Satisfying the boss

You walk up the tile stairs. The restaurant is in its own building and apparently Ruth has an apartment upstairs. You unlock the door and walk in. Only once you're in does it occur to you that Ruth could have a husband or vicious guard dog. But the apartment is quiet and empty. The furniture looks a little outdated, it's all red and brown, overstuffed couches, there's even beige carpet. Impressionist and modern art paintings are on the walls in gold frames.

"Everywhere on this stupid island is like the 1990s!" your sister whines, picking up an old corded telephone.

You shrug. "Hey call home and say we'll be here for a while," you say.

"Yeah then we'll watch Seinfeld," your sister jokes, "How do you work this thing?" With a surprising amount of difficulty, the zoomer dials the touch tone phone to call your house across town and tells Ellen that she's at a job interview and doesn't know when she'll be back, but you're with her. You keep hearing your big sister's whiny voice buzzing over the phone and your little sister answering. "No he's not being a pervert. No the interview is with a lady, I'm not gonna get ****. Calm your tits."

You can hear Ellen screaming over the phone but you just laugh. Katy says goodbye and hangs up. "Come sit on the couch with me," you say.

Katy joins you on the tacky leather couch. At least it's comfortable. "I think I've lost my mind. I actually like it here."

"What, this apartment?" you ask.

"No, this whole dumb island of perverts," she says. "I've never done anything like this. And nobody back home will know what I do here?"

"Nope," you say, reassuring her, "They take everybody's phones, remember? Going back to 1990s tech has its advantages."

She smiles. You watch a few shows on TV (at least Ruth has a modern flat screen) to kill time. Eventually your sister says, "You have to satisfy Ruth huh? Maybe you should jerk off first, so you don't cum right away. Like earlier..."

You both blush. She's openly referring to the blowjob she gave you. Or that you and Heather made her give you, but clearly she didn't mind. "Hey I lasted a few minutes," you say.

"Ruth wants some amazing sexual experience, Romeo," she says, then reaches for your cock casually, "You'll have to do better than a few minutes". You're not one to object to a casual handjob from your sister so you let her start to stroke your shaft.

This feels great. You're naked on the couch and her firm hand is sliding up and down on your dick. You reach over and play with her handful-sized tits and she doesn't object. You kiss her on the lips and she sighs happily, kissing you back softly. Her hand squeezes your cock as she strokes you.

"Does it feel okay?" she asks, breaking the kiss.

"Sure," you say, "You like touching my cock huh?"

"Yeah," she says, blushing badly, and tightens her grip. "I know Heather's your girlfriend but I want to be your..."

"Perverted sex ****?" you say on a hunch.

She moans in surprise. "Y-yeah, something like that," she says, "Just for the summer of course."

"Of course," you say. You feel like the luckiest bastard on the planet to have your cheerleader sister volunteering to be your sex ****. Your cock is up to its full ten inches now and her hand feels so small against it. You can't wait to put this inside Katy's pussy, to take her virginity, smash that hymen... but now is hardly the time. She masturbates you and it feels so nice and comfortable, like this is the sort of relationship you were meant to have with your little sister.

"Fuck that feels good Katy," you say as she strokes your big dick, "I'm gonna cum... let me shoot it on you."

The old Katy would have slapped you, but now that you're acting confident and make her reveal her truth self to you, she doesn't resist as you stand up in front of her. "Keep stroking it!" you yell in annoyance when she stops. How does she think a dick works?

"Oh, sorry!" she says, grabbing your cock with both hands and pointing it at her nice tits as she strokes. You groan loudly and cum, painting her tits with sperm, then grabbing your cock and letting ropes of jizz land on her stomach, and then her pubic mound. She looks at you intensely as you cum on her pussy, the next best thing to cumming on her pussy.

"Hey, save some that for me or you'll both be unemployed!"

Your heads swivel around to see Ruth in the doorway.

"Hey don't worry, my brother can cum lots of times! Just look at how much sperm he makes!" your sister sells your sexual prowess like a used car salesman **** to hit a quota, gesturing to all your cum on her tits, stomach and pussy.

"Oh shit! Uhhh, hey why'd you get cum on me, asshole?" she adds, only belatedly realizing she shouldn't casually demonstrate she's having **** with her brother. Oh yeah, that's a good point, you hadn't even thought about how **** might shock people here other than Heather as much as it shocks people back home. Just because they walk around naked doesn't mean they're okay with ****.

Ruth laughs. "Oh don't worry, my little perverts. Your secret is safe with me. And lucky for you I find it sexy."

You breath a sigh of relief along with your sister. Ruth plops down between the two of you on the couch with a thud that indicates she's had a long day at work despite her playful attitude. "Okay kiddos, here's the deal. I really don't just hire hostesses out of the blue. We're already fully staffed. And everyone on staff will be pissed at me for letting you skip the line a top job. You should start out being a bus boy."

"But I'm a girl!" Katy says, pointing at the evidence to support this: her tits and pussy. You and Ruth laugh at her bluntness.

"Good point," Ruth says with a grin, "If I take you on as a hostess, you actually have to bring in customers. Sell them on expensive wines and the evening's special. Make it worth my while. And you can't screw up and create problems. If you mess up anything, even fold a napkin wrong, I'll punish you. Except I'm too busy for that, so I'll have your brother punish you. Can you handle that?"

"Y-yeah," Katy says, surprised, but sounding intrigued as well. "I mean, yes ma'am."

"And you," Ruth says, turning to you, "You have to really punish her."

"I can," you say. You've never punished a woman in your life, although there have been times you would have liked to punish Katy quite a bit for being annoying as hell. If you're being given an excuse and she's okay with it, you're all for this. "I'll whip her into shape."

Ruth grins. Your sister looks down in embarrassment, but she doesn't object.

"And finally, if I'm going to give your sister such a cushy job, you have to please me too, like I said," she stands up naked in front of you, "You don't mind sharing your brother's dick with old Ruth, do you Katy?"

"N-no," your sister says, "He's very good!"

Ruth laughs. "I know, I've had a preview. But I'm much more demanding in private. Or just with little sister watching. You do want to watch, don't you Katy?"

Your sister nods eagerly. "You have to do two things tonight if you're sister is to get the job," she says to you, "You have to give me a powerful orgasm just through penetration, and cum inside my womb."

Ruth walks into her bedroom. "Her womb?" you ask your sister in confusion.

"It's where babies are made," she says.

You roll your eyes. "Won't that hurt her though?" you ask.

"Sure would hurt me," Katy says, "But she's old and shit. Maybe it's what she needs to get off anymore."

"Get in here, kiddos!" Ruth yells impatiently. You and Katy run into the middle-aged woman's bedroom. She's twice your age and makes you feel so young, but you're all adults here.

Ruth is on her bed, posed seductively on her side with her big, mature breasts sagging only slightly. Her skin is freckled but nice in the lamp light. Her pussy is totally hairless. You realize you have to actually satisfy her and make her orgasm, not just enjoy yourself and cum all over the place, which has been your experience with women so far, if you're being honest. It's a little intimidating, but you've learned lately that if you act confident and do your best, things seem to work out.

You get on the bed, which feels very indulgently soft. The silks are sheet and there's some kind of mood music playing, smooth jazz. Corny music normally except now it feels nice. You crawl between Ruth's legs and **** her thighs apart, eager to really see her pussy. She's shaved bald like most women here. Her labia lips are a little stretchy and her skin has a nice bronze all-over tan.

Your experience eating pussy is limited, but you're into this, even if she's older than your mom. Or maybe because of it. You push your tongue into your boss's vaginal opening and like what you taste. This is a mature lady. She's very wet and her cunt welcomes your tongue.

Your sister is laying on the bed watching you lick Ruth. "Do that to me soon..." she says, and this horny thought only makes you lick your boss harder, giving her pussy a long lap with your tongue as you work your way up to her clit. You flick it back and forth with your tongue and suck on her clit, genuinely enjoying this, especially as it's making Ruth moan. She grabs your hair and yanks on it as you pleasure her, keeping to slow, rhythmic licks since you read online that's what women enjoy. Amazingly the internet advice seems to be true as you give Ruth an orgasm in no time.

"Well that's a good start," she says, "But not nearly enough. Get that big dick inside me!"

You stand on the bed proudly, showing off your cock. Not needing to hide your incestuous urges anymore, you say to Katy, "Kiss it, sister. Get it fully hard."

It's pretty darn close to the full ten inches, you just want your little sister to kiss your dick. Katy doesn't hestitate to lean in and kiss her big brother's cockhead, planting a big loving smacker on your penis.

You hold yourself over Ruth, looking at her sexy middle-aged body. "Should I use a condom?" you ask.

"No!" she says, "Don't even mention that word."

Well, you're not going to argue with bareback sex. "Guide me in, Katy," you say, wanting to include your sister of course. You feel her tight hands around your shaft, pushing you into your boss's pussy.

You're on top of Ruth in missionary position, you suppose this is a boring position to most people but you don't agree, you want to look at a woman's tits and face while you fuck her. You press into your boss's cunt and her pussy walls are so tight around your shaft. She's onto something with this no-condoms-ever thing, and everyone's tested for diseases before they're let in here.

Katy is still guiding you in. You could manage on your own but this feels good. Soon you're most of the way inside Ruth and kiss her confidently on the lips. Katy leans in and you're having a sexy three-way kiss with your sister and your boss as you root around in Ruth's cunt with your big cock. That was smart to have Katy make you cum earlier, you aren't even close now.

In your horniness at the nasty kissing, you greedily push your cock deeper into Ruth until you bump up against something.

"Oh! You gifted boy! You're there!" she says, "That's my wombhole!"

This is kinda weird, but sexy. If Ruth actually likes this you are all for it. You grin and press your cock against the middle-aged woman's cervix, pleased with yourself for being so big that you can reach this extremely private part of a lady. Your sister crawls down to watch as you grin and press your cock hard against Ruth's tiny inner hole, making it part and give up this lady's last secret.

Ruth grunts as your cock spreads her cervix. "Do it! Fuck her womb!" your perverted little sister says.

You give a confident grin and thrust forward with all you've got. You feel something very tight around your cockhead and then it's inside something small and warm. You've penetrated Ruth's cervix.

You look to your boss for signs of distress but her mouth is agape with pleasure. You bottom out with your balls slapping against her bald lower pussy, fully inside a woman for the first time in your life. But hopefully not the last.

You carefully pull out and penetrate Ruth's cervix a few more times, fucking her most intimate place like she wants, and she's screaming with pleasure and a slight amount of pain. Your sister climbs up and is sucking on Ruth's titties as you pick up speed, fucking her outer pussy now. It's still tight enough to please her. You fuck her hard, harder than you've ever fucked a woman before, making the bed shake and Ruth moan so loud you're sure the workers can hear her below in the kitchen, where they're closing up for the night. You doubt it's the first time they've heard their boss taking cock.

You thrust your cock in and out of Ruth's pussy hard for a few minutes. Your sister alternates between sucking her nipples and making out with her. You brush your cock against her clit as you penetrate her deep, occasionally exploring her womb, but mostly focusing on hard fucking of her pussy. You hold back your own orgasm until the hard bareback sex has Ruth screaming out her own, cumming hard and soaking the sheets with her feminine juices as she sprays you, your sister, and everywhere else.

"Now!" she says as she rides her orgasm, "Cum in my womb, boy!"

You can't refuse a lady so you penetrate her deep again, thrusting confidently now to part her cervix and press your cockhead into her womb. You press your body against hers with your cock all the way inside her as you explode, shooting ropes of cum hard into her womb. You can feel your own sperm filling up around your cockhead as you fill her most private place with your hot jizz. You confidently **** your tongue into her mouth as you cum, showing your power over her for this brief moment.

You lay there for a while, holding yourself up just enough so you don't hurt her, then slowly pull out. Ruth is laying there mumbling in senseless pleasure. You're still in a horny daze yourself and grab your sister's hair. "Clean my cock," you order her.

Your once-bitchy little sister seems off in a strange submissive space as she eagerly licks your cum and Ruth's feminine juices off your penis. She's truly cleaning your dick like you ordered, your sexy cheerleader sister is tonguing you everywhere to get your cock totally clean.

Meanwhile Ruth is doing some rocking exercises next to you on the bed, holding her knees and tilting herself onto her back rhythmically.

"Increases the chances of impregnation even further," she says.

"WHAT?" you ask.

"Oh calm down, there's no child support payments here," she says, "I just want a baby for myself. You won't have anything to do with it. I just needed your gifted sperm."

You relax a little bit, but Ruth could have told you this ahead of time. Still, she's 50 and while you're clearly not a fertility expert in the medical sense, you think it will be quite hard for her to get knocked up, even with the cum delivered to the babymaking factory so expertly.

"So do I get the job?" your sister asks, interrupting your thoughts.

Ruth laughs. You do too. You'd forgotten why you were fucking your boss.

"Sure," Ruth says, "As long as your brother does his part, you're my new hostess, Katy. Congratulations."