The Landladys Daughter

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.