Wednesday Serial – Miss McCaffrey Conclusion


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.



As the summer closed around us that year we had explored a couple of other ‘literary themes’. She left an indelible mark upon my heart. I helped her pack as she was she was heading north to New England.


I didn’t quite understand it at the time but think differently of it now. She told me she was going on to further her own studies. She was returning home to a place she’d never been before, she called it the Ipswich project.  I got ready to head off to New York University that fall.


I recall this event from my youth now as I believe it was instrumental in my decision to go to college and expand my horizons. I furthered my studies of literature exploring many new themes and, graduating, became an English teacher myself. But I suppose in my heart what really sparked this memory, besides having reread some Nabokov this summer, I’m looking forward to having this exceptional student Elizabeth in my American lit class this year.

Wednesday Serial – Miss McCaffrey pt 10


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.



Tuesday couldn’t arrive fast enough. Miss McCaffrey and I were going to the Metropolitan Museum of Art down in the city. I was looking forward to the adventure. I had only been to the city a couple of times before, and always with my parents. Since Miss McCaffrey and my mom were well acquainted, my folks had no reservations about my going along.


It turned out to be a wonderful day. We spent most of the day going through exhibits. She’s the loveliest tour guide. Then, after dinner, we went for a walk through central park. She took .y arm as we strolled. It was a nice warm evening and we were in no rush. I called my mom and let her know we word be taking a late train back and I had my keys. It was after midnight when we got back to grand central station.


“This has been an excellent field trip,” I told her while we caught the last train out to Port Jefferson, “You know so much about so much.”


“And you are learning a lot about a lot Jeremy.” She completed back. “And have you finished ‘Fear of Flying’ yet?”


“Yes,” I replied. “I even read the good parts twice,” and then it dawned on me,  that novel had a very lurid sex scene on a train.


With a sparsely populated late night train we were undisturbed while necking in our seats at the end of the rear car. Shortly after the Huntington station, Miss McCaffrey unbuttoned the fly on my Levis. She already knew that I didn’t wear underwear when I wore jeans. I was about to find out that she wasn’t wearing anything under her dress.


“Let’s see how well you recall that scene.” She said, lowering herself onto me. The motion of the train amplifying her motion.


We both enjoyed each other in the privacy of the deserted car on that late night ride.



Wednesday Serial – Miss McCaffrey pt 9


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.



As my senior year came to an end my thoughts were of Miss McCaffrey and our time spent tutoring me. It was the most educating summer I have had before or since. She really took her time with me. Quality time, as she explained it, was the quality of our time together we focused on.  


She had to commit time to her master’s degree program, taking courses over the summer. My summer job with the town parks department occupied a good deal of my day. But I did look forward to the time I spent with my ‘ summer reading list’. 


I was currently working my way through ‘Fear of Flying’ and not finding it too difficult. I was work on reading empathically. Reading the story in such a way as to understand the story from the perspective of the characters involved in the story. This was giving me a great deal of insight. As I came to the end, it was time to see my tutor. 


Miss McCaffrey greeted me warmly. I had missed her these past two weeks. She felt so comfortable in my arms. I could feel her warmth and vibrancy through her kiss. Just being with her excited me. 


“Well Jeremy,” she said with that twinkle in her eye “we are going on a field trip!” 


“Wow! Really?” I gushed with enthusiasm. I was excited about going just about anywhere.  


“Yes young man,” she said “it’s time to expose yourself to art. But first…” her hand snaked its way into my jeans. 



Wednesday Serial – Miss McCaffrey pt 8


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.


With the afternoon’s lesson well finished, and the sun streaming through the light drapes, I was so taken with how radiant Miss McCaffrey looked. Her porcelain skin glows, and she has this sly yet contented smile. As she is looking up at me with her large, sleepy eyes I realize that

‘I don’t want school to end next week,” I said to her, seeing myself reflected in those doe eyes of hers. “No, I don’t want it to ever end ever again. No! No more summers. This is it… ”

Lying in her bed feeling her warm body next to mine, I wanted time itself to stop. But, I’m just a boy and time marches on.  Miss McCaffrey gave me a kiss as she got up and out of the bed. Stretching in the summer sunlight she looked like an angel. I was smitten.

“That is a wonderful thought, for now at least, but tempus fugit,” she said bending over to kiss me.

“That might be, but I don’t have to like it, I just don’t want to lose you.” She was my first. You never want your first to end. As I watched her leave the bedroom. I stretched out and enjoyed the comfort of the cool sheets.

I lay there and reflected on that for a while. My English teacher was my first, but it occurred to me that I was not her first. That she already had a first, and probably a second. All I could think about was not seeing her in class anymore. These past couple of weeks had been wonderful. I was so busy trying to figure out what crazy scheme I could use to keep seeing her that I hadn’t noticed her return from the shower. She came in wearing a short, silk robe and sat at her vanity.

“I’m thinking that I could help you out here, doing chores and such,” I suggested to Miss McCaffrey.

“Dear, sweet, Jeremy, you are going to be too busy for chores,” she said with that ‘teacher’ look of hers, “I’m compiling your summer reading list.”



Wednesday Serial – Miss McCaffrey pt 7


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.


The next day I arrived right on time. Miss McCaffrey greeted me at the door wearing a long black silk robe. Grabbing my hand as she opened the door she pulled me inside and kissed me deeply, wrapping her arms around me.

As she felt my erection growing in my jeans she instructed me to go to the bedroom, strip, and prepare for some tutoring. She would be along shortly as she wanted to put herself together first. There was a hint of mischief in her voice.

I went up to her bedroom as instructed. I drew the drapes closed to dim the room, stripped down, and stretched out on the fresh sheets. The anticipation was building in me. After about ten minutes of lying there imagining that lush body of my gorgeous English teacher, I heard her approaching the bedroom door.

Miss McCaffrey opened the door and strode in. She came over and stood at the foot of the bed. I was quite taken aback at the transformation she had undergone. She stood there smiling slyly.

“Don’t think me bad lover, no don’t think of me as wicked” she recited in a breathy tone. The words were familiar to me. It’s what Catherine said to David in the piece by Hemmingway

I recognized the bright blue playful eyes behind the round black glasses, and the curly black hair that spilled out from under the black Fedora she wore. Yes, it was Miss McCaffrey. She wore a navy blue suit jacket with matching waistcoat, crisp white French-cuff shirt with gold cufflinks, a red paisley tie. She had on a pair of navy suit pants tailored flatteringly to her curves. Every inch of her was transformed into a well-dressed gentleman.

She tossed her hat and let her hair down. Then she took off the jacket and joined me on the bed. As I kissed her warm lips I slowly undid her tie, then the vest. As I started working on the buttons of her shirt, I followed along, my lips kissing a trail down her neck to her chest.

I figured out that the assignment was to re-enact one of the scenes from ‘Garden of Eden’. I hope she grades on the curve!

Wednesday Serial – Miss McCaffrey pt 6


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.


The following Monday back at school as the last bell of the day rang and all the students were hustling their way out Miss McCaffrey called out “Jeremy, would you mind stopping by my desk I have a new assignment for you.”


“I wanted to give you the option of continuing with the Hemmingway theme, or would you prefer that I give you something more contemporary and less challenging?”


“Well, if you wouldn’t mind” I replied “I would prefer to work on the Hemingway piece again. I don’t want to duck a challenge.”


“Wonderful!” Miss McCaffrey smiled a smile of satisfaction. She seemed pleased that I wanted to maintain a higher level of performance. What I couldn’t know was that she was looking forward to a higher level of performance from herself as well.


Things at school were going smoothly through the next two weeks and I was pouring himself into the ‘themes in literature’ project. I was not looking forward to school ending for the summer next week.


The passages from Hemingway’s Garden of Eden were becoming s bit more clear for the most part. But where the passages were delving into the woman’s exploration of masculinity, I was less clear. When Friday rolled around, I waited until after the rest of the class had filed out before going up to Miss McCaffrey’s desk.


She was sitting there in a powder blue silk top, her curves so nicely highlighted. I was glad that I still had that spiral notebook to hide behind. Her smile lite me up inside and I found himself having trouble explaining that I was having some trouble explaining things. On the project that’s is.


“Don’t worry about having trouble with that particular theme. I was rather expecting that you might,” she said getting to her feet. She put her hand on my chest and said “that’s what teacher are for, to help. Come over tomorrow around noon and I’ll arrange a little tutoring”


“Yes Miss McCaffrey,” I said with a smirk “I’ll be there.” As I turned to head out she gave my ass a swat.


“Brat!” she retorted smiling “and I don’t think you’ll be needing that notebook.”




Wednesday Serial – Miss McCaffrey pt 5


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going. Now we are there.


As soon as we entered my English teacher’s bedroom she spun me about, stripped off my t shirt, and pulled me tightly to her lips again. Her breasts were pressed firmly against my bare chest. My hands worked her dress off her shoulders and on to the floor. I had caught on, as her hands deftly worked the buttons on my jeans, that we would not be needing costumes for the remainder of this class.



With a firm pressure on my shoulders Miss McCaffrey shoved me onto the king sized bed. Then she slipped my jeans off to join her discarded dress. “I think it’s time for phase two,” she said with a grin on her luscious lips.


As I worked my way up towards the head of the bed she was crawling up towards me. Stalking me like a tigress, pursuing me. Then she drew herself up and straddled me looking down, with lust heavy in her eyes. I grabbed hold of her soft smooth silky thighs. My confidence was growing, fueled by my own new found lust.


Miss McCaffrey lowered herself into me and I could feel myself crossing over that threshold to manhood. As she ran her hands through her hair, I looked up longingly at the firm breasts towering over me. I brought his lips up to sample the offered flesh.


The rest of the afternoon was spent with me learning many ‘ variation on a theme’. I was exploring all of Miss McCaffrey. I started understanding more of the passages I had been assigned to read these past couple of months. Her arms and legs, her breasts and lips, I was coming to learn and understand many new sensations.



Wednesday Serial – Miss McCaffrey pt04


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going..


“Well, Jeremy, let’s review that passage you’ve been reciting,” Miss McCaffrey said, getting to her feet.

I remained safely seated on the couch as I recounted the story of the gardener and the heroine. As I arrived at the point where he was tearing the clothes, Miss McCaffrey said “Now, Jeremy, don’t tell me. Get up and show me.”

I was still a bit unsure about our ‘metaphor lesson’. I grabbed her dress and I decided to check. “Do you mean, do it for real, Miss McCaffrey?”

“Yes, for real,” she reaffirmed with a warm smile.

Tearing the bottom buttons of her dress as she stood before me panting, her hands working their way through my hair. When I got about five or six buttons up I found that, other than that pendant around her neck, this thin sun dress was all the costume that Miss McCaffrey was going to be using to teach her lesson today.

“Keep working gardener,” she said breathlessly.

I finish with the buttons assignment and was amazed with the display before me. My teacher’s sundress fell open and I was introduced, for the first time, to a beauteous pair of firm, grapefruit, sized breasts. They were pale and topped with large pink nipples. I was openly awed. She pushed be back and I fell, sitting on the couch.

Miss McCaffrey stepped towards me straddling my legs and lowered herself down onto my lap. My arms snaked their way firmly around her, and she brought her lips down, engulfing mine and searing them with a passion that was all quite new to me. I answered her kiss with several of my own and I must have gotten a passing mark as she stood up, grabbed my arm and led me up the stairs to her bedroom the sundress flying behind her like a superhero’s cape.

Happy New Year! – Wednesday Serial – Miss McCaffrey pt03


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going..


I made steady progress reciting the passage Miss McCaffrey had highlighted for me. The vocabulary in the book from the shelf wasn’t all that challenging. It was a romance novel and I was coming to a scene where a dark haired woman wearing a dark blue sundress was being swept up in an embrace by a well-built gardener.

Miss McCaffrey returned from the kitchen and bending in front of me, placed a tray with a sweating pitcher of iced tea and two glasses on the coffee table. I momentarily lost my place where I was reciting the passage at the sight of her breasts nearly falling over the top of her dark blue sundress. But, I recovered quickly, and continued reciting as she walked around and sat down beside me on the couch.

I used all my focus to not watch as she slowly crossed her long legs. But I did notice that my tempo had changed a bit. I’m sure she noticed it too. As I continued reciting the bodice ripping scene, Miss McCaffrey put one arm around me and her other on my shoulder. She spoke right into my ear “have you done much gardening Jeremy?”

“Umm, no, not really, Miss McCaffrey,” I stammered once I overcame the suddenness of her touch, “But I did help my aunt with hers last year.”

She let out a light bit of laughter. “The double meaning of words is one of the projects we will be working on today. And you will be doing some gardening here Jeremy.”

She planted her lips lightly against ear, “All you need is a nice fertile place to begin…” It was then that I began to think that her gardening project might not have anything to do with plants.

Merry Christmas – Wednesday Serial pt 02


Miss McCaffrey – a short story about a boy and his after school lessons…c’mon we all know where THIS is going..


Miss McCaffrey lived just a couple of blocks down from my folks. My Mom had met her two years ago when she first moved in, as Mom was the realtor when Miss McCaffrey bought a house here.  I think that’s how I became pressed into service doing the fall leaves raking and gutter cleaning for the new teacher. It was during last December’s snow clearing that she offered to give me extra tutoring to improve my reading comprehension and writing skills.

She would assign me short stories, or sections of larger works and have me write my thoughts, feelings, interpretations. I really enjoyed the extra challenge, and someone caring about what I thought about anything.

She was wearing a light, cotton, dark blue, sundress with buttons running up the front. It was low cut because I could see the pendant that she always wore resting nicely in her pure white cleavage. I also found it curious that her breasts were moving a bit more freely than when we were in school.

“I’m thinking that ‘The Garden of Eden’ may be a bit advanced for you right now. Perhaps in a couple of weeks we’ll revisit it,” she said fetching a book off the top shelf of a bookcase. I thought it odd what she said as school was over in just two weeks. I watched her stretch and reach for the book.

“For now let’s try something a bit more contemporary,” she said turning around. I’m sure she caught me looking. She handed me a book with a bookmark in it and asked me to have a seat on the couch. She told me to

“Start reading the highlighted passage,” she instructed with a wry smile. “I’ll get us some iced tea.” I watched her lovely dress sway into the kitchen.