Doing the Friend’s Boss



What’s your gender? Man
How old are you? 58
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? Houston
Highest education received: Some college (not currently in college)
What’s your occupation? Sales
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? a little kink/fetish
How many sexual partners have you had in your life (including oral sex)? over 50
How many hookup stories have you here posted before? 8

Doing the Friend’s Boss

How long ago did this hookup happen? 1990

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

How would you best classify this hookup? One-night stand

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? Kathleen was a good looking redhead, with perfect tits, a great ass, and lips that were perfect for sucking. She was an office manager for a legal firm I had some association with at the time, since I was fucking one of her staff. Apparently. her staffer told her about our trysts, and was somewhat curious about me. I ran into Kathleen and some of her staff at a nightclub after doing some late work.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The staffer I had been fucking at the time invited me over to their table, where she made some space for me between her and Kathleen. After a few drinks and a couple of dances, Kathleen and I started cozying up a bit. I started running my free hand up and down her legs under the table, and it seemed to get her excited. She asked me if I’d like some coffee, and follow her home for some. Sure! I wasn’t going to pass up the chance!

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 we got to her house, I had forgotten to ask about her significant other. He was out of town for a few days, she said. Then off to the kitchen for some coffee. I’m watching her make coffee, her back to me, and I get off my chair, moving slowly to her and lean up behind her. I started feeling her up gently, going for her tits and she melted. She slid her hands to my crotch to feel a growing erection that made her gasp. From there it was off to her bedroom, where I stripped her and gazed at her incredible body. I took my clothes off and we jumped into bed, going right into a quick 69, Her pussy was tasty and wet, and she sucked cock like a champ. I flipped her over, and got on top, sliding my cock into her, and she let out a loud moan. We fucked like this for a long time, then she got on top, pumping hard trying to make me cum. We ended up with me fucking Kathleen doggystyle. What a beautiful ass to see as my cock slid in and out of her. I came on her ass and we were both exhausted. She played with my cock and balls, eventually going down on me for a long blowjob, and I came again. I left very early the next morning.

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 didn’t really stay in touch, but we did run into each other from time to time, and got the same result. It was just two people who wanted to fuck each other occasionally. Still enjoyed her company.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? 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? no one

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? I got to fuck a hot lady I didn’t know wanted to fuck me.

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? not really. I still pursue the occasional casual romp.

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? Wished that there was more regularity to it.

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? No thoughts at all.

What do you think about the Casual Sex Project? Fun place to talk about your experiences.

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