A Very Mature Hookup


What’s your gender? Man
How old are you? 63
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC, NY
Highest education received: Some college (not currently in college)
What’s your occupation? Artist
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Jewish
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Polyamorous
How many sexual partners have you had in your life (including oral sex)? 125+
How many hookup stories have you here posted before? 1

A Very Mature Hookup

How long ago did this hookup happen? Last night

What was your relationship status at the time? Same as current status

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

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? She approached me on OKCupid with a one word question, “Perhaps?”. When I looked at her profile, she said she was 70, a good bit older than me but her pictures looked good and she seemed educated, interesting. We exchanged few emails and arranged to meet for a drink at a bar. At the appointed time, the bar was too crowded and noisy to talk so we moved to a hotel bar where she obviously was a regular. In person, she looked better than her photos, slim, fit, stylishly dresses, with a cute pixie haircut.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We talked for a few hours over drinks about ourselves. She was widowed, had been married to a creative person like myself and was fascinated by my open marriage, how it worked, etc. She had never experienced anything like it and was curious. Since being widowed, she had decided to enjoy herself, seek pleasure, etc. We ended the evening agreeing we’d like to get together again.

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 originally agreed she would come to my studio as she wasn’t comfortable bringing a stranger to her home but then later she wrote and said she had decided to have me to her apartment. I was relieved as my studio was a mess. Soon after our first meeting, I came down with a bad cold and was afraid I would have to cancel. On the night in question, I was feeling better, though not 100%. When I arrived, I told her I didn’t want to kiss for fear of infecting her, though I do love kissing, making out. She agreed that was wise. After some chat, we undressed and got into bed. I was quite amazed at how beautiful her body was and more so since she confided she was actually 73. She had a better body that most 20 or 30 year olds, with a small waist, firm C cup breasts and nice hips and bubble butt, with a shaved pussy. We proceeded to stroke one another for quite some time. I went down on her and licked and fingered her lovely pussy and she quickly came rather noisily. I was surprised at how quickly she came. I wasn’t feeling quite well yet and she had to stroke and suck me for a bit before I got hard but then she was anxious to feel me inside her so we fucked in missionary for a while and then took a break for more stroking and sucking. I wanted to lick her pussy some more and at first she said she never comes twice. I insisted on trying and she again came rather noisily. I got on top again and came inside her. We continued to lie in bed and chat for a while until we decided to go to her favorite local bistro for dinner. We agreed to meet up again.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 chatted over dinner and we have lots in common, like each other and enjoyed the sex. We agreed to make it a regular thing, which I hope to do. I have several women who I have been having sex with sort of regularly, but each one has some issues. A few live far away and can meet infrequently, some have health issues affecting the quality of the sex, some have emotional issues. This woman seemed like a great fit for me as a regular sex partner and friend.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed history, had both been recently screened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Making new friends

How intoxicated were you? Not at all (no alcohol or drugs)

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? Just my wife, briefly, when I arrived home.

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? Great sex with a beautiful new partner

What was the WORST thing about this hookup? I wasn’t feeling 100%, still a bit sick with a cold/flu

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all, it only reinforces my positive feelings about casual sex

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? My wife and I have had an open relationship now for about 6 years. Nobody really prepares you for the realities of aging and sex/pleasure and a lot of the cliches are that older people no longer want or enjoy sex. it my be true for some but the women I’ve ben having sex with in the past few years are among the hottest, most orgasmic and insatiable women I’ve ever had. They may show signs of wear, but they are incredibly sexy and the sex has been among the best ever. Also, when they are so avid, I find I can have several orgasms in a single session

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 feel pleasure and touch are very important for health and well being. I couldn’t live without it. I love and am committed to my wife but we don’t really mesh sexually or enjoy the same things. We enthusiastically support each other in finding other partners to satisfy us. Friends are mostly shocked, incredulous, horrified and at the same time fascinated and jealous. Most are too insecure to allow themselves and their partners such freedom. Most couples we know no longer have sex, miss being touched and yet do nothing about it. Some cheat

What do you think about the Casual Sex Project? I think it’s great. Any dialog about the reality of people’s sex lives is a good thing. I enjoy reading other people’s experiences and it feeds my fantasies, gives me ideas for things to try. Truth is always good

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

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