With A Mature Co-Worker



What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Harrisburg
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Division Manager
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)? 22
How many hookup stories have you here posted before? 0

With A Mature Co-Worker

How long ago did this hookup happen? 20 years ago

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 less than 6 months

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? Terri is a short (4ft 8 in), petite natural curly red hair woman, light green eyes, fair skin, freckles, approx. 110lb, the body of a gymnast. She’s 20 years older but looked younger.

She became a single mom at age 16. Her parents helped her but she had to work for everything she had. A friend helped her get a job with this company 13 years ago and she quickly gained a good reputation as a dependable worker and had advanced as high as anyone could without having a college education.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I’d just started my first job out of college in an entry-level position. The salary was okay but the company was big and if I was willing to relocate in the future, ‘the sky’s the limit’ with advancement and promotions. The division I was assigned to respond to chemical spills. Terri was a relief supervisor logistics specialist in my section. I was warned by numerous people that she was not a nice person. I was assigned to work ‘day to day’ with her and she was actually very nice. I figured out quickly why she came across tough. If she asked someone to do something she expected it to be done. The department had a high turnover rate and HR generally hired people that didn’t care about their job. For the next couple of months, Terri and I became good friends.

Since I relocated to the area, I got a one-bedroom apartment 10 minutes from work. Terri lived an hour away.

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? It was a cold rainy October evening and we’d both been working outside all day but still had to return everything to the storage garage. Once we got the truck repacked for the next response it was dark and the storms were settling in. We were both tired, wet and had the next two days off. I recommended she stay at my place for the night and I’d take the couch. At first, she was hesitant but the National Weather Service issued a warning on the radio so she agreed but insisted on taking the couch. We picked up a pizza and went to my place. I told her to shower first and feel free to dig through my clothes for something to wear. She came out wearing a t-shirt that barely covered her cute butt. She wasn’t wearing a bra and her nipples were poking out. I showered quickly and we sat on the couch to watch the news. She cuddled up beside me and rested her head on my chest. I put my arm around her and we kissed. She pulled off my shorts and straddled me and we started having sex. She didn’t ride me long before I could tell she had her first orgasm. I pulled off her shirt and carried her to the bed. I thought she was a natural redhead. Now it was confirmed. We had sex multiple times that night.

I woke up to the smell of coffee brewing the next morning and Terri trying to find something to cook for breakfast. We decided to have sex then go out for breakfast. We talked over breakfast and both agreed we had a great time. Terri was worried about her job if anyone found out. I assured I would never ‘kiss and tell’ and suggested we make an attempt at a relationship but keep things between ourselves.

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? Terri and I dated secretly for years without anyone at work or her family knowing. I never met her parents because she knew they would not approve due to the age difference. I never met her son because we were close in age and she thought that would be awkward. I was adopted by older parents and they had passed away while I was in college so I had no one to hide our relationship from.

She began staying with me a couple of days through the week to cut down on driving. That lasted a few weeks then she stayed full time with me through the week and then most weekends. She got her tubes tied because, at the time, it was not common for women her age to have kids. I convinced her to take advantage of the company’s tuition program and she signed up for evening college classes. I helped her study. It didn’t seem long until she graduated with BS in business management. The company published her in the monthly newsletter as a success and offered her a division in Florida. I was offered a position at Gulf Shores at the same time. We accepted our new positions and went separate ways. We hooked up a few times when we had long weekends.

I started dating a local girl, got married and had kids soon after. Twice a year our company sends us to various locations for 3 days of training. Terri and I have dinner to catch up on things and then spend the rest of our time having sex.

Two years ago she got married to a guy close to her age. She plans to retire soon and admitted the marriage was for long term companionship because she was alone. Her parents were now gone and her son had died in the middle east.

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

What were your motives for this hookup? Attraction to partner(s)

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? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? This was the beginning of a great relationship.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? With the exception of having sex with Terri on occasion, I’m faithful in my marriage. Terri and I have a long secret relationship and I wanted it to continue.

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

All things considered, how NEGATIVE was this experience? Not at all 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’ve noticed in society today, it’s common to see a woman in their 40s are dating guys 20 years younger and it’s acceptable.

Terri and I are happy with the way things have worked out but the last time we were together, I asked Terri, “When we first met, what if we’d ignored the way society would have judged our age differences and had a public relationship? Would you have married me? I would have asked?” We both knew the answer and the sex after that conversation amazing!

In my lifetime, I’ve experienced how society changes its view on things.

What do you think about the Casual Sex Project? A good place to read REAL life stories.

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