Hookup With A Former Colleague



What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Montreal
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Obsessed
How many sexual partners have you had in your life (including oral sex)? North of 70
How many hookup stories have you here posted before? 3

Hookup With A Former Colleague

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

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? I work for a large corporation. One day, about 10 years ago, a new secretary (sorry: administrative assistant) was hired by our department. Let’s call her Marianne. She was relatively short (1.57m or 5’2″), blonde, with a pretty face, and beautiful blue eyes. She also had this very bubbly personality. We got along very well from the get-go, but I was not attracted to her at all as she was overweight and that’s an absolute turn off for me. Marianne is 15 years younger than me. I was 50 at the time, so she was 35.

One day, maybe 3 years into her time working with us, Marianne walked in front of my office, wearing a relatively short skirt. It struck me: this woman was sexy. Slowly but surely, she had been dieting and she lost 30+ kilos (around 70 lbs – she told me later). It’s really then that I started to feel a physical attraction. When I told her that she was pretty, her reply was: “I always felt the same about you”. Okay…but I have this rule: don’t fuck with colleagues (I did it once in the past and it did not end well – so I absolutely stayed away from affairs with colleagues ever since).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? About 5 years ago, Marianne resigned and went to work for another company. At that time, Marianne had a boyfriend and I did not attempt anything. A year went by, when one day I saw a post, from Marianne, on LinkedIn. I decided to give her a call, out of curiosity. She essentially told me that she liked her new job a lot and that she was single. I decided then to try my luck and I invited her on a dinner “date”. She knew I was with someone then. Long story short, during the dinner, Marianne had two glasses of wine while admitting she’s not very tolerant of alcohol. When we got out of the restaurant, we started making out and she invited me to her apartment. It took forever to get to her apartment, and as we were talking, I discovered that Marianne had some real psychological issues, especially regarding her relationship to her body. Even though she had lost a lot of weight and she noticed that more men than ever were flirtatious with her, she could not accept that fact. She essentially kept talking about her weight and her body for the whole time it took to get to her place. It really got on my nerve.

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? Well, almost nothing. After some preliminaries, we were naked in her bed. Her tits were a bit saggy, but overall she had a nice body. When I was about to fuck her, she pulled back. She told me she wouldn’t let me fuck her because we didn’t have any condoms. Okay…so I went down on her then, thinking she would reciprocate. After she came, she told me she refused to give a blowjob on the first date. Okay…so I put her on her back, on the bed, I climbed over her, and I guided her hand to my dick, hoping that she could at least jerk me off. Which she semi-reluctantly did. I had it with this girl. When I began climaxing, I took the matter in my own hand – literally – and I was aiming to shoot my load in her face. Better that than nothing. Most of my cum landed on the pillow, only a little actually got into her face. I was disappointed with myself because that was a fairly large load; her face would have been glazed quite well had I not miss my shot.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? We were supposed to get together again, but two days after the hookup, Marianne sent me a message to tell me that she was still looking for the love of her life and that she was wasting her time being with me. Which, by the way, was totally accurate. I had no intention to commit to her, as I discovered she was a woman who had way too many psychological issues as far as I’m concerned. My attraction to her was purely physical.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

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? Very

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

How wanted was this hookup for your partner at the time? Very

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.

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Very much

Why do you regret this hookup? The sex was awful and Marianne, the bubbly, blue-eyed blonde I used to worked with proved to be very psychologically challenged, due to an unhealthy relationship to her body and personal image issues.

What was the BEST thing about this hookup? When I was working with her, I always thought I could have an affair with her. I did it, it’s behind me now, I moved on to other things.

What was the WORST thing about this hookup? The sex / discovering Marianne’s psychological issues.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

All things considered, how POSITIVE was this experience? A little positive

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

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I am an unrepentant seducer; I’m never going to stop flirting with all the beautiful women who will cross my path as long as I’ll be able to get it hard.

What do you think about the Casual Sex Project? I like it a lot; although many stories seem made-up.

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