First time for everything

The car pulled up to the discreet mansion in the hills of Los Angeles. Nancy stepped out of the car and smoother her dress. She motioned for her new boy toy to follow her. He zipped his raging erection into his pants and stumbled out of the car, eager to continue what they had started en route to the house. He was taken aback by the elaborate home they’d arrived at.

“Is this your house?” He asked mouth slightly agape.

“Yes, please come with me.” She smiled alluringly and walked to the front door. She entered a code onto the screen next to the door and light thump was heard and one of the double doors began to open out onto the stoop. She entered, looking back to make sure her prey had followed her. She was pleased to see that he did so unquestioningly.

They entered a large foyer with a staircase up to the next floor perched further back and to the left. The man looked at the sparing decadence, past the stairs to a large kitchen and a view. “You never said you were rich.” He laughed lightly.

“I dont like to advertise it, it helps keep me grounded.” She said walking up the steps.

“Your shoes sir.” David nearly jumped out of his skin as he noticed the butler for the first time.

“Oh right of course so sorry.” He said flustered and removed his shoes with great effort with untying his laces. He held them sheepishly before the butler indicated a small wooden rack near the door, David placed them on the empty rack and turned to see his date had dissapeared up the stairs.

He stood awkwardly for a moment and looked at the butler. He was wearing a casual fit with a sweater and khakis, he looked at him with some curiosity but was otherwise unreadable. “So, uh, should I wait here or..?” He said cautiously not sure how to speak with him.

“You may do as you wish. I believe Ms. Remington went in the direction of the bedroom upstairs to the left, if that helps with your decision.” He said with a hint of good humor.

“Ah thank you. Does she do this often?”

“Right.” The butler said, judging him unfavorably for asking.

“Sorry, okay. See you later!” David said, deciding to focus on what was most important.

“I’m sure of it.” The butler replied meaningfully.

David crossed the room to the stairs and took them almost two at a time. When he reached the top he looked left and right, curious about where he’d found himself. He could see 3 doors on the right and 1 large set of doors on the left. Having found the room he expected to be the master bedroom he took a left and headed towards the door.

“Where do you think you’re going?” A sensual voice called out to him. He turned and saw Nancy standing in a room he hadnt seen to his left.

“Oh sorry, you’re quicker than I thought.” He joked. She did not smile and just motioned for him to join her. The room appeared to be some sort of lounge with a bar. He stepped in and admire Nancy. She looked great in the low light of the room. She stood by the bar selecting a couple of glasses and a decanter of a brown liquid.

“I prefer aged bourbon, would you like one or something a little less harsh?” She asked.

Afraid to say no he accepted. “I don’t drink much but I enjoy a good sip of bourbon every once in awhile.” This was a lie, he had rarely had bourbon outside of mixed drinks and was not much of a drinker in general.

“Good.” She smiled lightly and poured him a glass. “Rocks?” She asked.

“Yes please.”

She dropped a square ice cube into his drink and handed the glass to him, she didnt add any ice to hers. After handing him the drink she made her way to a couch at the foot of the bed. She threw back her drink to drown the nerves. She’d been planning this for months but now that she actually had her prey in the room with her she was feeling anxious and excited. This was a crucial step in her plan and failure could mean a large setback.

“Wow, you tanked that without a problem.” He sounded surprised and made an effort to drink his quickly. The burn made him cough as he finished his drink, the ice having not even begun to melt.

“I hope I’m not scaring you away, I don’t like to waste time.” She removed her shoes and flexed her toes, uncomfortable from the tight heels she had been wearing. “Would you pour me another glass please, make it a double.” She held out her glass and he took it and went to fill both of their cups. There was a variety of bottles, mostly unopened on the table and he selected the decanter that she had used before. He poured her drink and then paused. The bourbon had not been much to his liking and he would prefer something clear if he was going to keep drinking. He selected a small bottle of clear liquid that was unsealed and unlabeled and smelled it. It smelled strong but a little sweet so he filled his cup to a respectable level and turned to face her again. He stopped dead in his tracks as he realized his host had removed her dress and stood in black lingerie before him. Her breasts spilled over the cups of the top and the thin undergarments barely covered her puffy lips. The straps connecting the upper and lower pieces accentuated her wide hips and toned belly. Her dark hair was pulled up into a ponytail that draped down behind her back. She had slipped into a pair of stockings that complimented her toned thighs and long legs. His erection returned with fervor.

“You can put those on the tray there.” She gestured to the side table at the edge of the couch. He complied, unable to find words and not wanting to ruin the moment. He bent to place the glasses down and Nancy took a deep breath. “On your knees.” She commanded, her voice holding despite the nerves. She was satisfied with how strong it felt and she could feel the heat between her legs spreading.

The man hesitated for a moment and then smiled and knelt to his knees. She wished she’d had him undress first but the moment had passed. She sat on the couch and spread her legs. He crawled forward guessing what she wanted and hoping he was right.

“Ah-ah very hasty aren’t we.” She placed her foot on his shoulder, keeping him from burying his face between her legs.

“Did you not want me to do that?” He asked timidly. He was getting mixed signals.

“I don’t think you’ve earned the right for that yet.” She held her foot up in front of his face. She didn’t particularly care for foot play but she liked the feeling of power it gave her. She needed to establish a dynamic here and a slow build felt like the best path to success. She could tell he was nervous and she needed him compliant.

“Yes ma’am.” He replied, getting the message. He took her foot in both hands and began kissing her toes. He didn’t know what to do with it and tried to read the signals. He kissed the bottom of her foot and she sighed in satisfaction. He licked the bottom of her toes through the stockings and she moaned a little. He took all her toes in his mouth and she moaned louder. His cock was ready to rip through his pants. He continued to worship her foot, kissing and licking. She began to shove her foot into his mouth and he allowed this. Her moans grew louder and her shoves grew more aggressive. He felt like he was being pushed backwards. He knelt back on his haunces and a particularly hardy push had him back flat on his ass. She stood and pressed her foot against his face, pushing him to the ground on his back. She stood over him, her foot planted on his face as he licked at the bottom of it. He could see her lips getting wet and she was smiling and flushed. She rubbed her breasts with one hand.

Nancy came to, realizing what she had just done. She had gotten carried away with the power he gave her and she feared she had taken it too far. He was prone on his back and she was practically standing on his face. This was not first date behavior and she knew it. ‘Fuck it’ she thought to herself, she wasnt a normal woman. He was lucky to even taste her at all. He hadn't fought this, she could see his cock through his pants, she realized she had won this first fight.

She shifted her weight, pressing down on his face and moved her other foot to carry more of her weight. She dragged her foot down towards his swollen member and pressed it against where she thought his balls met his cock. Bingo.

“Ooh.” He moaned and started as her foot pressed into his manhood. The pressure at the base of his cock sent waves of pleasure up and down his legs, but the pressure on his sack caused him to startle a bit. It felt like she had put her foot down on his stomach and a light twinge of pain shocked through his gut as she twisted her toes and ball of her foot.

“Maybe a little higher.” He said timidly.

She pouted at him sticking her bottom lip out a little bit, “I’m sorry, can the big boy not handle my little foot?” She pressed a little harder and ground her foot lightly into his crotch. He began to struggle a little bit, trying to shift his pelvis to avoid the pain. “Aww, look at you squirm. Doesn’t it feel good?” She teased him.

“It does feel good.” He moaned as she began to rub her foot up and down his shaft.

“It does feel good, mistress.” She pressed her heel against his balls, pinning them lightly against his taint.

“It feels good mistress!” He cried out, trying to crawl away on his back. He came up against the wall and she followed.

She stomped lightly on his crotch and he doubled over. “That should teach you some respect. Its a shame, I was just starting to have some fun.” She pouted again.

He looked up at her, his gaze tracing her toned body. He had a better view of her ass from this angle, accentuated by her underwear it was stunning. It was paler than her legs but well toned, it protruded from her back and thighs with a perkiness that made him want to let her do anything she wanted if he could just get her bent over anything in this room.

“You like my ass?” Her tone grew accusatory.

“Yes.” She ground her heel into his balls, harder this time. He yelped “Mistress! Yes mistress I like your ass.”

“Good boy. See you are a quick learner with the right incentives.” She released his manhood from the pressure of her foot and strode over to the tray. She took her drink in hand and downed it in one quick motion. She was feeling her confidence now. “Thank you for the drink.” She cooed.

He sat there dumbfounded for a moment. He couldnt decide whether to take off all his clothes or run for the hills. This woman was clearly a little bit insane. On the other hand the best sex of his life seemed to be right around the corner. He stood up and removed his clothes, thinking it would show confidence. It was his turn to tame her. His shirt came first. Nancy say back in the couch and crossed her legs. She reclined as she observed her new pet. He whipped off his jeans and boxers in one motion and stood confidently in the middle of the room. His penis stood at attention and he watched to see what effect this would have on his host.

Nancy smiled, his show of confidence was surprising but she remained reserved. She would let his confidence dwindle and soon he would melt in her hand.

He stood defiantly for a few seconds and then dropped his arms. He wasnt sure what he had expected to happen. He guess hed hoped she would jump at the chance to start sucking his cock but that felt a little silly now. He realized that he had opened with letting her humiliate him and that was going to be a difficult thing to climb back from. He decided to double down and brute **** the situation.

“Suck my cock, wench.” He hated it as soon as it left his mouth. His voice was weak and wavered. Nancy smiled and stifled a laugh. He was perfect.

“Hmm. Perhaps I will, but you’ll have to earn that too. See I’m not a harlot and I’m no slut, I don’t fuck on the first date. I like to make sure my men are loyal first. You have a nice tool and you did well in your first test, but I need some more convincing. Lets circle back to this next week shall we?”

He stood there dumbfounded. His balls ached and he had half a mind to stroke one out right here if she wouldnt have sex with him.

“Gather your things, but dont dress just yet. I have a little surprise for you. Call it a test of willpower. Matilda!” A light on the bedside table lit up and began blinking. Moments later a maid in a short skirt and black dress top came in. Her midriff was exposed and he was surprised to see that she was gorgeous.

“Matilda, please fit this young man for his belt and bring the necessary equipment. He also may need some assistance with that.” She pointed at his cock.

“Right away madam.” Matilda nodded and walked over to David. She had a glove on one hand and reached down to grab the hilt of his cock. “Pardon my reach sir.” The glove felt cool and had some liquid on it. She began stroking his cock slowly at first and then faster. Pleasure and confusion raced eachother in his brain. Nancy watched amused from her perch on the couch.

“Oh Matilda, he’s been a good boy, I really put him through it, why don’t you give him the special service? Do you mind?” Nancy smiled and seemed to almost find the situation funny.

“Of course madam.” Matilda stopped stroking his cock and instead turned away from him and bent over, showing her tight round ass to David. Her brown skin was smooth and she word no underwear. There was some kind of plug in Matildas asshole and she was spreading her lips to allow David easy entry.

“Im confused,” david finally spoke up. “I came her for you.”

“Please, I insist. Consider Matilda a test run.”

“Please fuck me sir.” Matilda begged from her bent position. She seemed eager and David couldnt resist. He lined his lubed up cock up with her hole and pressed into Matilda. Her pussy was warm and wet and tight. She began bouncing on his cock before he even had the chance to thrust.

“Yes sir, oh god sir, please sir.” Matilda began moaning and begging for his cock. David felt awkward being watched by Nancy as her employee acted like a whore. But Nancy seemed to be enjoying herself, she played with one of her nipples and watched hungrily as Matilda did her work. “Enjoy her. I wont let you fuck anyone else but me after you’ve filled Matildas womb with your seed.”

This was all the encouragement he needed and he grabbed Matilda by the hips and began reaming her as hard as he could. He wanted to perform for Nancy, to show her what he would do to her when he finally got his hands on her. Matilda moaned and squeezed his cock. Nancy stood and walked over to the pair. “Dont stop on my account.” She bent and grabbed the plug in Matildas ass. She squealed as Nancy yanked it from her ass, leaving it gaping. It was a 4 inch plug but relatively slim. It was lubed up and warm from resting in Matildas asshole. Nancy bent and kissed Matilda on the lips. Matilda moaned “thank you mistress, thank you for letting me get my slutty pussy fucked.” David noticed that Matilda had stopped saying madam.

Nancy stood and turned so that her ass was directly in front of Matilda. She unclipped the string of her panties, exposing her crack and ass in all their glory. David felt Matilda pull away from him slightly as she shoved her fact into Nancys plump ass. Nancy placed her hands on the back of Matildas head and pressed her deeper. David watched as Matilda licked every inch of Nancy ass that she could reach, bouncing as he fucked her from behind. Her head would pull away as she backed onto his cock and then dive back to slurp at Nancys tight asshole. Nancy moaned a deep moan David had not heard yet. “Yes good girl. I want you to clean every drop of sweat from my asshole. I want to feel your lips on my hole and your tongue deep inside me. Worship it!” Matilda held her face between Nancys cheeks, barely stopping to breathe. David could hear her licking and moaning and longed to switch places with her. He grew frustrated and began pounding her harder, jealous of Nancys attention to the maid.

“Are we getting a little jealous? Let me fix that.” Nancy stepped forward, removing Matilda from inside her ass. Matilda moaned in frustration. Nancy made her way around behind David and caressed him. “Is this what you wanted, my attention?” Matilda started bouncing faster on Davids cock, looking back at Nancy.

“Let me show you what I have in store.” Nancy smiled and before David could react, he felt something hard and warm pressing against his sphincter. Before he could pull away Nancy shoved the plug into Davids ass. It hurt for a moment and then a wave of pleasure coursed through his ass to the tip of his dick. Nancy was shoving the plug as deep as it would go and twisting it around. David couldnt hold back any longer and he climaxed, filling Matilda with cum. Matilda cried out “Thank you sir, thank you for cumming deep in my pussy.” She did not stop bouncing. “Milk him Matilda.” Nancy said, still toying with Davids prostate. David had never cum harder or longer, spurts of semen coated every inch of Matildas greedy pussy. “We want his balls empty!” Nancy commanded. David couldnt take much more and tried to pull out but to no avail.

“Ooh” Matilda moaned as she pressed her ass against Davids hips.

After what felt like minutes David was spent and shaking. Nancy removed the plug from his ass and walked around to Matilda. She shoved the lib coated plug into Matildas mouth and strapped it in. David pulled away and slumped against the wall.

“Get him fitted Matilda and call the car around.” Nancy said, stepping over to the couch and picking up her discarded clothing.

“That was…that was amazing.” David said still breathing hard.

Matilda had fallen to her knees, still shaking from her orgasm. Davids cum dribbled from her puffy lips.

“Yes mithtreth, right away mithtreth.” Matilda sputtered around the gag in her mouth. “Come with me sweetie” she said removing the gag and standing up straight, seemingly recovering on command.

David followed Matilda out into the hall, still in a daze.