Sidney

With new her connections to female high society, Tom's mother had recently met a wealthy heiress at a cocktail party who had told his mother that she was looking for a new young husband.

Her name was Sidney. Her first marriage to her childhood crush had dried up after 30 years. As he aged and she stayed beautiful, she realized she no longer felt the same way about him. Her second marriage was to create ties with a businesswoman, and he was better at cleaning dishes than pleasing her in bed. At the party, his mother had brought Tom's name up. Sidney had refused at the time, but after Tom's success as a model, she changed her mind.

She would be picking Tom up after a dinner meeting on Saturday. Tom's mother emphasized that Sidney wanted a new boy toy, not a confidant. Tom was not to speak at dinner unless spoken to.

So Tom let his mom buy him new clothes. They were in the new men's fashion, which pushed the boundaries of what was considered respectable. She sprayed him with cologne and made sure his hair was perfect.

At 5:45,Tom sat by the window waiting. At 6 sharp, a red corvette pulled into his driveway.

The first thing Tom saw were tanned, long legs. Sidney's skin was a perfect olive and Tom's eyes naturally drifted down to her red toenails in her silver strappy heels. As his eyes moved back up her body, Tom noticed how her dark brown hair flowed down her back. There wasn’t a single streak of grey, even at the roots. Tom knew women didn't age, but he still couldn't believe how her fifty plus years of life hadn't left a single mark on her body.  And despite being twice Tom's age, she would outlive him by decades. Tom had a feeling he wouldn't be her last husband.

Tom had never seen a woman walk so confidently. She greeted his mother with a kiss on each cheek. As she walked to him, her gaze overwhelmed him. Instinctively, he knelt down and kissed her shoes. Looking up, he said, "Hello Miss Sidney."

His mom turned pale when he kissed her feet, but Sidney smiled and said, "Oh Mary he's so sweet! I like that in a boy. But there's no need to be formal, Tom. We'll get to know each other very well soon enough, Sidney is fine"

As he sat at the oversized table, Tom listened in silence as the two woman discussed his fate. They haggled over the dowry, and where the wedding would be held.

After the details had been finished, lunch was over. Sidney said, "Mary thank you for having me. I need to get back home." As she walked out of the room, she turned and asked, "Tom, are you coming?"

Tom's eyes had glazed over the negotiations, but he wasn't expecting her to take him so quickly. It was dizzying to think in an hour, his whole life had changed. He knew his mom didn't think of him as property, but he wished she would show it more sometimes.

"Are we going for a ride Sidney?" he asked, struggling to keep up.

She winked at his mom. "We are, but after we get home. Come on hubby!"

Tom followed her with his bags. Her car flew out of the driveway. Tom's home disappeared in minutes. Sidney laughed as he poked his head out the window, letting the wind run through his hair. In those moments, Tom forgot his fear and lost himself in his new adventure.

Sidney's house was huge. "It's been here since the 17th century," Sidney explained. "My grandmother was one of the Founding Mothers!" She beamed.

She opened the oak doors to let Tom inside. Twelve men stood inside. At the front stood an old man and middle aged one. Tom guessed that they were Sidney's other husbands.

Sidney nodded to the older man. "Go get my bedchambers ready for Tom and I." He bowed and struggled up the spiral staircase." Sidney instructed the other man to start preparing tea. The two servants went to fetch Tom's bags, while the rest went back to their housework.

When they were alone, she asked him, "Do you like it?"

Tom said, "It's just so big."

She laughed. "Then let me give you a tour. She thought for a second and then gave Tom a wolfish grin. “We'll start with my bedroom."

Reluctantly, Tom followed her up to her bedroom. The room had a huge poster bed, a large bookshelf and a desk. But she pulled his hand towards her bathroom. The tub was full and steaming hot. She reached towards his clothes, but he protested, "We shouldn't. We barely know each other."

She laughed, and tore off his clothes. "We're going to be married. We should." As she stripped, Tom marveled at her body. She had fabulous curves and her legs were as long as he was tall. As Tom hesitated, she picked him up and pulled him into the tub with her. As she wrapped her long legs around his body and kissed him, the feeling of her skin and the warm water washed away Tom's decency. He knew he should feel awkward being naked with a woman he just met, but something about her legs encircling his body made him feel safe.

He conceded, "Ok but only if we take things slow"

Sidney laughed, "I get to make the rules Tom. You just get to obey them." Thankfully she did let him go slow. He started by massaging her back in the sudsy warm water. As he kneaded her shoulders, she turned to kiss his neck. He smiled and moved down to her legs. He licked the length of her legs and adored her feet, licking the soap off her wrinkled soles and sucking the water off her red toes.

Suddenly she pulled him under the water, pressing him to her crotch. He fought for air as he sucked her clitoris; equal parts turned on and scared. After Tom's breath was almost out, she let him up and pushed the pill in his gasping mouth. She leaned him back in the tub as she mounted him. She whispered, "Make me cum, you little slut". Tom happily obeyed.

After she had finished, they lay in the lukewarm water. Tom sighed, "Sidney, I've never had sex like that!"

Sidney smiled, "Then we'll have to try it again soon Tom. But first I need you to get ready for tonight's dinner party."

"Dinner party?" Tom asked. His mind was still focused on her naked body.

Sidney ran her hands over his chest and said, "Why do you think I picked you up today? I needed a new boy toy for my soirée tonight!" She pulled him out of the tub and smacked his ass, "Now go get ready, you little slut."

Tom dressed in his best dinner jacket and met Sidney downstairs. She was seated in a high back leather chair. She had six servants attending her. Two servants massaged each of her feet, while two more filed her fingernails. The fifth did her makeup and the sixth brushed her hair. There were steps tools around her chair to allow her servants to reach her.

Her other servants ran around, cleaning and setting the tables. They carried ice buckets and plates.

"Tom you look amazing." Sidney said.

"So do you Sidney." Tom knelt before her. It seemed appropriate, considering how regal she looked.

"Get up Tom" she laughed. "I need your help with my dress." She was wearing a long strapless evening gown, showing off her tan shoulders.

As he climbed up into her lap, Sidney asked him, "Tom can you adjust my top?" She pulled at the red fabric attempting to cover her cleavage. " It just doesn't fit right."

Tom reached up and began to massage dress into place. Sidney's breasts were bigger than his head, and were heavy. He struggled to hold them as he adjusted her dress. Sidney noticed his difficulty and asked, "Are my boobs too big for you Tom?"

"Not at all Sidney," Tom gasped. "They aren't heavy at all!" Unfortunately, his hands slipped and he fell face first into her cleavage.

Tom had never seen Sidney laugh so hard. As he tried to get up, he felt her hand push him back down to her breasts. With one fluid motion, she pulled her dress down to reveal her pink nipples, completing in seconds what Tom had tried for minutes to accomplish. She asked, "Are you sure they're not too big for you Tom?" and pushed her nipple towards his mouth.

Tom didn’t even try to reply, he just eagerly opened his mouth and sucked. As she began to moan, a new voice said, "I see you started the party without me!"

Sidney pushed Tom off her lap and hugged her friend. “Jackie I'm so glad you could come!" Jackie was a brunette with huge brown eyes. Her southern accent was entrancing, and her cocktail dress was incredibly elegant. Tom now knew why so many men fell for southern belles. The two women hugged. "Jackie this is my new slut" Sidney said, pointing to Tom.

"Oh he's cute!" Jackie drawled. "And from the way you were moaning, he's talented too!"

"Very" Sidney replied. "Who's your pet?"

"This is George. I figured if you were getting a new boy toy, I should too."

Sidney's other friends arrived shortly after Jackie. Julia was a gorgeous redhead with piercing green eyes and Carrie was blonde with the longest legs Tom had ever seen.

The four women all sat down at the table and placed their boys on their laps.

Their dinner was exquisite. The women drank champagne, nibbled on caviar, skewered salads, and devoured steak. It was the most food Tom had ever seen in his life. The conversation flew and as the women became drunk, they decided to create some entertainment.

The women would pick a task for their sluts and whoever completed it the quickest received a table scrap as a prize. Tom won the first task, which was to make their mistresses cum from oral. Sidney gave him a bite of caviar, and laughed as he gagged from the taste.

Tom also won the second task, which was toenail painting. He was able to try a bit of champagne, which he enjoyed much more than the caviar.

But the alcohol made him dizzy and he wasn't able to make Sidney cum first from rimming.

But even drunk, he was able to make Sidney cum first when they had sex. He got another sip of champagne as a reward, and the rest of the night became a blur.

He vaguely remembered trying to please Sidney and Jackie at the same time with his tongue and cock. But he distinctly remembered the girls all being very impressed with his ability to pleasure a woman. After Tom had drunk many sips of champagne, Sidney took him to bed, where they both had sloppy drunken sex.

Tom quickly fell back into the life of a pampered pleasure pet. Tom expected Sidney’s other husbands to despise him, but to his surprise, they didn't. In fact, he barely saw them. Sidney ran a very orderly house and liked to keep her servants busy. Tom didn't mind, as that meant he had more time for leisure and pleasure with Sidney.

They danced at balls, did dirty things on secluded beaches, and Tom spent some days just making Sidney cum as many times as possible. But his favorite times were the tender talks after, the candlelit dinners, even the way they made things like shaving her legs into foreplay.

One time, Sidney even told Tom what life in the 60s was like when she was a girl. He loved hearing her tell him stories of an era that was decades before he was born.

One Friday, Sidney asked him if he had a tuxedo. When he said he didn't, she took him shopping. They bought a matching tuxedo and evening gown. Tom helped her pick out a set of high heels. She even picked his favorite pair black stilettos with gold ankle straps.

After they finished, she told him that she'd be taking him to the President's Ball, the most famous black tie event in the country! Tom was thrilled.

The event was like a fairy tale. A photographer took their picture on the red carpet. He was surrounded by some if the most famous women in the country! He spotted Senator Felton, but thankfully she didn't recognize him. The women sat in assigned seats at elegant tables, boys in their laps. Provocatively dressed waiters brought hors d'oveurs and alcohol. Although the event was televised, Tom was sure people at home saw a good bit of fondling. The president herself had her six husbands adoring her throughout the dinner. While Tom’s eyes glazed over while the politicians talked about their plans for the country, he did notice how beautiful and elegant they all looked. Politics never really interested Tom, since men couldn’t vote anyways. However, he loved dancing with Sidney on the ballroom floor. He knew this was a night that he would tell his sons about. By the end, Tom was so tired he nearly collapsed on the last dance. Sidney carried him back to the table and he dozed on her chest.

After the night was over, they walked to her bed, Sidney said, "I had a great time tonight Tom...but I'm not ready for it to end juuuust yet." She tugged at his tie.

Tom was drained. It had been a long night. "I'm exhausted Sidney, can't we do this tomorrow?"

She frowned. "Tom, when we marry, what are you going to say to me?" She asked.

"To love, support, and obey you in everything." Tom said.

"So obey me,” She said as she unzipped his pants.

"Seriously Sidney, stop it!" Tom said.

She responded by ripping off his underwear. "I make the rules Tom. And don't act like you don't want me, you little slut."

"Sidney you know I hate when you call me that. I...mmmph" Sidney kissed him hard, slipping the pill into down his throat with her tongue.

Tom started to get angry. He tried to push her off with all of his might. She didn't even move. "Sidney, I said no!"  Tom protested.

"And I say yes Tom. Sluts don't get to say no. Besides, I know you want me. You dick certainly does." She began to run her legs across his body and once he was completely hard, pinned him and lowered herself down.

Tom's mind raced. How could she do this to him? But then...something else began to take over. A primal urge, one that overrode logic. Tom found himself liking it, and wanting more. He was her toy, and toys couldn't refuse. Toys were used to pleasure their Mistresses. There was something hot about her using him like a toy. He bucked his hips and kissed her.

She felt him breaking. "Tell me you want me to fuck you,” She moaned. "Tell me that you're a bad little slut."

"Please fuck me Sidney" Tom gasped. "I am a bad little slut... I'm your toy. An object for your pleasure." When she heard that, Sidney came again and again, soaking Tom’s body with her cum. It was the most passionate sex Tom ever had.

After she finished, Sidney started to fall asleep. But Tom realized his job wasn't done. He moved his head in between her legs as she moaned. He quickly had her soaking him in her cum again.

As they paused, Tom told her. "Sidney you were right. I do need to obey you."

She laughed, "Like you had a choice!"

Tom continued, "But I should mean it. From this point forward, I promise to obey you Sidney. You taught me today that I'm your slut and today I learned that I like it. I love you Sidney"

She said, "Aww Tom! I love you too"

The next week was like a dream. Tom learned how fun obedience could be. There was something comforting about not having to think. He just simply did as Sidney asked.

One lazy Sunday night, Sidney said, "Tom I want you to be my slut."

Tom kissed her and said, "Sidney, I am your slut."

She shook her head. "No Tom I mean my slut outside of the bedroom." She continued, "An actresses wants her son to marry me. In return, she'll get me an acting job. But she’ll only do it if I don't marry again for another ten years. I want you to be my slut for those ten years and then I'll marry you."

Tom was shocked. People used slut as a derogatory term for loose men all the time, but a true slut was a boy a woman kept around for pleasure, but didn't marry. It was a precarious position for men, because as soon as they stop pleasing their woman, they were forgotten and kicked to the curb.

He didn't know what to say. He loved Sidney but could he be her slut? "Will it change things between us Sidney?"

She laughed, "Not if you keep pleasing me like this. I've had the best sex of my life with you. Your tongue just doesn't quit!"

"And if I don't?" Tom asked.

"Then you'll join my servant staff." Sidney waved her hand. "But if that happens, I'll give you plenty of chances to work yourself back into my good graces."

Tom felt deeply hurt. He couldn’t believe she didn't want to marry him. Had she even planed on marrying him? He considered running back to his mother. But then, hadn't Sidney always known what was best for him? From their contract to when she took him, she had always made the best decision for him. Obedience meant trusting her. Plus, he was twenty years old. Most men his age were already married. Sidney might be his last chance for love.

After a long time, he told her, "Ok I'll do it."

She said, "Oh Tom I'm so glad you want to. I'll get the contract and we can amend it"

Tom said, "Of course Sidney. But I have to get some things from my house first. Things I left when I first moved."

Sidney raised an eyebrow. "Tom are you sure that's wise? You mom may ask questions."

Tom shrugged, "I'll be out before she notices. Plus, I can keep a secret"

She smiled and drove him to his mothers house. Tom snuck in the back door and began to pack.

He was packed and ready to leave, when his mom found him. "What are you doing Tom?" She asked.

“Just grabbing some things Mother” Tom stuttered. He had always been a bad liar. His mom simply raised an eyebrow and glared down at him. Tom tried to think of a reason why, but her stern broke him down. "Mom, Sidney isn't going to marry me." Tom confessed. "She just wants to use me for her own pleasure." He looked down. "She wants me to be her slut, and I'm going to do it. I love her."

His mom's hand flew out of nowhere. The force of her blow knocked him to the ground. As he struggled to get up, she leaned down and snarled, "You will do no such thing." She made him unpack his bags and made him tell Sidney he wasn't coming.

Before he went to bed, she said, "Tom I'm tired of trying to find you a wife. Starting tomorrow, you will join my servants. If I die before you, one of your sisters will inherit you as part of my property."

The walk to the servant's quarters was the lowest point of Tom's life. The next morning, he served his mom breakfast with the rest of the servants. She didn't even notice he was there.