Unlikely Cheerleader Boyfriend Ch. 01

19 year old Tom could barely believe how much his life had changed in the past couple of months. He had gone from a quiet kid who would keep himself to himself, only really leaving his house to go to the gym or for a run as well as attending college, to having two cheerleaders effectively at war over him.

It had begun one day, when Tom, after school was working out in the gym, as he did most days. Mid way through his work out, he was surprised when he looked up and saw Jill, the colleges head cheerleader stood next to him, observing him.

Initially unsure of how to react, he removed his headphones "Erm, hi" was all he could manage.

"Hey, its.. Thomas isn't it?" She said, still looking at him. Jill was in the top 3 most popular girls in his college, every boy dreamed of talking to her but few could work up the courage to. She was half Japanese and half English, standing at just 5 foot 5 inches, but had a bubble butt that was huge in comparison to her height.

"Erm, yes, you can call me Tom though. You are Jill aren't you?" He asked, immediately realising how much of a pointless question that was. Of course he knew who she was, the whole college did.

"I was just admiring you while you worked out. Don't mind me" she said, though when Tom glanced behind her he saw at least 8 other cheerleaders looking over at the pair and laughing. His face immediately went red. Was this some sort of joke? Was he about to be the target of the notoriously catty cheerleaders?

Jill followed his gaze and realised he had gone bright red. "Oh baby ignore them, do you want to get out of here?"

"Erm, yeah sure" Tom replied, placing down the dumbbells he still holding. Despite his impressive, muscular frame, he was reserved whilst talking to people he didn't consider to be his friends, and especially around people lie Jill, who moved in completely different social circles to him.

"Meet me in the reception in 5 mins honey" she said.

He went to get changed. All that was going through his mind was thoughts of potential embarrassment. What was he missing? Would all the girls be filming his reaction when he saw Jill wasn't waiting for him? Was this some sort of joke at his expense? Only one way to find out, he thought, opening the door into reception.

But, sure enough, there she was. She was all alone and smiled when she saw him.

"Whats the plan then?" She asked him, her face still wearing a gentle smile.

Fuck Tom thought, what is the plan? Where does a quiet boy take one of the most popular girls?

"Erm, we could go down to Starbucks, my friend works behind the counter so he can get us the staff discount. I'll buy." Tom said, just about managing to piece together a plan as the words left his mouth.

"So that's what I'm worth to you? Your taking me there because its cheaper huh?" Jill teased.

Tom did not realise Jill was just teasing him "Erm, no that's not what I meant, we can go somewhere else, anywhere you want" he managed to speak, in a nervous voice.

"Im teasing you Tom, Starbucks is fine by me, I haven't been in weeks."

The pair chatted over a coffee. Tom found himself more and more at ease with Jill as the minutes passed by. He couldn't believe it, Jill Wilson was talking to him and it was actually going pretty well. Jill was also enjoying herself, she couldn't believe how nice Tom was. This is the first time I've spoke to a boy who has been respectful and polite towards me in years, she thought to herself.

Of course, the evening had to come to an end, but it was Jill who said "Ive really enjoyed tonight Tom. We need to do it again soon" she said and kissed him on the cheek before hurrying off to a waiting taxi. Tom could barely believe how his night had panned out.

The next day at college, Tom was eating lunch with Jonathan, his best friend, who had served both him and Jill at Starbucks the night before. "Tom, how on earth did you end up alone with Jill fucking Wilson?"

"It was a blur. I dunno she just kind of asked me to take her somewhere and all I could think of was Starbucks".

Jonathan could not believe Jill was the one who had suggested the 'date'. The pair of them just fit in at college, most people in college barely paid any sort of attention to them. Yet Tom had managed to secure a date with Jill, and it seemed it had gone pretty well. Jonathan shuck his head in disbelief.

"She is over there look, sat with her friends. Why don't you go over and talk to her" Jonathan offered his advice.

"That would be suicide Jon. I mean kids like us don't just walk up to the cheerleaders table do we".

Jonathan couldn't really argue with Tom's logic. But on the other side of the room, Jill wanted nothing more than for Tom to come over and speak to her. She was already beginning to fall for him. Her brain was in turmoil. Girls like me don't date boys like him, she kept telling herself, but at the same time she already knew she wanted to be with him. The way he looked at her, like she was the only girl in the world, melted her heart.

The days passed and Tom desperately wanted to speak to Jill. But he just couldn't find the courage to go over to the cheerleaders table at lunch time and apart from that, there wasn't really another opportunity to speak to her. He didn't have her phone number and didn't want to message her on social media, in case she just ghosted him.

For her part, Jill was sad that Tom hadn't come and spoke to her. Usually, boys would be desperate to speak to her again, but for the first time she had fallen for a boy, he was seemingly not interested.

The days turned into weeks, and Tom began to forget about Jill. No longer were his lunch breaks in the canteen spent glancing nervously over at the cheerleaders table. Sure, it would be a cool memory, taking Jill Wilson out for a date, but that was all it would be, he assumed.

That weekend, he arrived to a party hosted by one of the richest kids at his college. The house was that big that invites weren't even sent out, anyone could come.

Tom was hanging around, speaking to a few people he knew but not really fully fitting in, when Holly, another cheerleader came up to speak to him. Holly was a quieter and less well known member of the squad, having a personality more similar to that of Tom.

"Hey Holly how are you doing" he said. As he said it he realised how ridiculous the pair looked stood next to each other. Tom was dressed in a pair of old jeans and a cheap unbranded shirt, whilst Holly was all dolled up in a dress and cute high heels.

"It's a bit loud in here isn't it, do you fancy going somewhere a bit quieter?" Holly asked.

As she began to walk off, Tom followed her. They ended upstairs in one of the many guest bedrooms.

The pair laid on the bed and began chatting about various topics, from the size of the house they are in to the plans they had for life after college.

"I think you are such a cool guy Tom. Even Jill likes you and that's saying something" Holly said. The mention of Jill's name peaked Tom's attention. Even after a couple of beers, he was sure he would still be too shy to approach Jill.

"Cheers, Holly, you too. Your actually you know, like a real person, unlike some of the cheerleaders" Tom didn't even really know what he was saying, words were just coming out of his mouth.

"Just shut up and kiss me" Holly said, shuffling across the bed and holding the back of Tom's head with her hand. The pair tangled in a mess of limbs for the best part of a minute, neither one wanting to be the one to break the kiss.

It was Holly who eventually broke it off, "Wow Tom who knew you were such a good kisser" she said.

"That was incredible Hol" Tom said.

"We aren't finished yet babe" beginning to tug Tom's jeans down. "Tell me what you want me to do to you babe" she said.

"Erm, I want you to.. suck my cock" Tom said, his voice shaking. He had no clue whether Holly actually would, but it worth a try, he figured.