Senior Moments

***Mr. Howe appears in my Lyla series. This is part of a planned series of spin offs featuring characters from the "In'DaMan'd" Universe.***

*****

"You know where you are going Carlos?" Mr Howe asked from the back seat of the luxurious car.

His chauffeur and assistant Carlos looked at him in the mirror and nodded politely before adding "Yes Sir."

Mr. Howe looked at Carlos and wondered how he had been so lucky to find him in this time of his life, he was very respectful and professional, rare in someone of only twenty one, relieved that he remembered all of his needs and sometimes eccentricities. At seventy years of age he would be the first to admit that he was not the easiest man to get along with, never mind work for so he was eternally grateful to his helper, though he would never tell him that. He believed in professional boundaries. Well, he thought he believed in them until Clarke Bentley had called him out of the blue, begging for his knowledge and experience in the business world, he had gotten himself into a royal mess and needed his help to get out of it. He of course told him he would think about it, Clarke had been one of his most promising protégé's but he felt that world was behind him. Until Clarke decided to play dirty and send that filthy blond Lyla to his door.

He wasn't expecting that under handedness from Clarke but years at the top of the technology field had obviously turned him ruthless, he could have refused Lyla's advances but how many men of his age could turn down a big breasted bombshell. He still vividly remembered their encounter in his green house. She had sucked his cock like a vacuum and then she did something that he had not experienced before, she stuck her tongue up his ass hole. Once he slid his cock into her tight pussy he knew that there was no way he could say no. The fact that he had agreed an hour before Lyla arrived was done to show Clarke that there was still a devious streak in him that had not wavered with age.

The car wound slowly through the down town traffic, he adjusted his dinner jacket, he could feel the invitation to dinner stabbing his hip through his pocket. It had arrived at his house three days ago. Ruby, his old flame from college would never dream of sending him a text or an email. She was old school and wouldn't change now. They still spoke on the phone a few times a year, usually exchanging advice on new business trends, or if anything interesting popped up that day in the stock exchange.

They had a hot and heavy relationship for a brief period in their college years but both decided that they were better off as friends, sometimes he wondered if she wasn't the one that got away. He began to readjust his suit pants, the heat was making everything stick to him and he was becoming irritable.

"Can't you turn up the fan any higher Carlos?" He snapped.

"It is at the highest Sir, I have left a hand fan in the back seat console if you would like to try that."

"Yes yes I seen that, I think it makes me look silly."

"Rest it on your lap pointing upwards and no one will see Sir." Came the reply.

Mr. Howe did as instructed and once again was reluctant to admit Carlos was correct, all these thoughts about Ruby was getting him down, he had not seen her in years and was apprehensive about meeting her again, the invitation was vague in regards to what the dinner was about.

"What do you think of the new gardener Sir, she seems pretty passionate." Carlos asked without taking his eyes off the road.

"It is almost like a sixth sense you have Carlos, you know when to distract me."

Carlos chuckled softly.

Mr Howe looked into the plastic blades of the fan that was whirring almost hypnotically. He had always appreciated sex but throughout his life he had always put work first, the feeling of blue that had come down over him the past few weeks was strange. He hadn't realized before but he wondered if he wouldn't have been happier with a wife and a few kids rather than the board room. He blamed Lyla, she was responsible for his recent sex drive resurgence.

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He sat back in the chair and remembered the first night he had spent with Ruby, they had both just started out and he had so desperately wanted to impress her. He knew that when he spotted her in orientation that first day of college that she was special, she had an elegant grace about her but a mischievous glint used to twinkle in her eye. He was too nervous to approach her, all the guys in his year were crazy about her but she never seemed to be going steady with anyone. They were in a few of the same classes and as fate would have it one day they were paired up for a business project. She had flung herself into the chair on the opposite side of the desk from him and let out a big sigh.

"I can't believe the amount of work we have to do." She said, exasperated.

"Yes I agree but it makes up half of our grade."

"I suppose, I'm Ruby by the way, nice to meet you..."

"Robert." He had replied, his mouth going dry.

"Well Robbie what you say we go off campus and have some fun before our whole month becomes numbers and totals."

He was always a good student but something about her aura told him that she would loose interest if he said no. They hopped in his car and drove to the beach a few miles from campus, when they parked she quickly rolled down her window and took a deep breath of the sea air.

"I don't want to spend another minute in a stuffy classroom."

They did this trip about once a week, it broke up the monotony for her and was the highlight of his week, getting to spend one on one time with the prettiest girl on campus.

When they finally finished and submitted their project it was a freakishly hot day, the beach was swarmed with families, he looked at her while her eyes were closed in the mid day sun, she was stunningly pretty. Her full lips jutted out from her pale face, he could see a trickle of sweat run down the nape of her neck. Her breasts heaved against her t-shirt as she panted in the hot car. He couldn't help himself he reached out and tucked a strand of her brown hair behind her ears.

Ruby's eyes flickered open and she just gazed at him.

"Do I make you nervous Robbie? You don't seem like other guys."

He swallowed hard, he had not much experience with girls in the past and definitely not with someone like Ruby. She laughed at the nervous look on his face.

"I was just teasing, I find it really nice that you are a gentleman. If you wanted to kiss me I wouldn't stop you." She said rolling the window down further.

Robert moved so quickly towards her that he forgot that his seat belt was still attached, a loud yanking noise and a searing pain in his throat snapped him back to his senses. He could feel his face flush red hot before they burst out in loud laughter.

She patted his knee once the laughter had died down and she had wiped the tears from her face.

"Would you like to try that again." She whispered.

He nodded bashfully and un-clipped the belt. He slid towards her cautiously. Their eyes never leaving each others, he grabbed the side of her face gently and placed a soft kiss upon her lips. When her pulled away from her, her eyes were still closed and her lips were still pouting.

"My roommate is gone for the night if you wanted to come in for a while."

He didn't reply he just turned the key in the ignition.

***********************

"I am so sorry boss, there seems to be a major accident up a head we are going to have to take the long way." Carlos said from the front seat.

"That is quiet alright we left with plenty of time to spare, just message Ms Kennel and let her know that we might be late."

Carlos opened the contacts on Mr. Howe's smart phone and began to scroll through them.

"I am not seeing a Ms. Kennel"

"She will be under Ruby." He replied tartly and re-positioned the fan closer to his face.

He rested his head back on the seat and started out the window, he rubbed the seat belt and smiled to himself.

He had dropped Ruby at her house at the end of each of their outings but had never been asked in. He pulled up to the driveway of a small two storey house. A banister started near the door and rose the whole length of the back.

"It's small but cheap and close to the college." She said as she grabbed her back pack and got out of the car.

Robert's hands began to sweat as he followed her into the door underneath the banister. The house was all in darkness and mercifully cool. The vertical shades had been drawn, the street light from out front cast a strange orange glow over the small sitting room. Ruby set down her back pack and grabbed Robert's hand gently guiding him down a small corridor and into an average sized bedroom. She kicked off her shoes, the short denim skirt she was wearing rose up slightly as she sat on the edge of the bed.

"I know I seem like a bad girl to you Robbie but sometimes I just need release and relief from all the studying. There is only so many times that a girl can self pleasure you know. Robert stood in the door way still in doubt that this was actually happening. He could feel his member stand to attention against his drainpipe trousers.

"Don't look so scared Robbie, kick off your shoes and come in." She said as she leaned over and switched on a bedside lamp.

He slid out of his shoes and closed the bedroom door, he moved in front of her but didn't sit down. He gazed longingly at her, the light from the lamp cast her in a beautiful light.

"Have you ever had a blow job before Robbie?" She purred as she walked her fingers slowly up his leg, from knee to waist.

He swallowed hard, the voice in his head was screaming to take her and fuck her like she had never been fucked before, make her never forget the great Robert Howe but his mouth had forgotten to speak.

Ruby stared at him with carnal intensity as she opened the button on his pants and slowly undid his fly. She yanked the pants down to his thighs, he felt unworthy and was starting to feel weak as she began to stroke him through his faded white Y fronts.

"Don't be nervous, I like you Robbie and I feel that you like me, just relax and we will have some fun OK?" She said as she pulled her top up over her head, her full breasts flopped down gently.

He jerked his head quickly in response.

***********************************************

A blast of a car horn snapped present day Robert out of his rumination.

"Everyone is so impatient, Ms. Kennel replied Sir, she is also running late and is looking forward to your dinner."

"Thank you Carlos." He replied weakly, the thought of his sheepishness at his first sexual encounter had side swiped him, he hadn't remembered that version of himself in years. Not since he became such a shark in the corporate world. He settled back into his seat, the leather boiling hot in the sticky heat and once again looked out the window, his cock gave a jerk as he remembered entering her mouth that night.

She had grabbed the base of his five inch cock and pinched slightly, within seconds he was fully hard. Her lips slowly snaked down the length of his cock before pushing against his tight ball sack, he placed one hand on his ass check and arched his back, his other hand was placed gently on the back of Ruby's head. His toes clenched into the carpet, he glanced down and seen that her eyes were closed and she was focused only on sucking his cock, the light from the lamp cast over her silky smooth skin. Her erect nipples casting a slight shadow on her C cup breasts.

She removed her mouth off him and slid out of her skirt, she was wearing big white satin panties. She jerked him off while she guided her own hand between her thighs. Her tongue lapped at his head, it took all of his focus not to show her how inexperienced he truly was.

"Your turn." Ruby said lying back on the bed and spreading her legs.

Robert stood there momentarily stunned before he quickly undressed and sank to his knees in front of the bed. He kissed up and down her thighs slowly, she moaned under his touch. He rubbed her opening through her panties, he was surprised at the warmth. He pulled them across slowly revealing her gash. He grabbed her hips and moved her closer to the edge of the bed and turned her slightly towards the lamp. He could see her in all her glory now, legs splayed before him, her pussy was darker than the rest of her body, it looked like a soft peach surrounded by a dark bush. He had seen pussies like this only in the magazines his father kept on the top shelf in their garage.

He did a zigzag shape up and down her gash with his nose, rubbing gently off her sensitive fold and breathing in her intoxicating aroma, her wetness glimmered slightly in the light, he padded his tongue flat and slowly began to lap her opening. Ruby's hand was slowly kneading her clit as he slowly and sensually licked her out. She rested her feet on his shoulders and slowly began to rock her hips on to his eager mouth. His cheeks flushed with concentration as he was determined to come across as confident and experienced, they both knew that he hadn't had much one on one time with the opposite sex but neither said anything. He gently took one of her flaps between his lips and tugged it slightly, a moan escaped her lips. She guided his head back to her twat and pushed him in and out of her, he was making slobbering noises as she became more moist.

He extended his fuck you finger and teased her pussy, he slipped it in to quickly and Ruby jolted.

"Maybe leave the finger until next time, you are doing a good job without it."

His face felt like it would melt with the embarrassment, he didn't make eye contact with her just continued to munch her box. Robert started to stroke his cock, he felt that it was getting close to that time, he hoped and prayed that he would last long enough to satisfy her. Sure enough she tugged his hair soon after he started pulling himself, he rose between her legs, bending over her beautiful body he snaked his tongue up her, stopping at her breasts. With his free hand he began to massage one while he flicked his tongue against her erect nipple rapidly. He felt the breath leave her body, she was biting her lower lip, her eyes screwed up tight. He was spurred on by her body language and sloppily kissed her neck, he took a deep breath through his nose, sweat mingled with her perfume.

Ruby ran her fingernails down his back, his skin responding to the her touch, he was relaxing into her now. Her left hand was playing with herself, her right hand was jerking Robert off, she had the motions synced. Both of his hands were working on her breasts, pushing them together, tweaking her nipples. He could have explored her body all night.

"You got protection right?" She asked breathlessly.

"Yes." He replied his mouth was as dry as a desert.

He moved away from her quickly and rummaged for his pants which lay strewn near her closet, he grabbed his wallet and pulled out the foil wrapper.

"Put it on and let's do this. I have to be up early to study and I need you to make me relax." Ruby threw her head back in a hearty laugh and moved up in the bed, resting her face on the pillow and drinking in every detail or Robert's body as he pulled on the condom.

"Don't worry I will show you how I like it done."

Ruby grabbed his shaft and rubbed it against her pussy, Robert could see that it was darker around her opening due to the wetness of her slice. His helmet felt warm as it slid in side of her, he braced his arms on either side of her and slowly rocked in and out of her, her nails still trailed up and down his back. Her eyes were closed and her head was tilted away from him, he leaned down and began to kiss her neck softly. She groaned and writhed into him, he took deep breaths and focused on the task in hand. Robert couldn't believe that he was having sex with the girl of his dreams. He pushed into her harder now, her muscles had relaxed around his shaft, the extra motion made her tits jiggle, he was intoxicated and hypnotized by her.

Her hands reached down and grabbed an ass cheek each, she pulled him deeper into her. She was breathing heavily now, she always could rely on a fuck to clear her head. She hadn't intended of ever taking Robert to bed but she had a sex dream about him two nights prior and just couldn't shake it. She had always known that he was into her but she didn't want to risk losing their friendship, he was one of the good guys on campus who was interested in more than getting into her trousers. She knew that she was pretty enough to go to the student bar and not pay for a drink all night, pick which guy she wanted to lie with and move on the next morning. Ruby was getting bored of that now, she had received her first B and knew that she had to settle down and focus more. She came from nothing and worked extra hard just to get into the college, she wasn't going to throw that away.

"Are you OK?" Robert whispered timidly into her ear.

"Yes, don't stop now, keep doing me like you are.

Robert was relaxed now, her hands on his ass was helping his motion and momentum greatly. Her eyes remained closed, he was afraid she was imagining him to be another guy but he found that he didn't mind if that was the case. Just to see her naked was his fantasy, the fact that he was now inside of her was his wildest dream come true.

After a few minutes he grabbed her leg and pulled it across his body, he then lay on the bed beside her in the spoon position. He grabbed his prick and guided it back inside her warmth, her breath had become shallow, he could see her eyes rolling into the back of her head underneath her eye lids. Ruby was biting her lip while slowly caressing her breasts.

"That's really good Robbie, you are not like the other guys." She whispered.

Robert was glad that her eyes were still closed so she couldn't see the hue or crimson that his face flashed. On one hand his head was spinning but another doubt crept in, he stupidly hadn't considered competing with her previous conquests. He blanked out the thoughts and just focused on the beautiful woman he was inside, he slid in and out of her now in a steady pace, he snaked his hand around and began to massage her pussy, all the while kissing her neck. Her groans intensified. Her dampness was making it easier for him to slip in and out of her, giving him more confidence.

Ruby placed a hand on his and moved the fingers on her twat the way she liked it, he didn't miss a beat and quickly fell into the steady rhythm. Her other hand was placed on his hip, rubbing up and down his thigh. he could have stayed in this bed forever, he felt the shackles of his sheltered youth falling off, the dust he accumulated pouring over books and taking notes blew away in the breeze. He finally knew now what it meant to be living. She moved off of him and pushed his shoulders back onto the bed, she swung one leg over his hips and straddled him, Ruby spat on her hand and rubbed it on her gash before grabbing Roberts shaft and putting it back inside of her.

Looking up at her tits as they swung with the movement of her bouncing on his cock drove Robert crazy, when she landed down on him her ass cheeks were crushing his balls in the best possible way, he had totally eased into the act now, the smell of her body and the touch of her skin on his felt brilliant, he hadn't realized how much he wanted her until now. She eased up on the bouncing and started to grind herself on him, his cock probing deeper into her than before, he knew he wouldn't last long in this position. He trailed his hands up her hips to her breasts and cupped them both, rubbing both of her nipples gently as his body jerked and he let out a grunt. Ruby continued to grind on him for a few seconds before rising off him, his semi hard cock along with the full condom smacked against his stomach as he flopped out of her.