Looking for work

You head upstairs just as Penny's shift ends and she clocks out, apparently really not bothered that you jerked off in front of her. It feels weird to go naked into your apartment, but apparently that's just what one does here. Your sisters are out but dart into their bedroom when you come in. You wonder what they think the point of that is, if they're going to be naked all summer then you and every other dude in town will be seeing them naked. But at the same time you're glad they're embarrassed, you wouldn't them to be immodest sluts.

Your mom comes out of her room, totally naked, no modesty there apparently. It still seems weird, even though you logically know that none of you can wear clothes until summer's over. You try not to be obvious as you look at her firm tits and shaved pussy. She's your mom - what's wrong with you?

"So how are you liking it here so far?" she asks you.

You booked us for the summer in a nudist town without telling us, you think, how are you supposed to be "liking it"? It's actually a good question - how do you balance your annoyance at what your mom did with your own excitement to be in such an amazing place, and all of that against your humiliation to spend your summer naked around your family and complete strangers? But you can't give your mom an honest answer, of course, with all of that talk of how horny you are at the possibilities.

"Uhhh," you say lamely, "It's a lot to take in."

"I bet," she says, "But it only seems that way because I raised you in such a conservative environment. Nudity is no big deal to mature adults."

If you say so, you think, careful to look at her face. You wonder if you looked at her body if she'd still be preaching about how nudity was no big deal to mature adults.

"So have you gotten any leads on a summer job?"

"I just got here," you point out, trying not to act annoyed. Mom is paying for this whole vacation, all she asks is that you get a job to cover your spending money and whatnot. But does she have to ask so soon?

"Okay," she said, "But you're a grown man now. I do expect you to at least get a part-time job. Why don't you go look around now? You should at least get used to walking around town and figure out where everything is."

It's not terribly unreasonable, you suppose. But you notice she's lecturing you sternly while your little sister, who is also an adult now, relaxes in her room. You wonder if Katy will work a single day this summer, or if Mom will get on her case about it even once, despite how she's riding you to get a job from the moment you finished unpacking. Oh well, no sense fighting a losing battle, you figure.

"Okay mom," you say, rising up. Once again you feel the urge to get dressed... but yeah, you can just walk out naked. You comb your hair at least and put on some fresh deodorant, noticing the girls watching you from their cracked bedroom. "It's safe to come out, I'm gone!" you yell in annoyance. As brash and intrusive as your sisters are, you're surprised at their sudden modesty.

You suppose being **** to go naked will do that to girls though...

You put on your shoes (at least they're allowed) and head down to the street. You still have a lingering suspicion that this is some elaborate prank and as soon as you turn the corner there will be a crowd of reasonably attired people who will look at you like you're a freakish deviant. That feels logical, right? How can people actually be okay with walking around naked all summer?

It's that strange time between late afternoon and early evening as you walk outside onto the quiet residential street which your apartment building fronts. Standing strategically behind the front wall at the sidewalk, which is waist-high, you look down the street and see naked people walking toward the main drag. They're older and not of much interest to you, but at least it confirms that this whole day hasn't been some weird fever dream and you probably won't get arrested if you go for a walk without any clothes on.

You like walking around town. Even back in your dinky hometown, where you were hoping just to see a chick in maybe a tube top and tight shorts, you walked around the neighborhood when you had nothing better to do, looking for something interesting. If you're guaranteed to see naked women you're going to be doing a lot of walking around town this summer.

You walk to the central street which has a sort of European feel to your decidedly midwest American sensibilities. Stately apartment buildings flank the boulevard with shade trees down a central median, with cafes or small retail stores on the ground floor. But you're more interested in the naked women. They're of all ages but plenty are under thirty. Most everyone is thin and athletic or at least not too bad looking. You suppose nobody would come here if they were ashamed to walk around naked.

Most of the women are shaved bare. Walking around shamelessly letting everyone see exactly what they look like naked. Every intimate detail. You can't imagine how women could do that, but then you're walking around naked yourself and don't seem to be dying of embarrassment. You really can't believe the women here though. One catches you looking at her pussy and doesn't even seem to care.

After ogling naked women for a half hour as you walk, trying not to be too obvious about it, you remember you're supposed to be looking for a job. Back home you worked in a grocery and that was lousy, even for a part-time job. You apply for a few jobs at places like the hardware store and an ice cream parlor, just filling out applications naked which is weird, but the applying part is as mundane as back home. You don't think any of the places are serious about hiring anyway.

Then you go into a restaurant in a corner building. It's a seafood place, which only makes sense since you're a block from the ocean, and it looks a bit upscale. It's called Ruth's and the owner is actually named Ruth and calls you back to her office for an interview on the spot after you ask the naked hostess if they're hiring. Ruth looks to be a little older than your mom but she's quite hot, in your opinion. She has curly dark brown hair to her shoulders, she's short but curvy with large natural tits and once again a shaved twat. Her skin is freckled but not too wrinkly. You wonder if you'll ever get used to seeing people naked as soon as you meet them. Her office is pretty tiny but you suppose that's just how it is in a restaurant.

She asks you about your experience (none that's relevant) and is amused to find you just moved to the island that day. But it's not like she offers any advice or lets you cover up with a towel or something, the interview just goes on enough to clarify that you probably wouldn't make a good cook since you have no skills in that direction (your family is kind of traditional in that regard - the women always cook for you and you'd struggle to make grilled cheese).

You think maybe Ruth will offer to let you be a bus boy but then Ruth asks, "So how big is that cock? It looks pretty big already."

You blush badly and look down, seeing you're already semi-erect just from the tension of the interview and being able to see Ruth's body. Then you realize that in addition to making you uncomfortable, Ruth's question is flat-out inappropriate by any standard. And yet... she asked it with such confidence, like it was a totally normal thing to say in an interview.

"Uhh, ten inches, ma'am," you say awkwardly, still somehow in interview mode where you're trying to make a good impression.

"That's very impressive, if true," she says, "Prove it."

You're in shock by all of this but start stroking yourself. You're not sure if you're intimidated, eager to impress your interviewer, or excited to jerk off in front of a woman for the second time in a day. Maybe a bit of all three.

You get fully erect and keep stroking yourself slowly, unable to stop now. Ruth is looking right at your cock.

"Very impressive, and to think I was going to make you a bus boy," she says, "How about being a waiter?"

What kind of restaurant is this, you wonder? But then again waiters are usually attractive, even male waiters (not that you care, but you've noticed).

"I guess..." you say awkwardly.

"Let's do the rest of the interview with you inside me," she says bluntly, putting her feet on the chair she's sitting in and spreading herself obscenely for you. "I find guys always give honest answers when they're having sex."

What is happening? You shake your head as if to snap yourself out of a hallucination, but she's still spread wide and now pointing to her pussy like you're a moron for not already being inside her.

You've only had sex once before, awkward lights-out sex with your girlfriend after senior prom. And she was a little chubby to be honest, 50-year-old Ruth is sexier, amazingly. This woman is in great shape. You're horny as hell and aren't going to pass up the most casual sex imaginable.

You walk across the tiny office in one stride and lean over Ruth's chair, pressing your cock against her vaginal entrance. You half-expect her to laugh at you for taking this seriously, or yell "****", but she just looks at you like you're a country bumpkin for not starting already. So you push your cock into her pussy and find it wet and eager for you. You groan and start to fuck this strange, slutty woman, loving the feel of her mature pussy. You hold yourself up with one hand on her desk and grope her tit with the other.

"So how would you like being a waiter? You have to be nice and cheerful, the customer is always right, you know?"

What, she's really going to interview you while you fuck her?

"Uhh sure, I'm a nice guy," you say, "I like talking to people. I don't mind explaining the menu or whatever."

You're much more focused on enjoying her pussy. She's taking your length much more easily than your first partner, so you push deeper and deeper. Her wet cunt takes your length eagerly.

Ruth asks you boring questions about if you can be on your feet for up to an eight hour shift and if you can sell the day's specials. It feels hilariously mundane since you're inside her pussy as she asks, enjoying her mature body with every thrust. You couldn't care less about the job but you mumble the correct answers just so she lets you keep fucking her.

You press deep, amazed that she can take your entire length, although you're pressing hard against her cervix. She's moaning loud though, you're sure her employees can hear. But you don't care. You forcibly kiss her on the lips, pressing your tongue into her mouth as you explore her pussy with your cock.

You break the kiss and look at her sexy body as you fuck her cunt. You just met this woman who's older than your mom and you're using her without a condom. But that feels like the only way. Her pussy is so warm and wet, you needed to feel it. She asks you if you've ever stolen from a business and you grope her tits and thrust deep again. This question is so ridiculous. You pull out your big cock and slap her clit with it, because you can, then answer that you're not a thief.

You push your cock back inside Ruth and fuck her hard, pushing her into the chair against her desk, ramming her pussy with your cock. She asks more questions and you answer automatically, not paying any attention to her words. Her pussy grips your cock hard, she's tight despite her age. You press in deep, feeling her cervix again. You just met this woman and are feeling her most intimate, private place. You realize you've wanted to do this to every older, condescending woman you've met your whole life.

You use her hard, making her love it and moan as you use her body for pleasure. You push deep again and start to cum hard, not even thinking about pulling out as you fill this woman's pussy with your sperm. You realize she's cumming too, squirting her juices against you as you cum inside her. You keep your cock deep in her, letting all your juice flow into her, holding her as you use her as a cum dump.

"So would you like the job?" she asks.

You look at her in confusion.

"Answer fast, I don't like to wait. Do you want to be a waiter here?"

"Uh, sure," you say. You pull out of her pussy with a wonderful slurping sound. There's some cum on the tip of your cock so you wipe it off on her tits.

"When do I start?" you ask with a grin.