Josie's Summer Vacation - Cover

Josie's Summer Vacation

by Mushroom

Copyright© 2020 by Mushroom

Erotica Sex Story: When an old friend invites Josie and 3 of their friends from college to visit for a week on the California Coast for a "Hen Party", none of them have any idea that things will change drastically.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Drunk/Drugged   Lesbian   Cheating   Gang Bang   Anal Sex   Cream Pie   Exhibitionism   Masturbation   Oral Sex   Pregnancy   Voyeurism   Big Breasts   Porn Theatre   .

It had never been my intent to hurt my husband. I looked across the bar at the 4 guys sitting there, and knew before the night was over I was going to be fucked by each of them. And it had all started so innocently.

Samantha, one of my friends from college called me up one day and said she was having a get together for “the girls” at her beach house in Santa Monica and wanted me to come. It had been at least 7 years since we had all spent any time together, and it sounded like fun. I talked to my husband that night and he said he had to go out of town that week on business so I should go ahead and go.

So I called Sam the next day and then arranged to take a week off work. And getting a new bikini and a little black silk dress that clung to my body quite nicely I took her up on her offer. And two weeks later I was getting on an airplane and flying to California.

Sam had done rather well for herself, becoming a talent agent representing actors and actresses in the movies. In addition, she had a nice and well-connected husband, so she seemed to be living the dream. When I arrived at the airport she was waiting for me and greeted me with a big hug. And right behind her was Kristen, another friend that I hung out with and we exchanged a hug also.

Arm in arm we left the airport and headed to Sam’s BMW. As we were getting in Kris giggled and said we seemed to be the center of attention from everybody. Maybe because it was because Sam was so tall, or because Kris had such long beautiful hair. Or maybe it was because I was so short. Of course, it could also be because Sam’s skin is incredibly dark and smooth, and Kris is a drop-dead gorgeous Chinese girl. While I am a rather plain white-bread WASP. With a slightly large nose, plain features, and nothing special going on in the body department other than a nice rack.

The first night we sat around watching a few movies and sipping wine as we caught up on the last few years. Kris was telling us about her last lover, who she had broken up with the month before. “Oh, she was pretty good, but so clingy I could not take her petty jealousy every time she saw me flirting with a customer. But it was not really flirting, part of the job was complimenting them on how good an outfit looked on them.” Kris worked at a high-end boutique on Rodeo Drive, and had never made it a secret that she was a lesbian.

In fact, my first experience with another girl was a drunken night with Kris. And then later there was another one with Sam, where we just held each other as we masturbated together one drunken night. It was sexy, and a lot of fun. But even then I knew I would never really swing that way. I simply loved penis to much to ever give it up for pussy. But it did not stop Sam and I doing it again a few months later, and Kris and I several additional times as well. But Kris and I actually were occasional lovers, with Sam it was more like we were masturbation buddies.

Sam told us as she took us to our rooms that the other 2 girls will be arriving the next day, and we could sleep in as she went to pick them up. “Oh, and you can each have your own room tonight, but tomorrow you are going to double up with somebody. You can decide now or in the morning, I will leave that all up to you.”

I sat on the patio off of the room and had a last smoke before heading off to bed. The night air feeling good against my skin as I sat there in just my bra and panties, listening to the surf in the background. I wobbled a bit when I stood up, and realized that each of us had killed at least 1 bottle of wine, and part of another. And I could feel the room spinning as I laid down in the king-sized bed and drifted off to sleep.

I got up the next morning and headed down, and saw Kris in the dining room eating breakfast. “Heya there Josie! Welcome back to the land of the living. I made you some too, it’s in the microwave. Just zap it a bit and it should be good.” I went in and looked, an omelet and sausage, she remembered. 30 seconds was about right, and with a cup of coffee in the other hand I sat next to her. “So, what’s new Pussycat?” she said, with a grin on her face.

I groaned. “Oh please, don’t start that again Kris! I keep telling you I was not named after a cartoon character, but from a character in a book.”

“I know, you were named after a vain, jealous bitch who tortured another girl out of jealousy.”

“Well, only indirectly. My mom used her name, only because she loved the book Anne of Green Gables growing up, and loved the name. I like to think I am nothing like Josie Pyle though.”

We chatted a bit more as we ate, then sat in the living room sipping coffee as the two of us caught up a bit more. “Seriously, you are trying to be a mommie?” she said, incredulously.

“Uh-huh” I said as I nodded. “Jeff and I decided that we are secure enough in our jobs that the time is right. I have this month and one more month then I am tossing out my pills. So hopefully around this time next year we should have a kid, or one about ready to pop.”

“Better you than me girl!” she said, and shuddered. “While I like kids and may someday adopt if I meet the right gal, I have absolutely no intention of putting myself through that. I guess I’m just one of those gals that has absolutely no maternity instinct like so many of you breeders have.”

We both chuckled, and in the almost 10 years since we had been short-term lovers she loved to tease me like that. We both knew it was nothing personal, just her being the outrageous Kris. About that time we heard Sam pull up and we went outside to greet the new arrivals.

Lois was another friend, and probably closest of all of us to Sam. Much more of a coffee and cream complexion than Sam, she had a booty and boobs that would not quit. Melanie however was a bit of a shock.

I had not seen Melanie since I graduated, and had never been all that close to her even then. She was 3 years younger, a Freshman when I was a Senior. And while I was flirty and a bit of a party girl, Melanie was shy and quiet. Short bangs and glasses along with almost frumpy dresses or sweats were my memories of her.

But Kris squealed when she walked in, and ran to give her a huge hug and kiss. I greeted Lois warmly, we were often going to clubs together back in the day, and even had some shared car dates and would have unstated competitions to see which of us could have our date orgasm first. Or see which of us could get our boyfriend of the time to give us an orgasm first. And a couple times went on dates by ourselves.

“Well girls, tonight we are going out to eat at Rococo’s, a seafood place not too far away. After that we are going to the Red Room, a club on Sunset. And after that, we will just see. I already have a limo reserved, so feel free to party and drink as much as you want.”

We sat around and since I needed more coffee I asked if anybody else wanted some. Melanie said she would love it, so I returned a few minutes later with a cup for her and a plate with some sweetener packets and some creamer. She thanked me and I took a seat on the floor in front of the couch across from her, using the coffee table to rest my cup on.

Of the 5 of us, Melanie had changed the most. The shy geeky almost dyke librarian look was gone, replaced with something completely different. Still slender with breasts that were barely a B at most, her light brown hair was now past her shoulders, and had green and blue streaks. The glasses were gone, and I realized her brown eyes had blue contacts in them. And the light blue dress she had on was on the sexy side, very unlike the frumpy ones or the sweatshirt and jeans she wore in college.

Lois had the most mundane of all of our lives. After graduating she had gone home, reconnected with an old boyfriend and gotten married. She was a happy housewife now, with 2 kids. Melanie told us she had moved to Florida, and was involved in an Internet company down there. We chatted and after finishing a light lunch we tried to decide who would pair up with who for the night. In the end the 4 of us drew cards from a pack that Sam pulled out, saying that the lowest and highest card that Lois and Melanie pulled would be paired up with the lowest and highest cards that Kris and I pulled.

That was how I ended up sharing a room and bed with Melanie. I helped her bring her luggage into our room and showed her where everything was. She was a bit taken aback when she saw there was only a single queen sized bed in there, but I told her the other room was the same. I admired her outfits as she hung them in the closet, and when she took off her dress to put on a large sweatshirt for lounging I realized she only had panties on under and no bra. A tattoo of a smiling sun was on her left shoulder blade, and when she turned around as she pulled the sweatshirt down over her head I saw a small devil with a pitchfork on her left hip. And her nipples and navel were all pierced.

She sat on the bed and pulled out her laptop, and said she needed to catch up on some emails while she waited. But when she realized we did not know the password for the WiFi I offered to go get it for her. So I went to ask Sam, and after she told me I grabbed 2 more cups of coffee and went in to tell Melanie.

The smiled and thanked me for the coffee and after she got connected she sat on the bed with her laptop between her legs as we chatted. We chatted about many things, and at the same time she occasionally would type things into her laptop. I asked her why she was not pursuing her career, as I remember she had been a business management major in college.

“Oh, I am Josie. You see, I am one of the partners in JDJ Entertainment. There are 3 of us that run the company, and we each have our own duties. Mine is talent procurement, office management, and human relations.”

At this she got off the bed and went back into the closet and pulled off her sweatshirt, and pulled on a short pink shirt with a cat on the front that barely reached below her breasts. And wearing just that and her panties she then got back onto the bed and continued typing a moment before she turned her attention back to me.

When I asked how many employees she had, she closed her eyes for a moment. “Hmmm, there are the 3 of us, then Josephine the receptionist. Then there is Hugo and Frank, they work in the warehouse doing shipping and receiving and inventory management. We have maybe 40 others that are independent contractors that we bring in, maybe 10-20 at a time depending on what we need that particular week.”

“Wow, that’s not bad Melanie! What is your gross, may I ask?”

I saw her lick her lips, and raise her arms high over her head and stretch, the crop top rising up so high I could saw the bottom of her breasts peeking out before she lowered her hands and typed again. “Oh, before taxes and expenses we gross around $3.5 million per year.”

“Holy crap, and you have only been doing this for 4 years? And after?”

“Ohhh, around $2 million net I would say. I clear just a little over $300k personally, the rest we all roll back into the company. Next year we plan on buying a new company complex, right now we are renting a warehouse in an industrial area. But we have our eye on a nearby resort that closed up after it got damaged in a hurricane. It was a small resort hotel, kind of out of the way that was old and outdated. But it’s remote, and think it will suit our purposes. The beach is almost a mile away, but it has a 50 room hotel, a bar-restaurant and 2 small convention halls. Plus some other outbuildings like a workshop and warehouse. We are going to gut part of the hotel, and set it up as offices and apartments. And other uses I’m sure we will be able to find.”

As she was finishing saying that, she leaned way forward, looking at something to the side. I could not help but notice that her top pulled down away from her body, showing me her small but firm breasts hanging down under it. I quickly looked away, and asked her if she wanted more coffee. She said no, so I said I would get some more and go for a walk on the beach for a bit.

I walked the beach for maybe 30 minutes, having 2 smokes and wondering at what Melanie had told me. She was so completely different than when I knew her in college, I would not even recognize her if I met her on the street without being introduced. I went back to the beach house and saw Lois outside sipping a coffee. I refilled my cup and joined her, and we started talking quietly.

After about 40 minutes, she smiled and said she was glad that I had ended up teamed up with Melanie for the stay. “What, I thought you liked her?” I said, more than a little puzzled. “You two seemed to spend a lot of time together during my last year.”

“Josie, you remember what I was doing for money then, right?”

I sipped my coffee and nodded. “Yea, you worked at ‘White Satin’, the titty bar on the other side of town.” I remembered because she had me drop her off and pick her up there occasionally. I even went inside and watched a few times as I waited for her to get off. Lois onstage was Ebony, a girl that quite a few of the guys lusted after. And maybe even some of the gals.

She took another sip of her coffee and nodded. “Right after you graduated, Melanie wrecked her car and needed money fast to get it fixed. So I got her a job there.”

“No, wait, Melanie became a stripper!” I was flabbergasted. “I really find that hard to believe. Really?”

“Oh yes, she did become a stripper. Adopting the stage name of ‘Josie’, she quickly became the most popular girl there. I did good, I maybe cleared $100 on an average day, as much as $300 on a great one. But I also had strict limits. I followed all the rules, hands only on hips and sides. No excessive grinding, no private parties, I was only in it for the money I needed for college.” She took another sip of coffee and thought for a moment.

“But Melanie there, within a month she was doing private parties, and on more than one occasion in the champagne room I saw her allowing guys to go beyond what was allowed. And on more than one occasion she would have to go immediately into the dressing room and change because the guy had messed up her outfit.”

I was stunned, and Lois just gave a rueful smile. “It was about then I was sorry I had allowed her to talk me into getting her the job. I’m not sure how experienced she was when she started, but by the time I graduated I had found out she was also on a few escort sites in the area and was probably making close to 6 figures a year between the club and her side dates. I lost track of her after I graduated, Then one day I was doing a search for old friends and found she was involved in JDJ Entertainment.”

“What exactly is JDJ Entertainment? She told me it is an internet company.”

Lois giggled softly. “Yea, it is. ‘Josie, Doug and Jack Entertainment’ is what it stands for. Honey, JDJ is a porn company. Josie and Jack were their original stars, with Doug and Jack sometimes swapping who was her costar and who was filming. They shot a series of ‘Road Adventures’ around the panhandle, generally involving some random guy picking her up in a ratty motorhome then after fucking her senseless then dumping her on the side of the road nude.” I gasped softly.

“They made maybe 5 or 6 like that, and got popular enough that they first hired other guys to fuck her, then started doing different things. Like meeting her drunk on the beach or dragging her into an alley behind a bar or club. Then they got even more popular and started to hire more girls so she faded mostly into the background.”

“And she has been doing that since she graduated? Did she even graduate?”

“Oh yes, she graduated. She met them afterwards, then got into that business. We reconnected about 2 years ago, and she does seem happy. She said her intention is to keep doing it until she has $5 million in the bank, then sell it all off and retire. She said most of her attention now is into finding new actors and actresses, and other than webcam shows she rarely performs anymore.”

We finished our coffee and looking at the time decided it was time to start getting ready for the night. I went outside and had another smoke, thinking about what Lois had told me. Trying to grasp that the shy mousy Melanie I knew from college was now a porn actress who calls herself Josie.

I went upstairs, intending on taking a shower and getting dressed. But as I slipped into the room I froze. Melanie was still on the bed, and her laptop was still in front of her. But a Nine Inch Nails CD was playing in the stereo next to her, and she was naked. Not only was she naked, she was masturbating.

She had pushed the laptop down towards the foot of the bed, and said “There guys, is this what you wanted to see? My fingers frigging my pussy? Well, I only have about 10 minutes left then I have to get ready for a night with my friends so this is going to have to be a quick one. So just show me your love with more tips and I will finish my show first.”

She looked up as I gasped softly, and her eyes grew wide. I was about to say something, but she quickly raised her finger up to her mouth and made a “shush” motion across her lips with it, then made a show of licking her finger. I moved to the chair I had been sitting in earlier, and took a seat, watching her.

The finger she had licked she moved down between her legs. Spreading herself with the fingers of her other hand she started to caress her clit with the wet finger, and moaned softly. “Oh guys, I have to hurry though. Remember I told you my roommate was going to be back here soon, and I can’t have her catch me. But you have all been so nice to me, and gotten me so hot I can’t hold back any longer.”

This is not the first time I have seen another girl masturbate, but she was by far the most shameless. She would alternate between stroking her clit and shoving 2 then 3 fingers into herself, all the time giving a running commentary on how wet she was, how hard her clit was, and how good her orgasm was going to feel. And almost as if on cue, 10 minutes later she gasped and moaned, and came on her fingers.

And by the flush on her chest and the way her cunt was clenching and pulsing it was not a fake one either. She actually came right in front of me, as well as who knew how many guys had been watching her through the camera on her laptop. Finally, she looked into my eyes as she licked her fingers clean, then said goodbye to her viewers before clicking a button then closing the laptop.

“Sorry about that, Josie” she said. “I really did mean to have that finished before you got back. I guess I just lost track of time.”

I told her it was alright, I had already been filled in on how she made her living earlier. I let her take her shower first, and I sat on the toilet and we continued to talk. She had indeed almost completely retired, only appearing as a performer in 3 or 4 productions a year, and as a supporting member in maybe a dozen more. Most of her money came from JDJ, but she also cleared almost $100k a year from “Josie Girl”, which is what she called her webcam service.

We talked a bit, and as she started drying herself I slipped off my clothes and got into the shower myself. I asked her if it was true she planned on retiring once she hit $5 million, she said it was a fact. And she actually had almost $2.5 million in the bank now. And she figured that she could retire in another 4 or 5 years.

“Of course, I could probably retire next year if I really wanted to. But there are some things I will just never do, on or off-camera.”

“What do you mean?”

“Oh, I don’t do girls. I will kiss a girl as a way to tease in front of the camera, but that is it, nothing more than that. Never more than kissing for a minute or less, and no touching under clothes. I also will never do more than 2 guys at once, and no way is anybody ever ever ever gonna put anything in my ass. Not even a finger! I don’t do big cocks, and while I may do voyeur scenes I do not do public sex or exhibition types of videos.” I watched as with a towel around her body she was putting on her makeup.

“I have had enough offers for all of those and more that I could easily top my goal next year if all I wanted was the money. And by the way, that is $5 million before I sell my share of the company. That should easily clear me another $3 million I figure. Even more when we finish the plans on the resort.”

By now we were both putting on our make-up, and I asked her what the resort really was going to be. “Oh, I’m sure you can figure it out by now. It’s going to be our studio. Private pool, we are going to use maybe 10 of the rooms as offices and other professional settings. Then 10 are going to be configured as apartments or remain as hotel rooms. Jack, Doug and I are going to convert the 5 suites on the top floor into our own private apartments, each with 3 or 4 bedrooms, kitchens, the whole 9 yards. And the rest we will configure as apartments for use by those we hire. Some of the girls even want to share them and alternate giving webcam shows out of them.” She moved away so I could use the mirror.

“The bar and restaurant we are going to use as production sets. It can be really hard not to mention expensive to set up a location shoot. Most businesses will not allow porn shoots for obvious reasons, and those that do either only work for one company or another because of mob connections, or contract reasons. Or they want us to pay out the ass for the rights. This way we can run our filming more professional, and not have to constantly change the sets in the warehouse we rent now.”

“Melanie, that’s actually quite impressive,” I said. “And you are going to use this resort after that?”

“Yep. One of the conference rooms we are going to set up as a fake porn theater, so we can do glory hole videos, sex in the theater, or other ideas I have had. The other we want to do some things like the Japanese do. 20 couple orgies, gangbangs, things like that.”

By this time Melanie had slipped into a pair of panties and a midnight blue cocktail dress similar to mine, and as I moved into the closet I felt a bit more daring. “Wow, that sounds pretty complete already Melanie! What other things could you do?”

I opened my suitcase and pulled out something I did not plan on wearing, but it felt right this time. A black garter belt and stockings. I was just pulling the belt into place as Melanie answered.

“Oh, I want to start doing cougar and MILF videos. Older gals with young guys. And couple orgies. No swapping at all, the same guy and gal together all during the hour-long scene. And bukkake, that is huge in Japan!”

I was finishing rolling up my first stocking, and attaching the fasteners. “Bukkake, what is that?”

“Oh my Josie, you are such an innocent! Actually, it’s Japanese, and means ‘to splash heavily’. In short, you get one girl then have one man after another cum on her face.”

“Ewww, that sounds gross!” I said. I was rolling up the second stocking now.

“Yea, it is another thing I never do, other than with a single guy. But in Japan they have an entire series based on it, believe it or not with the girl pretending to be giving a television broadcast. As in being the announcer or weather girl. One thing leads to another and as she is trying to be completely straight and calm one guy after another fucks her or has her jack him off as she continues the presentation. Then each will cum on her face.” I could not help but gasp softly.

“It is kinda gross, and demeaning I admit. But I also find it hilarious, where they are trying to be so serious and pretend that they are not getting fucked as they tell the news. Then continue as one guy after another stands up and cums on her face. By the time it ends they will have 9 or 10 loads dripping all over them as they try to conclude the broadcast.”

By now even I was giggling with her. And I admitted I could see how it was kinky as well as absurd. I was saying it sounded outright surrealistic as I stepped out of the closet, and Melanie gave a low whistle when she saw my outfit. The black cocktail dress was barely lower than the tops of the stockings, and just a hint of the dark band could be seen under the hem. I wished the hem of my dress was an inch or two lower to hide this, but I also had to admit it made it obvious I was actually wearing stockings and not pantyhose. And there were just the slightest of variations under the thin silk of the dress to show I was wearing a garter belt under it.

“Dang girl, you look so hot that if I swung towards girls in any way I would make a play for you tonight for sure!” she exclaimed, and came over and gave me a hug. This caught me a bit off guard, as we had never really hugged before.

We were finishing up our preparations when I finally asked the question that had been bugging me since I talked to Lois earlier. “Melanie, I gotta ask. When did you choose the name ‘Josie’?”

She blushed as she put the last of the things into the clutch she was bringing that night. “Oh, when I got the job at White Satin, the manager told me I needed a stage name. I ran through a couple like Cheyenne, Lucy, Jasmine, and Veronica, but they were all taken already. Then for some reason, I thought of you and Josie was not taken. So professionally I have been Josie ever since.”

“You thought of me? Why me?”

“Well, you always seemed so mature, so confident. You really had it together, Josie. I actually kind of idolized you. You were sexy, and also always seemed to be in control of anything around you. I realized that is what I wanted to appear to be like, so I borrowed your name. I hope you don’t mind. I even did sets sometimes wearing cat ears and tail so people would think I got it from the cartoon or movie. I think only Lois ever had a clue that it is really from you that I got the name.”

I was oddly flattered, and told her so as we left the bedroom and headed into the living room where the other 3 were waiting. We were all dressed up to kill, and we each had a glass of wine as we waited for the limo.

At dinner we shared a platter of raw oysters, and joked that we should do that with guys next time, since it was supposed to help them out more than it did us. “Oh, I don’t know” Kris said, as she stuck out her tongue and actually licked one off its shell as we watched. “I have always had a thing for, hmmmm, nice juicy wet and salty oysters.” We all giggled, both at the double entendre that she made as well as the sexy way she licked it up, reminding me of years earlier when she would lick my oyster in the same way.

Sam and I each selected the surf & turf, a steak and prawns. Kris settled for fried clams, as Lois got the steak and lobster and Melanie selected the salmon steak. We continued to chat and tease each other all through dinner, sharing another 2 bottles of wine as we did. Then after a trip for each of us to the ladies lounge to relieve ourselves and touch up our makeup we headed to the Red Room.

Thankfully Sam was known there and was expected, so we strolled right on in. We each checked our purses in at the cloakroom and were soon sitting at a table having our first drinks of the night. Sam was just finishing hers when a tall slender guy came up and asked her to dance. With a wave she accepted and the two of them headed off. We had already agreed that at least one of us would remain at the table at all times, both to hold the table and to make sure nobody did anything funny with our drinks.

A short time later Lois and Kris headed off to the floor, and were soon dancing together. I watched them together and they looked to still be comfortable with each other after all these years. “So Josie girl clears $100k a year doing webcams, what was today worth, may I ask?”

“Oh, I think I saw it was at around $12,000 when I signed off.”

I almost choked on my drink at that. “You made 12 thousand dollars in what, a half-hour or so?”

“Oh no, the show was actually over 2 hours long this afternoon. I started it while we were talking but then I was only teasing them a bit. I did not actually start the real show until after you left. But yea, most of it was in the last 45 minutes or so. My regulars love it when I masturbate for them, and today a real bidding war started. I had already promised to send the panties I had been wearing earlier to the guy that bid the most. My site is membership only, and this week is only open for those that pay extra to see these shows. “ A guy came up and asked her to dance, but she politely declined.

“They knew weeks ago I was doing this trip, and they loved the idea that I was taking a road trip. It is something new for them, seeing me on my laptop instead of in my apartment or office like usual. And more than a few have asked for private dates while I am out here in California, but I refused. I don’t do that anymore.”

“You don’t date?”I asked, confused. She laughed at that.

“Oh, I forget how innocent you are. In my business, a date is a private sex session. For money. I do date guys, but only as dates, not as customers. And I still perform for the camera, but I have not actually whored myself out for years now. Now I only fuck a guy as part of a performance, or because I really like him and want to fuck him. And of course if I am actually dating a guy I will fuck him. That is yet another thing Josie does not do anymore. I have not done that in over 3 years now in fact. But if I did, it would help me hit my goal even faster. But like I said, some things I simply will not do. Prostitution is now long in my past.”

 
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