This story is a prequel to Best Friends Forever, and Best Friends Forever part 2.

Katie

Katie was finished with men.  She really thought that the guys at college would be different- more mature, less terrified of commitment than the ones from her small-town high school.  It’s not like she wanted to get married or anything, but she was looking for more than clumsy sex and late-night booty calls.  She had just told her boyfriend- if you could even call him that- Jason as much when they had lunch today, causing him to mumble some sort of “I’m not ready” excuse and promise to call her.  His loss, Katie knew, but she was still frustrated with her love life. 

She was ruminating about it as she got back to the apartment that she shared with her best friend Julia; the two women had moved to the big city for college and split on an apartment to save money.  They had fairly opposite class schedules, which today Katie was glad about as she let herself in and padded down the hallway to her bedroom.  She got along well with Julia- they had been best friends since they were kids- but Katie found herself in a foul mood and just wanted to be alone.  She flopped down on her bed, taking a few deep centering breaths as she tried to push Jason and his nonsense out of her mind. 

The deep breathing didn’t work.  She was so frustrated with Jason- not that she was particularly head over heels for the guy, but even she had to admit that she had a crush, and she was irritated that he didn’t even want to explore what could be with her.  She knew that she had to let it (and him) go, and it wasn’t the loss that she was mourning- more just the principle of the thing, having now to go back to the drawing board to find a worthy partner.

Katie’s phone buzzed, momentarily distracting her from her pity party.  She smiled when she saw Jack’s name pop up on the screen.  Katie had met Jack in her first year of college, and they’d become instant friends.  He and his girlfriend Michelle hung out at Katie and Julia’s often; Michelle and Katie were in many of the same classes, so they often did homework together.  Jack was asking what she was doing later.  Katie scoffed at the question- not like she had a boyfriend to hang out with- and told him he and Michelle could come over.  “Just me,” he replied, and Katie sent an emoji in acknowledgement.  Just me was the story of her life.

Her phone lit up again, this time Jason’s name on the screen.  She rolled her eyes, but couldn’t ignore the skip in her heartbeat.  Maybe he had reconsidered? Wanted to give them a real shot? She eagerly opened the message, only to feel her heart sink: “Can you bring my hoodie to class on Thursday? Thanks, and sorry Katie.”  His half-hearted attempt at an apology hit a nerve with Katie, and she slammed her phone down in frustration.  She knew the exact hoodie that he was talking about- he had left it the week before after he’d stayed over, and she had been sleeping in it ever since.  She grabbed it off the floor; she would give it back, but thought it complimented her pity party nicely, so she took off her shirt and bra and put it on. 

The worn fabric was soft against her skin, and she curled back up on her bed to feel sorry for herself a little while longer.  Katie knew she was a catch- smart, ambitious, pretty- she got a ton of compliments on her fiery red hair- plus she had a great ass thanks to her commitment to the gym.  Her self-pity was slowly replaced by indignation and anger; she was hot, smart, and hilarious- any guy would be lucky to be with her.  Jason was mediocre in every sense of the word, and clearly wasn’t worth her time.  She would find someone better and leave him behind her- taking in the view of her incredible ass as she walked away from him. 

She was feeling petty and grabbed her phone to reply to his text.  She took a photo of her in the sweater- sexy, tousled red hair, pouty lip, big eyes.  “This one?” she replied, sending the photo.  She then took a few more, each one showing more and more of her body.  She pulled the sweater up so that the underside of her breasts were showing, and snapped a photo.  The sweater then went up over her breasts, her nipples hardening as she took another.  She took the sweater off along with her jeans and panties.  She held it against her skin, strategically placing it so that it covered her below the waist while keeping her breasts on full display- photo.  She spread her legs, touching the sweater to the wetness between them- photo. 

Her fingers wandered along the sweater, following it to the sweet spot between her legs and starting to rub.  She dipped a finger inside herself, smirking at her wetness as she explored- turns out petty revenge is a turn on.  A moan prompted her to rub faster, her body squirming to meet her touch.  She felt her hurt and frustration channel out of her as she crept closer and closer to orgasm.  As the tension built inside her, she craved more. 

Reaching into her side table, her hands grasped her favourite dildo and thrust it inside her. One hand teased her clit while the other worked the dildo, Katie’s body a heated blend of sensation and movement.  Jason’s sweater had worked its way underneath her as she fucked herself with the dildo, her moans echoing in the empty apartment.  She snapped a few more photos as she touched herself, really wanting to show Jason what he was giving up.

She heard her orgasm before she felt it; her pussy gushed squirt around the dildo as she fell over the edge.  The wet sounds of the relentless dildo turned her on even more, and she screamed when she launched into her orgasm.  Her hands didn’t let up, demanding every ounce of cum and sensation from her body, until she was a soaking, panting mess. 

She floated back down to earth, trying to catch her breath and center herself as her body trembled in the aftershock.  She sat up slightly, laughing as she saw Jason’s sweater covered in her cum.  She didn’t always squirt when she played with a dildo, but when she did- it was messy.  She snapped a few more photos of the soaked sweater between her open legs, her pussy quivering as she held her lips open to show her swollen clit.  She made sure to get her face in the photos, a look of pure ecstasy in her eyes- who needs men, anyway?

Katie sent the rest of the photos to Jason- a parting gift, as it were.  “Fine, Jason- you can have your sweater back, but you won’t get me back!” she typed, and hit send before throwing her phone on her bed.  She felt fully cleansed of Jason now, and set her mind to grabbing a bite to eat before Jack came over.  She didn’t realize that he had texted to say he was almost there, and that her life was about to change forever.

Jack

Breakups were the fucking worst.  Jack and Michelle had been together since high school, following each other to college with big plans for their lives.  Jack had invested everything he had in their relationship- he saw Michelle as his soulmate.  Clearly, she didn’t agree.  She had sat him down and told him that she didn’t love him anymore- just like that.  She gave him some lines about college opening her horizons, and her wanting to explore and “find herself”, whatever that meant.  Not amount of reasoning (okay, grovelling), could make her change her mind.  She was breaking up with Jack, and there was nothing he could do about it.

That conversation had happened a couple of weeks ago, and Jack had finally accepted that he and Michelle were done. He had spent two weeks in his own head, shutting out the world and feeling sorry for himself.  His inner introvert was pleased with this approach, but he realized that he couldn’t be miserable and heartbroken forever. 

He didn’t want to be alone anymore, and realized that he needed a friend- he reached out to Katie.  They had been friends for a couple of years, and he really valued her insight- he knew she would make him laugh and feel better about things.  He showered and got dressed, sending a quick message to Katie to tell her that he was on his way.  He had just gotten in his car when his phone buzzed in his pocket.  Katie had sent photos.

Jack never in a million years would’ve anticipated what was waiting for him on his phone.  Katie had sent a bunch of photos of herself in varying stages of undress, the photos getting more and more explicit until she was touching herself and…had soaked the sheets.  Jack read the accompanying text- to Jason- and realized that Katie had accidentally sent the photos to him.  He guessed by the lack of panicked follow up texts that she hadn’t realized her mistake, and sat in stunned silence as he debated what to do next.

Jack couldn’t help himself- he scrolled back through the photos, taking in Katie’s gorgeous body and each delicious pose.  He felt his cock twitch in his jeans every time he opened a new photo.  He zoomed in to see her perfect nipples on sumptuous breasts, the way she bit her lip as she touched her bare pussy, and the look of satisfaction and pleasure on her face as she laid in her mess.  Jack licked his lips, shuffling in his seat to accommodate his hardening cock. 

How had he never seen how beautiful and sexy Katie is?  He had only ever thought of her as a friend, but now had many, many more ideas.  Maybe Michelle didn’t want him, but that didn’t mean he had to be alone forever.  A plan started to form in Jack’s mind as he drove to Katie’s apartment.

—

They greeted each other normally when Jack arrived; he couldn’t see any signal that Katie knew he had the photos, and carefully controlled his face so as not to give himself away.  It was very difficult to keep eye contact with Katie, as he found his gaze drifting over her curves and landing snugly in her cleavage more often than not.  Had she always smelled so sweet?

He idly wondered what her lips would taste like as she poured them each a drink.  She had changed into a tank top and tight black yoga pants, a fairly typical outfit for a casual night in.  Katie had ordered a pizza, citing Julia’s late-night class and her breakup with Jason as reasons for not cooking.  Jack used that as a window to disclose his own breakup.  Katie met his vulnerability with sympathy and commiseration, and the two friends drowned their sorrows in pizza while lamenting about the struggles of finding love.

Jack tested the waters with a few playful comments about he and Katie helping each other get through their respective breakups.  “Well now we’re both single, we could always keep each other warm at night,” he said nonchalantly. 

Katie wrinkled her nose, laughing off his comment, “Yah, that sounds healthy,” she scoffed. 

Jack tried a couple more times, his tone noncommittal as he suggested a friends with benefits arrangement, and drawing similarities to their friendship and a relationship.  “I mean, we spend all of our time together anyway,” he said with a shrug, “what’s the harm in getting naked every now and then?”  Katie didn’t budge, taking his comments to be purely rhetorical and laughing him off.  Jack felt a surge of frustration, and decided to change his tactic.  Plan B would be a little less gentle.

“So, have you heard from Jason?” Jack asked casually as they hung out on the couch after dinner. 

“He asked me for a sweatshirt back,” Katie said with a roll of her eyes, “but that’s it.  It’s definitely over- good riddance,” she said with only a trace of bitterness. 

“The green one?” Jack asked innocently, smiling as confusion played across Katie’s face. 

“How do you know it’s green?” she asked, the mood in the room suddenly anxious.  “

I didn’t know how to tell you this, Katie, but…I got the photos.  You must’ve sent them to me instead.” 

Katie’s face flushed, her eyes no longer able to meet Jack’s.  “No, that’s impossible,” she said, her voice laced with panic as she bolted to her room to get her phone.  “No, no, no, no, no!” she yelled from her bedroom as she confirmed her mistake. 

Jack kept his face neutral as she returned to the living room.  “Jack, I’m so sorry,” she said, her eyes almost teary.  “I had no idea…did you…did you look at them?” she asked, eyes glued to the floor as she sat back on the couch- the furthest point away from Jack that she could comfortably sit. 

“I’m only human, Katie,” Jack said with a laugh, “they were so fucking hot- I couldn’t help myself.” 

Katie flushed brighter red, fidgeting with her hands as she stared at the ground.  “Please delete them, now,” she begged quietly.  She was clearly embarrassed, and Jack felt for her.  He had a choice to make- go forward with his plan, or relent and show her mercy.  He considered his position, his eyes focused on Katie’s flushed face and vulnerable energy.  He was only human.

“I don’t think I will,” he said calmly.

Katie looked up, finally meeting his eyes.  Hers were scared, darting around like a caged animal’s might.  “What do you mean?” she asked, incredulous.  “I said delete them, Jack- I didn’t mean to send them, and they aren’t for you.” 

Jack leaned back on the couch, relaxing his posture.  “You were sending them to a guy who doesn’t even want you,” he said directly, “I do want you, Katie.  I wasn’t kidding when I said we could take care of each other’s needs.  I think you should reconsider.”

Jack could see Katie assessing him.  She didn’t speak, but sat up straighter and squared her shoulders, seemingly preparing for a battle- except Jack held all the weapons.  “Like I said,” he continued in his easy tone, “we are both single now- both reeling from relationships ending.  We are already friends, we might as well make it more.  Plus, I’ve already seen you naked now,” he said with a knowing smirk.  He looked Katie up and down, intentionally disarming her as she squirmed under his gaze.

“Jack, delete the photos.  This isn’t funny,” she said timidly.  Jack had to admit he was enjoying seeing his typically headstrong and confident friend withdrawn and unsure- all because of his influence. 

“I agree,” he said smoothly, “I am very serious.  I think you should reconsider your position, Katie.  You don’t have the power in this situation.”

He moved closer to her on the couch.  She was all the way at the end, so she stood to widen the gap between them.  “I think you should leave,” she said, her voice shaking. 

Jack’s gaze didn’t waiver, his eyes focusing on her face, daring her to make eye contact.  He could see her lip quiver slightly, which was all the motivation he needed to make his final play. “I’ll leave, Katie,” he said.  Her body language demonstrated her surprise, but she quickly recovered.  “but not before I am sure you understand what’s happening here.  I have some very compromising photos of you- leverage, if you will.  There is nothing stopping me from sending them to anyone- Julia, your professors, your family and friends.  Of course I won’t do that- I care about you- but I would be remiss if I didn’t see this as an opportunity for me to get something that I want.  Do you know what I want, Katie?”

Katie blushed, her gaze refocused on the floor.  Jack watched as she wrestled with herself, making an effort to finally look him in the eyes.  “Jack, don’t.  Please.  Don’t do this to me,” she begged. 

“Admittedly, this isn’t how I wanted this to happen,” he allowed, “but I think in time you will come to see it as what’s best for both of us.  We can support each other, now beyond just friendship.”  Jack stood, unfolding his tall frame from the couch and taking a step toward a cowering Katie.  He was gentle in his approach, touching a strand of her gorgeous red hair and tucking it behind her ear.  He took her face in his hands, tilting it up to meet his. 

“You are going to be mine, Katie, until I decide otherwise.  I care about you, and I will take care of you- but you won’t tell me no again.  Do you understand?”  Katie nodded.  “Good girl.  I will leave now- I don’t want to make you any more uncomfortable.  I will keep the photos, but I won’t show them to anyone- they’ll be our little secret, just like this arrangement.  I will message you tomorrow,” Jack promised, kissing her gently on the forehead. 

To an outside perspective, his actions and body language would appear careful, loving, gentle.  Those were not the intentions playing in his mind as he left the apartment.

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