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What’s your gender? Man
How old are you? 64, 27 at the time of the story
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland, Ohio
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? happily retired
What’s your current relationship status? I have a submissive who I allow to serve me four or so days a week and a married mistress who is in a sexless but otherwise loving marriage,
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? I am a dominant with spanking, corset, and leather fetishes
How many sexual partners have you had in your life (including oral sex)? I would guess between 60 and 80, perhaps. Perhaps slightly more. Less than 100, surely. I don’t know for sure, I don’t “keep score”.
How many hookup stories have you here posted before? 7

A Redhead in Her Bed

How long ago did this hookup happen? 37 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

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? She was a bright brassy red head, full of spit and vinegar. She was about 5’8″, a nice figure on the slender side, great legs, very out-going and fun. She was quite pretty and quite a firecracker. I first met her at an ethnic celebration. I was volunteering in a mayoral campaign and she was partying. She was laughing and dancing, obviously having a great time, she was a life-of-the-party sort. She had her hair in ringlets, with a daisy chain crown and was wearing a peasant blouse and a full skirt to match. She was dancing barefoot. I was outgoing, certainly, and there was no one else in the room compared to her. So we ended up talking and flirting and even danced a dance or two. Polkas. It really was fun and she really was definitely the high-light of the night. I liked her, of course, you couldn’t not, but I was confident I’d never see her again, to my modest regret.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The night of the primary election, which we won, we had a big party and it seemed like half the city came. It was a big blast for those of us on the campaign. I was enjoying myself when this very attractive woman in a two piece suit and white blouse, with her red hair pulled back over her shoulders. She looked very professional. I hadn’t seen her around the campaign. She said hello and asked me if I remembered her. I laughed and said if I had ever met a woman as attractive as she was I would certainly remember. She then told me I must have made a better impression on her than she made on me and she reminded me of the polka party. And then I realized from her glorious red hair who she was and I said, “Oh, my god, I can’t believe you are the same woman!” We talked for a bit, we got a drink together, but it was hard to talk because the place was kind of a mad house. Then she said she had to go and asked me if I’d walk her to her car because she didn’t feel safe. On the one hand, while I didn’t know where she parked, I doubted there was any likely danger to her from where we were, on the other hand, maybe she was unfamiliar with this part of downtown and didn’t realize it was perfectly safe. And on the third hand, god, she was hot, so what single guy in his right mind would tell her no??? It turned out she had parked quite a ways away (there was a huge crowd at the party and parking was tight). We had a great conversation going, she had a nice car, a little sports car, and she told me to get in and she’d give me a ride back to the party. The radio came on. It was NPR, which I listened to pretty religiously myself, which sparked even more conversation. She pulled up in front of the party venue and I really didn’t want to get out of the car at that point. I asked her if she wanted to get coffee. She did and we did and the words kept flowing. It was very nice but she said she had to get to bed because she worked early. I told her I really hated to call it a night. She kind of looked down at her hands for a moment and then asked if I’d like to spend the night. Now, this was quite beyond my expectations. “Really?” “You just seem like such a great guy and such a good match.” At that point, I couldn’t think of anything I wanted to do in my life more than go home with her.

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? Well, it started out strangely, at least, it seemed strange to me. She really did just want to go to bed and to sleep. She wore a night gown, which came mid-calf, and had her hair back and her makeup off. She was still very pretty and now prim and proper. I was totally nonplussed because I wasn’t at all sure what her intentions were or why I was there. I told her I usually slept in the nude. She said that was fine and we went to bed. She spooned into me and I held her, me totally nude, her in her night gown and underpants. I started kissing the back of her neck. She said, “Don’t, I need to sleep.” Now I’m really confused. What am I supposed to be doing here??? So I held her, my arms around her waist. She was so lovely and so cool, I just hugged her affectionately and I gave her a few more chaste little kisses on the back of her neck. After a short time, she turned in my arms and looked at me. I looked back at her, still not knowing what was going on. “You really are a nice guy,” she said. Then she turned to face me, me still holding her. She said she had a steady boyfriend, that they were just about engaged, and that he was out of town. “Can you understand?”, she said. I said, “No. I am totally and utterly confused here.” So she starts telling me about her boyfriend. It turns out she was a nurse, her boyfriend was about fifteen years older and was a heart surgeon. She told me she sometimes felt so alone and she really liked me. “There’s something about you,” she said. Well, what do you say to all that? But the thing is, with her hair loose as it was, even in the dark she was so damn beautiful! “Should i go?,” I asked. “No, it feels good that you’re holding me.” And then she kissed me. And we kissed for a bit, for a while. My hands were all over her, gently. It was nice but it was so very strange. And then she finally said, “Oh, what the hell!” and she took off her night gown. We were skin to skin except for her underpants and those soon ended up on the floor beside the bed as well. She didn’t have large breasts or a round ass but she was beautiful, truly beautiful, and I was a little in awe of her, which was pretty unusual for me. I dated a lot and had slept with quite a number of other women by this point. But there was just something so pure about her. It was totally unexpected, everything. So we kissed for a while and I held her and I wanted more but it almost seemed sacrilegious. So even though we were naked, we were sort of chaste, as crazy as that sounds. And then she said, “I really really have to sleep but I don’t think I’ll be able to with you here unless we make love.” In my whole life I have never been in a circumstance like this. I had to make love to a beautiful precious woman so she could sleep??? It was a lot to ask, but, yeah, I made the sacrifice. It started out slow, kissing, me kissing her breasts, she started caressing my cock, which became pretty damn hard pretty damn quick. I kissed her stomach but she pulled me back up to her face and she said, “Please, fuck me.” That was the first and only profanity she uttered the whole night. And all of a sudden, the spell broke. Would I fuck her? Who was the man here??? So I took over. I kissed her, I squeezed her, I got a little rough. She responded, she couldn’t help herself. I forced her head down onto my cock and she licked and sucked and rubbed like it was the sweetest thing she’d ever tasted and then I rolled her over to enter her and suddenly she kind of balled up and resisted. “You have to wear a condom.” “I don’t have a condom!” “I do.” And she rolled over to her bedstand and pulled out a condom. She sucked on my cock again until it was throbbing hard and slipped the tight condom onto me. And then she rolled onto her back and spread her arms. It was a beautiful gesture, just beautiful the way she did it. God, she was so damn beautiful, that’s what I kept thinking. And we fucked and fucked hard and she came noticeably, moaning and crying, and I came gloriously. A truly great fuck on both our parts. And then we kissed a little more and spooned and fell asleep. It was just natural somehow. It was a very strange and wonderful night and she was a strange and wonderful woman.

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 day, I woke up thinking I might be in love with this crazy beautiful woman. She was beautiful first thing in the morning in the cold light of day! So beautiful even with her hair a little tangled and matted! I had totally forgotten about her doctor. But she hadn’t. Well, that wasn’t the end for us or the last time we had sex but it was clear she was going to go for the doctor, for the money and the good life. I really don’t think she loved him. And every time we made love–and that’s what it was, love–it was so damned good! When it was clear I had no shot, we kind of drifted apart. I though about her a lot afterward for a long time. Now I wonder about her, about how her life went. But that’s about it. I haven’t seen or heard of or from her since we parted. Maybe I’ll look her up on the internet now that I’ve shared this here, though now I am very different and she’s probably very different, too. (And I mean beyond the fact that we’re both old now.)

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Clear consent is probably a better answer to the last question than enthusiastic consent. I mean, at the tipping point it was irresistible that we have sex on both our parts. We talked about what happened afterward. She had very mixed feelings. She had come to the party for the sole purpose of finding me again when her friend was out of town. She felt good about it and guilty about it at the same time. And then we did it a few more times. Geez, it seemed for a time there all we talked about was her leaving her boyfriend but she just wouldn’t do it. It was so damn frustrating. “Why are you doing this with me?” I’d ask her. She never had an answer. She wouldn’t answer. But she liked being with me, both in having sex and otherwise. And me with her. I really think she liked me better than her boyfriend. Otherwise the whole relationship makes no sense whatsoever. I never figured it out. I told my eventual wife about her but no one else.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The best thing was being with her. She really was a special person in so many more ways than I’ve shared here. I was very disappointed she wouldn’t leave her boyfriend.

What was the WORST thing about this hookup? Missing her later. But I got over her soon enough. She turned out to be a really great person, better than I would have ever hoped. Nurses are just such great people in general, though, aren’t they?

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me aware that maybe I did want to settle down. I don’t know if I would have married my eventual wife if I hadn’t had this wake-up call. And then after my marriage I would sometimes wonder about what the relationship with the red head had meant to me. It made me look at my lovers and paramours and even myself in these affairs in a different way than I think I may otherwise have. And that was a good thing for all involved.

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? I hope her life went well and she lived happily ever after.

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 has played an important and positive role throughout my life. I wish more people respected its benefits.

What do you think about the Casual Sex Project? I hope it helps refine attitudes.

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