Catching Up With My Ex Secretary



What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Los Angeles
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Motion Picture
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? N/A
How many sexual partners have you had in your life (including oral sex)? 75+
How many hookup stories have you here posted before? 0

Catching Up With My Ex Secretary

How long ago did this hookup happen? 6 Months

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

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? She was a tall brunette with the greenest eyes I’ve ever seen and a wide bright smile. I’d say she looked like your perfect country/cow girl from a “farmers only” commercial.

I knew her very well as she had been my secretary 6 years earlier. She worked for me for about 3 years so I’d known her a total of 9 years. We’d stayed in touch over FB or email but purely platonic in nature. We had flirted in the past…maybe kissed for a moment during a holiday party but nothing serious.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I saw on her social media that she was going to be in town so I asked if she wanted to get together to catch up. She did so we arranged to meet at a sushi bar in the late afternoon around 3pm on a weekday. I’m not expected home from work until 6 or 7 so I knew I had plenty of time to get together and still make it.

She looked great and we fell immediately into talking like old friends. She’d gone on to get a degree, was dating a man in Washington and life had been going very well for her.

As we drank saki and ate sushi I was becoming attracted to her in a way I hadn’t ever really thought of. She was just so damn sexy. It might have been the drinks but I am sure I could see the twirl of a finger through her hair or the cursory downward glance in her eye that seemed to signal she was feeling the same way.

After paying the check I suggested we go for another drink nearby. There is a very nice outdoor hotel bar a block away so we went in and started drinking margaritas in a cabana by the pool.

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? As we drank we sat closer and closer. We professed past attractions to each other and the flirting and suggestions were definitely getting heated. Our hands were on each others laps/thighs and eventually I just leaned in and kissed her.

She reached down and rubbed my crotch as we let our tongues explore and the kissing was quite passionate. I felt her large breasts under her loose sweater, she continued to rub and grab at the bulge in my jeans.

This was getting serious but nobody could see us. I went to the bar and got us our third drink and they were pretty strong. If I was feeling this buzzed she must have been too. But I was loving it and wasn’t about to ruin a good thing.

I put the drinks down and we started sipping for a minute or two when she said she had to go to the restroom. I did too actually so we went together across the yard. She went into the W room and I went into the M room.

As we came out pretty much at the same time I reached over to hold her hand and said “C’mon…” and we both went back into the W room. We were giggling and laughing as we started to kiss against a wall with our hands all over each other.

Out of the blue she unbuckled my belt, unbuttoned my pants and yanks them down to my ankles. As she was already down there she took my cock into her mouth and started to suck and lick me. I was rock hard and didn’t want to cum so I gently tugged at her to stand back up.

When she did she immediately pulled her pants down to the floor. I was a little shocked because it was such a bold move. There was no hiding the ‘just fuck me already’ mood. To be honest I was nervous now feeling a little put on the spot.

So I kissed my way down to her pussy and licked it for a brief moment and then stood up so that my cock was pushing against her.

We started to kiss and she reached down to rub the tip of my cock against her and to grind it a little inside of her. It was an intensely hot moment. I’d never really done anything quite like this.

Just as I was pushing into her there was a very loud knock at the door. Our eyes must have popped out of our heads as we both looked at each other in a half shock half laugh trying to be quiet but also trying hard not to crack up laughing.

Here we are up against the wall, our pants around our ankles, her shirt pulled up and over her breast and my cock half inside her with her left leg over my hip.

The knock came again with a man yelling, “Excuse me….You cannot be in there together. You cannot be in there”.

We stayed totally silent. “You cannot be in there together…HELLO…are you in there?”

My secretary finally said, “Just a minute” as we started to quickly get dressed.

When we opened the door there was a hotel security man standing there, “You cannot go in there together, I am going to call more security, are you guests here, what room are you in, you can’t be in there” he kept saying as we walked away giggling.

I looked over my shoulder and said “Relax, we weren’t doing anything…we’re just having a drink and goofing off” and with that he seemed to chill out and watched us go sit back down and start drinking.

We had a good laugh about that, finished our drinks and before we left she asked me if we should go get a room and finish. I wanted to so badly but I guess I also felt that no good could possibly come out of taking that step. It was fun while it lasted, I was halfway drunk and probably smelt like sex. At least my guilt did even if I knew I was fine making it home.

That was it….hot as hell but just a great story about a moment in the end. nothing more happened. We’ve stayed in touch.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I have never forgotten the incident and there are times when I wish it went further. I felt fine. Happy that I wasn’t caught but turned on by the attraction and the memory. It’s all good. I have nothing but good thoughts about her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody until I am writing this.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The spontaneity.

What was the WORST thing about this hookup? Getting interrupted. But maybe that was also a good thing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? N/A

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? I find this project to be a very interesting study. I am assuming people are telling truths and with that assumption it’s a way to better understand that everyone has secrets, everyone has sex, everyone has feelings and that things are universal even if not identical.

Makes me feel good reading these accounts.

You have a hookup story to share? Submit it here!