Lisa the Game Player (Part #1)

Lisa Cashman, age 14, loves two things: her tutor's collection of classic board games and watching porn. She manages to combine those two passions with him.

Author's note: This is a reposting of one of my stories that was removed from this website in May 2025. With the rules being liberalized to now permit stories involving 14-year-old characters, I made the necessary edits and revisions so this story can be enjoyed once again.

Part One

A brother and sister, William and Lisa Cashman, were two of my tutees in the mid-2000s. They were the only ones who lived within walking distance of my house. I could literally see their home at the intersection of two streets whenever I stepped onto my porch to collect the mail. Accordingly, they almost always arrived by themselves, on foot, for their weekly lessons.

William, a high-school pupil, needed a little help in English/language arts. (He had trouble following the plots of short stories and novels.) Lisa, in grade eight, required help in a lot of subjects, especially math. William was a tall, athletic boy whose good looks probably caught the eyes of some of the girls in his school. Lisa was nothing like her brother at all. She was a short brunette, a little bit chunky, and was average-looking at best. Both of them were pleasant kids who were easy for me to get along with. They were a fun pair to tutor.

Their parents came from Newfoundland. In Canada, Newfoundlanders are renowned for their generosity. Despite Newfoundland being a have-not province economically, its citizens are remarkably kind and giving, generally putting all others to shame. Because a great many “Newfies” do not even graduate high school, they are frequently the targets of jokes that paint them as hicks and buffoons. Americans tell Polish jokes. Swedes tell jokes about Norwegians. Canadians tell Newfie jokes. They take it in good stride, though, creating many of those jokes themselves! Newfoundlanders are also known for one other thing: sexual activity. Statistics about carnal pleasures indicate, year after year, that Newfoundlanders, on a per capita basis, are more active in the bedroom than residents of any other Canadian province. “It’s the only category where we’re number one in Canada!” a Newfoundland-born neighbor once proudly told me with a chuckle. Lisa Cashman continued that tradition.

The first time Lisa came to my house for a tutoring session, she was fascinated by the number of hands-on, traditional games I had on my shelves and in my closets. To kids Lisa’s age, “games” almost always meant video games. I was “old school”, though: I had acquired board games by the dozen. I never got into video games, even when I was a teenager when their popularity was soaring. Whenever Lisa got down to business and we finished her school assignments and anything else I had created for her to do, she would select a board game and we’d play it until her hour expired. This went on for quite a while. Lisa frequently became annoyed when we ran out of time and had to abandon a game before it was completed. Once, out of frustration, Lisa asked me, “Can I just drop by occasionally and play games with you?” I replied, “Sure. If I have no students here and nothing else going on…why not? I think that’s a great idea.”

That same night, Lisa’s mother phoned me. She thought Lisa had taken advantage of my kind-hearted nature. “I understand Lisa has invited herself over to your house to play games,” she said. “Lisa can be pushy and manipulative sometimes. As far as I’m concerned, you don’t have to keep your promise to her about this because she sort of twisted your arm.”

“Not at all,” I insisted. “Lisa likes playing these old-fashioned games I’ve collected over the years. I honestly get a kick out of showing them to her. I don’t mind a bit if Lisa wants to come here and play them with me when we both have nothing else to do. I’d enjoy it, too. She’s welcome to come here anytime whenever I’m not busy with another student.”

Lisa accepted my offer with alacrity. Three times in seven days she knocked on my door. Each time fortune was on her side: I had either finished my tutoring duties for the day or I had no students scheduled at all, so I invited her in. We played Trouble, Chinese checkers, Risk, and some really obscure board games. On a couple of occasions the following week, I reluctantly had to turn her away because I had a student arriving, a student already here, or some other commitment. From that point forward, Lisa smartly telephoned in advance to see when I was available. Of course, she was also still on my schedule as a regular tutee as well as my frequent playmate.

One Saturday night while Lisa was trouncing me at Chinese checkers, I curiously inquired, “What do you do for fun at your own house?”

“I play video games with William,” she said, “but I like these old board games better.”

“You have good taste, Lisa!” I sincerely congratulated her.

Lisa continued, “Sometimes I go onto the internet chatrooms for girls my age. Sometimes I watch sex videos.”

I was taken aback by the last sentence. The casual way in which she uttered those five words was more surprising than the actual words themselves. Lisa was bluntly matter-of-fact in what she had stated! It was as if she had said, “I like watching the Cartoon Channel.” I naively figured this pleasant, chatty eighth-grader was simply not this type of girl.

“Oh, you watch sex videos, do you?” I asked, just to make sure my hearing was okay.

“Yeah, sure,” Lisa reiterated. “My father has a subscription to a porn website. William found out his password and he watches porn more often than Dad does. Then I found out the password from William. When I have nothing else to do, I pretend to be my father and log in to that website. I’m trying to learn things from those videos.”

“You’re trying to learn things from porn videos?” I repeated with a degree of disbelief.

“Yeah,” she said quite candidly. “I’m 14 years old now. I hope to have a boyfriend soon. When I get one, I want to know what to do and how to do it.”

I thought to myself, “For someone who enjoys old-fashioned types of games, Lisa certainly does not have old-fashioned morals.”

“What exactly do you hope to learn from these videos, Lisa?” I asked, sounding more like her angry mother than her tutor.

“Pretty much everything,” Lisa said without the slightest hint of modesty. “Some of the girls in my class already have older boyfriends. They do sex things with them. I don’t want to be left out of anything. Boys expect girls to be good at sex. I’m right about that, aren’t I?”

“Not 14-year-old girls!” I retorted. “At least not when I was your age!”

Lisa remained unflappable and said, “Let me show you what I mean. If you have the internet on your computer, I’ll show you some of the videos I watch.”

I was curious enough to let Lisa take this further. I offered her my desktop computer—and she accessed exactly what she was looking for like a pro. It was obvious it was something Lisa had done a great many times. The website had about a dozen different categories and seemingly hundreds of sexually graphic videos on its menu. The first one she clicked had a busty blonde girl in pigtails and wearing a school uniform. “I doubt she’s really a schoolgirl,” Lisa pointed out. “I think they just dress her that way to make her seem young to the viewers.”

“You are very perceptive, Lisa,” I noted.

Lisa continued, “Look at what she’s doing to that guy’s penis! She’s fondling it, licking it and rubbing it against her boobs. I’ve seen this video about ten times already. Pretty soon the man will shoot white stuff from his thing. That’s called coming, right?”

On cue, the male on the screen ejaculated a huge load onto the alleged schoolgirl’s face and prominent chest. “See, isn’t that cool? I want to do that with a boy sometime soon.”

Then Lisa clicked another video that featured especially well-endowed males showing off their talents and their mastery of various sexual positions. The Asian girls in this video seemed especially submissive. “I like watching how they fuck,” Lisa frankly admitted. “I get a warm feeling running through my body when I see people fuck. Look, I think that’s called ‘doggy-style’ when the man sticks his penis in the girl from behind. Is that right?”

I didn’t know whether to be amused, appalled, or dumbfounded by Lisa’s fairly accurate sexual commentary.

Lisa admitted, “Some things in these videos I don’t understand, though.” She paused for a few seconds and suggested, “Hey, maybe you can teach me what I don’t already know! After all you’re my tutor—and a guy—and I’m a girl. This could be fun!”

I knew we were now detouring into dangerous territory. I was probably already in violation of several federal statutes by allowing a minor to watch pornographic movies on my computer in my house.

“This type of thing could get me into really big trouble, Lisa,” I informed her.

“Not if I don’t say anything,” she insisted. “I’m pretty good about keeping secrets. Neither my father nor my brother know I have the password to this website and that I watch it for a couple of hours each day. I’ll tell you what: Let’s watch one more video. It’s one of my favorites. When it’s over, we’ll play a game of Trouble. If I win, I get to choose a sex thing from the video to do on you. If you win the game, you get to choose one to do on me. What do you say to that?

Despite the fact that I had never once looked at Lisa in a sexual way, the last five minutes of our conversation had certainly gotten me aroused and more than a little bit interested in Lisa’s surprising hobby and her liberal attitude toward casual sex. “I say Trouble is an apt game to play, Lisa!” I pointed out. I’m not sure she understood the double meaning. “However, if you want to do this, yes, we can do this. Go ahead, Lisa. Play the next video.”

The video Lisa chose was one of those contrived “casting-couch” flicks that allegedly has some naive female newcomer showing up for a modeling interview only to be sweet-talked by the director into doing hard-core porn with him. It contained all the basics for sex, so there were plenty of activities for the winner of our game to choose from. To me it was a win-win situation. If Lisa won our game of Trouble, we would have sex. If I won the game, we would have sex. I assume Lisa felt the same way about the possible outcomes.

Part Two

Twenty minutes later, I was victorious in the Trouble game. Lisa didn’t seem too upset about losing. In fact, she said to me, “We might as well both get completely undressed for this. There’s no point in either of us wearing any clothes. Let’s get naked! Don’t be shy.”

Lisa seemed quite eager to show off her young body to me. She had a small pair of firm 14-year-old boobs that she proudly flaunted. She squeezed them together for effect, like a porn star, showcasing her goodies for me. Lisa had considerable pubic hair surrounding her vaginal area, which surprised me a little bit because of her age. My penis was only partially erect, but it was slowly rising. “I like the looks of your dick,” she told me while flashing a naughty smile. “If I win the next game, I’m going to suck on it for a long, long time!”

I laughed at Lisa’s enthusiasm. “Well, since I was the winner of the first game, I’m going to play with and suck on your breasts, Lisa. Okay?”

“Sure, it’s okay,” she said. “I lost; you won. You get to do whatever you like with me. That was the deal we made. Come and get me!”

I took a few steps towards Lisa and scooped her into my arms. “I hope you like my boobs,” she said. “My nipples are already hard.” Sure enough, she was correct. Lisa’s nipples were standing at attention. As a matter of fact, so was my penis at that point.

I placed Lisa gently on the nearby couch and put some small pillows behind her back. Lisa cupped her breasts with her hands, leaned forward slightly, and shoved them at me. “I’ll take over from here, my dear,” I told her.

I fondled both her breasts simultaneously, rubbing Lisa’s hard nipples as part of the fun. Then I sucked on the left one, pulling her nipple forward with my lips. This was a total turn-on for me and I felt my hardon growing stronger. Next, I did the same with Lisa’s right breast, this time doing more licking than sucking. “You have a nice pair of perky little tits for a 14-year-old girl,” I truthfully told her. She grinned and thanked me for the compliment.

Out of curiosity, I stopped my licking and sucking for a moment to ask her what I felt was an important question: “Lisa, is this the first time you’ve done this sort of thing?”
“Yes,” she claimed. “You are the very first guy to ever play with or suck on my tits. I like the feeling. Keep on doing it, please.”

“Absolutely,” I replied. “If it’s not against the rules,” I added, “I’m going to give you a titty-fuck, too.”

“I know what that is!” Lisa interjected. “That was the part of the video where the guy put his penis between the girl’s tits. She squeezed them together as the guy slid his dick back and forth against them. Am I right?”

“You certainly know your sex terms, Lisa! You must watch hundreds of hours of video pornography!” I exaggerated--perhaps. “Anyway, here I come for a titty-fuck.”

“Let me help you,” Lisa said. She grabbed my hard dick and helped position it properly between her lovely, perky mounds. Lisa was halfway between a sitting and a reclining position. She was a very sexy sight; I knew I was going to ejaculate soon. I didn’t say anything in advance to Lisa. By choice, I wanted to totally surprise her with my sudden orgasm.

After about the fiftieth thrust, I felt my balls tighten--and I let go. Kaboom! A large gob of my goo struck her on the neck and under her chin. I firmly grabbed my dick and took deliberate aim for the subsequent blast. As I had hoped, it struck this 14-year-old sex fiend squarely in the face. Long sticky ropes of cum dangled from Lisa’s nose, lips and forehead. Amazingly, it didn’t bother her at all! Lisa giggled and smiled as she began to wipe away the white strands of cum with her fingers. I knew I had a little bit more jism left in my shaft for a small third spurt. This time I stationed my dick directly against Lisa’s lips hoping she would open her mouth. She didn’t. My weak ejaculation just hit her lips and cheek. A wee amount of semen ran off her face and onto a pillow. She had no inclination to swallow it. “Now that’s something you can work on, my dear,” I said in my best teacher voice. “Swallowing cum is the hallmark of a real sex pro. The next time I win a game, maybe I’ll just shoot my load directly into your mouth so you can work on it.”

Unexpectedly, a pang of guilt overtook me. As a rule, I don’t usually treat females as mere sperm receptacles even in the throes of hot coitus, but this was sort of an unusual occasion. Nevertheless, I gently said to her, “Come to me, Lisa, honey.” She fully sat up on the couch and I hugged her. I kissed her on her lips, and she responded in kind. We lovingly embraced for a solid ten minutes. I wasn’t a total gentleman, though. I continued to fondle Lisa’s breasts intermittently—just because they were there and they looked so inviting to me. “Sometimes kissing and hugging is just as good as sex, Lisa,” I tried to inform her.

“I doubt it,” she comically replied with the voice of authority. She added, “I think I’ve learned enough for tonight. Let’s wait tomorrow to have another game.”

“Yeah, I agree. You tired me out, Lisa, you little sexpot,” I said. “I’m not as young as I once was. Once I have one big orgasm I’m done for the night.”

She paused for a few moments and told me, “I’ve changed my mind about something. If I win the game tomorrow, I’m going to ride your dick until your balls hurt from coming inside my pussy. What will you do if you win the game?”

“It doesn’t matter,” I replied. “I’m no fool; I’m going to let you win. In fact, to speed things up, I forfeit tomorrow’s game right now. Congratulations, Lisa. You beat me.”