What’s your gender? Man
How old are you? 38
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: College degree (eg., BA, BS)
What’s your occupation? Technology
What’s your current relationship status? Dating casually
Religious affiliation: Jewish
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)? 13
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? This week
What was your relationship status at the time? Same as current status
How would you best classify this hookup? One-night stand
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 met her at an industry conference. She looked very sexy in her pencil skirts and pointed toe heels. I was catching myself looking at her legs every chance I got. We started talking during one of the sessions and then we sat next to each other during lunch. I looked her up on LinkedIn and was surprised to find out she was about 40 years old. She looked more like mid 30s. But it made sense. But it made sense. Women age and know how to look sophisticated and sexy in a way that younger women can’t.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were getting along well. Near the end of the conference, I suggested going for dinner which she accepted. I found out she was recently divorced with a 6 year old. She’s a total MILF. We went for a walk after dinner which got more flirty. She made signals that she was up for a fling. I invited her up to my hotel room for drinks.
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? After a drink we started making out. She looked very sexy in her skirt and heels. I took off her pumps and started massaging get feet. Soon she slid out of her dress and I took off my suit. I was licking her sweaty body all over and moved to her pussy. She was quite wet. We started fucking missionary. After about 15 minutes the sex was so hot I pulled out and shot my load onto her pussy and thighs. I was still insatiable with her so I liked my cum and her juices off her pussy and continued to eat her out. This brought her to her orgasm. She started licking my cock which got me hard again. We then fucked hard and fast for another 15 or so minutes towards another orgasm.
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 laid in bed and talked for a while. Then she left to get back to her hotel. When the conference ended, there were people around us, so we shook hands, smiled and said it was nice to meet. Maybe I will try and connect with her again but the truth is that I am still looking to get married and start a family so I don’t see anything long term here.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)
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? Somewhat
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? None
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? First time being able to seduce a woman that I lusted after.
What was the WORST thing about this hookup? If I only we hooked up earlier in the conference to allow more chances to get together.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I wish I scored more often like this. This will remain a nice memory.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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? It’s not easy.
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