by I’ve been jerking off to this ever since

: Male
Age: 36
Race/ethnicity: Asian/Chinese
Current location: Singapore
Highest education received: College degree (eg., BA, BS)
Occupation: Banker
Relationship status: Divorced
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 0

You’re My Best Experience

How long ago did this hookup happen? 3 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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 online through a dating site. She was in her mid 40s, in great shape largely  because of her exercise regime (pert butt, toned legs, slim waist). Her face was not exactly pretty but good enough. we were both divorced at the time and looking to date other people.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? First time we met for some drinks and a stroll on the beach, we had a good time but no physical contact was made. Second time we met for dinner and movie, we kissed in the end. Third time we went to see a musical, in the end we fondled each other passionately in my car but didn’t go any further as she had to be somewhere. We both knew it’s going to happen on our forth date and it did, no one needed to instigate it.

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? She was a great lover, her pussy was shaven with lovely scent. We kissed, undressed each other simultaneously. I tongued all over her body, spent a great time licking her pussy, and rimming her anal. She loved it, and in return she gave me a great blowjob. We tried missionary, doggie and girl-on-top positions. She was dripping wet the entire time.

Did you have an orgasm? Did your partner(s)? I did. I think she did also, but never explicitly asked her.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used a condom.

What were your REASONS for having this hookup? Boredom.

Were alcohol or drugs involved? If so, how much? None

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We saw each other a few more times, but never had any expectation or intention that it would lead to a relationship. We clearly liked each other physically and to certain extent emotionally but we both knew we wouldn’t want each other in a relationship. This ended when she met her boyfriend. She is the best lover I have ever had, up until this day I often jerk off to my experience with her, sometimes when I have sex with other women I pretend that I’m with her in my mind.

To whom did you talk about the hookup? How did they react? No one

Was this a consensual and/or wanted experience for you? For your partner? yes and yes

Do you regret this hookup? If so, why? No

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

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