The Challenge: Ch. 01

Literotic asexstories – The Challenge: Ch. 01 by Cassioirl,Cassioirl
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Chapter 1

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Cassie was having one of those months. In the space of three weeks, she’d been laid off, lost her boyfriend and her car had died.

She’d been sending money to her sister who was caring for her chronically ill mother. So, when everything went wrong at the same time, she was basically broke.

She spent a long evening drowning her frustrations with wine and chatting. She’d been reaching out to several of her friends by phone and messaging, basically just needing to vent.

She’d lost track of time as she jumped between apps typing and recording messages. It was getting late and she was trying to decide whether to open another bottle or go to bed.

She was suddenly surprised to get a message from Val, her old college roommate. After graduation, they’d gone different directions and exchanged messages maybe a few times a year.

From what she remembered, Val had taken a job with some tech company in Austin, Texas while Cassie and stayed in Boston.

— Hey Cass! Are you ok? I saw your stories

— Hi Val. Yeah. It’s shit. But I’m ok.

— What are you going to do next?

— Not sure yet. I’m sending out resumes and working my network to see if I can get a job fast. If not, I may have to move home. I only have enough money for about a month then I’ll have to break lease.

— Are you still doing finance?

— I was

— I know this is out of the blue but my boss is looking for someone and you might be a good fit. Fancy a move to Texas?

Cassie’s head spun. She’d been in Boston for six years and hadn’t thought about moving. Her apartment and friends were here…she’d never even been to Texas.

— I don’t think I can even afford a plane ticket down there.

— The company would cover it. Google the company, sleep on it, see what you think. If you’re interested, let me know tomorrow and we’ll fly you down for the interview. I’ll even show you Austin afterwards!

She really had nothing to lose. A free trip anywhere sounded nice and maybe it would work out? Val was always Ms Business–she wouldn’t waste her time if there wasn’t a chance of this working out.

— Let’s do it! I’d love a trip away and it’ll be fun for us to catch up.

— Done! Watch your email.

The next morning, Cassie got an email with a plane ticket and hotel reservation. Val had arranged for her to arrive Thursday afternoon and set the interview up for Friday morning. There was even a reservation for Cassie at a fancy older hotel downtown just a short walk from the company’s offices. What really surprised Cassie was the return flight was on Sunday.

Val’s company was really treating her well to give a candidate a free weekend away. Or was Val just really important and able to get her friends free trips?

The next couple of days flew by as she waited to travel. Val had her send an updated resume and had her complete some online screening tests–basically personality tests.

In between, Cassie continued her job search online. As excited as she was about Austin, she’d prefer to not have to move.

She finally got around to packing the night before. Val told her to bring some “going out clothes” and a bathing suit. She stuffed her tiny suitcase with everything on the list.

———-

Cassie’s trip was uneventful. The plane landed in Austin and she made her down the escalator to the luggage carousels.

Val was waiting for her. She hadn’t changed since college. She was dressed in an expensive looking black skirt suit and high heels. Val seemed to have a very small top on under her jacket–the V of the jacket showed only skin. Her long hair was tied neatly at the back into a ponytail.

She smiled broadly as she spotted Cassie and waved. Cassie sped over to her and they hugged. Cassie couldn’t help but notice that Val was wearing classy perfume and elegant gold jewellery.

“So good to see you, Cass!”

“You too! You look amazing!”

“Ugh…just work stuff. I snuck out early so I could pick you up.”

“Your boss must be great…all of this is just…”

“Ah, it’s nothing. It’s hard to find the perfect people. So he’s pretty generous–especially if someone in house knows someone. It saves tons we’d otherwise waste on recruitment. Anyway, I’d rather bring in a friend than some randomer.”

“Well, I really appreciate it.”

Val just waved it off.

The two women made their way to Val’s car–a shiny almost new Audi. It looked like Val was doing well. The car was the most comfortable thing Cassie had ever been in. She just melted into the leather seats and soaked in the air conditioning as Val put on her dark sunglasses and sped along the freeway towards downtown.

They chatted along the way. Cassie told Val about her worst ever month and caught her up on her mom’s health issues.

She peppered Val with questions, dying to know more about her life. From what she said, Val was a kind of personal project manager for the CEO. Her job seemed to be to deliver on his pet projects with a team of six she managed.

She said she was living in a penthouse apartment downtown and seemed to be doing amazingly well for a woman just a couple of years out of college.

“So…would we be working together?”

“I might help you onboard…but we probably wouldn’t work together for a while. Maybe after a year or so.”

“Oh. That’s a shame. Do you have any details about the job I should know for the interview?”

“Uh…it’s a pretty standard finance role…basically running models over potential investments to help figure out if they’re worth doing or not. The interview will probably be pretty tough. But, the job is worth it if you get through.”

Cassie nodded. She was slightly disappointed it didn’t seem to be involved with Val. She’d love that kind of success and not to have to worry about money for a change. They were a great pair at college so it’d be like old times again.

They arrived at the hotel and the two stepped out into the hot afternoon sunshine. Val popped open the trunk and one of the porters took Cassie’s modest bag out and carried it inside.

“Go check in–it’s in your name and all prepaid. I’ll go drop off my car and we can meet in the lobby around 6?”

“Perfect. Thanks, Val. This is all great…soo exciting!”

Val smiled back and drove the car away.

———

Cassie checked in and went up to her room to relax before dinner. The room was amazing. Val had gotten her a Junior Suite with a giant bed with separate relaxing and office/dining areas.

Despite being an old hotel, the rooms were thoroughly modern with all the little comforts she could want. The oversized bathroom had separate bathtub and shower. Cassie was getting even happier with her decision to come down by the minute.

She took a quick shower, washing the travel miles away. She always felt a bit grubby after a flight. After, she snuggled into the oversized hotel robe and sat in the bed, resting her back against the headboard.

She flipped through Val’s social media accounts but there was almost nothing to see. She almost never posted anything and rarely commented or liked anyone else’s posts. Even her LinkedIn account was just a minimum profile.

Val had been the crazy one in college. She seemed to have a different guy every weekend. She was at all the good parties and even experimented with some of the girls. Val could drink most of the people around her under the table.

Cassie had only been half as adventurous. She wouldn’t have been the sensible one–their friend Jamie played that role. But, she enjoyed herself and dated a few different guys. Normal levels of college fun, but nothing too wild.

Val had managed to talk her into a few wild experiences and they’d even slept together a few times. But, that all felt a million miles away from now.

She wondered what Val had planned for tonight. Probably just a nice dinner and some drinks. After all, it was a work night and Cassie had the interview tomorrow. It couldn’t be too wild.

Cassie had only brought a few outfits. She decided on her beige slacks and coral top. She always felt it was kind of classy but still casual and fun. Hopefully, it’d get her through the night.

———

At exactly 6pm, Cassie stepped out of the elevator into the lobby. She looked around the cavernous room and spotted Val sitting casually in a low leather chair, idly scrolling on her phone.

She looked up and smiled, waving slightly to Cassie as she stood up. Cassie was relieved to see she’d dressed casually in a classy knee length navy skirt with a blue and white sleeveless V neck top.

“Hey, Cass! Are you hungry?”

“Yeah, I’m starved. What are you thinking for dinner?”

“There’s a great Mexican place just down the street…or we can do Asian fusion or actually the restaurant here is good if you want streaks and seafood?”

They ended up going for Mexican just a few hundred steps away. Cassie loved the heat of the waning sunshine. It felt like summer.

They caught up more over enchiladas and a few rounds of margaritas, their conversation getting more personal as the alcohol built up in their systems. It reminded both of them of being back as college roommates having a girls night in.

“You seem to be doing amazing, Val. Your job sounds interesting, awesome car and an expensive apartment in the middle of town…you’ve been busy!”

“More lucky than anything else. I started as an intern and got on a few interesting projects that the CEO was interested in. He pulled me into other things and a few projects later I was in the Special Projects Team full time.”

“What are you working on now?”

“Ken Bradshaw is our CEO. He has a house in Austin and bought and old run down hotel not far from it. He’s got our team doing it up as a kind of themed retreat centre. Our own company would use it, but we’d also rent it out for events. So…that’ll keep us busy for the rest of this year.”

“That sounds really cool! I’ve never got to do anything interesting in finance. I feel like I’m just running numbers until we land in a model everyone likes.”

“We still get stuck with fun stuff like that. I think we went through a dozen models on this retreat place…adding and changing assumptions until everyone was happy. It never really mattered–Bradshaw had already decided to do it.” She shrugged and sipped her margarita.

“Any other perks of the job?”

Val kind of scrunched up her nose before she answered. “All the usual stuff…there’s a couple of annual meet-ups that can be pretty fun…depending on what you’re working on, you can often be remote at least 2-3 days a week–probably more for you finance people. They pay really well.”

She paused for a bit, looking like she was having an internal debate over what she wanted to say.

“The down side is the company can be a bit…old school…kind of sexist sometimes.”

“Oh…”

“Not like ass grabbing or sexual harassment stuff…more like…subtle. Some of the top dogs like their women to look sexy…so you can lean into that or avoid it and focus on the job.”

Cassie blanched, not sure how she felt about that. She’d had a manager back when she worked retail who was always trying to sleep with her and it got uncomfortable several times.

“Look…you’ll be fine. Your boss would actually be a woman, so nothing to worry about most of the time.”

They both went quiet and drank their margaritas. Despite what Val had told her, Cassie couldn’t help but think there was more she wasn’t saying. Whatever, she thought, she was here now…might as well do the interview and see how bad things might be. She had nothing else yet for a Plan B.

After dinner, the pair walked back to Val’s place to hang out.

She hadn’t exaggerated her place. Her apartment was on the 15th floor, facing west to give an expansive and unbroken view of the Texas Hill Country.

Although only a two bedroom, every room was big and there were three full bathrooms. It was elegantly decorated and very comfortable.

“Grab a seat…do you still drink gin or would you like something else?”

Cassie sank into the oversized and super comfortable couch.

“That sounds perfect…love your view. Just…wow.”

“Yeah, me too. Pity we missed the sunset…hopefully you can catch it sometime this weekend.”

Val mixed them each a drink and joined her on the couch a few minutes later, handing Cassie a very large G&T in a chunky glass with a think, heavy base.

“Cheers!” Val said as they clinked their glasses and took a sip.

They sat chatting amiably on the couch and their drink turned into a second then a third. The conversation followed suit, drifting from the mundane everyday stuff into personal affairs then dating horror stories.

Val slipped off her shoes and curled herself up sideways onto the couch. As they spoke, Val gently grasped Cassie’s arm, then rested her hand on her shoulder.

It felt nice to be touched, so Cassie let it happen, setting her own hand softly onto Val’s knee.

Val leaned over and put her hand on her trapezius muscle and squeezed it gently but firmly.

“Feels like you’re holding some stress, Cass. Let me rub it out?”

Val was great with massages, but Cassie wasn’t sure she wanted to get into that tonight.

“It’s ok…we’re both tired…”

“I’ll just do your neck and shoulders.”

Val set her drink down and walked behind the couch, taking Cassie’s shoulder muscles in her hands and squeezing them. Cassie made a satisfied groan in reply, relishing the pressure on her stiff muscles. Val had taken a massage course years ago and had a magic touch.

Val focused on working her trapezius muscles for several minutes until they released their stress and felt normal instead of like iron bars. She moved on to her neck, working the muscles at the back and base as Cassie relaxed fully, feeling like a floppy doll in Val’s firm grip.

Val leaned down and whispered into Cassie’s ear, “shall we move to my bed so I can work on your back?”

Her soft breath sent shivers down Cassie’s spine. She felt herself growing wetter… Should she make out with her friend…again? Her hands felt amazing and remembering how wonderful her mouth on her felt made the decision easy.

“Yeah…that sounds great.”

Val led her into the bedroom and helped her remove her clothes.

“Just lie down and relax.”

Cassie laid down naked on her stomach, folding her arms around her head. She heard Val open a drawer and then the soft sound of oil being poured. Val put oil into her palms then rubbed them together to warm it up.

She started back at Cassie’s neck and shoulders, giving them a final going over before working her way down her back.

Her soft hands felt so nice on her skin. Val knew the exact pressure to apply to release the tension and make her whole body melt.

Val took her time, working all of the muscles in Cassie’s back before shifting to her arms, then her legs. She worked the legs from the bottom and spent extra time on the thighs, ending with long gentle strokes taking her fingers almost to Cassie’s now very wet pussy.

She finished by working her glutes. Taking her time on the firm orbs before slipping her fingers teasingly into the crack and then just barely rubbing her anus with the oil soaked pad of her finger.

Cassie tried to push back, but Val just pulled her finger back instead of holding it in place.

Val did a final quick rub from left heel to neck then removed her hands.

“Roll over, Cass. Let me finish.”

Without a word, she rolled over, her naked body fully on view, her legs slightly open. She kept her eyes closed.

Val oiled up her hands and rubbed Cassie’s breasts, teasing them with her nails and then gently squeezing her nipples to make them even harder.

Val leaned down and kissed her gently on the lips. Cassie opened her lips and darted her tongue out to purse Val’s–their tongues ending in a deep dance of a kiss.

Val used her still oily fingers to part Cassie’s labia, gently rubbing it back to front, teasing her clit before sliding her fingertips into her.

Cassie moaned into their kiss and Val responded by rubbing her clit, alternating between small circles and back and forth motions. Cassie was soon grinding back against her hand, wanting more pressure.

After Cassie had a small orgasm, Val stopped and quickly slipped off her clothes, tossing them into a pile in the corner. She lay down in the bed on her side next to her friend and kissed her again as she slipped two fingers inside Cassie’s wetness.

Cassie reached between Val’s legs and mirrored her actions by parting her folds then easing a finger inside her.

After a few moments relishing the feeling of Cassie’s fingers, she sat up and straddled Cassie, pressing her clit against hers then began gently rocking against her.

Cassie matched her rythym, giving them both a wonderful sensation as they scissored. Cassie cupped Val’s breasts, squeezing them firmly the way Val loved.

Val seemed to dance above her as she continued to grind against her. It wasn’t long before Val came. She bucked hard against Cassie, wanting more pressure. She slowed her pace way down as she moaned loudly and came in a slow, hard circle.

Cassie was close but needed a bit more. Val lifted herself up and replaced her pussy with her expert fingers and quickly took Cassie over the edge.

When she’d finished, Val lay next to her, Cassie’s head nestled between her arm and breast.

When Cassie’s breathing returned to normal, she turned and laid gently between Val’s legs, kissing her softly before moving down to her breasts. Cassie loved taking her nipples into her mouth and teased them gently with her teeth before suckling them hard with her lips. She’d suck them then pull back, making a soft pop noise as they fell away from her mouth. She knew Val loved having her boobs kneaded and suckled, so she took her time and teased the soft flesh with her nails.

She moved down in the bed and held her mouth just above Val’s pussy. She gently held her folds open so she could see her clit and opening and took a large breath, exhaling slowly onto her most sensitive areas.

Val squirmed under her, bucking involuntarily upwards vainly searching for her tongue.

Cassie smiled and repeated it three more times, enjoying making her friend squirm in desperation. Finally, she lowered her head and ever so softly licked her from her opening towards her clit, teasing the nubbin with her tongue before licking her again and again.

Between moans, Val breathlessly said, “you’re so mean…such a bitch…”

Cassie giggled–she loved making Val desperate–but stopped teasing her and focused on her clit. She gently massaged it with her lips, playing the alphabet game with her tongue. She brought up her hand and slid three fingers easily inside her, bending her fingers into a claw shape to focus on her g-spot.

Val gently held Cassie’s head in her hands, stroking her hair and cheeks.

She found the perfect pace, sucking, licking and finger fucking Val who shifted beneath her, trying vainly to lean into something–all at once wanting more, faster, both, everything.

Val exploded, cupping her head in her hands, pulling it tighter against her as she cried out, the waves of pleasure rolling over her as Cassie worked on.

Cassie alternated her efforts, helping Val through at least three orgasms and finally slowing down as Val’s grip on her head loosened. She stopped moving her hand, slowly pulling it out of Val’s pussy. She opened her mouth, releasing her clit, but giving it a gentle kiss before she pulled away.

Val gently pulled her shoulders, helping her to lie against her again where they cuddled and kissed softly. When Val regained her composure, she returned the favour before the two women fell asleep in each other’s arms.