by Jack

Gender: Male
Age: 24
Race/ethnicity: White
Current location: Australia
Highest education received: Some college (not currently in college)
Occupation: Student
Relationship status: Single
How religious are you? Somewhat
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 0

First Good Sex

How long ago did this hookup happen? 6 months

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…)? Paid sex

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? It was just one girl, she was mid twenties blonde. She looked a lot like the actress kaley cucco. She had a bubbly personality an a charming disarming smile.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been quite depressed for a few weeks at that stage. I guess depression is something I live with and mostly manage ok. But that day was particularly hard. As sometimes happens when your brain feels like it’s in fast forward and about to explode you make dumb decisions. I was looking to meet a “professional” woman as my self esteem was through the floor and all my positive inhibitions were gone.
I had looked online and found the address of one such place where sex could be bought. As I was about to get out of the car I saw 2 other gentlemen enter the brothel and I decided to look elsewhere.  After finding another brothel and having an unsatisfying experience I went back to the first mainly hoping for a massage and to feel good about myself. So I went back to the brothel I originally passed on and entered.
After a short wait I met her. She was flirty, bubbly but mostly seemed kind. I was nervous and she made me feel at ease. Then we went to a room, I undressed showered, then she laying on the bed in lingerie signaled that I should lye down next to her.

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? It started when she performed oral on me, then after taking the lead and using mostly female dominant positions, she indicated that she was tired and we went into doggy. After a few minutes I came. I was relieved and happy and she seemed to be smiling too.

Did you have an orgasm? Did your partner(s)? Yes, not sure

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms, tissues, showers and I was tested soon after. But it was in hindsight not the safest experience.

What were your REASONS for having this hookup? I was depressed extremely horny and lonely. And not looking to make good decisions

Were alcohol or drugs involved? If so, how much? No

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 felt good, happy, relieved.
It wasn’t my first time, but before then I had only had bad and uncomfortable sexual experiences . Before this hookup I was convinced that sex was almost a form of self loathing self harm almost. This experience showed me that sex could be great, it could be fun. I probably won’t ever see this person again, but I feel grateful for the experience and I really just hope that she had a good time to.

To whom did you talk about the hookup? How did they react? I haven’t told anyone. I don’t really have any friends and my family are super religious and still think that I am a virgin.

Was this a consensual and/or wanted experience for you? For your partner? Yes it was consensual. As for wanted I suppose in this situation I’m not really sure I wanted it and I can’t speak for her. I’m not conventionally speaking attractive.

Do you regret this hookup? If so, why? I’ve only ever had sex as hookups and I can say that of the few times I have had sex this is the only one I don’t regret.

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? I think the best thing is that I now know what good sex is, and what sexual chemistry is and I can tell if I will have that or not. It was an experience that taught me a lot

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? Typing this out made me feel guilty. Like sharing this story made the guilt and shame of these horrible actions real.

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