The First Time

Kelsea Ballerini hadn't taken her rise to prominence in the country music world lightly, and the one thing she was quickly becoming known for was being personable with her fans.

One of the ways in which she had done this recently was by taking a female cancer patient of hers to the CMA Awards as her date for the evening, and while it was something Kelsea didn't expect to make a habit out of, she eventually received so many letters about it that for her next awards show appearance, she decided to do the same.

This time around, it was the ACM Awards, and, after seeking permission from the people who run the show, Kelsea indeed start to make plans to have another terminal cancer patient as her date.

Only this time, she had decided to give one of her male fans a thrill of a lifetime by having one of them be her date for the show.

After poring through the many e-mails that the young, good-looking blonde received upon making that announcement on her social media platforms, she settled on a young man named Timmy, who had terminal brain cancer and by who's own admission she already knew that she was the only thing that could brighten his world.

Despite having only talked to the boy, who was only 18 and therefore 4 years her junior, on the Internet, Kelsea found herself already developing an attraction to him and swearing to herself that she would go out of her way to make it the best night possible for him.

Finally, when awards night approached, Kelsea felt the butterflies in her stomach for many reasons, and not all of them having to do with her being nominated for both the Best New Artist award and the Best Female Vocalist award.

"Timmy, hi. Nice to finally meet you in person," Kelsea told her cancer-stricken date when she met him in person for the first time at the hotel, seeing him flanked by his parents and looking nothing like the cancer patient that he was in a pair of tight blue jeans, baseball cap turned backwards and checkerboard patterned t-shirt.

"Kelsea. Thanks for making the rest of my life," he told her, the occasional coughing spells and the bandana he wore on his head under the cap the only signs of the cancer that was wrecking his body.

"It's my pleasure. I've always wanted to be known not just as an artist who makes good music, but also as one who goes out of her way to be nice to her fans," she told him, smiling sheepishly and averting her eyes playfully as she subconsciously began to flirt with him.

"I know it hasn't even really started yet, but I know I'll remember this night for the rest of my life Kelsea," he told her as he looked her in the eyes, both of them already starting to feel an attraction they had never felt before.

"We just wanted to thank you for giving our son this opportunity to enjoy what's left of his life Ms. Ballerini. You know, the doctors say he doesn't have much time left, even if it doesn't look like it," his parents told her as Timmy put on his tuxedo and joined them in the room.

"I'm sorry to hear that, but hopefully I can take his mind off of it for a little while. And please call me Kelsea, as Ms. Ballerini is my mother," she told them, shaking each of their hands and telling Timmy that their limo was waiting.

"I'm sure you get this all the time Kelsea, but you sure do look beautiful tonight," Timmy told her as they chatted in the limo, placing a hand on her bare thigh as he looked her over in the turquoise dress she was in.

"Not as much as you would think Timmy," Kelsea responded, smiling flirtatiously at him as she subconsciously opening her legs a little to give him more thigh to place his hand on as they continued to grow closer, the limo arriving at the red carpet right as she contemplated kissing him.

"Smile for the cameras Timmy. A lady always likes her date to look his best, you know," she told him, grabbing him by the arm as they walked the red carpet, both of them feeling something they hadn't felt for anyone else before.

"I can tell you're not feeling well babe. Let's go in and sit down," Kelsea whispered to him after they had been on the carpet for a while, hearing him stifle his pained moans of sickness as they headed inside.

"I'm feeling better now that you called me babe," he teased her, drawing a giggle from her as they settled in for the show, which proved to be a major success as Kelsea would go on to win her first major country music award for Best New Artist, which was marked by Kelsea embracing Timmy in a long, deep hug before she went on stage to accept.

"What's wrong Timmy? You not feeling well again?" Kelsea asked him, concerned, as the show ended, seeing him start to mope around as they headed off for the limo.

"I don't want this night to end Kelsea," he whispered to her as the limo pulled up, both of them getting inside as Kelsea pulled him in for a kiss.

"It doesn't have to baby. Come up to my room with me," she whispered, kissing him again as Timmy wrapped her in his arms and returned it, both of them finally beginning to give into their desires.

"MMM...Kelsea...I don't know how to tell you this...but I'm a virgin..." Timmy sheepishly told her as they made out in her hotel room, having spent the whole limo ride over making out and pawing each other.

"It's okay baby. So am I. But I don't want you to die as one, so how about we both change that tonight?" she whispered as she hit her knees and undid his tuxedo pants, wrapping her hands around his hardening dick as she stroked it a few times.

"OH GOD. F-FUCK. Keep doing that Kelsea..." he hissed as she stroked it a few more times, only to then wrap her lips around it and start sucking him off.

"MMM...suck it baby..." he hissed as Kelsea sucked his dick, wrapping her hands around it once more to hold it in place.

Kelsea was no stranger to blow jobs despite having never had sex with a guy, as up until now she had never wanted to go any further than oral with anyone she had ever met, so her oral skills belied her lack of any sexual experience, which was really starting to get to Timmy as he struggled to keep up enough strength to prolong it.

"Cum for me Timmy. It's okay. I'll do all the work later," she whispered to him as she went back to work on his dick, deep-throating it as he lurched his hips into her face and came down her throat, exploding in orgasm as he shot his cum to the back of it.

"MMM...FUCK that feels good..." Timmy moaned as he shuddered from head to toe, Kelsea sucking down on his dick as she swallowed his load.

"Take me Timmy," Kelsea moaned as they started to make out on the bed in her room, Timmy hooking his thumbs under the straps of her dress and watching it fall to the floor as he kissed her with more passion than ever, his hands going between her legs and sliding her panties off as she ripped his tuxedo off of him.

"All I ever wanted was to have sex once before I die. The fact it's going to be with the girl my dreams are made of makes it even better," he whispered to her as he lined his dick up with her dripping wet pussy and ran it along her lips, Kelsea hooking her legs into his back and using them to try and force him up inside of her.

"UH," Kelsea moaned as he placed his mouth over her nipples and started to suck on them, siding his dick into her and hitting her hymen after a few hard, quick thrusts into her.

"You ready baby?" he asked her lovingly as he pulled out, looking her eyes and kissing her again as Kelsea lifted her hips off the bed and wrapped her arms around him, forcing him inside of her.

"Fuck me. Let's be each other's first time Timmy," Kelsea whispered as Timmy started thrusting inside of her, tearing her innocence away with one hard, well-placed stroke and then starting to thrust deeper and deeper into her.

"OHGOD. OHGOD. YES. Feels so good...fuck me..." Kelsea moaned as Timmy drove himself in and out of her, her legs squeezing as tightly around his waist as they could be as she arched her back and threw her head back.

"If you want me to pull out tell me Kelsea," Timmy whispered as he started to suck on her tits again, the pressure her cunt walls were applying to his dick beginning to draw him close to another orgasm as he buried himself balls-deep inside of her.

"Keep going...don't you dare pull out now Timmy..." she moaned, her hands clawing at the bed sheets as she twisted her hips around his dick and her eyes rolled into her head, her orgasm about to take over.

"Gonna...gonna...gonna c-cum...OHGOD," she shouted as she came all over his dick, her pussy clamping down tightly onto it as he sawed himself in and out of her, the squeezing of her vaginal muscles making it impossible for Timmy to pull out in time.

"FUCK. Gonna cum in you Kelsea. Too late to pull out," he moaned as he pushed his hips into hers and buried his dick inside of her up to his balls, his cum starting to spray out into her pussy as he came in her with force.

"OHGOD YES. Fill me with your seed Timmy," Kelsea bellowed as Timmy shot his thick load into her, shot after shot of it filling her until he had nothing left to give and pulled out of her.

"HUH, HUH, HUH. OHGOD. I can't believe you actually let me cum inside you. What if you get pregnant and I can't help you raise the baby-" Timmy stammered as he struggled to catch his breath, Kelsea calming him with a kiss as she switched places with him, climbing on top of him and lowering her pussy down onto his dick again.

"Relax baby. You let me worry about that. You just enjoy the night you're having with me," she whispered as she started to bounce up and down on his dick, Timmy sharply thrusting up into her as she rode him.

"Ride...me...Kelsea...FUCK my head hurts..." he moaned as he struggled to keep up the pace, his head beginning to ache from the tumors inside of him as Kelsea rode his dick like it was the last one she would ever have.

"MMM...right there..." she hissed as Timmy slammed his hips up into hers, finding her g-spot and keeping up the rhythm of his thrusts as Kelsea encouraged him along to the finish line.

"Stay with me Timmy baby. Just a little more and you can cum inside me again," she purred as she lowered herself down onto his dick one last time, holding herself there as he thrust up into her and grabbed her hips, pulling them into his.

"FUCK YES. Cumming," she shouted as loud as she could, losing all sense of anything but wanting to feel the dick buried inside of her releasing its love juice into her again as she painted it with thick strands of her pussy juice.

"OHGOD...YES...cumming Kelsea...inside your pussy again baby..." Timmy moaned as he thrust up into her hips one last time, grunting as he released his load into her, thick streams of his life seeds filling up her cunt and traveling into her womb before he finally managed to empty himself into her and pull out of her.

"You felt so good cumming inside of me Timmy. I'll always remember my first time. And the special boy who shared it with me," Kelsea whispered, running her hands over his bandana as she kissed him and reached for his phone.

"Kelsea, I wish I had enough strength left to fuck your ass," he whispered as she placed a finger on his lips to quieten him and kissed him, texting his parents from his phone as they laid in bed together and recovered from the amazing sex they had just shared.

"Aw, don't worry about it Timmy. Besides, I'm pretty sure I love you, which means you can be my date to all these things from now on. Because I know you can beat the cancer baby," she told him, nervous at how he would react to her telling him those words so soon after what they had just done together.

"If I beat this cancer, can I call you my girlfriend Kelsea?" he asked her, kissing her as she giggled and shook her head yes, pulling him for a deeper one as his parents texted back.

"Of course you can baby. But your parents should be here soon, so why don't I leave you my number and let you go get some rest. Call me anytime you want to," Kelsea told him as she typed her number into his phone, both of them getting dressed as his parents arrived.

"Keep in touch," she whispered to him, holding his hand and kissing him first on the cheek, then on the lips, as she bid all three of them goodbye, not knowing when, or if, she would see him again.

And it wasn't until a few months later that Kelsea would hear from one of them again, but it wasn't the news that she wanted to hear.

"Kelsea, it's Timmy's mother. We...we...lost him last night..." she heard Timmy's mother crying into the phone, the words hitting her like a ton of bricks as she, too, hit her knees and started crying.

"I...need a moment..." Kelsea cried as she hung up the phone and locked herself in her bathroom, bawling her eyes out at the loss of the only guy she had ever truly loved.

"Yeah, yeah. Definitely I'll do it. I just want you to know I loved your son more than any guy I've ever met," Kelsea told Timmy's parents a few days later as she met them at the funeral, agreeing to their request to sing at his services.

"This song's for you Timmy. Wherever you are," Kelsea said into the microphone as she started into a cover of Rascal Flatts' song "What Hurts the Most", tears filling her eyes as she struggled to finish the song, placing a red rose on his coffin as she hung her head in the black dress she was in and paid her last respects.

"I love you Timmy. And I always will," she mouthed as they lowered him into the ground, before suddenly running off due to the nauseous feeling and upset stomach she was, and had been experiencing, for a few weeks.

"I wish this morning sickness I've been having lately would stop. There's no reason for it other than if I was...NO...it couldn't be that, could it?" she told herself as she leaned her head against the wall and held her stomach, the tears flowing all over again as the memory of that night she shared with her now-deceased first love came back to her, knowing it could only mean one thing.