I teach at the exclusive Roxbury Academy, a private all-girls college in Massachusetts. Actually, “exclusive” may be a bit of an understatement for this place; the income level of the parents — and the snobbery of the students — is so profound that they actually look down on girls going to Harvard and Yale because they weren’t good enough for Roxbury. I know for a fact there are several girls here whose fathers run some of the largest and most powerful corporations in the world, several diplomat’s and senator’s daughters, a few girls whose parents are either producers, singers, actors, or some other example of Hollywood rich and famous, and numerous kids of the nouveau riche from all over the world. I think there may even be a Saudi princess or two here.
So let’s suffice it to say, it is beyond exclusive.
You might think that for a college that clearly earns so much money, pay for the staff would be at a fairly comfortable level. You’d be wrong. Simple fact of the matter is the board chooses to take its unbelievable amount from tuition and endowments and put it back into pet projects that keep the girls as pampered as possible rather than paying us teachers what we deserve. For example, the college recently took some of its money and built a brand new fitness studio — complete with juice and natural spring water bar, of course — and a “student relaxation center, ” even though there was a perfectly acceptable gym and recreation center for the girls that were but a few years old. In that same year, we teachers had an additional ten per cent taken from our pay for health care.
In fact, about the only way in which the board is not utterly tripping over itself to keep the girls and the girls’ parents happy is when it comes to grading. At least in that respect we teachers have the ultimate say, and neither dean nor president nor parent can sway a grading decision once it’s been made. This is a tradition that goes back the 1831 when Dorothea Roxbury founded the old place as a finishing school for the female elite of her society. As the daughter of a rich industrialist herself, she knew being raised in such pompous luxury could make a girl have certain unrealistic expectations out of life. When these young ladies would then marry equally arrogant and indolent young men of their class, they would soon find their wishes became secondary to those of their husbands, and Dorothea wanted her girls to have the wherewithal to suffer through hearing the occasional “no,” especially when it was because she failed to work hard enough at her studies. So the primacy of the teacher’s grades has been a cherished and long-respected tradition at the Academy to this very day.
Although Dorothea developed this rule to instill a little humility in those girls, she unknowingly allowed me to have the greatest fuck in my entire life.
It was late one night towards the end of the spring semester and I was working in my office finishing grades. I had the windows opened and the cool, fresh breeze of the New England spring was blowing in my office, yet despite that my mood was rather foul. Many of my girls were either flunking outright or just barely passing. I understand literature, especially British literature, can at times be a boring subject for these young ladies, but I also knew full well my students were capable of passing my class. The fact that so many of them were doing so poorly was a reflection of the degree to which they have grown accustomed to having others pick up the pieces for them. Well, thanks to Mrs. Roxbury’s rule, at least in this case they will find what happens when one doesn’t apply themselves.
It was in this mood that I first heard the sniffling in the hallway approaching my office door, then the light rap on the doorframe, coupled with a distraught “Uh…Mr. Wills?”
I looked up and saw on of my students, Carleigh Simms. As I recalled she was the daughter of some gaziantep escortları immensely powerful and successful lawyer from LA who wanted his daughter to have a proper New England education. It was clear she had been crying for a while, because this girl, who was normally exquisitely put together in class — even with the limitations forced by the approved school uniform of wool skirt, knee-high socks, white blouse and cardigan sweater — came to me now with wet mascara streaks running down her face, her hair a mess, and blouse pulled out from her skirt. I had to admit that, in a strange way, she looked even more alluring like this than she normally did in class.
“Yes, Carleigh? What’s wrong?”
“Mr. Wills…uh…uh…,” she was having trouble speaking as the tears welled up in her eyes and she began to stutter, “I…I…I need your help…” She was crying and stuttering so badly I gently guided her to the other chair in my office and offered her some tissues, then sat back down at my desk.
“Oh?” I said, knowing full well she was here because of her grades. Carleigh was a very bright young woman, but the very worst example of what having the very best for one’s entire youth can do to a person. She rarely studied, and even more rarely did assignments given to the class. I believe she assumed she would be able to have Daddy make a phone call on her behalf or donate a library to the school or something and she’d get straight A’s. She assumed wrong.
“I told my Dad about my grades,” she paused, wept loudly, and whined a little, “and he said if I failed he’d take the Benz away.”
Oh, that snotty rich brat, I thought, She’s getting this worked up about a car?!
“Oh, well, that’s unfortunate Carleigh. But you do have to know that this is your own fault. You were very lax this semester, and really never took this class seriously. I’m sorry, but if you lose your car it’s your responsibility.”
This forced Carleigh into absolute paroxysms of loud weeping, and she literally threw herself on her knees before and clasped her hands together, as if actually begging for her life. “Please, Mr. Willis?! Pleeeeeease?!! You don’t understand, I love that car; I can’t live without that car! I’ll do anything I have to make up the difference, any amount of extra credit to get my grade up! Please, Mr. Wills, I’ll do anything!”
Now, I’d be lying if I said I never had any sexual thoughts of my students. Here I am, an eligible bachelor surrounded by several hundred young college women, all of which are in these sexy little uniforms, and almost all of which are Playboy Playmate hot. But I have truly never acted on these thoughts before simply because I know girls like these will not be interested in a 40-year-old professor of literature, no matter how fit and trim I am.
This, however, was a different situation. Between the site of Carleigh disheveled and begging on her knees before me, the cool spring breeze, and my own erotic thoughts, I quickly felt my cock grown thick and hard.
“So, Carleigh. You’d do anything to get your grade up?”
“Yes, Mr. Wills, anything at all.”
“Any amount of extra work, no matter how hard it may be?”
A surprised, yet somewhat intrigued look flashed across Carleigh’s face as she became aware of what I was talking about. “Yes, Mr. Wills,” she whispered with a naughty grin, “I can handle whatever you want to stick me with, no matter how hard it may be.”
I leaned back in my desk chair and thrust my pelvis out a little so the bulge in my pants could easily be seen. “Well, then, Miss Simms, I guess you’d better begin your first assignment.”
Carleigh looked at my bulge greedily and licked her lips, like a kid about to dig into a tasty treat. She crawled slowly to me, keeping her pretty green eyes on my cock the whole time. She stopped and kneed right in front of me, looked into my eyes and smiled as she started to slowly undo my belt and open my pants. I am one of those guys who just likes going without underwear, so as soon as Carleigh unzipped my pants half way my cock popped right out like a Jack in the box.
“Oooooh,” Carleigh cooed sexily, stroking it gently. “What a pretty cock you have, Mr. Wills. Looks like we were right.”
“What do you mean?”
“The girls in class,” she said, still stroking my cock slowly, looking at it lovingly. “We all talk about you and think you’re totally hot. We were all trying to guess how big your cock was, and we agreed it must be pretty big. We were right.”
Holy fuck! I thought. Looks like I could have been tapping this gold mine long ago!!
I was gently rubbing her soft red hair when the thought occurred to me: Here is this girl almost half my age, with enough personal wealth to buy me several times over, on her knees about to suck my cock. The wonderful disparity of the situation made me suddenly get even hornier as I felt like I was about to fuck a rich bitch, a snotty little brat, and perhaps feel like I’m teaching her a real lesson.
I grabbed her hair, and said, “Now, Miss Simms, perhaps you could begin your assignment!”
Carleigh caught her breath and smiled as I pulled her hair, and said, “Ooh, yeah, Mr. Wills. I love it rough!”
“Sir!” I answered. “You will call me Sir!”
“Yes, Sir!” She continued to stroke my cock slowly and gently for a moment, looking at with what appeared to be a hungry desire, and then ever so slowly licked the entire bottom of the shaft, from balls to head. She moaned softly as she did, and I felt like I was going to melt.
She slowly eased into sucking my cock, teasingly and wonderfully. She’d lick it from end to end, like a kid eating an ice cream cone, and then stroke it for a while. She’d lick the sides from end to end, suck on the head, and stroke it at the same time. She’d make sure to suck my balls as she stroked it. Then she finally, slowly eased the whole length of it down into her mouth until I could actually feel the back of her throat. It was obvious this girl had sucked plenty of cock before and knew what she was doing.
Carleigh had gotten into a nice regular rhythm of pumping my thick cock deep into her mouth, sucking it, then taking it out to stroke it and lick the head. She was driving me wild, and apparently she was enjoying it as much as I was given the deep moans she made every time it slid into her soft, hot mouth. I badly wanted to blow my load into her mouth, but I needed to stretch this out for as long as I possibly could.
“Get up,” I ordered abruptly, taking my cock and stroking it in her stead. “I want to see you naked. Strip for me, slowly.”
She looked at me deeply with her eyes, and slowly began to unbutton her blouse. She opened it to reveal two perfectly shaped, firm breasts supported by a lacey black bra. Carleigh sat gently, slipped off her saddle shoes, and then slowly rolled her knee-highs down her nicely toned legs. Turning around, she slowly slipped her plaid mini skirt down her waist, bending over all the way as it came off and giving me a lovely view of her tight little ass in the process, barely covered by matching black panties. Facing me again, Carleigh eased out of her bra, squeezing the most heavenly set of tits I have ever seen together and nearly making me cum right there. Finally, she sat again to slip off her panties, showing me a flash of a perfectly shaven, pink little pussy.
I wondered for a moment if she had ever performed as a stripper in her spare time, or perhaps as some kind of weird alter ego fantasy, but finally figured she was just an incredibly sexy little thing that knew how to turn on guys. God knows, she knew how to turn on this guy!
“Now stand, and turn slowly. I want you to earn your grade, Miss Simms.”
Her body was deep bronze from spending so much time at the tanning salon, so the tits and pussy area stood out in sharp white contrast. Her breasts were firm, young, and perfectly shaped, while her nipple stood out like little pink erections on her milky white breasts. Carleigh was slim but toned, with a shapely ass and a pussy area utterly devoid of hair. It look delicious and very edible.
She turned about with utter obedience and was clearly enjoying every minute of this as much as I was. She enjoyed being displayed as a sexual object, being treated as a sex toy, being ordered around and totally submissive. I could accommodate that desire.
“Now,” I said slowly, “get on all fours, and crawl to me, and beg me to suck my cock.”
Carleigh did as she was told, crawling to me as she kept her eyes locked on my swollen cock, looking like the most beautiful yet savage animal to walk the earth. When she had crawled all the way until her face was mere inches from my balls, she whispered huskily, “Please, Sir, may I suck your cock?”
I stroked my cock in front of her face. “I don’t know, Carleigh. I’m not sure you deserve it.”
“Please, Sir, please may I suck your cock? Please, may I taste your cum?” She was now leaning forward with her mouth open slightly, like a baby bird desperately wanted to be fed. I so wanted to stuff my cock right down her throat, but controlled myself.
“Are you a dirty little rich bitch, Carleigh?”
“Yes, Sir, yes I am. A very dirty little rich bitch.”
“Are you a snotty little rich fuck whore?” She was now panting hard and eagerly anticipating my cock in her mouth, sliding out her tongue to get even a slight taste.
“Yes, yes, I am, Sir. May I please suck your cock and swallow your cum?!”
I demurred for a moment, pretending not to care as I stroked my cock, even though I was actually almost ready to explode with sexual tension.
“You will have to pay for your impatience, but…I suppose you may suck my cock.”
With my permission she practically lunged onto my cock, diving onto it and swallowing the whole thing in one gulp. While she had previously been slow and teasing, she now pumped it hard and sucked it like my cum was the only thing that could keep her alive. She sucked my cock like a cum junkie needing a serious fix. Every time my cock pumped her mouth Carleigh would make this delicious little moan, making me want to explode even more than I already did.
I had stretched this out as long as possible, trying to make this blow job last. I used every trick I could think of, even imagining things like kittens and nuns and old granny tits. Eventually, though, Carleigh’s jack hammer-like cock sucking was just too much for me and I felt that delicious pressure begin to build deep within me, quickly flowing right up my cock, making my already hard, thick pecker feel like it was swelling to twice its present size.
I began to moan loudly and breath heavier, twisting her hair in my hand as my eruption approached. I felt my cum explode out of my cock and into her awaiting mouth and I screamed out in wild pleasure. As I did so I could hear Carleigh moaning loudly in time with my squirts, obviously loving the feel of my hot cum filling her mouth. My orgasm seemed to go on forever, during which time she never stopped stroking and sucking my cock to get every drop of cum she could. My screams eventually trailed down into grunts, then finally very satisfied sighs.
I heard her swallow my cum with several loud gulps, then sigh happily. She licked her lips and wiped her chin where a little of my cum had leaked out, then sucked it off her finger.
When I caught my breath, I said, “Well, Miss Simms, I would definitely say you have now earned a passing grade.”
“But,” I said with a tone of disappointment, “I don’t believe this level of work is more than about a C. Wouldn’t you agree you deserve at least an A?”
“Yes, Sir, I would agree,” she said with a diabolical look in her eye, perhaps anticipating what I was already planning on doing next…