A Date for the Prom

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Older woman suggests herself as Prom date.
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Alex De Kok
Alex De Kok
1,346 Followers

To the friend I never met, for what might have been, this tale is dedicated.

It began last spring. I knew my grades were good enough for my scholarship, except for my English. I needed an A and at the moment was heading for a poor B at best. Mom and Dad knew I was trying hard and one Friday evening, after supper, Dad asked me if I thought some extra tutoring would help.

"I don't know, Dad," I said, "I guess it could help."

"I think it would," Dad said, "especially one-on-one, with no other students to get in the way."

"Well, yeah, I think that would help."

"Do you know Ms Shillings?" Dad asked.

"I've seen her around. Why?"

"She teaches English in Larson High. She's prepared to take on occasional students for part-time extra tutoring. I had a word with her earlier today and she said she would be prepared to take you on as a student. Saturday afternoons, one until four. It means you'll miss watching your football, but I think your grade is more important."

I remember pulling a face, but Dad was right, I needed the grade. "Okay, Dad, when do I start?"

"I thought you'd agree, so you start tomorrow. She says not to take anything except your brain, a notebook and a pen. She has enough books.

Well, the pen and notebook I could manage; the brain I wasn't sure about, but I duly turned up at her house on Elm at one o'clock next afternoon. It's difficult, thinking back, to remember my first impression but as far as I can remember now it was fairly neutral.

I expected to see a teacher. Being a Saturday, I expected to see an off-duty teacher, and I guess that's what I saw. Her hair style has remained pretty much the same while I've known her, so what I saw was a woman in her late twenties, although I didn't know her age then and I still think she looks a lot younger, not tall, slim, with short auburn hair and brown eyes, huge through big round glasses. If I remember right, she was wearing blue jeans, a loose sweatshirt and moccasins.

"Hello," I said. "My dad said he'd talked to you about tutoring. For my English."

"Of course," she said, smiling and opening the door wide. Even then I noticed what a beautiful smile she has. "You must be James Bartlett."

"I prefer Jim," I said, "If you don't mind."

"Of course I don't mind," she said as she ushered me in and closed the door, "Jim it is. This way then, Jim." She led the way into what I learned was her den. At the side of the house, not overlooked by any neighbours, it was a big, comfortable room. Two computer terminals were set at right angles in a corner, bookcases covered most of the wall space and there was a big couch in the middle of the room. A table with two chairs was placed beside the window. An insulated coffee jug and two cups were on the table, with cream and sugar.

"Coffee?" she asked, making her way to the jug.

"Please. Just black."

She poured coffee for us and led the way to the couch. "Sit down," she said, sitting at one end and tucking her feet neatly under her. "Tell me what you think I can do for you."

"WhatI think?"

She nodded. "Please."

"Well," I began, "I have the offer of a University scholarship, but it depends on my getting a GPA of 4.5 or better. I'm confident in my other subjects, but I'm weak in English. My English teacher is very helpful, but doesn't have the time to give me the attention I need. My work isn't too bad, it's just not going to be good enough to get the A I need." I took a sip of my coffee. Good!

"Are you prepared to work hard?" she asked bluntly.

"I want that scholarship. I have to work," I replied, equally blunt.

She nodded. "All right, let's get started. On that terminal," she said, pointing, "you'll find a test. I want you to complete it. The answers will be registered on my terminal and I'll mark it on there. You'll have fifteen minutes for the test."

And that was the way it began. She marked my test and while she was marking, I was working on the first of the many written assignments she was to give me over the course of the next few weeks. With hindsight it was enjoyable, but I never thought so at the time, as she was always pushing me to my limits. It seemed no time at all before four o'clock came and I was leaving. She even gave me homework!

"Jim," she said, "I want a written essay from you by Thursday, on why you want to get an A in English. I want the background, I want your reasons for seeking extra tutoring, and I want your reactions to what we've done, with reasons, for and against. Thursday. Fifteen hundred words. Drop it in my mailbox." She smiled. "Cheer up, I think you'll do it!"

That was the way things went until that memorable Saturday, a few weeks before the Senior Prom. I arrived at Ms. Shillings' house, as usual, at one. By ten past we were on our coffee and while she was marking my assignment I was taking her revision test. The telephone rang.

"Damn," she said. "Sorry, Jim. Excuse me for a moment." She picked up the 'phone. "Hello? Yes, this is she. Yes. It is? Oh, good. Now, if it's convenient. Fine, I'll be there as soon as I can. Thank you. Goodbye." She turned to me. "Jim, that was the auto repair place. My car's ready. I need it tomorrow, so I'm going to fetch it. I have another test for you, so what I'll do, I'll telephone for a taxi and you can start the test when I leave. It's intended to take an hour and I should be back before you're finished. Is that OK?" She smiled. "I don't think you'll cheat by looking at the answers, not until you've finished."

I grinned at her. "I need to get an A honestly. Cheating won't do me any good."

"Good man. Now excuse me while I get my coat and ring for a taxi."

Twenty minutes later she left and I started the test. Forty-five minutes after that I finished the test. Five minutes after that, the 'phone rang. I let her answering machine kick in and was surprised to hear her voice.

"Jim, it's Catherine. Please pick up the 'phone. I need you to do something for me. Jim?"

I grabbed the 'phone. "Hi, Ms Shillings. What do you want me to do?"

"Jim, in the drawers on my PC desk, third drawer down, there's a folder labelled 'Auto'. Can you find it and bring it to the 'phone, please?"

"Hang on a second." I went to the desk and quickly found the folder. I took it to the 'phone. "Okay, I have it."

What she wanted was a reference number from a previous service, and it was a matter of moments before I found it and passed her the information. Perhaps I was clumsy, but when I replaced the folder, I dislodged another which fell to the floor beside the desk. About to put it back I noticed that a photograph had slipped partially out, and a rather attractive portion of female anatomy seemed to be on show. Intrigued I slipped the photo out, and then gasped. Of all the things I might have expected, my tutor naked was not one of them!

Obviously taken outdoors, she was sitting slightly turned, her left arm almost behind her, her right at her side. Her legs were spread and she had the sole of her left foot pressed against her right leg, just below the knee. A lovely pubic bush shrouded her sex and her hair, longer when the photograph was taken, hung almost to the nipple of her left breast. I goggled in admiration at the picture, my prick stiffening in my jeans.

Fascinated, I opened the folder, never thinking I might be invading her privacy and gasped anew. More nude photographs, both artistic and explicit, and under those, more of her with a man in positions which could only be described as uncompromisingly sexual. I studied them, breathless, my prick becoming an iron bar in my jeans. Pictures of her astride a man, of her on her back with him penetrating her, of her playing with his prick, of her.... I was almost breathless, aroused, admiring. I spent uncounted time in just looking at those pictures, over and over. I never thought for a moment of these pictures being pornographic, all I could see was a beautiful woman, a woman I knew, a neighbour, indulging in sexual activities with her lover. I tried to ease my prick in my jeans and almost jumped out of my skin when she spoke.

"Are you disgusted, Jim?" There was anger in her tone, but there was a sadness, a sadness that was terrible to me, the sadness of betrayal, but also of something else.

I spun around at her voice, shocked. Shocked even more to see the tears cascading unheeded down her cheeks, I felt a sense of profound guilt. I shook my head wildly.

"No," I stammered, "they're beautiful, you're beautiful, I wasn't prying, they fell out when I put the other folder back." I stammered into silence.

She held out her hand and I fumbled the photographs into the folder and passed it to her. Her eyes were distant, unfocussed, as she clutched the folder to her chest.

"He was my fiancé, Jim. Peter, his name was. We were to be married eight days after he was killed in a car crash. They are almost the only photographs I have with him on them. That's why I kept them." She paused. "They're very special to me." Finally, painfully, she raised her eyes to mine. "Now I suppose you'll tell all your girl friends."

Now it was my turn to feel the pain. "I would never do that," I said vehemently. I laughed shortly. "Anyway, I have no girl friend."

"You haven't?" Despite her pain, there was surprise in her voice. "A good-looking boy like you, I was sure...."

"Oh, I did have, sure. But...." My voice trailed off and I could feel the embarrassment creeping over me yet again.

"Something went wrong?" she asked gently, wiping her eyes with a handkerchief.

I nodded, feeling unshed tears in my own eyes.

"Do you want to talk about it?"

I shook my head, 'no', but almost without volition felt my mouth open and my voice uttering forth.

"Do you know what the girls in school all call me?" I asked bitterly.

"No, I don't," she said quietly.

"Hot shot. You know why?" I asked, my voice harsh.

"No. Do you want to tell me?"

"Because I cum as soon as a girl touches me, that's why."

"I don't understand, why 'all the girls'? Did someone tell?" I was surprised by the rising tone of anger in her voice.

I nodded. "My ex-girlfriend, Alison Tandon."

"I know her, I think. The redhead, two blocks down. Pretty girl."

"Yeah, her. We'd been dating for ages, getting more and more intimate, but no touching 'there', you know?"

"Yes, I know. Go on."

"Well, this night, she agreed to give me a hand job," I said, remembering. "I took it out and she had a tissue ready, but I was too excited, as soon as she touched me, I came. It wouldn't have been so bad, but I came all over her face and her blouse and she grossed out." I laughed shortly. "She ran off home and her mom caught her sneaking in and went ape, grounded Alison for a month. She blamed me, and told it around school. The result is, I don't have a girl or any chance with one at school. Some of the boys, mostly the brainless ones, mock me but since I busted the biggest one, they leave me alone." I shrugged.

"Oh, Jim, you poor soul, no wonder you didn't answer my questions about the Senior Prom," she said gently. "Would you go if you had a partner?"

"I think so, yes. I just couldn't face going by myself." I laughed shortly. "I have the tickets."

"Would you like me to go as your partner, Jim?" she asked and I looked at her, astounded.

"But," I began, "you're a - umm, you're a teacher, you're older than me, I mean...." My voice trailed off.

She smiled ruefully. "Excuse me for a moment, I'd like to introduce you to your date for the Prom."

She went out and I sat, confused. Who? She had just said she would like to be my date and now she was saying she wanted to introduce me to someone. I mean, she'd told me she lived alone. I was baffled. I waited. She was gone for about ten minutes and I was sorely tempted to take another peek at the photographs that she'd left on the table, but I wouldn't betray her trust a second time.

"Jim?" she called. "Sit on the couch and close your eyes, please."

Puzzled, I did as she said and waited. I heard her coming in and moving to stand before me.

"Okay Jim, open your eyes."

I did and gasped. Had I not known her voice I would never have recognised her. Long, curling, honey-blonde hair fell past her shoulders in complete contrast to her own short, dark hair. The glasses were gone and her eyes were bright. She wore a school sweater and a short pleated skirt, sneakers on her feet. She looked about seventeen. She held out her hand.

"Hi, I'm Cheryl," she said in a voice that was a husky parody of her own. "Catherine says you have no date for the Prom." She gave a shy smile. "I'd like to go with you."

"Are you serious, Catherine, umm, Ms Shillings?" I asked in a daze, "because if you are I would be delighted."

She laughed and took off the wig, then sat beside me on the couch. "Deadly serious, Jim. You realise why I'll have to go in disguise?"

"Yup. You're a teacher. Okay, not at our school, but still a teacher." I shook my head. "Incredible, you look so young like that."

She laughed. "Jim, when I was finishing my degree, I had to carry my birth certificate around with me. Barmen wouldn't believe I was over twenty-one. I even wear the glasses now to make me look older. I don't need them, they're plain glass."

I looked at her. "You're sure you want to go as my date?" I flushed. "I mean, people might expect me to kiss you or something."

"I think I can cope with that, Jim," she said, smiling gently, "but I think from now until the Prom is over, you'd better get used to calling me Cheryl."

"Okay, Cheryl," I laughed, but then frowned. "About the photographs," I began awkwardly, but she put a finger on my lips.

"Will you give me your word that you will never tell anyone?"

"On my honour, I swear it," I said.

"Okay, we'll say no more," she said. "Memories are fragile things."

"Just one thing," I said.

"Yes?"

"I'll never tell, but I will remember those photographs for a long, long time. You are beautiful." I held my breath, thinking 'Fool! You should have kept your mouth shut!'

She looked at me without speaking for a long moment, then smiled. "Thank you, Jim. Now, where's that test?"

"Over here, Ms. Shillings, " I said then caught her look. "Sorry. Over here, Cheryl."

Suddenly, from dreading to even think about the Prom, I was looking forward to it. Monday found me frantically trying to organise myself a tux, but I struck lucky and got one in a deep wine red, with a black vest. Dad offered me a choice of his ties - he actuallyowns a tux - and Mom promised to buy me a new shirt. Apart from transport, I was ready.

"Corsage?" Mom asked.

I groaned. "Oh, heck, I forgot."

Mom grinned. "All taken care of, son. Your Aunt Charlotte is bringing it on her way home from work that Friday. Her treat, she says."

"Dad?" I began, but he stopped me.

"Yes, Jim, you may borrow the car, on your word of honour that you will not drink any liquor. On that basis, as the day after the Prom is Saturday, so long as the car is ready to take me to my Saturday morning golf, it's yours for the night."

"Sir, you have my word," I said.

"Very well." Dad grinned suddenly. "I wish your Grandad had owned a car for my Prom." Mom gave him a sideways look, a half smile on her face, and I remembered them saying they'd started their romance on their Senior Prom night. They hadn't gone together! Everything was ready, now all I had to do was wait.

That was the hard part. I still had two Saturday tutoring sessions to go before the Prom, and another three after. When I turned up for the last session before the Prom I stopped in my tracks. Catherine Shillings was in her 'Cheryl' persona, blonde hair piled up, jeans and sweatshirt.

"Hi, Jim," she said. "Come on in. Catherine asked me to take your session today. You don't mind, do you?"

"Umm, no, Cheryl," I managed to say, "that's fine." And it was, too, because Cheryl was as hard a taskmistress as Catherine. Four o'clock came and we called a halt.

"Jim?"

"Yes?" I said, packing my papers.

"Who knows you're taking Cheryl to the Prom?"

"Just my folks," I replied.

"Who am I? I mean, to your parents."

"I told them you were Catherine's cousin. Was that okay?" I asked anxiously.

"That's great, Jim, but have they never wondered why you aren't dating Cheryl?"

I nodded. "Mom's been hinting that she'd like to actually meet Cheryl."

"I think she should," she said. She grinned at my startled expression. "Pick Cheryl up at seven, Jim, you have a date!"

My heart leapt. "Great!"

I was prompt, in my best casual garb, anxious over my choice. It was silly, I knew I was acting a part and that Catherine was too, but I had all the conventional anxieties of a young man on a date. She must have seen me coming, because she opened the door as I walked up the path, greeting me with a smile. The blonde hair was drawn back into a simple ponytail and she was wearing a dusky pink blouse and cream jeans, snug cream jeans, and I realised almost with shock that Catherine Shillings had a beautifully shaped ass. My greeting was unrehearsed.

"Cheryl," I said, "you look great!"

She smiled in what seemed genuine pleasure. "Thank you, Jim. Just a moment until I get my purse."

Two minutes later, we were off. I was unsure of what to do, but she took my hand in hers with a smile. "I think we should hold hands, Jim, it looks more natural."

I wasn't arguing, as it was the first time I'd held a girl's hand for ages. I headed automatically for home.

"Where are we going," she asked, with a half smile.

"Home," I said. "Dad said I could borrow the car if I took you to meet them first."

"Ah," she said. "Jim, this could be awkward. I think your mom will see I'm an older woman. I'll have to pretend to be about twenty," she said, smiling. "Have you said anything about me in school terms?"

"No," I said, shaking my head. "Only that you're Catherine's cousin and that you're staying with her for a little while. I sort of hinted that you'd already graduated."

She squeezed my hand. "Good thinking."

Five minutes later I was introducing Cheryl to my parents. Dad was the gracious host and Mom was her usual friendly self. We only stopped a moment or two. Dad passed me the car keys with only a token protest and Mom managed to whisper "she's lovely" as we said our farewells.

"Where do you want to go?" I asked as I started the car.

"I'd like me to be a surprise at the Prom," she said, "so let's go somewhere we won't meet anyone from school."

I thought for a moment. "Most of the kids go to the diner first on a Saturday, then to a movie or something."

"How about Green Lake?" she asked, her eyes twinkling.

I laughed. "Not in daylight." Green Lake was a popular place to go and make out, usually after dark.

"I haven't actually been to Green Lake," she said. "I thinkI'd like to see it in daylight."

"Green Lake it is," I said, and headed out that way. When we arrived, we were the only ones there. After I'd turned off the motor we got out and just listened to the stillness for a while.

Catherine breathed deeply, and I tried not to look at the tantalising swell of her breasts, and then she said, "Come on, let's walk a little," leading the way off along the path. As I caught up with her again she took my hand.

We were there for about an hour, just walking and talking, with her quizzing me again about my plans for my future, and me telling her how I wanted to work with computers. There was another thing, too. "I've enjoyed the extra tutoring in English," I said, "I'm getting a much better idea of how to use words, to put them together to tell a story, or to describe something."

She smiled at me, and for a moment lapsed from the Cheryl persona she wore so convincingly. "It shows," she said. "The work you're producing now is much better than when you started."

Alex De Kok
Alex De Kok
1,346 Followers