Cheat With My Crush

by Jay

Gender: Male
Age: 26
Race/ethnicity: Asian
Current location: Singapore
Highest education received: College degree (eg., BA, BS)
Occupation: Executive
Relationship status: Attached
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Cheat With My Crush

How long ago did this hookup happen? 2 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…)? Friends with benefit

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? She used to be my classmate, I am always attracted to her big tits and petite frame.
She used to reject me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Met her during one of the class gathering. Asked her out for drinks and subsequently we both got horny.

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 got tipsy and i told her she is not going home, she smiled and we checked in a budget hotel at the pretext of buying more alcohol to drink in the room. I always wanted to go rough on her as she looked down on me before when i am younger.

She resisted my attempt to have sex at first but she gave in after i insisted, both of us were tipsy and we had a real rough sex. I only focus on getting the most out of her and making her feel pain.

I grabbed her tits and kept pumping her despite her plea to stop. We have sex twice that night. The following day, she texted me that her vagina is sore and tease me to fuck her again… She realized that she is into rough sex and we have been meeting up for such session for the pass few weeks.

Did you have an orgasm? Did your partner(s)? Yes we both came twice.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nil

What were your REASONS for having this hookup? Fulfill my desire

Were alcohol or drugs involved? If so, how much? Yes, 1 bottle of vodka

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? Friends with benefits

To whom did you talk about the hookup? How did they react? My ex classmates, they were amused

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

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

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 thing i managed to hook up with my crush and find someone who is willing to be submissive on bed.

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

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

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