5 comments/  83304 views/  7 favorites

The Landlady's Daughter

By: Baxter72



I was thrilled at the prospect of being hired as an assistant professor of English at the small New England college where I had first gone on a scholarship as a freshman. I had been drafted into the peacetime army right after college and had traveled around the world some before enrolling in graduate school at Columbia University in New York City. I finally came out of it with a master's in literature and composition. 

All of my graduate work had been good, and the dean of the New England college seemed to be delighted to have me back.

But as an assistant professor, the pay was not that great, so I had to look around for a relatively cheap place to live—and a place that was close to the campus, since I did not have a car.

Luckily, the college maintained a housing bulletin board for both students and teachers, and that's where I saw the typed card:

Single room available for teacher or professor. Near campus. Charming older home. Use of all home facilities, including kitchen. $400 a month. 

The phone number was included of course, and the place seemed ideal, so I gave the number a call. 

It turned out the house belonged to a Ms. Jane Witherspoon, who told me that her husband had died of colon cancer the year before, so this was the first time she was renting out a room. The only other two occupants of the house were herself and her 18-year-old daughter Tiffany, who was a senior in high school. It all sounded good, so I made an appointment to look at it. 

Ms. Witherspoon was about 45, red-haired and looked like she had once been quite attractive but now was a little on the plump side. She said she now had to work during the day as a checker at the local supermarket. The house was on a nice tree-lined street near the campus.

She showed me the bedroom, which was upstairs. It was large and beautifully furnished, with three windows and a lovely leather easy chair. "I moved my bedroom downstairs after my husband's death because my knees are not so good," she said "So you room would be directly across from my daughter Tiffany's room, and there's a lovely bathroom at the end of the hall. You'll have to share the bathroom with Tiff, I'm afraid, but not at the same time of course," she added with a laugh. Little was she—or I—to know.

"This is ideal," I said. "I'll take it."

"Fine. Oh, here's Tiffany." She turned as she heard her daughter coming up the steps, apparently just home from school.

"Tiff, this is Mr. Baxter, an assistant professor at the college. He thinks he may take the room."

Tiffany smiled and held out her hand. "Hi!" I took it. My God, I thought, what a knockout. She was an extremely attractive young lady, about five-foot-four 105 pounds, with reddish-blonde hair—what they used to call a "strawberry blonde." She also had a very pretty face and sparking green eyes.

"It will be lovely to have a professor from the college living here," Ms. Witherspoon said. "I'm sure Tiff will pester you with questions about her homework, but you can ignore her."

"Okay." I smiled at Tiff, and she smiled back.

I soon found out that I could not ignore Tiffany, and what developed between us happened so quickly and with such daily regularity that after the first day, I began to keep a log of it. Here is the log:

First day after moving in: Like most people in the academic field, I enjoyed a lot of reading. So when I came back to the room after work, I poured myself a drink of bourbon and water, sat in the easy chair in my room with a good book and read for a couple of hours. But since I didn't like the feeling of being confined, I usually left the door open. Tiffany, when she came home from school, apparently took this as an invitation for conversation, especially since her mother did not come home from work until after five.

"Hi!" she said as she passed by my door and entered her room. 

"Hi." Her mother had told me that Tiffany was a member of the high school cheerleading team, and she had come home in her uniform of blue and gold.

She walked back into my room. "As you've already discovered, we don't have air conditioning in this house, so around this time of year, the upstairs gets a little stuffy in the afternoon. It's a good idea to have your window and your door open, and that's why I leave my door open. I'll try not to disturb you."

"Fine by me," I said. Little did I know just how disturbing I was going to find her.

She smiled and went back into her room. Her closet was on one side of the room, and her dresser was on the other side. So I couldn't help but notice when she crossed back and forth: the first time minus the blue and gold sweater but wearing a white bra and of course the skirt; the second time, minus the blue and gold pleated skirt but wearing the bra and skimpy white bikini panties; the third time minus the bra and panties.

Did she think I was not looking or something? Was she really that naïve? I got my answer when her little hand stuck out from the edge of the door and waved.

Second day:

Ms. Witherspoon had to be to work at eight, so she had already left that morning. Tiffany was supposed to be at school by eight, but apparently had slept late. I did not have to be in until nine or later, so I was taking a shower when there was a knock on the frosted glass door. I turned. It was Tiffany, in a white terrycloth bathrobe. Concealing myself as best as I could, I opened the door a little.

"What is it?" I asked.

"I got up late, and I'm going to be late for school. I have to take a shower."

"Can't it wait?"

"No, let me in with you. It won't take a minute."

Apparently, I didn't have a choice. She untied the robe and let it drop, then she opened in the door and stepped in. I caught just a glimpse of her little reddish muff before she turned her back to me.

"Can you wash my back?" she asked, handing me the bar of soap, "I can't reach it."

Still dumbfounded, I did what she asked.

"And my bottom," she said.

So I did that as well—lingering with it as much as I dared.

Finally she turned. "Thanks," she said with a mischievous smile. Then she got out of the shower, picked up her robe and trotted off to her room.

Well, this was a fine way to start the day, I thought looking down. I'll be lucky to get my pants on at all. 

Third day: 

Perhaps now you're beginning to get an idea of the déjà vu book I had mentioned at the beginning. The only blessing about this was that little Tiff was of legal age. She might have been eighteen, but she didn't really look more than fifteen. 

"Don't you ever get bored with reading?" she asked that day as she sauntered into my room.

I looked up. "No, not if it's a good book."

"What are you drinking?" She brazenly picked up my glass of bourbon and took a sip. "Whiskey."

Apparently she was no stranger to liquor, since she did not make a face at it. "Bourbon," I said, "and I think you're below the legal drinking age."

"I'm at home, so it doesn't matter."

"You look bored," I said.

"I am bored. There's nothing to do, except talk to you."

"Gee, I'm sorry for that. Do you play chess?"

"No."

"If you would like to learn, I could teach you. I think I would enjoy playing chess with you."

"Is it like strip poker? I've played that."

"No, it is NOT like strip poker." I could tell she was playing with me.

"It sounds like too much trouble. When I get really bored, I just masturbate."

Now that got my attention. "You just masturbate."

"Yes, I'm very good at it. I can have an orgasm in ten minutes or less."

"Wonderful."

"Since mother never comes up here because she's usually had too much to drink at night, I generally leave my door open. So you can watch if you want."

I smiled and shook my head. I had to admit it: That was one of the most attractive offers I had EVER received in my life.

"I'll think about it," I said.

"Okay." And she left.

Fifth day: I had come home early from the college and was sitting reading a book when Tiffany arrived home from school. 

A little later, she entered my room wearing her white terrycloth robe and carrying a red tube of Ben-Gay. 

"The only problem with cheerleading is that you get really sore muscles, and I have to put liniment on them when I come home from school. If you're not doing anything really important, could I persuade you to rub liniment on my legs?" she asked.

"All right." I put the book down on the bed and got up. It did not take much persuading.

"Thanks." She handed me the tube of liniment as she turned, and I followed her into her room.

She laid face down on her bed and pulled the terrycloth robe up to the backs of her knees. I straddled her feet and rubbed the liniment into her calves. 

"The backs of my thighs too," she said, as she raised the robe up to the bottom of her butt. 

I enjoyed that rubbing even more.

"And finally, my lower back," she said, as she raised the robe up to the middle of her back, exposing the beautiful globes of her bottom.

"Don't quote me on this, but you have the most beautiful little bottom I have ever seen," I remarked, as I spread the liniment on her lower back—which probably did not hurt at all.

"I'll bet you say that to all your girlfriends."

"I don't have any girlfriends. I just moved here, remember?"

"Then I could be your temporary girlfriend if you want. I like older men." 

I was 42, which I guess classified me as "older" in her book. "I would like that," I said. "After all, I've already seen you naked—which is what boyfriends are supposed to do."

"The front of my thighs hurt a little too," she said, as she rolled over, "If you would like to put some liniment on them."

Now she was completely naked before me: a tempting little morsel with small but perfect breasts, pert little nipples, silky white skin, and a small focal point of reddish brown hair.

"I don't think your thighs hurt at all," I said. "What do you think you're doing?"

"What does it look like? I've been on the pill for a year. My boyfriend and I do it all the time, but it's not enough for me. And I told you: I like older men."

"So you're offering yourself to me—in a sexual way."

"You could say that. Mom's not going to be home for another two hours."

I closed the tube, dropped it on the bed and got up. "I'm going to have to think about that," I said, as I walked out of the room—with the tightest pants I had known in months.

"Okay...Oh, Mr. Baxter?"

I turned. "Yes?"

"I just wanted to let you know that sometimes I don't wear pajamas. I like to sleep in the nude. So if you walk past my door some morning, and I've pushed the covers off in my sleep, I hope you won't be offended."

I smiled. "I'll try not to."

Sixth day: And as chance would have it, the next two mornings when I walked by her door, the covers had been pushed off during the night, and she lay there face down and sprawled like the most tempting naked invitation in the world.

So I ask you: How long was I supposed to resist this?

Seventh day: The answer came the next night around 9:30 p.m. I could hear that Ms. Witherspoon was downstairs watching TV. I was in my pajamas in the easy chair reading a book, and little Tiffany was across the hall getting ready for bed. Ready for bed in her case meant taking off all her clothes, lying face up and propped against the pillows and looking over at me...as she masturbated.

I watched her with increasing interest for awhile, and then I thought I would show her that two could play at that game. I pulled my nearly-erect penis out of my pajamas and began to stroke it. Considering the "view" I had, it did not take long for my penis to get fully erect. She giggled and covered her mouth with her hand.

I got up and walked over to her room—with my penis projecting from the front of my pajamas. She was lying there with one hand covering both of her breasts, and the other hand buried in her lovely little bush.

"It looks like you don't have enough hands for that job," I said, "Would you like a hand?"

"That would be nice," she said.

I took the hand that was buried in her little red bush, kissed and licked her fingertips and placed it over one breast. Her other hand was over the other breast. Then I slipped my middle finger into her warm and wet pussy. 

"Ummmm," she moaned. And she kept on moaning softly for another five minutes until she came—on my fingers. 

"Wow, you weren't kidding about quick orgasms," I said. "I'm impressed."

"How would you like yours?" she asked softly.

"Well, I don't want a handjob. After all the cock-teasing you've been doing to me for the past two weeks, I would like first of all to shove it down your throat and then fuck your brains out."

"That shouldn't take very long."

"I agree. Does your door have a lock on it?"

"Yes, just turn the bolt."

I got off the bed, walked over to the door and did so. When I turned back, I could see her lying on the bed like some brand new naked Christmas present. I walked back, got up on the bed and straddled her. Then I moved forward until my engorged cock was just inches from her lips. "Suck it," I said. 

She encircled the base of my shaft with her small hand, I guess to keep from choking, and took the rest of it in her mouth, sucking it and swirling her tongue around. It was so exciting watching her, I easily could have exploded into her mouth right then and there, but I had other plans. Reluctantly, I took it out after awhile and then took her by the ankles and spread her legs. "This is what you had in mind from the beginning isn't it?" I asked.

"Of course."

"Why?"

"I told you: I like older men. They're more mature."

"How many older men have you had?"

"You're the first."

"In that case, thank you." I lifted her narrow hips up a few inches from the bed and gently eased my engorged cock into her tight but wet red-bushed slit. As exciting as the act was, I did not want it to be over too soon, so I took a long, long time fucking her before I finally came deep inside of her—and could feel that she had another orgasm as well.

Eighth day: As usual, I was sitting in my chair and reading when she came into my room that afternoon. She was dressed in her usual after-school outfit of ragged and short cutoff jeans and a dark green pullover top that stopped four inches above her jeans. She did not appear to be wearing a bra and she was barefoot, so I assumed she had something in mind. She leaned against the doorjamb. "I have a question for you," she said.

"Which is?"

"Would you agree that every girl has three cherries to give away?" she asked.

"You mean like a slot machine?"

"No, I DON'T mean like a slot machine—and I don't mean like a slut machine either, so don't even suggest that. You know what I mean."

I thought about it for a minute. "I guess so."

"For most girls, it's their mouth cherry that they give away first—if you know what I mean."

"I know exactly what you mean. How old were you when you first gave it away?"

"I was young. Middle School."

"Wow. And the second one?"

"Last year. To my boyfriend."

"Which is fairly normal, I guess."

"And I want to give the third one away—just to see what it's like."

I knew she was sexually adventurous, but this was a new one. 

"But I think it may hurt more than the other two, so I want to give it to someone who would be gentle, and who would not go around bragging about it afterwards—like my boyfriend would do."

"I see. And who is this lucky person going to be?"

"Would you do it?"

"Do what?"

She sighed and rolled her eyes. "I know you want me to say it." She looked directly at me. "Would you be the first one to fuck me in the ass?"

"I would be very honored to take your last cherry. "When and where?"

"Here and now," she said. She pulled something out of the back pocket of her jeans. It was a blue tube of KY jelly. "Do you know what this is?"

"A sexual lubricant. Homosexuals use it."

"To do what?"

"To do what you want me to do to you."

"Right. I read about it in a sex column on anal intercourse."

"Thank goodness for Seventeen magazine."

"So do you want to or don't you?"

"I would love to."

"Mother won't be home from work for another three hours. We can do it in my bedroom."

"All right." I stood, and she led the way. Along the way, she pulled off her top, and I saw I had been right about her not wearing a bra. Then she unfastened her cutoffs and after pulling the tube of KY out of her pocket, she let them drop. She was not wearing any panties either. She turned naked to face me, and I could feel my erection growing.

"I guess I should be on all fours on the bed, right?"

"That would seem to be a good idea." She tossed the tube of KY to me, got up on her bed and assumed the position.

As I undressed, I realized this was going to be one of the most memorable erotic days of my life, since I had never participated in anal intercourse either.

Naked, I climbed up behind her and unscrewed the cap of the KY. "I have to confess to you that I don't have much experience in this area either, but I've read about how it should be done."

"I trust you."

I squeezed a generous amount of the KY out in my hand and applied it between the cheeks of her ass. If I had thought her pussy was small, in keeping with her size, her asshole was about the side of a dime.

"What we need to do is to widen you to make it easier," I said. "So I'm going to stick my thumb in first, and then I'll try and put two fingers in you."

"Okay."

I gently eased my thumb into her, which was not too difficult, and moved it back and forth. "Try to relax your muscle," I said.

"Okay. It feels funny," she said with a laugh.

"Of course it does if you've never done this before."

Finally, after awhile, I took my thumb out and eased my first two fingers in and began to widen her hole. She began to softly moan.

At last she was ready. I took my fingers out, lathered her up again with the KY, and gently inserted the head of my cock into her tight ass. I could feel her wince. "Hurt?" I asked.

"A little, but it also feels good. Push it in all the way."

And that's what I did, slowly but surely.

"Oh Goddddd," she moaned. 

I took that as an invitation and slowly moved it back and forth inside of her.

"More," she said, and so I did it harder and faster.

"Oh! Oh! Oh!" She began to cry out quite loudly, and I suddenly realized that I had not bolted her door. What if Ms. W came home unexpectedly and saw this, and our mutual panic I became locked into Tiffany's little asshole. "This is not what it looks like, Ms. W!" I would cry. But I doubt that she would believe me.

Still worried about the door, I came inside of her and managed to pull out my limp and dripping dick—which by the way was not easy. She collapsed on the bed, still moaning. I think she had enjoyed an orgasm as well.

So that's how it continued through the rest of her school year and into the summer, when she worked at the supermarket with her mother. She had sex with her boyfriend about once a week and with me about three times a week—or more. Needless to say, the boyfriend never knew about me.

I knew that it would be over at the end of the summer when she went away to the state university, which was about 300 miles away. Since I had been on trial at the college for the first year, and they were happy with what I did, I received a hefty pay raise at the beginning of the second year and was able to afford better accommodations—a nice rental house down by the river. Besides, I knew it was not going to be the same without Tiffany there.

But I certainly did look forward to her breaks from college when I knew I would get a visit from her—perhaps with some new tricks. For someone named 'Tiffany", she certainly was a sexual jewel.

The Landlady's Daughter Ch. 02



I have written here once before about Tiffany, who was a young lady who lived in a house where I was a tenant when I first started out as a professor at a small New England College. (See "The Landlady's Daughter" in the Mature category.) This is another story about her. 

As I had mentioned in the earlier story, Tiffany was the beautiful 18-year-old daughter of Mrs. Witherspoon, whose husband had died some time ago. In order to keep things going, Mrs. rented out an upstairs room to incoming teachers at the college until they could get settled in more permanent digs. Once I saw young Tiffany, I knew I had to have the room. I know this sounds a little like the plot of an infamous novel, but at least this girl was of legal age and in the last year of high school.

Tiffany was a petite and delicate thing of about five foot four and 105 pounds. She had strawberry blonde hair, green eyes, and her little bush was the same color as her hair. The carpet matched the drapes, in other words. If you read the first story, you'll know how I knew that.

Mrs. Witherspoon worked all day, Tiffany got home from school around 2:30, and thanks to the "friendship" that had blossomed between us, I had enjoyed having sex with her now for about three months, on an average of three—or more—times a week. She was "sexually active" to say the least, but I did manage to take the last of her three cherries (at her request.) And since we had free run of the house while her mother was at work, we did it in a number of ways and in a number of places. She was sexually adventurous and an exhibitionist to boot.

But she also came to me for advice from time to time, and this was one of those times. She entered my room, which was opposite hers on the second floor, in her usual garb of tight-fitting jeans and a thin gray T-shirt. Often at home, she did not wear a bra, and that was the situation in this case. I enjoyed looking at her good "points."

"Mr. Baxter, I need your opinion," she asked. Despite our intimacy, she still liked to call me "Mr. Baxter" rather than by my first name. I was about 20 years older than her.

"Always glad to be of help."

"What do you know about algebra?"

"Nothing."

"I was afraid of that. I'm good at English, History, Social Studies, and French. But I suck at math and chemistry."

"So did I when I was your age."

"I'm getting a passing grade in chemistry, but if I don't do better at algebra, I'm going to flunk that course."

"So what are you going to do?"

"Well, the brightest guy in the class is an exchange student from Korea named Kim Huang. I asked him if he would be willing to tutor me after school at my house. I offered to pay him for it even though I don't have much money. But he said he didn't want money, he had plenty of it, since his parents were rich. He said there was something that he didn't have which he really would like."

"And that was?"

"He didn't say. But he looked me over from my feet to the top of my head. It was pretty clear what he had in mind. He said he had never had a date with an American girl—or even a Korean girl. And by 'date', I think I know what he meant."

"Sex?"

"Yes. I don't think he's ever had any."

"A male virgin in other words. So what are you going to do?"

"Well, I don't mind offering some sex for his helping me out, It's not like I'm a virgin. But how much do you think I should offer him?"

"How much do you think?"

"Well, since he's never had it before, I wouldn't mind giving him a nice blowjob and then getting naked and doing you-know-what with him on my bed. I'm on the pill, as you know, but still I don't want to get any diseases."

"Well then, I would insist that he wear a condom. You can tell him to bring one along. That way he knows what he's going to get. You ought to have one handy too, just in case."

"Great idea. One other thing. Since my room's directly across from yours, and I like to leave the door open to circulate the air, and you usually leave your door open when you're reading, I wouldn't mind if you watched."

Knowing Tiffany, I knew that not only would she "not mind", she actually would relish the idea of my watching. Her fondness for exhibition is what first brought her to my attention.

"Don't you think he would be bothered by that?" I asked.

"I'll tell him it's ok, that you're cool." 

"Then I would love to watch. He might be a little uneasy about it—but not enough to reject your offer."

"Right. How about tomorrow then?"

"Sounds good."

Tiffany arrived home at her usual time of 2:30 accompanied by a tall and slender young man who obviously was Kim. She took him to the kitchen for a Coke, then brought him upstairs, introduced him to me, and then retired to her room, leaving her door open. I sat down to read—with a clear view into her room. 

They spent about two hours sitting on the floor beside her bed and working on algebra. Kim appeared to be quite a good and dedicated tutor.

"That's it," she finally said, standing up. "Time for me to thank you. Did you bring what I told you?"

"Yes."

"Good. You can watch me get undressed then." She crossed her arms, pulled her t-shirt over her head and tossed it on the bed. No bra as usual. Kim stared at her small but pretty breasts. 

"But what about---?"

"Don't worry about him. He never notices anything when he's reading. He won't bother us." 

Then she unbuttoned the top of her jeans, pulled down the zipper, pushed them down to her ankles, and stepped out of them. Now she was clad only in white bikini panties and white socks. With a smile, she hooked her thumbs in the waistband of her panties and slowly pushed them down, revealing her beautiful little bush. Even without being able to see his face, I realized that Kim was transfixed. He probably had never seen a naked girl before—and certainly not one this beautiful.

"You're very beautiful," he said, echoing my thoughts.

"Thank you. Now it's your turn. Undress completely and put your rubber on. We can do it on my bed."

Kim looked around once, and I ducked my head into my reading. Then he turned back and undressed...completely. I could not see the front of him of course, but I assumed his presence was appropriate. 

It must have been, since Tiffany dropped to her knees and took him into her mouth. Her talented tongue must have done its trick, since she stood after a minute or two and told him to put on the condom. He pulled it out of the pocket of his pants on the floor and did so. She took him by the hand and led him over to her bed. Then she climbed up on it, and stood up, facing me.

"Lie down facing this way," she said. "I like to be on top."

Not only on top of course but also facing my way. I knew what that was for: my pleasure and torment.

Kim was certainly not one to argue. He knew a wonderful gift when he saw it—and did what he was told.

Tiffany straddled him, sank to her knees, took his member in her two hands and slowly impaled herself on it. Then, after a few moments, she closed her eyes and slowly went up and down on it.

Kim might have been a reflective Asian, but he also was a teenager, and in less than five minutes, he groaned as he tensed and popped into the condom. I could see by her face that it was a little less than satisfying for Tiffany, but still she managed a smile. "Did you like that?" she asked.

"Yes," he groaned.

"So you feel you've been well paid for your help?"

"Yes."

"My mother might be home, soon so I guess we'd better dress, and you'd better leave."

"All right." He got up. 

"You can put the condom in my basket."

"All right." He did so and finished dressing, but she stayed naked. "Can I kiss you before I go?" he asked.

"All right."

He stepped forward and kissed her, then stepped back to admire her. "You are a beautiful girl."

"Thank you, but I guess you'd better go now."

"All right." He left the room without looking at me, went down the stairs and left by the front door. Tiffany, still naked, walked casually into my room. "Did you like that?" she asked.

"Yes, it was interesting—and quite arousing. I'm sure he'll regret later that he came so fast. He didn't have to. Your mother won't be home for another hour and a half."

"I know. But I was getting bored. It wasn't that much fun for me. I still feel like I haven't been satisfied."

"I don't know what you could do about that."

"Do you know anyone who could give me an orgasm?"

"Well, I'm a teacher. I could give you a test, and if you pass it, I would give you an orgasm as reward."

"That sounds like a good deal."

I wrote the letter "K" on a tablet beside me and held it up. "What letter is this?" I asked.

"K."

"No it's not. It's an F."

"It is not."

"Is too." I held it up again. "What do you see?"

"K."

I looked at the sign. "Why is it that every time I say 'F', you see 'K'?"

She looked at the sign a moment. "I get it. F-U-C-K. I answered it correctly. So where's my reward?"

More than an hour was left before her mother came time, and we used nearly all of that time, as I made her come three times.

End



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?"

"No."

"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?"

"Yes."

"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."

"Shit."

"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.

end