Jack Bradley Meets His Match

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Status: Finished  |  Genre: General Erotica  |  House: Booksiesilk Classic Group

All names are fictitious, except for Kentucky, of course.

Jack Bradley Meets His Match

Franklin University in Camelo, Kentucky, wasn’t a reformatory school, nor was it a full-blown military academy, but it lay somewhere in between. It catered to wealthy clientele whose adult children might require a stricter regimen than would be offered by the more liberal universities. There were curfews, bed checks every night, and punishments for the less than ardent students. The grounds were pristine, as were all the on-campus buildings and dormitories. Frivolity was held in check, and free thinkers were verbally beaten down until they saw the conventional ways of their parents as the only path to success. It was an all-male school.

The university offered degrees in management, business, and financial strategies. The student body was composed of young men expected to enter the family businesses and eventually become CEOs, company Presidents, or Chairmen of the Boards.


Diana Dunne was the first female Chancellor selected to lead the university. Under her tutelage, admissions had increased 5% per year for the six years since her hiring. She was chosen for her strict moral attitude, her vast experience in leading various schools to profitability, and her understanding of the talents required to be a successful business owner and leader.

Diana had a somewhat pear-shaped body type, though her breasts were larger than the average pear. She had wide hips but narrow thighs, leading many to think she was heavier than she actually was. She had a manliness to her face with a square chin, slightly larger nose, and bushy eyebrows. With makeup, she could highlight her more feminine features like her eyes, cheekbones, and full lips. Overall, she was pretty in her own right. At one point early on in her tenure, she asked one of the faculty members what the students thought of her looks. He had said they thought she was a handsome woman but not one to be trifled with. Whether he meant it as a compliment or not, that’s the way she took it.

Diana had never married. Experiences in her late teens and early twenties left her with a distaste for intimate relations. Back in college, she was more of a wallflower, and with stiff competition from other girls, her interest in men went from mild to apathy in two years. The only sexual experience she had was with an intellectual who might have been considered ‘slow’ if it wasn’t for his IQ. In matters of sex, he was a complete dunce. Their only attempt ended with him barely penetrating her and then pulling out before his orgasm. He had not stimulated her enough for her to find any real enjoyment in the encounter. The reason she considered it a good date was that they sat and talked for hours afterward on all kinds of educational topics. That is what she found pleasure in. She had spent hours studying about ‘hook-ups,’ but not the ‘how to,’ so she thought that all sex was pretty the same, leading to sex being taken off the table.

When Diana started at Franklin at age fifty-five, she ran headlong into menopause. She was thankful for having ended the previous stage of her life. Other than the hot flashes, she could ignore the other changes she passed through. But, bodies sometimes can render decisions invalid, as she was about to find out.


It was early September, and school was still in its first semester. Diana looked out her large office window into the quad between classroom buildings on the left and dormitories on the right. In the middle sat a fountain. Maintenance and janitorial services were busy draining the fountain that now had blood-red water running through it. Somebody during the night had put dye into the fountain as a prank. Franklin didn’t allow pranks. Her duties at that moment were quite clear. Inform the perpetrator that his actions were unacceptable and he would be expelled. She was smiling to herself. This had to be her most favorite part of being Chancellor; even her body tingled from the anticipation.

There was a knock on her door. She didn’t bother turning around. She didn’t want to show her gloating face until the precise right moment.

“Come in, Mister Bradley, and please close the door behind you.” Her voice was stern and with perhaps a bit of malevolence.

Jack Bradley was twenty-two and 5’ 9”. He was, by any standard, a good-looking young man. He was naturally slim but had enhanced his frame through weight lifting, track and field in high school, and yoga classes. If the truth be known, the latter was so he could both, see the young women at play, and be seen. He wasn’t much of a charmer, preferring the ladies charm him. He did have a swagger to his movements and a confidence that was best used to overcome objections to his often sexist behavior. It wasn’t that he didn’t respect women; it was he respected them for all the wrong reasons.

Jack also had done his research about Chancellor Dunne. He learned a story from her secretary about Larry James, one of the athletic coaches, who tried to persuade Diana to partake of some of the more basic human behaviors in her office, even going so far as having stripped naked. The secretary had interrupted them because Diana pushed a panic button under her desk. The coach was fired, and Diana banned anyone from ever discussing the manner. Diana confided in the secretary that her body had responded upon seeing the naked man’s erection and asked her why, if she wasn’t interested, she had reacted. The secretary told her that it probably occurred when she was having a hot flash and had nothing to do with Larry James.

After closing the door and turning the lock, Jack walked over behind Chancellor Dunne, placed his hands on her shoulders, and began to gently massage them.

Without turning around, Diana said, “Mister Bradley, you are standing too close. Being nice to me isn’t going to help you in this situation. Pouring dye into the fountain is considered a major breach of Franklin’s policy. And…”

Jack interrupted, “It won’t be fair if you don’t at least listen to my defense, Chancellor Dunne.”

Jack continued to gently massage Diana’s shoulders. Though she had explicitly mentioned he was invading her personal space, she hadn’t yet forced him to stop. Realizing she was starting to enjoy what he was doing, she said, “Mister Bradley, this is most inappropriate and uncalled for. Please take a seat.”

Instead, Jack stepped forward, pressing his body against her’s and pushing her pelvis against the wall below the window. As his abs met with her backside, the bulge he was now sporting, pressed her skirt in between her cheeks. Through his hands, Jack could feel a shutter flow through her body all the way down to the front of his pants.

Diana said, in a slightly higher and strained voice, “This has got to stop, Mister Bradley.”

Jack thought he could feel her push slightly against his body. He now played his ace in the hole. He leaned his head next to Diana’s ear and whispered, “Miss Dunne, tell me about Larry James.”

Diana’s heart almost stopped. She started to lean forward but standing against the wall, she realized that would push her body harder against his. Instead, feeling woozy with weak knees, she brought her shoulders back into his chest while tilting her head until it practically lay next to his ear.

Jack took the opportunity to slide his hands under her arms, half holding her up and around in front of her chest, just below her breast. He then proceeded to rake his thumbs along the underside of her bra, gently pushing in. As he turned his hands to cup her breast, he could feel her nipples had grown hard despite the utility of the materials to prevent such things from showing.

Diana’s first thought was to ask him how he knew about Larry James, but the distraction of his fingers slowly rubbing her tits had short-circuited her ability to speak. Her insides were igniting into a fireball.

Jack, taking her leaning on his shoulders as a sign of approval, quickly unbuttoned her blouse, reaching to pull it off her shoulders and then down her arms. He held it out to her side and dropped it onto the floor.

Helplessly, Diana watched as it drifted downward. Whatever confidence and controls she had were now evaporating off her body and melting away like so much steam. The fuse of forty years of pent-up sexual dynamite was slowly burning down, headed toward an explosion.

Jack brought his hands down to her waist. While she leaned back against him, he easily lifted her hundred and twenty pounds off the floor, turned to the left side of her desk, and set her down while continuing to press his hard body into her cheeks. Next, he reached between his chest and her back to unhook the eyes on her bra, bringing the ends out to her side. Slipping the shoulders straps down her arms, he flung her bra across the desk in front of her. He replaced the cups of the bra with his hands and began to knead her breast and nipples.

Diana stared at her bra lying just inches from her reach. To reach for it, she would have to bend forward, and that would cause her to press back against his rigid member. The desk was pressing against her stomach as he was pressing against her rear. The oddest thought leapt into her mind. ‘I’m stuck between a rock and a hard place.’ She would have laughed if she could have found her voice. Her breathing was labored from her body’s increase from excitement. Jack continued to massage her breast, and her nipples ached with pleasure as he twirled them back and forth.

Forcing her mind to ignore her physical reactions, she reached the point where she could talk, abate, in a strained voice. “M-mister Bradley, this is quite improper. Y-you w-will gain nothing from treating me like this.”

“Wrong, Chancellor, we will both gain. Me, the experience of what an older woman is like, and you, what a man with expertise in sex has to offer.”

Removing his left hand from her breast, he reached down and pulled the zipper on the side of her skirt.

Jack said, “I always love to see what kind of underwear a woman chooses. It tells so much about their secret personality.”

Diana had the unfortunate habit of buying the skimpiest type of panties. She justified it by telling herself it was simply an experiment. She had chosen a black thong, knowing she would be expelling Jack Bradley. At the time she put them on, she felt a kind of satisfaction knowing he would never know. All she could think now was ‘shit.’

Jack slipped her skirt down to the floor. He surveyed her ass. He admitted that she had beautiful skin. Soft and smooth like a baby’s behind. Running his hand over each cheek, she felt hot and almost electric to the touch. As he hooked a finger underneath the narrow swath of cloth that passed as cover for her butt, she moaned loudly when his finger crossed her anus. Taking that as an invitation, he slipped his finger, first in her pussy, to moisten it and ever so lightly into her butt. Again, she moaned.

This was all new to Diana. She tried to imagine it hurt, but her excitement increased each time he touched her rear.

Next, Jack hooked his fingers in the minuscule waistband of her panties and pulled them down, letting them drop to meet with her skirt. He gently grasped her shoulders and pushed her forward onto her desk. She could barely feel the coolness of the desktop as her hot nipples pressed against the dark wood.

Diana was completely naked now. She realized there was only one thing she could do to stop what was happening. She could easily reach her panic button, and her secretary would come running in. As she reached back under her desk, she heard his zipper. Her mind immediately went to the hardness of his dick. In her experience back in college, that dick had been kind of stiff but wobbly. Mister Bradley’s certainly seemed to be much harder, if not bigger. She knew they varied. She thought, ‘What the hell am I doing? I’m being forced to have sex. I need to call for help. But then what?’ It wasn’t someone else naked; it was her. In her convoluted state of mind, she decided it would be better to have him caught in the act. She had had sex once; she was sure it would be the same anyway. After all, how could it be anything but the same? She would wait for the right moment. He wasn’t hurting her, she felt he might be a scallywag, but he wasn’t a violent man.

Jack unbuckled his pants and let them fall to the floor, immediately followed by his shorts. He had to stand back a little to give himself room to aim properly. He placed the head of his cock at the entrance of Diana’s pussy.

As Jack pushed slowly forward, Diana said, “Oh my god, Mister Bradley, it’s not going to fit.” She desperately started to press the panic button under her desk, but nothing happened.

Jack leaned forward, still pushing his cock into her, and whispered, “I had Anna turn off that button Chancellor; it’s just you and me until we’re finished.”

“Okay, okay, but…but if it doesn’t fit, then you have to stop,” Diana said through clenched teeth. Her first reaction was to the pain, but then pleasure began to flow over and obliterate that notion. She changed from ‘this can’t happen’ to ‘this can’t stop’ in an instant. She could feel her vagina stretching. It was both uncomfortable and extremely pleasurable at the same time. Finally, reason began to reassert itself. “Look, Mister Bradley, let’s make a deal. I’ll forget about expelling you if you stop doing what you’re doing.”

Jack said, “Miss Dunne, it’s called fucking, and most people enjoy it.” He continued to push his cock deeper and deeper as her pussy stretched to allow for its size. “Anyway, if I stop, I wouldn’t be satisfied, and you wouldn’t orgasm. When was the last time you had an orgasm, Chancellor?”

“College, I think, and it wasn’t nearly as pleasurable as this, but still, this is improper. I promise you I’ll keep my word.” Diana said.

“No thanks. What I will do is, once I’ve gotten it all the way in and shot my load, I’ll stop even if you haven’t had an orgasm.” Jack then asked, “Is that fair?”

Diana’s eyes started dancing back and forth as the pressure of an orgasm she had never felt before built. “That’s not…no…I…can’t think straight. What do you…mean…all the way…in?”

Jack said, “As in up to my balls. Got maybe two, three more inches to go. I think you can handle it.”

“Oh shit, Jack!” From there on out, for the next five minutes, all Diana could do was moan and shake. Then suddenly, it was like a dam had finally broken under the strain of forty years of denial. Diana collapsed on the desk, not having enough strength to move.

Jack kept stroking her, working every inch he had left to get his whole cock into her before cumming, but he didn’t cum. Diana had become so wet that he couldn’t get enough traction to stimulate his throbbing cock. He said, “Miss Dunne, you’re too wet; I’m going to have to use your ass to finish.”

Diana’s eyes flashed open. “Oh god, no. There must be another way. Anything Jack, but not that.”

Jack asked, “Anything?”

“Yes, Jack, anything.” Diana thought he might want money or better grades.

“Okay, Diana, may I call you Diana? Sit in your office chair. I promise, once this is done, I’ll gladly leave both your office and the university.”

Diana saw she was going to get the best end of this deal. Having had a life-altering orgasm and now getting rid of Jack Bradley. She was euphoric. Jack helped her to her chair. Her energy level was quite low. She needed a rest after their tryst.

Jack turned to face her, his cock still as hard as it had been all that morning. He stood in front of her and, reaching forward, took her right hand and placed it on his cock. He started her hand in motion, slowly moving it back and forth.

This was only the second time she had handled a cock. Jack’s was hard, but the skin was soft. He inched closer. As he did, he placed his hand on the back of her neck.

Diana’s looked confused. If he kept holding her head, his cock would end up in her face. Somewhere in the back of her mind, clouds of a foggy concept began to clear. The word ‘cocksucking’ came barreling into her consciousness. Looking up at Jack, she could see in his eyes what he was expecting. As she slowly stroked his cock, she weighed her options: Having her ass ripped apart by this monster cock, or sucking on it until Jack had an orgasm. She chose the lesser of two evils. An unexpected desire rose up in her. If having his cock in her pussy made her explode in such a massive orgasm, maybe sucking on him might be pleasurable too. She didn’t want to appear eager, but she wanted to suck him.

Diana began to focus on the task at hand. First, she stuck her tongue out to gently touch the skin on the head of Jack’s cock. Feeling its super softness, she found it a pleasurable sensation. It was no longer Jack Bradley standing in front of her; it was a cocksucking dream she didn’t know she had. Trying to get the whole head in her mouth was quite unique, unlike no other experience in her life.

Jack still had a hand on the back of her head and kept lightly pushing, encouraging her to take more into her mouth. From her college days, in moments of social engagement, she had entered several eating contests. She was a natural. She found she could easily swallow whole foods without having a gag reflex. Keeping it down was a different issue. She had never lost that talent, and now it was coming in quite handy. She was having a great experience realizing that cocksucking was the crème de la crème of French kissing. The taste wasn’t bad at all, and the smell seemed familiar to her.

Jack had gotten all nine inches into Diana’s pussy before it became saturated with her juices. After that, he couldn’t generate enough friction to bring on an orgasm. Whatever her pussy lacked, her mouth more than made up for. The intensity on his cock rose sharply as she pressured his cock between her lips while sucking as hard as she could. The skin on the head of his cock had become so sensitive that he thought he would scream in pain. It was beyond anything he had ever experienced. As he reached the point of no return, he vowed to have this experience every chance he could, even if it meant begging for it. He then exploded into her throat. As she pulled back, his cum began to expel itself from the corners of her lips. As she pulled off of him, he threw ropes of cum all over her face, her hair, and down her breast. It was more than he had ever shot at one time. But his cock won’t go limp.

Diana wanted to see just how much of Jack’s cock she could take. This was no longer an unwanted advance from a scallywag; it was now a middle-aged woman sucking on a young man’s cock for all it was worth. It was alive and throbbing in her mouth. The thought of his orgasm had completely left her mind. All she wanted to do was suck. It didn’t take long for her to discover what happens when a man reaches orgasm. Suddenly his cock seemed to swell in her mouth to such an extent it made her throw her eyes wide open. Then it got crazy. He exploded. The first two shots went right down her throat with such force it pushed her head backward despite his hand holding her. The next few filled her mouth and began to seep out the corners. His cum tasted different from the first taste she had gotten when she started sucking on him. She realized that it was her own pussy juices covering his cock that she licked off. She then pulled his cock out of her mouth as he continued to throw rope after rope of cum into her face, hair, and down the front of her body. His cock remained as hard as when she first touched it with her tongue.

Jack leaned back against Diana’s desk for support. “Diana, that was the fucking best blow job I’ve ever had. Where did you learn to suck like that?”

Diana said, “Jack, let’s make a new deal. You fuck me again, and I’ll suck you off again.”

Jack’s eyes almost popped out of his head. “Anything you want, Chancellor, you’re the boss.”


Jack Bradley entered his dorm room at five o’clock. His roommate, Gary, was studying at their shared desk.

“Well, Jack, how did it go. You want me to help you pack?”

“Nah, Gary, I’m still enrolled.”

“Really, I’ve seen them expel guys for littering. How’d you get so lucky? Wait a minute, you fucked her, didn’t you.”

“Gary, Gary, Gary, not everything is about sex. Anyway, you’re going to have to find another roommate.”

“Where you going, Jack. They won’t let you live off campus. You’ve found another roommate?”

“Sort of; I’ll be moving into the Chancellor’s residence.”


The end

Submitted: July 25, 2022

© Copyright 2022 orangeistheneworange. All rights reserved.

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Add Your Comments:



This was an excellent piece, slowly taking us through the entire seduction right into the sex. Wonderfully described, perfect pact and a credible experience for both characters. Nicely done as they say.

Mon, July 25th, 2022 1:49pm


Thank you, and for the compliments. Glad you enjoyed..

Mon, July 25th, 2022 8:58am

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