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The Only Time I Cheated
13/11/2015
I have never told a soul about this and probably never will but after discovering this site, and reading all of the different stories I think I can anonymously tell this story. I’ve been itching to tell someone, but I think this will serve as my outlet.

I am 44 years old and my yhusband and met in college and have been married for 21 years. We have two great kids, the oldest is in college and the other a senior in high school. I couldn’t ask for a better husband and our relationship has been fantastic. We are each other’s best friend and our marriage has been rock solid. When we fight, we fight fair and get over it. I love him with all my heart and I know, without a doubt that he feels the same. It makes what happened a few years ago very puzzling to me.

One of the things that keeps our marriage strong is that about once a year we take a vacation without the kids. Sometimes it’s just a domestic trip but other years we do something bigger that always involves warm weather and a beach or two.

In our normal lives we are a very conservative family. We rarely drink, and if we do it’s only a glass of wine or a beer on occasion. My husband may have a cigar once in a blue moon but we keep in very good physical condition. We are both working professionals and are involved in the community though PTA and our kids sports. I dress as such, alternating from casual work attire to jeans and t-shirts on weekends. We don’t go out much and prefer family time at home to parties and nights out. Our sex life is good, sometimes infrequent with our busy lives, but it’s satisfying.

During our one week of vacation alone each year, all that goes out the window and we get naughty.

It started many years ago in Jamaica. Bloody Mary’s on the beach each morning, drinks throughout the day by the pool and parties at night. For the first time since college we sampled the product Jamaica is known for and did it often. We were at a clothing optional resort and after a few days of gathering our courage (meaning smoking more pot), our swim suits came off. Our subsequent vacations sometimes include public nudity and pot but is not a requirement. Our sex life always explodes. We fuck a couple of times a day. We try different positions and are much more uninhibited. I bring sexier lingerie and buy more provocative…..actually slutty…..clothing and wear more makeup for the nights out. I grow my nails long and have a pedi and mani with deep color nail polishes before we go which he loves. We have FUN!! No one at home would recognize us. To be clear, our sex is always with each other and neither of us had ever, in our 23 years since we met, been sexual with anyone else (other than this one). No threesomes, swinging, affairs or anything close to it.


Three years ago we took one of our trips to a small, out of the way, tropical resort. Our hotel room looked out over the pool and out onto the ocean. The room was on the 5th or 6th floor, I can’t remember exactly. The balconies in our section all were private and hovered almost directly over the pool so when you looked down, all you could see was the pool. You had lean your body over a bit to see sunbathers on the building side of the pool. The balconies were a solid wall (rather than open railings) and only about three and a half feet high (not to US building codes) so likewise, no one from the pool deck could see you unless your upper body was hanging over.

The hotel was only about ½ full and on our second day we noticed a single man move into the room next to us. We met him in the bar that evening and he told us that he was there with four college buddies for their annual scuba getaway. The others were in the small scuba resort next door, two to a room, and he was the odd man out. There were no additional rooms available and rather than stuffing three into a room he elected to stay in this hotel for a few nights until another opened up.

He was a very nerdy IT guy from Canada - tall, lanky, in his early thirties and pretty socially awkward but actually fairly good looking. He was married with three kids. For the next three nights, after he left his buddies at the dive resort, he came to our hotel bar and hung out with us. As I mentioned, we were usually in some state of inebriation and our conversations were pretty open. We talked about everything including sex, which would make him very uncomfortable but it was funny. He loved his family and never cheated on his wife. I remember thinking that he wouldn’t know how if he wanted to. Being an engineer myself, and working with many male socially awkward engineers, I understood him and he felt comfortable with me. The three of us had some great conversations. On the third night I noticed he was developing a cold but didn’t think much of it at the time.

That next very next day, my husband and I had a big day planned – sit by the pool and drink and read. By mid-afternoon I had finished one book and decided to head up to the room to get another. I ran into the room and left the door ajar. Once in the room I grabbed the book but decided to stay and have a cigarette (one of those guilty pleasures for me during vacations only). Since no one else around the pool seemed to be smoking that day, unlike others, I didn’t want to bother anyone so I headed out onto the balcony and leaned over to wave to my husband. I caught his attention and lit my cigarette (he has a smoking fetish and loves to watch me even if it’s six floors up). Just as I had taken my first drag I heard a voice in the room. It was our computer nerd friend poking his head in to say hi. I was startled but remembered that I had left the door open and I motioned him to come in. His cold had gotten worse which prevented him from diving that day, and as a diver myself I know you cannot clear your ears at depth with clogged sinuses.

In retrospect I could imagine what he was looking at when he entered the room - me leaning over the deck my butt pointed in his direction. It was covered by my bathing suit bottom and I had one of my husband’s t-shirt on (nothing underneath as the pool allowed topless sunbathing) but my butt is fairly small and from what he had told us, his wife is very overweight. He commented on what a great view it was. I think that I agreed that the ocean was beautiful today and he laughed and said “no, I mean your ass!”

I burst out laughing as it was unexpected coming from him. He came up behind me and playfully pretended like he was taking me from behind rubbing the front of his suit against the back of mine. I could tell by the way he was acting that he had already had a Bloody Mary or two…..or three. It was awkward but I played along because I figured he meant nothing. It was then that I felt his penis harden. I immediately felt my own tingling sensation. He jumped back, completely embarrassed and apologized profusely. I laughed and told him not to worry about it……then I looked at him and took the last drag of my cigarette and dropped it on the deck. I exhaled into the air above and gave him my best demure smile and said in an extra sultry voice…..and I can’t believe it to this day……“No Tiger, this is fun.” I was kidding and only playing with him (I think – who knows what I was thinking). I could tell by his frozen face that he didn’t think I was kidding. A person with normal social skills would have laughed, and then we both would have laughed at the weird moment and then gone down to the pool to hang with my husband. His socially inept mind could not fathom that and his strictly logical brain told him I was serious.

What happened next was a bit like a slow motion dream. I turned back around and hung my head back over the deck and lit another cigarette either hoping he’d go away, or hoping that he wouldn’t, I have no idea which. I looked down at my husband just has he looked up and he smiled. He had no idea I was not alone and there was no one on the other side of the pool that could see past me either. I heard, and then caught out of the corner of my eye, a pair if swim trunks hit the deck followed by his erect penis making contact with my exposed skin on the side of my ass cheek and then one of his fingers hooking my suit. Keeping my body in the same position I set my cigarette in the ashtray and helped him lower my bathing suit bottom with both hands. They fell to the ground and he move in behind me and rubbed his dick from my ass crack to between my legs and I took it with one hand and guided it so it rubbed against my pussy lips while I resumed smoking with my other. I remember thinking, this is just a little fun – we’re just rubbing genitals together, nothing more…..my husband looked up at me again and his smile intoxicated me… I had no sooner processed what was happening when I felt his penis disappear from my finger tips that had been caressing it. Mr. Computer Nerd had entered my pussy. I was surprised….but not. He entered part way and stopped, waiting for my reaction. I pushed my ass into him burying his dick completely inside of me and he slowly began pumping, gradually increasing power and velocity. I let myself grimace and groan when my husband had his eyes in his Kindle and regained my facial composure when he looked up. To him I was just enjoying the view and my cigarette. The nerd’s hands came up my body and under my husband’s shirt and he rubbed my breasts. This went on for a few minutes and when his pace increased and I knew he was about to explode I started to tell him to pull out, but then remembered an earlier conversation about his vasectomy. Moments later I felt the familiar feel of warm sperm entering me. I enjoyed it for a bit and then took his hand in mine and directed his fingers to my clitoris and we caressed it together until I came. I looked down at my husband the entire time.

Mr. Computer Nerd backed away. I snubbed out my cigarette and turned around. He had a frightened look but I smiled, kissed him on the cheek and said as if nothing happened, “why don’t you come down in a little while and join us at the pool.” I grabbed my bottoms off of the deck floor and whisked by the confused man to the bathroom. I dried off of his cum that had started to leak out and then put on my bottoms and headed out the door. I remember telling him to close up on the way out and went down to join my husband.

As I walked toward my gorgeous husband on his lounge chair I pulled off his t-shirt that I was wearing exposing by breasts (I was the only topless woman that day for some reason but didn’t care), leaned down and gave him a long wet kiss. I felt more leakage so I jumped into the pool to hide the wetness on my suit.

Our friend did join us about 20 minutes later. He tried to act normal as we took turns playing backgammon against each other. He was obviously distracted and lost every game, maybe because he was playing with a topless woman he had just fucked, and her husband who had no idea.
The next day he was well enough to go diving with his friends and another room had opened up in the dive resort so he moved down with them. We never saw him again.

As for me, I have no idea what to think about the episode. In less than the time it took me to smoke a cigarette, I risked 18 (at the time) years of marriage and my life as I know it. While I know in my logical engineer mind that I cheated on my husband, I don’t really feel guilt. I feel as if I just “out-naughtied” him on that vacation.

The rest of the trip I was a wild animal. After we left the pool that day, I re-lived the episode on the deck with my husband although he thought it was just a new variation on our vacation sex, after all, we had fucked every other place in the room. He had no idea that my wetness inside was only partly due to my excitement and partly due to the fact that his penis was literally swimming in our new friends cum. We spent the rest of the vacation much more in the room than out, and had the best sex of our lives. That continued weeks and months…. and even years after we got home.

It was a strange set of events that never would have happened if any number of things hadn’t lined up perfectly - if I hadn’t finished my book at that moment, or had the door closed all the way when I went in to get my book, or had there been another smoker on the pool deck that day (as there was every other day) and I would have felt comfortable smoking there like usual, or had Mr. Computer Nerd taken my mocking as a joke, or had he not been too stuffed up that day to go diving, or had there been enough rooms at his resort, or had my husband been sitting on the other side of the pool like we had all week with the possibility of seeing into the room – neither of us never would have chanced it……had any one of those things been different I never would have had another man’s penis inside of me. I was certainly not looking for anything like that to happen….but it did.
That was three years ago. I have not had sex outside the marriage since and I sincerely believe that I never will again as I have no desire to do so. I still feel no guilt although my mind tells me I should. What came out of it was an exciting memory that fuels my drive for sex with my husband. He has noticed the change and loves it.

Somehow, someway things came out better than if it hadn’t happened. I guess I just dodged a huge bullet.


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