by Yaller

Gender: Male
Age: Looking at 70, just ahead
Race/ethnicity: Caucasian
Current location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Many
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? 2

At The Beach, Room 17

How long ago did this hookup happen? 2 months

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…)? Evolving

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? L. is about seven years younger than me, fit, active and independent; from a different ethnic and cultural background; but like me, relatively self-made and successful.  We met at an office party last year when her husband was a temp worker at my office, having lost his carrer job in the recession. The rumor had gone around that he had been flagrantly cheating on her and that she had caught him, stopped the affair and made him move to the basement. Her dress was zany, bohemian in a comfortable way and she seemed animated and happy. A few months after he left the firm, she came to another event, with a female coworker, M, my long-term lover, who had been her HS classmate. That connection was the way her husband found the temp job. I liked L’s spunk and the crinkles around her eyes. The new rumor was that her husband had left the country for several months.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At the second event we exchanged phone numbers and agreed to have lunch. She immediately said that she could get the whole afternoon off, as long as I could too. When I picked her up for the date, she immediately asked what I had in mind. But when I said a room and room service, she got coy and said that I was moving awfully fast and wasn’t ready on a first date. She wasn’t offended, seemed interested, but tentative. So, we had a nice, long lunch.  On the way to drop her off, she took my hand in hers while we drove, stroked it and eventually explained that she had decided that she wants a boyfriend and hoped we’d do more in the future.  She started texting me several times a day with flirtatious hints and asking when we could get together again. After one lunch, she asked to see my house and once there, we started making out. It was sweet and sensitive, but she objected softly when I took off her bra, “I’m not ready”, not now, we’re married”. But she was moaning. I put my hand in her pants and she was soft and wet, obviously ready. but she pulled my hand out and said. “I can’t”. I have a lot of doubt that women say ‘no’ while meaning ‘yes’ and I wouldn’t like that dynamic anyway. So I cooled it and took her back to her office.

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? Still, she kept in close touch. After texts, among other things, about being under the sheets together and warming each other against the cold, we agreed to spend an entire weekday together. I knew that she enjoyed nature, so I took her to a section of coastal bluffs which she’d not seen. We walked a few miles holding hands and talking. When we found a bench, she sat on my lap with my arms around her. I caressed her breasts and kissed her neck, which she enjoyed but did not reciprocate. We walked further, down to a secluded beach. She had told me that she no longer slept with her husband, that they’d grown apart. She had not been with many men and none other than him in forty years. There was a fisherman on the beach; we sat on a rock 1/2 mile from him, just above the surf and talked. Once he left, she again sat on my lap facing away. I kissed her, unhooked her bra, massaged her and played with her hard nipples. She moaned and I unzipped her pants, sliding my hand over her mons to the clitoris and labia. She was wet and she writhed against me. It took very little time for her to come and then she was limp in my arms for perhaps 20′. It was clear she was done, so we walked back to the car and drove to a small cafe for lunch. It faced the ocean, as did the faded motel next door. Even though we’d just had sex (No matter how Mr Clinton might define it), when I told her that we had a room there, she looked embarrassed, hesitant, and said ‘No’ quite firmly and repeatedly. Finally, I told her that I was going to take a nap, gave her the second key to room 17 and left. A few minutes later, she came in smiling, looking embarrassed, anticipatory and uncertain all at once. I was already under the sheets, ready to nap if need be, and I asked her to get undressed and join me. She said. “Look away”. When I peeked, she squealed, but she undressed and came to bed. Still, she acted unsure. She wanted to hug, to caress, to kiss, just a little. She came again with digital play several times and gave me a nice hand job, but Intercourse was still a line not to cross.

Did you have an orgasm? Did your partner(s)? She had several, including the one on the beach. I had one

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None

What were your REASONS for having this hookup? She is attractive, quirky and looking for someone/something new. I could tell that when I first met her and was delighted when she showed up at the second company event. .
I want to make love with women whom I admire and whose company I otherwise enjoy. It strengthens the bonds of understanding and shared vulnerability. It is delightful to be intimate with another person.
I would have approached her the same way even if her husband had been at the event. In fact he returned to the US, a new career and their home a few days later and has been in town throughout these meetings

Were alcohol or drugs involved? If so, how much? None

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 stayed in touch and had several more dates, some with sex, including intercourse, and some not. She has continued to flirt aggressively online but then retreat when together. She is ‘spiritual’ and I am not. She says that the relationship can not be only about sex. I am not used to being dominant, but it seems that this is what she responds to most. When she is receiving pleasure, oral, digital or through intercourse, she is beautifully expressive and vocal, but she needs to be coaxed into it each time.

To whom did you talk about the hookup? How did they react? I wanted to talk with M about it early on. But she noticed some flirtation that even I had missed and reacted with hostility, which surprised me. So I haven’t said anything yet. Eventually, I will talk with her. I have told her several times that I enjoy L and her flirting and that I especially enjoy some things that M finds to be faults. We laugh about it and have agreed to disagree and to not discuss L.
My wife has made it clear that we are not to discuss sex, even obliquely.
There are other people with whom I could discuss it, but they are not nearby to go out for the required beer.

Was this a consensual and/or wanted experience for you? For your partner? For me, this was wanted from the beginning, but its not exactly what I wanted. For her, it was certainly wanted too, though she seemed less aware of the inferences I was drawing, and may have thought she wanted something other than what we have arrived at. Its due to difference in experience, I think, but we’re both enjoyiing things as they come, rather than as we expected them to be.

Do you regret this hookup? If so, why? No. I continue to give a lot of thought to how we both are experiencing it and am careful to give her the time and space she needs

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? The best has been getting to explore sensuality with a woman who is returning to it after a long time and maybe experiencing her physical needs and potential for essentially the first time. The worst has experiencing her ‘two steps forward, one back’ behavior over and over, but that is easier to accept than it might have been 25 years ago.
I do not recall anyone with sexual behaviors like hers, unless I go back to HS, where good girls never went past 3rd base and usually not even there, no matter how hot the situation.
Because of our interactions, I’ve reflected a lot on the types of women who most appeal to me and questioned my motivations and honesty with them. My relationship with M seems much more mature, deeper and more satisfying than before. My relationship with my wife remains loving and stable.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? We came to this relationship from very different places and with very different expectations. That could cause lots of hurt and harm. But we recognized it quickly and have talked about the way differences in culture, indivudual needs, social expectations and even language can interfere with understanding. We’ve been as clear and considerate as we can be and its been a learning and growth encounter for us both. It could end next week or never, but I don’t think there’s any chance that it will end badly.

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!