by TM

Gender: Male
Age: 43
Race/ethnicity: White English
Current location: Chicago
Highest education received: College degree (eg., BA, BS)
Occupation: Own a PR Firm
Relationship status: Married
Religious affiliation: Catholic
How religious are you? Very
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 21
How many hookup stories have you here posted before? Two

I Married her Friend

How long ago did this hookup happen? Almost Five 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…)? Weekend Fling

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? Lindsay was a tall busty, leggy blonde in her mid twenties.  She was a lounge singer at a bar a few blocks from where my office was then so I was in there a lot.  I found her talented, charming and attractive and had spoken to her a few times as I was a regular there.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had gone into the pub for a drink on a Friday afternoon as I often did. I had picked up a few women here before but wasn’t really looking to that night.  Lindsay had sung her number and sat down next to me at the counter between sets.  She was direct enough to ask me if I wanted to buy her a drink and I said yes.  She had on a rather tight black dress and I noticed how it flattered her curves.  We talked a bit and she asked if we could go back to my place since hers was being remolded.

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? We ended up in my bedroom and kissed a little and I could tell she was a bit nervous.  She asked me to help her out of her dress and I did so and she then took her bra off and asked me to lay back on the bed.  She blew me and was quite good at oral, it took me a while to finish and I had a rather intense orgasm.  She then rinsed her mouth out and asked me to do the same for her.  I pulled her panties off and ate her until she came.  
We relaxed in bed a while before going again, and this time in just standard missionary.  I sucked her breasts a little and kept kissing her in between and then penetrated her.  I couldn’t finish this time, I am older now but Lindsay did orgasm again.  
We fell asleep after that and had sex again in the morning, again missionary.  Basically we spent all day Saturday and Sunday in my flat alternating between watching Netflix and having sex.  We did in missionary, cowgirl, doggie and also a bunch of oral.  We took a bath together as well.  Monday morning she showered and kissed me goodbye.

Did you have an orgasm? Did your partner(s)? We both did a bunch of times over the weekend.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We had both tested clean, we discussed it and Lindsay was on birth control.

What were your REASONS for having this hookup? I was horny and wanted to.

Were alcohol or drugs involved? If so, how much? Few drinks each, not much

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? I had fun with Lindsay so I tried calling her a few times but we never hooked up again and a few weeks later Lindsay started singing at a different lounge.  I decided she was just another hookup and decided to move on.
I met my second wife a few months later and quickly fell for her.  We had been seeing each other for about eight months, things were getting quite serious between me and my future wife when she wanted me to meet a close friend of hers who turned out to be Lindsay.  Seeing her again was awkward but both my future wife and Lindsay were pretty cool about it.
Lindsay was a bridesmaid in our wedding and ended up marring a friend of mine.  We are friends now, and she is still pretty close with my wife.  However my wife is pregnant right now and had become sexually unavailable and since then I have noticed the return of my wandering eye and it has been Lindsay I am thinking about.  I have been keeping my distance as it was a friend’s wife I had an affair with during my first marriage (See an Affair to Remember).

To whom did you talk about the hookup? How did they react? I told my future wife who was pretty upset at first but also grateful that neither of us were willing to lie to her.  She also understands we all have sexual history.  Also went to tell my friend who told me that Lindsay had already told him when they started seeing each other.

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

Do you regret this hookup? If so, why? A little, I think if Lindsay had never hooked up I wouldn’t be thinking about her in a sexual way now.

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? A weekend of good sex.  Worst part has been that I am thinking about Lindsay sexually now even though I am happily married.  I have been trying not to and have been seeing a therapist about it, I don’t want to cheat on my wife while she is pregnant.

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

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

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