Lucky Lisa Ch. 01

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Jack and Lisa become masturbation buddies.
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I’ve always enjoyed watching adult web cams. I guess you could say it is one of my fetishes. I’m a member of one of those websites that lets you view for free. The amazing part, to me, is that a lot of great looking women take part in it, too. I find it to be more arousing than porn since it is live and you can actually talk to the person.

I have had no problem getting off to these ladies. Sometimes I even show them as I get off to them on my cam, which makes it even more exhilarating. There are my regulars who are usually on at a certain time every day (I keep track), and then you have your irregulars, who sometimes you won’t see for months. These women range from all ages too, from the young, ripe age of 18 to the seasoned veterans of 60+ years. Of course, being 19, I’m only attracted to those under 40 (unless she looks really good).

It’s a mutual thing; I enjoy their wonderful, gorgeous bodies and they enjoy my youthful view on sex, and sometimes even my masturbation. For instance, I’ve made quite a friend out of this one girl. Her name is Lisa, she’s 24, and she lives in Las Vegas. Now, me living in Texas obviously prevents us from meeting in person, but we still have a great time. The best part about it is that not only are we masturbation buddies, but we are also good friends. We chat in private messages about the many interests we share. Then at night, our world changes and we masturbate to each other. It wasn’t always like this, though.

One night, around 2 am Texas time, I was wanking my rod in a slow, bored fashion, half-hard and tiring out. None of the regulars were on and it was still about another hour before the overseas regulars would start to come online. Just as I was about to close it out and go to bed, I saw a new ID show up on the list, “luckylisa”. I thought, “Hell, it’s probably just another old lady, too wrinkly for me to enjoy. But, I might as well check.”

So, I clicked her ID and the feed opened. What I saw was the most beautiful thing I had seen anywhere in a long time. She had straight black hair, entrapping emerald eyes, a wonderfully expressive, cute face, and an hourglass figure with full curves in the front, and a tattoo of a sun on her right arm. I couldn’t see much below her waist since it was a camera and she was sitting down. She wore a white, sleeveless shirt and black bra straps rested upon her shoulder. I was hard again instantly, but not only was I horny, I was attracted.

I had to find out more, so I opened her profile and read after stroking a little to the picture of her holding up her busty cleavage. It said she was from Las Vegas, 24, and enjoyed gambling and drinking. She sounded so fun and so right to me. I needed to talk to her. As I kept an eye on her cam’s feed, she was pretty much motionless the whole time with a few shifts here and a few smiles there. Once in a while she took a shot of tequila.

As I started to surf the chat rooms to track her down, I kept thinking of every sexual position I have ever studied with her, and I stroked with my left hand as my right hand navigated through chat rooms. Eureka! I finally found her and entered the chat room, which was loaded with thirty guys or so, all trying to do the same thing: get Lisa to strip so they can jack off to her.

With every man’s flirt, I became less and less interested, thinking she was probably just another slut to get off to. But then came a response from Lisa, telling them to fuck off. She wasn’t a slut; she didn’t strip for just anybody! Maybe I did have a chance, but how was I supposed to get to know her with all of these hound dogs?

I did the only thing I could do. I started to talk to everyone, mostly her though. I watched other men’s questions and studied every response she fired. That night was not very productive except for my studies. I came up with the theory that to get her naked, and better yet, to be her friend, you’d have to give her a lot more respect than what these guys were giving. She talked to me, but it was a very cold conversation, which I understand from her point of view. I was just another guy trying to get off as far as she was concerned. After I signed out for the night, I formulated a plan: talk to her every night about things I enjoy, and don’t ever mention sex or flirt for now.

I made it a goal to be on about that time every night for the next week or so, and it paid off. She was on precisely at 2 am Texas time every night that week. I completely ignored what other men said to her and me and focused on becoming her friend. Slowly my plan took its course, and within the next week, she was talking to me for hours in private messages. We talked about everything, and we enjoyed each other’s companies. Within another few days I began subliminally working in flirts, and she responded positively.

Then came the great night, the first night. I logged on as usual and so did she. I opened her cam feed and instantly noticed a difference. She was wearing her regular shirt, but she wasn’t wearing a bra. I thought this was funny, but when I said hello in the private message I didn’t mention anything. Her response was anything but her normal, and it contained many errors that she usually didn’t make. Something was different.

We talked a little, and she flirted with me a lot. I was surprised at this, but I flirted right back since I had a huge bulge in my boxers. Finally, I saw her fill a shot glass to the rim with tequila, and I knew what it was: she was drunk. My dirty-sided conscience told me to take full steam ahead and see if I could get her naked, while my clean-sided conscience said to get her naked but keep it friendly. It was unanimous; it was time to see her naked.

As she took another full shot every five minutes, I responded to her cock-hardening flirts. Finally, with my last bit of good resistance, I mentioned her drunkenness to her. She said, “I know,” and began laughing hard as I watched her try to shoot down another round through her outrageous laughter. I couldn’t help from being turned on and began laughing myself. Then she said, “Turn your cam on, Jack. I want to see you.”

I obediently hooked up my web cam to my computer and aimed it at my face. “Ah, there’s my Jacky-boy!” she typed. I couldn’t help but laugh at the name she had referred to me as. She poured and drank another round as I sat and watched in disbelief. “Want some?” she asked.

“Yeah, I do, but I can’t quite reach all the way to Vegas,” I told her. She began another wild laugh at my response. I had to laugh too, though I wasn’t laughing at my joke, which I thought was dumb, I was laughing at her. Finally I said, “You’re wasted.”


This caused her to laugh even more. Then, I saw her settle down all of a sudden, as if an invisible person had smacked her. I watched her lean over and type something. I knew something serious was coming my way, so I prepared myself for anything.

“Jacky-boy,” Lisa asked, “Are you wearing any pants right now?”

I felt a little embarrassed at the question being my modest self, but told her, “Nope. Just my boxers.”

“Wow! Can I see? Please? Please?” she asked.

I began laughing at her child-like behavior, but then said, “No,” since I had a boner caused by her. I didn’t know how she would react to it if she saw it.

“Why,” she asked cleverly gazing into the camera, “do you have something you don’t want me to see?” Now she was up close to her camera, giving me the biggest, cheesy grin I’d ever seen. I couldn’t resist her taunting charm. I stood up, showed her the front of my boxers, spun around quickly to avoid showing her the sides, and showed her the back of them.

My efforts to avoid showing her my protrusion failed because the next thing she asked was, “Damn boy! Where’d you get that huge banana in your pants?” Lisa now had a clever grin on her face.

My cheeks turned red as I read her question and sat back down. I laughed, as I knew I was caught, but I decided not to respond. She looked at me sarcastically in the camera after guzzling another shot of tequila, then said, “Well? What was it? Were you looking at porn, or was it me? C’mon.”

I shook my head in the horizontal fashion as she showed her artificial anger with body language. “Well I guess I can’t get you to tell me,” she continued, “but I sure hope it was me. I’d love to know that I could turn on a cock that big. In fact, I’d love to fuck a cock that big. Oh, God, I haven’t had cock in so long. I’m so lonely. How big are you Jack? 7, 8 inches?”

With my face now entirely maroon with embarrassment, and shock to what she had told me, I had no choice but to speak. I put on the most modest face I could and typed slowly, “Yeah, it was you. I hope you aren’t mad. It doesn’t sound like you are. And yes, it’s 7 inches.” I pressed the Send button and lowered my head to re-compose my thoughts.

When I raised my head, I saw Lisa take another full shot and type back, “Damn Jacky-boy! You’re making me so horny right now. I feel all hot and sexy. I wish I could have you in me.”

I was so turned on, yet so shy; all I could muster up was the Internet favorite, “LOL.” Then, I saw something on her feed that I had never expected her to do. She leaned all the way back in her office chair and rolled her shirt up above her breasts, exposing them to me for the first time. Like a tractor beam, my left hand was drawn to my cock and started stroking my rock-like penis. I moved my hand so that she couldn’t see (or so I thought) it moving. I had achieved a goal! Lisa was now naked, at least from the top up. Not only that, she was turned on by me as she caressed her nipples and squeezed her breasts for a good five minutes.

By the time she sat back up and put her shirt down, I hadn’t realized that my cock was already ready to spew. She took another shot and said, “Oh Jack, you made me so horny. Would you mind if I masturbate to you?”

My shyness had left and the only thought in my mind was, “I want to fuck her brains out.” So, I replied, “Absolutely not. Have at me.” She laughed as she stood up and pulled her shirt completely off, exposing me her full body. The only piece of clothing she wore now was her gray cotton panties which were about to come off as well. I wasn’t sure, but I swore that I saw a wet spot on her crotch. I knew she was hot for me, and I for her.

Lisa danced around in an erotic fashion, playing with her breasts some more as I conspicuously jacked off to her. Then, She stuck her right hand down her panties and began fingering herself, giving me orgasmic facial expressions, only tensing my cock even more. I saw her pause for a moment and lean over to type, her beautiful breasts with her erect nipples hanging freely in front of her camera.

“Oh baby,” she said, “My pussy is so juicy right now. I have to see your huge cock. It will make my orgasm so much better. Let me see it Jacky-boy. I want to watch you stroke to me. And don’t think I don’t know you’re already stroking under that desk! Show me! I want you to squirt your heart out for me!”

The only thing I could respond with was, “With pleasure!” I adjusted my camera and stood up to pull my boxers off. I turned around on purpose just to play with Lisa’s anticipation. I looked back at the computer screen as the camera focused on my butt.

“Oh God what a great ass!” Lisa typed as she fingered her nipple. Finally, I turned around and sat in my chair, leaning back, revealing my penis to her for the first time. “Holy shit! It’s bigger than I thought it would be!” was her response.

I laughed, then leaned back and began to stroke away. I knew it wouldn’t be long before I would fire. “Oh baby, you turn me on,” she continued to type, “stroke it for me! Spit on it and pretend I’m sucking it!” I did as I was told, and made myself even hornier in the process with the warm, wet saliva. I stroked the shaft, then the tip, then the shaft, played with my balls, etc as I watched her lick her nipples and play with them.

I sped up my stroking and she typed, “Oh yes! That’s it! Fuck me hard! I love your huge cock baby!” Lisa was now climbing in her chair, turned around, pulling her soaked panties off, revealing the folds of her clit to me and her rounded, perfect ass. She spun around in the chair to watch me some more.

I stroked faster as she began to finger herself and arch her back in erotic positions only the pleasures of sex could cause. This was it; she had done it. I felt my orgasm begin as my cum worked its way up through my balls and into my shaft. She could tell by my facial expressions that I was ready, and she re-positioned herself in her chair so that I could see all of her front side. Her crotch was shaven clean; the way I like it. Just before I let go, she typed, “Oh baby! Cum all over me! I want it everywhere!”

Though I was pretending to be there with her, my last shred of reality set in and I knew it would be a mess if I came on the camera or computer. So, I leaned as far back as I could and pulled my cock facing straight up towards my face so that I would cum on my stomach, or so I was hoping. My mistake was that I didn’t realize I had been stroking for a good thirty minutes, and that this was no porn; this was a real girl. This wasn’t going to be the normal “squirt, squirt, done” routine.

I watched as she began to finger herself rapidly and give me the most amazing facial expressions of pure pleasure. I gave my hand one last spit and stroked my wet cock to orgasm. It was the best one I’d ever had up to that point, but I got it all over me. The first stream went to my forehead and nose; the second on my chin and in my mouth; and the third on my chest and stomach.

I was covered in man goo as I kept stroking till the last streaming jet came. I must have had eight streams. I was full of cum for Lisa, and she was so turned on by it now that she herself was about to orgasm. I watched her as my functions returned. Then, with what looked to be a loud scream, she let out juices all over her chair and in her hand, which she then rubbed onto her breasts.

By the time she finished, I was just laying back relaxing, almost asleep. Finally she spoke up, “Oh Jack! You were so good. I wish you could really fuck me. Oh I’m so tired. I got to get to be baby.”

“I know, me too,” I said.

“What do you say Jacky-boy? How about we do this every few nights? Are we masturbation buddies?” Lisa asked.

“You bet!” I smiled. On that note, the evening was over. We had become mutual masturbators. The next few weeks went by smoothly, and she was rarely ever drunk for the most part, which made the experience even better.

After a few months, this had become my normal routine and it was as if I was dating somebody, but purely for fucking. Only she was thousands of miles away. It was great, and I was feeling good. Then one day, out of the blue, my father tells me that we’re going to Las Vegas to see my uncle.

My uncle! I had completely forgotten he lived there. Let’s just say I was packed two weeks before our plane was to leave. However, I still had my doubts. “What are the chances I’d see her in a big tourist trap like that? I could arrange to meet her, but I’d have to break away from the family,” were the thoughts crossing my mind. My next thought was only, “So do I tell her or not?”

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