PART 1
We drove up to the resort in mostly silence, but it wasn’t uncomfortable. The playlist my wife and I had been listening to had run out and we hadn’t bothered to put anything else on. My mind was racing, because I could barely believe that we were actually going through with this. I know her mind must have been a mess of thoughts as well. She just looked out the window, watching the growing thickness in the tree line along the highway. There were times that the silence freaked me out, made me think this was a bad idea. However, I’d then catch a glimpse of her slowing running her fingers along her bare thigh, while wearing her pink shorts and then a slight, barely audible, moan.
“You scared me there for a second babe,” I said to Jess. “You’re not getting cold feet are you?”
Jessica looked over at me with a slight fire in her eyes. “I’d be lying if I said I’m not nervous as hell. What if everyone thinks I’m the boring, ugly one?”
“Bullshit. You’re going to be the most gorgeous one there, I’m the one getting shortchanged on this whole thing,” I replied with a smile. I wasn’t lying either, my wife is the hottest girl I’ve ever seen in real life. Her long red hair was resting against her bare shoulder, contrasting nicely with her tanned skin. She had hit the tanning booth for a couple of weeks before this trip. I actually preferred her with her natural, more-pale, skin tone … but I couldn’t argue that her darker skin just begged to be touched.
“Babe,” she replied back playfully, “I’d be surprised if I got 100 views on my videos. You’re going to top the 1 million mark.”
I actually burst out laughing at that. “You’ve got to be freaking joking right?” While comparing males to females is completely subjective, no one in their right mind would think that I, a little chubby and only 6’, could in any way compare to her 5’5”, 120 lbs, lean and soft body.
This whole week came from a party that we had a couple of months ago.
What started out as a normal get-together of all of our friends turned into the craziest night of our lives. There had always been some sexual tension amongst our friends, but for some reason, maybe the tequila and full moon, it all came out that night. We talked about what it would be like to swap partners, play erotic games, and even have 3somes or orgies. By the end of the night statements like “oh yeah, I’ll bet you’d like to see me naked,” turned into “No seriously, I’d totally fuck all three of you at once.”
We ended the night with a wild game of “I’ve Never” which ended with Jess and her best friend Jenni going down me while many of our friends watched and then joined in with each other on their own.
All that week after, Jess and I had the most amazing sex of our marriage, thinking about how hot it was to just let our inhibitions loose and do what felt good. It was my friend Bob who suggested the swingers vacation and said we should stream the whole thing on the internet to make some money off of it. We all talked and said, “what the hell,” and agreed. He set it all up and now we’re all headed to a private (but fully wired and stocked) resort up north to fuck each other’s brains out and hopefully get paid for it.
“Do you really think that the tips given on this site are going to pay for this vacation?” Jessica asked as she continued to run her fingertips along her long legs.
“Well, this whole thing is going to cost about 10 grand, and we’ll be broadcasting for a week, so I don’t know. Bob seems to think that this is going to make us millionaires for something.”
“Yeah right,” Jess laughed. “I mean, half of our group is decent looking, but we’re not model-hot. I mean, who’s going to pay money to watch Fred and Dave have sex with Lilly?”
“Gross,” I coughed, as I almost let a little vomit into my mouth. “But I couldn’t not invite them, I mean, they were there the night of the party, even though they didn’t join in, I could tell they wanted to.” Fred and Lilly were married, and they weren’t the ugliest couple of all time, but their brand of attractiveness wouldn’t do well on non-fetish sites. “I mean, everyone has their kink.”
The resort we booked was on the shore of Lake Michigan and had 4 bungalows and a common area with kitchen, living room, ect. Each sleeping area had two bedrooms, each with a king-size bed. Before the trip, we agreed that once everyone arrived, we’d each choose a number 1-4 … and that would be the bungalow we’d sleep in (no spouses allowed with each other) There were going to be 16 of us, which I honestly couldn’t believe when we pitched the idea to all of our trusted friends.
We pulled up into the lot of the place and there were already 2 other cars there, I recognized both of them. I parked next to the bright blue one and got out only to be hit like a linebacker with a hug from Jenni. After the normal ten seconds or so of being squeezed to death by a 5’1” brunette, she turned her attention to my wife and did in fact knock her down with the force of her hug.
“Holy shit is good to see you two!” Jenni said with extreme exuberance.
“Can you believe we’re doing this? Like seriously, what in the hell were we thinking?”
“Hopefully that we can all have a little bit a fun before we go back to our normal lives,” Jess said. “But if you get paired up with Will, don’t you dare make any plans to run off together. I know he’s had his eye on you for awhile, but he’s mine.”
“Lies!” I laughed as Jenni actually blushed a little.
They weren’t. I had wanted to fuck Jenni from the moment I saw her. That lust only grew the more I got to know her, as she was one of the coolest chicks I have ever known. Jess was mostly joking, but she had no idea how close to the mark she had come. I’ve never cheated on her in my life, but I came the closest one night with Jenni while we were both working late on the weekend.
We were then joined by our friends Bob and Tracy, who were down by the water when we pulled up. Bob, who masterminded this whole trip, had a coffee tin in his hand. Bob was an A+ when it came to male attractiveness, he was tall, handsome, and could charm the scales off a snake. His wife was also extremely gorgeous, all be in a little skinny for my taste. Both were going to get a lot of viewers whenever they took off their clothes.
“I’ve been here for about an hour and have already made sure everything is up and running. I hired a dude to moderate and send us viewer requests through the iPads that are in each bungalow. He’s hopefully earning his $20 a day.” Bob said as he shook up the coffee can. It made a distinct rattling noise, like the sound of change clinking together. “I ordered custom coins with the numbers 1-4 on them to determine which house we get sorted into.”
“Isn’t there a whole hat for that?” asked Jess sheepishly. “Not Slitherin, Not Slytherin.” I laughed at the unexpected Hogwarts reference as another two cars pulled up.
“Excellent. It looks like Gary, Chyanne, Fred and Lily are here.” I said.
Fred and Lily got out of their van looking a little grumpy. Out of everyone, Fred was the nay-sayer in this trip. His wife wanted it so bad that he eventually caved in. Neither one was that easy on the eyes, and Lily wasn’t easy on the ears or brain either, but they were mostly good people. It was obvious that Lily wanted a crack at something different and Fred was a little nervous about the whole situation. Lily came out and hugged me as Fred embraced his best friend Bob.
Gary got out of his car next. He was 6’2”, a respectable 215 lbs even though he’s never worked out in his life. He had let his hair grow out since I’d last seen him. His new girlfriend Chyanne got out next, with long blonde hair and a slender build on her 5’7” frame. When I found out that he was dating her, I was shocked, because she had a thing for Bob originally. In fact, her and Tracy were best friends before we started hanging out with them. Chyanne then became Friends with benefits with Bob while she secretly wanted to marry him and he secretly wanted Tracy. He got his way. She and Gary must have fallen for each other while they were both nursing broken hearts. As shocking as that was, nothing could have prepared me for what happened next.
A long, tanned leg popped out of the backseat of the car, followed by the rest of my ex-girlfriend … Nicole. I hadn’t seen her in nearly 5 years since I was 24 and she was 21. She was still a knockout, standing 5’9’, with down to her butt blonde hair with brown lowlights, flat tummy and perfectly shaped triple D tits. Her smile instantly faltered when she spotted me and my wife staring at her getting out of the car.
Jess grabbed me by the arm and pulled me away from the rest before furiously whispering in my ear, “What in the world is she doing here? Did you know about this!?”
“NO!” I exclaimed. The look on my face must have been convincing because her grip and tone instantly relaxed.
“Well then, interesting…,” Jess said with a devilish smile. She knew Nicole and I’s history, but in that moment … I had no idea what she could have possibly meant by that statement. We rejoined the others as they noticed our obvious absence. We all stood there in silence as everyone (with the exception of Jenni, who just looked bewildered) looked from Nicole to me and over again.
Luckily, Jenni broke the silence. “So, Barbie here must either be Will’s sister or ex-girlfriend. And I sure hope it’s the later because as weird as that is, it’s not as bad as the first.”
I thanked Jenni later on for easing the tension.
Chyanne spoke up, “Nicole is my best friend. We work together at the hair salon. I invited her, she had no idea that Will would be here. In fact, I had no idea that you guys even dated until the trip up here.”
I shot a look at Gary … who would have been well aware of my past with Nicole.
“Ok. Ok! Yes, I obviously knew. Fuck me.” Gary said without remorse.
“Good luck with that sweetheart,” Chyanne said, not unkindly.
“I should go,” Nicole said as she looked down.”
“No, no, no!” Bob said. “This doesn’t change anything. In fact, it just means that we all know each other a little better than we thought we did. For god’s sake … we’re about to have a week-long swingers party and we’re worried about who’s fucked who 5 years ago?” Everyone thought about that and then realized how silly this tension was. I had dated Nicole off and on for 7 years, since she was a sophomore in high school. We had a lot of fun, but because we had agreed to wait until marriage to have sex, we technically broke up as virgins (even though our naughty bits were always in each other’s mouths.) Most of our oldest friends knew this, and I knew they were just wondering what was going to happen if her and I actually found ourselves alone for a few minutes.
I wondered myself…
“Well, we have enough people here to get started anyway,” Bob said as he held out his coffee can. “There are going to be 16 of us, so we’re still missing six, but I can stay out here until everyone else gets here. We just have to make sure that at least every house has at least one dude or chick. Let’s do some picking!”
Fred went first and picked out #3 while his wife selected #2. They both picked up their stuff and headed away.
Jenni went next and picked out #4. She happily bounced toward the house closest to the lake.
Nicole went next and picked #2 but didn’t leave because she wanted to see which house Chyanne got.
Chyanne selected #3 while Gary pulled a #2 out of the can. He and Nicole walked over to the house right next to us while Chyanne, kind of sulkily walked toward her house. I’m not sure, but I think she was hoping to room with Nicole, not have Nicole room with her boyfriend.
Jess and I looked at each other and then at Bob and Tracy. “Can you guys pick first,” I asked. “I’d rather give this two more chances to not get a #2 before I pick.”
Tracy looked like she completely understood and reached in and grabbed a #4. She kissed Bob on the lips and walked toward the lake.
Bob reached in and grabbed #4 out of his can. “Fuck!” He exclaimed, “I can’t do 4 because Tracy is in there. That sucks, Jenni looked like she’d be a lot of fun.” He reached in again and this time came out with #3. “Oh, much better. Now I get Fred and my old fuck-buddy,” Bob said sarcastically.
“Hey man, there’s no rule that says you have to have sex only with the people in your house,” I reminded him as Jess elbowed me in the side. “What?!?”
“Just pick already,” Jess whined. “I have to know .”
“You first.”
Jess sighed and put her hand in and pulled out the first #1 and laughed. “Ha! Now I’ll know who you’re with but you won’t have any idea who I’m with.” I was about to reach my hand in when another car pulled up.
“Actually, I’m going to wait until after Tori and Sarah pick,” I said.
“For fuck’s sake dude,” Bob laughed.
Sarah and Tori were best friends who worked with Jess, Jenni and I. Jenni had suggested the outing to them as a way to get over recent funks. Sarah had just broken up with her boyfriend of 4 years and Tori was thinking about leaving her husband who hasn’t been interested in sex in just about as long.
Tori was MAYBE 5’ even and weighed under 100lbs, she had the smallest ass I’d ever seen on an adult female before. She was really cute and had always been a great friend to me at work.
Sarah was 5’6”, average looking in just about every way, but the woman oozed sexuality. She was always making inappropriate comments at work and she was the first person I’d developed a crush on after getting hired, mostly because we had instant flirting chemistry.
If fact, within the first 3 months of working there, I developed crushes on Sarah, Tori, and Jess. I sometimes hate to admit it, but I chose Jess to pursue simply because she was the only one at the time who wasn’t spoken for. Jess had no idea.
The two girls came over and we made small talk for a few before Bob explained the situation.
“So Will won’t chose until we do so he better knows the odds of getting stuck with his Ex?” Sarah asked. I nodded. “What do I get in return?”
“Just pick you slut,” Tori said as she slapped her best friend’s ass. “Do the boy a favor.”
Sarah did as she was told and picked out a #1. “Who am I with?”
“Just me so far,” Jess said.
Tori reached in and grabbed a #4, and looked at me. “Well, we’re waiting. What’s the unlucky number?”
“2” I replied. I sighed with exasperation and then stuck my hand in the coffee can and came up with my coin. I looked and then sighed with relief. “Thank god, #4”
“Fantastic,” Tori said … “looks like you and I are bunk buddies.”
I had wound up in a bungalow with three females, all of which were cute as hell, so it most definitely could have been worse. I looked over at Jess and she seemed happy that I wasn’t in a cabin with Nicole, so I look that as contentment with my current sleeping arrangement.
“I love you babe,” I said as I kissed her. “I’ll see you in a little while.” I grabbed mine and Tori’s bags as we walked down by the lake as Jess and Sarah walked over to the closest place. I looked back just in time to see the other couples, Tom and Yuki and Dave and Kelly arrive in the same car.
“This is going to be a fucking awesome week,” Tori said unexpectedly.
“Yeah? My ex showing up out of nowhere freaked us all out a bit, but I think we’re still going to be able to have a little fun,” I said.
“Hell yeah. And it’s going to start the minute we get inside because I’m going to fuck your brains out Will.”
“What?!”
“Don’t what me. I’ve been waiting to get on top of you since you started working at the station, and now I can finally do it guilt-free.” I just stared at her, as I had no idea she felt this way. “Seriously, you’ve got five minutes to get ready or you’re in fucking trouble.”
How do you say no to that?
[PART 2](https://www.reddit.com/r/eroticliterature/comments/5b0apz/we_went_all_out_for_our_first_swinging_vacation/)
Source: reddit.com/r/eroticliterature/comments/5b08l3/we_went_all_out_for_our_first_swinging_vacation