My First Coworker Hookup



What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Iowa
Highest education received: High school diploma
What’s your occupation? Maintenance management
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? +/-15 and counting
How many hookup stories have you here posted before? 3

My First Coworker Hookup

How long ago did this hookup happen? 5 years ago

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

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? I had known her for a couple of years but in the year leading up to this, we had begun confiding in one another regarding our marital infidelity and emotional and sexual needs. She was “girl next door” cute. One of her complaints had been how her husband couldn’t last long enough to make her orgasm. I had offered to have sex with her to give her a release a few times. I very much liked her and felt that she deserved some proper sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I ended up running into out on town right after work one day and asked her what she was up to. She said her husband was working that evening and asked if I wanted to come to her house and hang out. I followed her home. We went in and sat around and talked for a bit. She had told me before about her husband’s porn. I asked if she wanted to watch some of it with me. It was pretty lame stuff so we watched for a while then went out on the back porch to sit and enjoy the evening. She told me that she could start to smell herself. I looked at her and asked if I could kiss her.

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? She kind of leaned toward me and I leaned in and began kissing her. Then, I started pulling her closer. She asked if we could go inside so the neighbors wouldn’t see. We initially went to the living room and sat on the couch to continue making out.

I asked her if I could go down on her. She shimmied out of her pants and underwear and I gently began kissing her inner thighs and mound. I then began to penetrate her as she watched and moaned. She took the remainder of her clothing off and pulled me up to remove mine. She went down on me for a little bit and then took me to her spare bedroom. We enjoyed some foreplay, including some 69. Then, she retrieved a condom and tried to place it on me. It was clear that she didn’t know what she was doing so, I showed her how to put a condom on me. I was a little harder than most guys as I’m a little larger sized and it was a regular condom.

Once I had it on, I laid her back and gently entered her. She felt amazing. We kissed and ground and slowly made love for a while.

We changed positions several times over the course of the evening. She was willing to follow my lead. She had her first orgasm with me on top of her.

I gave her some recovery time while I continued to rock on her. We enjoyed a little small talk until she heated up enough to get into it again.

The second time around, we enjoyed a little harder and deeper sex. I was still trying to be gentle with her, knowing that she was not used to long sessions. She was willing to keep going despite the fact that she was wearing down. She had a second orgasm, stronger this time.

Once again, I slowly continued rocking inside her, trying to help her heat back up. I had been holding off on cumming, desiring to give her as much as she wanted or could take.

For the next round, I just wanted her to ride me so that I could play with her breasts, and look at and feel her body. She didn’t see herself as beautiful but, she was. Finally, she had one more orgasm.

I asked her if she could cum another time for me but she said that she wanted me to cum now. I started pulling her around a little more forcefully and finally throbbed inside her, releasing all my stored up energy. It was an awesome orgasm and the condom was full of my cum.

I told her how much I really would have liked to have cum in her mouth but, I’m not sure she was ready for that anyway. After I was done, she got off me, went to the kitchen and checked her phone then called her husband (missed call). I really wanted to cuddle with her but she told me that I needed to go home. It was kind of abrupt and very non romantic.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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 had agreed at the time not to let it affect our friendship. I still very much appreciated her as a friend. We got together again a few days later. That time, I think I accidentally hurt her. I was going deep inside her and she ended up bleeding. I was thinking maybe she had begun her period but she told me a few days later that she had not. After that time, she took off several days from work and I couldn’t get in touch with her. Our relationship totally changed. She didn’t want to talk about our other sexual exploits anymore. She would get upset if I told her about hooking up with any other women (including/especially ones she already knew about). I began to have speculations that she had developed some sort of additional feelings beyond friendship but, she was so weird about it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Didn’t want to disappoint my partner

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? 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? No one.

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? A little bit

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

Do you regret this hookup? A little bit

Why do you regret this hookup? The sex was phenomenal. She didn’t have the breadth of experience I had (she had mostly been with selfish jackhammers before) despite having many more partners than I had. The emotional issues that developed later were bad, however. I wouldn’t trade the great sex for the friend I lost.

What was the BEST thing about this hookup? The sex was fantastic. Making her cum so many times was awesome. I loved seeing her enjoy herself.

What was the WORST thing about this hookup? Losing my friend. Also, she would occasionally text me months and years later with kind of strange messages, like telling me she finally got fucked in the ass and that she loved it. I’m pretty sure she was trying to make me jealous or at least hurt me a little.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? If we could have continued just having an occasional detached hookup, it would have been great. I see it’s just not possible, however.

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

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

Anything else you want to add about this hookup? No.

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? This has reaffirmed for me that good casual sex is really a myth. One of the two (sometimes it’s me) will develop more of an emotional bond than the other.

What do you think about the Casual Sex Project? It’s nice to have a place to discuss this stuff.

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