by Yaller

Gender: Male
Age: 66
Race/ethnicity: White
Current location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Sports Instructor
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)? 100-200
How many hookup stories have you here posted before? One

Walking The Dog

How long ago did this hookup happen? 5 years

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…)? Short fling

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? I knew Jane through friends who worked with her. She was from another country on a special work visa in the MidWest and came to California to visit them on vacation. One of the friends was a guest in my home and she asked if Jane could stay with us also during her 2 week visit. She was short, no more than 5′, middle aged, about 17 years younger than I. Strongly built, probably 150 lbs, with short hair, very proper manners and conservative dress. She was enthusiastic about everything American, but her job was treating her badly. I liked her, but thought she was a little naive and emotionally reserved, consistent with her home country.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In the first few days in my city, I took her around to see the sights and we talked about her work and family. Her husband had died less than 2 years before and she was still mourning him. It was during winter holidays so we had lots of visitors coming and going and things were festive. On the night before she returned to her job site city, while sitting around chatting with family and visitors, I got up to walk the dog and she said she’d like to come. We walked up the hill in the nearby park, no one else around and no lights. The path was rough and she took my hand as we walked. But once we stopped, she embraced me tightly and turned her face upwards for me to kiss. And what a kiss! Deep tongued, wet, voracious. I love kissing, but my wife hates it and I hadn’t kissed anyone like that in 30 years. We made out for about 15′ but walked into the house as if nothing had happened.

Late at night, when my wife was sound asleep, I crept to Jane’s room in the attic. She had left a red Lava Lamp on and was awake waiting for me, but was terrified that we would be discovered. I got naked and lay beside her, peeling off her PJs and reassured her that my wife is used to me roaming the house at night with insomnia, which is true and linked to the celibacy in our marriage. But I also was sure that Jane had had no lovers except her husband and that she was going to feel confused by this encounter. So as we embraced, I promised that I would not enter her. For the next hour, we gently and quietly explored each other manually and affectionately, both of us leaking like crazy but neither of us orgasming. After that we e-mailed each other, often many times a  day, sending poems and asking each other what it meant. I was right that she was conflicted, she referred to herself as a very Proper Lady and told me that if even a hint of non-marital sex was suspected, she would lose her job in a second and be barred from her profession at home. Still, we were both getting hotter by the day, and worked out a plan. Each of us travels for business several times a year, so we began a series of trysts linked to these trips. New York City, Vail, San Francisco, Cape Cod, The Grand Canyon and more, meeting every 4-5 weeks until her visa was up.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Our first night together away from home was in a run down but famous NYC hotel that has housed innumerable literary and artistic greats. She had to break away from her group on some excuse to meet me and neither of us had eaten in 12 hours. But once we closed the door to our room it was all sex all the time until morning. She was powerful, expressive, amazingly forward, but shy about being seen naked. We tried many positions, went down on each other, came numerous times each and were both surprised by my stamina over and over again. Subsequent trysts were similar, with loud and passionate sex. She learned to be comfortable while naked with the lights on, and we never ended a tryst without planning the next, until she had to return home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She had an IUD and was nearly a virgin. I hadn’t been with anyone but my wife in 30 years. No condoms

What were your REASONS for having this hookup? Lust, mutual loneliness, and I had been wanting to have an affair for some time.

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? She fell in love with me and wanted to have an ongoing, meaningful, if adulterous relationship. I don’t feel that is practical, since we live thousands of miles apart and have encouraged her to see men in her home city. But she feels that they are too cold and controlling, and can’t measure up to what we experienced. We stay in touch and I give her professional advice sometimes, I have seen her in the US on two subsequent visits, hooking up both times. Because we have other friends and relatives where she lives, my wife and I visited her there, even staying in her apartment with her sister and mother. As on our first night, I found her waiting with the light on in the early morning and we made quiet love again.

To whom did you talk about the hookup? How did they react? No one

Was this a consensual and/or wanted experience for you? For your partner? Yes, very much for both of us

Do you regret this hookup? If so, why? No. I am very happy that it happened.

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? It was raw, animal sex, but it opened the door to sexuality again and I learned that I can enjoy extramarital relationships without  feeling that I must break up my family.

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

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

Anything else you want to add about this hookup or anything else? It gave me the confidence to ask a married co-worker to sleep with me on one of those business trips. We’ve been seeing each other regularly for more than 3 years, averaging 15-20 overnights a year, and both are happier in our primary relationships than before. Sometimes, her family accompanies mine on holiday. Nor has our work suffered. If anything, we work better together and everyone there thinks that we are platonic friends.

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