Ellison eyed him from behind the wide varnished desk. This would be the time to invite him to have a seat if she was of a mind. She wasn’t. He was in his mid-twenties, a good decade younger than she, but still built like the athlete he must have been in college. Even six feet-maybe six one-no more than 200 pounds. Solidly muscled across the arms and shoulders with what looked like tight abs and strong legs. His hair was unfashionably long but clean and he had a tan and a smile that she was sure could and had melted coeds at Bryson. The khaki Dockers, moccasins, and light blue crew neck completed the picture.
He met her gaze when he came into the office but was now distracted. Ellison had left a riding crop on the corner of her desk-so far away from her that she couldn’t reach it easily without getting up but directly in his line of vision when he approached her. The crop was tightly wound and supple-with a small leather loop on the business end. The handle was wrapped leather with a wrist strap so that she wouldn’t lose it in action. This is where his attention was focused.
This is the time of the office visit where it becomes crystal clear to the visitor what he is doing there and the small flutter that he felt in his chest coming across the threshold increases to a gentle pounding.
“Take your pants off.”
“Take them down?” he asked hopefully.
“No, off”, she answered. “Course you’ll have to take your shoes off-do what you want with the socks, on or off, I don’t care. And underwear off. Naked from the waist down. Put everything on that chair over there.” Ellison gestured at a wooden chair beside her desk.
His hands wanted to shake a little as he worked at the laces on his shoes, but he kept them in check. Off went the shoes and he took off his socks and slipped them into the shoes. As he unbuckled his belt and unsnapped his trousers he watched Ellison out of the corner of his eye as she arranged the chair in front of her desk.
Ellison busied herself with the chair so she wouldn’t watch him undressing although she wanted to. It was a large overstuffed chair with big rolled arms. She slipped the ottoman from the front of the chair to the side-next to one of the arms. Even now, with his pants around his ankles and his thumbs in the waistband of his boxers he couldn’t stop himself from eyeing Ellison’s slender ass encased in her tight black jeans as she pushed and pulled at the furniture. Even in his current predicament, the sight of her bending over in front of him-it had to be on purpose-brought his cock to semi-erect life. Hopefully she wouldn’t see it. He folded his pants and placed them on the chair with the underwear on top. When he turned back to the chair, Ellison had placed a throw pillow on the seat.
She stood casually next to him-as if they were on a street corner waiting for a bus.
“This is a new set-up for me. You’re the first to try it.”
“Am I honored?”
“Thought it might be better than the old bend over the desk, deal. Especially for this one-since you’ll be getting a pretty strong punishment.”
“Really? Isn’t this my first offense?”
She was standing right next to him. If she moved her hand six inches to the right she would have been able to cup his ass-maybe rub and kneed it just enough to see if his cock would enliven a little more than she’d already noticed. And then what if it did? She felt a little rustle in her own chest as she stole a glance toward the floor to see if he was stiffening. She felt that if he was, she was in danger of putting herself into a serious misconduct situation.
They were all adults here; there was nothing preventing them from doing whatever they wanted off-campus or out of the office. But this situation-where she was required to wield the stick-such as it was-the lines were pretty strongly drawn. Only once or twice in the times she was in this position had Ellison veered into the forbidden zone. And she had regretted it both times. But this guy was tempting to her in a way that he didn’t know and she couldn’t understand. She calmed her voice to ensure there was no quiver when she spoke.
“Your first provable offense. The first you admitted to. I never questioned you about the other three that we discussed. I know you would not lie to me if I asked you, so I haven’t. Do you want me to ask you about those three other nights?”
Even with his eyes down, she could see his face flush crimson. This guy was something special-he was standing next to her smelling of shampoo and expensive aftershave, bare-ass in preparation to get his bottom whipped and he blushed at the thought of telling a lie.
“You don’t have to ask”, he said quietly. “It was me.”
He followed her directions and knelt on the ottoman-laying across the padded chair arm. The cushion on the seat supported his middle but the chair arm was the highest part of the assemblage and thrust his hips and bottom up and out. She watched from behind as he fidgeted to place his manhood, which had shrunken, into a comfortable position. This would be a better position for a woman-who didn’t need to deal finding a spot for the snake to lay. He used his hand to position it up along his belly and Ellison let him settle in actually feeling a little guilty about watching his tight bottom cheeks tense then relax as he slid his knees about shoulder width apart and exposing everything that he had to her.
That’s the way it generally was with men-at least with her. Women would bend over and hold their cheeks so tightly that you couldn’t slip a dime between them. At least in the beginning-until the paddle, or cane or strap or crop made writhing unavoidable-then they would show all in vain attempts to avoid the swats. Guys though-she was treated to the strong backside, the tight hamstrings and the balls hanging free between the legs.
“Simple rules, now that you’re situated. I will whip you until I’m done. You will take what I dish out. No reaching back, no covering, no getting up when you are in position-which you now are. You understand?”
“Yes”, he said, muffled, talking into the pillow.
Time to get started. She touched his right cheek with the leather tipped end of the crop and watched him jump a bit. It was just a twitch, but she smiled. It was always the way. With a quick draw and a snapping forehand she brought the crop down on the exact spot she had just touched; just above center on the right cheek. He gasped and dug into the arm of the chair. The second stroke was a little stronger, hitting the same cheek-about an inch lower. He didn’t jump but Ellison saw his back tensing as he tried to redirect the pain into his shoulders and back. She swung the third stroke short to catch the left-nearest cheek-dead center. He grunted loudly and spread his legs a little wider so he could push off his knees to further dissipate the pain.
That movement proved to be his undoing as he moved after Ellison had already begun her next stroke. She swung full strength meaning to strike hard in the crease of the left cheek-where the leg met the bottom-hoping to raise the first welt of the session. His slight movement opened his legs a little wider and the crop’s leather tip bit hard into the soft puckered skin of his backward peeking scrotum.
The pain registered like nothing had to this point-like nothing ever would. He thought sure that she had poked him with a cattle prod-or dropped a hot coal back there. He bucked backward off the chair and a gasp escaped his clenched teeth. Tears welled in his eyes as he slammed his legs shut kicking his feet from the knees. “Jesus!” he hissed.
She stepped back startled. It had happened so quickly that as she saw the crop dig deeply into his most sensitive skin she felt powerless to stop it. His buttocks were clenched tightly and his legs seemed carved out of stone. His back raised and lowered as he recovered normal breathing. Ellison put the crop in her off hand and patted his bottom-one cheek then the other.
“I’m sorry”, she said gently. “That’s why I need you to stay still, understand?” He nodded quickly as she moved slowly from patting to rubbing. There was one mark on his butt so far-not much to show-but she had to relax him before she could get back to it. “Don’t tense now-loosen up a little. It will be worse if you keep your bottom hard”. She stroked until his cheeks softened and his breath settled. Then she did something she had never done before. “Here-open up“ she fairly whispered as she put her hand between his legs. He slid his knees apart a little and, when she patted the inside of his thigh, a little more. Gently-almost clinically-she reached between and took his scrotum in her hand. He lifted a little to give himself a little freedom. She rubbed the small purple bruise with her thumb feeling the rustle in her chest increase to a roar. She always enjoyed the feeling of power being in this position gave her but this was something more.
She controlled her hand and her voice as she released him. “You’re OK. A little bruised-but fine. I’m going to give you another dozen or so then we’ll see where we are. They’ll be pretty hard, but can’t imagine they’ll hurt you worse than the last one. You OK with that?” She waited for it…”Yes M’am”, he said quietly as she smiled.
She took aim at the lower right cheek and let fly into the soft skin at the top of the thigh. He jumped. Then another in the same spot followed by a loud yelp. Three more whipping strokes dug deeply as he lost all inhibition about crying out. Each “thwack!” was followed by an “OWW!” or “Ouch!” each louder than the previous. When he first laid across this chair arm he was determined to suffer his punishment in silence. He especially didn’t want the girl in the outer office-to know what was happening in here. Of course she knew-but he imagined himself the strong silent type.
Ellison moved up the bum to the top-landing four hard strokes-“OW!” “WHIP!-AHHH!” across the top of both cheeks. The two on the right raised welts immediately-one hot pink and another tomato-red. She had the power to bring out deep purple weals-she had drawn blood in her day-but was doing enough for now. The next stroke bit deeply into the middle of his right cheek. “OWWWW!” he cried out and straightened his legs-thrusting his butt firmly into the air. Ellison obliged what looked like an invitation and stroked hard into the left moon. His cry was more of a grunt as he gritted his teeth and further tensed his body so that nothing was touching the chair but his chest and elbows.
She would normally pause here to let the subject relax and reset himself but that just dragged it out. She wanted to be as merciful as she could and at this point and she figured the easiest way to do that was to get it over with. She reached high and stroked hard into the center of his board-hard butt. He wailed like a bee-stung child and collapsed back on the chair arm and twisted. She hoped he wouldn’t cry-not so much for her but for him.
“One more”, Ellison said softly as he flattened back into place. “OK”, he breathed. His butt was criss-crossed with stripes and a few small red blisters where the end had bit deeply. Those coupled with the unplanned shot to his balls had made for a more unpleasant day for him than she had planned. She pulled back and stroked into the nearest cheek, if not gently, certainly not as hard as the others. He didn’t even jump-just relaxed and exhaled quickly. “Thank you”, he coughed, realizing that she had eased up on him. “It’s OK”, she said placing the crop on the desk, “you did well. Now stay put.”
He relaxed a bit and lifted his hips to reposition his cock which had begun to thicken as he struggled against the leather of the chair arm. Funny how fifteen minutes ago he was mortified at the thought of this woman maybe seeing his bare ass but now he could feel her eyes on him as she moved behind the desk and she was seeing more of him than anyone ever had.
He heard a drawer open and she walked back to stand to his left. He looked back over his shoulder to see what she was doing. “Worried?” she asked with a smile in her voice. “Curious”, he answered. She held up a small plastic bottle. “Aloe and vitamin E mostly”, she said as she squeezed a dollop into her right hand. “Relax now.” He put his head back down on the pillow as her fingers with the cooling gel touched his hot, tight skin. “ahhh…” he sighed. She applied the lotion liberally to all of the welts and bruises then generally rubbed it over his whole backside. “Better?” “Oh, God yes!” he answered. “Almost makes it worth it, huh?” she joked. “I wouldn’t go that far”, he said smiling into the pillow.
He felt her hand part his legs and he pushed backward to give her access but also to relieve the pressure of his growing erection which was pushing against the chair arm. Ellison’s fingers found his bruised scrotum and rubbed the cooling lotion onto what was becoming a very taut little bag indeed. When he moaned this time, it was less about the pain and more about the stimulation she was providing.
“Get up”, she said with a gentle pat on the rump. He pushed back to his knees revealing everything as he stood straddling the ottoman.