Eleanor paced around the massive library, trying to figure out who she could ask to escort her to the charity event the next evening. She just could not show up alone. That would be appalling. Damn Jonathan, he should have been more careful. I told him that it was dangerous to ride a motorcycle, but did he listen to me? No, he just had to try it and look where he landed. In the hospital, because he tried to round a corner and lost his balance causing the damn thing to fall on him. I hope that his leg itches like hell inside that cast.
As if her mind had conjured up a motorcycle, she heard the distinct roar as her tenant Jordan McAllister roared up the driveway and back to the small house, he rented from her. She knew she should be mad at Jordan because he was indirectly the cause of Jonathan wanting to ride a motorcycle. He thought it would be cool, but he never took into consideration that he was forty-five years old and older bones broke faster than one as young as Jordan.
Suddenly it hit her. She would ask Jordan to escort her to the charity event. After all, if Jonathan had not seen his motorcycle, he would not have tried to ride one Eleanor reasoned. She knew it did not make sense, but it was a good enough reason to ask Jordan to do it.
“Emily, I am going to take a walk. I will be back for afternoon tea shortly,” she called out to the housekeeper.
Emily popped out of the kitchen and was halfway up the hallway when Eleanor was heading to the front door. “Yes mam, just let me know when you want tea served,”
Eleanor slowly made her way over the well-manicured lawns to the small house at the back of the property. Jordan was a college student just getting ready to start medical school. Each year she rented out the two small properties to college students at a very reasonable price. Her late husband had been on the school board and a professor there so this was a way they had gave back to the community. Walking up to the door, Eleanor took a deep breath before raising her fist and knocking on the screen door.
She could hear country music playing in the background and then the sound of shuffling across the floor. A few seconds later, Jordan appeared in front of the door, barefoot, clad in jeans that rode low on his hips and hugged his legs and ass, and shirtless. Eleanor knew it was impolite to stare but she could not help it.
“Good afternoon Eleanor. Please come in,” he said as he unlatched the screen door and pushed it open, standing to the side to allow her to pass him. “Can I get you a cup of coffee or a glass of iced tea?” as he led her into the living room.
“No thanks,” she said taking the wingback chair he offered her. “I want to ask you something…actually a favor,”
“Can you give me a couple of minutes? I just got in from school and want to grab something to drink. I also want to grab a shirt. I was getting ready to get a shower,”
“Sure, take your time,”
Eleanor watched him walk out of the room, her eyes glued to his tight ass, wondering what it would feel like to grab it. She could feel her face redden at her erotic thoughts and silently chastised herself for having them. Eleanor and her late husband had led a very active sex life and she missed it but that was no reason for her to lust after a man young enough to be her son.
She was drawn out of her thoughts when he can back into the room, this time wearing a tight-fitting tee-shirt and carrying two glasses of iced tea, handing one to Eleanor.
“I know you said you didn’t want anything to drink but I hate to drink alone,” he told her chuckling before settling down in the corner of the couch. “Now what type of favor do you need?”
Eleanor took a sip of the iced tea before she asked, “I need an escort to the charity event my company is putting on tomorrow night. Jonathan usually accompanies me but unfortunately, he is laid up with a broken leg.”
Jordan took a drink of his iced tea, his eyes locked with hers as he gave her request some serious thought. “I am sorry, but I don’t have a tux. That is not something that is part of a medical student’s wardrobe.”
“You don’t have to worry about that. I will rent you one,” she assured him. “I will make it worth your time. How does ten thousand dollars sound?”
Shocked that Eleanor offered him the money, Jordan almost dropped his glass. He knew that she was very rich, and that amount of money was just a drop in the bucket for her. Jordan thought for a long moment, wondering what else she would be willing to do to get him to agree.
“Okay, but there is one other condition. You have to have sex with me,” he teased her, not sure what he expected her to say or do.
Without any hesitation, Eleanor quickly said, “Agreed. I will set up an appointment for you at nine in the morning with Evening Wear to get your tux. We will leave about six o’clock,”
“I only have a motorcycle so will you be able to ride it wearing your evening dress?” he asked as serious as he could. At the appalled look on her face, it was all he could do not to laugh at her. “I am just teasing but it is the only mode of transportation I have so you will have to provide that,”
“I have that covered. Thank you,” Eleanor told him, putting her empty glass on the coaster on the table between the two wing chairs and standing to leave.
Jordan set his glass down and stood up also, following her to the door. At the door, Eleanor suddenly turned around, reached up, and put her arms around his neck, pulling his head down toward hers. When he was close enough, she captured his lips with hers, kissing him deeply, her tongue demanding entrance. At first, he was a bit shocked at her boldness but then his arms encircled her waist, drawing her tighter against his body, letting her feel just what the kiss was doing to him.
Eleanor broke the kiss, patted his cheek, and said, “Don’t forget, you need to be at the Evening Wear at nine o’clock tomorrow to get your tux. See you later that evening,” as she waltzed out the door, leaving him with a semi-erection and wanting more.
After shutting the door behind her, Jordan went upstairs and took a cool shower before grabbing himself something to eat and then settling down to study.
That evening Jordan decided to walk up to the main house, so she did not have to have the car come down and pick him up. Ringing the bell, he was greeted by her butler James.
“Good evening Jordan. Please come in. Madam is not quite ready,” as he opened the door wider, motioning for Jordan to come inside.
Stepping into the foyer, he waited until James had shut the door and then followed him down the hallway to the library. Jordan had never been further than the foyer when he dropped off his rent check each month, so he made sure to look around and take in all the details. He knew that Eleanor was rich, but he had no idea she was that rich.
“Would you like something to drink?” James asked.
“Ah no thank you,” as he took in the impressive library filled with what he figured were some first editions and rare books.
James nodded and left the room. While he waited for Eleanor, Jordan walked around the room, looking at the various art pieces and books on the shelves.
“Sorry I am running a bit late,” a soft feminine voice said behind him.
When Jordan turned around and saw Eleanor, it took his breath away. She was wearing an off-the-shoulder evening gown of deep burgundy, her dark brown hair hanging loose on her shoulders. As she made her way into the room, Jordan admired her legs from the high slit in the right side.
Damn, she is one foxy lady. Not sure how old she is but does not look a day over forty. Wish I was going to have her in my bed tonight.
“You look beautiful,” Jordan told her. “All the women are going to be so jealous of you tonight,”
Eleanor blushed and said, “Shall we go? It would not do for the hostess of the charity event to be late.”
Jordan offered her his arm and they headed outside. When he saw that they were traveling in a limousine he was shocked. He figured that she would use a town car and not the limousine. Before he had a chance to open the door, the driver was there opening it for them. Jordan helped her in and then got in. When they pulled up to where the event was being held, there was even a red carpet for them to walk down to get into the building. After a nice meal and an evening of dancing, it was time to head home.
“Just have the driver let me out at your home and I can walk back to my house. It is not far,” Jordan said as they pulled into the driveway.
“Nonsense,” Eleanor said. “He can drop us off at your home. I don’t fancy walking any distance in these heels.”
“Both of us?” he asked in a quizzical tone of voice.
“Yeah, you said part of the deal was to have sex afterward,” she told him.
Jordan laughed and said, “I was only teasing you about the sex part. I enjoyed myself tonight, got to ride in a limo, and had the prettiest woman on my arm.”
“So, I don’t turn you on? You have trained your cock to pretend to be hard?” Eleanor asked with a little pout.
“What makes you think that?”
“Well, you say you don’t want me but when we kissed at the door your body told a different story unless it was a fluke, or you have trained it to react in certain situations.”
Before Jordan had a chance to answer, the limo stopped in front of her home, and soon after, the door was opened by the driver. Jordan stepped out and offered his hand to Eleanor to help her out.
“Will there be anything else madam?” the driver asked.
“No, that is all,” Jordan quickly said, not giving Eleanor a chance to answer.
Once the limo pulled away, they stood there for a few moments before he leaned down to kiss her cheek. Eleanor saw where he intended to land the kiss, so she quickly turned her head, so his kiss landed on her lips. Jordan knew that he should pull away, that she was his landlord, and if they slept together and things went south, she might make him move out. On the other hand, they could end up being landlord-renter with benefits.
Breaking the kiss, Jordan looked down at her in the moonlight, his inner devil-angel arguing with themselves. Finally, he asked, “Are you sure and not because I told you that was part of the bargain either.”
Eleanor reached out and cupped him through his tux, saying, “Been awhile and I miss sex. Do you want to come up to my suite?”
Jordan shook his head and said, “My place,”
“I need to change out of this gown and heels. I will meet you there in fifteen minutes,”
“I will wait out by the pool,” he told her. “In fact, let’s go skinny dipping,”
Without saying a word, she took his hand and led him around the mansion to the back where the pool was. Going into the pool house, Eleanor switched on the lights in the pool, illuminating the water.
“Jordan,” she called out, “can you come in here and unzip me?”
Jordan stepped into the pool house and unzipped her dress. Eleanor let it slide down her body, revealing that she had worn nothing underneath. Jordan was a bit shocked as he stared at her. He never thought she would be that bold to go commando. Picking up her dress, she laid it on the table inside the pool house and kicked off her shoes. Jordan quickly undressed, leaving his tux with her evening dress.
When he walked out of the pool house, Eleanor was already in the pool doing laps. He went to the deep end and dove in, splashing her. Before she had time to retaliate, Jordan grabbed her around the waist, pulling her close, his free hand grabbing a hand full of hair, pulling her head back to expose her neck. He leaned down and began to kiss and lick the exposed area, slowly making her way down to her breasts.
The combination of the night air and the coolness of the water made her nipples pebble. Jordan kissed his way downwards, finally latching onto one, giving it a lick, and then sucking hard. After lavishing attention on one, he moved to the other one to do the same thing. As he alternated between her nipples, Jordan was slowly moving her back to the side of the pool.
Her hand moved between them, grasping his cock, stroking it. Jordan lightly nipped her nipple while pinching the other one. Grabbing her by the waist, he lifted her, saying, “Wrap your legs around my waist,”
Once she did, Jordan began to rub his cock against her pussy while his lips claimed hers hard, their tongues mating frantically. Taking her to just the edge, Jordan broke away and swam to the other side of the pool. Eleanor bobbed in the water, her breathing labored.
“Damn you,” she told Jordan. “I was on the edge,”
Jordan chuckled and told her, “I wanted to slide myself in you and fuck you hard and deep, but I don’t have any condoms,”
“We don’t need them,” she said swimming over to him. “I am way past the age of getting pregnant and I have not been with another man since my husband died several years ago. Are you clean?”
With him working and going to school, Jordan had had no time to play so he knew he was safe, so he grabbed Eleanor and pulled her toward him. She once again wrapped her legs around his waist, this time sinking down on his throbbing erection. As he slid inside, Eleanor let out a contented sigh, gripping him tight. Jordan grabbed her ass, pushing in as deep as he could. Pushing her against the side of the pool, he started to gradually move in and out.
As he slowly fucked her, they began to share kisses, their tongues doing their own mating dance. Once again taking her to the edge, Jordan began to make his way to the steps at the shallow end of the pool. Holding her tight, he made his way up the stairs over to the first chaise lounge. He pulled out and set her on her feet.
“Down,” he ordered.
When she laid down, he took hold of her ankles, pulling her to the edge of the chaise lounge, spreading her legs, and dropping between them. He put both of her legs on his shoulders, and buried his face in her pussy, sucking hard on her clit. As he sucked her clit, Jordan started to finger fuck her hard and deep. He curled his two fingers and sought out her G-spot. When he hit it the first time, Eleanor almost came off the chair, the pleasure so intense.
Even though she and her late husband Darwin had a happy fulfilling sexual life, he had never found that spot. The pleasure so was intense her eyes almost rolled back in her head as her orgasm rolled over her like a runaway freight train. She let out a scream, her legs clamping tight around his head, almost drowning him with the amount of juices that squirted and flowed from her.
When she was finally about to relax her legs, Jordan stood up and flipped her over, positioning her on her knees as he got behind her. Before she had time to recover from her orgasm, Jordan buried himself deep inside of her. Gripping her hips tightly, he started to pound her with hard deep thrusts. Reaching under her, he found her swollen clit, pressing on it with his thumb, moving it in circles.
Eleanor could feel another orgasm building up inside of her. Jordan rubbed her faster until her entire body started to shake, her insides heating up until Jordan let out a roar, filling her with his cum. Holding her tight against him, he soon felt her trembling with another orgasm. When it was over, he pulled out and sat down on the pool deck, his cock still leaking. Very slowly Eleanor turned over and sprawled out on the chair.
“Wow!” was all she managed to get out. “That was explosive,”
“You think that was explosive just wait. I am not done with you yet,” he told her. “You have holes I have not even tapped yet and the night is young,” as he got up and dived into the pool to cool off.
Eleanor watched him swimming a few laps, anxiously anticipating what he would do next.