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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
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Medicine
What’s your current relationship status? Dating casually
Religious affiliation: Christian
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)? 18
How many hookup stories have you here posted before? 0

Talking Dirty

How long ago did this hookup happen? 16 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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

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? I was a grad student at the time. My friend and I went to a club. We were in our mid 20s at the time. He was a very attractive guy with model looks. So I was not too surprised when two women in their early 30’s approached us. I expected both of them to be hitting on my friend. The more attractive one was hitting on my friend pretty assertively. What did surprise me was that the other one was really into me. She was not as attractive as her friend, but I still found her appealing. There was a confidence that these women had about hitting on us that we did not see from women our own age. It was clear that they were both very much into each of us. Though somewhat intimidated by these two older women, I also found there approach very sexy. The one interested in me was about 165 cm with mid-length brown hair. I got her phone number when we left at the end of the night. I made a date for the following Friday.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had a dinner date. Afterwards I suggested we get drinks at a bar. I chose what I thought was a cool spot. It was very loud. As soon as we walked in, she said, “I am so not into this.” Then she suggested we go back to her place for a drink. At her place, we started on our drinks, but barely after two sips, she put her glass down. She took my glass and put it down and reached in to me to kiss and make out. I just went with it. We quickly took our clothes off. I already had a huge erection. Back them, with my inexperience, I wanted to have penetrative sex right away, but she stopped me. She grabbed my fingers and showed me how to rub her clitoris. She said “just like that.” I varied my motions, and she responded with “yes, like that.” This type of feedback was new to me, but the communication and intimacy was very arousing. When she was quite wet, she said “feel me inside.” I inserted my finger into her pussy and started finger fucking her. She grabbed my hand and turned it and said “right there” and she guided my hand into a rhythm. As I picked up the rhythm, her moans got louder and longer. She said “I’m coming. Don’t stop.” To this day, I remember her cues” “faster, yes, like that” and I still get hard from the memories. After her orgasm, we went into her bedroom.

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 were making out on her bed. She grabbed my hard cock and started rubbing it against her pussy. She said “what’s that?” Stupid me, I didn’t know how to respond, so I said, “what was that?” She skillfully positioned the tip of my cock against her pussy. It would have just taken a thrust from me to penetrate. She said again “what’s that?” I was not sure how to respond. I just laid there as she swirled the tip of my cock around her pussy. Then she said “tell me how you want to get to know me.” That’s when I figured out that this was talking dirty. I said “I want my cock inside you.” She said “yes.” I was always worried about STD’s but her seduction was so sexy and the sex talk was really turning me on. I didn’t bring a condom. I said, “do you want me now?”
Yes.
“Do you want to feel my hard cock inside you?”
Yes.
I slid inside her. “That feels so good”
She was moaning now.
“Your wet pussy feels so good and tight.”
She lifted her legs and said, “go deeper”
We just kept going like that, with her verbal cues and me getting more uninhibited with my sex talk.
At that point in my life, I usually came within a few minutes of sex, but the sex talk actually paced me. I was focusing on her cues, on giving her pleasure, because she knew how to ask for it. I was able to fuck her missionary, then doggie, all the while talking dirty to each other. She rode me, grinding herself to an orgasm. Back in missionary position, as I felt my orgasm coming, I said “I’m going to come.” I actually stopped and was about to pull out. She wrapped her legs tight around my back and said “I’m on the pill. I want your cum inside me.” So I kept going.
“You feel so hot. You are so tight. You make me feel so good.”
Fuck me.
With that, I felt a very satisfying ejaculation as my cock filled her pussy with my cum.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? I was so turned on, I kept making out with her. I slept over. I enjoyed the feel of her naked body. When we woke up in the morning, I had a huge morning erection. We were lying in a spooning position. I licked her ears, I fingered her pussy and whispered “my cock wants to be inside you again.” She pushed back, allowing me to enter her. She rolled onto her tummy and I laid on top of her and pounded into her until we both came. That was a new position for me.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant

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? My friend who went to the club with me. It turned out he and the woman he met also hooked up.

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

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Up till then, I was only having sex with “girls.” This was a real “woman” who knew what she wanted sexually and how to get it. I learned a lot from her. Up to that point, I only had 5 partners, all around my age. I thought the sex was good up to that point, but this experience re-calibrated my expectations from a partner. Ever since, I knew that I want sex talk and dirty talk as part of the communication and how to connect with my partner.

What was the WORST thing about this hookup? She wanted a relationship. We had an intense sexual relationship that lasted about 6 months. I wanted someone younger, closer to my age. I was 24 at the time and she was 32.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s great if you can get it.,

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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