I Won't Disappoint

Hi everyone!

I would like to thank LOVECRAFT68 for including me in this challenge,Pay For Play Story Event. Throughout the past year, I have discovered that the age gap sub-genre of the Erotic Couplings category has become my specialty. Personally, I love this category because it tells the stories of adults who shouldn't be having sex, but for a multitude of reasons--or sometimes no reason at all--end up getting together. It's risky, fun, and sexy all at the same time.

In real life, the consequences of most of the scenarios in my stories could be life changing in a negative way. But thanks to Literotica, I--and you--can explore these fantasies through stories without having to worry about such consequences.

I love to create strong, beautiful, precocious female characters. I hope Haley, the female lead in this work, is a worthy addition to my female cast while also satisfying the requirement for this challenge. Yes, she's going to be getting paid. But she and Mr. Roberts, our male lead, will be having a lot of fun along the way. And yes, Mr. Roberts' bank account, among other things, will be quite drained by the story's end!

As always, I appreciate your constructive feedback, either by leaving a comment or sending me a message through my profile. I always answer messages and also love hearing your ideas for future works. Enjoy!

--Dani

All characters are fictional and over the age of 18.

"A thousand bucks, Mr. Roberts."

"A thousand bucks, Haley," I answered, my heart sprinting out of my chest in anticipation, my cock straining so hard up against the fly of my khakis that I thought it would shear the zipper in two.

And with that simple transaction, I had exactly $37.92 left in the checking account that I shared with my wife. But that was a tomorrow problem. It was time to claim what I paid for: to fuck my 21 year old student teacher from behind on my classroom desk.

"Did you lock the door to my classroom?" I asked.

"No," she answered. "You told me not to. You liked knowing that we could be caught easily, despite the consequences."

I already knew the answer because I watched her every move as she walked into my classroom in a short plaid skirt that barely covered her slender golden brown thighs. The long sleeved tan cardigan ended on her midriff, leaving about an inch of tanned skin, and her navel, exposed. She tantalized me every time she wore that sweater to class. It was probably--make that definitely--inappropriate for a student teacher to wear such an outfit while teaching literature to bunch of hormone laced teenagers, let alone her almost 50 year-old, sex starved preceptor.

I flashed to the first time my hands disappeared under the cardigan. It was a late Friday afternoon in the bedroom of her college apartment. I should have been sitting down to dinner with my wife. Instead, I was slowly undressing my student teacher for the fall semester. I had just given her $400 in cash to be alone with her for an hour. I hadn't had sex with my wife in over five years. It was the easiest four hundred bucks I ever spent.

Not only hadn't I had sex in over half a decade, I hadn't touched my wife, or more importantly been touched in even longer. I was desperate for physical contact with another human--any contact. I really didn't care that much about the sex (OK I actually did). But just as much, I wanted to touch, to feel. More importantly, I yearned to be touched. I made this yearning, this basic need, crystal clear to Haley at the outset of our agreement. It wasn't just sex. It was the whole ball of wax: touching, kissing, exploring, and yes, sex. Oodles and oodles of sex.

And that first night, in the dim light of her apartment bedroom while her roommates celebrated happy hour (on my dime) at a local dive bar and my wife was happy to NOT see me pulling into the driveway, Haley did not disappoint.

I drank in her 21 year-old body like a parched man who lost in the desert, my hands and lips savoring every bit of her with her skirt and cardigan in place and then even more fervently as I slowly undressed her and revealed the immortal perfection of her young body.

She feasted on my body with even greater ardor, as if she felt every excruciating moment that I would lie awake deprived, inches from my beautiful wife-inches that might as well have been miles. A wall ran down the middle of our bed. It was a figurative wall, but a wall nonetheless.

She showered my chest with soft wet kisses as her tongue swirled around my erect nipples. It was almost too much to process. My deprived tactile sensory fibers fired out of control after being dormant for years. Her short bob of hair hung down over her face and grazed my skin while her hands undid my pants. I was in heaven.

After undressing each other, I covered her with my body and buried my erection in her. The sensation of her young pussy gripping my cock nearly sent me over the edge. I closed my eyes and held my ground, fighting every instinct that would lead me to the point of no return.

She was patient with me, allowing me to dwell inside her and let the impending climax wane. Eventually I was able to rock my hips gently, my cock plunging her depths, her slick walls drawing me in and sending waves of pleasure through us both. I was able to stave off my climax for a bit longer, until physiology took over and sent me into a mind bending orgasm, my cock pumping wave after wave of cum into Haley. She also came in short order, her cum-filled pussy pulsating in waves around my softening cock.

We rested only for a minute or two, spooning. My refractory period was essentially nonexistent as lust made me hungry for more, determined to make up for years of forced abstinence.

"I want you again," I whispered into Haley's ear. "I'm ready."

Haley looked down at my expanding, glistening cock resting on her right ass cheek.

"Mr. Roberts!" she exclaimed, seemingly astonished at my renewed hard on.

I looked at her alarm clock. It was 5:20. I had 40 minutes. Haley was laying on her left side with her right leg bent up towards her stomach as we spooned. She just happened to be in a perfect position. I lowered my body slightly to align my tip with her entrance. We gasped in unison as I entered her again. I ran my right hand along her thigh before sliding it up to her hip, steadying her.

I was relentless, plowing her from below. We moaned loudly, vocalizing our mutual ecstasy, thankful that there were no roommates in earshot. I kissed her shoulders, which formed beads of sweat as my lips and tongue roamed. We came--again--each of us now covered in sweat, Haley's light green sheets becoming wrinkled while they wicked away our bodily fluids. I felt like I was living a porno. It was the greatest 30 minutes of my life.

We rested again. This time was a little longer. We giggled and kissed and touched and fondled. It was intimate and sexy and passionate. In a word, it was perfection.

Haley brought me to my knees on her bed and went down, my slick cock increasing in turgor in her mouth as she slowly worked me in and out of her mouth. Her full lips, lips that were teaching high school literature just a couple hours ago, were now wrapped around my shaft.

Twenty minutes ago, I would have come in 30 seconds as this 21 year-old sucked and swirled and moaned around my cock. Having just come twice since 5:00, it was going to take a bit for me to climax. I ran my hands up her slender upper arms, over her shoulders, and down her back. I kissed down the center of her back, covering her torso with mine. Haley's pace built steadily, fucking my cock with her mouth. Her right hand grazed my balls before traveling backwards, stoping for a moment at my taint, and then returning to my balls. She rhythmically repeated this process as she continued her oral mastery.

I lifted my torso from her back to take in the visual of my cock disappearing into Haley's cute little mouth. That was all I needed to see. My cock twitched and then I came hard. She swallowed each wave of my third orgasm in 40 minutes. I collapsed on her bed. Haley climbed up my spent frame and kissed me deeply. I tasted my salty seed as it cascaded from her tongue down onto mine.

As the hour struck six, I pulled myself away from her spent body. I too was exhausted but along with the exhaustion came a feeling of satisfaction that I hadn't had in years, if ever. Yes, I just cheated on my wife of 20 years. To make it worse, within the span of an hour I fucked my student teacher who would had been teaching alongside me in my literature class for the whole semester. And to make it even worse, I paid her for it.

The only thing that could possibly make it more apprehensible was that, as I left her in her bed covered with our bodily fluids, I reached into my wallet and placed $100 on her nightstand.

"Down payment for next time?" I asked, flashing her a grin while buttoning my shirt.

She looked at the money and then back at me.

"You bet," she answered. "How does Monday sound?"

"Perfect," I replied, a renewed erection stirring in my wrinkled khakis.

.....So how did I get here? Specifically, how did we get to the point that I was paying her $1000 to bend her over my classroom desk and fuck her from behind?

If I've earned your attention so far, I'll tell you the backstory.

Haley was a Secondary Education major with a minor in Literature at our local university. Her particular course of study made her the perfect candidate to student teach in my Advanced Classic American Literature class. I had been a teacher for nearly 25 years. And quite frankly, I was getting a little bored of the yearly routine. Classic Literature didn't change at all, so neither did my curriculum. It was the same damn material year after year after year. So, having a young, eager, student teacher who was a junior in college roll up to my classroom door was a welcome respite from the monotony that had become my career as a high school teacher.

My personal life had also fallen into a rut--to put it mildly. My wife Liz and I had grown apart to the point that we were basically roommates, cohabitating in our modest home. We were decent roommates but lousy spouses. Our conversations were topical. We ate mostly in silence. It had been over five years since we had last been intimate.

I loved her and was still attracted to her. She was beautiful. But the spark between us had died long ago. Yet, neither of us ever brought up divorce. I think in some way, we were codependent in our disfunction. It allowed us to co-exist. It sounds ludicrous because it is. It's a loveless, sexless, connectionless, meaningless status quo. For some unexplainable reason, neither of us could put an end to it.

Enough misery.

When Haley met me in my classroom in mid August for orientation, I was strictly by the book. She was a 21 year-old college junior with straight, dark brown hair that went to the middle of her back. She had olive skin and cerulean eyes. She dressed conservatively in a long skirt that went below her knees, high leather boots, a long sleeved blouse. Her lips curled into a smile as she talked. In a word, she seemed cute, but that's about it.

We shared some superficial details about life and then dived into the curriculum for the upcoming fall semester. Haley devoured each item of the syllabus. I watched her eagerness grow as we went from one classic work to another, culminating in the final exam. She was going to be a great teacher: that was clear to me. Her enthusiasm was contagious, to the point that I was even slightly excited about teaching again. A renewed sense of hope grew in me, thanks to the budding teacher who would be my partner for the next three months.

The last two weeks of the summer were uneventful. Haley and I were set to meet up the day before class started to make our final preparations for the semester. There were seating charts to create, chairs to arrange, and a million other small, annoying tasks to get done. But at least this year I would have a partner to split the work.

I had already started to line up desks in rows when Haley arrived at the door to my room.

"Good morning, Mr. Roberts!" Haley announced as she stood at the classroom door.

I nearly dropped the desk I was moving when I saw her. The conservatively dressed young woman with unremarkable straight brown hair that I met only a couple weeks ago had transformed. I almost didn't recognize her, save for her blue eyes and warm smile.

Her hair was cut into a smart little bob that curled around the sides of her ears, framing her face perfectly. Light brown--almost blonde--highlights were now interspersed with her natural dark brown hair--creating a striking contrast, that along with her new bob, changed her look completely.

She wore a short sleeved white t-shirt that ended just above the waist of her ruffled navy blue athletic skirt. The outfit revealed her slender, toned arms and legs. Her arms were folded and her left knee was bent slightly as she leaned against the doorframe. It was as if she knew how startled I was at her change in appearance.

"I know...I know...my hair!" she said. " I chopped it!"

"Hi Haley! Welcome! Great to see you!" I said, hastily putting down the desk in my hands.

"No, no, it's lovely, Haley!" I replied, feeling sorry if I made her uncomfortable. 'It's great to see you!" I realized I was repeating myself and it felt awkward. I didn't know what else to do but continue to prepare for the looming semester. Haley joined me in the classroom and immediately started to help arrange the desks.

We then moved on to creating the seating charts for each class. I sat at one of the student desks and she pulled up a desk next to me. It took a couple hours to complete this task but I found the minutes passing quickly as Haley picked up the steps of the process quickly and eventually was essentially creating the charts on her own. I could see her growing satisfaction and eagerness to begin teaching as the seating arrangements for each section took form.

As she worked with her legs crossed under the surface of the desk, she would occasionally pull her short hair to the back of her head, as if she was putting it into a ponytail. It was way too short for a legitimate ponytail of any kind, but she would hold it there for a moment, her arms temporarily above her head as she held her hair in place. The shorter strands, which happened to have the blonde highlights, would break free from her grasp and curl along the side of her face, glancing her jawline.

To this day I can't explain why, but when she did this simple maneuver, I couldn't look away from her. She would eventually free the remaining strands of hair and lower her arms. Her bob would fall haphazardly and linger for a few moments in a disorganized knot before she combed through it with her fingers, restoring it so that it again curl by her ears.

We finished the seating charts along with the rest of our tasks and closed up the room for the evening. Haley was eager to begin her student teaching experience. And for the first time in decades, I too was eager to teach again with this young, energetic woman at my side.

Haley was in my room first thing the next morning, her energy palpable. She wore a short plaid skirt with navy leggings and a white short sleeved blouse--more conservative than her rather revealing outfit from the day before, but far more youthful than the long skirt she greeted me in a few weeks ago.

She was a natural teacher. I guided her on a few major themes but she took the rest from there, leaving me to observe this young star teach Literature like a pro. Her passion for great works was evident and contagious, eliciting interest from even the most apathetic of students. It was a wonder to watch her work day in and day out.

Haley and I would spend our lunch periods and about an hour after school each day correcting quizzes and tests and going over the next day's lesson plans. Working on these once tedious task became near effortless with her by my side.

We would pull two student desks together and pass our papers and notes across the work surfaces while we chatted about life in general. She would tell me of her roommates, the occasional love interest, going out on weekends, and everything else that occupies the days of a college junior.

I would pepper in some details of my life like my hobbies, which I didn't really have other than exercising, my relationships with fellow teachers and other bland things. I honestly felt like a total and complete bore compared to my young counterpart.

One afternoon, as we trudged through grading the first exam of the semester, Haley broke the work conversation with a question out of left field.

"Mr. Roberts, can I ask a question?"

"Sure, Haley. Shoot." I was expecting her to ask for a clarification about a difficult question on this week's test. What she asked nearly knocked me from the small student desk in which I was sitting.

"What about Mrs. Roberts?" Haley asked, her blue eyes settling on my wedding ring.

It occurred to me that in all our conversations over the last few weeks, I had not once mentioned my spouse. I felt as though I should have crawled under my desk and died. Here I was a married man working with a student teacher for weeks and not once did I mention my spouse of over 20 years.

"What about her, Haley?" I replied. "What would you like to know?"

"It's just that you've never told me about her. I was wondering why.

Does she not like that you're working with a student teacher?"

"No, no, of course not," I answered. The truth was that my wife didn't even know about Haley because we never talked about my work. She never asked about it.

I stopped grading the exam in my hands and put the paper down. I was going to make something up but just didn't have the energy. Brutal honesty was the only way out.

I took a deep breath and looked Haley in the eyes.

"It's just that things are....well...weare not good, Mrs. Roberts and I."

Haley broke our gaze and looked down at her desk.

"I'm sorry, Mr. Roberts. I didn't mean to pry."

"It's OK," I reassured her. "Marriage is tough. We are trying to work through things but it's an uphill battle."

"I get it. I mean I don't....I'm not married..." Haley stammered, clearly uncomfortable by my bluntness.

"I'm sorry for asking is what I mean, Mr. Roberts."

"I'm actually glad you did--really, Haley. We are coworkers and coworkers talk about these things. Please don't feel bad."

I seemed to have reassured her. Her gaze softened and we continued to grade our papers in silence.

As the weeks passed, Haley and I continued to work seamlessly together. I grew very fond of her teaching style and even more fond of Haley in general. I melted as her smile curled her lips while she taught her students. Her bob grew out just enough to be put up in a short ponytail with the two blonde strands framing her jawline. It was early fall when she first wore the cream colored cardigan that left her lower midriff exposed. When she raised her arms to write on the chalk board, her navel appeared from under the sweater.

I was unable to pay any attention to her lesson as my favorite sweater tantalized me with coveted views of her beautiful light brown skin.

I chastised myself for enjoying anything other than the teaching skill of the college student before me. Instead of taking notes on her style and jotting down constructive feedback for Haley, I began to fantasize about how her soft her skin must feel. I imagined my lips against hers, my hands disappearing under her plaid skirts, which seemed to be getting shorter as the weeks went on, slowly revealing her thighs, inch by glorious inch.