My First Affair, True Story Part One

Posted in: Affairs | True Stories

This is a true story which I think I have wanted to put down on paper for some time but never really had the right forum until now.  I am also inspired by another writer sharing true stories.  Let me start by telling you a bit about myself.  I am a 46 year old happily married man and have been for twenty years.  I think I have always been a little shy which makes people think I am reserved.  But I’m actually not reserved inside (as you will see) I just need the right person to bring out the wild in me.  I was probably what you would call a nerd in school, and as an adult I have always worked hard to get ahead.  Being shy, I have to be honest here and say that I got married too young to the first girl who showed any interest in me, I will call her Gillian.  Having said that, I have to make clear that I am not unhappy in my marriage.  I have a good life with a great partner and family and an excellent sex life.  I am a natural perfectionist and so even though my sexual experience was limited, I learned and practiced every technique I could read up on to the point that I prided myself on being a great lover.  I have never been shy between the sheets and we have always been willing to try different things.  But my wife would never be interested or approve of anything involving any other partners, so I always knew that was off the table.  After the first five or six years I hinted occasionally but no interest, so I dropped it and enjoyed things as they were.


I had occasionally thought about the possibility of having an affair, but the prospect of what you could lose always haunted me.  The other thing that really concerned me about having an affair was whether I would be able to look my wife in the face while making love to her, the thought that I might ruin what I have even if I managed to keep the lie going.  I used to worry that I would feel guilty and would have trouble getting it up.  But it turned out to be completely the opposite.  Ironically I later found out that having an affair is the greatest aphrodisiac.  Nothing makes me harder than the thought of pounding my wife after I have already emptied a load in my lover’s welcoming pussy just an hour or two earlier.  Nothing is as hot as being inside of my wife without her having a clue where I have been.  You haven’t lived until you have your girlfriend giving you a blowjob or riding you while at the same time you nonchalantly chat with your wife about how sick you are that you just can’t leave the office right now.  And this may just be my way of justifying myself, but I honestly believe that my wife gets bigger and better orgasms as well because my extra curricular activities keep me so horny all the time.  But I am jumping ahead.  Let me tell you how this all started.


Shortly after getting married we moved across the country for my career and things have gone very well for me.  Without wanting to go into too much detail, I manage a local branch of an insurance agency that has grown a lot over the years, but my small branch still has less then ten people in it.  About ten years ago at the time that my business was really starting to expand I was feeling pretty good about myself.  When the company was smaller I always did my own typing and filing and well basically everything in the office but as we expanded and had additional agents in the office I now needed to hire an office secretary/assistant/receptionist for the first time.  I called up the local agency and had them send me over their two top recommendations and I interviewed them the same day, one in the morning and one in the afternoon.  The morning one was professional and had all the computer skills and seemed perfect for the job and I was ready to hire her but went ahead with the second interview.  The second applicant, I will call her Jennifer, was one of the most beautiful women I have ever seen.  She was a stunning black goddess with the most wonderful brown eyes, full breasts and lips.  But the most wonderful thing about her was the way she carried herself.  She had confidence and vulnerability at the same time.  When I look back on it now I know that I wanted her as soon as I met her, but at the time (and bearing in mind how shy I was) I convinced myself to just go along and be professional.  But from the outset we had the most wonderful chemistry.  After the interview was over, I remember thinking through the options.  The first applicant was the obvious choice.  But I remember distinctly thinking to myself “I have worked hard and I deserve to have something beautiful in my life”.  This is not to say that at that time I had any intention of being anything but professional, I just remember on some level making the hiring decision based on a feeling rather than logic.  So obviously I hired her.


For the first couple of months it was quite professional, but thinking back on it she would wear these low cut tops which were not really appropriate and she would go out of her way to bend over the filing cabinet or desk or whatever right in front of me and would always somehow end up getting a great view of her breasts or her beautiful tight and full ass.  And all the while we had the most wonderful chemistry between us.  It was not long before she was occupying my thoughts a lot of the time and I knew that I wanted her.  However as I mentioned I was not very experienced with women and I was so afraid that I might be misinterpreting something.  My biggest concern was that I would cause the company to get sued for sexual harassment and lose the job I had worked so hard for, not to mention what effect that would have on my home life if it came out.  So for a number of months I just tortured myself.  Whatever she would do (and she later admitted she was trying to seduce me the whole time) I just ignored it and behaved professionally.


The next thing that happened was about four months into her employment.  I was leaving the office for an appointment across town.  Just as I was leaving she was doing one of her normal tricks bending over the filing cabinet flashing her breasts at me and she said something to me.  Unfortunately I can’t remember exactly what she said, but it was something like “Can I come with you?” or something like that.  But of course it wasn’t so much what she said anyway, it was the way she said it.  Of course I heard “Can I cum with you?”  I played it off again like we were having a joke, but all I can remember is that as I left the office and walked to my car, my heart was pounding.  As I drove to my appointment I kept running the conversation over in my head and trying to figure out what to do next, but at the end of the day I was still too afraid and just carried on as before.


The tension then continued to build for another couple of months until the storm finally broke.  It was a Friday around lunchtime and all of the other agents working for me were out of the office on appointments which happens at least once a week on average, so it was just her and I in the office.  We ate lunch in the office and chatted.  The next thing I know she is laughing at an email that a girlfriend of hers has sent her.  I asked her what it was about and she showed it to me.  It was a joke that was a little sordid, but not anything pornographic.  The email was mildly amusing, nothing to write home about, but it was of a sexual nature.  And so there it was.  All of a sudden the subject of sex was there between us.  I pretty much froze, not knowing what to do next, still afraid to make the first move.  I sat down in the reception chair facing her desk and we continued to chat.  Taking her cue from the subject of sex which was now in the air (and neither of us wanted to change the subject), she suddenly started to tell me that she was sexually frustrated because she was not getting any sex at home.  I was instantly hard as a rock and sitting right in front of her and it was obvious, so obvious.  I told her what a tragedy it was that she wasn’t getting any and that I think I said something like, “I would really like to help you with that.”


Now at this point you would think that I would have acted immediately and taken her right there and then, and if this were a work of fiction that is where we would go next, but this is absolutely a true story and it has some twists and turns, but trust me, I am getting there.  My fear was so great that even with basically an open invitation I could not move forwards and do anything right there and then.  Besides which I had not completely lost my head – I didn’t have any condoms.  I can’t believe this as I look back and write this now, but after chatting politely for a few more minutes I got up and walked to the bathroom.  My erection never faltered though and my manhood felt like it was sticking out a foot in front of me.  I waited in the bathroom until things returned to normal and then went back to my office.  I sat for about an hour trying to decide what to do next, and then one of the other agents came into the office so my opportunity was lost for the moment.


I went home hornier than I think I had ever been in the past.  Since it was a Friday I spent the weekend pounding my wife’s pussy and pretending it was Jennifer’s.  My wife seemed quite happy too because she had many good orgasms that weekend because of what was on my mind.  She may have wondered what got into me but she didn’t question it.  And so I had all weekend to go over everything and figure out what to do.  And I swear that is the only thing that occupied my mind all weekend.  Even though it seemed a perfect situation, I was still terrified that my whole world could fall apart.  Nevertheless, after wrestling all weekend I made the decision to go for it.

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