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What’s your gender? Man
How old are you? 26
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Singapore
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Took her virginity by accident!

How long ago did this hookup happen? 2 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 6 months

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 through friends a couple of weeks before. She was Chinese and about 5’4″, fit but not skinny with a round well-shaped butt. Her frame was fairly large for a Chinese girl despite her height and her face was pretty average, all in all I would say 5/10. She came across immediately as highly intelligent and successful holding a good job and carrying herself with professional dignity, which was probably what drew me to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was obvious she was into me almost straight after meeting, even though she tried not to show it. I soon found out she had just gotten out of a long-term relationship and was enjoying her new found freedom. We had gone out for drinks with some friends but split off to head to a club event, in the end the club turned out too crowded and we went for a walk instead which ended in us having a long conversation about life, career and aspirations. We settled for a bench and soon the conversation turned sexual and we started making out.

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 went back to my place and ended up in my bed. I got her naked very quickly and proceeded to eat her out. She was not shaven which turned me off a bit to be honest, but seem to observe a high level of hygiene. It became obvious very quickly she was enjoying it but she confessed that having an orgasm has always been a challenge for her (apparently her previous partner could never make her cum) and that she was also a virgin despite some experience with oral sex/heavy petting. I continued licking her for a while which made her extremely wet and the juices were starting to soak my bed. This was when I positioned myself between her legs and rubbed the tip of my manhood on a vagina. She was clearly enjoying this but I could sense her weariness of the fact that penetration might occur relatively soon. Given the circumstances, it was hard for me to not attempt penetration, and I slowly inched the tip of my penis into her. When resistance was met by her hymen, she complained about the pain which would lead me to withdraw slowly. This happened quite possibly a dozen times, which I think allowed a gradual expansion of her vagina. All these occurred concurrent with me kissing her/ sucking on her nipples in missionary position. At some point, I felt the resistance give way and felt the warmth of her now extremely moist vagina engulf my manhood. It was deeply satisfying to feel the tightness of her vagina and the ecstatic look on her face. She seemed to be confused at the new feeling as well as the lack of pain. We started forming a rhythm and after 5 or so minutes, I could recognize the look of an orgasm building up on her face. This coupled with her tightness brought me to the end of my own climax. I held on as long as I could, by now she was moaning very audibly and I wanted her to experience quite possibly her first orgasm with me. We both came at the same time, she in the final burst of my intensified thrusting and I to the sounds of her ecstasy. I withdrew at the very last moment, and the intensity of the orgasm was something I had never experienced before, as a shot my load in a long streak that went up to her neck.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 there for what seemed like an eternity before she asked, was that full sex. And I said yes, she seemed to be a little disappointed in herself for a short period of time. We hooked up many times of the following 3 months but at some point she started developing feelings despite me having warned her of my unwillingness to settle yet. We ended things shortly after.

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

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? Somewhat

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? Close friends.

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

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? A little bit

Why do you regret this hookup? Breaking her heart, inevitably. She was convinced she could have a relationship with me despite me being upfront with her.

What was the BEST thing about this hookup? The sex, which was amazing because I think I really respected her drive and intelligence, which made the sex with her absolutely gratifying.

What was the WORST thing about this hookup? Her heartbreak and the way we left it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I started reflecting on whether it was my fault she got her and if this is the person I want to be.

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

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

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