Cayley's Summer Job

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Cayley's cousin sets her up to lose her virginity.
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barkirk
barkirk
3,036 Followers

All characters in this story are at least 21-year-old...seniors in college and above.

This story was prompted by Jennifer who outlined the plot. I hope my weak attempt at fleshing out the outline met her expectations, but this was a fun plot and many thanks to Jennifer for inspiring it.

* * *

"Fudge!" Cayley exclaimed. "Why? This makes no sense," she spat tossing down the letter.

"What? For God's sake, why can't you say 'fuck' like everyone else? Let me see that," Emily came over to look at the letter her cousin received. "What the fuck?" she said, "Going into your senior year they decided to reject your student loan application? What are you going to do?" she asked. "Crap, Cayley. You can't drop out. Fuck!" She came over and hugged her cousin, her best friend.

"I guess I'll take that job mom suggested over at the hand tools plant. They pay well and after a couple of years of saving I can finish up," she sighed.

"I'd suggest we go out, get you drunk and laid, but sadly you just don't do that sort of thing," Emily sighed. She paused and looked at the cute blonde, "I know you'll say no, but what if you ask dad...not for money but a loan? We know you'll pay it back and whatever interest the fucking bank would charge you, I know dad would happily match that."

Cayley shook her head, "I know you love your dad and all that but, I don't know. The way he looks at me creeps me out. I know he's your father and you don't see this side of him but..."

"No, you're right. Mom divorced him because he can't keep his dick in his pants. He's...I guess he's who he is, but he's got so much money you should just see what he says," Emily sighed. "I want you to stay. My senior year would suck without you at graduation. It would feel empty if you don't stand with me."

Cayley and Emily grew up together, vacationed together, and were seemingly in the same classes at the same schools but couldn't have been more different. Emily was a total extrovert living in the moment, loving the spotlight, while Cayley always lived in the peripheries, thinking of the future and rarely making snap decisions.

Outside of both being white girls, they again were almost opposites. The dark-haired Cayley had deep brown eyes, a Mediterranean complexion, large pendulous breasts, and a full ass. Blonde, willowy Emily had sparkling blue eyes, perky small breasts, and a tight ass set on narrow hips. More than once Emily would come up behind the well-built girl, cup her breasts and sigh, "I just want to know what these would feel like on me."

Socially, neither girl ever had a steady boyfriend, but not for the same reasons. Emily enjoyed brief, erotic flings with a variety of boys, open to anything, anywhere. It was not unusual for her to have two dates lined up on the same day..one in the afternoon, one in the evening. Cayley was holding out...not exactly saving herself but holding out for a boy who loved her and she loved back, but every boy so far was overly physical, more interested in her body rather than her person, and rarely went past a single date.

The one time that Emily took Cayley to a bar to pick up guys...actually just one guy. A guy who'd break down Cayley's resistance...break her cherry. She'd finally agreed to wear a top she's borrowed from Emily, low-cut without a bra. She could barely breathe it was so tight and just about every guy came over putting moves on Cayley while Emily felt like a third wheel. In the end, though, it was Emily that went home with one of the guys while Cayley left on her own. The result was Cayley felt something intriguing inside her realizing she was somewhat of an exhibitionist.

That night was the first time Cayley touched herself. She was lying in bed remembering the dozens of pairs of eyes looking at her breasts, or more specifically her nipples. The more they looked the harder they seemed to get causing more boys to look. She explored them with her fingers sending a shock wave straight down to her groin. She hoped Emily wasn't home as she let out a loud groan, surprising herself. She felt strange as if she had a chemical imbalance...on top of which, her pussy was sopping. Thinking about the cold shower cliché, she decided to take one which calmed her down considerably.

"It doesn't hurt to call," Emily said, "the man has the money and he should help family," she said as she picked up her phone.

"You don't have to..." Cayley protested.

Emily held up a finger, "Dad, how are you? No, I'm fine...close, I don't need any but Cayley does. She got rejected for her student loan...I know, it sucks, but anyhow she's just a year away from her..."

Cayley sat down as her cousin disappeared down the hall. She had a glimmer of hope coupled with dread. Hope that Uncle Charley would lend her the money and dread what strings would be attached. He'd never done anything overt but she shuddered remembering the leer on his face last summer when she came out wearing a borrowed two-piece suit to their pool. She stood as her grinning cousin hopped down the hall.

"He said yes, or actually, he has a job for you so you won't even have to pay him back!" she cried.

"Job?" Cayley looked confused, "He's retired. What job?" Charles Wallace retired at 45 after making a series of fortuitous investments.

"He needs a maid. Remember Maria? She's retiring next month and he was just about to post a listing...I told him you'd be perfect," she looked happily around their apartment. "I mean, um, I'm sort of a slob and you really keep this place looking great, plus you do all the cooking, laundry...do I do anything?" she asked.

Cayley shook her head, "you provide the valuable service of making sure one of us parties and entertains boys," she chuckled. "Those penises won't take care of themselves."

"Damn straight," the girl laughed, "I could use your help in that regard, I mean, you don't have to fuck them, you could just give them handjobs, ever hear of a fluffer?" she chuckled.

Cayley shook her head, "It sounds easy enough, but a handjob will lead to them asking for a blowjob...and no way am I putting something that gross in my mouth. Then they'll tell me how good it would feel to put it inside...you know, just for a bit..." she said feeling that strange chemical thing again. "Anyhow, that's your thing. I'll focus on studying." She thought about being a maid and the idea wasn't half bad. She enjoyed cleaning and cooking. She liked things neat. She had a thought, "Oh. How much? I mean, did Uncle Charley say how much he'll pay me?"

Emily smiled, "A lot! $1,000 a week plus extra for events."

"Events? What events?" she asked but the thought of 12 weeks of work was almost the amount of the loan she'd applied for. "What did you tell him?"

Emily held out the phone, "That you'd let him know. Should I hit his number?"

Cayley held out her hand.

* * *

"Little Cayley!" Uncle Charley smiled at the girl standing on the porch, her suitcase beside her. "Or rather, 'Not-so little Cayley!'" he corrected himself, his eyes focussed on the large chest.

"Hi, Uncle Charley," the girl sighed as the man pulled her into a tight hug that lasted a bit longer than normal familial hugs. She had been bracing herself for his comments, leers, and frequent touches, but a thou a week is a thou a week. 'Does that make me a whore?' she wondered. He finally let her go and ushered her into the house.

Charles looked at his niece marveling that she could possibly have remained a virgin with all the horny college boys around her. He thought back to what Emily had told her and felt an anticipatory throbbing in his groin. She'd said that Cayley was a horny slut at heart and just needed the right man to open her up to reveal her true self. That she'd end up thanking him and her resistance was nothing more than a game.

"Come in. Let me show you your room," he smiled as they headed down the hall. 'This is going to be a great summer,' he thought, 'to be alone with the sexiest girl around.'

Cayley followed him, rolling her suitcase while looking around. The house was immaculate and she wondered what would be required to earn $1,000 a week.

"Here you are," he held out an arm. There are fresh towels in the bathroom, the sheets are fresh and your uniforms are hanging in the closet."

Cayley stopped and looked questioningly at her uncle. She looked at her jeans and tee-shirt, "Uniform? I can't just wear, you know, normal clothes?" she asked.

"Emily didn't tell you?" he looked pissed, "Of course, she didn't. I told her that I'd either pay $500 a week or if you agreed to fulfill a stupid fantasy of mine, $1,000 a week if you'd wear a French maid's costume. I actually went out and purchased a bunch of them when she told me you'd be thrilled...I'll kill her. You have no idea how much they set me back." he sighed.

Cayley looked at the closet. "Are they...?" After he nodded she went over, opened the door, and looked. There was a row of short black and white dresses...though calling them dresses was an overstatement. She pulled one out and held it up to her chest and looked in the mirror. She had one-peise bathing suits longer than this. She looked at her uncle and back at the mirror. "Um, I don't think this will cover my butt so you'd see my panties," she said softly. '$500 more per week so he can see her panties? Shit!' she thought.

"Well, about that," he said going over to the dresser, "No panties." He held up a tiny thong. "Look, I'm sorry Emily didn't tell you and if you don't want to, it's fine," he said sounding like it wasn't fine at all.

Cayley sighed, 'What the hell. He's seen me in the ridiculously tiny bikini of Emily's and it is $500 more per week...$6,000 for showing a bit of skin?' she thought. She went over, and took the thong from her uncle, "Go. I need to change. I assume you'll want lunch?" she asked. There was that stirring inside her again, but this time she avoided touching her nipples.

Charles had to adjust himself as he closed the door. It had been a fantasy of his for some years and when Maria said she'd be retiring, he wondered how to go about getting a replacement maid who'd make his fantasy a reality. It never occurred to him that Cayley would be the girl to fulfill that fantasy. He went into the living room and picked up the book he'd been reading before his niece arrived.

Cayley tried to pull down the frilly hem but her bare ass was totally exposed and all that did was expose her bra-covered breasts. She'd need a strapless bra with smaller cups. She was also aware that the top was translucent and her flesh-colored bra was clearly visible. It occurred to her that this was meant to be worn sans bra. On top of that, the thong wasn't very comfortable, cutting into her crotch and feeling strange wedged between her ass cheeks. At least her bush was trimmed so no stray hairs were peeking out. She gritted her teeth and headed for the door. 'In for a penny, in for a pound, as they say...or for $500...'

"Wow!" Charles stood as the girl came into the living room. "I didn't think they were that short, but I love it!" he sighed. "Turn around."

Cayley was blushing furiously wondering if it would be less humiliating being completely naked as he felt his eyes on her white ass-cheeks. She turned back, "Lunch? What do you feel like?" she asked before questioning the phrasing. She knew what he felt like having and sighed, "What do you feel like having for lunch?"

Charles sighed, "Um...it's not right. This is not supposed to be worn with a bra. I mean, I can see the bra straps which spoils the effect."

Cayley looked down in panic, "but..."

"I know. I'll tell you what, I'll make it $1,100 a week if you accommodate me on this." He saw her hesitate, "$1,200."

Cayley nodded and went back to her bedroom. 'This is going to be a long summer,' she thought. Pulling down the top on the outfit was easy and after taking off the bra and rearranging the top she moaned. 'Emily would be a better candidate for this. I never realized how dark my nipples are,' she thought. She might as well be topless as her creamy-white breasts and chocolate-colored nipples were barely hidden beneath the sheer material. 'Oh, hell,' she thought. 'You knew he'd get me to lose the bra sooner or later...hell, how soon before he wants me to do the housework naked. She remembered her mom telling her before she had her she'd always done the housework naked, but thought it inappropriate after having a kid.

Charles stood and nodded, "very nice. Ok, I was thinking a sandwich would be good. You'll join me, by the way. You might be the maid but you're family," he said as he headed for the kitchen.

'This might not be so bad after all,' she thought, 'no leering, no suggestive comments...though I hope there's a lock on my bedroom door.'

After lunch, Cayley did some laundry, vacuumed, and did light dusting while her uncle read his book. She'd expected something humiliating, but he checked her out periodically without making any moves on her.

The following two weeks were uneventful, a basic routine was established which allowed Cayley to relax. Her nipples seemed to always be sensitive and she spent more time washing her crotch every morning as it seemed to feel really good. She found the outfit was actually comfortable as it was a warm summer and the thin material and tiny garment were welcomed...except for the times she went to get the paper or the mail. She looked out to ensure no one was around before going out, but periodically a car drove by, slowing down to check her out. Then there were the deliveries and Uncle Charley expected her to answer the door every time. Well, not totally comfortable. She couldn't get used to the butt floss they called a thong. It was just a weird feeling.

Charles jerked off every night thinking about the nubile young girl...woman down the hall and even though Emily swore if he forced himself on her she'd respond enthusiastically, he couldn't bring himself to do that. He'd rarely seen any woman with such perfect curves in all the right places. Huge plump breasts, wide hips with a full ripe ass just made for fucking but he wasn't going to ruin the level of comfort she'd attained with her near-nudity. He lay there wondering if she'd go along for the next event.

* * *

"Morning, Uncle Charley. I made waffles, here's your coffee. Have a seat," the girl smiled.

Charles sat and looked at those perfect tits, unconsciously licking his lips. "Oh, by the way, did Emily mention I might need you for some events?"

"She mentioned it, what event?" she asked.

"Oh, good. I'll pay you extra, obviously, but tonight I'm having some guys over to play poker. You ok with that?" he asked.

Cayley looked down, "Um, wearing this? I don't know," she stammered.

Charles chuckled, "No...it's something else. First of all it's more of a barmaid's outfit, second, it's red which should look great on you...and, well...would you like to see it?" he asked.

Cayley nodded nervously. His tone wasn't as positive as he tried to make it, but she could always say no.

Uncle Charley came back with the tiny garment on a hanger. "Go try this on and, just so you know, you don't wear anything under it. Oh, and if you agree, I'd pay you $500."

"Nothing underneath? No thong?" she asked.

Uncle Charley shrugged, "It will ruin the effect. If you don't want to do this I have a girl who I normally call...no pressure. The guys like her, but I'd rather give you the money. Think about this, it's quite revealing but you're not there to have sex with anyone, and also, you'll probably never see these guys again."

Looking in the mirror she groaned. The money would help...help a lot, but could she possibly? If she dressed like this in front of the kids at school, they'd always look at her remembering, but as Uncle Charley said, she'll never see these guys again.

The tiny red garment looked like it was designed for an elf...a slutty elf. Chest exposed, just a lacy criss-cross strap that lifted her large creamy breasts making them jut unnaturally out. Below that was a tight corset with a tiny flare that mimicked a skirt just above her hips. All attention would be focused on her dark nipples and her almost black patch of pubic hair but there was nothing to be done about that short of shaving and that wasn't happening. She shrugged her shoulders and headed for the door.

"You look incredible!" Uncle Charley said. "The guys will love you, plus Cheryl makes a lot on tips when we have poker night here. You'll clean up." He looked at the girl wishing he were a different guy...a guy who'd force himself on her, but she wasn't just his niece, she was one of the sweeter people he'd ever met. What was Emily thinking and why would she want him to force himself on her friend?

* * *

"Get the door, won't you?" Charles asked. "The guys must be arriving." He watched the girl's incredible ass flexing as she trotted over to the front door. 'The guys are going to go nuts over her,' he thought, 'Cheryl's cute and all that, but her B cups couldn't compare to Cayley's Es...Fs? Fuck! And her ass...what I'd give to...' he sighed loudly causing Cayley to turn around.

"Are you Ok? That sounded bad," she asked as she reached for the door handle.

"No, sorry. I just realized I need to go to my room since I forgot my cash. Go on, get the door. I'll be back," he said.

Cayley opened the door and stepped back as five men stepped inside. All looked her over before putting out their hands and introducing themselves. She memorized their names, Moe, Derek, Vic, Lance, and Bobby. Uncle Charley told her they were good tippers and knowing their names should help.

Can I get you gentlemen anything? Moe, Uncle Charley says you like Jack Daniels, Derek you want a beer, preferably an IPA. We have Stone, Racer 5...Ok, Racer 5. Vic, a gin and tonic if I remember right. Lance and Bobby, single malts, Isley for you, Lance, Highlands for you, Bobby."

She smiled as the men all had pleased looks that she knew their tastes and went to get the six drinks. She knew Uncle Charley liked mojitos and had a pitcher in the fridge at all times.

The men seated themselves around the table, looking over at the girl whenever she went by, but when Charles asked she put on some music and she had to bend over to access the controls, the room went completely silent.

Cayley felt more exposed than she'd ever in her life as she bent over with her ass up in the air, her aroused pussy right there in front of six pairs of eyes.

Charles chuckled, "Now you can see why I've been staying at home a lot. Between golfing or tennis and the views I have here at home...well, you get it," he laughed.

Cayley stood up blushing as the music came on, "Can I get anyone anything else?" she asked sweetly, "Something not down at floor level? Or did you want me to bend over again?"

"Yes, please," all six men said at once.

"I was kidding, but..." she saw their eager looks, "ok, but this is the one time," she said softly. She turned, opened her stance, and bent over, looking at the men from between her legs. 'If Emily could see me now,' she thought. Three of the men were doing something with their crotches as she stood back up. "Ok, let me know if you need snacks or more drinks," she said.

They kept her busy all night and as they had more to drink, the touches began followed by playfully pulling her onto their laps. Cayley felt slickness between her inner thighs and had a feeling she'd never really felt before...almost regret when they each let her go after just a few exploratory feels. On one of her trips to the kitchen, she looked in the hallway mirror and was shocked to see her dark hair was a mess, red marks on her breasts and ass. Even Uncle Charley who'd assiduously never touched her or made any lewd comments joined in. The other shock was how she reacted. Never once did she slap their hands away or admonish them, rather she teased the men by dropping things on the floor and either squatting down or bending over slowly to pick things up. And her breasts. She found the more she rubbed them on the men, the happier they were.

barkirk
barkirk
3,036 Followers