Incidental Relationship

INCIDENTAL RELATIONSHIP

This is a novella about a young man falling into an unexpected relationship. It is long, not packed with sexual depictions so if you are looking for raunch this is not for you.

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I was on my third business trip. I had gotten this great job with one of the best cyber security companies. I am an information security specialist. I graduated high in my class and I worked as a white hat hacker on the side. I'm Carlos, 25 years old. People tell me I look a little bit like Mario Casas.

I was staying at this hotel and went down to the bar one evening to have a drink. There were women everywhere. They were loud and having fun. Many groups off to themselves living it up. I ordered my drink and this lady came up to the bar beside me to order a drink. She looked at me and said, "aren't you cute?"

I looked at her and said "thank you, you're cute too." I've never really been good with women. I've spent most of my life behind a computer, leaving my social skills a little lacking. She ran her fingers through my hair and said, "nice but I could make you look hotter".

She stayed, turned toward me and we began to talk. I really should say she talked - a lot, and told me she was there with a cosmetology convention or something. She explained that it was a beauticians or hairdressers meeting. She was 31 years old, had two kids and was not happy in her marriage. She didn't like where she worked but liked the money. I assumed she was quite drunk to spill such information to me in this short time.

Before I totally realized what was happening, she said, "let's drink these in your room where we can have some privacy." She winked at me, wrapped her arm in mine and headed us to the elevators. I may be socially awkward, but I knew what was going on now. I looked at her and she was nice looking. Had a nice body and I thought what the hell.

She talked all the way up the elevator and to the room. When we entered the room, she immediately started taking off her clothes. She was saying how nice it was to get away and have fun anyway she wanted. When she was down to her panties, she looked at me. "Oh honey, you're still dressed." and started taking off my clothes.

When she had all my clothes off she looked at me and said, "damn I hit the jackpot. Nice cock."

She then knelt down and started sucking me off. After I cam in her mouth and she swallowed every drop, she laid down on the bed and said, "now your turn." She had a completely shaved pussy and so I felt obliged to return the favor.

After I ate her pussy, we fucked two times, I should say she fucked me two times and then she got dressed. She kissed me and said, "You were great stud. Thank you. I needed that." And walked out of the room.

It all happened so fast I laid there trying to make sense of it all. Really it didn't matter. It was great. It was really good sex, so I was not going to look a gift horse in the mouth. I passed out and slept like a baby.

I checked out the next day and flew to my next destination. My job required an insane amount of travel. The next two hotels were boring with nothing exciting happening. I often thought about that night and how it happened. At my next hotel, there happened to be a dental hygienists conference going on.

Again that night, the bar was full of women. I struck up a conversation with a pretty lady at the bar. As we talked, she revealed that she was divorced and there alone. She was not as bold as the last lady but I thought she may be looking for the same thing. Due to my inexperience, I was not sure. In hindsight she was making it clear she was available and waiting for me to make the first move.

She saw that I was not getting the message, so she started asking about my relationship status. When she found out I was not married and didn't have a girlfriend, she said. "How does a good-looking man like you not have women falling all over you?"

When I still didn't take the bait, she decided she had to take some initiative so she said, "It's getting late. Would you mind walking me to my room?" I quickly agreed and began to think I was right about her intentions.

When we got to her room, she opened the door and almost pleadingly said, "would you like to come in for a bit?"

I said, "absolutely." I put my arm around her waist as we walked toward the bed.

She put her hand on mine holding it in place and turned toward me, which put her in my embrace. She said, "I hope you don't think I'm a harlot or something but It's been such a long time since I've been with a man. And you seem so nice and you are so damn good looking."

"I think you are fantastic," I said and kissed her. We had sex and I spent the night with her.

I had started to figure out the sequence. These conferences, training sessions, and meetings of organizations that were mainly consisting of women were fertile hook up opportunities. With my heavy travel requirements and devoting so much time to work I didn't have an opportunity for a steady girlfriend. So I would search the internet for these types of meetings in the cities I was traveling to and pick out a hotel that either housed the event or was close to an event.

The plan was perfect for me. It gave me an opportunity for uncommitted companionship and great sexual fulfillment. I never would consider employing a hooker. I was too awkward for that and the chance of catching a communicable disease was too great. These were everyday women, housewives, moms, daughters, professional working women. They were clean, well dressed, interesting and I figured the chance of catching anything was low. Also, there was no commitment. No relationship that had to be maintained.

It worked great. I didn't get laid every time, but it was still more exciting than just staying in a boring hotel. The women were always nice to look at and the atmosphere was fun and playful usually. More often than not, there were at least several women who, being out of their humdrum lives and away from home where no one knew them, were looking for some excitement, usually in the form of sexual fulfillment.

As time went on, I got very good at picking out which ones were looking to get laid. Also, I had improved my social skills. It was great for my ego and I became quite confident. I got good at knowing how to talk to women and what to say. I even started to figure what types of groups would be more adventurous and uninhibited.

I wasn't able to find a female saturated conference every time, but I had become assertive and became good at picking out women who would be open to some sex while away from home even if they were by themselves. I would see a woman at the bar or in the restaurant and have a pretty good idea if I could pick her up. I was surprised how many women were not only willing to have sex with someone they had just met but were looking for it. My sex life had increased exponentially.

Believe it or not, in time straight sex got a little boring. So, I tried to expand my horizons. By picking the right groups I had the opportunity to fulfill a lot of sexual fantasies. Including a threesome, light bondage, role playing, etc. I found that some of these women that had gotten comfortable with having affairs were looking for the same type of thing. I felt like I was living every man's dream.

It's funny how the mind works and how eventually we get bored with something that at first was so exciting. I had become so adept at choosing the right environment, the right person, and the proper tactics to use, it was no longer a challenge. That's when I took up my new approach.

My new approach was to avoid the easy targets. Instead, I would look for the woman that probably was unfulfilled but had not planned on looking for a sexual encounter. This certainly presented a challenge and meant less success. But I could always revert back to my old ways if I just needed some sex.

For some reason I found great fulfillment in this approach. It was so rewarding if you were able to bring out repressed sexual desires in a woman that she maybe didn't even know she had. And the sex with those women were different. It was not always wild animalistic sex, although sometimes it was. Usually, it was loving appreciative sex. Once they gave into their desires, not only did they seek to satisfy themselves, but their partner also.

It turned me on, how bashful they would become right before giving in, which even emboldened me more. The challenge also was to give them the greatest orgasms of their lives, which oftentimes was not too hard.

Cindy was a great example of this. She was at a legal assistant conference. I first saw her at the complimentary breakfast at the hotel. She came in alone and sat alone. She was looking at a notebook while she ate breakfast. She was a nice-looking woman in her mid to late 30's I estimated. She had a nice average build. She was wearing a wedding ring. Your typical, suburban, middle aged housewife type.

I purposely went up to the buffet when she did. She was getting an apple to take with her. I reached and took one as she did and struck up a mini conversation. I said, "I like getting one too, for later on." She looked at me and smiled and said, "yes, it feels a little like stealing but I know they are complimentary."

I responded with, "yeah it's fun to feel naughty, especially when you can get away with it."

She looked at me quizzically, smiled and said, "I guess that's it. You know sometimes I don't even eat them." and laughed.

I thought, ok good target. It just so happened I was able to work from my room today. I had picked up a schedule of their events from a table and at their lunch break I walked down to see if I could see her. She was standing in line with some other ladies waiting to enter the room set up for their lunch.

I had put the apple in my pocket before going down in case I saw her. So, I walked toward where she was. When she looked at me, I waved the apple at her and then took a bite and made a face like I'm being naughty. She beamed a big smile and chuckled. I made a little tip of the hat jester at her and walked on by. I could hear one of the ladies with her say "who is that" as I was walking away.

When I walked a little further down the hall I looked back. She and two other ladies were huddled together. I'm sure they were gossiping about me. I saw her look around and as our eyes met, I smiled.

Later before their evening event I lurked in the lobby where I could see the elevators from afar. When I saw her get off, I walked that direction as if I were headed to the elevators. She looked great. She had dressed up for the event as most others had. She was by herself so as I approached her, I said, "wow, you sure clean up nice for a thief."

She laughed and said, "you're not such a bad looking thief yourself." And then immediately blushed. I think I had surprised her and she blurted out what came to mind.

I responded with, "I'm flattered. I hope you have a good time tonight." and I headed onto the elevator. As I turned after getting on the elevator, I saw her quickly glance back and smile. This was turning out pretty good. I just needed a few more lucky breaks.

After supper I sat at the bar waiting for her to show up. Her event was supposed to end at 8:00 and if I were right, she would show up shortly after. I saw some I recognized from her group start to filter in.

Then I saw her come in with a few other ladies. They were chatting and laughing. I noticed her slyly looking around the bar and I suspected she was looking for me. I was facing the bar with my back to the door, but there was a big mirror behind the bar. I pretend I didn't notice her as she finally spotted me. I was trying to figure out how I was going to be able to cut her out of the group as they sat down together at a table.

I was able to keep a close eye on her without being obvious by looking through the liquor bottles and into the mirror. I saw her occasionally looking over my way. Then my break came when she and one of the other ladies got up to go to what I assumed was the bathroom. Why do they always go in pairs? But this was my chance.

I got up and made my way toward the bathrooms. As I bumped into them, I said, "well there's my little thief. We've got to quit meeting like this." We both laughed and the other lady said, "oh, do you know each other."

Now I immediately recognized this lady to be one of the types I had since moved on from. I guarantee I could have had her in my room within the hour if that is what I wanted, but I wanted the more challenging one. I quickly answered her question, "No, I have not had the pleasure of formally being introduced, but we seem to be two ships passing in the night that continually bump into each other." We all laughed.

The flirty one said, "are you here alone?" I confirmed that I was and she said, "well come join us. No one should have to drink alone."

I told her I would accept, only if I could buy the next round for the table. It was agreed and I was told to wait for them. When they came out of the bathroom giggling, they caught themselves and ushered me to their table.

I was introduced to all the ladies. It was then when I first learned her name. It was Cindy. I don't even remember the names of the other two, but the flirty one was Jane. We exchanged the normal pleasantries. They told why they were there and a little about what they each did. I told them who I was and what I did. They all thought that it was very interesting but I tried to play it down.

Jane, the flirty one, made it clear how attractive she thought I was. I rolled my eyes at Cindy when Jane said that. The other ladies indicated their agreement to the statement. I made it clear without being overly obvious that my attention and focus was on Cindy. I could tell Cindy was flattered by this because one of the other women was drop dead gorgeous and Jane, who also was nice looking and would have been a catch in my old days, was clearly fishing for a paramour.

I bought a second round of drinks over everyone's objections, and soon Cindy and I were conversing almost exclusively. She had a great personality and was witty and charming. Although reserved, I could tell she had a bit of adventurousness to her.

Slowly one by one the other ladies excused themselves, to either call their husbands or retire early. All except Jane. I clearly had become her target and she continually interrupted my conversation with Cindy. I would roll my eyes at Cindy each time Jane would flirt with me. I could see Cindy struggle to contain a chuckle. Eventually Jane gave up and said with disgust, "well, I'll leave you two love birds alone." and huffed off.

Cindy and I laughed when Jane was out of earshot. Cindy said, "I think you spoiled her night. I think you could have taken her back to your room anytime you wanted."

"Well, I prefer my naughty little thief." And Cindy blushed and almost swooned. She was thoroughly enjoying such lavish attention that she apparently rarely got.

We sat and chatted and got to know each other. She made it clear in the conversation she had a husband and family. I got the impression it was as much to remind herself as it was to inform me. But as I explored the topic, she tried to not let on, but it was obvious her life had become somewhat dull and she felt her husband didn't appreciate her or had started to take her for granted.

I eventually got the conversation around to us talking about our interests and what we like to do. What music we liked and it was amazing how much we had in common even without the addition of what I pretend to have in common with her.

We talked until they called "last call" at the bar. Cindy said, "gosh where has the time gone, I didn't realize it was so late."

I said the old line of "times flies when you are having fun. And Cindy, I have had a wonderful time tonight." I looked deeply in her eyes and held her hands and said, "I am so glad I've gotten to know you. You are an interesting and charming person. I don't want this evening to end and I am sick to think I will probably never see you again." I could tell she melted a little with these words.

Then I stood up, held out my hand and said, "shall I walk you to your room?"

She said, "Carlos, you know I'm married."

I said, "your husband is not here to see you safely to your room. It's late at night and in a hotel far from home where no one knows you. I think a beautiful woman like yourself requires some company."

Without taking her eyes from mine she stood up and took my hand. We held hands as we walked to the elevator and to her room. She didn't say a word as we walked. I imagined she was trying to decipher her feelings and what she was going to do about them. She'd had no intentions of anything but attending her conference. Meeting me and my obvious interest in her had taken her by surprise.

When we got to her door, she opened the door and then looked at me. I looked at her and said,

"Well, my naughty thief, since you have stolen from me, I wonder if I might steal something from you?"

"Oh, what have I stolen from you?"

"My heart."

"Aww, and what do you wish to steal from me?"

"A kiss, just to remember you by."

She blushed and looked down. I could tell she was conflicted. Then she looked up at me with wistful eyes and said, "not out here someone may see us." Then she grabbed me by the shirt and pulled me into the room. When the door shut behind me, she then opened her arms.

I embraced her and kissed her soft and lovingly. We held the kiss for some time.

When I broke the kiss, I looked at her lovingly and held her cheek in my hand. "Cindy, you are lovely." I then kissed her again. This time more passionately. She did not resist.

I broke the kiss and looked deep in her eyes. She had an almost helpless look on her face. Without saying a word I moved back in and kissed her again. This time I parted her lips with my tongue. She accepted my tongue into her mouth and we kissed with extreme passion.

She broke the kiss this time. Breathlessly she said, "Carlos I shouldn't."

I ran my hand lovingly up and down her arm. "Cindy, I feel such emotion for you. We connected and I may never see you again. I just want to make the most of our only night together. I think you feel the same way." I kissed her again. She resisted at first but then gave in and kissed me back. We kissed passionately and longingly. She still fought with herself internally and pushed me away again.

"Carlos, I don't want to cheat on my husband." In almost a whisper.

"Cindy, do you want to have sex? I only asked for a kiss." I said it in a joking way and smiled real big.

She slapped me on the chest and said, "oh you." Then she kissed me. For some reason this released a lot of her resistance and the kiss was even more passionate from her. I ran my hands up and down her back and eventually caressed her ass. She offered no resistance. I pulled her body tight to mine, pressing my hard cock into her. Letting her see how much she excited me. She moaned into my mouth.

I positioned so that my cock was over her pussy and began to lightly thrust into her. We were kissing, our tongues playing in each other's mouth and I was dry humping her. She was breathing heavily and I could tell she was extremely excited.

I moved a hand to her breast and as I closed my hand upon it she moaned heavily into my mouth. I could feel her nipples were very hard even through her bra and top. I moved my hand so that her nipple was between my fingers, giving it added attention as I massaged her nice breast.

I started to unbutton her top. She turned her head to the side, took in a deep breath and said, "you know I should stop you."