Flirty Emails

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Status: Finished  |  Genre: Memoir  |  House: Booksie Classic
When two workings start to exchange flirty emails what happens afterwards.....

Submitted: October 25, 2011

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Submitted: October 25, 2011




The first thing I do when I get to work is check my email and I have to ask myself why?, why am I getting so excited, why am I looking forward to work, why all of these feelings when it’s just emails? I know the answer but I am trying to dismiss it, but it’s the same and has been for the last two months and it’s to see if “he” sent me an email, a new funny cute remark or a reply to what I sent him earlier. Here I am a grown woman and I am getting excited thinking about these silly emails. I guess these emails are better than thinking about the boy’s soccer games or my husband’s parents coming over for dinner. Oh did I forget to tell you that I am a thirty-four year old married woman and mother of two very rambunctious boys, well I am.  I will tell you a little bit about myself first and hopefully you will understand.  My husband is my high school sweetheart, the only man I have ever known, and I mean that in every way that it means, sexually and so forth.  I never thought about cheating on my husband that is until now.  I want or need to give you a little bit of background before I go into my story, because I know that by the end of my story many of you will think differently of me, maybe some of you will understand and not dislike me.

I met my husband Alan in our senior year of high school, he was cute, and I thought it would be nice to date him have fun but things got serious.  Alan and I continued to date throughout college and after we graduated we did what was expected of us, we got married, started out careers, bought the house and had our children. I never thought that we would d do the suburbia thing but that is exactly what happened.  I love my husband I really do, he is a great dad, a great husband but somehow along the way I started to fantasize, well I have to be honest, I only started to fantasize when I started emailing my co-worker.  I started to look at this other man and wonder what it would be like to just have sex with him, just sex nothing else, because I don’t want to end my marriage, I just want to know what it would be like sleeping with him.  I never did this before I never fantasized about another man not until that first email and then my fantasies start to come alive, with Matthew my co-worker.

Matthew, how do I begin to talk about someone I really don’t know, we have somehow become email buddies. I have to be completely honest, he started the flirty emails, but I didn’t stop him, I chose to answer them back in my own flirtatious way and we continued on and now we have come to the crossroads of “what are we going to do next?”  I know I should have stopped the flirting with the first, LOL, or the smiley faces or even at the …… at the end of our sentences, but I didn’t.  Again, it’s not as if I am lacking anything at home, I’m not and I know some of you may find that hard to believe, but it’s true.  I am not being ignored physically or emotionally, my husband is a fantastic man and Matthew doesn’t fill a void, the simple truth is that I just want him.  Society will most likely judge me or even want to brand me with the scarlet letter “A” across my chest, but I have to be honest and “Really, am I the only woman who has felt this way?” Hasn’t anyone just wanted to have a sex with a man and with no other expectation but just sex? Well I have and I am thinking of it and I want to act on it.



The emails between Matthew and I have really picked up recently and I am getting more and more excited when I think about them.  The emails have so many underlying innuendoes that we can no longer play the “innocent” card, we are trying to see who gives in first.  I think this game of “chicken” that we are playing with each other comes from both of our fears that just maybe, maybe the other person doesn’t realize that they are flirting and how embarrassing it would be if one of us said something and the other is offended.  I should tell you more about Matthew before I go further.  Matthew is a married father of three and has been married for about fifteen years and I think he is happy, I really don’t know because we just don’t discuss the topic of our spouses.  I think Matthew was just as surprised by our email flirting, he really doesn’t seem to be the type to go down this road, but then again, neither was I and yet here we find ourselves.  We have both met each other’s spouses at various functions at work and his wife is very likeable, again I have to stress that both of our spouses are really nice people and again you are probably wondering “then why are we doing this?”

You all may wonder, “What could they email about” and the answer is quite simple, we talk about everyday stuff with a twist to it.  I wish I could share some of the emails, but alas I cannot because then Matthew will know that I am writing about this publicly and I am not ready to end our email relationship.  I will say that the first signs of attraction were when he said to me, “I enjoy coming to work, look at what I get to look at” and I said back, “you’re not so bad looking yourself”, and of course this is all in a playful joking way.  The sign that this flirting was more than flirting, were the looks we exchanged afterwards with each other, the glances throughout the day and the passing flash of pure sexuality when looking over each other, we could not deny the attraction.  Does attraction mean that you’re not in love with the person you are dating, engaged or married too, at one time I thought so but since I am now experiencing this, I have to say “NO.” 

As I said earlier, the emails have really picked up not only in quantity but in innuendos and I have started to think about how we can meet, how it will be possible to get away.  The truth is I am not sure if I want to have a full out sexual encounter with him or just a brief hook-up to get this out of my system and I blame this dilemma on society.  Society has made us women feel as if we need to rationalize our wants and needs and if we “women” choose to cheat on our spouses we need to have a valid reason we need to “rationalize” our actions.  The truth is I don’t have a reason, I don’t have an explanation as to why I want to sleep with this man.  I know that these emails can’t continue on without any further action because we are both becoming sexually frustrated and I know that he wants me to make the first move and I know I need to either end it or take it to the next level and I know what I need to do, but is it what I want to do?

I really crossed the line and yes I know many of you said I did that when I started the flirty emails with Matthew, but no I have finally crossed the line. The other night while I was in an intimate moment with my husband, I thought about Matthew, I imagined that it was him behind me, him grabbing my breast and holding onto them while sliding in and out and the orgasm that followed was strong, stronger than I had in a very long time, not better just stronger.  This has to end and I have finally decided to take the next step, I sent Matthew an email asking if we can meet for lunch and he replied, “Yes.”


Matthew and I went to lunch in a very public forum because the last thing we want to do is to draw attention to ourselves by leaving the building so we ate in the building, just far enough away so that no one can hear our conversation.  I have to be honest that there was a bit of awkwardness between us and I know many of you will find that odd, since our emails are full of innuendos, but there was and it was kind of cute.  Matthew looked at me and said that he was starting to think more and more of our email conversations than he ever thought he would and I believe him because I was doing the same thing.  Before many of you start to think that he is trying to play a game or act reserved with me understand that this whole thing just snuck up on the both of us and now it’s becoming reality and we don’t know how to handle it.  We both decide that we need to see each other outside of the office.  I suggested that we meet at a park that has a great hiking trail and I was pretty familiar with it because I grew up right next to it and we could have some privacy.

I met Matthew on that Saturday at the park, he parked his vehicle and we started out down the path without saying a word to each other.  I finally broke the quiet with telling him to veer off the path down to an area that I know was pretty secluded and only the locals were familiar with the area.  We finally got to a place where part of it was covered by trees but an open area sat in front of it so you could either sit under the trees or sit out in the open area and enjoy the view.  Like two thieves in the night, we chose to stay hidden under the trees to talk about what was or not going on with the two of us.  I started to say something and the next thing I know Matthew is pushing me up against the tree, his mouth over mine and his tongue in my mouth, my hands creep around his waist to pull him in tighter to me.  We finally break for air and we just look at each other and we could both see that we are not sure why we are doing this, why are we risking everything for this, it’s not as if we are in love, it’s not as if we are going to walk away from our families, what are we doing and the simple truth is we are just feeling.  I grab Matthews face and bring it down again to mine and I tell him that I want him, I want him inside of me, I want him to fuck me and I don’t want to think, I just want to feel him.  I got my answer when I felt his cock harden against my leg and he moved it between them so that I had no doubt what he wanted from me.  We both knew that we were not going to have sex right there, first what a cliché and second, anyone could see us and neither of us are exhibitionists.  We both decide that today was neither the time nor the place and most importantly we had to get back to our families.

I went to work that Monday and call it what you want but when I received an email from my supervisor telling me that I would be attending some training in Baltimore the first thing that I thought of was that this would be a perfect opportunity for Matthew and I to finish what we started in the park.  I emailed Matthew and asked if it were possible to meet me in Baltimore, I would get in the day before the training and we could be alone.  Matthew came back with a solid “yes” and it was settled, we went from being email buddies to I am not sure what we are becoming.  I never had any intentions of having an affair, but here I am planning a night of pure sex with this man and right now I need to end this sexual frustration, maybe after this it will be out of my system and I can go back to being normal.

I am not sure what Matthew said to his wife and I didn’t ask I just know that when I got into Baltimore, I saw Matthew parked in the parking lot of the hotel.  Again, I guess I was being deceitful, but I chose a different hotel to stay at instead of the one that the Training was being held at so I could have this illicit sexual encounter with Matthew.  I checked in, he followed, no words were said and we went to my hotel room.  I could have told him that I have never done this before that he would be my only second lover or whatever excuse women use to rationalize what they are doing, but I didn’t.  I walked into the room first he shuts the door, I turn around and start undressing with him staring at me.  Where did this confidence come from, I am not sure, I mean I still have a youthful body, my breast are still full and firm and I make sure to get my waxing done on a weekly basis, a woman should take care of herself but now here is this man, practically a stranger looking at me as if I am the main course dinner and he is starving.

I guess I could go into detail but I won’t, I will say that I was in control of our day and night together.  I led him to the bed, I undressed him, I straddled him and I came long and hard before he did, I wanted to feel him inside of me and I did, I wanted him so bad and it was so damn good.I had this fantasy about the two of us being together, making each other feel things that we shouldn’t but did. I take full responsibility for this day and I wish I could say that it ended that night.  That because I fulfilled my fantasy I could go back to the way it was, but I can’t and I won’t lie to you.  What Matthew and I have some may call “an affair”, but we don’t talk about “love”, we don’t talk about “what ifs” we honestly don’t talk much we just feel, we come together when we can, we don’t make promises we can’t keep but the one thing we won’t give us are those silly flirty emails that started this all…

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