by Mike

Gender: Male
Age: 62
Race/ethnicity: Caucasian
Current location: NYC
Highest education received: Some college (not currently in college)
Occupation: Artist
Relationship status: Married
Religious affiliation: Jewish
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Polyamorous
How many sexual partners have you had in your life (including oral sex)? 125(approx.)
How many hookup stories have you here posted before? 1

Long Distance Lover

How long ago did this hookup happen? 3 weeks

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends with Benefits

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’s a 65 year old woman, short,perhaps 5’2″, somewhat overweight but appealing with short red hair. We had met online when she wrote to me complimenting my work. I’m an artist and have work posted on several sites. We began exchanging emails which became somewhat flirtatious. Though she lives 3-4 hours away, I invited her to come visit my studio if she was ever in NYC and said she could pose nude for me. To my surprise, she quickly said she’d love to and arranged to travel to NYC. I already have written about our first encounter where we kissed and I brought her to orgasm manually, her nude, me clothed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We continued to email back and forth, both expressing the desire to get together again, take it further. We started to email several times daily, bantering back and forth provocatively. She arranged to come back to NYC and booked a hotel for the weekend. We arranged to spend Saturday afternoon in her hotel room and Sunday afternoon in my studio 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? I met her at her hotel and took her out to breakfast. we talked amiably and got better acquainted. Then we went back to the hotel. As soon as the door closed behind us, we both seemed swept up in a wave of desire and started kissing passionately. Again, as the first time, I quickly brought her to orgasm with my hand. Then, we stripped and she began stroking and sucking my cock and she quickly brought me to orgasm. I had expressed a desire to try Tantric massage and I had read up on it. I brought some massage oil which I warmed in the microwave. I proceeded to give her a long slow full body and yoni massage and eventually brought her to a very deep orgasm which she said was the best and most intense of her life. I lay down beside her and she stroked my cock till I was hard again and just stroked and sucked me for a long while, which was quite heavenly. I didn’t come again though. We ended up falling asleep for a while and then I had to leave. The following day, I picked her up in my car and drove to my studio. We went out for breakfast again and then back to my studio where the intention was to do some work, with her posing for me. I had told her it was a fantasy to do artwork with both me and a model being nude and she agreed it sounded exciting. Once we were in my studio and naked, I didn’t feel much like working and again we were both swept up in a rush of desire. I brought her to orgasm right away with my hand. Then, I laid her down on a posing bench and fucked her till we both orgasmed. I was hard right away again and we switched places, I lay down on the bench and she stroked my cock for a long time which I really enjoy, sort of surfing on a wave of intense pleasure. It was snowing all day and I was afraid she wouldn’t get to her train or me home, so we ended earlier than expected.

Did you have an orgasm? Did your partner(s)? We both did. me 1 and her about 3-4

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None though we have discussed health issues before and we had both recently had a full battery of tests

What were your REASONS for having this hookup? Both of us were looking for a regular FWB arrangement

Were alcohol or drugs involved? If so, how much? Both days, I had a few hits of marijuana which I find relaxing and sexually arousing.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We have continued to email back and forth and the expectation is that it will continue. There are issues, though, in that it’s long distance and she’s on a limited budget. I’m still working but have limited time.

To whom did you talk about the hookup? How did they react? Only my wife. she finds my hookups fascinating and amusing and is interested in all the details.

Was this a consensual and/or wanted experience for you? For your partner? Yes, of course

Do you regret this hookup? If so, why? No, not at all

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? We had great sexual chemistry, the orgasms were intense for us both. We both feel like we want to experience al the pleasure we can, while we can. Many people our age are no longer sexual at all, bu we both feel as sexual as ever.

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 or anything else? My wife and I decided to be polyamorous about 5 years ago and have both had lovers. It has been challenging to find partners, even in NYC, who are open to having an affair with a married man, but I’ve had casual sex with perhaps a dozen women over this period, each time hoping to find someone for an exclusive long term affair. That has been difficult for many reasons, whether because the women are cheating on their husbands, they have health issues, emotional issues, or other practical issues. Still, it has been fun and rewarding.

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