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Sext Messaging Ch. 01

By: Baxter72



After I retired as a professor of English at a small New England college where I had worked for many years, I occasionally made some extra money by working as a substitute teacher at the local high school. But basically, I hated it. About 20% of the students were actually eager to learn and worth teaching, 50% didn't care one way or the other, and 30% would go out of their way to make your life as unpleasant as possible.

One year, I accepted a long-term sub position as an English teacher because the former teacher had given birth to her first child and wanted to take 6-9 months off to be with the baby. It turned out to be nine months, so I taught several classes for virtually the whole school year.

Interestingly enough, among the 20% it was a pleasure to teach, nearly 75% of them were girls. That shows you how much the world has changed in recent years. Girls are taking over. 

The student who it was the greatest pleasure to teach had the odd name of Christmas Cross, since she had been born on Christmas. She hated her first name and instead called herself "Crissy." She was very bright and an eager student, but two of the reasons I liked her so well were that she obviously liked me as a teacher—and she was strikingly beautiful: about five-foot-seven with long straight blonde hair, a beautiful and delicate figure, and a face and smile that would melt an iceberg. And pale blue eyes. 

It probably was for that reason that as we neared the end of her senior year, and I knew she was going away to Boston U, I told her she could seek my help at any time with essays that she might have to do there, and I gave her my personal home e-mail address. Little did I know how she was going to use it.

She entered Boston U in September of that year, and by the first of October I had an e-mail from her. What follows is an account of the e-mail exchanges we had over the next 2-3 months.

"Hi! Remember me?" she wrote. "I hope you meant what you said about taking a look at some of my essays and offering your suggestions, because I would like to take advantage of that if you have the time. Here's the first one. It was for English Composition, and the assignment was "The Most Embarrassing Thing I Ever Did." I thought you would get a kick out of it since it involves you. Crissy"

I wondered how it could involve me? I found out when I read it. In her ten-page essay, she confessed to having had a crush on her English teacher all of her senior year. The teacher obviously was me. She even admitted to having sex dreams about him and actually confessed to thinking about him when she masturbated at night in her bed! I certainly hoped this English prof at Boston U was a woman and not a man. I hate to think what might develop if it was a man. Finally, she confessed that in an effort to get that teacher to think about her sexually, she had gone to class wearing a relatively short yellow-and-brown tartan wool skirt with no panties underneath. Since she was sitting in one of those chairs with a wrap-around platform to write on but otherwise nothing in front—and since she was sitting in the first row—halfway through the class, when the teacher was sitting at his desk in front of her, and all of the other students were busy taking a test, she slowly slid the skirt up on her thighs and parted her legs. She knew that the teacher but no one else could get a clear view up her skirt. She even admitted to having brushed her pubic hair the night before with hydrogen peroxide to make it even more blonde. But the teacher never even noticed! She felt humiliated. 

And that was her "most embarrassing experience."

It took me awhile to calm down, but finally I made some suggestions about her essay and tried to pen some detached and objective comment back to her.

"I'm really surprised that you would show me this," I wrote. "I had no idea you felt that way about me, and yes—I never noticed, and that's just as well. But I certainly admire your ingenuity—and your nerve."

She sent a reply back the following day.

"I was a virgin at that time—which I am not now, thanks to my boyfriend, Larry—but I used to masturbate every night and imagine you doing the most outrageous things to me."

"And the most illegal things if they had been real," I responded. "You were not eighteen at that time."

"But I am now. Listen, I'm going to set up a chat line just between us, so we don't have to keep mailing back and forth, and no one else will see it. Is that okay?"

"Sure. What do you need from me?"

"Nothing. I know how to do it."

So the rest of what follows was in back-and-forth chat. 

"How often have you done it—with this Larry?" I asked her.

"Three times, and I hated it the first time, it really hurt. But it got better the next two times, and I began to enjoy it. But I dropped him after he started calling me his 'little fuck bunny'—and I think he told other people about it."

"That was a wise move on your part. You're too good for him."

"I know. I agree. So I'm back to thinking about you when I masturbate every night."

"Are you crazy? I'm old enough to be your grandfather."

"So what? I like older men."

"Have you ever had any?"

"No, but the idea sounds appealing."

"You shouldn't tell me that."

"Why? There's nothing wrong with it. It's not illegal. Haven't you ever had any sex fantasies about your students?"

"No comment."

"Tell me."

"All right, probably every teacher, male and female, has had at some point or another."

"Did you ever have one about me?"

"No comment."

"Tell me!"

"Is anyone but you able to see this?"

"No, I'm the only one." 

"You guarantee that?"

"Yes, of course."

"All right, I'll tell you then. You're so pretty that I've had more than one sex fantasy about you. I've had a number in fact. My favorite one is when you come to my classroom after school, and even though you were an 'A' student, in my fantasy you tell me you will do ANYTHING if I will just raise your grade. I ask you what you mean by 'anything'—and you proceed to show me."

"What do I do?"

"First of all, you take off all your clothes, and then you get down on your knees and provide me with oral sex. Then you shove everything off my desk, lie back on it, and we proceed to have sex."

"After I give you a blowjob, we fuck—in other words."

Yes...we fuck."

"I'll write you again tomorrow."

"Where are you going?"

"I have to masturbate. Bye."

And she was gone. But that night I did the same thing.

"Did you masturbate last night, thinking of me?" she asked the next night.

"Yes."

"Will you do it again if I talk dirty to you? I will too, at the same time. I'm sitting here completely naked. You can imagine it—or I'll send you an actual picture from my digital camera if you want. I can print it right in my room, on my printer."

My God, what was I getting into? "Send me a picture," I said. "Send me several."

"All right. I have your address. Are you naked?"

"No."

"Can you at least take it out?"

"All right—it's out."

"Good. I'll bet it's very pretty."

I laughed. "You're the first woman who has ever said that."

"I wish I could see it. Do you have a digital camera?

"No, sorry."

"Rats. Know what I would like to do to you?"

"No. What?"

"I would like to suck your cock so hard it would squirt out my ears."

Oh God. I didn't think I could stand anymore of this. But I had to match her. "Know what I would like to do to you?"

"No. What?"

"I would like to fuck you so hard that you couldn't sit down for a week."

"I would like that."

"Okay," she wrote in a scholarly dignified voice. "Now it's time for us to get serious. School is closed for Thanksgiving from November 27th until the 31st. Naturally, my parents want me to come home, but I don't want to go there. The whole family gathers then, and since they all hate each other, it turns into one big drunken verbal brawl. So I've told them I'm going to stay in Boston to work on my term paper. But you're off then too, aren't you?"

"Yes."

"Why don't you come down to Boston and join me?"

"Why?"

"Guess."

"In your dorm?"

"No, silly, I would be the only one there, but even still I wouldn't trust it for privacy. But if you would spring for a nice hotel room for a couple of nights, we could spend a little time together. I'm sure I could make it worth your while—even though I might not be able to sit down for a week." 

I thought about it. I was never going to get a chance like this again. An 18-year-old girl offering herself to a 62-year-old man. "All right, I'll do it. I e-mail you back when I have the hotel."

"Good. Are you going to think about me tonight?"

"Of course."

"Good, because since I'm already naked, I wouldn't want to waste it. So I will be thinking of you...while I masturbate."

And she was gone.

Be Continued...

Sext Messaging Ch. 02



Crissy, my favorite student when I was a substitute English teacher at a New England high school, was now in her first year at Boston University. At her instigation, we had started first an e-mail exchange, then an exclusive chat site just between her and me. As it progressed, the chat site grew hotter and hotter, as indicated in part one, as a result of the crush she had on me in her senior year of high school. I was not aware of the crush, but she certainly was making me aware of it now with a lot of chat mail "dirty talk." She also had invited me to visit her in Boston during her Thanksgiving break and as an inducement had promised to send me some pictures of herself that she could take in the privacy of her dorm room with her digital camera. 

The pictures arrived in the mail. All of them were 4 x 6 and of course in color. They were very nice, just the sort of thing you would send to your favorite teacher. In the first one, she was standing at the end of her dorm room with her back to the camera and looking through the blinds of her window. She was completely naked, and had the cutest little bottom I had ever seen.

In the second, she was turned around and acting as if she had just been discovered naked. Her mouth was open, her face looked shocked, and her hands were clutching her private area, although her two pretty little breasts were exposed. She had pink nipples about the size of quarters.

In the third picture, she was standing facing the camera with a smile on her face, and her hands on top of her head, fully exposed, naked. Maybe I was prejudiced, but she had the cutest little blonde bush I had ever seen.

In the fourth picture, she was lying in her dorm bed, again naked with a smile on her face, and with her legs separated a little, as if she was ready for sex.

That was all I needed. I called the Copley Hotel in Boston and made a reservation for the three nights of Thanksgiving holiday. I couldn't believe what it was going to cost me, but I suspected it would be worth it.

"I got us a room at the Copley for three nights," I said to Crissy in our next chat exchange.

"Wow, you like to spend money. I hope you won't be disappointed."

"I'm sure I won't be. I'm going to get the bus down rather than drive, so I'll arrive there around noon. Why don't you come sometime in the afternoon and call my room, and I'll give you the number. They won't give you my room number at the desk. Security you know."

"All right. I'll just tell them I'm your granddaughter."

I sighed. "Good idea."

Despite my age, I was in pretty good shape and not at all overweight, thanks to daily workouts after school at the gym. But even still—a 62-year-old man and an 18-year-old girl? Wow! This was Faust's dream—with my own personal Marguerite. A few days before I left, I also took the extra precaution of visiting my doctor and asking for some samples of Viagra, since I knew that all doctors now had them. He knew that I was not married, so he probably assumed that I was having an affair with some other teacher. If he only knew! 

The room at the Copley was beautiful and had a lovely view of the city. It should have had for the price I was paying for it. But I had the feeling I would not regret it. I ordered up a good bottle of champagne in an ice bucket

At 2 p.m., the phone rang. It was Crissy. I gave her the room number and awaited her arrival.

"It's room service, sir," she said as she knocked on the door. "Are you the one who ordered the sex?"

I quickly opened the door and pulled her inside. "It's a good thing you had the right room and that there was no one in the hallway." I said. She was dressed in the usual student garb of designer jeans and a gray sweatshirt with "Boston University" imprinted on it. She was carrying a small overnight suitcase.

"Ignore the way I'm dressed," she said. "This is just traveling clothes. I have a nice dress with me if we go out to dinner—and something special that I think you would like."

"Fine. Would you like a glass of champagne?"

"I would love a glass of champagne. I would also like a kiss."

That was fine with me. I leaned over a kissed her, first on the cheek, then full on the lips. She wrapped her arms about my neck, pressed her body against mine, and that long and lingering kiss turned into one of the most erotic things that had ever happened to me. I could feel myself getting the beginning of an erection already. 

"Wow!" I said.

"I've been wanting to do that for a long time." 

I went over to the table, twisted open the champagne bottle—"pop!"—poured her a glass and handed it to her.

"To us," she said raising her glass. 

"To us."

She drank it down in one gulp. "And now I would like to take a shower and change clothes. I have a surprise for you."

"Okay, over there," I said, pointing to the bathroom.

She looked around the room. "This is a beautiful room, and the view must be great at night. You must have paid a fortune for it for three days."

"I'm sure it will be worth every penny."

"I hope you won't be disappointed. I'm new at this."

"I'm sure you'll do just fine."

She carried her overnight bag into the bathroom.

Twenty minutes later, she emerged. She was right: I was surprised. As a senior, she had been captain of the cheerleading squad—and had apparently kept her uniform: A gray sweater with a maroon "M" in the center, a short pleated maroon-and-gray skirt, gray wool socks, and white tennis shoes.

"Wow!" I said.

"Like it?"

"I love it."

"Haven't you always wanted to do it with a high school cheerleader?"

"Every male wants to do that."

"Here's your chance. What do you want to do first?"

"I want to do what any male would want to do: I want to undress you."

"Be my guest."

I walked over to her, kissed her again, took the bottom edge of her sweater and pulled it over her head. She was wearing a white bra, which looked brand new. I suddenly thought of the windows and looked around. Since this was a corner room, there were windows on two sides, all of them with the drapes pulled open so we could enjoy the view. But also right across the way were other hotels and offices. 

"Should I pull the drapes?" I asked.

"No, I don't care if anyone sees us. We're not doing anything illegal. You could be my grandfather for all they know."

"Oh great: a little public incest."

"Incest is best, you know."

"Where did you hear that?"

"I just made it up."

What a little pervert, I thought. 

"Turn around." She did so. I unfastened her bra, pulled it from her shoulders and tossed it on a chair. Then I unfastened the button at the back of her skirt, pulled the zipper down and let the skirt fall at her feet. She was wearing white cotton panties with blue bunnies on them. I got down on my knees. "Turn back this way." She did so. I took the elastic of her panties and slowly pulled them down over her thighs and her knees until they were draped at her feet. Her beautiful little golden muff was right in front of me. The hair seemed to be trimmed to about an inch, and her nether lips were covered with a light down. It smelled like the shower she had just taken, and it looked good enough to eat, so I leaned over and licked her lips. They were delicious.

"You're getting me so excited my legs are beginning to shake," she said.

"Then go lie down on the bed," I said, "I have another request."

"Okay." She ran across the room and jumped on the bed. Then she kicked off her tennis shoes and flopped down face up with her head on the pillow. Smiling at me, she spread her legs a little. What a view.

"You said you used to think about me when you masturbated."

"Yes."

"I've never seen a girl masturbate. I want you to do that now. I want to watch you while you come." 

"All right." She put her slender forefinger between her nether lips and began moving it up and down. I looked over at the windows. I could not see anyone watching, but I was sure that someone—or more than one someone—was. What a treat for them. I pulled a chair up to the end of the bed.

She closer her eyes and began murmuring: "Mmmmmm." Just watching her was giving me the biggest hardon, so I unzipped and took it out.

It did not take her long. In about ten minutes, she was trembling and moaning. "Ohhhhh, ohhhhh, ohhhh." And finally, with a little squeal, she came. It was quite apparent, since her face turned red but certainly not from embarrassment. She laid there for awhile with her finger still in her muff. Finally, she opened her eyes and looked over.

"How was that?" she asked.

"That was the most exciting thing I have ever seen."

She looked at my erection. "I can see that. I don't think you have to worry about being able to perform at your age. Are you going to get undressed?"

"I can't even stand. Why don't you come over here?"

"All right." She slid out of bed and walked over.

"Get down on your knees," I said. She did so. "I want you to perform oral sex on me."

"I will if you don't put it in such clinical terms," she said.

"I want you to suck my cock. I want to come in your mouth."

"Okay." She leaned forward, put her hand around it, and took it in her mouth. She may have been new at this, but she certainly had learned fast. She swirled her tongue around it as she sucked, and like some horny teenager, I came in her mouth in less than ten minutes. She swallowed all of it but a little rivlet running down her chin. "Yum, yum," she said.

"Now get back in that bed. I want to do the same for you, and I want you to come in my mouth."

"Okay!" She jumped to her feet, ran over to the bed, jumped up on it, flopped down on her back and spread her legs. I got up, took off my pants, underwear, and shirt and walked over.

"You look nice for a man your age," she said.

"Thank you. You in turn are the most beautiful thing I have ever seen."

"And yet you're going to pluck my innocence."

Yes, I'm definitely going to pluck you." I got up on the bed, knelt between her thighs, and bent down. I could tell from the first taste that she was still very juicy. She tasted quite good—like a young girl should.

But like me, she couldn't keep it going for very long. She began moaning and kneading her breasts, and again, in less than ten minutes, with a loud cry, she came. 

"You're the first person who's ever done that to me," she said as she propped herself up on the pillow. "Larry thinks it's unmanly, but it's okay if I do it to him."

"He doesn't know what he's missing."

"We have three days here. Will you do it some more?"

"Of course." I got up on my knees. "And now I'm afraid I'm going to have to fuck you. You leave me no choice."

She slapped her hands to her cheeks in mock horror. "Oh no, mister! I'll be good! I promise!"

"You've already been too good. That's the problem." I grabbed her by the sides of her narrow hips, lifted her up for a better position and shoved my engorged member into her. 

"Ahhh!" she cried.

But this time I wanted to make it last as long as possible. As she wrapped her legs around me, I went in and out of her as slowly as I could. But even then, I could not make it last very long. After 15 minutes, I came in her with a groan, and I'm pretty sure from her moans that she came at the same time. But it was hard to tell since she was already so hot and wet. I suddenly realized that no one had mentioned the word "condom", but it did not matter since I had a vasectomy 15 years ago.

Finally, I pulled out of her and fell back on the bed beside her.

"Wow," she murmured.

"I agree."

She turned to face me. "You're all wet. Would you like me to clean you off?"

"I would love that, but crawl over me and do it on the other side, so if anyone is watching, they can get a better view."

"Okay." She climbed over me, lifted up my wet penis and put it in her mouth. And yes, ten minutes later, I came again in her mouth.

And that's the way it went for the next 72 hours. We went out to dinner at Union Square. We came back and had sex, then went to sleep. Got up, ordered room service breakfast, went out, took a carriage ride through the park, during which she gave me a blowjob, came back, ordered room service dinner, after which, she stood naked, facing the window while I fucked her from behind—and so on. 

Originally, I had thought this was going to be a one-time thing. But at her invitation, I found reason to go down to Boston for at least an overnighter once a month.

It may sound from this story that I am a bit of a sexist, but that is not true. I have always believed in the education of your women.

Especially if they are pretty and naked.

End