When Grandpa Tutored Kathleen

Near the end of his life, a 77-year-old man tells his grandson a sexy story about a comely blond student of his he had deflowered when he was 18 and she was 14.

Introduction

My paternal grandfather was born in 1910. From an early age, Grandpa had a knack for arithmetic and English. Beginning when he was just 12 in 1922, he’d often make a few dollars per week by tutoring other students. Often, they were the same age he was. Not long before he passed away in 1987, Grandpa was delighted to learn that I too had become a tutor to supplement my income as an office clerk and I already had six students on my roster. He mentioned to me that tutoring could be a rewarding job—in more ways than one. He advised me, with a cheeky smile, to be on the lookout to exploit situations involving amorous female pupils.

I laughed as I tried to picture my frail, 77-year-old grandfather as a lecherous young man who was trying to bed his female students. I finally got up the nerve to ask him, “So, did you ever have a romp with a tutee, Grandpa?”

He sat back on his favorite reclining chair with a contented smile plastered on his face. Here is what he told me.

Part One

My name is Gregory Spanier. In 1928, I was an 18-year-old high school student who already had six years of tutoring under my belt. Most of the time I was recruited to teach basic arithmetic. Occasionally it was English, and, very rarely, it was another subject in the curriculum, such as geography or history. I seldom had to advertise my service once I got started. I got most of my tutees via word-of-mouth. A satisfied customer would pass my name and telephone number along to a friend, a neighbor, or a relative. About 80 percent of the time, I’d use space I’d created in the basement of my parent’s house as a tutoring area. The other 20 percent of the time, I’d go to the student’s house to conduct the lesson.

One such student who found me because her cousin had recommended my services was a true stunner, a 14-year-old girl named Kathleen McKinney. She had a head of beautiful, curly blonde hair, a pretty face, and quite a lovely figure for an eighth-grade pupil. I was more than happy to accept her as a new client. In fact, I was genuinely thrilled about it. I found out that we had once attended Middlebrook Elementary School at the same time, when I was 14 and she was 10, but I hadn’t noticed her in those days. I was noticing her now. She was that attractive!

To her credit, Kathleen always tried her best, but she wasn’t the brightest penny in the jar when it came to arithmetic. I saw that from Day One with her. I’d drill the times tables into her head, but she’d have trouble recognizing when a problem required multiplication. One problem she was assigned was the following: “There are six dinner rolls in a package. If you buy seven packages, how many dinner rolls would you have?” Kathleen immediately (and wrongly) added those two numbers together and answered, “Thirteen!” I was astonished that she had never been told how and when multiplying was very useful as a math skill. Most of our first hour-long lesson was spent just to enhance Kathleen’s skills to recognize what she had to do to solve basic arithmetic problems. When she picked up the concept, she was very pleased and flashed me a thankful smile. I thought I had made a significant breakthrough until she attempted the problem about the dinner rolls a second time. “That means there are 43 dinner rolls,” she told me. “That’s because seven times six is 43! Am I right, Gregory?” Oh, well: Rome wasn’t built in a day.

Part Two

I encouraged my students to ask a lot of questions, as that showed me what they understood and what they didn’t. Sometimes their questions drifted far afield from what they were studying. One 13-year-old boy whom I was tutoring in English wanted me to explain how the Panama Canal worked. Another math pupil asked me to define what a constitutional monarchy was. These kinds of questions certainly kept me on my toes. I always said if I didn’t know the answer off the top of my head, I’d research the question and find out.

One day Kathleen asked me one that was absolutely startling. “Gregory, how does a female get pregnant?” was her query. Despite being 14 years old and having movie-star good looks, Kathleen apparently was quite serious.

I was stunned for a few seconds, so I bought myself some time by asking Kathleen for a clarification. “Do you mean a female human?” I replied to her.

“Yes, of course, that’s what I meant,” she said sternly. “No one has ever really explained it to me. I’m getting to the age where I should know these types of things.”

I said nothing for a moment, but I couldn’t have agreed more. With Kathleen’s obvious beauty and shocking naivete, she could get herself into a lot of trouble with her lack of knowledge of basic human biology.

Kathleen explained that she came from a very religious family. “I’ve been told for as long as I can remember not to succumb to temptation. But I honestly don’t know what I’m supposed to be tempted by,” she said. Of course, there was no sexual education curriculum in public schools in 1928. Often parents avoided the subject of sexuality altogether, hoping that their children would learn all they needed to know from their peers.

When I thought about it, I don’t recall getting an official “sex talk” from my father. My most impactful sex teachers were a few vulgar sixth-grade boys, classmates of mine who seemed to be experts on this particular subject. As soon as the girls in our class started to “sprout melons” as Bruce Kramer liked to say, sex seemed to be the only topic of conversation among the boys. I don’t know if the girls had similar spokeswomen among them.

Anyway, I spent the final 15 minutes with Kathleen of what was supposed to be a lesson about how to divide fractions about something else entirely. It was a very basic birds-and-bees chat. Kathleen admitted that she had figured out that the different genitalia between boys and girls factored into pregnancy. I explained what happens to males and their sexual equipment during arousal and intercourse. This was all new to my lovely student. Kathleen discussed menstruation and said when she first got her period at age 12, her mother gave her some lessons on feminine hygiene, but nothing more than that. Kathleen insisted what I had just told her about pubescent boys and how their anatomies worked had been a great help in understanding the process!

I took a deep breath and thought the ordeal—which it had been—was over for me. The “ordeal” part had concluded, but the fun part was now on the horizon. “Can we try doing sex, Gregory?” she asked me quite sweetly. Those words sounded almost exactly like what I heard in the sixth grade from Carol Canfield whose curiosity about boys’ penises and sexual intercourse got the better of her. She thus became the first notch in my bedpost.

I looked at the clock on the wall and confirmed the time on my wristwatch. There was only about six minutes left in our tutoring session. Another student would soon follow Kathleen and might knock on the door at any time. There was no way I was going to rush through what could be an excellent fuck with beautiful Kathleen in such a pitifully short time.

“We don’t really have enough time today, Kathleen,” I stated. She looked horribly disappointed by that news. I quickly realized I hadn’t actually said yes to her sexy proposition, so I rushed to tell her, “By the way, Kathleen, I’d loved to have a screw with you. In case no one has ever said this to you, you’re absolutely gorgeous! That put the smile back on her face.

We had another math tutoring gig scheduled for the following day. We both agreed that our math lesson would be postponed and replaced by an introductory fucking lesson, with me showing her the ropes. Of course, no one else would know about this change of plans. Fortunately, my parents were out of town, visiting my father’s sister 30 miles away, so I had the whole house to myself. We still had about four minutes left in today’s session, so I suggested a “sneak preview” of what would happen tomorrow.

“What do you mean by that, Gregory?” she asked me.

I leaned forward and kissed her on the lips—which she really liked. She moved closer to me so we could embrace while our kissing increased in intensity.

“I don’t have much experience in kissing boys, either,” Kathleen confessed. “But I like it very much. You are very good at it, Gregory!”

I chuckled and said, “Thanks for the compliment, Kathleen.” I surprised her by quickly squeezing her left breast with my right hand. She gave me a quizzical look.

“I couldn’t resist, Kathleen,” I told her honestly. “Most guys are horny devils. We’re wired that way. I needed that sneak preview to get me ready for tomorrow afternoon with you. Your breast felt lovely, my dear, during that brief grope. I can hardly wait for a full hour of sex with you tomorrow.”

Part Two

Never had time moved so slowly in my life as it did between the end of Friday’s math tutoring with Kathleen and our scheduled Saturday screwing session. Before Kathleen arrived, I made a point of bathing, putting on fresh clothing, and dabbing a few drops of manly cologne on various parts of my body. I hoped Kathleen would approve of the pleasant scent. I started looking out the window about 15 minutes before Kathleen typically arrived. She always walked to her sessions, even in rainy weather, as she lived just three blocks away from me. To my delight, she was 10 minutes early. I could hardly contain my excitement. I didn’t give her a chance to knock on the door. I opened it for her when she was still two houses away.

Kathleen, too, had made an effort to be as physically appealing as possible. She was wearing a frilly blouse that was mostly white, but it did have just a tinge of mauve to it. A black pleated skirt, long white stockings, and shiny black dress shoes completed Kathleen’s ensemble. She looked like she could have been on her way to a church function. She was utterly scrumptious to me! Of course, even if Kathleen had arrived clad in a burlap sack, she would have been a sexy sight for my eyes.

“I’m glad you arrived early, Kathleen,” I commented. “Now we have 70 minutes for sex instead of just 60.”

“I figured the same thing, too, Gregory. I want to start as soon as possible,” she noted. “This will be a great learning experience for me, I’m sure!”

“One thing’s for certain,” I began, “this will be the greatest teaching experience in my life so far. Nothing else comes even close.”

There was a small bedroom designed for houseguests that was adjacent to the area in my home where I did my tutoring. I suggested that ought to be the place we should go for this special biology lesson. Kathleen quickly agreed. I also suggested we continue kissing for a minute or two—enjoying the same type of romantic busses that we had shared the day before. We did this while we sit together on the bed.
“Even better than yesterday!” Kathleen declared happily.

I smiled at her then I said, “This is going to be very enjoyable for both of us, Kathleen, but I’m still going to treat it as a lesson.” I stood up and said, “I’m going to show you my dick now. The proper name for it is penis, but there is no shortage of nicknames for it.”

I pulled down my freshly pressed trousers and then my briefs. I already had a partial erection which sprang to life once it was freed from the confines of my underwear. I noticed that Kathleen was utterly transfixed by it.

“This is the first time I’ve ever seen a male private part,” she told me. “I have no brothers, and my father is very careful about being suitably dressed when he wanders around our house.” Then Kathleen refocused on my weapon and asked me a specific question “Is it a normal size?”

“I think so,” I replied. “I haven’t gotten any complaints so far. I’m going to play with it so it gets longer and harder. Watch me and learn, Kathleen!”

It was very arousing for me, just standing with my drawers down in front of the prettiest 14-year-old girl I had ever seen. As I had promised, my penis got longer and harder in a matter of seconds. I still put on a bit of a show for Kathleen’s benefit, though. I continued to yank on it and play with my testicles until Kathleen said something I hoped I’d hear: “Can I play with it now, Gregory?”

“Absolutely!” I responded as I stepped even closer to her. She was still sitting on the bed as I placed my aroused manhood a couple of inches from her face. I felt my shaft grow even larger. Kathleen tentatively raised her right hand.

“Go on, Kathleen,” I instructed her. “Touch it. Play with it. Jerk it. Fondle it. Caress it. It’s all for you. You would give me great pleasure by doing any of those things with my dick. The great thing about sex is that we can please each other while we please ourselves.”

Kathleen was persuaded to touch it. She rubbed her right index finger against it for about three seconds. Her smile told me she liked how it felt. “Slowly tug on it,” I told her. “That would feel wonderful!”

Kathleen caught on very quickly. Then she became cutely creative, switching hands every couple of yanks. I made a further suggestion. “Kathleen, you can occupy both your hands by tugging on my shaft with one hand and playing with my testicles with the other. That always feels heavenly to me!” She complied—and the feeling was tremendous.

I had never received oral sex in my life, but I figured this was the optimal opportunity to try for it. “You can lick it, if you like, Kathleen,” I noted.

She glanced up at me. I told her to pretend my rod was a lollipop. I added, “You don’t have to do it if you don’t want to do it, Kathleen. It’s entirely up to you, honey.”

“I want to learn, Gregory. That’s why I’m here. I’ll give it a try.”

That brief statement was music to my ears. Kathleen placed my penis by her lips and began to lick it thoroughly, both upward and downward. This was superb!

“Lick the top of it, too! It’s the most sensitive part!” I requested—and she merrily obliged. “Now put the whole thing into your mouth as far as you can. That’s a sexy sight.” She was talented at that, too. I saw that my balls were almost resting on her chin.

“How am I doing?” she asked me after she temporarily removed my dick from her mouth. She was eager to find out.

I grinned and said, “Let’s put it this way, Kathleen: If I were an eighth-grade boy in your class, I would have shot my load about two minutes ago! You are doing a superb job. I think it’s time for me to please you now.”

I took off my shirt to be completely nude while Kathleen began undressing. She stood up and removed her frilly blouse. Kathleen was wearing a brassiere—which was a fairly new clothes item for females in 1928. She definitely needed to wear one because she was quite busty for her age. She released the clasp and unceremoniously dropped her bra to the hardwood floor. Her sensual mounds jiggled slightly before coming to rest.

“My god, Kathleen! Those are the best pair of breasts I’ve ever seen in my whole life!” I told her. I wasn’t joking. “Stop there so I can caress them and make you feel good.” Of course, I was actually more interested in making myself feel good.

I sat down beside Kathleen at the edge of the small bed. I wrapped my arms around her so I could cup her highly desirable goodies. They were magnificent objects. After only the slightest of touches, her nipples became hard. Kathleen’s reaction was to utter a cute, girlish giggle. After a suitable time employing only my hands, I involved my mouth. I leaned toward her and started to suck on her right breast. More giggling ensued. “I’m glad I’m amusing you, Kathleen. I guess it’s better than displeasing you.”

I pushed Kathleen down to the bed, so she was lying on her back. I continued to grope both her tits simultaneously while moving left to right to suck on each one thoroughly.

I wanted to do a sex act I had never done before with any girl, but I had heard about it from various buddies who highly recommended it: I wanted to fuck Kathleen’s tits! I explained my desire. Kathleen just shrugged her shoulders and said it was okay with her. I straddled her, laid my penis between her boobs, squeezed them together, and then I slid my dick up and down. Kathleen seemed transfixed by what I was doing. She started laughing when one of my amorous thrusts struck the underside of her chin. “Okay, I’ve had my fair share of fun. Let’s get back to me sexually pleasing you, Kathleen!” I said.

I sat on the bed, and I assisted Kathleen in removing her shoes, socks and skirt. She stood up in front of me to drop her panties. Like I had done to her, she placed her important body part a few inches from my face. Her pussy was hairy but nevertheless beautiful. I immediately started to lick it and finger it. “Lie on the bed, Kathleen,” I told her, “It will be more relaxing for you!” She took my advice—and she was very glad she did.

I discovered that pretty, sexually inexperienced, Kathleen McKinney was a screamer and a squirter. As soon as I began stimulating her vagina with my tongue or hands, she squirmed on the bed in ecstasy. She became very wet in a hurry and actually ejaculated a blast of liquid from her pussy.

“Sorry, Gregory!” she apologized. “I don’t know what came over me!”

“I do!” I said. “You had an orgasm—which is never anything to apologize for.”

Without further ado. I mounted Kathleen, pushed her thighs slightly apart, and rammed my stiff dick inside her wet hole. She was tight, so what a marvelous sensation that was!

Kathleen had an epiphany. “Now I totally understand how babies are made, Gregory!” she announced as I was drilling her. “Everything sexual we did before this was basically just for fun, right?”

“Yes, that’s right, Kathleen. It’s called foreplay,” I told her. “It’s done to get both people’s bodies prepared for intercourse. I hope that was the case for you today, honey.”

Riding Kathleen was the best thing that had happened to me in my 18 years. We had meshed quite well! I knew I was pleasing her with my erection while Kathleen’s virginal vagina was pleasing me.
I knew an ejaculation would soon be coming. “Do you want me to make a baby with you, Kathleen?” I asked her that question in the most gentleman way I could, considering she was deeply impaled on my stiff rod.
“No, I don’t want to be a mother!” Kathleen declared firmly. “At least not now. I haven’t even started high school, yet.”

That was the answer I had expected. “Okay,” I responded, “I’ll pull out and come all over your sexy tits. A few seconds later I did just that. Several ropes of white goo hit their intended target. Kathleen even helped me by grabbing my shaft for the last shot and aiming it for me.

I was panting heavily, but I still managed to summarize what had just occurred, “That’s your sex lesson, Kathleen, on how not to make a baby. If you ever want to actually make a baby, just give me a call. I’d be more than happy to cooperate!” We hugged and kissed for the next 20 minutes. I told her I had no other plans for the day and she was welcome to stay, but Kathleen said they had some sort of church activity to attend. “That’s why I was dressed so nicely when I arrived here!” she explained. I laughed at being the secondary attraction to a children’s choir from Austria.

Three days later, when Kathleen arrived for math tutoring, I quietly asked her if she had told her parents about what we had done so passionately 72 hours earlier.

“Of course I kept quiet, Gregory” she informed me. “My parents will never know about it. However, I do have a younger sister who is 12 years old. Her name is Debbie. I told her what we did. She was fascinated. Furthermore, Debbie wants you to give her a sex lesson when she’s 14. Gregory, can you pencil her in for two years from today?”