T. B. Sangster Imagines [REQUESTS CLOSED]

→ Benny Watts- If I Win... ←

Okay. This imagine takes place in 1957. Hence, Y/N and Benny are both teenagers (16 & 17).

All right, enjoy reading!✨

« ~ • ♪ • ~ »

Third person's POV

The school's chess club period was eventually over for today, although a few members, like Benny Watts and his friends, decided to stay and chat. In the process, they set up the chess pieces for a quick game of speed chess.

Although, Benny got quite distracted when he saw Y/N, one of the only female members of their chess club, was getting ready to leave. She fixed her hair up into a neat ponytail before she gathered all her books.

Benny had taken a liking for her ever since she joined the club. He wanted to ask her out on a date.

The problem was, she wasn't the most approachable person out of all of them. The others seemed too intimidated by her for no apparent reason. Not even the other girl member made a move to befriend her. They'd only talk to her when they have a question or if they wanted her to teach them.

Y/N found it better that way. It wasn't really her forte when somebody walks up to her and initiate small talk. She'd prefer it if they had something to talk about besides the weather or the usual short 'Hi' and 'Hello'.

Of course, with Benny being the most confided and persistent young man there is, he decided to ask her. "Hey, L/N!" He called out before she could exit the room.

Y/N stopped on her tracks with an internal groan. The desire of going home was getting the best of her. And Mister Benny Watts just had to get in the way. Again. "I already said no, Watts." She deadpanned as she slowly turned around to fave him, "I am not going to go on a date with you."

It was the fifth time she had rejected him in a week. He didn't stop asking her and she didn't stop refusing him. It was becoming more of a routine that she despised dearly. As much as she returned the feelings slightly, she still preferred herself not having a significant other.

Benny only raised his hands up as if he was surrendering. "Fine." He said, "I've already accepted that."

The corners of her mouth tilted upwards into a sarcastic smile, "Good for you, then." She remarked before turning away.

"But that's not what I called you for."

Once again, Y/N stopped walking. As much as she wanted to ignore him, she didn't want to be rude. So, she lazily turned around again, rubbing her eyes out of irritation, and faced him. "All right, what do you want?" She kept her voice as calm as she could, trying her best not to lash out due to her exhaustion.

"I want you to play speed chess with me." He answered with his cocky smile lingering up his lips.

Now, it was easy for Y/N to refuse when he asks her out, but when it comes to speed chess where her brain was being challenged to think quickly, it was never easy for her to say no, seeing as speed chess was her favourite exhibition when it comes to chess. But of course, she was being asked to play with Benny, the cockiest man she had ever met. Surely, he was on to something.

Then again, she liked a challenge with the said prodigy.

She gave him a skeptical look. "And what's the catch with this?" Y/N asked as she slowly walked over to the table where the chessboard was set up.

Benny's grin widened into a smirk. "I'm glad you asked." Knowing that she was beginning to give into the temptation, he sat down in front of the white pieces, providing a space across him for Y/N to sit. "If I win.." He continued, "you go to the drive-in theatre and watch a film with me tomorrow night at 8:00."

His friends that surrounded the both of them let out low 'ooh's as they assumed Y/N wouldn't be able to beat him. Although Y/N knew that as well, she still couldn't refuse.

There was something about the way he looked at her taunted Y/N. Even though he wasn't saying anything, it was almost as if he was telepathically tormenting her that she would be a coward if she didn't play at all.

"All right." So she gave in, sitting on the chair across Benny. "But if I win..." She continued after putting down her bag and entwined her fingers together on the table, "you give me five bucks."

For a moment there, Benny became hesitant. Yes, he had a huge stash of money, but five dollars was still a lot. Then again, he wanted to prove her wrong on whatever her reason as to why she didn't want to go out with him. "Deal."

And so, they played. Y/N moved every piece she chose as soon as Benny moved all of his and vice versa, pressing on the button of the time alternately in the process. The others watched intently as she was about to win after a few more moves.

Y/N could feel a smirk playing on her face when Benny's king was already stuck on checkmate with her rook, her bishop, and her queen. She looked at aghast Benny with a smug look on her face. She held up her palm, waiting for him to pay up per their agreement, fluttering her fingers teasingly.

Benny gave a glare at her victorious smirk even though it internally made him melt as he reached for his wallet in his back pocket. He smacked the five dollar bill on her hand, which she gladly stuffed into the pocket of her bag.

He thought she would already be heading home. "How about we go again?" Though Y/N was getting amused by their agreement. "I'm sure you were just warming up." She taunted, "After all, you're the greatest one in the chess club... possibly in the whole United States."

Of course, Benny couldn't help but say yes.

****

Four rounds of speed chess have passed. Most of Benny's friends had already headed home. Yet they were still playing. Benny's wallet was starting to cough up nothing while Y/N's was getting stuffed.

Benny didn't give up that easily. After their first three rounds, Y/N didn't contradict him any longer. He was the one who kept demanding for them to play again.

Y/N didn't want to play anymore as his moves were already predictable to her. At first she enjoyed that she was getting a lot of money from their bet. Now, she just wanted to see what would happen if he won.

The longer they played, the more she realized her liking for Benny wasn't as bearable as it used to be.

She only realized she was too distracted by her thoughts about Benny when her opponent suddenly shouted, "I won! Finally!" He leaning back on his chair out of satisfaction

Y/N blinked vigorously, getting back to her senses to see her king piece was cornered by his queen and his bishop. Now she didn't have a choice but to go in the drive-in with Benny.

But she knew to herself that deep down, she actually wanted to go.

Sighing heavily, she let her hand shake his own. "Nice game." She commented with a faint smile.

While they were shaking hands, Benny glanced up to her eyes and down to her lips. It tempted him to pull her close by the hand and press his own pair of lips on hers. Though, he tried his best to refrain himself from doing so.

As they let go, Y/N quietly bent to her side to grab her bag and stood up, "I'll see you tomorrow night."

With that, Y/N slung her bag on her shoulder and walked out of the room, biting the inside of her cheek to prevent a grin to be evident on her face.

« ~ • ♪ • ~ »

Part 2 anyone? 👀

Have a nice day/night✨

-BloodyinspiredTri 🖤