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What’s your gender? Man
How old are you? 29
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineer
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)? 4
How many hookup stories have you here posted before? 0

Sex With Wife’s Friend (My Colleague)

How long ago did this hookup happen? 2 days ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For 1 to 3 years

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 has long brunette hair. Slim and tall. B size breast and curvy ass. She is my wife’s friend who happen to be my colleague as well. We all work in the same company.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It begun on Friday as I brought her out for dinner to celebrate her last day of being single. She got married today. My wife couldn’t join us as she had plans with her relatives and told me to carry on with the dinner plan. As we were dining drinking, she got tipsy and started saying how she regrets not having sex with anyone else other than her boyfriend (now husband). I was surprised to hear the admission considering how hot she was and how many times I had imagined having sex with her at work. I decided to keep my thoughts to myself and just kept the conversation going. At the end of the dinner, she was drunk and told me she couldn’t make it home by herself. I offered to send her home. She insisted on carrying on to drink and told me to drive and book a hotel room for a night. I was surprised but excited knowing the possibility of having sex with her could finally happen for me.

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? Once we got into our room, she immediately pushed me on to the bed and got into a cowgirl position. She removed her dress and revealed her hot figure in a black lace bra and black translucent panties. I could see her hard pink nipple through her bra and her nicely trimmed pussy hair through her panties. I immediately got a hard on and threw her down on the bed and got on top of her. I pulled her bra cups aside and started licking her erected left nipples, flicking her right nipples with my fingers and gently rubbing her pussy with my knees. She let out a soft moan and begun pushing her pussy harder against my knees. I continued licking her left nipples but move my right hand inside her panties, sliding over her trimmed pussy hair and begun rubbing her clit in circular motion. After a few minutes of licking her nipples and rubbing her clit, she came and her body convulsed. Not wanting to let the momentum go away, I immediately put 2 fingers in her soaking wet pussy and started rubbing her G-spot. She begun to moan louder and she realised it too, hence she grabbed my head and pressed me against her lips and we started kissing heavily to soften her moans. Within a few minutes, she came again. After that we swapped positions again and she got on top of me. She removed her bra, followed by my shirt and pants. She leaned on me and started kissing me again, slowly moving her lips down my chest before reaching my stiff cock. She gave a kiss on the head of my cock, looked at me seductively and begun giving me a blowjob. She was very good at it and kept using her tongue to edge me to orgasm and stop. i told her i was going to cum to which she responded, “no. not yet. I want to feel what it’s like to have cum inside me’. She told me she is on birth control pills and she has had bareback sex with her boyfriend before but he doesn’t seem to be able to cum via penetration in her pussy. She always has to finish him off with a handjob. Getting more excited after hearing that, I told her I would gladly obliged cumming inside her. She pulled her panties aside and guided my cock into her pussy. it was tight as i had always imagined. i could feel her pussy wrapping my cock tightly. She begun riding me slowly and started moving up and down my cock quickly as she begun to reach orgasm. She grabbed both my hands to squeeze her breast as she rode my cock. I squeezed and flicked her nipples alternately and this seem to turned her on more as her moans got louder and her riding got faster. I was so turned on by her moans that I shot a big load of cum in her pussy. It was a massive cumshot as me and my wife have not had sex for a few months and my sexual urges has bern building up. As I came into her, I felt her pussy convulsed against my cock as she let out a loud grunt and came for a third time. She fell onto my arms and I hugged her tightly for a while and kissing her forehead to compliment the night.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? After laying in bed for awhile, we both went to shower together, sobered up and talked about how we could never tell our partners about what happen. We both admitted the sex was great but it could never happen again. I dropped her home later that night and went back to my own place. I attended her wedding ceremony this morning. However, whenever I looked at her and her husband together during the ceremony today, I cannot help but think how great it was to be the first guy to cum inside his wife.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? nobody

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting to see my colleague naked and having sex with her after all this while working with her and imagining what’s underneath her dress and her sexual desires are.

What was the WORST thing about this hookup? Cheating on my wife. She did not deserve it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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