3. Dad's Dalliance
John Wooldridge was not aware about Sasha's new boyfriend, nor had Janice figured out when and how to bring it up, when they next talked. What she did realize, was that she was going to have to be the one to do it. Sasha would never have the courage. And, after the hot and sweaty noises she had heard coming from Sasha's bedroom when she fetched a glass of water last night, Jordan was definitely going to be staying on.
It didn't really matter given how little concern John Wooldridge had for matters on the home front. For at this very moment, he was on his sofa stroking his rather large and continually stiffening erection, while his free hand caressed the buttocks of his personal assistant Alicia, who had come to his townhouse to show him how well the new black lace lingerie he had bought her fitted.
She turned her head over her shoulder to watch him go to work, and he dropped his now stiff cock, which sprung around like a loose tent pole, and used both of his large hands to grab her perky buns.
He spread her cheeks wide to view her small, circular, anal port.
"Oh, my! Do you like it, Sir?" she played along. He nodded, approvingly.
Alicia didn't mind working for the director of the Montreal branch of law firm Wentworth and Johnson. After all, she was being compensated well for these out-of-hours activities. She did receive a copy of the monthly ledger, in which she noticed matching sums that were listed as building and contract maintenance, or official entertainment. Certainly apt ledger entries, she thought, seeing that she was definitely performing routine maintenance on a key feature of her boss's building.
She looked down and noticed that same building part, hard as rock, and heading for her pert ass. She reached her right hand up and cupped his cheek tenderly, looking lustily into his eyes, as his large white rod penetrated her flaps, and slid into her pussy. Alicia's body heaved in slow motion and her eyes rolled into her head as John began his slow, steady thrusting.
"Oh, yes, Mr. Wooldridge! Fuck me, Sir!" She loved being his little muse, and using suitable language. It was a huge turn-on for him, and brought him to orgasm quickly.
As he continued to pound her pert ass, watching the folds in her tight tanned back, John wondered how much longer he could keep up the charade. Of course, Janice knew. All the wives did. It wasn't really his fault. Alicia seemed eager, and had been happy to accept his approaches at the office. Once she saw the extra pay, and the size of his dick, she had really been initiating most of the opportunities herself. So he could truthfully say that she came onto him.
His favorite session, and their most naughty, had occurred inside his office. The other staff had been present, but they already understood what the closed door meant. He was not to be disturbed. She had locked it, just to be sure. Then she had dropped to her knees, picked up the file in her teeth, and slowly crawled it on all fours around to his desk. It wasn't easy in her very tight dress, but the awkwardness enhanced her 'helpless female' routine.
As she reached the desk, Alicia disappeared, then he saw her coming around the corner, still holding his file. He had an eyebrow raised, and couldn't help a smile. This was one girl who knew who to play her part.
She reached up on her haunches, placing the file on the desk and adjusting it with her nose, as if her front paws weren't capable of such dexterity. Then she sat on her haunches and turned to him. Her forearms reared up with her wrists limp. She pressed her chest forward and stuck her ass out, and otherwise mimicked a puppy dog as best she could, showing him her big eyes. Her tongue was hanging out, and she was panting, noisily, with a big smile.
John had enjoyed the view for a few moments, then decided he would play a power move. He glanced at her once more, then took the manila folder from his desk, opened it, and began perusing the contents. She was still there, tongue out, panting. After a further minute of this, she couldn't wait any longer, and went back to her paws, and crawled beneath his executive legal desk. He paid no attention, and was now (at least pretending to be) engrossed in the file.
Alicia decided to portray her puppy dog role as accurately as she could. She reached up, and began nosing into his crotch. He shifted around in the chair to become more comfortable. She continued working, bringing herself up to rest her forearms on his thighs, and nudging his office chair back slightly so her head had room to appear beyond the desk.
Then she went to work with her tongue. Licking his suit pants in long strokes along the line of his penis, as far as she could determine. It was all folded up inside his package, and not obvious at first. Then she found the tip, which had begun to unfurl itself like a flower seeking the sun, and gave it her full attention.
John was making progress reading his file, but could see that his secretary was not going to get very far if she restricted herself to puppy dog movements. He was getting hard, so he paused momentarily to unbuckle his belt, and unclip the top of his trousers.
His 'pet' looked up at him gratefully, panting and showing him her tongue. She then gripped the flap with her teeth and turned her head to unzip it the rest of the way. His bulge increased as his underpants found room to move. She used her nose and mouth the grab the edge of them, but couldn't stretch them over his thickening cock. She licked his pants until the color of his head was visible through the wet, white material.
Then he sprung out. His penis was large enough to break the seal of his pants to his skin, and the first few inches were visible, his tight red he8ad looking desperate to be cooled down. She clenched her teeth together in a triumphant snarl and growled up at him, before approaching and licking the tip. He finally acquiesced and moved his trousers and pants down around his ass, so she could gain free access to his cock.
She reached up on her hind legs like a hungry dog, and extended her mouth down over his member and beginning to bob slowly. Up. Down. Up. Down. Her long strokes took almost the entire length of his cock until it was squashed against the back of her throat and she receded.
She took the tip in her teeth, and brought it down to the horizontal, so she could suck along his shaft while looking up at him. He moved his file briefly to gaze down on her, and she passed him a warm smile. He returned to his papers. A few moments later, his girth increased slightly, and she could feel his throbbing. She was succeeding. He was going to cum.
Then, he abruptly threw the file on the desk, and stood. Grabbing his cock with his right hand, he began stroking the soft fleshy underside to bring his erection to climax. Alicia returned to her begging position, tongue out, eyes open expectantly, paws up.
Her cute ass was sticking out of her tight dress. When he saw her looking up at him like that, his body could only respond in one way. He produced one of the greatest cum shots of his life, hosing her mouth down with his white cream. It was a thick, continuous flow, and her little mouth was full to the brim in moments, it spilled down her neck and onto her dress, and his final squirt caught her upper lip, and landed on her nose.
She looked up at him like a faithful puppy, hoping to have won her owner's approval. She swallowed his load, and then continued to hold her tongue out, still dripping his gene fluid onto herself. He sank down in his chair, exhausted. It was incredible, but exhausting nonetheless. He didn't have the stamina he had had when he was twenty-five.
Fortunately, there was a powder room connected to the main office entry, so Mr. Wooldridge sent his secretary out to clean herself up, before returning his clothes to their proper place and continuing with his work. He would need to deal with her eventually.
Alicia's response to his approaches was amazing, but also dangerous. Surely the others knew by now. He wondered if she was being extra needy and submissive to keep him coming to her, and not start anything with the other secretaries or a junior law clerk.
From Alicia's side, John's assessment of her had been quite correct. She had seen him as her pathway to future status. A secretary wasn't going to get very far on her own, but the wife of a prestigious law firm? In a league of her own! She had previously planted seeds of going away on a work trip with him, and other future plans, so he definitely knew the way she was steering him.
If she could turn herself into his future trophy wife, she could use his money, give him all the love he needed to satisfy him, and still satiate herself with younger men, when the time came that he was too old to get it up. The big house, the glamor, the ballrooms, the Ferraris...it was just all too much to think about at once. The main issue was the current wife. It seemed they had drifted apart, he hardly mentioned her, or his kids, for that matter. She decided that if she let him fuck her every time he was on, that would be the quickest way for him to realize that his old wife had to go.
John Wooldridge, for his part, was warming to the idea of a trophy wife. He knew Alicia had to be angling for something more than illicit sex and affairs. She wanted the money and the fame that came with being an important man's woman.
