by Jhun

Gender: Male
Age: 34
Race/ethnicity: Filipino
Current location: Philippines
Highest education received: College degree (eg., BA, BS)
Relationship status: In a relationship
Religious affiliation: Catholic
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? 1

Woman In Need

How long ago did this hookup happen? Last month

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…)? One-night stand

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? 26, 5-foot tall, tan skinned, wavy brown hair, chubby, big D cup tits, braces. I met her through Craigslist; I posted an ad for a casual hookup. She said she was in trouble and would do anything for quick cash. In the 2-hour ride to get to our meet up place, I was thinking it was a scam and I would get beaten up and robbed. I also thought about just giving her the money and leaving.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a metro station. When I saw her, I decided to follow through, even though she’s not really my type (I prefer lighter-skinned women). I don’t know why I decided to follow through instead of just being the Good Samaritan. We walked to a nearby motel.

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 talked when we got to our room. She explained her legal woes and I empathized. She asked me why I was meeting women on Craigslist even though I had a girlfriend. Shortly after, I told her to undress. She said she was a giver so she got on top of me first. She was a great kisser. Then, she gave me the best blowjob I ever had. Then, she put my cock between her tits and gave me a titty fuck.
I told her it was my turn and I got on top of her. I fingered her until she was so wet and begging me to fuck her. We did it missionary first and she complimented how big my cock was and how great I was. She was loud and noisy. After a while, she got back on top. When she stopped humping me, I thrust up into her. Afterwards, we did the doggy with me fingering her clit. That’s when I finally came.

Did you have an orgasm? Did your partner(s)? I came once. Based on how wet she was, I’d say she came a couple of times. The biggest one was when she was on top and I was thrusting her.

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

What were your REASONS for having this hookup? I guess I was not satisfied with the sex I was getting from the girlfriend. I was looking for thrill and variety. I didn’t expect this girl I met would be so good at it as most of the hookups I’ve had were boring.

Were alcohol or drugs involved? If so, how much? Nope.

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? I had only brought one condom so we just talked after sex. When our time at the motel was up, I walked her to where she could get a ride home. I felt great after the hookup, like a kid getting an unexpected present. But even though the sex was great, I still didn’t want her suddenly coming into my life; one worthwhile night was enough.

To whom did you talk about the hookup? How did they react? I have described it to “email buddies” (women I met through Craigslist). They are impressed.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual for both of us. She was the one who contacted me by responding to my ad.

Do you regret this hookup? If so, why? I don’t regret it.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The sex was great. The worst thing is that I should have brought more condoms and booked the room longer. At a time when I was about to quit looking for casual hookups, it made me wonder what having such a great experience like this one means. Is it a sign for me to continue?

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

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