by OldYaller

Gender: Male
Age: 68
Race/ethnicity: Caucasian
Current location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: self employed
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)? over 100
How many hookup stories have you here posted before? 3

Doing Business at the End of a Long Day

How long ago did this hookup happen? 4 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…)? ongoing

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? M and have worked together for more than 25 years. She is 8 years younger than I, slim, limber, athletic. We are the leaders of our company’s two divisions. We have been sleeping together off and on for about five years.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the travel day for our company’s annual retreat at a resort, a four hour drive away. M’s husband was coming and I had no expectations of having sex with her. We usually don’t on these retreats because the risk of getting caught is too high.
I’d unexpectedly and briefly made love with her friend L, right before L had to go to work and I had to leave the city for my drive that morning. After that, I was feeling pretty horny, so I’d stopped in a brothel on the way to the resort.
I arrived for the retreat feeling relaxed; ready for a business-like set of meetings and light socializing.
As planned, I met M in the hotel lobby with her husband, D, for dinner.
After the usual friendly greetings, D surprised us by saying that he wanted to watch a basketball game in their room, and he suggested that M and I eat and then use my room to do the prep work for the weekend’s events, while he watched the game.

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? Needless to say, we agreed  and sent D back to his room while we headed towards the dining room. But without a word, M and I detoured straight to my room, where we quickly undressed and got into bed. We’ve slept together many times and in many different situations by now, but we always start with a long session of kissing, hugging, stroking each other all over. M has an unusual response to intimate, touching and sex: she gets muscular spasms in her back and trunk that come in pulses, like an orgasm, but they are just excitement and build-up. She started having these as soon as we lay down and I enjoyed triggering them with kisses, licking and massage, especially of her nipples. In spite of having had sex twice already, I was hard immediately. She was wet and silky very soon and we went to reverse missionary for intercourse. Ordinarily, she is slow to cum and often holds back for me to finish first. But this time she couldn’t wait and came in about five minutes. We lay together for a while when I became soft, and she gently stroked my cock to make it hard. Then we made love again in the same way. We did this several times over more than an hour, happy with the pleasure, and feeling no interest in trying any other positions that evening.

We didn’t talk about work, we didn’t talk about D. When we have sex, we just talk about what we like in each other and how much we enjoy our friendship.
We just lay in each others arms and talked. Then we showered, dressed and went down to the lobby to eat, having finished our ‘preparation’. D joined for a drink after his game ended.

Did you have an orgasm? Did your partner(s)? M orgasmed. I had done so earlier in the day and didn’t with M. We both feel its nice when the other does. But its not essential and not  a disappointment if we don’t.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We have never felt the need for precautions. It may be foolish, but we’re in otherwise stable marriages and pregnancy is out of the equation at our ages.

What were your REASONS for having this hookup? We are old friends and regular, if infrequent lovers.
But we are always ready to get together when the opportunities arise, as long as we can maintain the secrecy. This chance appeared unexpectedly, but it added enjoyment and zip to our weekend.

Were alcohol or drugs involved? If so, how much? No substances.

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 went about our weekend retreat as we always do, two company leaders, who happen to be casual and platonic friends. I feel good and expect this relationship to continue in the same way. M and I get 6 -10 weekends alone most years and sometimes our families even vacation together. We both feel less tension in our primary relationships than before and have no need to make our relationship more serious or public.

To whom did you talk about the hookup? How did they react? No one. It would greatly destabilize the company and perhaps our families, if it was known. So, its funny that it doesn’t feel dangerous. Perhaps we’re naive, but we are pretty circumspect when we arrange a get-together.

Was this a consensual and/or wanted experience for you? For your partner? Completely. I felt that she steered me to my room, rather than the restaurant, and there was no pretension about doing conference work once we closed the door.

Do you regret this hookup? If so, why? Regret? No way. We were both surprised and happy when D wanted to watch Basketball!

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 surprise and lack of planning was really fun. But the best part was the trust and genuine affection between us. Not orgasming in the ninety minutes that we had, wasn’t even a very small downside.

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? Perhaps, this kind of relationship isn’t really casual. We’re not obligated to each other in any way, except to be honest. We don’t have to be available 24/7 or on demand. We don’t pine for each other when we go months without a chance to be alone. Its a good friendship with mutual emotional support and some sex, but if anyone suspects the true nature of our friendship, they’ve been very discreet. I feel lucky to have it and so does she. Too bad we can’t be more open about it

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