tagMatureThe Landlady's Daughter Ch. 03

The Landlady's Daughter Ch. 03


This is the third story about a delightful young person who I have written about before in: "The Landlady's Daughter", and "The Landlady's Daughter 2." As I mentioned there, I had studied at a small New England college to be a professor of English, and my very first job as an assistant professor by pure coincidence was at the same small but expensive college where I had gotten my master's degree.

The job as an assistant professor didn't pay all that much, so at the beginning, I was required to find a modest accommodation somewhere around town. I found it in a small upstairs apartment in a nice suburban house owned by a single mother who worked at the city hall in the town. And like a character in a certain famous book, I was sold on the apartment when she introduced me to her daughter, Tiffany, who was 18 and a senior at the local high school but, since she was small and petite, looked more like 16.

Tiffany was beautiful. She was about five foot four, 105 pounds, and had red hair and pale skin, as most redheads do. I had found out a short time after moving in that she had a pretty red bush as well. (Read the previous stories for how I found that out.) At the time that this story took place, I had already been living at the apartment for about nine months.

Tiff was always home from school by about 2:30, while her mother did not get home from work until about 6 p.m. So that left Tiffany with plenty of time to relieve her boredom, since she was often bored. As indicated in the previous stories, I was able to relieve her boredom many times and in many ways.

After changing her clothes into denim shorts that were short indeed and a cutoff gray t-shirt that was cut off about six inches above her waist, just barely covering what I could tell from her "points" were naked breasts, Tiffany walked into my room while I was reading some student papers.

"Mr. Baxter, do you know how to play chess?"

I looked up. "Yes."

"Do you think you could teach me?"

I sighed. "I suppose so. Why?"

"There's a guy in our class named Dennis. He's really hot, and I would like to get to know him. He comes from a rich family who have a big house out near the golf course. Anyway, his parents are renting a house in the south of France for a month and will be going there. So he has the whole house to himself for a month. He's going to have a chess tournament at the house next month, with a hundred dollars going to the winner, and I would like to enter it. But I don't know how to play chess."

"Then what makes you think you could win?"

"I don't think I could win. I just want to enter it to get to know him....So could you teach me?"

I sighed. "I have a lot of papers to read and grade."

"I'll make it worth your wile."

I knew what that meant, and I always found her offers to be ones I could not refuse.

"Okay, I'll make you a deal: I'll tutor you for one hour a day in chess until you're fairly proficient. Then we're done."

"Deal," she said with a smile. "When can we start?"

"This afternoon if you like."

"Great. I bought a chess set at the game store, so I'll bring it in."

"Okay." I was not really crazy about the idea, but little was I to know how interesting it was going to get.

I arranged the pieces on the board, and we sat down opposite each other.

"Okay, some of these pieces can move in only one direction, while others can move in a variety of directions. By the way, what did you have in mind for making it worth my wile?"

She smiled. "Have you ever heard of Strip Chess?"


"It works sort of like Strip Poker, only with chess pieces. And that's how the tournament is going to be played, Denis said."

"What do you mean?"

"There will be twelve people, six boys and six girls. They play matches until only one person is left—and that's the winner. So that's the chess I want to play with you—and that's your reward."

This was beginning to grow a little more interesting. I had already seen Tiffany naked a number of times of course, but watching her slowly strip in a chess tournament was a new and kind of kinky treat.

"Here are the rules," she said as pulled a small piece of paper out of the pocket on her shorts and handed it to me. I read it.

1.Any time you lose a pawn, you remove a small article of clothing, such as a shoe or sock. Jewelry, a watch, or money in your pocket does not count. 2.Any time you lose a large piece, such as a knight or a bishop, you remove a larger piece of clothing such as a shirt or pants or dress. 3.When you remove your last piece of clothing, such as shorts, a bra, or panties, you can either give up, and the other person wins, or you can continue, risking the two final things you have to offer: oral sex and finally, intercourse—otherwise known as fucking. If your queen is taken, you have to perform oral sex on your competitor in front of everyone. If you are checkmated, you have to fuck your opponent in front of everyone.

I laughed. "I don't know who made up this game, but it sounds very interesting. I wish I could be there."

"Dennis is going to record the whole thing with his camcorner. I'm sure I can borrow the tape afterward if you would like to see it."

"I would love to see it."

So I showed her how chess works by playing an actual game with her. First she lost a sneaker, then another. She was not wearing socks, so she could not lose them. Then she lost her shorts and then her cutoff T-shirt. I was able once again to admire her small but pretty breasts with their pale pink nipples.

"When I am going to win?" she complained.

"You're still learning. Don't expect to win when you're learning."

"I think this is a set up. You just want to see me naked."

"Or worse."

"Yes, or worse."

I took her bishop. She stood up and pushed down her candy-striped cotton panties. And she continued standing there while I admired her little red bush.

"Had enough?" she asked.

"Not yet. I'm really looking forward to see if you're willing to place your last two bets. I'd love to watch you suck my cock, and to moan like you do when I'm fucking you."

"Nice talk from a teacher. You're supposed to be my role model. What if I told my mother what you just said to me?"

"She wouldn't believe you. I also wouldn't mind seeing you get fucked by someone in the tournament."

"Wouldn't that make you jealous?"

"Of course, but I still would like to watch it."

"You're a pervert."

"Takes one to know one. Are you still in the game?"

"Yes, I'm ready to put up my next to last thing."

"Good, then let's continue."

But she had apparently had forgotten the long move in one direction that a rook could make—so I easily took her queen.

"Shit!" she said.

"So now you have to pay up. It will be good practice for the tournament, since you'll probably have to pay up there too. You should try to get Dennis as your opponent."

"I know. I would love to suck his cock."

"With ten people watching?"

"Of course."

"You're a little exhibitionist."

"I know."

"Okay, let's pretend you're in a Sex Education class in the high school. Twenty other students are there, male and female. You brought me in as a subject, and you're going to show the other girls how to give a really good blowjob. The boys can just watch."

"That sounds kinky."

"Want to do it?"


"Then do so."

She stood up and turned completely naked to what she saw as an imaginary audience. "And now, I'm going to give a demonstration of a really good blowjob," she said. "Mr. Baxter, an assistant professor at the college and my friend, has agreed to be my subject."

I waved to the audience—as Tiffany got down on her knees.

One thing I liked about Tiff is that whatever the sex act was, she always wanted to make it last as long as possible. So she was good at a slow and tantalizing blowjob.

"A good blowjob should always end with him coming in your mouth," she said to the class. "Then you should open your mouth to show it to him—and then swallow it."

She took my cock in her mouth and slowly started circling it with her tongue—while moving forward and back.

I was a 37-year-old man, and she was an 18-year-old girl, but there is only so much a human being can take. After about ten minutes of this, I groaned and came in her mouth. She opened her mouth and showed it to me, then she swallowed it.

"Yum, yum," she said.

I'm sure that was a lie, but so what? It was the right response.

"Now, since you haven't lost anything, I'm going to beat you for the rest of the game," she said, as she stood up and sat back down on the chair. "You don't stand a chance."

"Yeah, right."

All it took was one more move from my knight and one move from my rook—and she was cornered. "Checkmate," I said.

She looked at the board. "Are you sure?"

"You're done. There's no escape for your king."


"That's what you said last time."

She looked around. "So do I have to fuck you in front of all these people?"

"That was the bet."

"Okayyyyy." She stood up. "Can we all go to the other room? It's more comfortable there." She looked at the other people. "You can come too."

"All right." I stood, and she led me by the hand over to her bedroom. Then she jumped up on the bed, flopped down face up, and spread her legs. "Ready when you are."

"I'm ready." I knelt between her spread thighs and eased my still-hard cock into her tight but wet pussy. Then I fucked her as slowly as I could. It last about 20 minutes, but finally we both came at about the same time.

"I think you cheated me," she said, with my cock still in her.

I laughed. "You were just a 'pawn' in my game," I said." And a naked pawn at that."

"I also think I was rooked."

"Very clever. You were."

So Tiffany went to the chess marathon, and I guess she got what she wanted from Dennis. A week later, she was able to get the video, and we watched it together. We had a rematch after it.

I think even Bobby Fischer would have liked it.


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