Celebrity Story Site
Stories & Art => Celebrity Stories => Models => Topic started by: Cadeauxxx on December 31, 2025, 04:29:13 AM
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Try Me: The Card Game
Starring: Penny Lane
Themes: Big Tits, Comedy, Seduction
Disclaimer: This story is purely fictional. This is fiction, it did NOT happen. Fantasy is legal. Please do not copy this story to any site without my permission.
This story as well as all the other Try Me chapters is written for Galva82. The celeb choice was his, along with the ideas.
If you want to read other entries in the series first, here they are.
The original trilogy: Pt. 1 (https://celebritystorysite.com/index.php?topic=3831.0), Pt. 2 (https://celebritystorysite.com/index.php?topic=3883.0), Pt. 3 (https://celebritystorysite.com/index.php?topic=3983.0)
Sequel trilogy: Pt. 1 (https://celebritystorysite.com/index.php?topic=4043.0), Pt. 2 (https://celebritystorysite.com/index.php?topic=4080.0), Pt. 3 (https://celebritystorysite.com/index.php?topic=4126.0)
Further sequels: Pay To Play (https://celebritystorysite.com/index.php?topic=4192.0), I'm Better Than Her Pt. 1 (https://celebritystorysite.com/index.php?topic=4265.0), Pt. 2 (https://celebritystorysite.com/index.php?topic=4289.0), Big Boy! (https://celebritystorysite.com/index.php?topic=5146.0)
(https://i.postimg.cc/LX418Hrr/pennylaneisthename-2024-05-15T000512-000Z.png)(https://i.postimg.cc/C1MqxFW3/Penny-Lane1.png)(https://i.postimg.cc/DZfXw2tR/Penny-Lane2.png)(https://i.postimg.cc/rmyrw8vb/pennylaneisthename-2024-05-15T000512-000Z-1.png)
Nassau, Bahamas
Another day on the clock and time passing by slowly with the strong scent of carpet cleaner. Anthony stood tall, hands on his hips and sighing as he looked down at the rug. This made the third consecutive day he was stuck on cleaning duty. The liquid smell was giving him a headache after scrubbing the carpet in one of the luxury suites on the higher floors. Maybe it was allergies, but then again, Anthony couldn't care less. This was all part of the job after years had passed by at the Rosewood Baha Mar hotel. Now that it had become a career for him, Anthony knew better than to complain. He reminded himself that scrubbing stains out of carpets was better than the janitorial work downstairs on the lower floors. He let out a sigh after collecting his bottles of liquid spray and placing them back on the maintenance cart. A wet stain was visible on the end of his white shirt. Anthony couldn't care less about his uniform becoming dirty. As long as it wasn't the clothes he purchased, the stain could remain for all he cared.
Much of the year had passed by in a breeze with the dullness of pain and sorrow. After turning thirty, Anthony began to ponder his situation in life. By now he had spent most of his adulthood far away from home in the Bahamas. It didn't bother him until his birthday passed and he began thinking about what his life had amounted to. His gambling days were over now that he was locked into a career path. The end of his day was a lonely experience without a bed to share with someone. Scott was still his only real friend at work. He annoyed everyone with his blabbermouth and obnoxious demeanor, but Anthony didn't mind. Without Scott, he would've lost his mind in loneliness. The two men had their fair share of lucky times a few years back. Anthony didn't mind all the bragging Scott had done about the famous models they knew. It was the highlight of their lives. Sometimes he thought about how funny it was to be stuck in one of the most sought-after vacation spots, yet live an isolated life there.
He thought about it again at the beating feel of a headache. The carpet cleaner always set off his allergies, but Anthony didn't complain to the managers. It was best to not raise an issue with the supervisors. Despite the daily grind, he enjoyed this job. All of his money was currently saved until he was ready to figure out what he wanted to do with his life. He hoped to have decided his future before he reached the age of forty. At least for now, he was grateful to still be in good shape. A layer of tiny hairs covered his face in a five o'clock shadow as evidence of not shaving in the past day. His blonde hair has grown past his ears. A haircut was in store, yet Anthony was hoping to wait until the end of the year. He wanted to go into 2026 starting over fresh with his look. So far, he had managed to avoid the one temptation that always led to bad times in his life. He thought about gambling anytime when stuck alone, his mind wandering through the events of his life. Every now and then, he'd use an old poker deck to arrange a table and play around with the cards while alone. There was no way he could lose against himself.
Pushing the car down the hall, Anthony tried not to think about those subjects. When he was by himself, it was easy to get caught up daydreaming while working. The wheels squeaked as they rolled across the carpet floor. A man in a suit stepped by, almost knocking the cart into the wall. Anthony stopped and let out a low sigh. The rudeness from guests was common at times. It was a common subject among discussions in the breakroom. Anyone who had worked there more than five years had their fair share of stories throughout the years. Anthony didn't pay it any mind as he approached another room and reached for the doorknob. A slight push opened the door to reveal an empty room that appeared clean on first glance. He stepped in front of the car, tugging it from behind as he walked in. His eyes scanned across the room, observing the situation further. Anthony then wandered to the bedroom area. The blankets were pulled back, and he could see the traces of liquid stains across the white sheets. He smiled, easily guessing what the guest must've done. Someone else could come and pull the sheets and do proper laundry. Anthony noticed the bathroom light was left on from the right side of the room.
As he stepped in, something caught his eye on the counter. Next to the sink was a small deck of cards held together by a brown rubber band. The black color of the cards stuck out against the white stone surface of the counter. As Anthony reached for them, he noticed a red X drawn on the back. Upon grabbing the cards, he flipped them around and removed the stretching plastic band. His eyes widened, and he chuckled at the first card. It was printed with a silhouette drawing of a man and woman engaged in a sexual act. The red text read 'deep penetration.' The card behind it was similar with a different position. Blushing at the contents, Anthony couldn't believe someone had left this behind. Whether it was a custom deck of cards or a sold product, he was amused by this discovery. The deck was of twenty-five cards total. All of them with a different position, some more obvious than others. As he flipped through them, he heard footsteps outside. His gut instinct was to hope it wasn't the guest returning to retrieve something they left behind. He quickly shoved the cards into his left side back pocket.
"Hey Anthony! Are you in here?"
The voice belonged to a man. Travis was one of Anthony's many coworkers sharing the same shifts with him over the past few months. A black man in his early twenties who had been hired earlier in the year. He was tall, skinny, and sporting a short afro. Anthony left the bedroom to meet him. The other man stood there, hand on his hip, looking over the room.
"I'm right here. What's up, Travis?"
"I was wondering if we could trade shifts right now. There's a lady down at the lobby who needs help with her luggage. You know I pulled my shoulder last week."
Anthony nodded. Travis shouldn't have been on duty today, but a paycheck was better than nothing to look forward to on Thursday afternoon. He understood why the man didn't use any of his sick days.
"Sure thing. You need to call downstairs and let them know that the bed needs to be stripped and cleaned."
"That's not a problem for me, man. The woman is waiting in the lobby. She's wearing a white skirt and big black sunglasses. Look no further."
Relieved to get out of this situation, Anthony left his cart behind as he walked back into the hallway. At least he had a break from smelling carpet cleaner. The headache still lingered as he entered the elevator. From the seventh floor all the way down to the lobby, Anthony sighed in relief at the sound of people talking as they stepped by. He enjoyed seeing the many guests coming and going on a busy afternoon. Holidays were around the corner, and people would be checking in for vacations. As he glanced around the large room, he spotted a woman standing around the reception desk with two black luggage bags. She was tall, even without the white stilettos covering her feet. Her dress had shoulder straps and heavy cleavage nearly spilling out. On second glance, Anthony was impressed. She was busty, yet also looked familiar to him. Something about her was different from a normal guest. Her long blonde hair was pulled up in a ponytail draped over her shoulder. Anthony approached her, smiling as he waved his hand.
"Hi, do you need some help carrying your bags?"
The woman raised her sunglasses, looking at Anthony with a set of big blue eyes. Under the right eye was a subtle beauty mark on her cheek.
"Good afternoon."
She spoke in a heavy British accent.
"The gentleman who gave me the key to my room said that someone would return to help me. I assume that is you?"
"Yes, that's me. My name is Anthony."
"I'm Penelope, but call me Penny. It's a pleasure to meet you."
"The feeling is mutual."
The smile was still on her face as she watched him lean down to grab the handle of her black bag. It was heavier than Anthony anticipated. Once he lifted it from the ground, he grabbed the other bag.
"Damn, these are heavy. Did you manage to carry them all in by yourself?"
Penny shook her head.
"My driver was kind enough to carry them to the desk before departing."
She stepped forward as his eyes wandered. From behind, Anthony saw an impressive buttocks contained within her tight dress. Penny glanced over her right shoulder, as if she knew he was checking her out by instinct. Anthony knew it was rude. He pretended not to notice before glancing down at the floor. Together, they walked towards the elevator. Anthony decided to use a different one instead of the one he came out of.
"Which floor is your room on?"
"The fourth. I'm in room four-oh-three."
He joined her in the elevator. Penny pressed the button since both of his hands remained full. They were alone in the small space, standing shoulder-to-shoulder. For some odd reason, Anthony felt he had seen her before. If not in person, perhaps in print or photos online. She resembled a few models of his past. Anthony tried not to think about those memories as he glanced in her direction. Penny caught his wandering eye and smiled. Not wanting to be rude, he tried to change the subject from her.
"What do you have in these bags to make them so damn heavy?"
"My camera and tripod are in one. The other is clothes."
"You must've packed a lot for it to weigh a ton."
Penny laughed. The sound of her accent coming out strong made Anthony think about another British woman. A special woman who had given him some of the best days of his life.
"Where are you from, Penny?"
"I'm from England."
"I knew that by the sound of your voice. Where at in England?"
"Cheshire. Have you ever visited there?"
Anthony shook his head to answer her question.
"I'm from America, which you probably already guessed."
"Ah, yes. I can recognize it in your voice."
The elevator stopped after she replied. Anthony was the first one to step ahead as she followed alongside him.
"I appreciate you carrying my bags all this way."
"That's my job. Why do you need a tripod and a camera? Are you a model?"
She glanced over at him with a wide smile across her face.
"Yes, I am. Penny Lane is the name."
Penny Lane. Something about that name was familiar. Anthony walked with her until they reached the door. He glanced at the white walls of the corridor, then it suddenly clicked in his mind. He had seen her online as a new model in last year's Sports Illustrated swimsuit edition. No wonder he believed that he had seen her somewhere. So much time had passed since his last encounter with a famous model. Wealthy guests were common at the Baha Mar due to the high price of rooms.
"I knew I had seen you before! You were in Sports Illustrated."
A small grin ran across her pink lips. When Penny opened the door, Anthony stepped in behind her.
"Where do you want me to set your bags?"
"Close to the couch is fine."
A wooden refectory table sat across from the couch. It was part of the new package for the hotel rooms, replacing the old furniture. The couch was blue velvet. All the furniture in the rooms was wooden, and the walls were freshly redesigned with white wallpaper. Anthony stepped toward the table. He leaned forward to carefully place the bags down onto the floor.
"Sorry if I'm asking too many questions. I'm just curious. Are you shooting your own photos here?"
As he spoke, he turned around to face her. Penny placed her hands on her hips and shook her head.
"No, I'm meeting with a new photographer here. The camera and tripod are for him. He's an old friend, and I forgot his birthday last month, so I'm bringing him a belated present."
Anthony smiled.
"How very kind of you."
"I never forget my friends. So tell me about yourself, Anthony. How does an American end up working in the Bahamas?"
He smiled, flashing his teeth for a moment as he blushed. When she mentioned friends, Anthony thought about Scott. He wasn't here to shout one of his phrases about the three special words regarding a busty model like her. Her question made him stop and think for a moment.
"Well, it's a complicated story. I'm not rich. I liked to play cards, and I got stuck down here during spring break when I was in college. I just never went back home."
She smiled, nodding at him.
"That's funny. I knew I wanted to be a model, but I didn't know how long it would take me. Did you see yourself working at a place like this when you were still at uni?"
He shook his head as she laughed.
"No. Life is strange, I guess you could say. I wasn't thinking about my future at all back then. I just liked to have a good time and play poker."
Time seemed to be passing by. Until now, Anthony had yet to stop and think about how long they had been talking. Everything had slowed down, and he felt more relaxed in her presence. His job was the last thing currently on his mind. So much time had gone by since the last time he shared a night with a lovely woman. As Penny walked across the room, her heels made soft thumping sounds across the new beige carpet. The lower floors still had wooden floors after the suites were upgraded some months back. Her eyes glanced across the kitchen area. A small table with two chairs sat across from a sink and refrigerator. Another doorway led to the bedroom. Penny stepped into the kitchen. Her heels stomped loudly across the tiled floor. Anthony moved behind her as she opened the fridge. She swiped her hand across a plastic water bottle. As it fell to the floor, Anthony spoke.
"I'll get that for you."
Quickly bending over, Anthony grabbed the bottle. Penny stepped behind him as his shirt moved over the back pockets of his pants. He felt something pulling at the back pockets. A faint gasp was heard before he had time to turn around and present her with the dropped bottle.
"My, my..."
Her eyes became larger as she studied the first card. Anthony swallowed his breath at the feeling of his blood pressure rising. The last thing he expected was for her to grab the cards sticking out from his back pocket. His left hand closed the refrigerator as Penny flipped through the cards.
"I see you play more than just the usual card games."
Busted. That was the only word Anthony thought of while watching Penny flip through the cards. Would she believe him if he were honest? What difference did it make? Their short conversation had to come to a halt. She likely viewed him as a pervert working at the hotel. On second thought, there was no point in lying to her if she asked where the cards came from.
"Were you a pickpocket thief before you became a model?"
A smartass question caught her attention. Penny held the cards up to her face, shielding her mouth from his view. She blinked before replying.
"Where did you buy these cards? They're quite... cheeky."
"I didn't buy them."
The sound of her voice and that last word made him blush. Anthony gazed into her eyes as he continued speaking.
"I found them in the bathroom of another room. I thought they were funny, so I decided to keep them for myself."
Penny began giggling as she lowered the cards, revealing her mouth to him. She seemed to believe him, so Anthony carried on.
"What do you think of them? I've been wondering if there are cards pulled from the deck. I don't think this is all of them."
"It looks like a Kama Sutra game for two people. Whoever left the cards behind would need a partner. Someone who is the opposite sex."
Her words intrigued him. If this was her way of flirting, Anthony was ready to give in. Memories of his past romps came back to his mind. She wasn't the first woman gracing the pages of Sports Illustrated to walk into the hotel. He even considered bragging to her about his fun times spent with Kate Upton. Penny handed the cards back over to him and smiled.
"You're a funny guy. I can tell from the look in your eye that you're not lying. Something tells me that if you had a full deck, you would've played the game by now."
"If I knew what the game was, yes."
"Let's say it's a board game. The board would be a bed."
Anthony chuckled.
"I'll agree with you on that. What would you call the dice?"
"Hmmmm, that's a good question. I'm thinking a pair of balls would make a fine substitute."
Exhaling a deep breath, Anthony quietly let out a sigh from his nostrils. Her eyes remained locked on his, teasing him with the smile on her face. She was a strange woman to be flirting with him like this, having only met minutes earlier. He didn't know what to think of her so far. Did he have a chance of bedding her? He wanted to tell himself that the chance was high. On the other hand, Anthony knew a woman like this wasn't an easy lay. He didn't know what to say back to her last words as his eyes drifted below at her heavy cleavage. Penny raised her head, still smiling as she spoke again.
"I guess you need time to let your imagination wander."
Once again he blushed, eyes shifting back to hers. Anthony tried not to smile but flashed his teeth anyway.
"What can I say? Most guys working here occupy themselves with their phones. I like to daydream."
"If that's the case, then I believe I've given you many reasons to daydream the rest of your day."
With that, he knew she was ready for him to say goodbye. Anthony didn't believe this would be the end. Anthony walked away from her. As he approached the door, Penny called out.
"It was nice meeting you, Anthony. I hope to see you again."
He turned his head, offering her a smile.
"I'm sure you will."
******************
7 HOURS LATER
The day passed by in a blur after the meeting. Before meeting Penny, Anthony was just happy to get out of cleaning duties. He fought the temptation to go online and search her photos from his phone. The Sports Illustrated photos were one set he had already viewed before. Penny probably expected him to search her online. That was something he came to expect after his previous affairs with other models. All of this came down to if she truly wanted to see him again. After clocking out of work, Anthony was relieved to get out of his work uniform and take a shower. He kept the sex cards close by, stuffing them in the pocket of his cargo shorts. He put on a green shirt and decided to go on a short trip to the bar. That was always the one place he could find his coworkers after work relaxing along with the guests. Anthony had every intention of ordering a few beers and sitting alone. His plans changed from the moment he entered the room and saw her. Penny sat on a stool at the edge of the bar. Her long blonde hair flowed freely. She noticed Anthony as he stood in the doorway, as if she had been waiting for him to arrive.
"Hello again."
Greeting him with a smile, Penny stood up. She wore a white bustier with gold buttons down the middle. It elevated her cleavage, pushed up and poking forward. The top matched her denim shorts, revealing her strong legs. Her toes were visible in flip flops, leading Anthony to wonder if she spent much of her day walking the beach outside.
"You look like you've been waiting for me. What made you think I'd come to the bar?"
"I asked some of the other employees here. They told me Mr. Anthony always has a drink on week days."
"Once I'm off the clock, I like a cold beer, yeah. Is that all you asked them?"
Shaking her head, she stepped a bit closer to him. Penny then raised her right hand.
"I've been looking for someone to play cards with. I was curious if someone had brought a special set of cheeky cards over to the lost and found department."
Her fingers slipped between her breasts, revealing more cards she hid in her cleavage. Penny slipped them between two fingers, showing the back of the cards matched his deck.
"Look what they brought me."
"Did they tell you where they found those?"
"No. I told them I left something behind."
More cards was a telling sign. Anthony began to think to himself. The set he found in a spare room was left behind by one guest. Maybe these other cards belonged to another person who was playing a game. He reached into his pocket and took out his deck. Penny handed him the cards.
"Here you go. I don't know how many cards you have already, but this should be enough to play a game."
"A game, you say?"
She gazed back at him and licked her lips. Penny slowly nodded before smiling.
"Yes. I've thought long and hard about this throughout the day. There's something about you that gives me a good feeling."
"Well, I'm glad you think so."
"I have this fantasy with strangers. I meet them wherever I go but have never indulged myself with a stranger. You've made a solid first impression. Tonight I'd like to take a chance."
"I guess I should consider myself lucky then."
Penny smiled back at him. Anthony gazed down at the cards she handed him. They were similar with differing sex positions. He wondered if it was this game that made her attracted to him in the first place. He guessed that more than one person had been swapping the cards around with another guest merely days ago. For another employee to deliver them to the lost and found area could only mean that person wasn't amused by their discovery.
"Come on, let's head back to my room."
"After you, Penny."
He teased her with a smile. His assumption proved to be correct that she was waiting for him. Anthony figured that along the way back to her room, he would learn more about her intentions. As long as he was washing away the past months with a good night spent alongside her, he couldn't care less. Together, they left the bar and wandered back to the elevator leading to the suites. Inside, Penny watched him shuffling the cards around within his hands.
"I still don't know how to play a game with these cards."
"We can come up with our own rules. That's more fun than a rule book anyway."
This time she pressed the button inside the elevator to close the doors. Anthony let out an audible sigh before grinning.
"You look excited."
"What can I say? It's been a while since I had anything like a one night stand with a woman."
"Is that what you think this is? A one night stand?"
"If not, then what is it?"
Flashing her teeth, Penny smiled without responding to his question. All they could hear was the sound of the elevator moving to the higher floors. Anthony felt a little annoyed and blurted out what he was currently thinking.
"I'm trying to figure out what your point is in all this. I'm just some guy who works here. What makes you want to take me to bed?"
"I don't. I want to play a game with you. You claim to be good with cards, so we'll see how much you're telling the truth."
"But it's basically sex with a stranger."
Raising an eyebrow, Penny nodded.
"Yes, but I don't see you complaining about that."
The elevator stopped. After the doors slid open, Penny stepped out. She seemed to drop the conversation, but Anthony wanted to have the last word. It didn't cross his mind that he could potentially be blowing his chance with her. He clutched the cards tightly in his right hand, walking alongside her as he spoke.
"It still doesn't make sense to me."
She cracked up giggling in her strong British accent.
"Since you want an explanation, I guess I'll give you one once we're behind closed doors."
Reaching for the doorknob, Penny glanced over her right shoulder. The metal clink was heard as she turned the knob and opened the door. Inside was darkness until she flicked the light switch. Penny turned around, stepping backward a few times as she watched Anthony enter her suite and quietly close the door behind him.
"I've always wanted to enjoy a night with a stranger. Something tells me I can trust you. This is all for fun with no strings attached."
In other words, she didn't like a man to get attached. Anthony knew what she was saying. He had learned from his past experiences with other models. If he were to ever find himself in a relationship, it would never come from women like her. The thrill was worth it. As he stood there gazing back at her, Penny slipped her feet from her flip-flops to stand barefoot on the carpet. Anthony took this as a silent invitation to remove his own shoes.
"I hope this doesn't keep you from work tomorrow."
"Don't worry about that, babe. I can call the day off if you need me to."
"There won't be a need for that. My photographer friend will be visiting me tomorrow afternoon."
Anthony's first thought was the past threesomes he shared with Scott. It was amusing to think of another walking in on them. He stepped closer to Penny, moving in for a kiss. She moved her head, preventing him from touching her lips.
"I didn't bring you here to make love to me. I want to play a game."
"So you aren't gonna kiss a guy during a one night stand?"
"I don't kiss strangers."
Her voice shifted in a way to tease him. Despite not getting the chance to taste her lips, Anthony wasn't offended. He understood the boundaries she was setting between them. His mind wandered back to the game with the cards. He held them up, offering her the deck just to see if she would grab them. Penny didn't raise a hand.
"Are you ready to play with these?"
Nodding her head, Penny gazed into his eyes.
"Every card has a different position. I figured you would want to shuffle the deck since you're the card player."
He grinned back at her.
"I've never shuffled a deck of any kind of cards like this before."
Stepping back, Penny grabbed the front of her bustier with both hands. The top button came undone with a loud ding. Da-da-da-dap, the rest followed with clinking sounds. She dropped it to the floor, exposing her busty breasts before his eyes. Penny held her head high, proudly posing as she flexed her arms behind her head.
"Have you ever seen a chest as busty as this?"
Actually, he had. More than one. Anthony knew better than to mention the other models of his past. Her bust was impressive. Undoubtedly a set of natural tits. The mere sight was enough to grow an erection in his shorts.
"Your nipples look hard."
"Hand me the cards, and I'll let you touch them."
"Sure, but only cause you asked."
Following her instructions, Anthony handed over the cards. Penny gently took them into her left hand. Raising his hands, he pressed his palms against her breasts. Big, soft, and firm. Just the kind of rack he preferred on a model. Her nipples brushed against his palms until he released the subtle grip. He was impressed not only by her boobs but also by her fit and muscular stomach. It was easy for him to imagine her modeling in bikinis. Anthony pinched both of her hardened nipples and witnessed her lower lip fall.
"You have awesome tits."
"Mmmmmmhhhhhhmmmmm, I'm glad you think so. Too bad there aren't any cards for a position to use them."
If that was her way of saying she used her tits for pleasure, Anthony was happy. He squeezed her tits again, rubbing them together for a moment. Penny reached for his shirt with her free hand. He only let go of her tits when she pulled his shirt upward. Up and over his arms, Anthony helped her in tugging it off. He dropped the shirt to the floor, and she offered the cards back to him.
"Here, take them. I'll let you arrange the deck while I take the rest of your clothes off."
A great opportunity was in his hands now, regardless of how they decided to play the game. Anthony believed that he could shuffle the deck into a specific order to give himself an advantage. Since he had gone over a year without sexual pleasure, he wanted all the positions for himself. He folded the cards out between his fingers, using both hands to look at them as Penny's knees touched the floor. The cards prevented him from seeing her face. Only some of her hair was visible. He avoided moving them from his eyes when he felt her pulling at the front of his shorts. After unbuttoning them, she slid the zipper down. Her fingernails were cold when pressing against his skin. Penny pushed his underwear and shorts down to his ankles. Anthony moved his legs, leaving the clothes behind so they wouldn't get in the way for later. As he stood naked, he studied the cards upon feeling her warm fingers wrapping around his cock. Exhaling a deep breath, he grinned to himself, knowing what was about to unfold for him.
Penny twisted her fingers so slowly around his shaft. She dropped the left hand and then used only the right to jerk up and down. With his other hand, Anthony quickly began arranging the cards as he felt her hot breath blowing across his dick. He bit his lower lip before moving the cards away from his face. Her blue eyes glared up at him as she held the dick under her chin. Seeing those eyes made him think about another woman who once clutched his cock as if it were her husband's. He exhaled a deep breath when remembering Kate Upton. The thought went away when Penny parted her lips and slid his shaft into her mouth. She released the grip of her fingers from the base and pressed both hands against his legs. A soft moan was heard from her voice as she pushed his cock further down her throat, sucking slowly and sensually. This beginning gave him an idea of what to expect as the night progressed. Penny seemed to be the kind of woman who took her time and knew how to make a man feel special. Holding the cards in his right hand, he groaned and whispered lowly to her.
"Ohhhhh, yeah..."
She reacted to his voice by pushing his cock all the way down her throat. Anthony was impressed by how easily she deepthroated the length. His stringy pubic hairs rustled against her nose. Penny withdrew his shaft, keeping only the head in her mouth as she sucked him by the inch. Up and down she moved her lips while keeping eye contact. Her fingernails lightly grazed across his skin, trailing down his legs and then back up. The slight scratches weren't enough to distract him from gazing into her eyes. If only she would've allowed him to kiss her. He exhaled a deep breath as Penny closed her eyes and began sucking faster. It was only for a few seconds. Her left hand gently gripped his balls for a subtle squeeze as she moved her lips back to the head. She withdrew his cock from her lips with a loud pop. Wrapping her right hand fingers around his shaft again, Penny resumed stroking it.
"Do you like it?"
Anthony without thinking. Penny ignored his question and pumped her hand faster as she lowered her head. With the help of her left hand, she pressed his balls against her lips before sucking on one. Anthony almost dropped the cards from his hand.
"Yes!"
It was always delightful when a woman gave his sack this kind of loving attention. Penny rolled her tongue around one of his balls, then alternated with the other. Her right hand slid down to the base of his shaft, squeezing it hard. After a few seconds of licking his nuts, she began to stroke his shaft. Up and down, Anthony watched her hand move. He took a deep breath, waiting for her to finish. When she released his balls from her lips, Penny moved her head and gazed into his eyes. Her tongue was the last thing he saw before his cock was between her lips again. 'Mmmmmmmm,' she moaned softly with his cock halfway into her mouth. Anthony reached down with his left hand and fondled her right breast for a few seconds. This made Penny shove his cock down her throat again, utilizing her experienced gag reflexes. Anthony groaned again. He thought about how she could make him cum soon if she so desired. Once again, he was reminded of his old times spent with other models. An idea came to mind.
"Ohhhhh, god. I think I have a pretty good idea how we can play this game now."
Penny stopped sucking and pulled his cock from her mouth to let out a loud breath.
"Ahhhhh, yeah? Have you been thinking about it all this time?"
"Yeah."
"Well then, it would appear that my lips have served as good motivation for you."
He blushed, grinning widely at her. Penny giggled as she saw the look on his face.
"Don't tell me yet. I want to see how far I can blow your mind first."
All at the risk of blowing something else, Anthony quietly thought to himself. He reached for her right tit again with his free hand. Penny took the hint and moved her hand away from his dick. She grabbed her mighty breasts and raised them up. Anthony knew what was coming. There was no point in asking. Penny wanted this as much as he did. As she pulled her breasts apart, she shoved them around his cock. He moaned as she pressed them together, trapping his dick between them. Anthony reacted by instinct and bucked his hips to fuck her tits.
"Yes, go ahead."
Glancing down, Penny watched the tip of his shaft poke up as Anthony completed a hard thrust. He repeated the action four times. A soft moan was heard from her voice before she extracted her tongue to flick the head when it poked up. Her breasts were so soft and firm. The way his slick, wet shaft glided between them was almost enough for Anthony to lose control. Tittyfucking had always been one of his favorite kinks. It was even better with a girl like her, stacked and busty.
"I love fucking tits. I haven't done this in so damn long."
Penny gazed up at his face and chuckled at his words. Anthony continued to thrust, moving at a slow pace to hold himself back from cumming. He still clutched the cards in his hand. Sweat formed under his fingertips, making them a bit slippery. He didn't care as he continued to pump back and forth. Penny glanced down to watch his cock poke up again. She licked the head like before.
"I could do this all night long."
She ignored his words and opened her mouth. Anthony tried to thrust far enough to slide beyond her lips but failed. He made a few harder thrusts all for Penny to raise her head and prevent his cock from slipping into her mouth. She smirked as a way of teasing him. Anthony groaned as he began to thrust harder and faster.
"You're having fun with my tits."
"Oh yeah! You can say that again!"
Giggling again, Penny kept her head raised. Anthony thrust hard enough to make the tip of his shaft touch her chin. Biting her lower lip, she moaned.
"I hope you're still thinking about our little game while you do this."
Holding back the cum within was a greater concern than the cards. Anthony had as much confidence as arrogance within. He made one final thrust, then used his right hand to pull his cock out from between her tits. She kept them pressed together, elbows flexing out. Both nipples were visible under her fingers. Anthony guided his cock to her left nipple and rubbed it. Penny reached for his cock, prompting him to let go. As her right hand replaced his, Penny used her left forearm to wrap around her tits. Anthony smiled at the 'hand bra' pose. She rubbed his cock against the other nipple and then let go. He sighed in relief, knowing that he could last longer. Penny went easy on him. Had he lost control, he could've easily blown a load from fucking her tits.
"I think I know how we can determine a winner. I've thought long and hard about how we're going to play this game."
As he spoke, Penny wrapped her fingers around his cock and slowly stroked away. Her other hand fell to his balls, cupping them for a few subtle squeezes. Anthony moaned and continued on speaking.
"We take turns drawing cards from the deck. With each position, let's do it for a set time. Whoever cums first is the loser."
"And the winner is the one who holds out long enough before we stop?"
"Yeah. If I make you cum first, then I want to do something."
"Do what?"
Anthony smiled.
"If I win, I want to cum on your face. What would you like your reward to be if you win?"
Her eyebrows raised when he mentioned he wanted to see his cum on her. Anthony watched her lips curve into a playful smile.
"If I win, I would ask you to give me a massage."
How convenient, he thought to himself. Anthony remembered when he once held the job title of masseur. Penny made things easier for him.
"Deal. But if I win, I want to cum all over your pretty face."
"I'll let you. I don't think we need to keep track of time. It would be easier to try a position and see if we like it. The whole reason I chose to do this with you was to experiment a bit."
Penny got up from the floor to face him. Anthony walked over to the small table sitting in front of the couch.
"Do you mind if we use the couch instead of the bed?"
"Do you enjoy having sex on a couch?"
"Yeah."
He stopped himself with a single word reply. He wanted to brag about the girls before her. She wasn't as famous as them, but what the hell did he care? This was one of the few accomplishments he had in life. Few men in this world had bragging rights like him. He licked his lips as he handed her the cards.
"You can start us off. Ladies first."
The cards had been carefully arranged with most positions on top that favored Anthony's choices. He wanted to be in control. Everything depended on if Penny would draw the first card or reshuffle them. Moving to the couch, he sat down in the center and pointed to the small table close by.
"Just set them there on the table."
She leaned forward, properly bending over to show off her booty in the stonewashed 'Daisy Dukes' shorts. Before she drew the card, Penny popped the button loose and dropped them to her ankles. A red thong was tucked between her plump cheeks until she pushed it down. After stepping out of her clothes, she was finally naked and ready to play this lewd game with him. Anthony gazed at the round cheeks, slightly splitting when she spread her legs. He raised his hands and fought the urge to touch. Penny drew the first card and turned to reveal it tucked between her right index and middle fingers.
"Lusty Lap Dance."
Anthony smirked.
"Do you think you can handle that position, Penny?"
Placing the card down on the table, Penny pointed with her other hand at a spot.
"Just so long as you sit up."
It was a risk placing that card at the top of the deck. Anthony believed she would go for it since it had her on top in control. Some of the positions were similar apart from small differences. He leaned up on the couch and then watched as Penny completely turned around. Her pussy was clean without any visible hairs above the pretty pink folds. She reached for his cock with her right hand, holding it upward. Bending her left leg first, then the right one, Penny adjusted herself around him. She properly straddled him and sank his cock into her pussy. Anthony closed his eyes and moaned. So many months had passed since he last became one with a woman. The tightness of her cunt wrapped around his shaft, bringing him to another level of pleasure. He opened his eyes and looked at her tits close to his face. Penny placed her hands on his shoulder.
"Have you ever given a guy a lap dance?"
Shaking her head, Penny moaned.
"No. I'm not imagining myself as a stripper. I'm going to pretend I'm a belly dancer."
Whatever fantasy she had in her head made no difference to Anthony. He sat back and placed his hands on her boobs, squeezing them as Penny began to rock up and down. She went slow, grinding her hips to move his cock inside her.
"You like that?"
Nodding at her, Anthony smiled.
"Yeah. Keep going, babe."
Her fingernails dug into his skin and caused small stinging pains on his shoulders. Anthony ignored it as he shoved his face between her breasts. He heard her moaning as he flubbed his lips and began motorboating her tits. Penny shifted her hands, moving them to her boobs. She pressed them against his face, smothering him as she continued to grind at a slow pace. Anthony believed he could withstand being inside of her long enough not to have an orgasm. He was confident enough to believe that when he drew a card, he could probably end the game on the second round. Right now, his focus was on her tits and them alone. He ran his fingers to her nipples, pinching and pulling at them. Penny gasped, moving slightly faster. Her hands moved back to his shoulders, pressing down until she gripped hard. Anthony's tongue slathered across her left tit until he found the nipple. He bit down on it, gazing up at her gorgeous face as he sucked away.
"Ohhhh, ohhhhhhhh yeah..."
Biting her lower lip, Penny purred soft moans as he continued sucking her nipple. Anthony moved his hands to her hips, encouraging her to move faster. She didn't. Penny maintained the slower pace, trying to grind on him. He didn't think about it at first, but now it seemed apparent that she took the idea of a lap dance seriously. Pulling his mouth from her left nipple, Anthony kissed the right one. He gazed up at her face as he moved both hands to her tits, fondling and squeezing them.
"Are you sure you've never given anyone a lap dance before?"
"Yes! I know for sure that I haven't."
Laughing at her, he flashed his teeth in a smug smile.
"That means I'm the first."
His arrogance made the smile vanish from her face. Anthony hoped that she would want to end the position soon and allow him to draw a card. The longer he was inside of her, the more he felt the urge to take control and fuck her into an unforgettable orgasm. This was a game he was determined to win after arranging the cards into his preferred order. Penny continued to grind as she pressed her hands against his chest. Anthony responded to her touch with a hard squeeze on her tits.
"Ohhhhhhh, yes!"
"I think it's my turn to draw a card now."
"Ohhhhhh, yeah... I'll let you have that."
"Thank you, babe."
A sarcastic reply flowed from his mouth. Penny got up, sliding his cock out of her pussy. She exhaled a few deep breaths as Anthony leaned forward and pulled a card off the front deck. He had forgotten what the second card was until he turned it for them to see.
"The Figurehead."
He laughed. The name reminded him of a book he found to be excessively boring and dull. Penny took the card from him and raised an eyebrow.
"Oh, this is an interesting technique. We both need to be on our knees to make this position work."
His first thought was to go into the bedroom. Anthony forgot and dropped that idea when he saw Penny fall to her knees. The drawing on the card showed a man behind a woman, both on their knees. The woman had her arms behind her, holding the man in place. His hands were on her breasts, which was the one place of her body Anthony wanted to touch again.
"You're not scared of getting any carpet burns before your photoshoot?"
Her golden hair flipped around as she glanced at him across her right shoulder.
"Not at all. I'm expecting you to go slow as I did for you."
A fair point, Anthony considered. He didn't like to thrust fast when his knees were touching the floor anyway. Once he got down on the floor, Anthony moved behind her. His stomach brushed against her back. Penny raised her arms and slid them behind her head to pull him closer.
"Go ahead. Get back inside me."
"Are you going to ask to get fucked?"
Penny chuckled under her breath.
"In this position? No. Later tonight? Yes."
"Fair enough then."
Some dirty talk would've went a distance at motivating Anthony. Better still, he gripped his cock and guided it between her thighs. Penny raised her head and let out a sharp moan as he slipped back inside her delightful entrance. He grabbed her breasts again, squeezing them hard as he began to slowly thrust into her.
"Ohhhhhh, yeah."
What Anthony couldn't see was the expression on her face. Was she relieved that he was inside her again? Were her eyes shut? Pointless questions, but he wished he knew the answers. Her fingers laced together around the back of his neck. He tried to lean forward and kiss her neck but was unable to from her arms in place. Penny moaned, calling out to him.
"Yes, yes... Ohhhhhhh, yes."
The sound of her voice and that amazing accent only made Anthony want to raise the pitch louder. He thrust harder while squeezing her tits. Penny arched her head upward as her nails dug into his skin and scratched the back of his neck.
"Ohhhhhhhh!!"
Another hard thrust followed as Anthony's cock pumped faster. He no longer cared about keeping the same slow pace she spoke of. Adjusting his hands, he spread his fingers out to pinch her nipples between them. Penny gasped, moaning again.
"Yes! Ohhhhhh, yes!!"
"Moan for me, baby. I want you to moan louder for me. Come on, louder!"
In a better position, Anthony could've spanked her after demanding to hear her voice. The only way he could get his point across was to thrust even faster. His grip on Penny's tits loosened, almost causing them to jiggle out of his grasp.
"YESSSSSSSS!!"
With that scream, she removed her hands from around his head. Penny arched herself forward, planting both hands onto the floor and leaning forward in a defeated pose. Anthony smirked. His hands were no longer holding her tits, and now he had the chance to smack her ass with his right palm.
"Are you ready to draw a card?"
Her head hung low, and Penny needed a moment to catch her breath. Anthony knew if he wanted to, he could've fucked her into a climax right then and there. She was close, while he felt that he could withstand another few rounds. He carefully and slowly extracted his cock from her pussy. Penny whimpered a low sigh before speaking.
"Yes, I'll draw the next one. Oh my god, you almost made me cum."
"I was close too."
A spoken lie that she seemingly bought. Anthony figured that Penny believed him from the way she looked into his eyes. He went a step further with an exaggerated sigh as he rested on his knees. The table was close by his right arm, with the deck in reaching distance. Penny turned around and sat on her knees as she grabbed the deck of cards. Instead of pulling the top card, she reached beyond and grabbed what was the third card underneath. Holding it between two fingers, she let out a sigh before revealing it to him.
"This card is just a fancy version of doggy style."
On the card was a drawing of a man and woman engaging in a position called 'Deep Penetration.' It was a similar position that required them to be on their knees. The man was behind the woman, thrusting into her.
"Draw another one."
After placing the card on the table, Penny then picked the one that was on the top. It would've been the true third card. She smiled at the position.
"Well, this one should make things interesting."
She turned the card around for him to see. Anthony leaned forward to look at the contents printed across the white canvas. 'Push-Up King' made him laugh. It required the woman to lie on her back and the man to do push-ups for proper thrusts inside her. He smiled and laughed.
"The funny thing is, I haven't done push-ups in years."
Penny giggled at him.
"I believe you. I could tell from the moment we met, you weren't the kind of man who hangs out at a gym."
Her remark made him blush. Anthony thought this position would be ideal to make her cum. Penny had other ideas, judging by the playful expression on her face.
"I want to count every push-up that you do."
"Oh yeah? What if I make you cum while doing this? Is there a certain number you want me to reach?"
Penny stopped and thought to herself for a moment.
"I think you've just given me a much better idea."
"I did? Tell me, babe."
Smiling at him, Penny continued.
"If you can make me cum in less than fifteen push-ups, then I will give you another titwank. How's that for a challenge?"
"You have a deal. Fifteen, you say? Sounds like we're going boxing rounds."
"Is that how many rounds the boys go in a match?"
"I don't know. I'm just taking a guess. But consider your challenge accepted. I'd love to shove my cock between those tits again before I blast your face in cum."
Now he had another reason to find this position favorable. Her eyebrows raised, and she smirked at his dirty words. Penny moved again to create the position on the floor. Resting on her back, she slightly spread her legs. Anthony crawled towards her. His eyes scanned her legs, tracing the texture of her skin and the sight of her juicy cunt. Beyond the appeal of her busty tits, Penny had a great body.
"Just remember, you need to put your hands on the floor. I don't want you pushing down on me."
Penny spoke as he leaned over her.
"Don't worry, I wasn't gonna do that."
They exchanged nods as Anthony slowly pressed his chest against hers. The feeling of her nipples poking against him was amazing. He moaned while reaching below and grabbed his cock. Penny slightly moved her legs, pressing her bare feet against the carpet and elevating her knees. After his cock slipped back into her pussy, Anthony had to take a moment to make this position work. He moved his legs together and elevated his body with his toes. His palms pressed into the carpet around her, holding himself up.
"Looks like you're ready now. Go ahead and start. Let's see if you can become a real push-up king for me."
She giggled at the end of her speech. Anthony blushed, grinning to himself as he glanced down at her amazing breasts. Penny noticed his eyes focused on them and moved her arms to the side to press her tits together. Each time he would complete a push-up, one reward would be the satisfying feeling of her nipples brushing against his chest. Anthony began, thrusting into her pussy as he made the first push-up.
"One."
Staying true to her word, Penny began counting. He thrust again as he completed another fast push-up.
"Ohhhh, two! I felt that!"
Again, he moved while thrusting forward. Penny moaned, biting her lower lip before blurting out the count.
"Three."
Following with another hard thrust, Anthony grunted and sighed. He had begun this act with the wrong attitude, thinking he could do push-ups at a quick speed. Maybe that would've been possible if he did them more commonly. This was the first time he did push-ups in many years. His eyes focused on her tits again as he held himself up and then made another hard thrust.
"Ohhhhh! That's the fourth pelvis thrust."
"And the fourth push-up, don't forget that!"
Something about hearing her utter the words 'pelvis thrust' made him laugh. Penny just smiled as Anthony continued.
"Five."
Leaning forward, a new idea came to his mind. Anthony saw a way that he could thrust into her while doing slower push-ups. He gritted his teeth, grunting again as he bucked his hips. Penny's eyes enlarged to a surprised look.
"Ohhhhhh!"
"You like that? I want to hear you say 'fuck me,' even if it's just one time. Say it, please."
"Fuck me with your push-ups! Come on! You can do it!"
His wish was granted in the most hilarious way. Anthony couldn't stop himself from laughing. Like so many times before, Penny's humor made him blush. He was grinning wide as he completed another push-up and stopped.
"Six! Ohhhh!!"
Still lying atop her, Anthony completed several thrusts into her pussy. Penny bit her lower lip, purring softly. He knew from the look on her face that he would make her cum in this position. No more cards would be drawn. It was going to end right here, regardless if her count hit the number fifteen. Anthony moved up and completed yet another push-up with a hard thrust.
"Seven!"
One more passed the halfway mark.
"Eight!"
He stopped, resting on her chest again. The longer he gazed into her eyes, Anthony wished she would kiss him. That was all he thought about while pounding his cock into her pussy.
"Ohhhh! Ohhhh, god!"
Pumping faster and harder, he completely forgot about the push-ups and lost his train of thought.
"Fuck me! Fuck me!!"
Penny had also forgotten about the game by blurting out those words. Anthony still found a reason to raise his body and complete the ninth push-up between multiple thrusts inside her. As her tits shoved against his chest. He lost all control, bucking his hips wildly. Penny's eyes shut as she screamed.
"FUCK ME!! OHHHHHHHH, YES!! YESSSSSSSS!!"
Pump after pump followed her screams. Anthony knew she was close but couldn't guess how much longer she could withstand his thrusts. Her eyes opened wide, and she gasped. That was the moment he knew she had reached the brink. With another thrust, Anthony felt her inner walls tightening around his dick.
"OHHHHHHH!! GOD!! YESSSSSSSSS!!"
To hold himself back, Anthony quickly moved off her and pulled his cock out of her pussy. He raised himself on his knees as Penny panted and tried to catch her breath.
"My god! I knew you wouldn't be able to do ten push-ups. I just knew it from the look on your face. I didn't expect you to make me cum so hard though."
As she spoke, Anthony had already moved into the next position. He bent his knees after finding a place to sit on her stomach. Penny's hands were still pressing her tits together. Anthony didn't wait to shove his cock right between her tits. It disappeared from his sight. Penny smiled.
"You've earned this titwank."
What he didn't expect was for her to begin pumping her tits up and down. Penny was doing the work for him. All he had to do was sit there and watch. She tilted her head forward, watching the tip of his shaft poke up as she worked her breasts back and forth.
"You're not pulling out. When it's time, you just have to shoot your best shot if you're still hoping to cum on my face."
Up and down, back and forth, she worked her breasts. Anthony grunted upon realizing that he had lost control here. He may have won the game, but Penny would be the victor of this battle. His cock was already throbbing between her huge boobs as she continued to pump them. He grunted as his face contorted into a conflicted expression. The pleasure was so good, Anthony only wished that he could last longer. Penny was on a mission, determined to make his cock explode. A few more pumps and Anthony belted out the loudest scream of the night. All he could see was the tip of his shaft poking between her tits, aimed directly at her face. Penny's eyes were open, bravely anticipating his explosion.
"FUCK!! OHHHHHH!! FUCK YES!!"
A long string of cum fired out, landing on the left side of her face. Penny's eyes remained open as another spurt of cum splattered on her chin. Anthony grunted, crying out as his shaft leaked more cum. Thick wads of cum fell on her neck, highlighting the muscles. Only the first and second spurts came out with enough force to reach her face. Penny raised her head upon realizing the rest of his cum was spewing out along her neck. It created a river of semen flowing across her skin. Anthony sighed, satisfied that at least some of his load decorated her face. The rest formed a proper pearl necklace. Penny pulled her tits apart to allow him to see his shaft resting between them.
"Wow. Your tits are fucking unreal."
"I know."
Penny smiled at him as she raised her right hand to swipe some of the cum from her chin. Anthony just sat there, gazing into her eyes as she licked the tip of her finger. He was speechless. His first thought was to thank her for such a wild night, but he was unsure of how to say it. Climbing off her, he stood up and offered Penny a hand. Only then did he notice the epic mess around her neck. Streams of cum were now dripping onto her breasts.
"I need to jump in the shower. Don't you have work tomorrow?"
"Yeah."
"I have a busy day tomorrow myself. I appreciate the fun we've had, Anthony."
"Think of me when you're visiting your friend."
She laughed, flashing her perfect smile.
"I'll try not to! That might just distract me."
THE END