My Secretary

by John Doe

Gender: Male
Age: 36
Race/ethnicity: White
Current location: NYC
Highest education received: College degree (eg., BA, BS)
Occupation: CFO
Relationship status: Divorced/Single
Religious affiliation: Christian
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? One

My Secretary

How long ago did this hookup happen? Three Years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Affair

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Amber was a pretty blonde in her early forties.  She was tall, five ten with long legs, a toned body and a big chest.   She had worked as my secretary for about five years before we hooked up but I was still married when Amber started working for me and she was married as well.  I found her attractive and intelligent but as I said I was married.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I made CFO roughly the same time as my divorce was finalized a few months prior to this.  Since college I have spent most of my life and time focused on work, which was a big factor in my divorce.  I had spent a year separated from my wife where I had not hooked up with anyone because I had hoped to work things out with my ex-wife.
Considering I spent most of my time at work I guess it was not hard to imagine that my first two hookups following my divorce were women I met at work.  Amber was the second, a lot of late nights working together and her brushing up against me.  I began to find myself attracted to her and there started to be a certain degree of sexual tension between us.
About a month prior to our first hookup we had both gotten a bit tipsy at the office Christmas party and ended up making out a bit and feeling each other up.  We ended up in my car where she blew me.
Amber pretended like it never happened and changed the subject any time I brought it up.  For a month or so we went on like this but she did once lean over while in my office and let me get a good look down her blouse.  I finally cornered her and Amber admitted to being very attracted to me and that she wanted to hook up and we made plans to meet at a hotel.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I met Amber at the room that evening, she had on a short skirt and revealing top.  We talked for a few minutes, both a little nervous but we started making out and I undressed her.
When I got my hands on her breasts they felt a little weird and were hard.  Amber said she had them done a few years prior. I then penetrated her and rode her until we both came, just in standard missionary.  We decided to spend the entire night together and had sex again the next morning, Amber wanted me to bend her over the bed and take her from behind and I did and I came and she didn’t.  Afterwards we dressed and went to work separate.

Did you have an orgasm? Did your partner(s)? Yes we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used a condom both times we had sex that night.

What were your REASONS for having this hookup? Lust and desire and I really liked Amber.

Were alcohol or drugs involved? If so, how much? Not that time

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Amber and I carried on for about four months.  She was still married then, but miserable however she was unwilling to leave her husband as she had two children.  We had sex a lot, including in my office a few times.  Strong feelings began to get involved which was not something either of us were looking for at the time.  Amber finally broke things off saying things were getting too serious.  She asked to be assigned to someone else saying it was too hard for her to work around me after we split up and I got her a position with a VP.  
About a year afterwards Amber split with her husband.  I was approached by someone, evidently he had learned about our affair.   However they settled and I never was a part of their divorce proceedings.  I haven’t actually seen Amber in a few years as she works on another floor and I generally avoid her floor.  I look back together on our time together fondly though.

To whom did you talk about the hookup? How did they react? I have never really told anyone about this, our affair makes neither Amber or I look very good.

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes

Do you regret this hookup? If so, why? Part of me has always felt guilty about fucking a married woman, its not something I have done again.  I also lost a really good secretary.  I also did not care for the fact I nearly got pulled into Amber’s divorce.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Good sex with an attractive woman, worst part has been that neither of the secretaries I have had since Amber have been as good at the job.  As for casual sex, I learned it can be fun but it also can come at a price, and as a rule now I don’t fuck married women.  I also learned that some clichés are true for a reason.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Somewhat negative

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