My First (and Only) Affair



What’s your gender? Woman
How old are you? 45
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? Lawyer
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)? 5
How many hookup stories have you here posted before? 0

My First (and only) Affair

How long ago did this hookup happen? 8 years ago

What was your relationship status at the time? In a relationship (monogamous)

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

How long did you know the person before this hookup? Just met that day

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? He was a younger man in his late 20’s. He was very attractive, well-built, blue eyes, brown hair, around 6 feet tall. I didn’t know him at all before. We met at the hotel bar where I was staying for a business trip. I guess I was lonely, a bit horny, and wanted to see what would happen if I showed up at the bar as I dressed for work that day with skirt, stockings, heels, a pretty conservative gray suit. I didn’t feel much about him before the hookup except that he was very hot. But it was a challenge as I’ve been married about 10 years. But with our sex life being so-so due to his inability to “mix it up” in bed, I was open to anything, especially since I was out of town.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was already in the bar when he came in and sat one chair away from me. I noticed him right away but I was playing it that I didn’t. I had my wedding ring on, which I thought might discourage him. He didn’t say anything to me until he noticed I was having a drink (cognac) he didn’t recognize. So he asked me what I was drinking. So we started talking and he was very sweet. After a while, he moved to the stool next to me. So I took the opportunity to turn toward him and give him a front view of myself. So, I guess he initiated it but I was a willing accomplice. Our chat became quite flirtatious. There was no mistaking the signals. At one point he put his hand on my knee and stroked my thigh a bit. “There’s something about a woman in stockings…” he said. After about an hour I thought I would cut to the chase and asked him if he’d like to “see the view from my room.” We both laughed and proceeded to the elevator.

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? It was awkward at first because I think he was a little nervous being with an older woman and I was trying to reconcile the fact that I was married and this would have been the first affair I would have outside that marriage. But that thought quickly evaporated when he took me and we started kissing. It was sort of out of a movie where each person strips the other’s close off and tumble into bed. I was naked except for my thigh highs, which he asked me to keep on. He was completely in the buff. The nice surprise is that his cock was a nice size, bigger than my husband’s by a long shot. Although I have to admit I haven’t had that many partners to know where this guy fit in the size department. I only know I liked what I saw. He was a very good lover.  He took complete control of the situation and I fully surrendered. He licked me until I came. Then he turned me around on my knees. Before he entered me, he spanked me. OMG! I would never have thought that would be such a turn on! I was headed for climaxing with every slap to my ass. He turned me back over, spread my legs and came inside. I had never been filled up like that before. While he was fucking me, he took his finger and put it up my ass. I blew up in an orgasm again and he came at the same time. We were exhausted between the drinks and the sex. But I never felt so alive, desired, and sexy since dating my husband. We rested a bit and didn’t say much to each other. Finally we both agreed that he leave. At that point, I passed out and slept like I had never done in years.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I felt fine the next day, although with some guilt. I never saw or heard from him again…not surprising because we didn’t exchange contact information. How do I feel about him now? I hope whoever he is with is treating him well and that he know he gave me a great memory for the rest of my life. And sometimes, when things get blah with my husband while having sex, I think of him for inspiration!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, I was feeling lonely, Submission / Relinquishing power, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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?  No one!

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? His body.

What was the WORST thing about this hookup? I felt a bit hungover.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m more confident about myself.

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? No

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?  More accepting of it with other people.

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