My First Older Man



What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: High school diploma
What’s your occupation? Cashier and student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 15
How many hookup stories have you here posted before? none

My First Older Man

How long ago did this hookup happen? like 3 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? FWB

How long did you know the person before this hookup? For less than a week

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 a clean-cut dapper man. He had a cigar in his mouth. I was working at a fast food restaurant on the night shift when he approached the walk-up window to order food for his daughter. From the moment I laid eyes on him, it was like love at first sight. We started talking about going to dinner after, and he kept complimenting me. Long story short, I told him I would take him out to dinner (trying to impress him lol) even though he offered to pay. He then gave me one (of many) of his business cards for his limousine business. Before we hooked up, I just felt an immediate attraction, like he was what I’ve been missing my whole life.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Two nights later, we went out for dinner at Chili’s (his favorite spot). We went on his family yacht and chilled there for a while. Then we went downtown for a drink and back to his place after. I fell asleep on his couch because I was tired and had to work that night. He dropped me off at home to change my clothes and dropped me off at work. He said he would pick me up after, which he did, and then asked me to stay the night with him. I said no the first time, but a week later he asked me again and I said why the hell not. We started talking about past relationship and other random stuff. He then started talking about how he could take care of me in every way possible. He kissed me, and said, “trust me”. At this point, we both instigated it because he took the first step and I didn’t reject it. I wanted it as much as he did.

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? After he told me to trust him, he kissed me and went down on me, licking my clit so fucking softly. I almost came within the first 15 seconds. I had never felt anything like that before. He was so patient and caring with his touches and kisses. He really made love to me. I sucked his dick and the way he talked to me and held my face when I went down on him made my pussy flood. He then turned me around and we did it doggy style. I then got on top of him and rode his cock. It ended with him on top of me and both of us drenched in sweat.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? After we did it, we showered and talked. I told him I’ve never been treated like that before. The next day, I really didn’t know how to feel because even though I’ve always been into older men I’ve never actually had sex with one (he was 45 at the time but didn’t look like it). I really didn’t have any expectations for the future. I’m the type of person that goes with the flow. We are still good friends now.

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

What were your motives for this hookup? Fun, pleasure, horniness, 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? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’ but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

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? My best friend, who already knew that I was attracted to older men. She was surprised when I told her how good the sex was.

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

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? The financial stability mainly. He was a retired longshoreman. They make serious bank and all the girls in the city want them. We actually were in a real relationship for a while. We started living together and he bought me my very first car, an SUV Jeep. Our personalities matched, we both were goofy as hell and we’d always show out when we were in public. Everyone loved to be around us.

What was the WORST thing about this hookup? At first, I would get a bit lonely because he was always so busy with his four businesses. I then realized he had me kind of helping him with his everyday work, so I became somewhat his assistant. It’s funny because I used to tell him all the time that he seriously needed one.

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

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

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

Anything else you want to add about this hookup? no

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 don’t see an issue with casual sex. It’s your life, you live once, so why not do what you want to do. Fuck what anyone else has to say. If they have a problem with it they could stick it up their asses because no one cares and they might not be happy with their self and no one probably wants them. That’s why they’re mad!!!

What do you think about the Casual Sex Project? It’s good!

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