Screwing Someone’s Boyfriend

by Kitkat

Gender: Female
Age: 25
Race/ethnicity: East Asian
Current location: South East Asia
Highest education received: College degree (eg., BA, BS)
Occupation: Technical
Relationship status: In a committed relationship
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? I love my men forceful
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 1

Screwing Someone’s Boyfriend

How long ago did this hookup happen? Less than 2 months 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…)? 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? My uni senior and my colleague. We used to have drinking sessions together, I thought it was no big deal because I don’t think most guys would be attracted to me, including him as I am not the most conventionally beautiful chick around (which I have been proven wrong on few other occasions). Anyway back to this guy.. I used to find him cute but later on, found him to be annoying before our hook-up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a drinking session (with him and our friends), I went back to my hotel room to call it a night. Soon he texted, asking whether I wanted to check out the roof top bar. We stayed in the same hotel for our business trip. I didn’t give it much thought and just said yes. Only he was there but the bar was already closed. So we took the elevator down. Then he asked if I wanted to check out his room, which I said yes because duh.. I really thought he meant it. Only when we were alone in the room, he landed his hand on my hip before pulling me over to him and kissing me, I realized that was it. I was lured by another guy whom I never suspected anything because of my naivety 🙁

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? I was not exactly sexually attracted to him. I didn’t see it coming. I became so detached and unresponsive while his hands and lips were over my face, neck and body. But I didn’t say no either, just told him I had to leave fast. I have to admit I was indeed looking for ONS on my business trip (just that he was never a candidate that crossed my mind haha). I helped him take off my dress and bra. He told me that I was wet while fingering me. Before I knew he parted my legs and positioned himself between me and again, before I knew it, he was already inside me, without a condom.

Did you have an orgasm? Did your partner(s)? We changed position a few times – missionary (he was kissing me heavily and biting my nipple hard while at it), doggy (he grabbed my breasts from behind while thrusting) and spooning (boy, he really knew what he was doing). At one point, I got out of the bed, offered to give him oral so that he could come in my mouth (because we weren’t using a condom). I was sucking his cock and before long, I was slowly and surely pushed back to the carpeted floor and he got on top of me again pumping. This time, he parted my leg further and thrust deeper, making me moan louder which he clearly took note of and was satisfied with. Not long after that, he pulled out and came on my body (after me begging him not to come inside me). He did have an orgasm, I didn’t.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. No discussing STI history either.*facepalm*

What were your REASONS for having this hookup? I was looking for ONS while away on business trip – thrill to spice up my life and be fucked real hard (because my boyfriend let me down in that). It just happened that he was the guy in this hookup.

Were alcohol or drugs involved? If so, how much? Alcohol, we were tipsy but I was fairly conscious of what happened.

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 cleaned up and I left. All took place in less than 30 minutes. I told him not to tell any soul.

To whom did you talk about the hookup? How did they react? None. I must never tell anyone, particularly my girlfriends and colleagues. The only persons who are aware of my serial cheating behavior are my hook-up partners.

Was this a consensual and/or wanted experience for you? For your partner? Consensual but it wasn’t something I exactly wanted from him. I could have put on a fight and resisted or walked away but I didn’t. But I have to admit, being tipsy and all that shit did put me in a physically vulnerable position – hard to think clear so I just went with the flow. If he indeed intended to force it on me, I doubt I could fight much. Something for me to reflect on :(((

It was a wanted experience for him. I am not sure though how long had he been thinking of it (bedding me) or it was simply a on-the-spur-of-the-moment night for him.

Do you regret this hookup? If so, why? Yes, I do regret. It was against my principle of sleeping with colleague from the same unit. I finally shit at where I eat. In my case, it brings awkwardness. I hardly even bothered to initiate any talks with him.

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? BEST: I had sex. With another guy who is not my boyfriend. With someone who has a girlfriend (ticked off my list of screwing someone’s boyfriend). And more importantly, he really knew what he was doing and it was a welcoming change from the sex I get from my boyfriend.

WORST: I lost more and more faith in humanity. I finally met another cheater (the conflicted thrill and shame is something!!). Why would he cheat on his tall, beautiful model-like girlfriend is beyond me. At the same time, I wonder was that how my other hook-up partners felt when they bedded me – a woman with boyfriend.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup or anything else? I need to sort things out with my boyfriend. :(((
I wish to experience casual sex with more men.

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