My Older Coworker


What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
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? Very open and curious, fascinated by women of all types
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 0

My Older Coworker

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Complicated on-off situation with my then-girlfriend

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For 1 to 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? S was this beautiful, tall, redheaded mother of 4 that was hired in another department of the company I work for. My role in the company puts me in the position of interacting a lot with other departments, especially S’. On her first day at work, she showed up in a simple black dress, that highlighted her slender figure, nicely proportioned breasts and butt. I immediately found her attractive, but soon found out she was married and didn’t do anything about it. In the year or so that followed, we became pretty close, venting about our conflicts with our respective significant others.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Things were starting to get sour with my girlfriend at the time, and we broke up for a short while. One day during this period, I invited S over to my place after work, just to hang out and chit chat. We sat on the couch, sipping a beer and she got closer and closer to me, until she made herself comfortable with her head on my lap. I caressed her beautiful red hair. When the time came for her to leave, I kissed her on the lips. She was definitely caught by surprise, and I thought I just blew it. Instead, the next few days at work, she became even closer to me, coming to see me every time she had a chance. After a few days, she invited a group of colleagues over for dinner at her house (her husband was out of town for work), and things took off. She started playing footsie with me at the dinner table, and sat as close as possible all evening long. When everybody left, I used drinking as an excuse to be alone with her (all the kids were already sleeping by that time). We immediately started making out like teenagers, until she got up, walked towards the stairs and said, “Are you coming or not?”.

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? When we got to her bedroom, we closed the door behind us and undressed at the speed of light. The accumulated sexual tension was being released. I was impressed by how beautiful and soft her body still was, and proceeded to play with those boobs that I died to see for so long. I sucked on her nipples, and then kissed my way down to her pussy. She started moaning and begged me to be inside her. I place the tip of my hard cock on her soaking wet lips and slowly made my way. She felt incredible, warm and slippery. She came after only a few minutes, and her pleasure triggered mine. I released all inside her. We cuddled and chatted for a while after and then I left. We didn’t want the kids to find us.

How sexually satisfying was this hookup? Very

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 started sneaking some visits, but unfortunately her paranoid husband had her messaging tracked and caught us. It was not a pleasant experience, and we parted ways, never to see each other again. I don’t think we would have a future as a couple, but she was a very good friend and a good lover.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection

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? 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? To a good friend of mine, he gave all his support and approval.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finally having her, after a long time of fantasizing about her.

What was the WORST thing about this hookup? That her husband found out

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me fully realize that sex and love are two separate things.

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

All things considered, how NEGATIVE was this experience? A little 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? Casual sex should be less stigmatized and more accepted, it’s a normal, natural and good thing

What do you think about the Casual Sex Project? Love it!

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