January / September

by Chuck

What’s your gender? Man
How old are you? 60’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Silicon Valley, CA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retired
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)? 50+
How many hookup stories have you here posted before? none

January / September

How long ago did this hookup happen? 12

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 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? She was a co-worker and was a couple of years out of high school. She was hired to do shipping and customer relations. Our customers were all male, and I suspect she was hired for her looks, as she was the most beautiful woman I have ever met. She had solid natural Double D’s and long legs. Let’s call her D-Bra. At the same time she was down to earth, a real nice gal. She did not sleep around and had only 3 boyfriends by that time in her life. At work she was forever singing Christmas songs such as “Grandma Got Ran Over by a Reindeer”. Weekends, she was out partying at the clubs.
As it turned out, she lived within a mile of my apartment, so we ended up sharing a ride to work. That led to us becoming close friends, even though I was in my 50’s; that did not stop me from wanting to bed her. As close friends, she began to open up on her sex life. One day she asked if I would go with her as she was curious and wanted to go to an adult sex store.
The minute we entered the store manager came over and gave us a personal tour, answering many of her questions with: “you do not want to know,” and ended up giving her a small vibrator. Then I got smart and rented us a video as we went out the door.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At my place, I mixed us up some Piña Coladas and we proceeded to watch the tape. At the end of the tape, she asked where could she find a guy with a large cock who was willing to eat her out? I simply unzipped and asked if that was what she was looking for. She responded by taking off her clothes.

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? I must have gone down on her for a good half hour. She got into her first “69” and tried sucking me off, but I was more interested in having those long legs of hers wrapped around me. It was evident that she did not have much experience, but she was an eager learner. It was an all-nighter, and we went through several positions, some of which were her first.
When I asked her what would her daddy would think about her letting a man older than him fuck her, she went nuts and began squirting. Another first.

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? The sex was great and she came back several times for more. We both began to develop feelings, with her wanting to move in with me and maybe have kids, but I thought the age difference was too great. Looking down the road I could see a light at the end of the tunnel and it was a big train coming at me. She would be in her 30’s, still in her sexual prime, and my sex life would be fading. So I broke it off with her and she quit that job

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

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? My grandfather taught me years ago, if a woman is sharing her most private parts with you, you keep your mouth shut.

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Walking into a bar with her at my side, wearing a very short skirt, with her bazooka boobs, high heels, and every guy there turning to watch her walk by, and me knowing that I was going to be the one giving that body a pounding that night.

What was the WORST thing about this hookup? Our age difference.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

Anything else you want to add about this hookup? It was not the best sex I have ever had, but it was in the top 10.

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? The world is full of beautiful women and I sat out to kiss as many as I could.

What do you think about the Casual Sex Project? Interesting

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