Sex With My New Employee



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? PA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Single
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)? 4
How many hookup stories have you here posted before? 0

Sex With My New Employee

How long ago did this hookup happen? 1 month 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 a month

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? Megan is a first year college student, age 19, works part-time for me, cat shaped blue eyes, brown hair, smooth skin, and thin. Her parents migrated to the US from Ukraine in the 90s. Her goal is to get accepted into law school.

I’m a self employed lawyer/widower with no kids. My office is a converted house in a small town’s historic district. My work is mostly contracts and land deeds, nothing high profile. I have a full-time paralegal on staff but I needed someone to help with scheduling, typing and answering the phone when I’m away from the office. I know a professor at the local university, and he recommended Megan. I interviewed and hired her on the spot. I’m glad I did. She’s very organized, ambitious, and willing to learn anything about the legal world.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? During Megan’s summer break, my paralegal scheduled a two-week cruise. Megan offered to work extra hours and tagged along to court just to see how the system works.

Thursday afternoon around 5:00pm, I was getting ready to leave. I heard Megan on the phone trying to be quiet but arguing with her boyfriend. I heard her scream, “FINE,” and she got off the phone. I grabbed my jacket and asked if everything was okay. She started to vent but stopped. I told her it was fine. She was having a fight with her boyfriend and was thinking of calling it quits with him. They had plans, but he decided to binge game with his friends. He doesn’t work, is not in college, and lives with his parents with no plans on the future. She acted frustrated and made the comment, “I’ve never had luck finding a good guy.”

For helping me out, I offered to take her to dinner since she had no plans. I’m a member at a local country club with a standing reservation for dinner. I asked if she’d like to join me. I was a little shocked when she said, “I’d would love to but is what I’m wearing OK?” We had been to court so she was wearing a long black skirt, long sleeve white button up shirt and heels. I told her the restaurant would consider that acceptable dinner attire.

We arrived and my table was ready. With no issue, they brought out an extra set of dishes and flatware for my unannounced guest. Dinner was great. Megan is a wonderful person. I know she was looking at the prices as she tried to order. I reminded her that she was my guest and I’m picking up the tab. I insisted that she try something she’s never had before. She became more relaxed and dinner was fun for both of us. She has a great personality and asked questions about law. On the drive back to my office to get her car, she thanked me for a wonderful time. I promised we would do it again. We arrived at my office and she told me she needed to go inside to get ‘something’.

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? We got inside and she pulled me into the conference room gave me a passionate kiss and unbuckled my pants. She wrapped her hand around my penis, then got on her knees and sucked it. I was hard within seconds and about to explode. She wiggled out of her skirt and panties and sat on the edge of the table. Her legs were open and I guided my penis to her smooth entrance and dove inside. She felt so soft and wet and moaned in pleasure as we had sex. It had been a long time for me and I was trying to make the moment last so I slowed down. She pushed me into a chair and got on top. She gave me a passionate kiss with tongue and we climaxed at the same time. She didn’t appear to care that I finished inside her.

I asked if she wanted to do this again tomorrow night. She agreed. I invited her to my place after dinner. She told me she would pack a bag if I didn’t mind. I smiled and we kissed. She got in her car and left.

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? A month has passed. She’s broke up with her boyfriend via text. She said he acted like he didn’t care. His only reply was, “OK.”

On days Megan works for me, we have dinner together and sex at my place. I don’t know where this is going but we’ve both decided to continue and see where it goes.

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

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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

To whom did you talk about the hookup? How did they react? My paralegal. She’s been with me for 15 years and a close friend I can lean on. She’s also good at reading people. She thinks I should continue and believes Megan is a wonderful person.

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

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? Connecting with a wonderful person & having an emotional uplifting experience. Both of agree it wasn’t just sex. We feel something connecting us.

What was the WORST thing about this hookup? The age difference between us. I hope society doesn’t pressure this relationship to break away.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I had been with my wife for over 20 years before she passed. I never thought I would find anyone again. This relationship looks promising. If it doesn’t, I’ll be more open to ‘getting back in the game’ and taking risks in the future.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? No matter what’s happened in your life or how old you are, take a chance at finding that special person again. I believe everyone has a special person out there but society puts boundaries on whom that person is.

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? Society is a harsh judge. If two people are connected, age should not matter. Megan and I have a connection and other things in common. She introduced me to her parents and they don’t mind us dating.

Megan is a sweet person but also knows what she wants in life. What little time I’ve know her, she goes after what she wants 100%.

Megan came from a large family and her parents taught her to become independent when she became an adult. They told me she’d made numerous attempts at dating guys her age but they had no ambition and were too immature for her. I get along with her family and Megan is excited for that.

What do you think about the Casual Sex Project? I discovered this link by looking at a men’s health article. It’s a good idea and great place for people to share stories.

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