Rebeccas Arrangement

"The two most used alibis I know are, 'I have a date', or 'I joined a book club'. Families tend to accept those. However, if pushed, you must not leave any impression that Mr. Denton is involved.

When you shop for cloths, don't neglect nice lingerie. Here this will help get you started." Rosa said as she slid a gift card across the table.

"$500 gift card!" Becky exclaimed.

"Sam told me you are in a financial situation, this is for cloths makeup etc. just to help you out.

Any other concerns?" Rosa asked.

"No, just nerves."

"Relax Rebecca, everything will be fine. I assure you, the dates will be very enjoyable."

The rest of the lunch and drive back to the office was spent chatting and laughing. Becky was still not used to being called Rebecca after all these years. She thanked Rosa for her time and helping out, then returned to her daily routine.

Rosa called Sam when she was back in the privacy of her office.

"Everything is all set for Friday evening. I would recommend not starting at the top but a mid level restaurant. Step up slowly as Rebecca gets more comfortable." Rosa advised her boss.

"No red flags."

"Just nerves, nothing too concerning."

"You're the best Rosa!"

******* Friday Evening *******

Becky used the book club excuse with Vicky, who never gave it a second thought. Now standing in her front of the full length mirror in her room, she found the first hiccup in this plan. Becky was pleased with the way the black bra, panties and garter looked on her. Her hair and makeup were perfect. It was when she reached for the new dress, she figured out, she is way overdressed for a damn book club. Instead she decided to throw on an old shirt and baggy pants. She would have to change in the car. How could she have overlooked that?

At least Vicky had plans with her friends again. When Becky kissed her daughter goodbye, she left the house with a bag of cloths to 'Donate'. She put Mr. Dentons address into her GPS and started the drive to his place. She stopped at a mall, and changed into her new dress in the car. It wasn't easy, but she managed. Double checking her makeup, she drove the rest of the way to the gated estate. Entering the code Rosa gave her, the heavy gate slowly swung open. She parked where Rosa told her and walked to the main door.

Now more nervous than she could ever recall, she pushed the doorbell.

"Rebecca, you look wonderful. I am really happy you decided to join me tonight. I hope you didn't have any problems getting here."

"Thank your for the compliment, Mr. Denton, you look very dapper yourself. I hope I'm not late, I had to make an unexpected stop on the way here."

"I insist you call me Sam when we are out of the office. If your ready, lets go to dinner, I can show you around my home later."

Sam led her to the Corvette in the garage. Helped her in, than started the powerful sports car.

"I have wanted one of these for years, as soon as I could afford one, I had to get it. She isn't as smooth as the Suburban, but she's fun to be in." Sam told her.

For as powerful as the car is, Sam was a careful driver. He put Rebecca as ease on the trip with casual chit-chat. He pulled up to the valet at a very nice restaurant. The valet opened his door, but has long since learned that Sam would be the one to open the door for his date and help her from the car.

They were seated in a darker corner of the restaurant. After ordering, Sam asked, "Will you accompany me for a dance, Rebecca?"

"I didn't know there was dancing here."

"You can dance anywhere you hear music. Just need to look for an out of the way place." Sam told her as he led her to a corner of the room.

So formal she thought. It was like being on a date with a gentleman from perhaps the 40's or 50's. He's not that old, but he certainly exuded that era. In a strange way, it both put Rebecca at ease and excited her. Being treated like a lady, not just a date, was special. Sam learned the effect this treatment had on his dates long ago.

Dinner, dancing, fantastic food and nice conversation made for a special evening for Rebecca. She was much more comfortable holding his arm and walking back out to the car.

Back at Sams home, he gave Rebecca a quick tour. Poolside he told her, "Many of my guests like to relax in the hot tub after dinner."

"No swimsuit." Rebecca told him.

"Wearing a swimsuit is not necessary, but if you feel more comfortable with one, Rosa made sure there is a selection of sizes in the guest room. But we don't need to swim if you don't want." He said turning them back to the house.

Once in the reading room, he looked into her eyes while holding both her hands.

"Rebecca, if you would allow me, I would very much like to kiss you."

Her response was a big smile.

Sam pulled her close and they shared their first kiss ever. Rebecca thought, 'here is a man paying for my time, for sex with him, and he's asking permission to just kiss me. This is certainly different.' Rebecca was enjoying the tender kisses and began to kiss the distinguished man back. Soon the small kiss ignited into more passionate kisses. Sam was holding her close, but his hands remained respectful. She expected groping, she was ready for groping. When he broke from her kisses, he smiled at her pretty face.

"Would you like to have a seat?"

"Actually, I think I've changed my mind, the hot tub sounds wonderful."

"You should be able to find a swim suit upstairs in the guest room."

"Would you be offended if I relaxed and enjoyed the evening in the nude? Skinny dipping in the hot tub sounds wonderfully naughty." Rebecca said.

"Not at all, you can get undressed and grab a towel from the pool house, and I'll get us a couple drinks. We should have about an hour or so until you need to leave." Sam said as he headed to the house to get drinks.

When he returned Rebecca was soaking in the hot tub. The moving water blurred the view he had of her body, but what he could see, was arousing. Her naked tits were floating on the water, with her pink nipples peaking above the water now and then. Placing the tray on the ground next to the in ground tub, be stripped his cloths and lowered himself into the hot water next to her. Holding their glasses, he toasted their new arrangement and what he hoped was many years of growing friendship.

They would chat, drink, kiss, laugh and look at the stars. Sam had soft music playing. Rebecca was thinking how wonderful the night has been and what might be next.

"Penny for your thoughts Rebecca."

"I was just thinking about the evening. Dancing in a restaurant. The car, the hot tub."

"Care to dance now? I can hear music."

"Love to."

Helping her out of the water, he finally got a view of her nude body. Rebecca had seen his semi hard cock when he got into the hot water, now he was even harder. Sam held her hot, wet, nude body close to his as they danced. He leaned down and softly kissed her neck.

"Ohhh, That's nice Sam. I like that." Rebecca said. "Please don't stop."

That was the invite Sam was looking for. She was nude, excited and ready. His lips traveled up her neck, to her face. When his lips reached hers, it was nothing but pure passion. Rebecca had one hand on the back of his head holding his lips to hers. Her other hand traveled down and grabbed his hard penis. She was happy to feel he was longer and thicker than most of her previous lovers. What really made her happy, was how hard he is for a man of his age.

The moment Sam released his grip on her, Rebecca slowly lowered herself to the foot of a lounge chair. Now at eye level with Sam's hard cock, she groaned out loud. This was going to be a pleasure. She was going to enjoy servicing this gentleman.

Rebecca was just about to suck him deep into her mouth, then the atmosphere of the evening hit her. She held his veiny cock in one hand, his full balls in the other, and looked up at him.

"I would very much like to pleasure you Sam. Please let me suck on your cock. I promise to swallow your cum if you'd like that."

Sam knew he had what he was looking for in Rebecca. A willing playmate and one that appreciated the era he tried to recreate. His response was to put a hand on her head and guide her mouth over his hard dick.

Rebecca put everything she knew into this blowjob. Her personal goal was not to just have him blow his load, she wanted to blow his mind. Every trick she knew, every technique she learned, was part of this blowjob. Rebecca maintained eye contact with him as she sucked and stroked him for what seemed like a half hour. The longer it took the more determined she was. This load was going to be hers.

"Rebecca my dear, that is wonderful. I won't be able to restrain myself much longer."

Pulling herself off his cock, "Go ahead Sam. Don't hold back, I want you to cum in my mouth. I want this gift from you."

Her mouth engulfed him again. Tongue swirling, deep throat, hard sucking, licking the crown. She was stroking him with one hand, the other on his ass pulling him deeper.

"Ahhh REBBECA. HERE IT IS. OHHH. FUCK BABY. I'M CUMMING REBECCA!!!"

She pulled back so he would explode in her mouth and not straight down her throat. She sucked every drop he had to give her. When he was finished, she licked the crown of his cock. Letting a little of his cum drip from her mouth for show. The better show was when she smiled at him, scooped the glob of cum off her right tit and licked her fingers clean.

"Amazing my dear. You are amazing. We don't have too much time before you need to leave, but I would really love to taste you before you go. Lay back and allow me to return the pleasure you gave me."

Rebecca got comfortable on the lounge chair, and as gracefully as she could, opened her legs for this man to see everything she has to offer. Sam put a cushion down and knelt between her legs. The first contact was his nose nudging her clit, as he inhaled deeply.

"I love the scent of an aroused woman. So sensual. So primal. So exciting."

Sam knows how to pleasure a woman. Having many lovers over the years he knew what most women liked and what didn't work. He expertly used his fingers and tongue to get her pussy dripping. It took much less time to have her to climax for the first time than Rebecca expected.

"Ahhh Sam, Honey, Don't Stop, Oh Gawd, I'm.... FUCK. So Good. Cumming. Hard.... CUMMING HARD!!!!"

Rebecca's whole body went into convulsions. It felt like every cell in her body heated up and exploded. Everything tingled. When she came back to earth, Rebecca realized, Sam still had his mouth latched to her clit. His lips were wrapped around her clit, sucking gently on it while his tongue danced on the end of it.

"Oh Fuck, Oh Fuck, Oh Fuck. You're going to make me cum again Honey. Ohhhhhh. So. Fuck. CUMMING AGAIN!!!!!"

Rebecca could not recall that last time she felt this warm glow coursing through her body. She was sexually spent, and with just two orgasms. But they were long overdue and very hard orgasms. Sam was sitting there smiling at her when she opened her eyes.

"I think we both had a wonderful evening Rebecca. Thank you for being my companion this evening. I would really love to continue enjoy your body and the pleasures you have to offer, but we do need to get you home on time. Maybe next time we can squeeze an hour or more into the night."

Rebecca knew this was her fault. She was the one who set the time limit with Rosa, something she wished she could undo. Rebecca really hoped there would be another date in the future. They both got dressed and Sam walked her to her car.

"Thank you Sam. Tonight was very nice. You really made it special. I can honestly tell you, I was being foolish last week when I got upset. Please forgive that. You are a very nice gentleman, I hate that I may have ever thought differently."

Sam leaned over and gave her a lingering good night kiss.

"Last week has all been forgotten Rebecca. I don't think of it, and neither should you. I didn't have time today to get you flowers, an over sight that will not happen again. Please except this gift instead." He said handing her a card.

One final kiss and she was on her way home. When she stopped to change back into her book club cloths, she opened the card. It was a nice friendship card. In it was two crisp hundred dollar bills and a new fifty. Monday she would call and tell the other company she won't be changing jobs.

That night she smiled to herself. $250 and dinner, he didn't even try to fuck me yet. On top of it all, he was a kind gentleman who brought me pleasure. Rebecca thought she would hate herself for doing this, instead she was looking forward to spending more time with Mr. Denton.

Rebecca was replaying the event's of the evening while lazily touching herself as she laid in bed. She was sorry she had to leave when she did. Sam had a nice cock, she hoped she would get to enjoy it more in the future, she really wished he fucked her with it tonight. It's been so long since she's been fucked by a man. Her toys have been the only things penetrating her in a very long time.

She grabbed the dildo she kept under her mattress. She would have preferred the warm flesh of a real man, but for now, this flesh like toy will have to do. Slowly inserting the tip, she pushed the shaft deep into her. Rebecca was softly moaning, the room filled with the squishing sounds of the dildo as she fucked her very wet pussy with it. She made herself cum twice before letting the toy slip from her and drifting off to sleep. She had no way to know her daughter came downstairs for a drink, and was standing outside her door listening to her mothers soft moans.

******* Saturday Morning *******

"Hello." Rebecca said answering the phone

"Good morning Rebecca, it's Rosa. How are you doing this morning? Even more important, did you enjoy yourself last evening? I don't need details, just checking on you."

"I'm doing well this morning. Last night I had a very nice time with Mr. Denton, thank you for asking."

"Good to hear, any regrets or concerns?"

"No concerns and my only regret is I didn't have more time with him."

"Well you did set the time limit as I recall. You needed to be home before your daughter's curfew. Next time if you can't stay later, perhaps you start earlier." Rosa told her.

"I'm available today, if Mr. Denton wants." Rebecca floated the idea out.

"Sorry dear. Sam already has plans for this weekend. If you have nothing else for me, I will let you get back to enjoying your weekend. Have a nice day."

Over lunch, Vicky asked her mom about the book club. What book you reading? Who is in the book club, anyone she knew? Any cute guys? Rebecca didn't know where the interest suddenly came from. Vicky was trying to piece things together. Her mom was sure excited when she listened at the door, too excited for a book club.

******* Thursday *******

Rebecca watched Rosa go into Mr. Denton's office and close the door. The two had a long meeting that morning.

"So Sam you really think she is going to work out? I know we discussed it already, but you think we can get her to the point we had Marie at?"

"It will take some time, but I'm willing to sacrifice my time for this."

"I'm sure you are." Rosa said with a touch of sarcasm.

"Okay lets get to the real business at hand, the DQT account" Sam told her.

Later that afternoon Rebecca received a text from Rosa.

'This weeks dinner arrangement must be canceled due to a more pressing issue. Please plan on next week, if you are available.'

And that was that. No dinner date with Sam this week. Worst, no sex with him either. No sex at all since she didn't date. Rebecca was single and really had no men chasing her. She wished she was more of a flirt, but that wasn't her nature. She would have to wait for his schedule. Until then, she would make due with her toys.

******* The following week *******

'Would you be available for dinner arrangements tomorrow?' was the text Rebecca received Thursday afternoon.

'Yes! What time can I be there?' She typed back with almost nervous energy.

'Six PM?'

'Perfect.' Rebecca sent back after calculating this would give her almost six hours with Sam.

'Dinner will be at an exclusive club, a nice evening gown is requested.'

Dinner, perhaps some dancing, then back to his place. She wouldn't waste as much time playing coy. They both knew why she was there. Tomorrow night she would earn a little more cash and his hard cock.

******* Friday *******

Rebecca left work at exactly quitting time, rushed home to get ready for her date with Sam. The evening gown she got at the thrift store looked brand new and absolutely fantastic on her. It flattered her figure, made her look elegant and made her feel great. Rebecca couldn't wait until Sam saw her in it. What she really wanted to see was, the gown on the floor of his bedroom.

As with her last visit, she would drive to a remote location and get changed.

Arriving at Sam's a full five minutes early. She hoped she didn't look too eager, but tonight was not a time for 'fashionably late'. Sam opened the door when she rang the bell. He stood there looking at the woman before him. This nicely dressed woman who worked for him, was remarkable when she dressed to impress.

"My word Rebecca, you look stunning. I'm tempted to cancel dinner and just stay in with you. But that wouldn't be proper. No, I will certainly take you out. Besides, I really want the chance to show you off. Shall we go?"

Rebecca would have been fine staying in and playing with him, but she was also excited to be seen with him.

The club was beautiful, everyone dressed very nicely. Everything was very lavish. Sam introduced her to his friends and their dates. She was happy when they dined alone. Sam lead her to the dance floor a couple times and held her tightly. She was a little annoyed when his friends cut in and danced with her. What really annoyed her the most, was watching the evening slip away. Rebecca only had six hours with him, and half that time was already gone.

When they made their rounds to say goodbye, Rebecca was all smiles. The ride back seemed to take forever. She marveled at the sight of his estate when they pulled up the drive.

"You have company?" Rebecca asked.

"No why."

"Nothing, I thought I saw a curtain move. Probably just your cat."

Sam helped her from the Corvette, and walked her to the house.

"I've had a wonderful evening Rebecca. Would you like to accompany me to the hot tub? Or is the evening getting too late?"

"Hot tub sounds wonderful."

"Can you help me with the zipper Sam?" Rebecca as turning her back him and holding her hair out of the way.

Every man loved to undress a woman, and Sam was loving the opportunity to get this woman nude. When her dress was at her feet, she turned in his arms and reached up for a kiss. Sam helped by cupping her ass and lifting her a little. He helped remove her bra next, letting her full breasts spill out into the cool night air.

"As good as you looked in that dress, I must tell you Rebecca, I prefer you out of it."

He helped his playmate remove the rest of her cloths. Then it was his turn to have this pretty nude woman, helping him out of his cloths. Rebecca was on her knees when she pulled his pants down. She smiled at the tent in his pants that she caused. Next she tugged the shorts down freeing his hard cock and engulfed him back in her mouth. It's been two weeks, but she was once again giving her boss a blowjob.

Sam reached down and took her perfectly done hair into his hands, guiding her lips up and down his pole. Rebecca fondled his balls like the week before.

"Rebecca, you were beautiful in that gown, pretty standing in front of me nude, but absolutely stunning on your knees sucking my cock. Damn you sure know how to suck my cock."