Real estate tycoon David Aaron had a son who had fallen on hard times. When Jesse's mother passed away unexpectedly, the boy had taken it hard. He and David's late wife had always been close. Growing up, Gloria Aaron had always been there for her son while David was busy earning the fortune that would sustain them later in life. David did not neglect his children and made sure that they had everything they would need - save for enough of his too-precious time. His older children emerged with few battle scars, but the same could not be said for Jesse. His mother had to be there to pick up the pieces and when she passed away a few days after Jesse's 17th birthday, he was devastated. David and his older children did the best that they could for Jesse, but he fell through the cracks. The once-thriving, promising young student fell in with a bad crowd. By the time the formerly-healthy young man turned 21, he was a full-fledged drug addict with a horrific addiction to heroin. As the scion of a wealthy family, the drug was easy to obtain - too easy. Jesse's siblings did as much as they could and David came home and abandoned his pursuits of wealth for a time. He knew the value of money, although he valued family far, far more. He had already lost the love of his life before she had even reached the age of 40. He was not going to allow his youngest child to be swept away on the wings of addiction.
He took a leave of absence, with the Board of Directors threatening to replace him. David took a firm stance and countered their threat. Should they dare to make such a move, he would pull all of his funding from several large projects. This threat was tantamount to his saying those projects would never reach fruition and he knew he had them in his cross hairs. They backed off and allowed him to institute proxies in his stead until such time as he could return to the businesses he ran so competently.
David got his son into a treatment facility, a very good one. He got daily therapy and Jesse began to respond. It helped enormously for him to have his father in his corner, with the added support of his siblings, their spouses and his nieces and nephews. While it time for heroin's grip of Jesse to loosen, all could see that he was turning things around. The only fear was that once Jesse found himself with too much time on his hands, he would slip back into the deadly pattern of addiction. Jesse's therapist suggested to his family that they find him something to do, some kind of purpose to his life. Unlike his older brother, the strict regimen of military life would not work for Jesse. He did need structure, but a structure of his own making and not one that he would rebel at. Military life for the young man would chafe and he would need something of his own. An accomplishment that would enable the young man in recovery to prove he yet had something to offer the world.
A bit of serendipity happened to fall in Jesse's lap due to one of his father's older business deals. A grouping of apartment / brownstones lost their superintendent. Her family had fallen on difficult times back in North Carolina and Eugenia had to return to them. Most of the other tenants were too new or too young for David to consider offering them the job of taking care of the buildings. However, it would prove to be a golden opportunity for Jesse. He would have a job that wasn't complicated, it would afford him some spare time in which he could return to school at nights and also, an apartment of his own to live in, albeit one in which his family could check in on him from afar. All that remained was for the family to convince Jesse to accept the opportunity placed in front of him.
It actually took very little convincing on their part. Before he had fallen prey to the lure of drugs and addiction, Jesse had been a highly-motivated young man. He had always wanted to make his mother proud of him, his father too, to a lesser extent. He saw this as an opportunity to rebuild and eagerly accepted the second chance he was afforded.
The first thing that Jesse did to ensure that he stayed clean was eliminate any and all of the old friends that had led him down that path. In his meetings, many of the others spoke of relapses. Jesse was determined that he himself would not have such a story. He wanted to ground himself in the real world. If a problem came up, he would address it in the right way and not by turning to drugs.
He spoke with his father and let David know that he didn't want any of his money. Jesse had a sizable trust fund that had been left to him by his mother. Jesse told David to invest the money and to appoint a trustee. He would work and earn his own salary by taking care of the building. He and his father agreed upon a reasonable salary for his efforts. It would be one that would allow him to maintain a nice living, but not the hedonistic, free-wheeling, drug-addled life he had led before.
He also knew that he would need to keep busy. By taking care of the building, he'd be able to do just that. So began the young man's road to redemption.
It did not take David Aaron a long time to see that he would soon have something to be very proud of in his newly-focused youngest son. Jesse devoted himself to the building and to the 30-odd tenants that occupied it. If he did reach out to his father, it was rarely for money. It was usually a request for assistance with something he was not qualified to handle himself, like plumbing or electrical work.
Chicago winters can be very brutal, so Jesse made sure that he was out there after each and every snowfall, making sure the walks were clear and that the parking lot was plowed promptly by the contractor he had hired to do so. If the contractor ran late, Jesse started shoveling the walks by himself. Several of the tenants were seniors and he didn't want any of them having accidents. Once David heard of this, he made sure that his son had a snow blower to make things easier on himself.
When spring rolled around, Jesse began puttering around the property. They had someone to cut the grass and do the major landscaping, but the young man liked working in the flower beds. David saw that his youngest son had inherited the Green Thumb possessed by his late mother. He was so proud of his son and how well he was doing. He praised the lad to his siblings and increased Jesse's salary, although not overtly. As it was still early in his son's recovery, he placed another few hundred in trust for Jesse every month. He had every confidence in the young man that he was on the true path to recovery, but he did have enough common sense not to dangle the temptation of extra money in front of Jesse's nose as this stage of the game.
Jesse was too focused on his responsibilities to think about his past addictive behavior. The closest he came to any form of relapse was an occasional beer and alcohol had never been his drug of choice. He'd always been able to have one or two beers and stop there. That pattern had not changed. Jesse believed that he had conquered his demons and they had not conquered him.
He was well liked by the tenants, the old and younger ones alike. A few of the seniors liked him and treated him almost as a grandson. If Jesse didn't feel like cooking a meal, he usually had at least 5 standing invitations to dinner. Many of the young married couples offered him meals as well. There were also a few young and attractive female tenants living in the complex. Some weren't exactly subtle in their hints to the young, strong, dark-haired superintendent that dinner might not be the only thing on the menu. Jesse didn't mind flirting with the single lady tenants, that was fun. He was sensible enough not to allow himself to indulge in any hanky-panky. It was far too early for him to consider a relationship; he needed more time to gain control of his own life. It wasn't the easiest decision for Jesse to make. Some of the young women were quite attractive, overly flirtatious and Jesse had been without female companionship for over a year.
One of his neighbors continued to insist on trying to fix him up with her granddaughter. "Val would love you to bits and she's such a sweet girl," Mrs. Norris continued to insist. "She's bright, articulate and funny and a wonderful cook - why won't you let me set it up between you two?"
Mrs. Norris was Jesse's favorite tenant. She was almost 80, but looked years younger. She and her family ran both a restaurant and a bakery and she still worked several days a week. She was always kind and thoughtful; she usually brought him a pastry of some sort every day. Had Jesse not worked so tirelessly, he might well have weighed 300 pounds. He was constantly running errands for the kind widow, feeding her cats when she was working and making sure her flower beds were watered. In fact, Mrs. Norris felt a great deal to Jesse like she was a part of his family. If he didn't see her for a day or two, he felt as if something was missing.
So when he didn't see her for a few days, he went looking. Mrs. Winston, one of the younger wives in the complex, had sad news for him. "She took a fall in the restaurant a couple of days ago," Leslie told the handsome super. "She'll be in the hospital for about a week, they just want to check to ensure that there is no neurological damage." Leslie was a nurse in the same hospital, so he relied on the nice, good natured blonde for updates on his favorite tenant. He realized that no one was feeding Pookie, Mrs. Norris' cat. A cat could go a few days without being fed, but it had been nearly 3 since his friend had been in the hospital. He took it upon himself to feed Pookie, change the litter box and to water the plants. Jesse knew that Mrs. Norris would not mind the intrusion as he had been in her apartment on several occasions. It was usually to make some small repairs and to share a cup of tea and a Danish or two - or three.
The last time Jesse went to check on Mrs. Norris' apartment, he got quite the surprise. He heard someone rumbling around in there and he knew that Mrs. Norris had no close friends who lived nearby or relatives. She had a few things that were worth some money, so Jesse prepared to find a burglar raiding the old lady's apartment. Steeling himself and holding a baseball bat, he entered the apartment and there was the surprise - albeit a rather pleasant one from all appearances.
Inside the apartment, holding a can of cat food, Jesse came upon a very attractive brunette. It was easy to see just how attractive she happened to be, because her skirt was short and her heels were very high. She had one of the most beautiful faces that Jesse had ever seen and the rest of her was equally lovely. The only problem was that Jesse still had no clue as to who she was. He knew only that she likely wasn't a burglar, because what kind of burglar takes the time to feed the cat? He made a coughing sound so that the young woman would see him standing there in the doorway. The young woman shrieked and dropped the can of cat food. That was no problem for Pookie, who promptly began cleaning up the spill.
"Who - who are you?" The young woman said nervously. "How did you get in here?"
"Shouldn't I be asking you those questions?" Jesse answered. "I'm the super of the building, I have a key and I came to water the plants and to feed Pookie while Mrs. Norris is recovering in the hospital."
Hearing those words seemed to calm the young woman down tremendously. "Oh, thank God," she said to Jesse as she picked up the can from the floor. "My Gran has some expensive stuff, I thought you might be a burglar. Hey, if you're the super, you must be that guy who has been so nice to Gran - the one she keeps trying to fix me up with. Wow, I should start listening to her advice," the girl said as she scanned Jesse quickly and smiled. "A nice guy and he's good looking, way to go, Gran!"
Now Jesse could ID the girl as well - she had to be Val, Mrs. Norris' granddaughter. He knew that the older women only had grandsons. He also found himself agreeing with the younger woman about listening to Mrs. Norris, as Val was quite the looker. A brunette with sensual almond eyes, terrific face, great legs - oh yeah, he would pay a lot of attention to Mrs. N the next time she wanted to set him up.
"I didn't think you lived close," Jesse recalled as he started helping her to clean up the mess and got water for the plants. He remembered that as being one of the "reasons" he had told Mrs. Norris that it likely wouldn't work out between the two of them.
"I don't live close. I live in North Carolina," Val smiled and lit up the room. "However, I don't have the kind of job where I have to account for myself, so the instant I heard Gran needed me, I hopped in a car and headed to Chicago."
Jesse was already impressed by the girl's beauty and now, he was equally impressed by her care for her grandmother. Someone this good-natured and beautiful was not someone he dared to let get away. He had to act - fast! "When did you arrive?" He approached the young brunette.
"Only about 30 minutes before you showed up," she answered with her million-gigawatt smile. "I haven't even unpacked my things, poor Pookie looked like she was starving."
Jesse smiled as he eyed the cat. "She always acts like she's starving," he laughed. "I fed her early this morning and she's scarfed it all down. So, would I be correct in assuming you haven't had dinner yet?"
"No, no, not yet," Val answered him with a slight smile. "Are you asking me to dinner?" Jesse nodded and her playful smile widened. "My, aren't you forward, asking out a girl you hardly know."
Jesse was about to answer with something flippant, but Val didn't give him the opportunity. "That's okay handsome, this girl likes a forward man. She also likes to eat - I'm a foodie. Is there a good steak house around here?"
With her slim figure, Jesse found it hard to believe that she could pack it away. He would soon learn otherwise. "This is Chicago, we like to eat," Jesse told Val. "There are several."
"You pick one, but let me treat," Val insisted. "It will be my way of saying thank you for being so nice to Gran."
"Okay, let me check a few more things and I'll go home to shower and change," he said with a broad smile. One thing the modern-thinking young man had learned was not to go all macho when a lady offered to treat. He wouldn't object to a free meal and the odds of his getting a second date with Val increased a great deal if he didn't act like a horse's ass on the first one. The agreed on a time and Jesse rushed through his few chores so that he could shower, change and be back at the agreed-upon time. His dad had always valued punctuality and taught it to all of his children. Jesse hoped that Val would appreciate that quality in him. He also hoped she wouldn't mind his wearing a suit to dinner. As a larger man with a broad chest, he had always known a suit looked good on him. He wanted to put his best foot forward, which reminded him that his dress shoes needed a good shining. He set about polishing his shoes and hoped that he wouldn't come across as stuffy and old fashioned when he went to meet Val for dinner.
He needn't have worried. A few minutes before the arranged time, he arrived to pick up Val for their dinner date. In the pretty, short red dress, she had been sexy. In the dress she wore now, she had kicked it up a notch to "knockout". It was a shiny black cocktail dress and she had added black stiletto heels. Although she gave the illusion of being petite, Jesse had noticed when they were talking earlier that she came up just past his chest in her previous pair of heels. With the 5-inch stilettos, she could almost look him in the eye, making her around 5'8" or so. She had just said something to him, so he cleared the cobwebs from his head and tried to listen.
"Hello? Earth to handsome guy? I said that you're staring at me," Val smiled as she grabbed her purse.
"I'm sure you get that a lot," he replied to the stunning, leggy brunette. "You are one of the most beautiful women I have ever seen and I'm not just saying that to butter you up. Wow, that's how you look in that dress - just, well, you know, WOW!"
Val smiled and it just made Jesse feel like he had won the lottery. "Thank you," she told him as she linked her arm through his. "I wish my last boyfriend had been so complimentary and considerate. I'd go to the trouble of dressing up for dinner and - special occasions - and he barely noticed," she sighed. "A girl likes to know her efforts are appreciated."
"I don't know anything about your last boyfriend, although there is substantial evidence that he's an idiot," Jesse grinned as he opened the car door for the leggy brunette. She gave him a lovely display of those legs as she slid into the passenger seat. "If a girl goes to any sort of trouble, her date should say something complimentary. I wasn't sure that I should wear a suit, now I'm glad that I did."
"You shined your shoes, too," Val commented. "Some women don't notice those kinds of details, but I do."
Jesse was so happy that he almost felt as if he was floating on a cloud. On the way to the restaurant, he learned that Val - short for Valentina - was both a photographer and a portrait artist, quite successful in her field. She was a lively and animated conversationalist and wonderful company. As they neared the restaurant, Jesse found himself wishing he had taken Mrs. Norris up on her offer long ago. Every second he spent in Valentina's company was making him feel like the luckiest guy in all of Chicago.
Through the entirety of their meal, Valentina proved two things - she was a wonderful dinner companion and she had not exaggerated about her appetite! The girl could eat and they polished off an entire bottle of wine and a few drinks after as well. Even dessert was not refused and it was almost midnight when they left the restaurant. They decided that they should call a taxi as neither was sober enough to drive the short distance back to the brownstone. Jesse was most certainly not going to complain about sharing the back seat with the attractive, seductive young brunette.
Standing in the middle of her grandmother's residence, Valentina did what she had wanted to do all evening and since first meeting the handsome Jesse - she gave him a breath-taking kiss. "I really, really am attracted to you," she said after breaking their embrace. "It's just - well, it would be a bit weird if I did anything here in Gran's place."
"I completely understand," Jesse said with a smile as big as the sky. "Aren't we lucky that my place is only a few doors down from here?"
"Why Mister Jesse Aaron, are you trying to get me to your apartment so that we can do all sorts of naughty things?" Valentina said, her dark eyes shining playfully.
Sure that the sultry brunette was teasing him, Jesse smiled playfully as well. "I certainly am and if you have any extra ideas, I'd love to hear them," he said to Val.
"Just let me feed the cat," Valentina grinned as she walked towards the refrigerator. "I may not make it back here before the morning and we wouldn't want her to starve." Jesse had never before been this anxious to go back to his apartment. There was something about the leggy beauty that suggested this would not be an evening he would forget any time soon.
"I hope you can keep up with me," Val purred in his ear as they exited the apartment and went to Jesse's place. "I'm a very wild fuck!"
"I promise to give you my best work," Jesse kept up with the banter.
"Oh baby, you won't have to work," Val countered. "It's going to be all pleasure!"
Jesse didn't doubt that, not for an instant. As a matter of fact, he got proof of that the moment they entered his residence. Valentina did a brief little shimmy and her sexy black dress dropped to the floor. Now she was wearing slinky black lingerie, stockings and those amazing stiletto heels. She walked quickly to her attentive lover and kissed him with such passion that it made her previous kiss seem chaste.
"A wild fuck, remember?" Valentina purred as she searched for the bedroom. Finding it, she walked away from him and cocked her head to one side. "You might want to set your coffee maker to brew us a pot for later on - we're going to need it."
Jesse didn't doubt that for an instant. He was certain that every moment he spent with Val was going to be the very definition of the word "ecstasy" and yet, he knew he would have a lot of work ahead of him, despite her assurances. You did not become so fortunate to bed someone like Valentina and then, just go through the motions. You considered each and every action and you paid careful attention. She would be the type of person to give clues as to what she liked.
Valentina stretched out on the bed and proudly displayed a body that she obviously worked hard to maintain. There wasn't a blemish on her skin and her face was beauty without a single flaw. She sat up as Jesse approached the bed and offered her lips for a kiss. Jesse took her face in his hands and gave her the best kiss he was possible of bestowing. It seemed to entice her further as her agile tongue joined with his and the pair fell back on the comfortable bed. Her arms went around his back and they tumbled together, still kissing as if their lives depended on it.
Jesse had never felt such an instant connection with anyone before. Valentina likely felt the same way, as she was offering something many men would have given weeks or months of their life to obtain. There was a chemistry between them that they both felt. Jesse knew that with someone as unique as Valentina, you didn't rush anything. You took your time so that you could appreciate the entire portrait and not just the scenery.
To that end, Jesse didn't just make moves to get Val naked so that they could have sex. He went over her body with deliberate, slow moves. He looked at her in the pretty lingerie and the heels she had worn for the effect. He removed them slowly and gave her a foot rub, which evidently pleased her from the sensual little moans she made. He took in the full scope of her beauty as he kissed her with precise little kisses that were intended to evoke her passions - and did so. Her manicured nails dug into his back as their embrace grew more torrid and their passions more heated.
"You - are incredible," Val gasped as the two lovers released each other for a brief moment. "Don't stop what you are doing!"
Jesse allowed himself a small-but-satisfied smirk. "I wasn't planning on stopping," he said as he positioned his brunette flame stretched out before him. He planned to treat her as a sexual buffet and act as a starving man. His lips touched her body everywhere as pieces of her dainty underwear were removed. Valentina offered no signs of protest, instead, her little cues indicated that she liked everything Jesse was doing to her. His mouth alit on several spots and it seemed to him that from her wet pussy to her stiff, peg-like nipples, every inch of Valentina was sexually charged.
He didn't stop, he continued with his manipulation of Val's sensual body. Her pussy was wet and sweet and tight, his fingering of her confirmed just how snug she was down there. His fingers moved in and out and her groans became louder and more guttural. Valentina was certainly proving to be the wild woman she had claimed to be.
"You great, big, wonderful fucker!" Valentina exclaimed as she sat up. "Okay baby, it's this girl's chance to show you what I can do. Let me help you off with your remaining clothes and then, let me at your cock!" She fumbled with Jesse's few items of clothing and let out a gasp. "Holy fuck!" Valentina said to him. "Is all that really you?"
Jesse had been told on previous occasions that he was hung, although he himself had no basis for comparison. He simply nodded and let Valentina fondle him for a few minutes so that she could judge just how she intended to handle his 9 inches of manhood. Once she made up her mind that she could deal with it, the leggy brunette got down to business. Valentina was a sexual diva who could easily bend a man to her will, but she didn't act that way with Jesse. Theirs was to be a relationship of give and take, so she accepted his thick cock in her mouth as she set about giving him the BJ of a lifetime. She even decided that she would swallow his spunk, something she rarely did. If he kept up the performance, the naughty brunette even toyed with the idea of letting him go in the back door.
Jesse thrilled to the terrific blowjob he was receiving from Val. She was practically worshiping his cock, her tongue trailed all over it from the base to the crown. When he felt himself about to cum, he tried to pull away. With fierce determination, his sexy lover took him balls deep and when the load exploded, she was there to capture it all. He looked into her dark brown eyes with admiration, as none of his previous girlfriends had been able to accomplish that.
The two lovers languished for a little while, although not as long as Val would have expected. It didn't take Jesse long to regain his stamina. He didn't even get a chance to ask for Valentina's opinion. She merely said "Pick a position and just make sure that you really give it to me - like a slut!" Jesse had already surmised that the slender brunette wasn't made from china, so he got in behind her as she got on all fours. He just eased in at first, but Val had made it clear she didn't want to be treated like some fragile little novice. Her guy had gotten the picture and it only took a few minutes before the virile Jesse was fucking Valentina in the proper spirit, with all of his lust behind him.
"Oh yeah, that's it baby, fuck me, fuck the pussy, fuck the hell out of my pussy!" Val screeched as Jesse pounded her from behind. While he was deep inside of her, his hands were not idle. He was fondling her tits and slapping her ass, he had picked up on the clues that she loved it a bit on the rough side. He even tugged on her long, dark hair as he fucked her. Valentina took note of that and promised herself that this would not be the only time she fucked the handsome stallion, because he was simply too good for a one-night stand. This energetic man was the kind of lover that a smart, sexually-charged lady kept around for as long as he wanted to keep coming back.
His savage fucking set off something in Val and she countered it with precise movements of her very own. Her body slammed back against his and Jesse felt up to the challenge as his cock surged deeper inside of her slim, yet surprisingly strong, young frame.
The two of them rutted like beasts for another 40 minutes before coming almost at the same time. Jesse got up to make them some coffee while Valentina sat in bed and plotted out their next adventure. She felt confident that Jesse was good for more than one maniacal fuck in the space of an evening.
When Mrs. Norris got home from the hospital, she was quite pleased to discover that Pookie was fine and well looked after. All of her plants appeared to be none the worse for wear as well. She was even happier to discover her granddaughter had not yet gone back to South Carolina. Val informed her Gran that she was considering a change, perhaps moving closer to Chicago and her closest relative. If Mrs. Norris had caught the brief smile that passed between her handsome young super and Valentina, she said nary a word to either of them.
Mar 26, 2018 in romance