of the room, trying to hide my erection from my little sister's view.

I showered and shaved and did all the things I would normally do before going out on a date. I dressed nice, maybe even a little nicer than I normally would, but this was a special date!

I had told the parents that Lisa and I were going to grab a bite and take in a movie. Mom thought it was 'so sweet'. Then, I was waiting in the living room at a little before 7:15. When Lisa walked in I nearly had to pick up my eye balls off the floor! Her dress showed every curve to perfection. It showed more cleavage than I realized my little sister even had, and it only came down a few inches below her delightfully round butt cheeks. This was going to be a real date!

"Lisa, you look ravishing!" I exclaimed.

"Why, thank you, kind sir."

I extended my arm, which she took and pulled her body close against mine so that I could feel her soft breast pressed against my side.

I led her to the passenger side of my car and opened the door for her. "You are such a perfect gentleman," she said as she turned her legs into the car. As she turned into the seat, I could not help but notice an expanse of soft white thigh exposed nearly to Nirvana in the process.

I had made a reservation at a local Italian restaurant known for its excellent food and reasonable prices. The tables were candle lit and had white table cloths. It was the perfect place for a first date. I ordered a bottle of wine with dinner, but since I was driving, I only had one glass. So Lisa enjoyed the rest.

We enjoyed a leisurely dinner and drove to the 9:00 PM show. It was a 3D remake of "Titanic", so it appealed to both of us, and the 3D effects were stunning.

After the show I drove to a secluded spot where we wouldn't be disturbed. I thought that our parents would find it strange for us to be sitting in the driveway for an extended period of time. We talked about the movie and dinner for a while; I had put my arm around Lisa's shoulders. Then I pulled her toward me gently and she moved willingly. I bent towards her and our lips met, warm and welcoming.

The kiss continued on and on until I traced her wet lips with my tongue. I felt her tense for a moment, then relax as her lips parted slightly. I traced along her lips as our kiss continued, feeling the edge of her teeth with my tongue. Then she relaxed some more and allowed my tongue to enter her mouth.

I explored her mouth and caressed her tongue with mine. Our kiss continued and she began to reciprocate and our tongues began to dance.

As we kissed and our tongues danced within her mouth, I suddenly sucked her tongue into my own mouth while swirling my tongue around hers. As the kisses became more passionate I took her opposite leg and pulled her toward me. The feel of my hand on her soft thigh was intoxicating. Our passionate kisses continued as I caressed the back of her bare thigh from knee to buttock.

We were both panting by this time. I broke the kiss to kiss and nibble on her jaw, ear lobe, and neck. I kissed and sucked on her neck along her jaw line and then down her neck and throat until I was kissing and sucking along the sensitive area where her throat met her body. Lisa was making little mewing sounds and pulling me tighter against her.

Then she surprised me by reaching up and pulling the top of her dress down off her shoulders to expose her chest and breasts almost to her areola. I continued to kiss her neck and collar, then moving further to the newly exposed flesh of her upper chest.

At the same time I was holding her leg pulled tightly against me and I could feel her hips gently undulating against my erection. There was no denying that I had a massive erection and that it was a reaction to my sexy little sister! And she was humping against my hard cock!

With a massive effort of self-control I finally disentangled myself from this sexy woman. I nudged on the shoulder of her dress and Lisa worked it back into place. I said, "It's getting pretty late, I don't want you to get grounded for being out after curfew."

"It's alright; my parents think that I went to a movie with my brother!"

We held hands as I drove back to the house. In the hallway outside her bedroom I took her into my arms and gave her a very deep kiss. When we stopped I said, "Thank you for joining me tonight and I hope that I can see you again soon."

She responded, "I had a wonderful evening and I look forward to our next date." Then she slipped into her room.

I walked across the hall and entered my own room. As I got undressed my mind was spinning as I considered the evening. She had said that she wanted to learn about "kissing and stuff". Just how much 'stuff' did she want me to teach her? Was this really about teaching her? I REALLY wanted to pull down the front of her dress to caress and suck on her breasts and nipples. I loved the way she was humping against my erection. What was I thinking? What was I doing?

As I reflected on my date with my little sister, I recognized just how powerfully aroused I had become ... both earlier, and now as I thought about it. I was thinking about pulling out my hard cock to masturbate when there was a tiny knock on my door, followed almost immediately by the door opening and Lisa entering my room. While the lights were off, I could see enough to tell that she was wearing only a spaghetti strap top and panties! I already had a hard-on, now I felt like I might explode!

"Can we talk?" my little sister asked.

What was I to say? "Of course," I replied.

Lisa came over and sat on the edge of my bed next to me. "Is that what a 'real' date is supposed to be like?"

"Well, it was our first date, so I wanted it to be special. But a date can be anything that allows the two of you to be together and enjoying each other's company. It can be a picnic or a hike in the mountains, a trip to the museum or birdwatching. Anything that the two people can do together and enjoy the experience and each other's company can be a date." I said, not wanting Lisa to have an unrealistic view of what dating should be.

"Oh, I understand that. But at the end, the kissing and stuff ... is that what usually happens?"

"Especially in the early stages of a dating relationship there is usually a great deal of sexual passion, so kissing and other foreplay is especially intense."

"Intense? I felt like I was going to melt! Or burst into flames!" Then she paused, "But I'm really a virgin, though I broke my hymen with a little vibrator Jaymie got for me," she said blushing so intensely that I could see it even in the semi-darkened room. She went on, "I'm not sure that I am ready for a sexual relationship," she said as she continued to blush profusely.

"Nearly every relationship between a boyfriend and girlfriend is sexual at some level, although it may not include intercourse. When we were kissing you said that you felt like you might burst into flames. You were sexually aroused, right?"

"More than I have ever been with a boy. Probably more aroused than I should admit!"

"And I was just as thoroughly aroused as you were." I replied honestly.

"I know, I could feel 'it'!" Then she continued, "But what happens between 'kissing and such' and full sexual intercourse? ... When you're ready for 'more' but not going 'all the way'?"

"There are many levels of intermediate sexual activity. For example, 'dry humping' , which we did a little of last night, can become extremely intense."

"But doesn't that just increase the frustration level of both people?"

"It can, especially if you remain at that stage for too long."

"Then what?" Lisa pressed.

"You masturbate, right?" When she paused, I continued, "Of course you do, you just told me that you have a small vibrator. Having another person's hand bring you to a climax is a totally different experience, and a bonding experience."

"So, like, you would rub my pussy while I was whacking you off?"

I paused, then replied, "Yes, your date could be rubbing your sex while you stroked his. In this way you each provide pleasure to your companion, while at the same time learning nuances of their sexual responses. Of course, you could also each masturbate simultaneously while your partner watched. For some couples this is a good intermediate step, for others it is so private and personal that it cannot be comfortably shared ... at least until the relationship has progressed far beyond this point."

"I think I would like to watch you masturbating," Lisa said with a shy smile.

"Of course, that would have to be mutual. I am certain that watching you masturbate yourself to a powerful climax would produce explosive results for me, too."

"Oh!" By this time I had turned on the bedside lamp. It didn't provide much light, but it was ample to show Lisa blushing yet again. It was also adequate to reveal to my eyes just how little clothing Lisa was wearing, and how her nipples were hard points trying to poke through the thin fabric.

My cock was throbbing with need, but I tried to remain calm.

"What else can couples do, if they chose not to have intercourse?" She almost whispered.

"There is oral." I said with a slightly strangled voice. Talking about all of this while looking at this vision of sexual desire was taking me to the limits of my self-control.

"Oral? Like a blow job? Really?"

"Well, yes and no. A blow job usually implies a one sided encounter where the girl is doing all of the giving, and the guy is getting all of the benefit. I'm really talking about oral sex with mutual sexual giving and receiving."

"Really? Like you would lick my pussy? And make me climax? You would do that?"

"Yes," I whispered. "I would happily do that for you, and so much more."

There was silence for several moments as we each absorbed the implications of our conversation. Eventually, Lisa nodded, as if to herself.

"I know that you are hard, I can see it even though the blanket." She paused again, then she quietly said, "I want to watch you masturbate."

I couldn't believe my own ears! MY LITTLE SISTER wanted to watch me masturbate. AND that implied that she would let me watch her do the same! "You know what that means, don't you?"

"Yes," she whispered. "And I want to see you naked!"

With that Lisa pulled the tiny top she was wearing over her head and tossed it onto the floor. I didn't think that my cock could get any harder, but it jerked and throbbed nonetheless.

Lisa's breasts were a dream come true! They were full and firm, standing up proudly with hard nipples pointing out towards me. She had the most perfect breasts I had ever seen! "God, you're beautiful!" I said without thinking.

"Thank you, kind sir!" She said with a smile. "Now it's YOUR turn! I want to see you!"

Now it was my turn to be shy. Did I really want to have my little sister see me naked? No. Did I want to be naked with this incredibly hot and sexy woman in my room? YES! I pulled the covers down to my waist, exposing my bare chest.

"OK, now together!" Lisa said as she hooked her fingers into the waistband of her panties. "3, 2, ONE!"

Just like that, the most beautiful woman in the world was standing naked in my room! She grabbed the blanket and gave it a tug, and I was lying naked in front of her with my hard cock waving in the open air.

"WOW!" I said, stunned by her beautiful naked body.

"Wow," she said quietly as she looked at my hard, throbbing cock.

I scooted up on my bed as Lisa settled closer to my feet, swinging her legs onto my bed facing me. She opened her legs and exposed her moist, virgin pussy to me. Then she placed the fingers of her right hand on her pussy lips while looking directly into my eyes. Without conscious thought I took my cock into my hand and began to stroke it.

Our eyes focused on each other while our peripheral vision watched each other stroking their own sex.

We looked into each other's eyes, our passion clearly rising. She rubbed her pussy lips and clitoris as she looked at me. I was pumping my hand up and down my throbbing cock.

She rubbed herself faster, and I pumped my cock faster. Lisa took her left hand and began to caress her breasts, i nearly lost it! She began to concentrate more of her strokes on her clitoris, I pumped even harder. Her fingers were nearly a blur as they moved urgently over her clitoris, while I pounded my cock harder than ever before.

On and on we went, never breaking the intimate contact with our eyes, the stimulation of our sex becoming more intense, then frantic. I could see the rosy blush creeping across her breasts, chest, and up her neck. Then she exhaled a mighty moan as her body began to convulse with a powerful orgasm. That was the final straw for me. I began to spurt blast after blast of my thick semen, shooting it all over myself, the bed, and even some onto her. I continued to pump stream after stream of my semen, albeit with less force, until I was totally spent while Lisa rode through wave after wave of orgasmic contractions.