In Hawaii Where It All Began

Hi everyone. My name is Judy, and I am 28 years old. Until recently, I was a faithful wife to my loving husband Tom. And then, over the last three months, I ended up cheating on Tom on three different occasions. And when I say cheating, I mean cheating in a big way. Each time was with multiple men and involved more than one session.

I never planned on cheating on my husband but have now accepted the fact that if the right situation arises and there is a dominant, strong male involved, I become insatiable and will pretty much do anything sexually with pretty much anyone while I am in the throes of passion. You would think this would put a damper in my marriage, but Tom discovered what was going on during my last transgression when we were on a camping trip. During the weekend trip, I ended up fucking four guys in the next campground several times, and Tom, once he discovered what was going on, ended up loving it. He had always liked it when I wore skimpy clothes and got appreciative looks from other men and had in fact encouraged me to show off. But he did not realize the impact seeing me suck another man's cock, swallow his cum and then have multiple men fuck me in all of my holes would have on him. Instead of being jealous, he was insanely turned on. And on the last night of our camping trip, he joined in the fun, and I ended up being gangbanged by all five guys (you can read about all of it in the Camping trip with wife stories).

Tom and I have talked since then and agreed that we would have a sexually open marriage and would be completely honest with each other. I told him about the other two times I cheated on him before the camping trip. He was more than ok with it once I described what happened in great detail. In fact, it led to some great sex between us. He also told me that I could do whatever I wanted sexually going forward as long as I shared what happened with him. He would prefer to be there and directly involved, because he was a pervert and liked to watch and participate, but that was not a requirement if I told him what happened afterwards. And I told him that I was cool with him playing around too if the opportunity arose under the same conditions. I wanted to participate if possible, but definitely be told the details if I wasn't there. Now that you are caught up, this is the story of the first time I cheated on Tom in Hawaii.

Tom is a salesperson for a large software company. Every year the company has a retreat in an exotic location for their top salespeople and customers where they get some training, give out awards for the top performers, and play tons of golf and drink. Spouses and significant others can come along, but at their own expense. Most don't because the planned events are usually for the employees only. This year the trip was in Hawaii, on Maui Island, and the retreat was from Saturday through Wednesday. Tom and I decided that he would take some extra time off after the retreat and we would make a private vacation out of it. He flew up on Saturday and I came up on Monday. I knew that I would spend the first couple of days mostly by myself and only see Tom during dinner and afterwards, but I figured I would work on my tan and maybe do some shopping and engage in some water sports at the hotel until our romantic vacation started on Thursday.

Unfortunately, I ended up seeing Tom less than we anticipated as he was busy with work events and schmoozing customers even during dinners as well. He would leave the room before 8 a.m. for the conference breakfast and I would not see him at night until he came back to the room past 11, tired, drunk, and exhausted. Let's just say my thoughts of some pre-vacation romantic evenings were not being fulfilled and my libido was on overdrive.

Wednesday was supposed to be my last day alone in Hawaii and I decided to live a little. I slept in and headed to the beach around 10 a.m., wore the skimpy bikini that I was saving for Tom, and hit the Mai Tais on an empty stomach. The bikini I was wearing had ties on each side to hold the bottom together and a tie behind the back holding up the top. So, no straps over the shoulders, which limited the tan lines. It was not quite a thong, but both the top and the bottom were pretty small, so lots of ass cheek and side and under boob showing. It was pink and went very well with my complexion and new tan. I guess I wore it because I was sexually frustrated over the last few days and wanted to feel a little sexy and naughty. I definitely had no intent to cheat on my Tom.

Before I go any further, let me describe myself. I am five-six and weigh 115 pounds. I have light brown hair and green eyes. I have been told that I have a pixie like face and look a little bit like a young Julia Roberts (not saying I am as hot or anything, just the celebrity people say I most resemble). I am not a stick by any means but do a have good figure, curvy without being fat, with 36C cup breasts. I stay in decent physical shape through a lot of jogging and yoga. I don't mean to brag, but I have noticed men staring at me when I wear the right clothes and think I would be considered pretty good looking by most standards.

So, here I am at the beach, with a very nice buzz going after several strong drinks, when I notice parasailers over the ocean. They were gently coasting in the air as the boat was pulling them along. The view must have been incredible. I decided I wanted to try it as well and noticed that there was a dock near our hotel's beach with a parasailing sign. I packed my stuff (a beach bag with a towel and my hotel card) and walked to the end of the dock where there was a boat with a couple of guys in it and a young guy sitting under a sign with a clipboard in his hand. I walked up to the guy with the clipboard and told him that I wanted to sign up for parasailing.

He was a young kid, white, with blonde hair, in decent shape, wearing board shorts and no shirt, which seemed to be the uniform for almost all the beach workers around here. He was occupied writing something on the paper on the clipboard. Without looking up, he said they were on their lunch break, that they were fully booked for the day, and that the next opening was not until Friday afternoon. I was about the walk away disappointed when one of the other guys jumped off the boat and ran towards us.

"Hey Jim, we are pretty much done with lunch and have an hour before the next shift. We can certainly make an exception for this young lady and take her during our break."

I turned to thank him and stopped in my tracks. He was at least six two, dark hair, with an amazing tan. Looked like he was part native Hawaiian and part white. He was also wearing nothing but swimming trunks and had an amazing physique. Not overly muscle bound like a bodybuilder but cut with an impressive six pack. Even though I was wearing sunglasses, it was pretty obvious that I was checking him out and it was also obvious that he was doing the same with me. Neither of us said anything for a second or two, but it was clear that we both liked what we saw and there was some serious 'good' tension between us.

Jim finally looked up from his clipboard and his reaction was almost comical. I was standing a couple of feet in front of him, and his eyes were about level with my stomach. When he looked up, the first thing he saw was my legs and then he slowly looked up and was pretty much staring at my boobs with him mouth gaping open. I guess I should have been offended, but with the nice buzz going, I found the whole thing more funny than rude and almost giggled.

Jim finally stood up and stammered, "sure Terry, I am sure we can make an exception."

"Hi, I'm Terry and I manage this bunch. If you are still interested, the cost is $50 for a half hour." The entire time he was talking, I could tell that his eyes behind his sunglasses were roaming up and down my body. And he was not hiding it. It sent a shiver up my spine and warmed me up all over, even more than the Mai Tais.

"Hi Terry. I'm Judy. I would love to. Let's get going." With that Terry escorted me to the boat. And, even though I don't think I needed it, he helped me get on the boat by first holding my hand and then holding my hip to steady me as I was stepping on to the boat. His touch on my hip, which graced the side of my ass sent another jolt though me. He was so confident in his touch and movements that I could not help myself. In a deep animalistic way, I wanted this man to take me. And I could feel myself getting moist. My inner voice told me that I was a happily married woman and to calm the fuck down.

Terry introduced me to the third guy on the boat, Drew. Drew was of Japanese descent and like Jim and Terry, shirtless and in obvious good shape. He was the driver of the boat while Terry and Jim's job was to hook up the passengers to the gear and make sure everyone was safe.

Before they take you up in a parasail, the boat has to go deeper into the water to a designated spot. This takes around 5 minutes. While Drew was driving the boat, Jim started getting the gear ready while Terry sat down next to me to explain the process and have me sign all the waivers. But before he sat next to me, Terry first went to talk to Jim. Jim nodded his head and then took off the gear that had two harnesses next to each other and replaced it with two harnesses that were lined up front to back. While this was going on, Terry told me we would be up there for around 10-15 minutes and that he would be going up with me since the parachute was designed for two people and I did not weigh enough to go up alone. I assured him that was fine.

Before you know it, it was time to get harnessed up. The harnesses go around your upper thighs and waist and you just basically sit in it with nothing covering your bottom other than what you are wearing. Straps come up on each side from your waist and hook up to a long horizontal pole which is attached to some straps at the bottom of the parachute. I had mostly seen parasailing with people hooked up next to each other. Seeing a front to back arrangement like we were doing was something knew. I figured the guys knew what they were doing and did not say anything. In retrospect maybe I should have. Things might have turned out completely different if I had. Terry's harness was strapped in first and I stood in front of him and was strapped in as well. Then the boat sped up and we were pulled up into the air. It was an amazing and exhilarating feeling.

Once we were up in the air, I immediately noticed that having us front to back and strapped to the same pole meant that Terry and I were very close to each other. In fact, his crotch was pretty much nuzzled against my ass and his arms were on the side and around my waist as they had nowhere else to go. I began to suspect that the change in the arrangement of the harnesses was done just for this purpose. I later confirmed this with Terry who told me that they did the harnesses this way only for parents with little kids or couples on their honeymoons who requested it.

I figured there was nothing I could do about our close quarters, so I decided to make the best of it and simply enjoy the view and this amazing experience. However, I began to feel an impressive bulge forming and growing between my ass cheeks, and it was becoming increasingly difficult to ignore. My heartbeat started to speed up and my breaths were becoming shallower. And, despite the voice in my head saying I was a happily married women, I could also feel myself getting very, very wet in my pussy. It was obvious that I was very much enjoying this extracurricular portion of parasailing. Before I even consciously thought about it, I began to rhythmically clench and unclench my ass cheeks, messaging the obviously large cock that was now fully wedged between them.

Terry acting like nothing was going on pulled me closer with his left hand on my stomach and started pointing out some landmarks with his right hand. I could feel his breath on my neck, which was doing nothing to calm down my libido. To be frank, to this day, I have no idea what he was pointing to most of the time because my focus was now entirely on the cock grinding against me as my breathing got faster and faster. By now, the voice in my head telling me that I was a happily married women was completely silent. And if it had spoken, I would have told it to shut the fuck up.

I finally came out of it when Terry started talking about a nude beach that we were flying over. I looked down at the beach and did see a bunch of people that were either topless or totally nude. I also realized that Terry's left hand had now crept up and his fingers were basically caressing the underside of my right boob. I know I should have stopped things right there, but I was enjoying the feel of his hand directly on my skin. And to be frank, I love it when my husband Tom gently caresses my tits. It always gets me going. So, Terry, was doing just the right thing to rev me up. Instead of saying anything or moving his hand away from my breasts, I continued to grind my ass against his crotch and told him that the nude beach looked like fun and that I would try to get my husband to go there with me later this week.

Maybe I was hoping that mentioning my husband would get him to stop. Although the continued and obviously intentional grinding against his crotch was sending the exact opposite message. And, based on Terry's action so far, there was little chance of him actually backing off. More likely it was a way for me to try to relieve some of the guilt from the situation. See, I am telling you I am married, so you should stop and whatever happens is not my fault, or so I was subconsciously thinking.

"No way, would you go to a nude beach and be naked in front of a bunch of strangers."

"You just met me. For all you know my husband Tom and I are exhibitionists and go to nude beaches all the time." Now why did I say that when it wasn't true?

"I guess it's possible, but you don't seem the type."

"Ok. I will prove it to you. I will go to the nude beach with Tom tomorrow and send you a photo." I couldn't believe I said that. Apparently, I was enjoying our conversation and the sexual tension between us, as well as the large cock wedged against my ass, obviously a bit too much. But did I want him to see me naked? Did I want things to go further?

"I don't want to wait even though a nude picture of you would be amazing. I need proof now."

"How do you propose on getting that proof now?"

As soon as those words came out of my mouth, I realized what Terry was going to do. But even if I wanted to stop him it was too late. Before I could say or do anything, he undid the tie behind my back and pulled my bikini top off.

"What are you doing!" I screamed and tried to cover my now naked tits with my right arm.

"Getting immediate proof that you would get naked in front of strangers," he laughed. And then he immediately untied the straps on the sides of my bottom and pulled my bikini bottom off as well. In less than 5 seconds, I was sitting in the parasail harness completely naked.

"Oh my god! I'm naked," I screamed.

"That's the idea," he chuckled.

"But everyone can see me!"

"You are 200 feet off the ground and half a mile offshore. No one can see you but me. And since you were going to send me a nude picture anyway, what's the big deal. Besides, the real thing is much better than a photo. Especially when you are not just looking and can also touch."

With that he nuzzled his mouth against the back of my neck, grabbed both of my naked boobs with a hand on each and pulled himself even closer to me. God help me, I did not want to cheat on Tom, but I just could not help myself. I think, maybe I hope, that I quietly said something like "but I'm married." Maybe I just thought it. I don't know. But either way, he ignored it. He was confident, he knew what he wanted, and he knew I was putty in his hands. I moaned as he began to kiss my neck and gently knead my tits. He had this great technique where he would caress the underside and side of each breast and then put my nipples between his index and middle finger and gently squeeze and pull on my nipples. At the same time, he was nibbling on the side of my neck mixing small kisses and small bites. I could feel his hot breath. Oh, it felt so good.

By now the only words coming out of my mouth were "mmm, oh yes, oh god."

Soon, his right hand left my right breast and slowly made its way down to my stomach and began to gently caress the top of my pubic bone. I was so wet and ready at this point that when he found my clit and began to slowly circle it with his index finger, I began to moan even more loudly and could feel myself on the way to a huge orgasm. And he hadn't even put a finger or that amazing feeling cock in me yet.

At this point, all thoughts of Tom had disappeared from my head and all I could think about was getting Terry's cock inside me. I put my left hand behind me to grab his bulge. To my pleasant surprise, I discovered that the front of his swimming trunks had a Velcro fly. I quickly ripped open the Velcro and fished out his now fully hard cock. Even though I could not see it, I could feel its heat and the fact that it was very impressive in size. Tom is by no means small, but Jerry was definitely an inch or two bigger. I began to rub up and down on his cock and reached further down to gently grab and caress his balls. For the first time, he started moaning as well. "Oh yes, play with my cock, that's it."

Terry, by now, had managed to get his middle finger inside me while continuing to play with my clit using his index finger. I started to hump his hand in earnest. Right when I thought I was about to cum he pulled his finger out of me to my great disappointment. But I had little to worry about. He then grabbed my hips lifted me up a little inside my harness, just a few inches, and pulled us closer so that my ass was now directly over his cock, and I can feel the tip poking inside my thighs. Realizing what he was doing, I reached between my legs, grabbed his cock and inserted the head between my pussy lips. He then sat me down on his gorgeous cock.

Maybe because of the tension leading up to it or the fact that I knew I was doing something wrong, the feeling when he first entered me was amazing. I literally almost blacked out. Despite the fact that it was 85 degrees outside, I could feel the heat of his cock when he entered me. And its girth, as it made its way all the way inside me, felt sooo good. I let out a very loud "ohh fuck me" as he entered me and almost came just from that.

"With pleasure," he moaned. And then he reached around, grabbed my tits and gently began to stroke in an out. That did the trick, and I began to cum almost immediately. Terry then sped up and pistonned in and out of me more rapidly. This basically led me to orgasm continuously non-stop. He kept going full bore for at least 5 minutes (he had some serious lasting power) and I think I had at least three orgasms. Maybe more. It was difficult to figure out where one ended and the next one began. The entire time I kept screaming some combination of "yes, yes, oh my god, fuck me, fuck meeee!" I am sure people on the nude beach heard me and, if they looked up, were treated to a show. To be frank, I did not give a shit.

When I felt like I was about to pass out from pleasure, Terry finally began to grunt very loudly, and his breathing also sped up. He then pushed his face forcefully into the back of my neck, pulled me tighter to his chest and his whole upper body went rigid like he was being electrocuted. He then pistonned in and out of me even faster and harder and began to moan "oh god, oh yes, oh fuuuck." It was obvious he was coming and his orgasm lasted a good 20-30 seconds. I think I had another mini orgasm to coincide with his. By this point, I was in such bliss that I barely knew what was going on.