Crush on a Co-Worker



What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? USA, NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Financial Analysts
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
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 0

Crush on a Co-Worker

How long ago did this hookup happen? last week

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? She is Hispanic, from Ecuador, and her name is Kim (fake name). She is in her early 30s, about 5’4- probably 120 lbs with about B breasts. We worked together for about three years, although she was in a different group- but we worked for the same senior manager. Before the hookup- it’s always been just professional at work- we are coffee buddies and sometimes lunch buddies. But starting in September, she transitioned into my group and moved next to me- I was training her for two weeks and began to notice her a bit more. So she would come to me naturally for a lot of things work related- and we text each other (nothing sexual) sometimes during weekends, but it could be about work or just like friends.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?

Last Christmas party- we were both drinking quite a bit at work- but nothing happened. Then we hugged casually- that’s when I noticed how great she smells and she pressed her chests against me- it feels great. That’s when I knew I had a crush on her and began thinking a lot more about her. Then we both got sent on a business trip to Minneapolis.

The second night the manager in Minneapolis office decide to have dinner/drinks with a few of us. There was a total of 6 people, Kim, and this other girl Mona were the only females. We had a few drinks and one of other group’s manager Tom keep pouring drinks and Kim got the sense that maybe she had a little too much, so she asked me to not lose sight of her for the rest of the night. And throughout the night whenever Tom got a little too close to her, I would use my phone to send her a text message so she could use it as an excuse to walk away and respond. She finally decided she didn’t want to be around him anymore and we ended the night around 7:30 pm since we had an early meeting the following morning. I had about four double whiskeys on rocks, and she must have 4-5 glasses of wine and a couple of shots of tequila as well. Kim was tipsy, and we linked arms headed to the hotel. We were staying on different floors, and when the elevator arrived on hers she walked out while still linking my arm, so I naturally just dropped her at the door. I said goodnight and to call me if she needed anything. We embraced for a good 20 seconds, and she gave me a friendly kiss on the cheek. I would be surprised if she didn’t feel that I was shocked and hard.

Kim then texted to see what I was doing. I told her I was laying down and watching basketball and she said that she wanted to binge watch some Games of Thrones and asked if I was interested. I was in the middle of pleasuring myself when that happened- so I responded: “Yes, I have some drinks too if you want to drink.” She said she didn’t want anything crazy hard like whiskey- so I went to Target 2 blocks away to grab some Mike’s hard lemonade for her and bought a small box of condoms- just in case.

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 I got to her room, she was wearing a sports bra and shorts. She was sitting on the hotel bed, so I pulled up in the chair next to her and opened a lemonade for her. Then a few minutes past and she noticed I was clearly watching her cleavage from the sports bra. She then asked me to sit on her bed to get more comfortable.

Another 10 minutes passed after I finished my drink and she had almost finished hers, that’s when some fairly hardcore sex scenes came on in Game of Thrones, she started to move a little bit, and I had a hard-on too. It’s now or never. While she was switching positions, she accidentally felt the hard-on. She was surprised and said, “you like watching Game of Thrones for the nudity?” I was a bit embarrassed at that point, so I just said “no, not at all,” she laughed and said ‘it’s ok, guys do it,” then I just told her “it’s not games of thrones, it’s you.” That’s when I think I shocked her a bit and her face was blushing and the amount of alcohol she had probably made her a little more daring than normal. She played it off like, “that’s sweet.” I touched her face and said ‘you’re blushing and your perfume, it’s driving me wild’. That’s when I think it must have turned on a switch for her, we locked eyes and just glazed at each other for about 5 seconds, and my hand was still touching her face, I can feel it’s even hotter than before, that’s when she touched my face as well. I pulled her face towards mine and pressed my lips on hers, she did not hesitate, and we ended up kissing passionately and slowly for about a minute. I slowly kissed her neck while her hands embraced me and slid under my shirt from behind. I brushed the outline of her breasts through her sports bra; her nipples were erect at this point. She jokingly asked if the bra was in the way, I said it wasn’t and pinched one of her nipples while licking the other one through the bra. I think this drove her insane with anticipation because she quickly took off her bra. I began to fondle her breasts while pinching her nipple on occasion- at this point- my shirt is off, and the blanket that was covering her is no longer on. With one hand still playing with her breast, I slowly slid my finger in her panties and touched her outside lips. She decided to pull my pants down and felt the condoms in the pocket and just grinned at me. She was going to give me a blow job, but I told her that I wanted to taste her also, so I laid on my back, and we got into a 69 position. It wasn’t the best blow-job I ever had which was probably because she was drunk, but her pussy tasted so good. I was about to cum, but suddenly she started trembling and started moaning into a massive orgasm. I laid her down and fingered her slowly before putting my penis on her pussy and teasing her a bit. She recovered from her orgasm and moaned, “fuck me.” I began to fuck her without a condom until I pulled out and came on her body.

She then went to the bathroom to clean up and said: “I needed this, its been such a stressful trip.” Later, she started stroking me, and I began to get hard again and said that this time I wanted to put the condom on and come inside her. So we kissed again passionately, and this time I focused more on her tits before I went down on her again, this time fingering her intensely. She came, and I put on a condom before fucking her, I asked if I can finish while she’s on top so I can play with her tits. She started riding me and couple of minutes later I came inside of her while she was licking my nipples.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 both feel pretty guilty. I’ve been training her and covering for her professionally so she probably enjoys the attention she gets from me but we understand this cannot go on further. Now we’re back in office it’s getting awkward.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? A little bit

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one.I still jerk off to thinking about the first night we hooked up.

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? A little bit

Do you regret this hookup? Somewhat

Why do you regret this hookup? Just because it’s the classic workplace hookup. I don’t know if I want to get anything out of this

What was the BEST thing about this hookup? The sex, her body, her smell, and her willingness to let me do whatever I wanted.

What was the WORST thing about this hookup? We still have to work together.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not much

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

All things considered, how NEGATIVE was this experience? A little negative

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