Older Coworker



What’s your gender? Woman
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Eugene, OR
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Sales Team Member
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 35ish
How many hookup stories have you here posted before? One

Older Coworker

How long ago did this hookup happen? Six Months

What was your relationship status at the time? Single

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? He was an older coworker, tall and fit with greying hair and a goatee. I will call him Justin to make things easier. I had worked with him for about eight years and he had been married for most of it but was dealing with his divorce when we hooked up. Honestly before this he was not even really on my radar as a potential partner and I had always thought it best that coworkers were off limits for dating and sex.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Justin and I were at a conference. Most of the sales team I work with goes to this conference every year and it’s a good opportunity to make contacts and sales. It’s also away from home and notorious for hookups between coworkers. One friend from work got herself knocked up at this conference a few years back.
It was the second day of the conference and we had been meeting with clients all day. I have always used my looks and flirted with them a bit to increase sales and Justin had been watching me all day. After work he and I went for drinks at the hotel bar. We were talking and I could tell he was struggling a bit.
I consider myself pretty open sexually and when it comes to my partners. However there was a slight hesitation with what I was thinking, for one he was a coworker and two there was the age difference. I slept with a professor in college but he was only about five years older than me and Justin was more that 15 years older.
I flirted with him a little bit and made the decision to sleep with him to make him feel better. I have to admit also to being a touch horny and I figured Justin would be a safe bet to take out my sexual urges on. I finally asked him back to my room and he said yes.

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? Justin and I had been drinking and we were buzzed enough that inhibitions were gone but we still knew what we were doing. We ended up in his room instead of mine and made out on a couch for a bit. He took my clothes off and spend a lot of time feeling me and playing with my boobs and grabbing my ass. He sucked on my breasts for a while until I asked if he wanted me to suck on him. I put his cock in my mouth and he was quite large and blew him until he finished.
I got up and rinsed my mouth out and used the bathroom and climbed back into his bed. We talked a bit, and I learned the only other woman he had ever been with was his ex-wife and it had been many years since he had experienced oral. He complimented my body quite a bit and was a big fan of my breasts and my tattoos.
About an hour later I was feeling horny again. I have always been take charge in the bedroom and wanting what I came for I decided to mount him. I am not sure how long I bounced up and down on him but I remember thinking how hairy he was and my skin was red afterwards from when I would lean forward to kiss him. We both got really sweaty and loud . I wasn’t expecting an orgasm but I had one and so did he and I climbed off of him. I had fucked him. I fell asleep for a little but snuck back to my room early in the morning.

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? I was actually a little sore the next day and my boobs hurt. I felt great the next day and we were both able to focus on work. Justin and I hooked up both of the two following nights at the conference and continued on for several months afterwards. We went to dinner and the movies and fucked often and basically were dating. I knew he was rebounding so i never let it get too serious with him and broke things off with him when i started sleeping with my current boyfriend. For him it had been a touch more serious than that and i think he may have been in love with me. Things got very akward he had a hard time accepting it was over and i ultimatly changed sales teams. To me he is now a part of my sexual history and past and we all have one.

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

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, Boredom, To make my parter feel better

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? Somewhat

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? Told a few friends who wern’t sure sleeping wiht him was the right idea. They were right

How would you best summarize people’s reactions about this hookup? Relatively negative

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? Very

Do you regret this hookup? Very much

Why do you regret this hookup? Becasue of the effect it had at work and I was forced to make changes there. I was able to keep it quiet as to why otherwise it could have damaged both of our reputations and carreers

What was the BEST thing about this hookup? The sex was good and he treated me very well

What was the WORST thing about this hookup? The aftermath at work

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Didn’t really change anything about how I feel about casual sex or sexuality but it has confirmed my belief that workplace romance is not the best idea.

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

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

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