by Old Fool
What’s your gender? Man
How old are you? 63
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Science
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 1
Just a girl called Chloe
How long ago did this hookup happen? 8 yrs
What was your relationship status at the time? Same as current status
How would you best classify this hookup? One-night stand
How long did you know the person before this hookup? For less than 6 months
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? Still fairly recently escaped from the gravity of marital fidelity, I was planning an international trip, and thinking it might present an opportunity to meet someone for a casual evening. I found Chloe online—don’t even remember where at this point—but we connected and quickly switched to emails, which I found as I was thinking of writing this. I reached out to her early, two months before my visit, and had a lovely extended conversation over the ensuing weeks. We eventually agreed to a dinner date. She was late 20s, half my age, a petite brunette, and I was flattered and excited that she agreed to meet.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The week of our arranged date we both had stress-filled days—I had other travels for work and she had to travel to Paris for a job interview—so I wasn’t sure that we were going to make it happen. Arrived in her city, checked into a nice little boutiquey hotel in an old part, and made dinner reservations nearby. She confirmed, and then surprised me by knocking on the door early, before I was ready. When I answered, she practically fell into the room; she seemed so nervous! We did the little cheeky kisses greeting that is so cute, and chatted for a bit as I finished getting ready. She was very petite, maybe 5’2”, and slim but not skinny with a girl-next-door look. I remember that I decided to tie a half-Windsor, instead of a four in hand, and she seemed to enjoy watching me put it together; by the time I was ready she was calm and smiling.
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? We walked to the restaurant, chatting as we went, and enjoyed a very pleasant meal with a couple of glasses of wine. We talked about careers—hers in an early stage, mine much later—and the various (non-sexual) things we enjoyed. I remember we teased each other about how the waiter kept reversing our orders because we crossed gender stereotypes, which continued right through coffee (cappuccino for me, espresso her), which amused her no end. After dinner we strolled a bit and then I invited her back to the hotel, where I had a bottle of bubbles on ice, and she agreed without hesitating.
I put on some music. I had no candles, but the room had a little faux fireplace, which I turned up, poured us glasses, and we had a toast. She sat down beside me and we chatted a bit, then had a quiet moment before we moved into a kiss. After a minute or two she stood up, then knelt on the floor at my knees, looking up at me. She didn’t say anything but reached forward to my belt, undid my pants, and reached in to pull out my dick, already getting hard. She took it in her mouth and began a sensuous oral treat, still looking up. I was in love with her right then!
After a couple of excruciatingly pleasurable moments, I asked if we should move to the bed. We quickly disrobed, and she continued her talented and sensual ministrations there while I began to explore her body wherever I could reach. I was soon moaning and needing a distraction, pleading with her to give me a turn. Working my way down her body, I arrived at her delightful and nicely shaved pussy which I enjoyed stimulating orally and manually as long as she would let me. We graduated from there to mutual oral in several positions (we were both by moaning now), until she asked if she could put on a condom.
I let her roll it on, and she climbed on top to mount me cowgirl style. I love this position for all the obvious reasons, though in giving up control I fear to cum more quickly than I want. And she felt so good. But Chloe proved different; instead of moving rapidly up and down my shaft, she fucked with a slow sensual grinding, stimulating herself as she pleased. Because she was so petite, I could easily move her as I wished too, to change the feeling, or sit up to hug and rub faces as we fucked, and she bent down to tease me with her breasts and kiss. Several times I clamped her hips tight, to maintain control. We fucked and fucked and slowed fucked some more! never separating. Finally, though, came a time when, as I felt an orgasm building, she refused to stop, and instead pushed harder and moved faster, panting; so I stiffened and grabbed her ass to move her harder until she made a series of high pitched little squeals, before stopping, collapsed on my chest. Watching her orgasm was so stunningly beautiful it distracted me so that I didn’t.
I held her there for a minute while she recovered, then rolled her over into missionary, still never having separated, still hard. I raised up on my arms, and asked her if she was ok as I slowly moved in her again. When she nodded, I took my turn, slowly building to a faster pace, finding a rhythm, going harder, not stopping until I came deep inside her and it was my turn to collapse. Altogether we had been steadily engaged for more than two hours. It was “out of category” awesome for me.
Afterward, we cleaned up and lay in bed talking. She didn’t want to cuddle, saying that made her feel too attached, but we chatted for quite a while. I recall that she confided that she was having a hard time finding good lovers among men her age she dated. She wanted to blame porn, but I told her it was probably just inexperience, and that they might be intimidated by someone of her assertiveness. And that she needed to date older men (meaning me of course!). Because she had to work the next day, and I had to travel home, she eventually got dressed, we hugged and kissed goodby, and she left.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
Did your partner have an orgasm? Yes, one
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? The next morning I woke to a lovely and flattering note from her, to which I replied in kind, quite sincerely. It is amazing when two people who don’t know each other at all can connect so perfectly in this way. This encounter was for me the epitome of what casual sex can be, and based on her note, for her as well. I had no expectations for the future because we lived in different countries and rarely visited. Still, we wound up corresponding for months after, and I continued to hope that paths might cross again one day. Eventually that stopped, and we never met again. But the sweet memory remains!
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Making new friends
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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? Very
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? Only Chloe
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? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Fantastically enjoyable sexual experience with a lovely person
What was the WORST thing about this hookup? Nothing unless that we never had the opportunity to reconnect.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. Although not always as perfect as the one described here, I remain deeply grateful for the occasional opportunities I have had for casual sex outside of my committed relationship, which have had an enriching, sustaining effect on my life, and frankly on my marriage.
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? As I was thinking back to this encounter and considering writing here, found the emails with Chloe, along with a couple of pictures that she sent. So nice to remember!
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? Despite some emotional pain over the years both personal and shared, it has been a large net positive and I believe it helped sustain my long time marriage. I suspect casual encounters of one kind or another have always been a more widespread phenomenon that admitted in our repressive society.
What do you think about the Casual Sex Project? A valuable place to archive, share, learn and reflect on the role of casual encounters in society.
You have a hookup story to share? Submit it here!