Big Booty Bitches Ch. 09

Story Info
Britney Spears strips for Tony Jr and his gay lover.
11.2k words
4.67
21k
71

Part 9 of the 39 part series

Updated 09/11/2023
Created 07/02/2016
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Author's Note: This story is completely fictional and did not happen. All characters and names are fictional and were made up.

******************

10 YEARS AGO

Miami, 2006

Loud moans could be heard echoing from within the cabins of a yacht. The yacht by the name of 'Love Boat' had quite an experience going down below in the master bedroom cabin. A dream come true for two lucky men as both of them groaned at the feeling of pleasure they were receiving. A woman giggled loudly in her thick southern accent before speaking.

"Yeah, you both like that huh!? Gonna cum all over this pretty fuckin' face!?"

"Ohhhhh yeah, you're gonna get it!"

The voice was coming from Steven Diaz as he looked down at the face of Britney Spears. He stood on the left side of the room while Tony was on the right. Both brothers had indulged in the experience of a lifetime to fuck one of the most beautiful women in the world. This was something that so many men dreamed of having and here she was taking turns sucking their cocks. Sweat dripped from her forehead as her black eyeliner and makeup had smeared around her left eye. Cum drained from both her pussy and ass onto the floor. The two men had been fucking her for hours, their cocks explored all her holes multiple times. Now, everything was coming to an end as Britney stroked their cocks as fast as she could, begging for them to cum all over her face. She turned to her left and took Tony's cock back into her mouth. The man moaned out loudly.

"Yes, suck it one last time Britney!"

While her mouth slobbered all over Tony's shaft, her free hand was jerking Steven's cock with a tight grip. Both men were moaning. Britney bobbed her head up and down on the older brother's cock before coming off with a loud pop noise. Saliva dripped from her lower lip down to her chin. Steven put his hand on the back of her head in her blonde hair and shoved her towards his cock. Britney quickly wrapped her lips around it while her hand found Tony's cock across from her. She pumped her hand up and down on Tony's shaft while Steven thrust his hips while holding her head in place for him to fuck her mouth one last time. She gagged and created a number of loud slobbering sounds over his cock.

"GWAH-GWAK-GWAH-GAK-KWAH-KAH"

Steven pushed her head all the way down until he head the head of his long dick slam to the back of her throat. Holding her head there for a minute until he heard her choke and seen her eyes begin to water up, he let go of her. A long string of saliva dripped from her mouth back to his cock. Britney caught her breath and wrapped her hand back around his slobber coated shaft and continued to stroke it just as she was doing his brother's cock. She held her face up and looked at both of them in the eyes; Steven first and then Tony to the right.

"I'm ready, cum all over me! Cum on my face!"

"Ohhhhh, you're in for quite the splash."

"Here it is, baby! FUCK!"

It was Tony who spoke first but Steven beat him with the first string of cum that flew over Britney's face. She closed her eyes right in time for a thick string of semen to drench her right cheek and slide down. Tony grunted when his cock exploded and shot a wad over her left cheek. Both of them sent the next wave flying over her at the same time; Tony's cock drenched her forehead in a thick wad while Steven's cum hit her right eye and dripped down her nose. Britney kept her mouth opened and just moaned at the feeling of their hot loads striking her face. A wad struck her right forehead and dripped into her hair, and then from the left her forehead was glazed in another thick wad. She tried to open her eyes but quickly shut them again when she felt a thick wad fly into her left eye. The last spurt of cum from Tony's cock flew over left cheek while Steven's last drops shot up her forehead again.

Steven reached down and grabbed her hair from behind to hold her face up as he smiled admiring the view. She was a complete mess, the two brothers had emptied their balls all over her face and now it was almost as if they were starstruck. Steven couldn't believe this was Britney Spears of all women sitting on her knees, caked in cum. She opened her eyes, slowly blinking with drops of cum glimmering in her eye brows. Looking up at both men as she took a deep breath, Tony turned to look at his brother and grinned. Steven was too fixated looking down at Britney's cum covered face to see his brother starring at him. Tony spoke up.

"We just fucked Britney Spears, hermano."

She laughed, opening her eyes to look at them and then smiled big with her signature smile and those pearly white teeth. She replied to those words calling her name.

"Yes, you sure did! That was a lot of fun!"

Tony looked over at his brother again who then turned to him and held his hand up for a high-five. The woman heard their hands clap loudly against one another. A dream had come true and this event would serve as only a prelude of things to come for Britney in southern Florida. She was a fresh newly made MILF after giving birth and was soon to be divorced and would go wild within months into the next year. Her friendship to the Diaz family all began with a famous woman named Paris introducing her to Tony a few weeks prior to this day.

******************

The clock ticked on the wall, counting the seconds of the passing hour. Tony stood in his office, looking over the picture frames he had hung on the wall of his family. Some were old, some were of recent years. There was an empty frame waiting for his son's birthday that was today, the big number of 21. Little Tony Jr was no longer a child, reaching the age of 21 made him a man. Tonight was going to be his birthday party celebration at Disco Fever. It only seemed fair that Tony gave his own son a party, when Steve had already given a party to Jacob months earlier.

It almost saddened the old man to look back at the photos and see how time had passed by. It seemed like only yesterday his little boy was going through grade school and now today he was legally an adult. It would only be a matter of time that he introduced him to the business and began to mold him the same way Tony's own father worked him and Steven into the club life. The door to his office swung open and he figured that had to be Maria, turning around he was greeted to the smiling face of his brother Steven standing before him.

"Hey man, you busy?"

"No, just making space on the wall for the photograph tonight."

Steven smirked, looking over the wall before nodding to Tony and speaking again.

"Guess who I just heard is in town on vacation."

"Who?"

With a smile, Steven answered.

"Britney Spears, man...that's who."

Tony thought for a minute before slowly smiling and then laughing softly.

"Oh yeah, how could we ever forget about the time with her?"

The brothers laughed together before Steven responded.

"I know what you mean, man! Whenever I think about her, you know what goes through my mind. We got to fuck her back when she was on top of the world. I'll always be proud of that one."

"I sure felt like I was on top of the world that day."

"Me too! Maybe you should call her up to come party with us tonight. It's been what, 10 years now?"

Tony sighed as he thought about Steven's words and nodded.

"Yeah, it was 10 years ago...Funny how time just goes on by like that, I don't know if she's still the party animal she was back then. I see her on TV and stuff, she looks hotter than ever from what I have seen lately. I'll keep it in mind, but I don't know if I should bother her."

"Whatever you think man, I just thought I'd let you know. I'll be around tonight for Tony Jr's party, but I gotta run some errands with Ramón for now. I'll see you later."

"Okay Steven, you take care!"

He watched Steven walk out of the door before sighing to himself. Britney was back in town, that was kinda funny. Forever would they have the memory of that epic day on his yacht with her. It was just months before the year of 2007 when she had her infamous wild streak. That year began with a short lived yet prolific relationship she had with their younger cousin Ramón. Tony heard many stories of their time in the clubs and wild life even though it didn't last for long. For him and Steven, they always had the memories of the past took back upon.

The funniest part about Britney Spears and her old times with the Diaz family was that Tony's own son, had the biggest crush on the pop princess in his youth. He laughed to himself as he thought back to the times when he went through Tony Jr's room and found the stash of pictures he had saved from her. Tony Jr had quite the shrine going for Britney in his closet, collecting various photo shoot prints and all her albums. Tony used to tease his son about the crush he had on Britney, all to see that little face go red and blush. Suddenly, he got the idea that perhaps she would be the greatest birthday present he could offer to him. To become a man at the age of 21, was there any other woman in the world that could make him into one besides Britney?

It was a long shot, but Tony was destined now to attempt this dream to come true for his son. To deliver Britney to him as a birthday present would make him proud as a father and would be a good way to welcome his foot through the door of the club life. This lifestyle would eventually be passed onto him as he was the future of the family. Tony walked over to his desk and immediately picked up the phone to dial in his assistant. Maria would know how to help him track down Britney, his guess was that she probably would be in Miami Beach enjoying her little vacation on the beach.

******************

2 HOURS LATER

The sound of shoes beating into the sand were the only thing Tony could hear outside of the waves crashing up against the shore. He walked slowly along the beach, wearing a black shirt and white pants. He would be blinded at the bright sun if it weren't for the sunglasses he wore. True to his trust in Maria, he had tracked Britney down and got in touch with her one of her managers over the phone. She requested to see him in South Beach. Again, true to his original assumption, she was indeed enjoying time at the beach here in the city.

It had been several years since he last seen Britney. In fact, Tony was a bit nervous about this meeting. He knew the request he would have for would possibly be a long shot, but he wasn't going to go without trying his best. He was approved by her, as spoken from her manager's word over the phone to see her. Still waking the beach, he turned to look as he seen a clear area with no usual tourists. There was only one body in the water and it appeared to be a woman walking up to the shore with a wave of water pushing beside her. As the body came closer, Tony stood as he looked it over. Taking his glasses off, there was no mistaking this person.

There she was in all of her glory. Britney had her golden hair tied up in a ponytail behind her with a pair of sunglasses covering her eyes. Her amazing body looked fantastic, still having a cute little belly button ring piercing. She wore a two piece white bikini with some pattern over the white fabric. Her huge tits still looked terrific and that entire body was a blast. Tony stood there starring at her beauty as she walked out of the water and he seen her bare feet sink into the wet sand. Raising her sunglasses above her hair, Britney smiled at him and waved her hand.

"Hey Tony!"

"Britney, how the hell are ya!?"

"I'm wonderful hun, you look different from the last time I seen you..."

He sighed before responding.

"Yeah, let me guess? My hair makes me look too old?"

"No! Don't say that, I like it! You got that salt and pepper look goin' for you!"

Laughing at her, he shook his head.

"Yeah, thanks babydoll...appreciate it."

"So Tony, I know you didn't come to me just to chit chat. My manager said you wanted to speak to me about something urgent. So, what is it?"

They both stood in the sand together as the water continuing washing on up behind them. Tony looked over at the water before swallowing down a gulp. This was a tough thing to ask her, but he didn't come all this way out to waste her time. They were alone on the beach with no one to overhear their words. Finally, he spoke the words to her.

"I don't know how to ask you this, but tonight is my son's birthday. Tony Jr turns 21 tonight and you are his favorite person ever. You are his idol, he's worshiped you for so many years. To him, you are his goddess. He's had the biggest crush on you since he was young."

Britney smiled hearing his words.

"Awww, how cute! Do you want me to meet your son?"

"Not just meet him...I was wondering if you would...make his dream come true tonight. Take him and fuck his brains out like you did me and my brother 10 years ago."

With the heavy offer to her, Britney looked at him and then thought to herself. Was he serious? She had not seen him in years and he came all the way out here to ask for this? She spoke up.

"So let me get this straight, you want me to fuck your son for his birthday. Is that it?"

Tony nodded and then Britney bust out laughing. She spoke again.

"God, you're crazy! Like, oh my god! I can't believe you!"

"Come on, Britney! I'm serious! What do I gotta do to get you on board? His birthday is tonight, I'll do anything for you to surprise him!"

Thinking about it, Britney smirked at him and then finally responded with a nod.

"Fine, I'll do this for you...but only under one circumstance, it stays a low key secret. If I do this for you, you're gonna owe me somethin' in return."

Tony nodded.

"You have my word on that, what do you want from me to pay you back?"

"It depends, we'll see next time I'm in Miami. I will be sure to call when I'm back in town again, so you can pay me back with some more fun."

"Well, that can be arranged rather easily..."

"What time is the party, Tony? Do I have to be there?"

He shook his head at her second question.

"No, you are the after-party baby. You get all dressed up with a good outfit, call me. I have a limo ride set up to bring my boy back to his penthouse apartment. You can be in the car waiting."

"Okay, that works. All my good dancing outfits are back in Vegas, I'll have to go buy some new slutty clothes real soon to get ready."

Tony smirked hearing those words 'slutty clothes' from her lips.

"I'll owe you big for this one, he doesn't know I planned any of this. It's going to be a huge surprise for him."

Britney nodded.

"Alright, that's fine. Let me go get the proper clothes, and put my own kids to sleep tonight and then you call me whenever and I'll be ready."

"It's a plan, thanks baby!"

Leaning over, Tony placed a kiss over her cheek and she smirked at him. The man began to walk off when she waved at him and blew a kiss. While Britney may have changed a lot over the years to straighten her life out, she was still the naughty princess that Tony remembered. The memories would last forever and now this would make the perfect birthday present to his son turning 21. The night was several hours away but he already was thinking about what Britney said of him owing her. If the possibility was on the table for her to return for more fun, it was something that would not be passed up.

******************

6 HOURS LATER

"Happy birthday, to you! Happy birthday to Tony Jr, happy birthday to you!"

"Blow out your candles!"

"Yeah, blow them out!"

A young man sat at a table as he overlooked a large round cake with 21 candles on it. His name was made in the icing in a bright blue color while the cake itself was made in pink. He leaned over and blew out the candles as family and friends clapped their hands. Tony looked over at his son with such pride, as he clapped his hands. The younger Tony looked up and smiled big as a camera moved his way to snap some photos. It was then, his father walked around to lean over and smile and make sure he was in the photos with him.

Tony Jr had lived a quiet life so far. Not one that enjoyed the wild lifestyle of an athlete like his cousin Jacob. His privacy was of far more concern, spending most of his time sitting on the computer and reading gossip on social media. He had dropped out of high school at 17 years old, yet his father didn't care. The real career of his life was already paved before his eyes to go into the business and live off the family's main venture of the clubs. He hoped that he could some how work behind computers if it had to deal with the club business, but that was still a decision some time away. His father was slowly working to mentor him into the role as working the office with management.

Not one for drinks, Tony Jr liked to keep a clean mind at all times. Taking no alcohol, he ate a slice of his beautiful cake in the company of his father and his uncle Steven. While they all called him Jr, he liked to go by the name of 'Antonio' when around his close friends and people in general. It separated him from his father's own name. At 21 years old, he knew that his looks were good enough for most women he had met. With short brown hair and a small mustache, he kept an athletic body with working out every summer. Tonight was the first night he dressed sharp in an expensive suit, a gift from his father. The suit was pinstriped in black with a bright purple shirt underneath.

Without spending all the night at the club, he wanted to leave once it became 11 PM. The older Tony was well aware of this, his son wasn't a party person at all. Everything had been prepared for him to receive the surprise of his life in the back of the limo awaiting him outside. Britney sat patiently in the backseat, while young Tony Jr was escorted out of the back door of the club. When his eyes seen the silver limo, he looked back at his father and sighed.

"Is this really necessary? You didn't have to do this.."

Tony laughed at his son.

"You're going home in style and class tonight, my boy! Something is waiting for you back in that limo."

"Oh yeah, like what?"

"I don't spoil surprises! Go see for yourself, and happy birthday my son!"

"Thanks dad, appreciate it.."

Stepping down from the steps of the back door, he approached the door of the limo. His father stood in the doorway of the exit, watching what was to unfold next. As Tony Jr placed his hand up on the handle to pull the door, it swung open towards him. Tony seen the face of Britney Spears look at his son with eyes of hunger. She gripped his suit and dragged him into the limo before reaching over to shut the door. The limo began to drive off and now the older man stood there laughing hysterically at what he had just witnessed. He clapped his hands together before walking back into the club, Britney lived up to the deal just as he knew she would. From inside the limo, Tony Jr's eyes became huge as he looked over at the woman that had just dragged him inside. Swallowing his breath, he spoke in a frantic tone.

"Holy shit! You're, you're-"

"I'm Britney, yeah it's really me!"

His eyes became huge as he starred into her gorgeous smile. Those pearly white teeth were all too perfect, there was no mistaking this face or that body. Britney wore a big white fur coat, under her stomach he could see a purple thong and then some huge knee high black hooker boots. She looked absolutely amazing, it was as if an old photo had come to life. The outfit reminded him so much of an old photo shoot he had in his collection. She sat on the seat of the limo right next to him. The fur coat covered both her breasts yet created a passage for him to view her strong built stomach. Britney leaned over and placed a kiss on his cheek, watching him blush from her touch.