Guest Bedroom

by OldYaller

What’s your gender? Man
How old are you? 69
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Several
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Its apart of who I am and how I relate to female friends and acquaintances.
How many sexual partners have you had in your life (including oral sex)? > 100
How many hookup stories have you here posted before? 6-7

Guest Bedroom

How long ago did this hookup happen? 3 days

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

How would you best classify this hookup? Off and on

How long did you know the person before this hookup? For 1 to 3 years

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 60, less than 5′ tall, fit from daily Yoga, animated, always looks delighted about something. I met her through co-workers and we have had an on-again, off-again friendship of lunches, morning coffees and occasional sex for almost two years. She and her husband occupy parallel lives, occupying different parts of their house, barely talking. My wife and I are close, but she dislikes physical contact of any kind. So, L and I share this lack of affection in our home lives. L’s smile is mysterious, playful and inviting. She is froward in her e-mails and texts, but coy in person, which sometimes leaves me wondering about her desires.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My family and I are on vacation in the mountains, but a small crisis at work required me to drive back to the city for a day. I texted L to see if she’d like morning coffee or lunch near her office by the harbor. To my surprise, she suggested dinner and threw in that she cold stay in the City that night (Its an hour commute to her home). Of course I said yes and made a reservation at a restaurant run by a local Buddhist Monastery, facing the sea. Over dinner, I clarified that her ‘staying over’ didn’t mean staying at her brother’s house. She admitted that she considered it a possibility, but would rather stay with me. When we got home, we had tea and chatted. She feared that someone from my family, all of them 200 miles away, would come in unexpectedly. I suggested we sleep in the Master Bedroom, because she was limping from a recent fall and stairs were uncomfortable for her. But she asked for a Guest room, out of “respect”.

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? Once in bed, L again became coy, enjoying hugs, massage and kissing, but nor initiating or advancing the interaction herself. I gave her long oral sex to an orgasm. Then rolled over and put her on top of me, face to face. We rubbed together, massaging clitoris and penis together, both making happy, small groaning and cries of pleasure. But I was semi-soft and she was not trying to take me in. Eventually, we went to sleep, entwined for the rest of the night. When I awoke at six AM, her head was on my shoulder and her legs open with one resting on mine. I reached down and softly massaged her mons and clitoris, soon I felt wetness and extended the massage to her vagina, she moaned and pushed upward, eyes
closed. As I continued, I became quite hard and rolled to my back, pulling her onto my chest. I ran my penis back and forth between her wet and soft vulva for about 10′. It was intense for both of us, but she made no attempt to take me in. So I took my penis in may hand, positioned it and slid in, with only minimal friction. She immediately pressed herself against me, embraced me tightly and pressed her cheek against mine. We lay clinched like this for a few minutes, then I began pulsing my penis, then slowly thrusting. With each movement, she clutched me more tightly and remained silent. Gradually, the tension grew an climax approached. As it did and my breathing changed, she began to grind on me, almost desperately. I came forcefully, but with less need for vigorous thrusting than usual, and she came right after, clenching her legs together, as she always does at that moment.

How sexually satisfying was this hookup? Somewhat

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 lay in bed quietly, with her head on my shoulder again. I wondered about the way that she held me after I entered her; she hadn’t done that before, and I felt that it was a sign of deep ambivalence, perhaps regret. She said “You did it all”, as a way of rejecting responsibility, I think.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Old age and assumption of safety.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? The CSP, they don’t ever react.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? I don’t know / I’m not sure

Why do you regret this hookup? No

What was the BEST thing about this hookup? Lovely evening with a thoughtful and generous friend. Intercourse

What was the WORST thing about this hookup? L’s passivity during sex, the ambivalent consent. She is always flirtatious and encouraging when we communicate from afar, then passive and accepting when we are together.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, but it makes me unsure about continuing with her.

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? After breakfast in the morning, I told her that we could spend another night together next month, when my wife is away for a conference. She smiled and said yes.

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? Casual sex, meaning uncommitted monogamous sex, is a nearly universal human experience, perhaps even in the most repressive Middle Eastern, Patriarchal cultures.

What do you think about the Casual Sex Project? The stories are more or less interesting, depending on the reader’s psychology and position in life, I suppose. But being a collection of self-reported anecdotes, I doubt there is much it can contribute to the study of the phenomenon. But it provides a venue to write about and reflect on the experiences for more than just their physical aspects.

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