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.
