A Play-Boy's Bet

A Play-Boy's Bet

last updateLast Updated : 2026-07-02
By:  TabbyUpdated just now
Language: English
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Jack Charles: I was alone, but I was happy at least. My life revolved around my family and my studies, and I didn't need anyone else in my life. But Daniel... he barged into my life and turned it upside down. He showed me what love was, what happiness was and just when I threw myself deep into the abyss, he showed me his true colors. For him, I was just a project. A bet to win my heart and then leave me alone forever. I gave him everything. I gave him my money, my lavish lifestyle. I gave him my first time too because I thought it was all love.... Now, I hate him to the core, and I have decided to move on with my life and it's better that I didn't tell him the biggest secret of my life, because I am sure I would have made a fool out of myself. It's an angst, Friend to Enemies to Lovers book with a happy ending. No third act cheating but trigger warning of abuse, mention of rape and physical Assault. It is M-preg book so proceed accordingly. Tabby

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Chapter 1

Chapter 1. The Bet

Chapter 1. the Bet

"I am getting bored now guys". Daniel put his beer back on the table heaving a sigh.

"Oh hooooo. The prince is bored". Wyatt said in a teasing tone.

"May we know how the reason my prince"? Mason gulped his beer this time.

"Duh. What’s with you guys"? Daniel laughed at the antics of his friends. He was aimlessly twirling the bottle on the table. They were currently sitting at Parker's place. They were four boys Wyatt, Parker, Mason and Grayson. They were the four minions of Daniel Stephen.

They were friends since the diaper days. They were coming from middle and upper middle families, in a renowned University majoring in Sports.

Daniel came from a mediocre background. His father died when he was 12 years old.  And now he had a mother and an elder sister. She was a gold medalist and full scholarship holder at the age of 18 to start her university life. But with the death of their father, she had to say good bye to her dreams and started working in a cafe to earn for her family.

While Daniel, on the other hand was an average student. He was a rotten spoiled child. He was pampered a lot by his mother and sister who strived every bite to feed him with everything he likes. His sister made sure to give him every luxury in the world that she could manage.

When he had to start his university, she went as far as begging the Principle to transfer her scholarship for her brother. It was against the rules, but keeping in mind her achievements for the university, a straight ‘A’ student. They somehow agreed to grant the admission to Daniel at scholarship.

Daniel was a second year student. His home was nearby so he was good to stay with his mom and sister. But what they didn’t know was that he was a playboy, who had almost tasted every girl and every boy in the neighborhood.

He believed in one night stands only. Totally fuck and leave with no strings attached. He never turned back after leaving the rooms. Yet the girls would keep drooling and begging him for another night of pleasure.

And now, he was bored because he had tasted all flowers in the garden and no one attracted him anymore.

"Uhmm Daniel". They all were in thoughts when Daniel heard a rather hesitant mentioning if his name from Wyatt.

"Hmmmm"?

"Have you heard about umm Jack Charles, he is doing a PHD in Business Management". Wyatt was spinning the bottle lightly between his finger and thumb. Daniel opened his eyes to glance his friends. They all had a certain glint in their eyes.

"What’s with the nerd"? He sat up straight with the couch, surely he had heard about him.

"Well...  He is 25. He comes from an exclusive background. He owns a lush apartment in the heart of the city. Single... And..." This time Parker stopped for   a dramatically effect. Daniel got irritated.

"And what..."?

"Virgin...." He said with a wink. Daniel saw him with eyes wide. He licked his dry lips in anticipation. His friends could see his eyes glittering with stars. 

"But... What does it has to do with me"? Daniel couldn’t understand why his friends were telling him about that Jack Charles…

"How about.... Befriend him. Indulge him to be your boyfriend. Stay with him for three months. And... Top him. You have to make sure to shoot the videos as evident. And then after three months you have to break up with him". Wyatt outlined the whole plan swirling his bottle.

"And what would I get out of this? Just a virgin ass to fuck? I can get that without being attached to someone for 3 months". Daniel scoffed.

"How about 200,000 dollars in cash". Mason said gulping his beer.

"The fuckkkkk you said". Daniel spurted the beer in his mouth.

"3 months. Agree him to be your boyfriend. Fucking with no strings attached and you get 200,000 dollars. Not to mention he is hot as fuck and a virgin too". Parker added.

Daniel stood up from the floor, wiping his hands from his jeans. He picked up his wallet and mobile phone with his car keys.

"Mark the date guys. 3 months start from tomorrow". He said over his shoulder and smirked before leaving the door.

What Daniel wanted, Daniel gets.

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

"Good Day, sir ". Jack was startled when a boy greeted him. He was sitting in the cafe of his faculty working on his research, when a boy approached him with a warm smile.

"A good day to you too". He replied politely.

"If you don’t mind can I sit with you "? He asked again. Jack nodded and he took his seat on the other side of the table.

"I am Daniel. Daniel Stephen. I am from Sports Major 2nd year". He introduced himself. He was cute with chubby cheeks. He was a few centimeters taller than him, but leaner than him. He had golden skin, a bit tan than his pale white. And his eyes… Warm chocolate guarded by thick eye brows. He was handsomely beautiful.

"I am Jack Charles. I am doing my PHD in Business Management final semester". Jack leaned back in his chair shutting down his laptop with the research papers.

"Oh wow. You are too young to be a doctor". Daniel praised him with his big innocent eyes and this time Jack chuckled.

"So Daniel, what brings you here"? He asked. "We have the best Americano. Do you want to have some"? Jack asked again and Daniel was quick to nod excitedly like a little kid.

Jack went to order Americano with two slices of Blueberry Cheese Cake.

"Wow, Sir. How do you know I love Blueberry Cheese cake"? Daniel was pleasantly surprised.

"First of all, don’t call me sir, you can call me Jack. Secondly, I know this because, you are extra cheesy". Jack said teasing him and Daniel glared at him playfully.

"Actually. I came here to see a professor, and was just about to grab something from the food court when I saw a heavenly beautiful man, sitting along. He was working on his laptop with so much concentration and attention that I felt envy of this laptop. So..."

"So you decided to barge in". Jack completed his sentence laughing out loud.

"And to befriend him". This time Daniel was serious. Jack turned serious too.

"I don’t have friends Daniel, because I don’t have time for them. I prefer to stay alone". He replied sipping his coffee.

"That’s why I want to be your friend. See. I don’t have any friend either. People think I am a headache. So they don’t prefer my company. I am not imposing myself. I will never disturb you. But I want to have the satisfaction that I have a person I can call my friend". Daniel said with a rather sad smile and Jack didn’t know why he didn’t like it at all.

"Okay okay. No need to be sad. Let’s be friends". Jack instantly stretched his hand for a friendly handshake and smiled as he saw the same shine in Daniel's eyes.

"Ohh thank you. Thank you so much". Daniel almost jumped over the table to shake his hand and hug him tight. He was shaking Jack in excitement. Jack was flustered and blushing hard. It was the first time someone hugged him so happily. 

Daniel pulled off after few seconds and laughed looking at the pink on Jack's cheeks.

"Oh my god, you are sooo cute blushing like that. Wait wait. Don’t tell me. Didn’t anyone hug you ever"? He asked as in a realization hit him hard. And his doubt was confirmed as soon as he saw Jack getting more blushed.

"Oh my goddd". He pulled Jack again in his arms laughing out loud. Jack was blushing but yes he was happy. He was his first ever friend.

They spent good time together sitting in the ground, enjoying each other's company. Talking about their likes dislikes. And Jack realized they had lots of things in common. They loved to play games.

Daniel fished out his phone to track Jack's id and added him in his group. They didnt realize it was already evening. Jack invited him for dinner. Daniel was reluctant a bit but he accepted the offer when Jack insisted.

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

They were getting along good. Sometimes Jack would visit Daniel in his faculty and sometimes Daniel would come with a lame excuse to taste the delicious cheese cakes. 

It was the weekend. Jack had no particular program instead of staying in his apartment. He had his schedule of doing weekly cleaning and laundry. He was in deep his thoughts when Daniel slumped down in front of him. He was just free from his football practice.

"Tired"? Jack offered him cold water bottle that he chugged down.

"Jack, what is your program for weekend"? Daniel asked as his breath calmed down.

"Nothing much. I am going home".

"Going home? Dont you live in the apartment"? Daniel was surprised.

"I do. I live in my apartment on weekdays. But on weekends I go back home". He replied with an easy smile.

"Who is in your family "? Daniel questioned. Jack fell silent for a while. It was long that he never spoke about his family.

"Uhmmm well. I have Mom Dad, my sister in law and twin siblings, a brother and a sister". He said in a low tone.

"Your sister in law"? Daniel couldn’t get the situation. Jack sighed a heavy breath.

"Actually, my elder brother, he was the CEO in dad's office. One day we were at home after dinner, some people barged into our home, captivating everyone.

Only then I came to know that he was being black mailed. He was being blackmailed to handover our business secrets by our rivals that he refused to agree.

I... I still remember they shot my brother and my Dad in front of our eyes. Emily, my sister in law, was pregnant and she went hysterical. My 5 year old siblings, they were frightened to core. I was trying hard to hide them so that they couldn’t see it all. But...

My mom, she had faced the most difficult phase, till now. She was diagnosed with a syndrome where an elder slips into his or her childhood due to the immense shock on brain.

It was a hell difficult time. My sis in law had to take care of my mom and my brother and sister and her pregnancy. While I had to work hard to take over my dad's company.

So now I am working for my degree and then I will take over my business". Jack told him about his family in shaky breaths. It was still hard for him to recall the accident, no matter how much time had passed.

"I am so sorry ". Daniel held his hand and Jack smiled wiping his tears.

"It’s okay. So what about your plans"? Jack turned to Daniel.

"Nothing much. I have only Mom and sister, and currently they are at our uncle's place. So I will be alone at home". Daniel told, playing with the laces of his joggers. Jack thought for a while before fishing out his phone.

"Hello Em! How are you? How’s mom? Em, I wanted to ask if there is nothing urgent can I stay this weekend at my apartment. I have some work to do"? Jack said and hung up the call after a while.

"Daniel. Do you want to come to my apartment"? Jack offered. Daniel was surprised. But he nodded his head quickly. He couldn’t lose the chance. Right?

"I would love to go to your apartment. But I don’t have change of clothes so I have to go home and get a bag for the stay. How about we meet at the cafe at 5"? Daniel suggested and Jack agreed. Daniel almost ran to the parking to get his car to go home.

"Sisssss. Mommm". He entered his home screaming for his mom and sister.

"What happened, Daniel? Why are you shouting"?

"Mom I am going to my friend’s place for group study. My other friends will be there too. We will stay the night or maybe the weekend. I will let you know okay"? Daniel ran upstairs to his bedroom to take a quick bath and pack his bag. It was no longer when he came downstairs to walk up to the cafe just at the corner of the street.

"Okay Daniel. Study hard okay? Keep some money okay"? His mom handed him some money as he kissed her cheeks before hugging his sister to go out. 

"Guys, I am leaving for Jack's apartment. I will keep you updated. If mom calls tell them we will stay the weekend at Parker okay"? He sent a message in his group chat and instantly got thumbs up.

"Let’s go Mr. Charles. Let’s see how long can you resist me". He smirked pulling off his glasses and smiled sweetly as he saw Jack sitting inside the cafe waiting for him.

----

Tabby

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