What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada, Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Medical
What’s your current relationship status? Dating casually
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)? 18
How many hookup stories have you here posted before? 1
Sitting On The Kitchen Counter In Bra And Panties At 3 am
How long ago did this hookup happen? Last month
What was your relationship status at the time? Same as current status
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? We met on a dating site. She is the same age as me: 40. She is divorced with two kids, slim, blonde, with green eyes, 163 cm, healthy, and in good shape. She had stunning online photos and she was a former journalist and is now an executive in corporate communications. She was really into me for my intellectual and romantic online profile. She lived 80 km away, which was a good hour’s drive, but she drove into town on our first date for lunch and afternoon tea. In real life, she had a romantic, but practical personality and came across a bit nerdy. She brought a notebook and took notes! She said this was the journalist in her. She seemed to love that I was a good interview subject. She was intrigued by my field and my witty remarks. I was surprised, but it was fun seeing that this was a (former) journalist that seemed to be falling for her interview subject. We had a great time. When I walked her to her car, she gave me a a very romantic kiss, which I escalated to a more passionate kiss. She would normally be too old for my target, and she does have kids, while I don’t, but her interest in me was stimulating my interest. She also kept saying that “at this age (meaning 40)…” she wanted a more exciting life, now that her oldest was 17. I wasn’t sure what that meant, but it sounded like a fling. Though I didn’t push it in case she wanted more.
For our second date, we went shopping along a trendy street in Toronto. She was looking for clothes and shoes, and I tagged along. She wore jeans on both our dates, but as I saw her model some pencil skirts and dresses. I thought she had a sexy body and great legs. We saw a small leather cross body handbag with a cute leather dog patch on the side. It was a designer bag. She was enamored with it. I said wow, that’s over $250. She said it’s the kind of bag that a lady wears with a short skirt and heels. I told her I’d love to see her dress like that. She said she would love to dress like that for me. That comment put me over the edge. I bought the bag for her and said we are going on a date with that in mind. She loved my initiative.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had a dinner date. She showed up wearing a very short skirt, an elegant blouse blouse, and 3 inch heels, plus the cute handbag. Though she was 40, she knew how to dress. She was fashionable, stunning, and sexy. We could feel the sexual and romantic attraction. She was a very good conversationalist. She loved asking me questions, and communication was really relaxed and easy between the both of us. After dinner, we held hands and took a short walk to a jazz place. We were seated at a high table. She crossed her sexy legs and dangled them over the edge knowing that she was seducing me. We got flirty and were touching each other a lot. It was hard to be close sitting at the high table though, so I just said, “why don’t we go back to my place where it is quieter,” to which she accepted enthusiastically.
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? At my condo, we held hands on the elevator. When we were finally alone on the elevator, we started kissing. We had our arms around each other as we made our way down the hall to my unit. The sexual tension was escalating by the moment. When we entered my condo, we were making out before the door even closed. We didn’t have sex right away. There was a lot of kissing and making out and talking. It was a new kind of intellectual foreplay for me that was actually quite arousing. Eventually I just said, why don’t you spend the night, and we went to the bedroom. She seemed a little shy. The sex started with me massaging her, then finger sex, then oral sex, then a variety of missionary positions. We both came when she rode me doggy style. We were both hungry afterward, so we went to the kitchen. That led to more intellectual foreplay. She sat on the kitchen counter at 3 am in her bra and panties as we talked and I made and served her bite sized food from my fingers. After that, we had sex again. The second time, it was more primal. I fucked her doggy style, pounding her to an orgasm then switched positions and came into her fucking her missionary style.
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? We only got a few hours of sleep. In the morning, I said, “you don’t want to do the walk of shame dressed that sexy and hot this early in the morning.” She said, “why not?” So we went for brunch. She liked the idea of dressing in heels and and a short skirt for a weekend brunch at 11 am. Just so it wouldn’t look too out of place, we chose a more upscale brunch spot. This woman knows how to be sexy and how to seduce a guy! I’m not considering a LTR leading to marriage, but I am interested in a fling for a while. It seems she’s “at a point in her life” where she wants to express her sexuality again. We are still dating and having sex on a regular basis, every other weekend when her kids are with her ex.
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)
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 gave enthusiastic consent
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? I don’t know / I’m not sure
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? Being attracted to her on an intellectual and emotional level, and being attracted to her body and legs. Also her being so into me, and being able to consummate that with a few rounds of sex.
What was the WORST thing about this hookup? That I’m not interested in long term commitment, but we are still together, dating (casually to me), and enjoying each other and enjoying the sex.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Is dating consistently, just to have access to frequent sex, considered casual sex?
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? A little negative
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