Love Those Older Ladies



What’s your gender? Man
How old are you? 59
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? USA
Highest education received: Some college (not currently in college)
What’s your occupation? sales
What’s your current relationship status? In a serious relationship (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
How many sexual partners have you had in your life (including oral sex)? over 50
How many hookup stories have you here posted before? 9

Love those older ladies

How long ago did this hookup happen? 7 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

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? Kathy was a slightly older (59 to my 52 at the time) woman I had contacted via a dating site. She was very attractive, and I couldn’t understand how she couldn’t get a date. We hit it off after a few days of messaging each other. Eventually we did set up a dinner date, which was very enjoyable. She suggested I pick her up at her home, which I did being the gentleman I am. When I saw Kathy in person for the first time, the dating site photos didn’t do her justice. And she looked incredible. I for one, love women with beautiful legs, and Kathy was showing hers off in a short skirt and heels. And off we went to dinner … and then some.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We found ourselves having a great time at a little Italian place, which provided us with a table for two in a nice corner of the restaurant. We chatted and flirted quite a bit, and then Kathy started rubbing one of her legs against mine. I pretended not to notice, but it was pretty obvious it was affecting me. I slid my hand down under the table, and lightly grabbed her ankle, sliding my hand up and down what I could of her leg. All of a sudden Kathy got up and went to the bathroom. About 10 minutes later she came back, said we should leave. Okay, why? She leans into my ear, and tells me she was soaking wet while I rubbed her leg, and had to get rid of her panties.

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 don’t think I’ve ever driven as fast to take someone home for a good reason. While I’m driving, she’s rubbing my leg just barely getting to my crotch, and my stiffening cock. We get to Kathy’s house, and once inside we can’t keep our hands off each other. I’m wondering how long it’s been for this lady to have gotten laid, but I was glad it was me about to. We’re kissing heavily on her sofa, and touching each other. She’s got my cock and my hand is climbing up her skirt. We get rid of our clothes, and I’m sucking on her tits, while she jerks me off. She wants cock bad, but I have a request for her. Anything, Kathy says. Would she mind if I nibbled on her legs. She obliged, and I asked her to keep her heels on. She didn’t have a problem with that, but it’s just a thing for me. Don’t ask it just is. I nibbled on her fabulous legs, and made my way up to her wet pussy, and ate that. She gasps heavily while I do. I finish, then she starts sucking my cock. It had been a while for her. I ask her to slow down, we have all night. And we do. She sucks me off til I almost cum, then I lay her down and stick my cock in her. I positioned her legs over my shoulders, heels still on. It was awesome. I fucked Kathy for a long time that way before we changed positions, eventually cumming on her tits. Kathy came quite a few times along the way. It was the start of a nice fuck buddy relationship.

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 kept in touch, went out a few more times and had more hot sex before we went our separate ways.

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

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? 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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I enjoyed an older and willing woman who obliged my silly whims, and enjoyed them too.

What was the WORST thing about this hookup? it ended

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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? not really

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 enjoy casual sex when its available, and my partner is willing for some

What do you think about the Casual Sex Project? good site

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