One-Night Stand That Led To An Affair



What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Insurance
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

One-Night Stand That Led To An Affair

How long ago did this hookup happen? 15 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

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? Sandy and I were co-workers who worked in different locations. We both traveled for work and our paths would cross 3-4 times a year and we’d travel together for a few days. We had a lot in common – mid-forties, married more than 20 years, 3 children. We had a friendly, somewhat flirty relationship, but nothing had ever come of it. Sandy is very attractive: 5’,3”, 120 lbs., blond hair, really nice figure. To be honest I had fantasized often about hooking up with her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On this occasion, we were together for a couple of nights. The first night we went out to a pub-style restaurant for dinner. We sat at the bar and it was crowded and somewhat loud. Sandy leaned close to me to talk and her soft left breast was pressed against my right arm. Naturally, I got an erection. Sandy was more flirtatious than usual, saying a lot of suggestive things to me, and even as the crowd thinned out she remained pressed tightly against me. I was convinced we were going to end up sleeping together so I was shocked when, as we were leaving, she apologized for being such a flirt and said she hoped she hadn’t led me on. It was so unlike Sandy to be a tease like that that I blurted out the first thing that came to mind: “You mean you’re really not going to sleep with me?”

Sandy was absolutely silent. It seemed like forever, although it was probably only 15 seconds or so. I had no idea what she was going to do. Slap me? Turn and walk out? Finally, she said, “I want to go to bed with you. I will go to bed with you. But not tonight, tomorrow.” She wouldn’t tell me why she wanted to wait and she wouldn’t change her mind, so I gave up and agreed.

I had the worst case of blue balls that night after being hard for so long. I almost masturbated to get some relief but I resisted the urge. I wanted to save it for the next day because I had an idea that Sandy would be dynamite in bed.

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 worked together the next day and it was business as usual. We got along as well as always, but neither of us mentioned the night before. I half thought she might get cold feet but that wasn’t like the Sandy I knew; she’d always kept her word. Later at the hotel, when I went to her room to pick her up for dinner, she drew me close and gave me a long deep kiss on the lips. That’s when I knew for sure that we’d have fun later. After dinner, back at the hotel Sandy pressed the buttons for both our floors and asked me to give her ten minutes, then came down.

Sandy opened the door wearing a short silk robe, open at the waist. I kissed her and found she was naked underneath. Her skin was incredibly soft as I rubbed her back and her amazing ass. Off came her robe and she stripped me quickly. I went down on her briefly, and then she took me in her mouth. Then she asked me to fuck her. I reached for a condom but she told me none was needed. We then made it right there on her couch; we didn’t even make it to the bed. It was a great fuck. Sandy was really into it, moaning and urging me on. I didn’t even try to hold back and make it last. I was so horny that I fucked her hard and deep and finally came rather quickly.

Sandy still hadn’t come and I was determined that rectify that, but first, we decided to move the action to my room. I had a king-sized bed, compared to the standard double bed in Sandy’s room.
We got to my room and Sandy took over. She mounted me and rode me like a champ. First, she would sit straight up and rotate her hips, trying to work my cock as deep into her as possible. Then after a few minutes, she would lean down onto me, mashing her breasts into my chest and grinding her clit onto my pubic bone for stimulation. Switching back and forth like this, she worked her way to 3 tremendous orgasms over the next 30 minutes, each louder and more intense than the last. I was in awe. Sandy absolutely loves to fuck. I’ve never seen a woman enjoy sex as much as her. Finally, she lay back with a dreamy, satisfied smile. I, however, was still hard as a rock. Having already come once and concentrating so much on giving Sandy pleasure, I stayed hard the whole time without coming again. I moved toward her and her eyes widened in surprise. She said, “You’re still going? You’re amazing!” as she smiled and guided me into her. This time it was slower and less frantic than the first, and ultimately more enjoyable. After I came again we drifted off to sleep.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? That was the start of a beautiful affair. Over the next 3 years or so we met as often as possible, had some incredible sex and really came to love each other, even though we knew from the start that we couldn’t be together. She eventually confessed that the reason she wouldn’t sleep with me that first night was that she was just getting over her menstrual period that day, and didn’t want to take the chance of a mess. I was really touched that she shared such an intimate detail with me. The affair ended after Sandy took a job with another company, but we’ve remained good friends and talk often on the telephone.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Fertility awareness (days counting, temperature)

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? 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? Nobody. I’ve never been the type to kiss and tell, which I think may be partly why Sandy was attracted to me.

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? The sex was way better than my fantasies. Over the course of our affair, the sex was the best I ever had. I had just wanted to hook up at least once and I got so much more than that in the long run.

What was the WORST thing about this hookup? During the ensuing affair, we fell in love, and I think we both regretted that we couldn’t be together. Still, I wouldn’t take a single thing back.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Opened my eyes to how passionate a woman can be in bed.

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? My marriage actually improved while I was hooking up with Sandy. My wife has a lower sex drive than me, and I think I was more cheerful and not as resentful while I was involved with Sandy.

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? I think the world would be a better place with a lot more casual sex.

What do you think about the Casual Sex Project? Terrific!

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